Winter Park FL 1250+ Sq. Ft. Real Estate, Homes, Condos for Sale

3 Beds ⋅ 2 Baths ⋅ Wrenwood Heights Unit 2 SubDv. ⋅ 32792 Zip Code

This beautifully remodeled home is move-in ready and packed with upgrades. Step inside to discover brand new flooring throughout, giving the home a fresh and modern feel. The kitchen has been completely updated with new countertops, cabinets and stainless steel appliances, making it a chef's dream. Fresh paint inside and out brings a bright and inviting atmosphere to every room. Both bathrooms have also been remodeled, featuring modern fixtures and stylish finishes. Additionally, you'll have peace of mind knowing the roof was put on in 2022 and most major mechanical elements have been updated. Located in the heart of Winter Park, this home is just minutes from top-rated schools, parks, shopping, and dining. Enjoy the convenience of being near major roadways, while still being tucked away in a peaceful neighborhood. Don't miss this opportunity to own a stunning, remodeled home in beautiful Winter Park!

5210 Poinsetta Avenue, Winter Park

$750,000

4 Beds ⋅ 3.5 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code

Discover this stunning POOL home, located in the exclusive gated community of Enclave at Aloma, in the heart of Winter Park. This meticulously maintained property is equipped with 4 bedrooms, 3 full bathrooms, a half bathroom, flex room, and a loft. With over 3,200 sq. ft of living space, this home seamlessly blends modern luxury with natural serenity, offering breathtaking conservation views that will always captivate. As you enter the home through the covered front porch, you're greeted by an inviting open floor plan bathed in natural light. The heart of the home is the spacious and modern kitchen, fitted with granite countertops, 42" cabinetry, and a large breakfast bar, ideal for casual dining or entertaining. Stainless steel appliances, including a built-in oven and microwave, offer both style and functionality for any home chef. The kitchen flows seamlessly into the expansive living and dining areas, ensuring effortless interaction and easy hosting for gatherings. The downstairs office, perfectly situated for those working from home, can also double as a study or flex space. Adjacent to the office is the elegant guest bathroom, providing convenience and privacy for visitors. Upstairs, a spacious loft area offers additional living space, perfect for use as a media room, play area, or secondary office. The generously sized primary suite provides breathtaking views of the surrounding conservation area, creating a peaceful retreat. The luxurious en-suite bathroom features dual vanities, a deep soaking tub, and a stand-up shower, delivering a spa-like experience in the comfort of your home. The additional three guest bedrooms are thoughtfully designed, with two sharing a stylish and convenient Jack and Jill bathroom, offering comfort and privacy for family or guests. Step outside into your private backyard oasis, where a sparkling saltwater pool and hot tub await—perfect for cooling off during warm Florida days or relaxing in the soothing jets of the hot tub after a long day. Whether enjoying a refreshing swim or unwinding in the warmth of the spa-like hot tub, this outdoor space caters to your every need. The covered patio offers a shaded retreat, ideal for outdoor dining or entertaining while taking in the tranquility of the serene conservation. Enjoy proximity to Trinity Prep, Oviedo on the Park, Red Bug Lake Park, Rollins College, downtown Winter Park, and UCF. Residents also benefit from easy access to SR 417, making commutes to downtown Orlando, two International Airports, and Theme Parks much more convenient. Don’t miss the opportunity to make this stunning Winter Park home yours today!

8057 Pleasant Pine Circle, Winter Park

$1,475,000

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

$319,900

3 Beds ⋅ 2.5 Baths ⋅ Winter Green SubDv. ⋅ 32792 Zip Code

Welcome to this charming three-bedroom home, perfectly designed for both comfort and entertaining. As you enter through the large private courtyard, envision cozy lounge chairs, a settee, and a grill, perfect for outdoor gatherings. Inside, the inviting family room to the right features a cozy fireplace, ideal for relaxing evenings. The updated galley kitchen, complete with stainless steel appliances, flows seamlessly into the formal dining room, making dinner parties a breeze. A convenient half bath and utility room are located nearby for added functionality. Downstairs, you’ll find a versatile bonus room that can be used as a den, office, game room, or even a movie room. Upstairs, both bedrooms feature sliding doors that open to private balconies. The spacious master suite boasts a walk-in closet and a well-sized ensuite bath, while the second bedroom offers a comfortable space with a full bath just outside the door. This home is in excellent condition and ready for new owners to move in and enjoy!

1510 Winter Green Boulevard, Winter Park

$350,000

4 Beds ⋅ 2 Baths ⋅ Howell Branch Woods SubDv. ⋅ 32792 Zip Code

Charming East Winter Park Gem with Major Updates and Room to Personalize! Nestled in the sought-after East Winter Park neighborhood "Howell Branch Woods", directly across the street from Eastbrooke Elementary School, this inviting home offers a blend of convenience and potential. With major upgrades already completed, including a brand-new roof, updated electrical panel, refreshed A/C system, and modern plumbing, this property is ready for you to move in and make it your dream home! The spacious back-yard is a standout feature, highlighted by a majestic oak tree that provides both shade and a touch of natural beauty. While the home could benefit from a complete cosmetic upgrade, it boasts a solid foundation and the essential updates you won’t have to worry about. Whether you’re a first-time buyer ready to put your personal stamp on a home, or an investor looking for a property with potential, this East Winter Park residence is an excellent opportunity. Don't miss out on the chance to own a home in this desirable area with all the big-ticket items already taken care of!

5618 Tangerine Avenue, Winter Park

$399,000

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 3 SubDv. ⋅ 32792 Zip Code

Come see this beautifully maintained 3-bedroom, 2-bathroom home located on an oversized lot, over 1/4 acre! The home features a split floor plan, providing both privacy and plenty of space for everyone. The living room includes a large wood-burning fireplace and opens up to a spacious, screened-in porch and huge, fenced-in yard. In addition to the living room, there is a breakfast nook and formal dining room located near the kitchen. Key updates include a new roof in 2022, an AC system installed in 2018, and fresh interior paint in 2018, ensuring a move-in ready experience. This home has been lovingly cared for and is ready for its next owners. Don’t miss your chance to own this centrally located home in a fantastic school district!

1290 Gladiolas Drive, 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

$950,000

3 Beds ⋅ 2.5 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

This stunning David Weekly home, built in 2017, perfectly captures the luxurious Winter Park lifestyle, just four blocks from the sophistication of Park Avenue and one block from the vibrant Winter Park Village. Stroll to renowned restaurants, boutique shops, and entertainment venues, all steps from your front door. Designed for the ultimate in hosting and entertaining, the open-concept living space is adorned with elegant finishes and designer touches, offering a seamless blend of style and comfort. The first floor boasts three generously sized bedrooms and two full baths, including a primary suite with a spa-like bathroom and spacious walk-in closet. Upstairs, the expansive living and dining areas invite effortless gatherings, with a gourmet kitchen featuring high-end stainless steel appliances, granite countertops, an island, and a natural gas cooktop—perfect for preparing gourmet meals while entertaining guests. Sliding glass doors open to a large balcony with new trek decking, ideal for alfresco dining or evening cocktails under the stars. The HOA provides the convenience of weekly professional lawn care and includes water for the irrigation system, ensuring your outdoor spaces are always pristine without the hassle. Built for both beauty and energy efficiency, the home includes double-pane low-E windows, R-38 insulation, and a tankless water heater..This move-in-ready masterpiece offers not just a home but an elevated lifestyle in one of Winter Park’s most sought-after locations. Schedule your private tour today!

439 N Capen Avenue, Winter Park

$825,000

4 Beds ⋅ 2.5 Baths ⋅ Brookshire Heights SubDv. ⋅ 32792 Zip Code

Welcome home to Winter Park, with its tree-lined streets and where the mailman still delivers to your door! This spacious home is located in the Brookshire Heights neighborhood and is mere steps away from the highly rated Brookshire Elementary School and Winter Park High School. As you step inside, you'll be greeted by 12' ceilings and an abundance of natural light pouring in through the many large windows, creating a bright and airy atmosphere. The spacious split floor plan offers a seamless flow between the sizable formal living room, dining room, and family rooms—perfect for both relaxation and entertaining. The kitchen is open to the great room and features newer appliances, a breakfast bar with seating for 4 and a built-in pantry. Storage is plentiful throughout the home, with multiple spacious closets for all your organizational needs. Your generously sized 18' x 13' primary bedroom is a true retreat, complete with dual closets, a french door leading to the rear lanai and an ensuite bathroom with dual vanities. The primary bath also features a luxurious soaking tub, separate shower and private water closet. Step outside to enjoy the tranquil 20' x 12' screened-in rear lanai, perfect for sipping your morning coffee or unwinding in the evenings. The yard is beautifully landscaped with mature oak trees and well-maintained hedges, offering both shade and privacy. This highly sought after community has so much to offer, with fantastic amenities, including an olympic sized swimming pool, public golf course, tennis and pickleball courts and scenic biking trails. You are also conveniently close to Full Sail, UCF and Valencia colleges, shopping, dining, OIA, the Crosby Wellness Center, and AdventHealth Winter Park. ROOF - 2024, HVAC - 2021, PLUMBING - 2003, ELECTRIC - 2003. The home offers easy access to everything you need, making it an ideal blend of comfort, convenience, and lifestyle! This home is easy to show so arrange for your private showing now!

2235 Coldstream Drive, 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

$575,000

4 Beds ⋅ Slovak Village SubDv. ⋅ 32792 Zip Code

Opportunity awaits, this duplex is located in the desirable Winter Park area, each unit features 2 bedroom and 2 full bathrooms, a covered carport, and off street parking, a dedicated laundry closet with washer and dryer included, a large living room, a dining room, and a large kitchen with patio. This property was fully renovated from the ground up in 2022! All work permitted. The renovations consisted of all-new plumbing including all plumbing fixtures, new ducts, AC and Air handlers, a new roof, all new roof, all new windows, sliders and doors, insulated walls and ceilings, frameless glass shower doors, brand new cabinets with quartz countertops, all brand new appliances and a brand new septic tank. Duplex occupied by original tenants since 2022***DO NOT DISTURB TENANTS** Call Listing Agent for Rental Info and Showing instructions.***

2605 Holly Road, 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

$949,000

3 Beds ⋅ 3.5 Baths ⋅ Lake Spier Crossing SubDv. ⋅ 32792 Zip Code

2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! Don't miss your opportunity to win this extraordinary move-in ready new residence situated amidst the tranquil shores of Lake Spier and Lake Compton, within the exclusive Lake Spier Crossing community centrally located in Winter Park. Consisting of 10 impeccably designed two-story townhomes, this enclave of contemporary living is brought to you by Meridian Homes, Winter Park's premier builder. Anticipate modern architectural brilliance and carefully planned floor layouts that prioritize stylish, hassle-free living. Meticulous attention to detail is evident both indoors and outdoors. Your kitchen boasts state-of-the-art stainless steel appliances and elegant stone countertops, complemented by luxurious hardwood flooring throughout. Convenience is key, with in-unit laundry facilities and a two-car garage ensuring seamless daily routines. Residents of Lake Spier Crossing relish exclusive access to three private docks, ideal for launching paddleboards, kayaks, or enjoying a spot of fishing. This exceptional locale offers proximity to Lake Baldwin Dog Park and the picturesque Cady Way Trail, catering to an active outdoor lifestyle. Enjoy the convenience of strolling to Downtown Baldwin Park for dining, shopping, and lively entertainment, or embark on a leisurely 10-minute bike ride to the iconic Park Avenue. Benefit from access to Winter Park's esteemed school district, enhancing the allure of this exceptional community.

1919 S Lakemont Avenue, 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

$320,000

3 Beds ⋅ 2.5 Baths ⋅ Winter Park Pines Condo SubDv. ⋅ 32792 Zip Code

Welcome to your dream home! This elegant two-story villa-style condominium combines sophistication and comfort. The convenient downstairs primary bedroom ensures privacy, while the single-car garage and guest parking cater to your needs. Enjoy the serene courtyard, cozy brick corner fireplace, and spacious kitchen with stainless steel appliances. The open great room features high ceilings and tile floors, with natural light flowing through large windows. A bonus room and storage closet overlook the fenced-in rear patio, perfect for displaying potted plants. Impeccably maintained and move-in ready, this unit must be owner-occupied as rentals are not allowed. Located near Full-Sail University, Rollins College, the University of Central Florida, and Downtown Winter Park’s Park Avenue, you’ll have easy access to top-notch educational institutions and vibrant shopping and dining options. Don’t miss out—schedule your viewing today and experience the blend of modern features and inviting ambiance this home offers!

543 Warrenton Road Unit 543, 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

$979,000

3 Beds ⋅ 2 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Timeless Elegance in the Heart of Winter Park! Discover the perfect blend of charm and modern luxury in this stunning 3-bedroom, 2-bathroom POOL home, located in the highly sought-after “Tree Streets” neighborhood of Winter Park. From the moment you step inside, you'll be welcomed by an open-concept kitchen, dining, and living area designed for both style and functionality. The beautifully updated kitchen features TOP-Of-THE-LINE GE Café stainless steel appliances, including an induction cooktop, double oven, and a Bosch ultra-quiet dishwasher, all installed in 2023. Complemented by professionally painted cabinetry with pull-out shelving, a spacious island extension, quartzite countertops and backsplash, and premium Kohler fixtures, this space is a chef’s dream. The primary bedroom exudes tranquility with its serene ambiance and custom-designed walk-in closet. Adjacent to this private retreat, an office overlooks the sparkling pool, offering a peaceful workspace. Both bathrooms have been meticulously remodeled to deliver a luxurious, spa-inspired experience. The EXPANSIVE FAMILY ROOM is ideal for entertaining or unwinding, featuring new French doors that open to the pool area. The entire interior has been professionally painted. Outdoors, you'll find a sprawling deck perfect for lounging or hosting, alongside the shimmering SALTWATER POOL, newly added in 2022. Lush tropical landscaping surrounds the space, providing privacy and a resort-like atmosphere. This home is packed with upgrades, including designer light fixtures, dimmable recessed lighting, and a state-of-the-art HVAC system with a 22 SEER variable speed unit and humidity control (installed in 2023). The back living room also boasts a 20.5 SEER mini-split system, both covered by a 10-year warranty. Owned solar panels and Roof (both new in 2019) provide energy savings. Double-paned windows with plantation shutters, a full-home re-pipe and rewire have been completed in recent years ensuring value and efficiency. Additional outdoor improvements include a new sprinkler system, fresh sod, landscaped garden beds, a paver pathway, a retaining wall, and new gutters. Nestled on a quiet, tree-lined street, this neighborhood offers easy walkability to Phelps Park (with tennis and pickleball courts) and the serene Kraft Azalea Garden. Downtown Winter Park and the Winter Park Village are both less than two miles away. Take moment to visualize yourself in this beautiful property and then make an appointment to see it in person, you won't be disappointed!

1762 Chestnut Avenue, Winter Park

$580,000

4 Beds ⋅ 2 Baths ⋅ Lake Waunatta Woods SubDv. ⋅ 32792 Zip Code

Nestled within the desirable family community of Lake Waunatta Woods, this home is beautifully updated and meticulously maintained. The fenced back yard is spacious with a patio and gazebo that is perfect for relaxing, BBQ's and entertaining. Enjoy the benefits of top rated Winter Park schools and the convenience of nearby amenities. State Road 417, the University of Central Florida, Full Sail University, downtown Winter Park, and Downtown Orlando! NEW ROOF! NEW AC! NEW KITCHEN APPLIANCES! NEW WASHER AND DRYER! NEW FENCE! NEW GAZEBO AND LANDSCAPING! Preferred lender offering appraisal credit! Bring all offers as homes in this neighborhood rarely go on the market and don't last long! All rooms sizes should be confirmed by buyer.

4025 Quenita Drive, Winter Park

$879,000

3 Beds ⋅ 3.5 Baths ⋅ Lake Spier Crossing SubDv. ⋅ 32792 Zip Code

Special financing or closing cost credits available to qualified buyers. 2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! Don't miss your opportunity to win this extraordinary move-in ready new residence located between the tranquil shores of Lake Spier and Lake Compton, within the exclusive Lake Spier Crossing community in Winter Park. Featuring 10 impeccably designed two-story townhomes, this enclave of contemporary living is crafted by Meridian Homes, Winter Park's premier builder. Expect modern architectural brilliance and thoughtfully planned floor layouts for stylish, hassle-free living. Meticulous attention to detail is evident indoors and outdoors. The kitchen includes state-of-the-art stainless steel appliances and elegant stone countertops, complemented by luxurious hardwood flooring throughout. Convenience is prioritized with in-unit laundry facilities and a two-car garage. Residents of Lake Spier Crossing enjoy exclusive access to three private docks, perfect for paddleboarding, kayaking, or fishing. This exceptional location offers proximity to Lake Baldwin Dog Park and the picturesque Cady Way Trail, ideal for an active outdoor lifestyle. Enjoy the convenience of walking to Downtown Baldwin Park for dining, shopping, and entertainment, or taking a leisurely 10-minute bike ride to the iconic Park Avenue. Access to Winter Park's esteemed school district enhances the allure of this exceptional community.

1915 S Lakemont Avenue, 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

$405,000

3 Beds ⋅ 2 Baths ⋅ Howell Estates 2nd Add SubDv. ⋅ 32792 Zip Code

Explore your ideal Florida Forever Home! Prepare to be captivated by this beautifully renovated one-story, three-bedroom, two-bath single-family home, situated in the tranquil and well-established HOWELL ESTATES community. Tucked away in a cul-de-sac, this home features a split floor plan, and freshly painted interiors and exteriors. Every aspect has been thoughtfully updated to ensure it's ready for the new owners to move in. Elegant and durable vinyl flooring throughout the home provides a fresh, modern look. Brand new kitchen cabinets paired with stunning quartz countertops create a perfect space for culinary adventures. Both bathrooms have been completely remodeled with contemporary fixtures and finishes. Brand-new stainless-steel appliances add both style and efficiency to the kitchen. Stylish new light fixtures and recessed lighting throughout the home enhance its bright and airy feel. Enjoy peace of mind with recently updated plumbing throughout the home. The living area flows seamlessly into a screened-in patio, perfect for outdoor relaxation without the hassle of bugs. Enjoy the convenience of a 2-car garage, complete with washer and dryer hookups, providing ample storage and laundry space. Reduce your carbon footprint and utility bills with energy-efficient solar panels. Updated windows and sliding doors provide enhanced energy efficiency and curb appeal. The roof was replaced in 2018, offering long-lasting protection for years to come. Seize the chance to make this beautifully updated home yours. It's VACANT and READY FOR IMMEDIATE MOVE-IN. WELCOME HOME.

1035 Lundy Court, Winter Park

$399,999

3 Beds ⋅ 2.5 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code

***Welcome to 7632 Aloma Pines Ct!***Located in the Gated Community of Aloma Pines in Winter Park. This Town Home features 3 bedrooms and 2.5 baths. Upon entering you will be greeted with a bright open concept, Beautiful Tile Floors throughout, Crown Molding and motorized shades over the OVERSIZED SLIDING GLASS DOOR! The beautiful kitchen features 42" cabinets, Granite Countertops, backsplash, an over-sized pantry, STAINLESS STEEL APPLIANCES and a large ISLAND with bar seating! On the second floor you will find the bedrooms along with the the laundry room. All of your fixtures and fans have been upgraded! Call for your private showing today!!

7632 Aloma Pines Court, 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

$420,000

4 Beds ⋅ 2.5 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Discover the charm and convenience of this beautiful one-story home in the heart of Winter Park. It offers 4 bedrooms with 2.5 baths, and 1,477 square feet of living space. This stunningly renovated property offers brand new features throughout and a convenient location. Winter Park's proximity to local shops, breweries, restaurants and an excellent school system make it a desirable area where many families look to settle. The home itself blends classic charm with modern luxury, offering a fresh and stylish living experience. Don’t miss the opportunity to own this move-in-ready home where every detail has been carefully considered. Schedule your private tour today!

1847 Azalea Avenue, Winter Park

$415,000

3 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Nestled in the heart of Winter Park's charming Wrenwood neighborhood, this renovated gem is ready for its new owner! Featuring 3 bedrooms, 2 bathrooms across 1560 square feet, this home is a fantastic buy and has been completely renovated with over $85,000 in upgrades. Step inside to discover a sun-kissed interior boasting a fully renovated space adorned with chic tile plank flooring, upgraded kitchen cabinetry, and a primary bathroom designed for relaxation. The kitchen stands out with its sleek new finishes, including large island, subway tile backsplash and plenty of storage. The kitchen and inviting layout provides an atmosphere for those who love to cook and entertain. Outside, a spacious, fully fenced yard offers pets a playful haven and residents a serene escape. Located just 10 minutes to Park ave and all the best restaurants and shopping, this property is a dream come true for first-time buyers, investors, or anyone seeking a cozy and convenient abode in desirable Winter Park. Four point updates include: Roof 2021, HVAC 2015, Plumbing 2016 and new Electrical Panel in 2014.

5419 Ardmore Drive, 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

$485,000

4 Beds ⋅ 2 Baths ⋅ Park Green SubDv. ⋅ 32789 Zip Code

Welcome to this exquisitely renovated home perfectly located in the heart of Winter Park! The new owners will enjoy peace of mind with a new kitchen that boasts granite countertops, exclusive backsplash, stainless steel appliances, spacious pantry, new AC, new luxury waterproof flooring throughout the home, large rooms, lots of natural light, wood burning fire place and more. This expansive home offers a truly exceptional living experience! Enjoy your comfortable backyard with plenty of space for entertaining! Centrally located near Winter Park Village, Park Ave Shopping District, Farmers Market, Whole Foods and more. Don’t miss this opportunity! Schedule your showing appointment today!

1209 Park Green Place, Winter Park

$489,000

4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 4th Add SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. *Fianl offers by 2:00pm 9/8** Charming 4-bedroom, 2-bathroom pool home, fully renovated to blend modern elegance with comfort. The open-concept living area features abundant natural light, leading to a gourmet kitchen with upgraded appliances, countertops, and ceramic tile throughout. Relax in the spacious primary suite with an en-suite bath, while three additional bedrooms for family or guests. One guest bed room can convert into an office because of a custom built Murphy bed. Step outside to your private backyard oasis, complete with a sparkling pool and a patio for outdoor entertaining. Located in the heart of Winter Park, you’ll enjoy easy access to top-rated schools, shopping, and dining. Don’t miss this opportunity to own a beautifully updated home in a sought-after neighborhood!

5425 Ferrol Drive, 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

$525,000

3 Beds ⋅ 2 Baths ⋅ Fairbanks Shores 4th Add SubDv. ⋅ 32789 Zip Code

Remodeled 3/2 pool home in Winter Park on a quiet street with a detached ADU for a home office/gym/studio adds to the appeal. An open bright custom kitchen is perfect for entertaining. The satisfactory 4pt inspection will help in lowering insurance costs. Being nestled between College Park and Downtown Winter Park with easy access to I4 and excellent schools, makes this a standout turnkey home a fantastic location. No HOA and priced below appraisal!

2877 Euston Road, Winter Park

$379,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Welcome to this charming home in the desirable Eastbrook Neighborhood of Winter Park! This residence offers 3 bedrooms and 2 bathrooms, providing ample space for comfortable living. With two large living areas, there’s plenty of room for relaxation and entertaining. The eat-in kitchen is perfect for casual dining and meal preparation, featuring a functional layout and modern amenities. Step outside to the spacious, fully fenced backyard—an ideal spot for outdoor gatherings, play, and gardening. The two-car garage adds convenience and additional storage. With 1,516 square feet of well-designed living space, this home combines practicality with cozy charm. Situated in a fantastic location in Winter Park, you'll enjoy easy access to local amenities, parks, and schools. Don’t miss this opportunity to own a home in one of Winter Park’s sought-after neighborhoods. Schedule your showing today and discover all the opportunity this wonderful property has!

3425 Balsam Drive, Winter Park

$509,500

3 Beds ⋅ 2 Baths ⋅ Lakemont Heights SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Discover comfort and convenience in this charming 3 bedroom, 2 bath 1,734 single-story ranch, perfectly situated in central Winter Park. With 1,734 square feet of beautifully updated living space, this well-maintained home boasts a 2024 flat roof, new slider door, fresh interior paint, and a fully renovated hall bath. The modern amenities include a smart home system that lets you control the irrigation, thermostat, camera, and garage from your phone, plus an electric charging outlet in the 1-car garage. Other amenities include an interior laundry, plantation shutters, upgraded electric, and new shed for additional storage. The brick side screen porch off the master bedroom, paver driveway, and detached workshop with electric, water, and AC add to its appeal. Located just minutes from Park Avenue's vibrant shopping and dining scene, and within an excellent school district, this home offers the best of Winter Park living amidst mature landscaping and serene fountains. Quiet street with no thru traffic. Ideal property for an investor, first-time buyer, or a downsizing buyer. Walk to Lakemont Elementary or the Winter Park YMCA. Minutes from the shops and restaurants of downtown Winter Park. Don't miss out on this cozy haven!

1816 Palmer Avenue, Winter Park

$159,900

2 Beds ⋅ 2 Baths ⋅ Colonies SubDv. ⋅ 32792 Zip Code

Discover this beautifully renovated 2-bedroom, 2-bathroom condo located in the Colonies Condo Community in Winter Park, FL. This charming home has been updated to offer modern comfort and style. The newly remodeled kitchen boasts elegant quartz countertops, brand-new cabinets, and top-of-the-line stainless steel appliances, perfect for any home chef. The entire home features luxurious vinyl wood plank flooring providing a seamless and sophisticated look throughout. A brand-new air conditioning unit ensures year-round comfort, while fresh paint throughout the home adds a bright and welcoming ambiance. New plumbing as well adds peace of mind. The Colonies community offers fantastic amenities, including a pool, clubhouse, dog park, and tennis courts. Additionally, the community is in the process of renovating the balconies, further enhancing the appeal of this well-maintained neighborhood. Conveniently located close to major highways, this condo provides easy access to downtown Orlando, the Orlando International Airport, and local universities. Shopping, dining, and entertainment options are also just a short drive away. Don’t miss the opportunity to own this fully renovated condo in a prime Winter Park location—schedule your showing today!

7340 Daniel Webster Drive Unit 6, Winter Park

$835,000

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

Discover the perfect canvas for your dream home at 674 Randy Lane in Timberlane, where your aspirations meet reality. This prime 0.41-acre lot, zoned for the coveted Audubon K-8 School, offers an ideal location at the corner of Randy Lane and Fosgate Drive. With 200 feet across the back and 35 feet on General Rees, there’s ample space to build your multi-car garage or workshop. The lot is ready to go with underground utilities and sewer connected. The existing 1950's home and oversized garage/workshop have been part of Timberlane's charm for decades. This property is in the heartbeat of everything.... Across from Blue Jacket Park, near downtown Baldwin Park. Stroll through the neighborhood and land at East End market, Kelly’s Homemade Ice Cream, along with all the shops and restaurants on Corrine Drive. Venture North just 2.5 miles to the cultural delights of Park Avenue in downtown Winter Park. If you are looking to land just a few minutes from Downtown Orlando and easy Access to I-4…this is the location for you. Embrace the convenience of urban amenities in this fabulous neighborhood, enriched by top-rated schools!

674 Randy Lane, Winter Park

$379,900

4 Beds ⋅ 2 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. You cannot beat this location!! Ready for a new generation to love. This spacious 4 bedroom/2 bath home boasts almost 1900 sq ft in a prime location. The large primary bedroom has a walk-in closet and attached bath. Walk out the french doors to your private patio and enjoy your beautifully landscaped lot. The 3 additional bedrooms are good sized, and any could be used as an office, workout room, or den. This large .25-acre corner lot with beautiful shade trees offers endless possibilities for the outdoor enthusiast. Sitting quietly in the heart of Winter Park (with NO HOA!!) you are just minutes from the Winter Park Village, Rollins College, the Sun Rail Station, Park Avenue, Advent Health Hospital, and endless options for shopping and dining. Unbelievable value for a home of this size in a premium location!

1902 Magnolia Ave, Winter Park

$359,000

3 Beds ⋅ 2 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. HIDDEN GEM ALERT! A rare opportunity to own a move-in ready 3 bedroom 2 bathroom home located in the heart of Seminole County Winter Park with a huge backyard and no HOA at an affordable price! WOW!! Located on a large lot on a dead-end street, this "Old Florida" block construction ranch is a perfect starter home for any family or a great addition to an investment portfolio. The exterior is highlighted with great curb appeal with an extra wide paver driveway, mature landscaping, and paver front walkway and patio area. The interior consists of a bright and OPEN CONCEPT dining/kitchen/living space with ample room to relax or entertain. The kitchen boasts granite counters, solid wood cabinets, stainless steel appliances, eat-in island, and a closet style pantry. The master suite has a total of THREE CLOSETS and a spacious bathroom with updated vanity and tile shower. The opposite side of the SPLIT LAYOUT home contains two additional bedrooms and a recently updated full size bathroom. Outside is a massive fully fenced backyard with paver patio and shed for additional storage. Other features include: a spacious indoor laundry room, irrigation system for front lawn, 2014 roof, and 2018 HVAC. Zoned for great schools and centrally located only 15 minutes from downtown Orlando and 30 min from MCO airport this home is perfectly situated to meet YOUR needs! Opportunities at this price simply do not come on the market often! Book your private showing today!!

1935 Azalea Avenue, Winter Park

$659,900

4 Beds ⋅ 3 Baths ⋅ Quail Run SubDv. ⋅ 32792 Zip Code

Welcome to this spectacular 4-bedroom, 3-full-bath executive home in the highly sought-after Quail Run neighborhood. Walking into this home you will immediately take note of the beautiful French pattern travertine floors, the abundance of natural light, and a split floor plan!! Filled with upgrades the home offers newer double-pane high-efficiency windows, Water Heater 2023, Roof 2022, and HVAC System 2016 just to name a few!!! Let's not forget the chef’s dream kitchen featuring top-of-the-line Stainless-Steel appliances and exquisite granite countertops making it perfect for culinary enthusiasts and entertainers alike! Headed out to the back of the property you will exit through Top-of-the-line Pella sliding glass doors into a covered screened patio that leads out to a 200 sq ft paver patio area perfect for grilling and all completely enclosed with Vinyl fencing on this oversized lot!! Nestled at the end of a quiet cul-de-sac, this home offers peace and privacy while being just minutes away from UCF, 417, shopping, and top-notch dining. This exquisite home is a rare find and won’t last long, schedule your private showing today!

4598 Whimbrel Place, Winter Park

$485,000

3 Beds ⋅ 2.5 Baths ⋅ Autumn Glen Ph 3 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated single-family home in Winter Park, FL. This charming property offers three bedrooms, each thoughtfully designed for comfort and style. Additionally, there is a versatile flex space that can easily function as a fourth bedroom, home office, or playroom. The primary bedroom is conveniently located on the main floor, providing ease of access. The home boasts two full bathrooms and a convenient half bath, ensuring ample facilities for family and guests. Throughout the property, you will find tasteful updates and attention to detail, along with plenty of storage space. Situated on a generously sized corner lot, this home is zoned for the highly-rated Lake Howell High School and is centrally located to enjoy all that Winter Park has to offer.

1663 Meadowgold Court, 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

$394,400

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. HOME SWEET HOME! Charming home on a serene cul-de-sac! Move right into this freshly painted, immaculate beauty. Great curb appeal and extra large .35 acre lot will definitely impress! Upon entering the double door entry to brick floored foyer, this light & bright home with terrazzo floors throughout will capture your attention. TWO cheerful living areas include formal living room & family room/dining room combination. The updated kitchen with beautiful wood cabinets, granite countertops & newer appliances opens to dining room and overlooks spacious 22x16 screened patio & oversized fenced backyard... plenty of room to roam, garden & play PLUS a large storage shed. Primary bedroom boasts a large closet, linen closet & ensuite bathroom with updated vanity. Two guest bedrooms share guest bath with updated vanity also. Extra features include: 2 car garage with NEW 2022 garage door, NEW 2021 energy efficient double pane windows throughout, NEW 2021 roof, 2016 AC, 2003 updated plumbing (plus 2022 replacement/ lining of underground sewer pipes $17,000+), Eastbrook Elementary, Tuscawilla Middle, Lake Howell High. NO HOA & oversized lot provide the perfect opportunity to call 2042 Cocos Court HOME!

2042 Cocos Court, Winter Park

$515,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Unit 05 SubDv. ⋅ 32792 Zip Code

Welcome to this spacious three-bedroom, two-bath home in the highly sought after tree-lined community of Winter Park Pines! You will find ample space in the garage with multiple areas of storage. Upon entering you are greeted into the main living area with beautiful parquet floors and unique floor to ceiling rectangular windows boasting tons of natural light. The separate formal dining room features a unique Spanish tile which spills into the open-concept kitchen. Down the hall, you will find three generous size rooms with expansive closets. The large second bathroom features ample counter space with a shower tub combination. Enjoy the privacy of the sizable master bedroom located in the rear of the home with en-suite bath. The massive backyard is fully fenced in with no rear neighbors for year-round entertaining. This home features a 2021 A/C and handler, 2021 roof, 2017 tankless water heater system, and replumbed with PVC to city line in 2023. Convenient to the 417, fantastic shopping, dining, top rated Orange County schools and steps away from the Cady Way Trail.

2758 Cady Way, Winter Park

$439,900

3 Beds ⋅ 1.5 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Location! Location! Location! Here is your perfect chance to buy a ready move-in home in Winter Park! As well as being in Winter Park, this home backs up to a city easement which further backs up to the wooded area of the private Interlachen Country Club Golf course. NO REAR NEIGHBORS and NO HOA! This beautiful 3 bedroom, 1.5 bath approximately 1350 sq ft home sitting on a generous 0.2-acre lot with mature landscaping, is just the retreat you've been looking for! Winter Park offers serene parks, picturesque walking trails, and lush greenery at your doorstep. You'll feel a world away while still being just moments away from all the amenities and attractions the area offers. Downtown Park Ave is just minutes away, as well as access to the highways. Whether you're enjoying a stroll through the neighborhood or unwinding in your private backyard oasis, you'll love coming home to this peaceful paradise.

633 Balfour Drive, Winter Park

$799,000

5 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Fabulous opportunity to own a 5 bedroom 3 bath home on a large .32 acres (13,814 square feet) in one of Winter Park’s most sought-after neighborhoods. Enjoy relaxing in your large pool plus screened enclosure. The split floorpan allows for idea family living with 2 of the bedrooms including ensuite bathrooms. All of Winter Park's exclusive dining and shopping nearby. This neighborhood is truly a gem zoned for Audubon K-8 and Winter Park High school in an area undergoing rapid transition due to the location and the quality of schools.

2258 Howard Drive, Winter Park

View All Latest Winter Park 1250+ Sq. Ft. Properties for Sale

1250+ Sq. Ft. Winter Park Real Estate