Above $1 Million Winter Park FL Real Estate, Homes, Condos for Sale

3 Beds ⋅ 3.5 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code

Historically elegant SINGLE-STORY home home with 3 OVERSIZED bedrooms, 3 Full bathrooms, and 2 half bathrooms, located on one of the most SOUGHT AFTER streets in the Heart of Winter Park. Located on a expansive fully FENCED CORNER LOT (0.39 acres) featuring lush landscaping. Conveniently located near PARK AVENUE, the Interlachen GOLF & COUNTRY CLUB, and A-RATE SCHOOLS. Well preserved HARDWOOD floors grace the living spaces (original under carpet in bedrooms too) and create flow through the BRIGHT and AIRY layout. Relax by the glow of the WOOD BURNING FIREPLACE and stock your favorite books in the ELEGANT BUILT-IN'S. Not only is the primary bedroom spacious (with double sinks, jetted tub, walk-in shower ensuite bathroom), but all bedrooms are oversized and offer plenty of CLOSET SPACE. Bonus 1/2 bath connected to one of the bedrooms for an in-law or GUEST ENSUITE. Additional features that will also catch your eye are the sliding FRENCH DOORS, large windows for lots of natural light, charming brick patio, GARDEN area, circular driveway for easy in and out access, full 2 CAR GARAGE with workshop, storage built-ins, and half bath, as well as architectural details indicative of the time period it was built. There are plenty of modern UPDATES too, with a NEW ROOF in 2021, NEW AC in 2020, New fence in 2021, and updated unground utilities. Live the quintessential Winter Park lifestyle and request a tour of your future home.

1166 Palmer Avenue, Winter Park

$1,500,000

4 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 07 SubDv. ⋅ 32792 Zip Code

Featured on the American Dream Network! Discover unparalleled luxury and modern living, a completely renovated custom home situated in the heart of Winter Park. This exquisite 4-bedroom, 4-bathroom residence sits on a generous 10,769 square foot lot, offering the perfect blend of comfort, style, and high-end finishes throughout. As you enter through the welcoming front porch, you’re greeted by porcelain floors and a spacious, open-concept design. The light-filled living and dining areas provide breathtaking views of the resort-style pool and oversized lanai, creating the ideal setting for entertaining or relaxation. The chef’s kitchen is the heart of the home, boasting an oversized island with quartz countertops, custom cabinetry, and Bosch appliances, making it a culinary dream come true. Beyond the main living spaces, this home offers a dedicated office and a generously-sized playroom with a pool table, perfect for families or hosting. The luxurious primary suite, with direct access to the pool and backyard, features a spa-like ensuite bathroom, complete with floating vanities, luxury Delta fixtures, and an oversized shower. Step outside and find yourself in a private outdoor oasis, designed for year-round enjoyment. The fully equipped outdoor kitchen features a 36’ gas grill, wet bar, mini refrigerator and seating in the outdoor dining area, all overlooking the 14’x28’ pool. With smart lighting, a prewired outdoor sound system, and garden lights, this backyard is ready for evening entertaining or peaceful poolside afternoons. This home is loaded with modern upgrades, including LED lights with dimmers, a Nest smart thermostat, a 5-ton A/C unit, a smart water heater, and 24”x48” porcelain tiles throughout. Your peace of mind is ensured with a smart home security system featuring three alarm keypads and pre-installed outdoor cameras. Located just minutes from the vibrant Downtown Baldwin Park, Rollins College, and a wealth of shopping and dining options, this home is perfectly situated to for convenience and luxury. Whether you’re looking to settle in a serene neighborhood or seeking a high-end investment opportunity, this nationally recognized home offers it all. Don’t miss your chance to own a piece of the American Dream—schedule your private tour today.

2015 Summerfield Road, Winter Park

$1,798,000

4 Beds ⋅ 3.5 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

**Stunning New Construction in Lake Killarney Shores** Welcome to your dream home in the highly sought-after Lake Killarney Shores! This exquisite 4-bedroom, 3.5-bathroom residence boasts a spacious 2,857 square feet of luxurious living space, complete with a charming casita featuring its own private bathroom. Enjoy the ultimate outdoor lifestyle with a refreshing saltwater pool, sun bench, and an outdoor kitchen perfect for entertaining. As you enter through the grand solid wood front door, you are greeted by luxury wood flooring in Captiva Maple and an abundance of natural light that fills the open-concept living areas. The home features 11-foot ceilings on the first floor, level 5 drywall, and 7.5-inch baseboards, creating an elegant and airy atmosphere. The gourmet kitchen is a chef's delight, showcasing a stunning marble backsplash, quartz countertops with a waterfall feature, and top-of-the-line Electrolux appliances, including a refrigerator, dishwasher, microwave, and a custom pot filler. A wine cooler adds a touch of sophistication, while the custom electric fireplace by Dimplex provides warmth and ambiance. Step outside to your private oasis, where a beautifully paved patio with seashell accents surrounds the saltwater pool. The summer kitchen is equipped with a gas grill, sink, refrigerator, and quartz countertops, making it ideal for alfresco dining. A privacy wall adorned with lush greenery ensures tranquility and seclusion from neighbors. Additional features include premium Pella windows with SunDefence for energy efficiency, a Dixie Pools tankless water heater, and two Daikin HVAC systems for optimal comfort. All door hardware is from Emtek and Richelieu, while stunning chandeliers and sconces from Light Style of Orlando and LBL Lighting add a touch of elegance throughout. With private lake access to Lake Killarney and proximity to Park Avenue's shopping and dining options, including Trader Joe's, this home offers the perfect blend of luxury and convenience. Don’t miss your chance to own this exceptional property—schedule your private tour today!

501 Country Club Drive, Winter Park

$1,650,000

4 Beds ⋅ 4 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Discover the perfect blend of elegance and functionality in this meticulously renovated single-story gem in one of the most sought-after neighborhoods in Winter Park. This chic transitional home, spanning 3,237 heated square feet, offers a seamless combination of contemporary design with a BRAND NEW ROOF, September ‘24. Inside, you'll find an open, airy layout with high-end finishes and smart touches throughout. The home features four spacious bedrooms, including two luxurious primary suites. The main suite boasts a spa-like bathroom with double vanities, striking granite countertop, an oversized frameless shower with dual shower heads, and a free-standing soaking tub. The second primary suite has a private entrance, washed brick accent wall, along with dual vanities and upgraded Kohler fixtures. At the heart of the home is a gourmet kitchen that’s truly a chef’s dream. It features a sleek granite island, European-style soft-close cabinetry, Jenn-Air appliances, including stainless steel gas cooktop with Zephyr hood and articulating pot filler, French door refrigerator, combo wall oven/microwave, and reverse osmosis system for purified water. Adjacent is the generous walk-in pantry with chrome shelving providing more than ample storage for all your culinary needs. Relax in the bright great room, where a soaring ceiling and stylish whitewashed brick wood burning fireplace creates a warm and welcoming ambiance. Sliding doors with electric shades seamlessly connect to an outdoor oasis featuring a paver patio, summer kitchen complete with a bar sink, built-in gas grill, hood, and refrigerator — perfect for al fresco dining and entertaining. Additional highlights include energy-efficient Vinyl Low E glass windows and doors, a Rennai tankless gas water heating system, programmable 15 SEER Carrier heat pump system, and security system. The indoor laundry room’s thoughtful design includes matching cabinetry, a Maytag washer, and matching gas dryer. The outdoor space features a wood-fenced yard for added privacy, and plenty of room for a pool. With no HOA and zoned for top-rated schools, this home is located within walking distance of Winter Park’s finest schools, Blue Jacket Park, East End Market, and more. Don’t wait to elevate your lifestyle with this stunning Winter Park property!

660 Arjay Way, Winter Park

$4,250,000

5 Beds ⋅ 5.5 Baths ⋅ Tuscany Terrace SubDv. ⋅ 32789 Zip Code

PROUDLY PRESENTING THE WINTER PARK VIA's NEWEST ADDITION TO THE LUXURY HOME MARKET ...BUILT BY M. LAHR HOMES! Prominently sited on a fantastic lot, this custom home has come together perfectly as a unique, awe-inspiring estate offering an unparalleled combination of function, elegance, and aesthetics. The home boasts a very well thought out design with finishes and features that showcase professional design planning at a very high level. There is even more detail, function, and quality than what is typically available in the Winter Park New Construction market. Offering a great combination of an expansive living area, large bedrooms, and unique spaces accented by three (3) feature fireplaces, the house feels nothing less than a resort. Expansive glass from the oversized doors and windows flood the home with natural light and create a dramatic exterior evening presentation. The entire main floor living area opens perfectly out to the large covered patio, back yard, and the pool/spa area making this entire area a beautiful four (4) season extension of the interior living space. The floor plan features a private ground floor primary suite, four (4) additional large bedrooms (all with private baths and walk-in closets), and numerous sitting areas/loft/dining spaces that can be utilized to suit multiple needs! Please see floor plans attached and CLICK ON TOUR LINK FOR A COMPREHENSIVE VIDEO WALK THROUGH . You will not find a better opportunity to secure a highly detailed, unique, luxury home in the WP area that offers the feel, presentation, and function of 1229 Via Del Mar. Located in the desirable Winter Park Via's location in top rated Dommerich/Winter Park School District and minutes to WP Raquet Club, Park Ave. Shopping, Winter Park Village, DT Orlando, Advent Health, ORMC and more. An exquisite Luxury Estate in one of Central Florida's most dynamic areas!

1229 Via Del Mar, Winter Park

$1,995,000

Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Hard to find frontage on Fairbanks Avenue in desirable Winter Park. This lot and business offer a prime location being on a corner lot just one mile from Park Avenue and Rollins College. 34,000 plus vehicles pass by this location daily! Building features concrete block construction and stucco exteiror. It has 2 service bays with energy efficient doors and automatic openers. The roof was replaced in 2017 with energy efficient 6-inch roof laminate. Interior is fully air conditioned by 2 units. There is a large storage room in the rear, separate from the office. Property has a top of the line video surveillance system inside and out. Property is fenced with a 4 foot metal fence and 2 rolling gates.

1931 W Fairbanks Avenue, Winter Park

$1,150,000

4 Beds ⋅ 2.5 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Welcome to this stunning 4-bedroom, 2.5-bathroom POOL home with a NEW ROOF, offering a perfect blend of modern luxury and functionality, located in the desirable Sylvan Lake Shores neighborhood of Winter Park. The property boasts a thoughtfully designed open floor plan with dark oak wood floors and recessed lighting throughout, creating a bright and inviting atmosphere. The gourmet kitchen is a standout feature, equipped with a gas stainless steel range, pot filler, stainless steel hood, quartz countertops, a farmhouse-style sink, and a large island with seating—perfect for casual dining or entertaining guests. French doors open from the kitchen and living areas to a covered, paver lanai, where you’ll find an outdoor summer kitchen complete with a fridge, gas cooktop, grill with rotisserie feature, and vented hood. The outdoor living space also includes a TV, offering the ideal setup for year-round entertaining. Step into your private backyard oasis, fully fenced and surrounded by lush vegetation, a waterfall, and a water feature. The paver, heated pool provides a relaxing escape, while the expansive lanai runs the width of the home and features seating, dining, and lounge areas. Whether hosting a poolside gathering or enjoying a quiet evening, this backyard offers unparalleled privacy and tranquility. The home’s split floor plan ensures privacy for all, with the primary bedroom and two secondary bedrooms featuring French doors that open to their own private retreats. The primary suite has been fully remodeled and includes a spacious walk-in closet with built-ins and a safe, as well as private access to the pool deck. The luxurious en-suite bathroom boasts a dual-sink vanity, a throne room, and a large shower with a wand feature, creating a spa-like experience. Additional features include a Nest thermostat, Ring security system, a laundry room with a utility sink, and a 2-car garage. The office, which can be used as a fourth bedroom, offers built-in cabinets, shelves, and a closet, providing ample storage. The home also comes with a gas hot water heater and a new metal roof, ensuring energy efficiency and durability. Located just minutes from Winter Park's vibrant shopping, dining, and top-rated schools, this home offers a rare opportunity to enjoy modern living in one of Central Florida’s most sought-after areas. Schedule your private showing today and discover the perfect blend of comfort, luxury, and outdoor living!

345 Sylvan Boulevard, Winter Park

$4,595,000

5 Beds ⋅ 5.5 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code

Experience the pinnacle of luxury living in this stunning five-bedroom estate situated on an oversized 120-foot wide lot on a tranquil and premier Vias brick street. This elegant Tuscan Mediterranean enjoys over 5,600 square foot of living space offering an exceptional blend of elegance and comfort, ideal for both intimate gatherings as well as grand entertaining. As you step through the foyer, you are welcomed to the open formal living and dining areas, with a wall of glass straight ahead capturing grand views of the sparkling pool and beautifully landscaped backyard. The heart of the home is the spacious, chef-inspired island kitchen, featuring top-of-the-line appliances, a hidden walk-in pantry, and a 12-by-12 breakfast nook. This space seamlessly connects to the main casual gathering room and additional flex/media room beyond, making it perfect for hosting large gatherings. The gathering area is anchored by gorgeous built-ins and a modern linear fireplace, with large sliding glass doors that open to the expansive covered lanai, blending indoor and outdoor living. The flex/media room is bathed in natural light, thanks to oversized picture windows that frame lush backyard/pool views as well. It also features a glass-enclosed, temperature-controlled wine room and a powder/pool bath that leads to an outdoor shower. On the opposite side of the main level, there is a stately office/library, with its wall of built-ins, providing a peaceful workspace with full views of the front courtyard. The grand primary suite is a true retreat, the gracious space includes a sitting area, a spa-like primary bath, two ample walk-in closets, and access to a private, trellis-covered courtyard with a fountain. The first floor also includes a hidden full guest suite with an ensuite bath. Upstairs, you'll find a large loft/bonus room with built-ins, along with three additional bedroom suites, each boasting ensuite baths and walk-in closets. The private backyard is an oasis, featuring a beautiful, tropical pool with a waterfall feature, a relaxing spa and lush mature grounds. The covered lanai extends your living space outdoors, complete with a seating/lounging area with a gas fireplace and TV, a summer kitchen, and room for alfresco dining. A split three-car garage and a picturesque brick paver driveway enhance the home's curb appeal. Situated in the highly sought-after The Vias neighborhood of Winter Park, 1231 Via Salerno offers the perfect blend of privacy and convenience, just minutes from upscale dining and shopping on Park Avenue, the Winter Park Racquet Club, Interlachen Country Club, and top-rated schools. This is a rare opportunity to own a truly exceptional home in one of Winter Park's most desirable locations.

1231 Via Salerno, Winter Park

$1,650,000

4 Beds ⋅ 3.5 Baths ⋅ Town Of Winter Park SubDv. ⋅ 32789 Zip Code

Immerse yourself in the serenity this modern boutique home offers in the heart of Winter Park, FL. Walking up you are greeted by an adorable front patio enticing you to enjoy your favorite beverage amongst the lush landscape. Once inside the arched entry door you will be transported to an open floor plan with lots of natural light adorned with oversized windows, showcasing flora at every turn, beautiful lighting, and nature-inspired tile up against a darker pallet of appliances and cabinetry. The kitchen is complete with Z Line gas range/oven and hood along with an oversized sink and Z Line dishwasher and refrigerator. The Kitchen also features ample built-in pantry cabinets. This home offers a comfy dining area where additional dining is incorporated in the kitchen island design. The great room opens up to a spacious outdoor patio area and luxurious pool encased in a tunnel of bamboo. An outdoor shower and pool bath are also featured in this area. Back inside as you roll upstairs you will have a close up view of the beautiful foyer chandelier and be invited by double entry doors into the master bedroom, bathroom and walk-in closet. Upstairs there are also 3 more bedrooms and 2 full bathrooms located down a brightly lit hallway. 840 W Comstock is nestled in the popular downtown Winter Park area where shopping and restaurants are just a short stroll down the street and is zoned for the top-notch public schools, Audubon Park K-8 and Winter Park High School. Schedule your visit today and fall in love with this dreamy home!

840 W. Comstock Ave., Winter Park

$1,099,000

4 Beds ⋅ 2.5 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code

REINTRODUCING 1718 DEMETREE DRIVE … YOUR FOREVER HOME IN WINTER PARK! This beautiful 4 bedroom, 2.5 bath, single story traditional brick home is located in the desirable WATERBRIDGE neighborhood. Waterbridge is known for showcasing homes with excellent curbside appeal, manicured lawns and landscape, huge oak trees lining the streets and well-maintained sidewalks while fostering a sense of safety and community. Entering the home, through the newly painted double doors, you are greeted by the warm and welcoming formal living and dining room. The stunning kitchen features solid wood cabinets, stainless steel appliances, granite countertops, and counter seating. This space is brightened by a charming window over the kitchen sink and lovely bay window in the dining nook that opens to the cozy family room highlighted with an impressive brick fireplace that is sure to impress! Ceiling fans, engineered hardwood floors, porcelain, and travertine throughout the main living areas. Two car side entrance garage leads to the large laundry room with utility sink and plenty of storage space. Expansive master bedroom, bathroom with walk-in shower, large custom closet and double doors leading to the outdoor living space. Three additional bedrooms with functional closet space are easily accessible to the hallway/pool bath. The NEWLY RESURFACED SALTWATER POOL and above ground spa are set within a generous outdoor area, complete with a screened enclosure overlooking a fully fenced backyard, privacy hedge and flourishing lemon trees. Excellent schools … Brookshire Elementary, Glenridge Middle and Winter Park High close by. Convenient to Baldwin Park, to enjoy the lake, dog park, restaurants and shopping. Easy access to downtown Orlando and Park Ave Winter Park. Don’t miss your chance to make this incredible home your own! Call today to schedule your private showing!

1718 Demetree Drive, Winter Park

$3,450,000

3 Beds ⋅ 3.5 Baths ⋅ Residences SubDv. ⋅ 32789 Zip Code

Luxury, location, and lifestyle beautifully come together at The Residences, one of downtown Winter Park’s premier condominium communities. The building offers 24-hour concierge service, a rooftop pool & spa, and an ideal location just one block from Park Avenue. This spacious 3,355 square-foot lock & leave home boasts stunning views of Winter Park and includes multiple balconies for enjoying the scenery. The single-story condo is equipped with a private elevator and secure access. A grand entry hall leads to an open-concept great room with sliding doors to the primary balcony and the dining room. The adjacent kitchen has Viking and Sub-Zero stainless appliances, along with a large eating area. The floorplan is well laid out with a 3-way split plan. The primary suite is spacious and refined with a private balcony, oversized custom closet, and bathroom with jacuzzi tub, separate shower, dual vanities, and 2 lavatories. The other wing has a powder room, two additional en-suite bedrooms, a dedicated office/flex space, and a laundry room. Classic interior design with hardwood floors throughout the home, tall ceilings, crown molding, chair rail, and French doors. Underground secured parking includes 2 reserved spots, and this unit comes with a separate storage space. The Residences includes 24-7 concierge services, a rooftop pool & spa with a grill and kitchenette that can be reserved for private events, maintenance services, and various sitting and meeting spaces. Conveniently located next to The Alfond Inn, with its newest addition of The Spa at The Alfond Inn, Winter Park’s newest sought-after spa destination. The Residences provides all the conveniences of a private luxury resort... without ever having to leave your home.

300 S Interlachen Avenue Unit 403, Winter Park

$1,750,000

4 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code

Crafted by a family-owned, up-and-coming builder known for their dedication to design and functionality, this newly constructed contemporary home in the heart of Winter Park, Florida, is a testament to quality and craftsmanship. Every detail in this 3,620-square-foot residence reflects a commitment to modern living, with warm, inviting finishes that create a perfect blend of style and comfort. Featuring 4 bedrooms and 4 full bathrooms, including a versatile first-floor bedroom that doubles as an office, this home is nestled in a vibrant, rapidly growing neighborhood. You’re just a short stroll from AdventHealth Hospital, Ward Park, and the scenic Cady Way Trail. The renowned Park Avenue, with its boutique shops and gourmet dining, is only 5 minutes away, offering the best of Winter Park living. Step inside to an open floor plan that exudes modern luxury. The first-floor features soaring 10-foot ceilings, custom steel stairs with solid oak treads, and exquisite wood flooring throughout. The heart of the home is the expansive kitchen, complete with two large islands, functional storage, and a hidden butler’s pantry, making it a chef’s dream. Adjacent to the kitchen is a spacious family room with 21-foot ceilings, flooded with natural light from large, towering windows. A striking custom concrete fireplace extends from floor to the ceiling, creating a focal point that blends style with comfort. The primary suite on the second floor is a private oasis, featuring a cozy nook perfect for a reading corner or work desk. The ensuite bathroom is adorned with marble floors and shower, a custom floating vanity, and a freestanding tub, all complemented by gold fixtures. The walk-in closet is a masterpiece of design, built-in shelving, hanging rods, and natural light from a well-placed window. Outdoor living is just as impressive with a large .27-acre corner lot. The backyard is your private retreat, featuring a brand-new saltwater pool with a sun shelf for lounging and a pristine marble deck that extends into the covered lanai. Entertain or unwind in this serene space, accessible through grand 12x8-foot sliding glass doors that blend indoor and outdoor living seamlessly. Located within minutes of highly rated schools, Rollins College, and premier medical facilities, this home is for families and professionals alike. the convenience of nearby parks, trails, and the cultural charm of Park Avenue, all while residing in a neighborhood that the luxury of Winter Park’s finest without the premium zip code.

2025 Loch Berry Road, Winter Park

$1,395,000

3 Beds ⋅ 2.5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Experience the charm and convenience of Winter Park living in this beautifully updated one-story pool home, perfectly located just minutes from the vibrant Park Avenue. Nestled on the desirable Palmer Avenue, between the two Alabama Drives, this 3-bedroom, 2.5- bath residence offers 2,550 SF of thoughtfully designed living space. The home underwent a remarkable renovation in 2012, which included an expansive Primary Suite. Recent upgrades only enhance its appeal, with a NEW ROOF and new gutter downspouts installed in August 2024. Additional improvements include a new beverage refrigerator (August 2024), a newer full-size refrigerator (2021), and a newer hot water heater (2020). This property is a true reflection of pride in ownership and modern comfort. The front exterior features an oversized brick paver driveway with ample guest parking and a 2-car garage. Inside, enjoy timeless hardwood floors throughout the bedrooms, and living and dining rooms. The fabulous sunroom is flooded with abundant natural light, showcasing views of the expansive pool area and fully-fenced backyard, including a paver deck that offers space for lounging and entertaining, an aluminum pergola, and an air-conditioned detached, workshop/storage building. Off the foyer, a hallway leads to two bedrooms with custom built-in closets, and a full bathroom with convenient access to the pool and backyard. At the end of the hallway, you'll find the Primary Suite, where 2 bedrooms and a bath were combined to create a large and impressive retreat. The expansive bedroom features a cozy sitting area by the bay windows. The primary bathroom includes a generous soaking tub beneath a sunlit window, a separate glass-enclosed shower, a linen closet, plus a custom walk-in closet that stretches an impressive 12 feet deep. Storage space is abundant with multiple linen and hall closets along with built-in shelves and storage cabinets in the garage. The laundry room is located behind the Kitchen, wrapped in cabinets and countertops, includes a NEW washer and dryer, and a NEW beverage refrigerator. The powder bath is conveniently located off the Kitchen for your guests. This home is in a prime location just minutes from a variety of shops, restaurants, and grocery stores. Within a 1.5-mile radius of 1011 Palmer Ave., you'll find Park Ave, Winter Park Village, Whole Foods, Sprouts, Publix, the YMCA, Phelps Park, Walgreens, and Advent Health—all offering unparalleled convenience. This location truly has it all! * Please ask for a floor plan, list of improvements, and click on the Matterport link for a virtual tour!

1011 Palmer Avenue, Winter Park

$1,795,000

4 Beds ⋅ 3.5 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code

Welcome to this stunning four-bedroom, three-and-a-half-bath contemporary home, meticulously crafted by Rex-Tibbs in 2015, located on a quintessential Winter Park brick street. Unique opportunity as home has been barely lived in since built and literally still shows like a brand-new home that's been extremely well maintained by Total Care Management & Signature Landscaping Contractors over the years. With walls of glass and a spacious, open modern floor plan, this home is perfect for both entertaining and everyday living. The spacious living and dining area is filled with natural light streaming through large windows, creating a warm and inviting atmosphere. The open kitchen, overlooking the family room with a cozy fireplace, is a chef's dream, featuring a large island with an under-counter wine fridge, a Thermador six-burner gas range, and a Thermador refrigerator. Glass sliders in the family room provide a seamless view of the expansive backyard and the sparkling pool. The private primary suite offers a tranquil retreat with glass sliders that open to the covered lanai and pool area. The ensuite bath is luxurious, and the suite includes two separate walk-in closets. Upstairs, the second floor offers a spacious bonus room, ideal for a game room or additional family space, alongside three generously sized bedrooms with large closets and two full baths. Enjoy the expansive, fenced backyard featuring a modern pool surrounded by a travertine pool deck, offering a clean and sophisticated aesthetic. The covered lanai provides a perfect space for relaxation and entertainment, offering shade from the sun and shelter from the rain, all while allowing you to enjoy the serene view of the outdoor oasis. Nestled among newer homes, this property is within walking distance to downtown Winter Park, Park Avenue's boutique shops, restaurants, Central Park, the Winter Park Farmer's Market, and more. Situated in a top-rated school district and with easy access to major roadways, this home offers an effortless commute to downtown Orlando. Enjoy the perfect blend of elegance, comfort, and convenience in this beautiful Winter Park home.

643 Pansy Avenue, Winter Park

$1,595,000

4 Beds ⋅ 3 Baths ⋅ Penn Place SubDv. ⋅ 32789 Zip Code

Welcome to this stunning two-story townhome, ideally situated on a picturesque brick street in Winter Park's exclusive Penn Place community. As an end unit, this residence offers an abundance of natural light and privacy, with impeccable design and high-quality finishes throughout. Step inside and be greeted by gorgeous solid hickory wood floors that flow throughout the main living areas, primary suite, and family room. The expansive great room, dining area, and chef's kitchen create a seamless open floor plan perfect for entertaining or hosting large gatherings. The chef's kitchen features marble countertops, a large island, a Wolf six-burner gas range, a built-in oven and microwave, Sub-Zero refrigeration, and a spacious walk-in pantry. A Crestron "Smart Home" system allows whole home control for audio, security and lighting. A charming bar area and under-counter beverage fridge completes the main living area. Tall ceilings (11'4") and large windows enhance the open and airy feel, while French doors lead to a serene blue-stone private courtyard with a natural gas hookup for your grill, perfect for al fresco dining and outdoor enjoyment. A fourth bedroom which can serve as an office/den or guest suite completes the first floor. A private in-unit elevator and solid wood custom stairs provide easy access to the second floor. Upstairs, discover the grand primary suite, a true retreat with two expansive walk-in closets and a luxurious spa bath featuring a soaking tub, a walk-in shower, and dual vanities. A spacious family room with a wet bar and an under-counter wine fridge provides a perfect space for relaxation or entertaining. Two additional bedrooms, each with walk-in closets, complete the second floor. A rear-entry attached two-car garage with an epoxy floor provides convenience and extra storage. Built with exceptional quality, Penn Place offers peace of mind with poured solid exterior walls for soundproofing, spray foam icynene insulation, insulated interior walls, a fire sprinkler system, professional landscaping by Signature Landscape, and elegant copper natural gas lanterns. Enjoy the ultimate Winter Park lifestyle with a short walk or bike ride to vibrant Park Avenue, Rollins College, the Winter Park Farmers Market, and a variety of restaurants and shopping. Experience the perfect blend of the lock and leave lifestyle, luxury, comfort, and location in this beautiful townhome.

1009 S Pennsylvania Avenue, Winter Park

$2,199,999

6 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code

**Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the pinnacle of sophisticated living. Boasting 6 total bedrooms, 4 bathrooms, including a detached 2-bedroom guest house, this property seamlessly blends modern amenities with timeless charm. As you step through the grand entrance, you are immediately greeted by a stunning foyer adorned with pristine travertine flooring, setting the tone for the elegance that lies ahead. The open floor plan, accentuated by soaring high ceilings, creates an inviting atmosphere perfect for both lavish entertaining and tranquil family living. The heart of the home, the gourmet kitchen, is a chef's dream come true. Featuring breathtaking quartz countertops, top-of-the-line appliances, custom cabinetry, and an in-home wine cellar, this space is as functional as it is beautiful. Whether you're preparing a casual meal or hosting a grand dinner party, the adjacent dining room provides the ideal setting for every occasion. The master suite, located on the main floor, is a sanctuary of luxury and comfort. It boasts a walk-in closet and an opulent en-suite bathroom complete with a soaking tub, separate shower, and double vanities. The remaining bedrooms are located on the second floor, offering privacy and space for family or guests. Adding to the property's appeal is a completely separate 2-bedroom guest house, accessible via a private entrance. This guest suite includes a full kitchen, cozy living room, and its own laundry room, making it perfect for extended family, visitors, or even as a private home office. The flexibility and privacy this space offers are truly unmatched. Step outside to your own private paradise, where a sparkling pool awaits. The expansive screened-in lanai and ample outdoor space make this the ultimate setting for enjoying Florida's year-round sunshine. Whether you're hosting a summer barbecue or simply unwinding after a long day, this outdoor oasis provides the perfect backdrop. Located just minutes from the renowned Park Ave, this home is nestled in one of Winter Park's most coveted neighborhoods. Enjoy the convenience of being close to award-winning restaurants, boutique shopping, and upscale entertainment options. Living here isn't just about owning a home—it's about embracing a lifestyle of luxury and convenience. This stunning property offers the perfect blend of luxury, comfort, and location. Schedule your private showing today and discover what makes this Winter Park home truly exceptional.

1451 Lyndale Boulevard, Winter Park

$1,350,000

2 Beds ⋅ 2 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Walk to Park Avenue or take your boat on a sunset cruise through the canals! Experience upscale living in this fabulous condo with a DEEDED boat slip on the famous Winter Park Chain of Lakes. Located on the fifth floor, you will enjoy breathtaking tree-top lake views from this beautifully updated, one story unit covering almost 2100 square feet. The open layout features expansive living and dining areas that seamlessly transition to an outdoor screened-in porch. The stylish kitchen is well equipped with custom wood cabinets, granite countertops, stainless steel appliances and a center island with breakfast bar. The condo features a spacious guest suite with double closets, and a dramatic guest bath, complete with a custom designer vanity and a large walk-in shower. The generous owners suite offers a lounging area with radiant natural lighting. The spa-like bathroom includes custom vanities, soaking tub and a large walk in closet with built-ins. Additionally, features include automated blinds in the living room and an indoor laundry closet. The well maintained complex located on the shores of Lake Osceola offers underground parking, storage closet, and amenities such as pool and community laundry room. The property includes a deeded boat slip. Situated just steps away from vibrant Park Ave, residents will enjoy many fantastic restaurants, cafes, Museums, and Boat Tours, in addition to the convenience of the Sunrail/Amtrak station. The condo fee includes electricity, sewer, water, gas, maintenance, on-site manager, community pool, ground maintenance, roof, insurance, exterior and more.

311 E Morse Boulevard Unit 6-18, Winter Park

$4,150,000

3 Beds ⋅ 5.5 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Welcome to an exquisite three-bedroom, 5.5-bath plus office pool home in the heart of Winter Park. This stunning residence exudes elegance and sophistication, beginning with the stately double-front doors that open into a grand foyer, offering direct views of the beautiful pool and meticulously landscaped backyard. Step inside to discover a magnificent custom concrete and iron staircase that sets the tone for the remarkable craftsmanship throughout the home. A thoughtful floor plan is ideal for entertaining and comfortable living. The spacious open kitchen overlooks the family room and breakfast area, providing seamless access to the covered lanai. Outfitted with sleek European custom cabinetry by NEFF and double islands, the kitchen boasts an abundance of storage. The inviting family room features a stunning gas fireplace, coffered ceilings and a large custom bar complete with a wine refrigerator. The formal living and dining areas are enhanced by large picture windows that bathe the rooms in natural light, offering picturesque views of the lush grounds. The outdoor living space is nothing short of extraordinary, featuring a cozy outdoor living room with a gorgeous gas fireplace, a dining area and a built-in grill. Motorized screens open to reveal the pool and manicured backyard, creating an idyllic setting for relaxation and entertainment. The primary suite on the first floor is a sanctuary of luxury, offering two separate baths, each with its walk-in closet and access to the pool area. An elegant office or optional fourth bedroom and a secondary bedroom with an en-suite bath are also on the first floor. The second floor boasts a secondary primary suite with a spacious en-suite bath, featuring dual vanities, a spa-like tub and a glass shower. A brick paver-gated driveway leads to a motor court and a three-car attached garage, ensuring ample parking and privacy. This top-notch location is just a short distance from vibrant shopping and restaurants on Park Avenue and the iconic Winter Park Golf Course. Experience the epitome of luxury living in this remarkable Winter Park home, where every detail has been meticulously crafted for an unparalleled lifestyle.

850 Georgia Avenue, Winter Park

$4,350,000

5 Beds ⋅ 5.5 Baths ⋅ Tuscania SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Discover an exquisite Santa Barbara style Mediterranean that's undergone extensive renovations completed in 2024 to blend timeless elegance with modern luxury... This property is nestled in the heart of the prestigious Winter Park "Vias" - one of the area's most coveted locations, and only three houses from the WPRC... This stunning 5-bedroom (w/ the primary & guest suite both on 1st floor), 6-bath residence + office + bonus spaces, offers all the benefits of new construction without the wait or stress, boasting professionally designed interiors that exude sophistication and style… Step into the grand foyer, where a sweeping staircase and soaring ceilings welcome you into the heart of the home. The light-filled gathering room, adorned with a beautiful fireplace and is illuminated by three sets of French doors and expansive 2nd story windows as well, allowing natural light to cascade throughout the space. The gourmet kitchen is a chef's dream, featuring two striking waterfall islands, custom cabinetry, Caesarstone countertops, a 48-inch gas range, a Sub-Zero refrigerator, and a Meile coffee maker and steam oven. A secondary back staircase allows for easy access to the second floor from the kitchen with its four arched picture windows... The adjacent gathering room enjoys a two-story soaring ceiling with wall of glass flooding light in and included a fireplace, adjacent wine cellar and lanai - ideal space for entertainment… The private owner’s suite is a luxurious retreat, complete with a cozy sitting area, a stunning stone fireplace, vaulted ceilings, and large picture windows that frame serene views of the pool and manicured grounds. This suite also includes a custom walk-in closet/dressing room and a spa-like bath with a stand-alone soaking tub, dual vanities, and a beautifully appointed walk-in shower. The main level also features a front-facing office, perfect for working from home, and a private guest-suite with an ensuite bath and walk-in closet... Ascend the elegant, curved staircase to the second level, where a cozy loft and three additional bedrooms with ensuite baths, marble floors, and custom closets await. Additionally, the upstairs living encompasses a study alcove and a wonderful, oversized bonus/flex space... The outdoor living is equally impressive, with a covered lanai offering a serene spot for lounging and alfresco dining while overlooking the sparkling saltwater pool and wonderful, expansive back yard that is rare to find in Olde Winter Park homes. Note: The total AC area in this home per building plans is apprx 5,550SF... the main living area is ~4,500SF and lives/feels larger with spacious, open living areas that include 2-story ceilings, plus the additional ~1,000SF in a secluded, expansive bonus room that is a really cool, flex room for so many uses... The oversized lot (approximately 108-by-165 feet) provides ample space for outdoor activities and also benefits from a tranquil, very private setting… A covered drive through porte-cochere leads to the generous side-entry 3-car attached garage, adding to the convenience and grandeur of this stately property. This magnificent residence is just footsteps from the Winter Park Racquet Club and 5 minutes from Interlachen Country Club as well as the upscale shops and restaurants of Park Avenue… This is truly a unique opportunity to purchase a like-new, current design “like new” home offering an unparalleled lifestyle in one of Winter Park's most desirable addresses!!

1157 Tom Gurney Drive, Winter Park

$3,295,000

5 Beds ⋅ 5.5 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Under Construction. Welcome to this exquisite 5-bedroom, 5.5-bathroom home built by Lundev, perfectly situated in the highly sought-after Timberlane Shores neighborhood of Winter Park. Spanning 4,080 square feet, this property offers the ultimate blend of luxury and comfort. Thoughtfully designed for both entertaining and everyday living, this home features high-end finishes and top-quality craftsmanship throughout. Upon entering, you're greeted by a charming front porch with a cozy fireplace, setting the tone for the warmth and elegance that continues inside. This inviting outdoor space is perfect for relaxing with a morning coffee or enjoying cool evenings with friends and family. Step inside to find a spacious great room, ideal for gathering and entertaining, boasting ample natural light and a seamless flow to the rest of the home’s main living areas. The gourmet kitchen is a chef’s dream, boasting high-quality appliances, a wine cooler, refrigerator drawers, and a casual café area for everyday dining. The adjacent formal dining room offers a sophisticated space for hosting elegant dinner parties and holiday gatherings. These thoughtfully designed spaces ensure that every meal and event is special. The luxurious primary suite is conveniently located on the first floor, providing a tranquil retreat with easy access. It features a spa-like bathroom with double sinks, a soaking tub, a shower, a linen closet, and a large walk-in wardrobe for ample storage. Additionally, on the main floor you will also find a detached bedroom or office with an en-suite bathroom, built-in closet, and private entrance offering flexibility and making it ideal for guests or as a private workspace. Upstairs, you’ll find three aditional bedrooms, each featuring its own en-suite bathroom and walk-in closet, providing comfort and privacy for all occupants. A versatile loft/den area on the second floor adds extra living space, perfect for a home office, playroom, or relaxation area, catering to various lifestyle needs. The outdoor area is an entertainer's paradise, complete with a private pool & spa, a cabana with a pleasant fireplace, and a summer kitchen for alfresco dining and entertaining. Whether hosting a barbecue or enjoying a quiet afternoon by the pool, this space is designed for relaxation and enjoyment. With its great location, this home offers excellent proximity to Blue Jacket Park, Baldwin Park, and the vibrant Park Avenue, known for its entertainment options, shops, and restaurants. Experience luxury living in one of Winter Park's most coveted areas. Schedule your private tour today to see this stunning property in person!

1730 Winchester Drive, Winter Park

$1,039,000

3 Beds ⋅ 2 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

Enjoy Lake front living with all the fabulous Baldwin Park amenities! This charming 3 bedroom 2 bath home features an Open Plan with a Large Living & Dining Room along with with stunning views of Lake Spier. This move-in ready remodeled home boasts new flooring, fixtures and paint throughout. A 500sqft screened-in, tiled patio also makes this home for entertaining guests while enjoying water skiing, great bass fishing and other freshwater sports on this scenic, private, spring fed lake in the highly desired Winter Park School Zone. Roof will be replaced prior to closing, with buyer choosing color of shingles!

1875 Lake Spier Drive, Winter Park

$1,349,000

6 Beds ⋅ 4 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Location Location Location. WINTER PARK. Built in 2021 and upgraded this year. This Meritage Homes Wimberley 11 model sits on a premium lot that backs onto conservation and is next to the playground and fishing dock. This stunning 6 bed 4 bath home is perfect for the family and multi generational living. There is so much space surrounded by comfort and style. When you enter you are greeted by the open concept floor plan. The foyer passes the formal dining room to reveal the expansive kitchen and living area. The absolutely wonderful oversized pool and deck are welcoming through the glass siding doors along the rear wall. Past the pool is the lush greenery of the conservation area that is the buffer to Lake Howell. The pool is a saltwater pool so no red eyes from too much chlorine. There is bathroom and shower access from the pool. The screen enclosure has extra-large panels to give the best view of the sunsets and foliage. The primary bedroom is located downstairs off the lounge while the other 5 bedrooms are split 3 and 2 either side of the upstairs lounge and media room. There formal dining room can easily hold a table for 12 or more for those special occasions The home has new vinyl planking throughout and tastefully customized molding on select walls. The upstairs lounge has its own wet bar and the large media room is ideal for movie night. The home has a water softener, a solar system for low energy bills and a six-zone built in stereo system. Inside laundry. Ample parking inside the garage and driveway. Located in the Winter Park gated Hawks Crest community residents enjoy exclusive access to a community pool, fitness center, dog park, playground also includes access to Lake Howell. Put in your paddle board, kayak or just enjoy the wonderful sunsets from the fishing dock.

1269 Wading Waters Circle, Winter Park

$1,178,000

4 Beds ⋅ 3.5 Baths ⋅ Bear Gully Pointe SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Welcome to Bear Gully Pointe! Nestled behind this small,gated community of 60 homes, you’ll find this exclusive luxury updated home that offers an Entertainer’s paradise. Entryway welcomes you showcasing exquisite architectural details with soaring 12 +foot ceilings, expansive windows and abundant sky lights throughout the home for infusing natural light. This entertainment friendly 4BR/3.5BA home offers MEGA lifestyle and oversized luxury with its’ split floorplan flow. The combined Formal Living and dining room overlooks the outdoor oasis and is designed to host elegant celebrations. Enjoy the stylish built in wine cellar/rack that enhances the formal dining experience. The home’s stunning focus is a resort style saltwater pool beneath a newly added screen enclosure. This patio showcases the heated pool with natural gas fire, waterfalls and color LED lighting. The summer kitchen has a built-in grill, fridge, open top cooler, swivel tv, wet sink and a comfy bar that seats 4.Multiple seating areas are arranged under the tongue& groove ceiling & easily accommodates 50+ guests. The interior atmosphere of elegance is captured with the state-of-the-art kitchen featuring solid wood cabinetry/quartizite/granite & Executive GE Monogram natural gas appliances. Note the central island is double sided with pull out drawers from both sides. The above view offers an amazing custom woodwork artistic ceiling with a deco feel while the skylights provide natural lighting. Culinary refinement is combined with the everyday usability with a eat -at bar while encompassing the family room and casual dining space. The butler pantry complete with wine cooler & icemaker is alongside the laundry room with two large pantries and adjacent to the kitchen. The family room centers around the dramatic custom-built stone wall with cabinets and gas inset fireplace showcasing a mounted digital TV (that stays).Luxury wainscot accented walls add exceptional charm. The large Owner’s Retreat has access to the lanai with a comfy oversized bath featuring soaker/jet tub, shower and twin walk in closets.Privacy is offered with the home’s split floor plan that includes 3 spacious bedrooms and 2 baths on the opposite side of the home.The convenient intercom system facilitates communication throughout the home from the front door to each living area. Venture upstairs to the rare additional family loft complete with wet bar and wine fridge. This room offers walk-in access to the attic for additional storage space complete with an automatic vent fan to keep storage temperatures cooler. The 3-car garage has newly installed garage doors rated for hurricane 5 force winds and locking devices complete with battery backup. Custom built in ceiling wall racks maximize the garage storage capability. Home is pre-wired to the electrical panel for a portable generator and plug ready. State of the art “smart” security system stays. Exterior features: Wi-fi activated irrigation system, 10+foot hedges & 50 year poly fence. Two zone HVACs are 2023 & 2024 installed. Every detail from the landscaped exterior symmetry to the precision of interior trim work and premium materials offers you a unique blend of designer sophistication that aligns perfection for your NEW home. BEAR GULLY POINTE amenities include a tennis court & playground with nominal annual fees. Indulge yourself with value and oversized luxury! Convenient to Trinity Prep , UCF, Orl. & Sanford Airports & easy access to SR417.

2884 Old Castle Drive, Winter Park

$1,250,000

4 Beds ⋅ 4 Baths ⋅ Elizabeth Heights Sub SubDv. ⋅ 32789 Zip Code

Welcome to an architectural gem in the heart of Winter Park—a newly built masterpiece that epitomizes modern luxury and state of the art design. Perfectly situated just a mile from the upscale Park Avenue and only 2.5 miles from the vibrant downtown Orlando, this home offers the ideal combination of tranquility and city convenience, free from the hassles of I-4 traffic. From the moment you arrive, you’ll be captivated by the clean lines and minimalist exterior framed by lush landscaping and a pristine lawn. Step inside to an expansive open floor plan where sleek design meets luxurious finishes. The living, dining, and kitchen areas seamlessly blend together, creating a bright and inviting atmosphere enhanced by natural light pouring in through large windows. The gourmet kitchen is a chef's dream, featuring high-end stainless steel appliances, custom cabinetry, a grand island with a stunning waterfall-edge quartz countertop and seating, elegant pendant lighting, and a stylish backsplash that adds a touch of sophistication to the contemporary design. This home offers four beautifully appointed bedrooms and four luxurious bathrooms. The versatile guest bedroom suite on the first floor provides convenience and privacy, while the second floor features three additional bedroom suites, including a spacious primary suite. The primary bath is a personal retreat, complete with double vanities, a separate soaking tub, and a walk-in shower, offering a spa-like experience. Enjoy the Florida lifestyle to the fullest in the private, fenced backyard, ideal for entertaining or relaxing, and take advantage of the covered lanai with a summer kitchen. Additional highlights include a spacious two-car garage, ample storage throughout including a large walk-in closet in the primary suite - equipped with a luxurious closet system, and designer LED lighting throughout. With top-rated schools nearby and a location in one of Central Florida’s most desirable neighborhoods, this home is perfect for families or anyone seeking a modern, luxurious living experience. Don’t miss this rare opportunity to own a one-of-a-kind residence in Winter Park!

1320 Orchid Avenue, Winter Park

$1,050,000

2 Beds ⋅ 1.5 Baths ⋅ Aloma SubDv. ⋅ 32792 Zip Code

This Winter Park investment opportunity is prime for Developers, Builders, & Investors for redevelopment. The Hawick Lane property currently has a single family house that is Tenant-Occupied and income producing. It is believed that the highest and best use of this property would be to tear down the current house and redevelop the property into four (4) detached single family homes in a courtyard style development or a lot split into three (3) fee simple single family lots (50’ wide). The total land area is approximately 19,698sf. (150ft street frontage by 140ft lot depth).

2260 Hawick Lane, Winter Park

$1,575,000

7 Beds ⋅ 5 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code

One or more photo(s) has been virtually staged. PRICE REDUCED! This stunning lakefront estate features 7 bedrooms and 5 full baths, all within a spacious 5,000+ square foot "Del Rio" open floor plan. As a certified 100% Energy Star home, it boasts top-of-the-line appliances in the kitchen, wet bar, and butler's pantry, complemented by granite countertops. The home offers two master suites—one on each level—each featuring plush carpeting, porcelain tile, soaking tubs, glass showers, and ample his-and-hers vanity space. The main living areas are adorned with wall-to-wall tile flooring, and the bedrooms feature new carpet through most. Additional highlights include plantation shutters, freshly painted, fully insulated attic for energy efficiency, a gorgeous wooden staircase, 7-inch baseboards, Brand new dual HVAC units, internal pest control ports, a home theater room with raised flooring, and updated lighting throughout. Accordion doors lead to a vast brick paver patio with a covered lanai, where you can enjoy fruit trees in abundance and breathtaking sunsets over Garden Lake. Only you, as a lucky homeowner will be able to enjoy a little rest and relaxation on your boat! The 1 ACRE water front oversized lot offers plenty of room to add a basketball court and pool. The property includes a three-car garage (with one tandem space) extra storage racks included and a large extended driveway, providing ample parking for family and guests. This home exudes luxury, style, and comfort, all conveniently located near Winter Park, Oviedo, UCF, and top-rated schools like Trinity Prep, with shopping and dining just a short distance away.

1460 Via Sangro Place, Winter Park

$1,999,999

4 Beds ⋅ 4 Baths ⋅ Windsong Elizabeths Walk SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. WINDSONG - Welcome to an Unparalleled Mediterranean Retreat in Exclusive Winter Park! Step into this incomparable custom home, boasting just under 4,000 square feet of luxurious living space, and discover a haven of ultimate privacy. Nestled on a serene cul-de-sac, this meticulously designed residence promises a lifestyle of tranquility and sophistication. As you enter through the grand wrought iron door, you are greeted by an impressive foyer adorned with soaring high ceilings, elegant wood beams, and graceful travertine flooring that extends throughout the home. The newly painted interior adds a fresh, contemporary touch. The first-floor primary bedroom retreat exudes luxury with its gleaming hardwood floors, sparkling light fixtures, and a lavish en-suite bathroom featuring a walk-in shower and a spacious walk-in closet. The closet is a true masterpiece, with backlit shelves to showcase your prized possessions and a large island perfect for displaying watches, jewelry, and heirlooms. Designed for both entertaining and everyday living, the open floor plan offers a grand view of the spacious first floor, where magnificent high ceilings create a palatial ambiance. The living area features a built-in wall unit with lights, while the dining room boasts a beautiful tray lighted ceiling, adding a touch of sophistication to every meal. At the heart of this home is the gourmet kitchen, a culinary masterpiece equipped with rare Brazilian quartzite countertops, JennAir appliances, a wine refrigerator, a built-in cutting board, hidden spice racks, and a gas cooktop on the island. This kitchen is not only functional but also perfect for engaging in conversation with family and guests while preparing meals. Embrace the ultimate indoor-outdoor lifestyle with kitchen windows that open to the pool/bar area, creating a seamless transition to the picturesque courtyard oasis. Here, you'll find a heated saltwater pool with a spa, a summer kitchen with a retractable awning. Additional features include a large butler pantry with extra storage space, an adjacent laundry room with built-ins and hanging space, and convenient access to the garage. The first floor also houses a wine room and a spacious guest room with hardwood floors and a lavish full bathroom with floor-to-ceiling travertine tile. Ascend the wrought iron railing and hardwood stairs, adorned with imported decorative tile risers, to the second floor, where you'll find two additional bedrooms, each with separate entrances to a large tiled balcony overlooking the courtyard. A Jack and Jill bathroom with a shower completes the upstairs living space. This exceptional home also includes a water softener system for the entire house, ensuring comfort and convenience in every corner. Experience resort-style living at its finest in this architectural masterpiece, located in the highly sought-after Windsong community in Winter Park. Make this exquisite sanctuary your own and indulge in the epitome of luxury living.

1764 Elizabeths Walk, Winter Park

$1,495,000

5 Beds ⋅ 3.5 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

From the boutique address at 433 Carolina Ave, take a stroll down to historic Hannibal Square or to the New England gourmet corridor. On Saturday's mornings, have your breakfast at the Winter Park farmers market and by sunset, enjoy Park Avenue or Winter Park Village. Back home, feel comfortable, extremely comfortable in this casual-chic custom designed home. After a welcoming foyer, a kitchen-bar opens to a large and bright great room fitting dining and living areas. It continues to the back covered veranda and back yard. Still on the first floor, you have a guest suite and an office, conveniently located by the entry door. Up the stairs, a large family room, capable of gathering all the family. In the large master suite balcony, you may have your first coffee in the morning, listening to the early birds. The two other rooms also have balconies to the front of the house. All rooms have closets with shelves, to accommodate your needs. Enjoy finishes like wood floors, large mirrors in bathrooms, quartz counters, crown molding, wide windows and more. This beautiful and modern home is ready for its new residents. It is absolutely gorgeous! Come and visit us. Welcome Home!

433 Carolina Avenue, Winter Park

$1,795,000

4 Beds ⋅ 3 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code

Discover serene lakefront living at its finest in this exquisite 4-bedroom 3 bath home at 279 Rippling Lane. Set against a picturesque backdrop, this property offers breathtaking views and direct lake access, complete with a covered boat dock for your aquatic adventures. The residence seamlessly blends modern luxury with timeless elegance, featuring spacious living areas, high-end finishes, and large windows that invite natural light and lake views indoors. Custom kitchen with quartz and wood counter tops, six burner pro style range. New roof in 2023 and upgraded electric panel 2018 and Air conditioner in 2020. A split floor plan with 3 bedrooms and 2 baths up front and a spacious primary bedroom and bath have vaulted ceilings and a large walk-in closet and overlooking the lake. Enjoy the tranquil ambiance of your private retreat while being just moments away from Winter Park’s vibrant dining, shopping, and cultural attractions. Don’t miss this rare opportunity to own a slice of paradise in one of Winter Park’s most sought-after locations.

279 Rippling Lane, Winter Park

$5,950,000

7 Beds ⋅ 6.5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Welcome to the epitome of refined luxury in the heart of Winter Park. This exceptional canal front estate home was completely redesigned and transformed by E2 Homes and finished in 2023 including a brand new boathouse just completed in 2024 with access to the Winter Park Chain of Lakes. Elegant features and impeccable craftsmanship throughout, boasting 6 bedrooms and 5.5 baths in the main home within its expansive almost 5000 square feet of thoughtfully laid out living space. Upon stepping inside, one immediately notices the meticulous attention to detail from the stunning white oak hardwood floors throughout to the impressive winding staircase. The open and spacious living room with its gorgeous wine wall that holds over 175 bottles of wine plus a separate wine refrigerator makes this the perfect place to host and entertain. The downstairs front office has tons of windows that allow natural light to flood in. The chef-inspired kitchen is a focal point, equipped with an abundance of custom solid-wood cabinets with plenty of storage, beautiful quartz countertops, a large island, and top-of-the-line Thermador SS appliances including a 6-burner natural gas stove, double ovens and even a warming drawer plus a Sub Zero refrigerator — ensuring that entertaining and meal prep are effortless. Overlooking this exceptional kitchen is the cozy family room as well as easy access to the dining area, all with a view of the impressive private backyard and pool area. This outdoor oasis includes a spacious covered lanai overlooking the Salt-water pool- the perfect place to relax and unwind with Family and Friends. Tucked away on the first floor is the elegant primary suite, featuring a spa-inspired bath with double sinks, custom cabinetry and exquisite tile work, along with a large walk-in shower with 2 shower heads, a luxurious soaking tub, and a water closet. This elegant owner’s retreat also features an expansive custom walk-in closet. Two guest suites are also on the first floor just off of the family room with a full bathroom with shower that they share as well as the impressive laundry room with storage cabinets and a utility sink. Upstairs, you'll find 3 more well-appointed ensuite bedrooms that are all generous in size with custom walk-in closets and meticulously appointed bathrooms. Detached guesthouse truly offers unparalleled comfort and privacy with 2 full bedrooms, a full bathroom with dual sinks and an accessible shower and a separate living room with full kitchen featuring a 5 burner gas range. Additional amenities include solid-core doors, wide base moldings, transferable Termite Bond, and 3 tankless water heaters. This remarkable home is flooded with natural light and ambiance, exuding a warm and cozy atmosphere. Plenty of parking for you and your guests with the front circular driveway and the gated porte cochere area with side entry into the home. Zoned for some of the best public schools in the area, including Winter Park High School, and conveniently located near Park Ave with its fine restaurants and shopping. Don't miss your chance to own this exquisite WINTER PARK PROPERTY with LAKE ACCESS and experience Florida living at its finest! Truly nothing like this on the market today! Welcome Home! **please note the guest house was originally a 3 car gargae that could easily be converted back. Owners have a sketch plan.**

1246 Alabama Drive, Winter Park

$1,299,900

3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Meticulously renovated condo walking distance from Park Avenue. This condo is located just blocks from restaurants and shopping in the heart of Winter Park's downtown. Renovations were done in December of 2023 and include all new French Oak hardwood flooring throughout, including in the three bedrooms. Also, paint, brand new LED adjustable hue can lights, stunning light fixtures, a brand new 81 gallon tank water heater, Google home smoke/carbon monoxide detectors throughout, Google Nest thermostat, and brand new LG washer and dryer. High end finishes were selected, including Pella windows, with Subzero, Wolf and Bosch kitchen appliances. This corner unit features it's own private entryway directly from a gated garage, and has two reserved indoor parking spaces. The 3 bedroom, 3 bathroom condo has an oversized master bedroom with two large walk-in closets, as well as another junior suite. All three bedrooms are spacious with very large walk-in closets.

100 S Virginia Avenue Unit 201, Winter Park

$1,950,000

4 Beds ⋅ 3.5 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

EXPERIENCE THE ART OF LIVING IN THE HEART OF WINTER PARK! This stunning home, built in 2015 by LunDev Custom Homes, is located on a quiet, tree-lined, cul-de-sac street in Fontainebleau, a desirable area of Winter Park. The 2-story residence is situated on an oversized, manicured lot with mature landscaping and features 4 bedrooms, 3 1/2 baths, formal living room, office, gourmet kitchen, great room, bonus room, and playroom. The wide-plank wood flooring, plantation shutters, Restoration Hardware light fixtures, crown molding, wainscoting, and neutral paint colors are just some of the numerous exquisite aspects of this home. The primary bedroom suite is on the first floor and has patio doors leading to the covered lanai and pool area. The primary bathroom has 2 separate vanities with quartzite countertops, frameless glass-enclosed shower, and soaking tub. The gourmet kitchen has wide-plank wood flooring, 42-inch upper cabinets and quartzite countertops, under cabinet lighting, large center island with stainless-steel undermount sink, decorative pendant lighting, vented range hood, gas grill, and Bosch stainless-steel appliances. Additional features include mudroom, laundry room with washer and dryer, walk-in pantry, and butler's pantry with quartzite countertops and wine cooler. Kitchen opens to great room and dining area, overlooking pool and impeccably landscaped backyard. The great room has a gas fireplace and wide-plank wood flooring, with patio doors leading outdoors. The fenced backyard has extensive landscaping transforming it into a secluded and tranquil private retreat with a large inground pool and spa! The paver area surrounding the pool can accommodate ample furniture. The expansive covered lanai has motorized, retractable screens, an outdoor kitchen with gas grill, refrigerator, sink, polywood cabinets with quartzite counters, and a wood-plank ceiling with fans, recessed lighting, and sound speakers. **Irrigation well** **Outdoor shower** **Ring doorbell and cameras** **Extensive outdoor lighting** **New roof in 2022**. Conveniently located near Park Ave with shops, restaurants, Central Park and SunRail station. Close proximity to Rollins College, University of Central Florida, downtown Orlando, hospitals and employment centers, museums, art galleries, entertainment venues, lakes, parks, and tourist attractions. The meticulous workmanship and obvious pride of ownership make this a must see home!

2415 Versailles Avenue, Winter Park

$1,224,900

2 Beds ⋅ 2 Baths ⋅ Interlachen Condo SubDv. ⋅ 32789 Zip Code

Experience Luxury and Charm! Discover an extraordinary residence nestled in the heart of Winter Park, where luxury meets location. This 2 bed / 2 bath (1,718 heated sq. ft.) is sure to charm you, spectacular wood parquet floors, Spanish/Mediterranean barrel roof tiles, inviting fireplaces, and walls of elegant French pane windows that flood the space with natural light. The impressive wood plank vaulted ceiling in the dining room adds a touch of European flair. The family room and dining room are adorned with floor-to-ceiling wood bookcases, adding to character and appeal. Tucked away for privacy: two charming patios overlook a secluded entryway, and meticulously re-paved brick paths wind through lush landscaping, ensuring utmost privacy and serenity. The expansive primary bedroom upstairs, offers views of Casa Feliz and the golf course. Plenty of space in large walk-in closet and its own cozy fireplace. Embrace the vibrant lifestyle of downtown Winter Park with a leisurely stroll to Park Avenue’s chic cafes, boutique shopping, and museums. The home is just steps away from the enchanting Charles H. Morse Park Moonlight Garden, known for its flower-covered archways and picturesque path leading to the historic Casa Feliz mansion. This property blends the best of both worlds: the privacy of a free-standing home and the convenience of condominium living. Recent high-end updates include a new water heater 2023, new electrical panel 2023, state-of-the-art Trane AC 2021, a stylishly remodeled kitchen with designer tile and stainless steel appliances, high-efficiency windows and doors, new tile roof 2021, and freshly painted exteriors. Trees have been trimmed and brick paths leveled as of May 2024. Only 6 distinctive units in this exclusive complex. All are unique with their own floorplans, personality, and charm. This home has two designated parking spots (1 covered parking) and offers unparalleled charm and sophistication. Maintenance-free lifestyle! Lock and leave for extended periods with no concerns. HOA handles maintenance and common areas. Don’t miss this rare opportunity—schedule your private tour today and make this Winter Park masterpiece yours!<div style="padding:56.25% 0 0 0;position:relative;"><iframe src=https://my.matterport.com/show/?m=pi8AS8w5fcE&mls=1 frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

625 N Interlachen Avenue Unit A, Winter Park

$1,524,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Nestled on a picturesque, tree-lined street, this custom Mediterranean home excludes elegance and comfort. The exterior showcases classic Mediterranean architecture with a stucco facade, terracotta roof tiles and arched doorways. Inside the heart of the home is the open concept kitchen, featuring and oversized island perfect for casual dinning and entertaining. The kitchen is equipped with state-of-the-art appliances and an electronic and lighting package, adding a modern touch to traditional design. The backyard is an oasis of relaxation, highlighted by a covered patio that seamlessly extends the living space outdoors. Here you will find a sparkling pool and a hot tub, ideal for both leisurely afternoon and evening gatherings. An outdoor gas fireplace adds warmth and ambiance, creating the perfect setting for year-round entertainment. Upstairs you will find a desk area perfect for doing homework or art projects. There is a spacious bedroom with a private bath on one side and on the other side are two bedrooms with a shared bath. This house offers the perfect blend of luxury and functionality, making it an ideal retreat for those who appreciate both style and comfort.

1571 Sunset Drive, Winter Park

$1,199,000

4 Beds ⋅ 4 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Embrace the perfect blend of modern luxury and timeless elegance in this new construction four-bedroom, four-bath home nestled in Winter Parks' Orwin Manor. Step inside to discover an open floor plan offering 2,274 square feet of meticulously designed living space with soaring 10-foot ceilings on both levels. The chef's kitchen, a culinary delight, comes equipped with high-end KitchenAid appliances and Carrara quartz countertops complemented by a marble backsplash. The kitchen also features upper cabinets, a vented extractor, and a luxurious double waterfall island perfect for gathering. The living room offers an open-concept layout, providing a seamless flow from the dining area. Clean lines, high ceilings, and large windows create a bright and airy ambiance, enhancing the spacious and inviting feel. The first level also features a bedroom and full bath for your convenience. The staircase, featuring glass railings and hardwood floors, leads to the upper level, where three additional bedrooms are located. The primary suite is a true retreat with dual custom-finished closets, a spa-like bath featuring a soaking tub, dual vanities, and a state-of-the-art frameless shower. Outdoor living is just as impressive, with a beautifully landscaped backyard, an expansive covered lanai, and an outdoor summer kitchen—all designed for privacy and relaxation. The exterior features a stately facade with detailed craftsmanship that exudes curb appeal. Additional highlights include a level five wall finish, a glass-enclosed wine cellar, a dry bar with a wine fridge, Kohler bathroom fixtures, and a two-car garage coated with epoxy featuring a pre-installed electric car NEMA plug. This property is also pre-wired for security cameras to ensure security and convenience. High-quality materials and exceptional craftsmanship are evident throughout, ensuring a lasting impression. Located just minutes from renowned Park Avenue, gourmet restaurants, boutique shopping, Advent Health Hospitals, and I-4. Experience the elegance and allure of living in Winter Park with this stunning newly built home. Why not have it all? Schedule a private showing today.

1321 Suffolk Road, Winter Park

$1,895,000

4 Beds ⋅ 3.5 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code

Presenting an extraordinary custom traditional home crafted by esteemed builder George Driscoll. Situated on Place Vendome, this remarkable property impresses from the moment you arrive. The bricked drive seamlessly continuing into the garage sets the stage for timeless elegance. Boasting four bedrooms and three and a half baths, including a pool bath, this spacious home offers refined living. Spanning approximately 4,049 square feet under air, this residence provides ample space for comfort and relaxation. As the first and only owners, meticulous care and attention to detail are evident throughout. Step through the inviting entryway and experience the artistry of this exceptional home. The primary living spaces, including the family room and living room, exude warmth and sophistication, setting the stage for memorable gatherings. Adjacent to the garage, a mudroom and laundry room combination connects the kitchen, featuring Wolf, Sub-Zero, and Bosch appliances, as well as a dinette and breakfast bar, creating a seamless flow for everyday living. Retreat to the luxurious primary suite, complete with an updated bath and a spacious walk-in closet. From the primary bed, enjoy enchanting views of the pool, creating a serene sanctuary for relaxation. An elegant office space provides a tranquil setting for work or study. Ascend to the second floor, where a versatile living space beckons. Here, a wet bar complements the entertainment possibilities, while a hidden doorway leads to a hallway connecting the areas near the wet bar to the exclusive theater room, enhancing the cinematic experience. Three additional bedrooms offer comfort and privacy, with two bedrooms conveniently sharing a Jack and Jill bath. All bedroom closets are thoughtfully built out to optimize storage and organization. Stepping outside, the motorized screen-enclosed lanai invites you to embrace the Florida lifestyle. The resurfaced heated pool, adorned with beautiful stone accents, includes an integrated jacuzzi for ultimate relaxation. The fully fenced yard provides an expansive and secure space for pets to roam freely. This exceptional property offers an exquisite place to call home with convenient access to the Winter Park Racquet Club, Park Avenue, Maitland, and the picturesque Chain of Lakes.

1350 Place Vendome, Winter Park

$1,199,900

5 Beds ⋅ 3 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. New Construction built by the well respected Konkol Construction, located in the heart of beautiful Winter Park. 2024 Parade of Homes Winner, this home is warmly known as Biscayne Bay. This residence is a stunning 2-story Modern Farmhouse Style home that offers 3,652 sqft of total space, with 2,641 sqft under air. This 5-bedroom, 3-bathroom residence was built and designed with family-centric features, making it an ideal choice for those seeking both function and style. Inside, Biscayne Bay boasts luxurious finishes and thoughtful design elements. The interior features include Transitional style design, all hard surface flooring, white oak engineered hardwood floors, white oak stair treads, 1 x 6 baseboards, and four-panel interior shaker doors. The kitchen is equipped with white shaker style cabinets, quartz countertops throughout, and designer tile backsplash. The elegant primary suite boasts a stylish tray ceiling feature and a large custom walk in closet system. The gorgeous primary bathroom offers a soaking tub, large European sport shower with frameless doors, private water closet, and high-quality Kohler and Moen fixtures. The outdoor space is equally impressive, featuring a spacious rear porch, a generously sized backyard, professionally designed landscaping with a natural bamboo privacy wall, and an Optional pool plan that provides endless outdoor enjoyment. The exterior features sand smooth finished stucco with super acrylic paint, 30-year architectural shingles, and concrete paver driveway and walkways. Additional amenities include a 2-car garage with epoxy flooring, and Professional Wi-Fi with Cat 6 smart wiring. This home truly combines modern luxury with timeless farmhouse charm, making it a perfect in town retreat. This home is conveniently located just 5 minutes away from the popular Park Avenue, known for its upscale shopping, dining, and cultural attractions. The property is also within walking distance of Lake Killarney. For golf enthusiasts, Dubsdread Golf Course is only a 5-minute drive away. Plus this home's location provides easy access to I-4 and Orlando's world-famous theme parks, which are approximately 30 minutes away.

1840 Biscayne Drive, Winter Park

$1,695,000

4 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

1650 Lakehurst Avenue, Winter Park, FL | Offered at $1,695,000 | Beautiful brick home on a huge 0.38 acre corner lot, in the Heart of Winter Park! Designed with traditional elegance in mind, this stately residence offers 4 bedrooms, 4 full baths, and over 3,700 sf of living space. Enter the home through the foyer where you’ll find formal living and dining rooms to your left and right, and a large gathering area that includes the family room and kitchen is just down the hall. Featuring custom cabinetry, stone counters, Subzero appliances, a natural gas cooktop, and double ovens, the kitchen is an absolute dream space. The family room centers around a grand fireplace and leads to a quiet reading room overlooking the back pathway and gardens. A first-floor primary bedroom offers a private en suite with double vanities, a large soaking tub, stand-alone shower, and large walk-in closet. Upstairs are 3 generously sized bedrooms, two of which share a Jack-and-Jill bath, and one with its own en suite. A bonus room with built-in storage and desks is well suited for a playroom, home office, or study. Located minutes from Park Avenue, Rollins College, Advent Health, and more this home is conveniently located and zoned for the A-rated Lakemont/Maitland Middle/WPHS school district.

1650 Lakehurst Avenue, Winter Park

$1,495,000

4 Beds ⋅ 3.5 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. ***NEW CONSTRUCTION*** Welcome to Winter Park! Bring your boat- deeded lake access on Lake Killarney! This stunning new modern home is meticulously designed and conveniently located near everything Winter Park and College Park have to offer. On the first floor, you'll find a private guest "Casita" bedroom or study with a full bath, perfect for a home office or a serene guest retreat. The large, open kitchen features quartz counters, custom cabinetry, and stainless steel appliances, including a 36" cooktop and built-in oven. Step onto the private lanai to enjoy your sparkling pool and lushly landscaped backyard. The second floor includes the master retreat, complete with a spa-like shower, dual vanities, and a spacious walk-in closet with custom shelving. Upstairs, you'll find a huge bonus room or loft, two spacious bedroom suites with walk-in closets, and a large shared bath with dual sinks. The convenient upstairs laundry room has a sink and ample natural light to make laundry day a bit brighter. This amazing location is near Winter Park Village, offering access to restaurants, shopping, and all the fun that living in Winter Park provides. Yes, you can have it all! Make an appointment today before this amazing home is gone.

629 Country Club Drive, Winter Park

$1,149,000

3 Beds ⋅ 2 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. GLORY OF A SUMMER NIGHT…experience it under the stars by the beautiful pool that comes with this innovatively styled & remodeled 3bed/2bath home, nestled in the desirable Timberlane neighborhood of Winter Park. This terrific layout features a completely updated (2020) & tastefully designed gourmet kitchen, with gorgeous cabinetry, quartz counters and large island perfect for entertaining…this opens to the living and dining room that feature large windows with views to the giant backyard and huge pool. Enjoy chilly nights with a wood burning fireplace in the family room. Additionally, there is a nice sized flex space off the living/dining area that has lots of uses: office, guest bedroom, exercise room, additional living space... French sliding doors here lead out to the covered deck, pool and backyard. Why do we love Florida?...to enjoy outdoor living of course…enjoy your new outdoor space with lots of updated pavered spaces & pool deck and newly sodded grassy areas…and of course, your huge pool that has been recently resurfaced. Inside, the bedrooms are conveniently located on the other wing of the home, all rooms are generously sized with large closet spaces. Additionally there are multiple closet storage spaces in the hall. The primary ensuite has been reconfigured and includes a large walk-in closet and updated sleek bathroom with double vanities and glass enclosed shower. This bedroom also has access to the yard/pool. Home features a 2 car garage with ample storage spaces and nice sized laundry and storage areas. Gorgeous engineered hardwood floors, plantation shutters and designer touches throughout, including a new front door to greet your guests-done in 2024. The garage also has access to the flex space and kitchen. All new windows too, done in 2020. Don’t forget about the location, currently zoned for coveted Audubon K-8 & Winter Park High School. Close to all things Winter Park…walk or bike to all the stores and restaurants on trendy Corrine Drive and Baldwin Park downtown is also just a minute away. Access to highways, hospitals and shopping are super convenient. No HOA. This is a one-of-a-kind opportunity to turn the key and enter into this desirable area of Winter Park, don’t miss your chance…Please see Virtual Tour 1 for views of home/lot/location & Virtual Tour 2 for Matterport spatial layout and walk-thru.

2217 Howard Drive, Winter Park

$1,249,000

3 Beds ⋅ 2 Baths ⋅ Georgeann Homes SubDv. ⋅ 32792 Zip Code

WINTER PARK LAKEFRONT HOME! Schedule your showing today for this Beautiful 3/2/2 Pool home with an office! NO HOA! It is situated on Lake Waunatta and part of a chain of lakes. As you enter the home, your eyes are automatically drawn to the Gorgeous views of Lake Waunatta! Wide Open Floorplan with large dining, living and family rooms and a cozy den. 2 tiled bedrooms located downstairs and the entire upstairs is the Primary Suite and large office space. There are 2 spacious closets with lots of storage space! The Primary bath is huge! Soaker tub and a newly remodeled shower! Enjoy your morning coffee or glass of wine on the private balcony outside the Primary bedroom overlooking the lake. and soaking in the sunrise or sunset. The spacious brick paved pool deck and surface was completely redone in 2021. Enjoy the evening sunsets from your covered 30' x 10' mahogany patio with teak ceilings, hard wired stereo system and outdoor lighting- just Gorgeous! Perfect home for entertaining! Private covered area over the 2021 hot tub and take a boat ride from your mahogany dock. There is plenty of room to park your boat or RV in the long driveway. The lake fed irrigation system helps to lower your water bill. 2019 ROOF, HVAC is well-maintained with service every 6 months. This home is zoned for all the top Winter Park schools! A little piece of paradise that is conveniently located to shopping, restaurants and SR 417!

7801 Georgeann Street, Winter Park

$1,190,000

4 Beds ⋅ 3 Baths ⋅ Sylvan Park SubDv. ⋅ 32789 Zip Code

This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guests will immediately appreciate the expansive paver driveway, which allows easy, off-street parking. Once inside, they will admire the abundance of natural light provided by the new, large-format windows. Not only do the new windows (2022) illuminate the interior space, but they are also impact-resistant, energy-efficient, noise-reducing, and offer UV protection. The interior renovation was designed with minimal barriers between living areas, creating open, fluid spaces that enhance day-to-day living. The bedroom and bathroom layout is ideal, offering maximum privacy: two large bedrooms share one full bathroom on one side of the house, another bedroom with an en-suite bathroom (currently used as an office) is at the center, and the primary bedroom and bathroom are on the other side. Wood or natural stone flooring, extensive millwork, vaulted ceilings, new paint, updated lighting fixtures, and new fans enhance the spaces throughout. The kitchen was renovated to include an oversized, under-mount farmhouse sink, commercial-grade faucet, new LED lighting, and quartz countertops with a waterfall edge. The primary suite was updated by a former owner but was renovated by the current owner to add a second walk-in closet with custom organization. All bathrooms received light renovations, ranging from hardware and paint to new fixtures or vanities and countertops. In addition to the visually appealing renovations, the roof was replaced in 2019 and the house was re-plumbed in 2020. The outdoor improvements may be the most valued, as they created endless opportunities for outdoor living and entertaining on the newly constructed deck and enhanced landscape. All of the outdoor living benefits Florida provides are available here. A natural gas line was brought to the house as part of the renovation, allowing for easy future modifications such as a tankless gas-fueled water heater or gas-fueled outdoor grill. Located just one and a half miles from the notable retail stores and restaurants of Park Avenue and within a well-graded public school zone, there is nothing you won’t love about this home or its location.

363 N Phelps Avenue, Winter Park

$1,499,000

32792 Zip Code

Expansive Elegance on the Water | 3.9 Acres Build Your Dream Estate at 2726 Lake Howell Lane, Winter Park, FL 32792 Step into a world of grandeur with this exceptional 3.9-acre waterfront lot at 2726 Lake Howell Lane, Winter Park, FL 32792. Priced at $1.499M, this expansive property features a remarkable 180ft dock, perfect for indulging in the ultimate lakefront lifestyle. This prime lot is ready for you to create a magnificent estate tailored to your vision of luxury. With owner financing options available, now is the perfect time to invest in your future. Positioned in a market where properties of this caliber are snapped up quickly, this superbly priced lot offers unparalleled value. Encompassed by a spring-fed lake, the lot provides pure tranquility and serenity, making it a heartwarming haven for equestrian enthusiasts. Key Features: 3.9 acres of premier waterfront property 180ft private dock with breathtaking views Ample space for a custom luxury estate Owner financing options to suit your needs Unbeatable pricing in an elite neighborhood Encompassed by a spring-fed lake in an equestrian-friendly area Secure Your Future in Luxury This is your chance to own a piece of Winter Park's most coveted real estate. Contact us today to arrange a viewing and begin the journey to your dream home. With a motivated seller eager to hand over the keys, this extraordinary opportunity won't last long. Make your move now!

2726 Lake Howell Lane, Winter Park

$1,099,000

32792 Zip Code

A Secluded Waterfront Gem in Winter Park, FL | 2.3 Acres Your Private Retreat Awaits at 2726 Lake Howell Lane, Winter Park, FL 32792 Discover an exclusive opportunity to own a pristine 2.3-acre waterfront lot at 2726 Lake Howell Lane, Winter Park, FL 32792. Encompassed by a spring-fed lake, this enchanting parcel, priced at $1.099M, features a 70ft private dock, offering direct access to serene lake views and tranquil sunsets. With owner financing available, this superbly priced lot is ready for you to build your dream estate. Imagine waking up to the gentle sounds of the water and enjoying unparalleled privacy in one of Florida's most prestigious neighborhoods. The location is a true equestrian's dream, providing a harmonious blend of pure tranquility and serenity. Key Features: 2.3 acres of prime waterfront land 70ft private dock with direct lake access Ideal for custom estate development Owner financing options available Superb pricing in a highly desirable location Encompassed by a spring-fed lake in an equestrian-friendly area Why Wait? Opportunities like this are rare. Contact us today to explore the potential of this exquisite property and start planning your luxurious waterfront escape. Your private retreat on Millionaire's Row is just a call away!

2726 Lake Howell Lane, Winter Park

$1,699,995

4 Beds ⋅ 4 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Under Construction. Welcome to this stunning 4-bedroom, 4-bathroom home nestled in the heart of Audubon Park. Boasting 2,978 square feet of living space, this residence combines spaciousness with elegance.This home offers both comfort and style. Audubon Park living at its finest awaits you here

3031 Northwood Boulevard, Winter Park

$4,200,000

7 Beds ⋅ 5 Baths ⋅ Lords Sub SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. Welcome to Winter Park lakefront living at its finest. In the heart of Winter Park, this new construction residence promises to be a masterpiece of luxury and modern living. Spanning over 5,500 square feet, this magnificent lakefront residence offers an unparalleled lifestyle with breathtaking panoramic sunset views. Tolaris Homes, an esteemed custom builder in Central Florida with over 45 years of expertise, will guide you from conceptualization to realization of your dream home. Designed to capture the essence of serene lakeside living, the home is ideally positioned to provide scenic vistas of the water and the vibrant hues of the setting sun. As you step onto the expansive balcony, the splendor of this property unfolds. The balcony, designed for relaxation and entertainment, offers a front-row seat to nature's nightly show, where the sky transforms into a canvas of oranges, pinks and purples. Imagine enjoying a glass of wine or hosting a gathering with friends and family, all while soaking in the tranquil beauty of the lake and its surroundings. Inside the home, elegance blends harmoniously with modernity, featuring spacious open-plan living areas that seamlessly transition from one room to the next. High ceilings and large windows ensure natural light illuminates the interior, enhancing the feeling of openness and connection to the outdoors. The thoughtful design includes luxurious finishes and state-of-the-art amenities, catering to every need and desire of its future owners. Experience the ultimate lakefront lifestyle with year-round boating, kayaking and water skiing on your private lake in Florida. Lake Killarney is one of the few lakes in Central Florida where you can land your seaplane on the water. Beyond the walls of this exquisite home, Winter Park offers a vibrant community rich in culture and amenities. From upscale dining and shopping to outdoor activities and renowned schools, this location balances convenience and exclusivity.

571 Lake Front Boulevard, Winter Park

$1,449,000

3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover the epitome of Winter Park living in this exceptional Douglas Grand brownstone, ideally located between Park Avenue and Hannibal Square! This remarkable residence features a private two-car garage within the secure Douglas Grand parking facility and boasts a personal street-side entrance, providing easy access to a plethora of shops, restaurants, and the SunRail station. Meticulously renovated in 2020, this townhome offers a stunning, spacious kitchen with an island, in-wall speakers, and sleek wood floors upstairs complemented by elegant new tile downstairs. High ceilings and ambient lighting enhance the open and inviting atmosphere. The luxurious master suite features two walk-in closets, dual vanities, a walk-in shower with double shower heads and body spray, a garden bathtub with smart TV connections, and a linen closet. The second bedroom offers a private bathroom and walk-in closet, while the third bedroom is generously sized with a walk-in closet. All bedrooms are equipped with Cat5 cable for seamless streaming, and the second floor includes a laundry room with ample storage. A new water heater adds to the home's convenience and comfort. High-end finishes throughout include Pella windows and doors, Kohler® fixtures, Sub-Zero, Wolf, and Bosch appliances, quartz countertops, surround sound speakers, and dual AC units. Recent updates feature new light fixtures, wired in-wall speakers, and WiFi-enabled thermostats, ensuring a modern living experience. The Douglas Grand community combines the charm of historical architecture with contemporary amenities. Centrally located in Downtown Winter Park, it provides easy access to the SunRail station, Winter Park Farmers Market, and numerous local attractions. Schedule your private showing today. Property may be under audio and visual surveillance.

335 W Welbourne Avenue Unit 103, Winter Park

$2,190,000

4 Beds ⋅ 5 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

New price on this 1/2 acre property with boat house on Lake Sue! Ready for a new owner to update or build their dream home with around the corner access to deeded private boathouse. Winter Park's desirable Forest Hills neighborhood on brick lined street with 30' on Lake Sue. Sprawling Mediterranean Ranch style home on large corner lot with secluded patio and oversized swimming pool with waterfall feature. Interior features include 4 bedrooms and 5 bathrooms. Spacious gourmet kitchen opens to family room with open wood beams and wood burning fireplace. Watch the sunset across Lake Sue from the boathouse which fronts on Fawsett Road with lift, screened enclosure, water and power. Downtown Park Avenue shopping and dining district only 1.4 miles away. Don't miss this opportunity to live the Winter Park Lake life in style!

1941 Englewood Road, Winter Park

$3,960,000

Loring Chase SubDv. ⋅ 32789 Zip Code

Entire 1.81-acre platted subdivision for sale. Total of 7 lots in desirable 32789 city of Winter Park. Six lots are zoned for residential use and one is currently zoned for office use. Link to recorded plat and HOA available upon request.

Aloma Avenue, Winter Park

$1,195,000

2 Beds ⋅ 2 Baths ⋅ Interlachen Condo SubDv. ⋅ 32789 Zip Code

Discover the charm and downtown Winter Park ambiance with this two-bedroom plus office, two-bath Mediterranean villa, a true “hidden gem” out of the way to find off Interlachen Avenue! The quaint six-villa condominium community is adjacent to the historic Winter Park Golf Course & Casa Feliz. Just footsteps from the vibrant shopping and dining on Park Avenue, this peaceful, private retreat is a European style sanctuary right in the heart of downtown Winter Park. This 1,610-square-foot, two-level condominium is a unique find and wonderful opportunity to make it your own private oasis. On the main level there is a lovely kitchen open to dining room and gorgeous living area featuring vaulted wood ceilings, a wood-burning fireplace, and two walls of French doors opening to separate private courtyards, covered lanai and fountain... There is also a secondary bedroom suite that includes an ensuite bath, perfect for guests or family. Lastly, there is a secluded office/sunroom with gorgeous arched windows and a separate entrance that offers a versatile space for work or relaxation. Upstairs solely encompasses the spacious primary suite boasting a sitting area, French doors and windows and two balconies including an expansive covered balcony off the bedroom, a walk-in closet, and ensuite bath. Embrace the old-world feel of the Spanish/Mediterranean architecture, complete with a newer community tile roof, recent new exterior paint, and peaceful winding courtyards. A secretive brick drive leads to the unit's two designated parking spots including one in a covered carport. Enjoy the "Lock and Leave" lifestyle with the enjoyment of downtown living and the seclusion of this Winter Park treasure. Walk to the Winter Park Golf Course, Casa Feliz, and stroll through the iconic streets of downtown Winter Park. Don’t miss this incredible opportunity to own a piece of Winter Park's history.

627 N Interlachen Avenue Unit B, Winter Park

Browse All Winter Park FL Above $1M Properties for Sale

Above $1 Million Winter Park Real Estate