Winter Park FL Just Listed Real Estate, Homes, Condos for Sale

4 Beds ⋅ 2 Baths ⋅ Carolyn Estates SubDv. ⋅ 32792 Zip Code

Single story home seeks new owners! This property features a welcoming great room with a cozy wood-burning fireplace, formal dining room, and a bright kitchen with plenty of counterspace and cabinetry. Generous sized bedrooms provide ample space for family and guests. Primary bedroom has two closets, double vanity sinks, and a walk-in tiled shower. Secondary bath offers a vanity with double sinks, tub/shower combo, and a door leading to the back porch. Enjoy the screened lanai overlooking your spacious backyard, ideal for gardening or weekend barbecues (plenty of space for a pool too). Conveniently located near shopping, dining, and top-rated schools. This home is part of an estate sale and can use some updating and TLC. Schedule your showing today and get moving tomorrow.

1748 W Cheryl Drive, Winter Park

$579,900

3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 02 SubDv. ⋅ 32792 Zip Code

GORGEOUS totally remodeled the block single story situated in a prime location just minutes from Park's Park Avenue! This Luxury & Elegant 3 bedrooms and 2 baths plus extra space has a split layout and Upgraded better than new! New High-end Windows and Sliding Doors that are Florida approved and Exceed 130 MPH Wind Ratings and Energy Star with Manufacture Lifetime Warranties! New pavers for the driveway, sidewalk, front porch and patio! New A/C, Waterheater, Washer & Dryer. New High Quality Engineered HardWood Flooring! New insulation! New ceilings and walls Texture! Pinewood trims and baseboards around! No MDF! New ceiling fans, light textures. New interior doors all over. New new painting outside and inside including ceilings! Upon entering, you will be greeted by an open area with natural lights, followed by a massive space offered by the integrated living room, dining room and kitchen! The kitchen offers a fully equipped New Kitchenaid appliance package, Custom cabinetry, Quartz countertops and Oversized Island! Master bedroom has plenty of space along with a luxury bath. There's extra space that next to the laundry could be a pantry. Laundry is inside! Enjoy your spacious patio with new screens and pavers that is in a fully Fenced big backyard! No HOA. It is close to downtown Winter Park, shopping, entertainment and award-winning restaurants, etc.

1968 King Arthurs Court, Winter Park

$499,000

2 Beds ⋅ 2.5 Baths ⋅ Cherokee Park SubDv. ⋅ 32789 Zip Code

LOCATION, LOCATION, LOCATION! Tucked in a peaceful enclave of Winter Park, this distinctive 2-bedroom, 2.5-bathroom townhome blends mid-century modern charm with contemporary functionality. This home welcomes you inside with an open-concept floor plan featuring a charming wood-burning fireplace flanked by built-in shelving and classic brick flooring that seamlessly connects the living, dining, and kitchen areas, ideal for entertaining and everyday living. The spacious layout flows into the dining and kitchen area with a breakfast bar that invites casual dining, while the kitchen is outfitted with stainless steel appliances and countertops and plenty of cabinetry. The large windows allow for abundant natural light, especially in the upstairs bedrooms, where high ceilings create a sense of openness. Each bedroom offers a plethora of storage with a private ensuite framed by unique clerestory windows, providing privacy while welcoming sunlight and complementing the beautiful wood flooring. Outside, the private backyard offers a generous patio area perfect for hosting epic BBQs or simply relaxing. Experience the best of Winter Park living with this prime location, steps away from the Winter Park Tennis Club and a short stroll to Park Avenue’s acclaimed shops and restaurants, picturesque Rollins College campus, the vibrant Winter Park Farmers' Market, and the scenic shores of Lake Virginia. This home is also a stone’s throw from the exciting up-and-coming Seven Oaks Park, a 1.5-acre green space designed to promote community and wellness through its lush landscaping and thoughtfully curated spaces. Whether you are looking for a standout addition to your investment portfolio or a place to call your own, this property offers endless possibilities. Don’t miss the opportunity to make it yours—schedule a private showing today!

1102 Azalea Lane, Winter Park

$167,000

1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code

One or more photo(s) has been virtually staged. Don't miss this INCREDIBLE OPPORTUNITY in Winter Park!!!! This 1-bedroom, 1-bathroom home is in the Stratford a Winter Park Condominium offering both convenience and a great lifestyle. Enjoy nearby shopping, dining and entertainment while being minutes away from major highway. One or more photo(s) has been virtually staged. Don't miss this incredible opportunity, schedule your showing TODAY!!!!

169 Lewfield Circle Unit 169, Winter Park

$749,000

Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Meticulously cared for Kenilworth Shores home on 89 x 115 lot. Income-producing home while you plan your dream home or investment. Quiet destination street with long-term neighbors. Track Shack does an annual run on this picturesque street. Located just minutes from Park Avenue, the home is in close proximity to the area’s best restaurants and is zoned for most desirable schools-Brookshire, Glenridge, and WPHS. Homes all around are being torn down and 4,000 square foot, 3m+ dollar homes are being built.

432 Worthington Drive, Winter Park

$450,000

4 Beds ⋅ 2 Baths ⋅ Laurel Spgs SubDv. ⋅ 32792 Zip Code

**This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome home to this updated 4-bedroom, 2-bathroom home located in the Laurel Springs community of Winter Park! Zoned for top-rated schools, this POOL corner lot home is the next best move for your family. The open concept layout invites you in with the recently updated kitchen at the heart of the home. This space features quartz countertops, stainless steel appliances including a farmhouse sink, floor to ceiling cabinetry, and breakfast bar seating. Make your way around to the family room with the fireplace as the focal point of the room and French doors leading to the outdoor space. The split floorplan features the primary bedroom off the kitchen. This great space features a beautifully updated ensuite with separate vanities and a glass front shower. Off the family room you’ll find the 3 additional great sized bedrooms with the guest bathroom tucked up to the side. Make your way out back to the showstopper of the home! This like new salt chlorinated pool (built 5 years ago) is the perfect space to entertain friends and family year-round with the spacious covered patio extending out to the private pool. Sitting on just under ¼ of an acre this fully fenced lot provides plenty of green space out back and allows space for your RV, boat, or trailer (parking area with 220 power) with no HOA! Recent upgrades include a new pool pump and pool heater with a new compressor. Location is everything with this home being minutes away from Downtown Winter Park, shopping, dining areas, University of Central Florida, and HWY 417. Schedule your private showing today!

3099 Riverbrook Drive, Winter Park

$375,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Charming 3 Bedroom / 2 Bathroom BLOCK HOME on an large CORNER LOT (.23 ACRES) with NEWER WINDOWS and an UPDATED ELECTRICAL PANEL, 2016 ROOF, BAMBOO WOOD FLOORS and MODERN BATHROOMS! The spacious living area flows naturally into the dining area and kitchen with French door access to the patio and FULLY FENCED BACKYARD. The family chef will appreciate a comfortable kitchen offering solid wood cabinetry for ample storage, STAINLESS STEEL APPLIANCES and a window over the sink that lets the light pour in. The bamboo floors continue into the bedrooms including a generous PRIMARY SUITE complete with a RENOVATED EN-SUITE BATH. Bedrooms two and three share a second full bath, also updated! The beautiful mature trees that surround this home create a park-like setting and add privacy for you to enjoy the outdoor space. There is a firepit, garden bed and shed for additional storage. No HOA and zoned for TOP RATED SCHOOLS, the friendly community of Eastbrook is located near SR 436, University Blvd and 417 and is less than 30 minutes to Downtown Orlando. Enjoy the amazing beauty and attractions that Winter Park offers from the Orlando Science Center to the Orlando Museum of Art, Leu Gardens, several lakes, parks, local restaurants, boutiques and so much more! Live, work & play in close proximity to everything you need - call today to schedule a tour!

1880 Viburnum Lane, Winter Park

$250,000

2 Beds ⋅ 2 Baths ⋅ Mead Garden Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Remodeled 2nd story, end unit, 2-bedroom, 2-bath condo in stunning Winter Park! Enjoy all the charm Winter Park has to offer, just minutes from Park Avenue's shops and restaurants, or take a short bike ride to nearby parks and outdoor venues. This desirable end-unit condo has been upgraded with new kitchen cabinets, granite countertops, and stainless steel appliances. Recent 2023 improvements include a new AC, roof & gutters. The interior has been freshly painted, and the home boasts new outlets, wall switches, and light fixtures throughout. Enjoy new luxury vinyl floors and plush carpeting, as well as all-new door hardware for a polished look. The community offers a pool and an on-site laundry facility. With Mead Gardens right behind the complex, you’ll have access to some of the best walking paths in Winter Park. Conveniently located between Trader Joe's, Winter Park Village, Ivanhoe Row, and Mills restaurants, and just a short distance to Park Avenue, Winter Park Tennis Center, Seven Oaks Park, and Rollins College. With low monthly fees, this is a fantastic opportunity to live affordably in Winter Park!

1250 S Denning Drive Unit 205, Winter Park

$675,000

3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code

Situated between tree lined Golfside Drive and the Winter Park Pines Hole 3 fairway, this updated 3-bedroom, 2-bath residence has been completely renovated. Stepping through the front door, you will find an open-concept layout that draws you into the heart of the home. Serving both form and function the engineered hardwood flooring spans the entire home. Built for entertaining, the kitchen is the focal point for all living spaces. The finely finished kitchen has sleek quartz countertops, Whirlpool appliances and a breakfast bar perfect for entertaining or casual dining. The family room is a bright space, complimented by wide double pane windows overlooking the third hole fairway and a wood-burning fireplace. Head outside and be sure to catch the breeze blowing as you relax on the the screened-in patio overlooking the recently planted pine trees along the fairway. Back inside, the Primary bedroom suite has french doors leading outside, a granite topped dual sink vanity and walk in closet. This home has been tastefully updated with notable updates including the entire kitchen, plantation shutters, flooring and neutral paint throughout. The home is zoned for Winter Park schools including Brookshire Elementary, Glenridge Middle and Winter Park High School. You won't want to miss this charming house or the chance to live in this beautiful, established neighborhood. ROOF - 2021.

1336 Golfside Drive, Winter Park

$745,000

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

Welcome to this stunning 3,400+ square foot home, nestled in the prestigious gated community of Enclave At Aloma. Offering a perfect blend of luxury and comfort, this spacious 5-bedroom, 4-full bathroom residence is designed for both entertaining and everyday living. Downstairs, a dedicated home office provides the perfect setting for remote work or quiet study. The generous floor plan allows for a large dining table with seating for 10+ people, with plenty of room to move around comfortably, making it ideal for family and friends. Whether it’s a holiday feast or a casual dinner party, this dining room offers the perfect blend of style and functionality for any occasion. The chef’s kitchen is a culinary dream, featuring stainless steel appliances, granite countertops, a large island, generous storage space, The Kitchen seamlessly flows into the expansive living room designed with an open-concept layout, it provides ample space for relaxation and entertaining. Large windows flood the room with natural light, creating a warm and welcoming atmosphere. The primary suite, located on the second floor, is a private retreat with two large walk-in closet's and an en-suite bathroom complete with a soaking tub, walk-in shower, and dual vanities. Four additional generously sized bedrooms provide plenty of space for family and guests, Step outside to your own private oasis surrounded by beautiful, meticulously maintained landscaping. The screened-in salt water pool offer's a peaceful retreat where you can relax while enjoying the Florida sunshine in complete privacy. The outdoor space also includes a lanai, ideal for unwinding after a long day. Located in a highly sought-after gated community, while being just minutes away from top-rated schools, shopping, dining, and recreational amenities. Don’t miss the opportunity to make this dream home yours!

7945 Pleasant Pine Circle, Winter Park

$1,275,000

Tuscany Place SubDv. ⋅ 32789 Zip Code

Located in the Tuscany Place neighborhood in the heart of Winter Park, this home offers endless potential for those looking to create their dream residence. With its classic ranch architecture and original features, this property is a blank canvas awaiting your personal touch, or provides a great opportunity to build new on its 0.39-acre corner lot. The home includes 3 bedrooms and 2 bathrooms, a formal living room, separate dining room, family room, sunporch, and kitchen with a breakfast nook. It also has a two-car rear entry garage. The spacious backyard provides room for outdoor gatherings and gardening, with mature landscaping. The location is excellent, within walking distance to Winter Park Racquet Club, and just moments from Winter Park and Maitland's vibrant dining, shopping, and cultural scene. Zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. This home is perfect for investors or homeowners seeking a project in a sought-after neighborhood. Being sold AS IS, please see Realtor Remarks for comments.

1001 Tuscany Place, Winter Park

$5,695,000

5 Beds ⋅ 5.5 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Welcome home to one of the most exceptional properties on the market! This gorgeous, new-construction FG Schaub custom home is the epitome of stunning contemporary design by architect, Michael Weinrich. As you enter this sprawling residence, with views of both Lake Sue and Lake Chelton you'll be greeted by exquisite tile work with brass inlays, wood floors, drop down ceiling, crown molding, wainscoting and natural light that pulls the outside living in. The first floor was meticulously designed with your Owner’s suite, an additional en suite bedroom with walk in closet, large laundry room with full size washer and dryer and an abundance of cabinet and counter space, an eye catching drop zone, elevator, storage room, kitchen and great room. The kitchen truly is a chef’s dream with Quartz countertops, spacious island, custom cabinetry with a satin brass inlay, and modern appliances including Tru refrigerator, freezer, a dual zone 150 bottle wine fridge, 60" Wolfe range with a custom range hood. The custom cabinetry continues into hidden butlers pantry complete with ice maker, microwave drawer, additional sink and Bosch dishwasher. The great room will be your hot spot for entertaining! Located off the kitchen, offering plenty of space for friends and family to gather with easy access to the pool area. Floor to ceiling Anderson windows, bar and an electric fireplace for that added touch of ambiance. Continuing into the Owner's suite you will find more expansive Anderson windows, private access to the outdoor living area, luxurious en-suite bathroom and custom closet. Feast your eyes on the 3x10 large format porcelain tile flooring, dual undermount glass sinks, 24K plated brushed gold fixtures, towel warmer, free standing soaking tub, large walk in shower and private water closet with smart toilet in your Owner’s bathroom. And the closet is a feature in itself with lighted LED rods, custom built ins, full length door mirrors and island. Access the second floor via the private elevator or staircase with a glass railing that leads to 3 additional bedrooms, all en-suite with custom tile work and walk in closets with built ins. You'll also find an additional laundry room with a stackable washer and dryer, linen closet, mechanical room and the activity space complete with wet bar and wrap around balcony with a custom glass railing offering sunsets over Lake Sue. Step outside to your own private oasis featuring a sparkling pool with 3 built in stools, sunshelf and spa, fire pit, and cabana with a full summer kitchen, roll away screens, half bathroom and an outdoor shower - ideal for weekend gatherings or relaxing evening meals poolside. Attention to detail carries out to the oversized 3-car garage which features epoxy flooring and a custom LED light design on the ceiling. While a hand crafted iron gate to the front courtyard gives a nod to Winter Parks favorite resident peacocks. A standing seam metal roof and lush landscaping adds the final aesthetic touch on this FG Schaub masterpiece.

210 Chelton Circle, Winter Park

$7,000,000

7 Beds ⋅ 5.5 Baths ⋅ N/A SubDv. ⋅ 32792 Zip Code

South Carolina "Low Country" style manor home situated on 10.52 luxurious lake front acres just 10 minutes from the heart of downtown Winter Park! From the moment you enter the private gated entrance, and cruise down the newly paved drive, you will be in awe of this impressive estate! Passing by the newly fenced green pastures, and the state of the art 10-stall center aisle barn, you will notice a quaint guest cottage, and its perfect location on these premises, tucked toward the edge of the sprawling acreage and out of the line of sight of the breathtaking beauty that is the main house. Beyond the main home you will find the serenity of a forgotten “old Florida” with stately cypress trees surrounding a lagoon with fountain and beyond, the awe-inspiring panoramic view of 400-acre Lake Howell! The Main home boasts a prestigious 3-story design featuring wrap-around balcony style porches, a third-floor balcony and a newly added ground level back porch with retractable screens overlooking a gorgeous salt-water po

1245 Howell Point, Winter Park

$409,999

2 Beds ⋅ 1 Baths ⋅ Golfview SubDv. ⋅ 32789 Zip Code

Welcome to this charming beautiful well maintained single family home located in Winter Park, FL. This home has it all! This property features a breezeway entrance / Mudroom that leads you to the front door of the home or to the door to enter the backyard. Presenting 2 bedrooms, 1 bathroom, 1 car garage shared with laundry room space, moving along to the living-room & open eat in kitchen combo. Your large backyard is fenced in to give you privacy while entertaining. It also boasts a covered patio that allows you to enjoy watching the rainfall or sip some lemonade during the sunshiny days. The owner has recently painted the entire exterior and revamped the curb appeal. This home is perfectly situated near downtown Orlando and just minutes from Dubsdread Golf Course and amazing local restaurants. Less than 30 minutes away from your funnest attractions such as Disney, Universal Studios and some great colleges !! Property is currently tenant occupied. Rest assured it’s very easy to show. Here’s your opportunity to own property in Winter Park so schedule your showing today because this won’t last! HVAC: Replaced in 2014 and outdoor unit is rebuilt in 2023 (new compressor) PLUMBING Completely re plumbed in 2009 ROOF- Replaced in 2019 ELECTRICAL replaced in 2009/ Main panel upgraded in 2017 Back Porch built in 2019/ Front Windows replaced in 2018 Exterior Completely repainted: Sept. 2024

1225 Formosa Avenue, Winter Park

$210,999

2 Beds ⋅ 2 Baths ⋅ Lancelot At Winter Park SubDv. ⋅ 32792 Zip Code

WINTER PARK CONDO! This spacious condo is located just minutes from UCF, Rollins College and Full Sail University, walking distance to shopping center and conveniently located near restaurants, major roads and highways (417 & 408). Completely renovated and ready to move into 2 bed 2 bath has NO CARPET, NEW KITCHEN CABNIETS with STAINLESS STEEL APPLIANCES, NEW VANITIES in bathrooms, BRAND NEW AC and WATER HEATER! This beautiful unit is positioned on the second floor, has inside laundry and vaulted ceiling in the great room. The spacious kitchen offers a breakfast area, pantry, and overlooks living area. Each bedroom has it's own bathroom allowing for privacy along with nice sized closets for plenty of storage. Building has fresh exterior paint and new roof. Condo has a community pool and mail center. It is a must see!

3651 N Goldenrod Road Unit 204, Winter Park

$412,000

4 Beds ⋅ 2 Baths ⋅ Ridge High Sub SubDv. ⋅ 32792 Zip Code

One or more photo(s) has been virtually staged. Welcome to this beautifully remodeled 4-bedroom, 2-bath home, nestled in a quiet neighborhood that perfectly balances comfort and convenience. As you approach, you’ll notice the fresh exterior paint and NEW ROOF, welcoming you inside where you’ll find a bright and inviting open living space, featuring brand new luxury vinyl plank flooring that flows seamlessly throughout the home. The thoughtfully designed floor plan creates a natural flow between the living, dining, and kitchen areas, making it ideal for both relaxing and entertaining. The heart of the home is a completely renovated kitchen boasting sleek quartz countertops, stainless steel appliances, and custom cabinetry. Adjacent to the kitchen is a cozy dinette area that leads into a versatile flex space, ideal for a home office, playroom, or fitness area, offering endless possibilities to suit your lifestyle needs. The split-bedroom layout ensures maximum privacy for the spacious primary suite, which is tucked away on its own side of the home just off the flex space. This retreat includes a generous walk-in closet and a stylishly renovated ensuite bathroom. On the opposite side of the home, three additional bedrooms share a beautifully updated bathroom, providing ample space for family or guests. The huge backyard offers plenty of room for outdoor activities or even adding a pool. Recent upgrades include a new roof, updated electrical, new sod, and fresh interior and exterior paint, ensuring peace of mind for the next homeowner. Located in a highly sought-after area, this home is zoned for top-rated Tuskawilla Middle School and Lake Howell High School. With easy access to Highway 436, a variety of shopping and dining options are just moments away, simplifying your daily routine. Don’t miss out on the chance to own this fully renovated gem that’s move-in ready and waiting for you to make it your own!

2140 Ridge Drive, Winter Park

$229,900

2 Beds ⋅ 2 Baths ⋅ Winter Park Villas SubDv. ⋅ 32792 Zip Code

Welcome to this charming and spacious 2-bedroom, 2-bathroom townhome nestled in the sought after Winter Park Villas community. Perfectly situated just minutes from Full Sail University and the University of Central Florida, this home is conveniently located close to shopping, restaurants and grocery stores. Less than a 5 minute drive to Winter Park Pines 18 hole Golf Course. Freshly painted throughout, as you step into this townhome you will be greeted with an airy living area highlighted by vaulted ceilings and a cozy fireplace. The open layout seamlessly connects the living room to the dining area, enhancing the flow of the space. The second floor features a generously sized primary bedroom, offering privacy and comfort, complete with a large walk in closet and en-suite. The first-floor bedroom is also spacious and provides privacy for guests, a home office, or a roommate. Other features include an inside laundry area with a washer and dryer, plus great storage with many closets throughout. As part of the Winter Park Villas community, you’ll have access to fantastic amenities, including a sparkling pool, tennis court, gym, and clubhouse. See the attached features sheet for more details. Roof - 2021, HVAC - 2017, NEW Interior Paint.

608 Montego Bay Court Unit S, Winter Park

$560,000

4 Beds ⋅ 2 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code

4 bedroom, 2 bath home set on a perfectly manicured 1/4 acre corner lot, located in the new Winter Park gated community Enclave at Aloma. Open floor plan is enhanced by the Hardwood Floors throughout living areas, volume ceilings, light and bright kitchen, family room with lots of windows, and slider that opens onto the spacious lanai. Energy efficient double pane insulated windows and high rated insulation through out the home. Perfect family home and community, excellent Seminole County Schools, minutes from 417, downtown Winter Park and Orlando. Security Video/Audio Devices Operating on Premises

Winter Park

$644,000

4 Beds ⋅ 3 Baths ⋅ Winter Woods Unit 04 SubDv. ⋅ 32792 Zip Code

Welcome Home to Winter Woods! This beautifully upgraded move in ready home at 1981 Japonica Road offers modern living with a wonderful feeling of home sweet home. Every inch of this property has been thoughtfully updated, starting with a new roof, new electrical and new windows to ensure energy efficiency and peace of mind. At first glance you will see this spectacular gourmet kitchen featuring new high-end appliances such as a LG refrigerator and stunning LG double wall oven, perfect for culinary enthusiasts. As you step inside to admire the new floors that flow throughout, creating a warm and inviting atmosphere. Outdoors, the expansive space truly shines with newly installed interlocking pavers covering 4,485 sqft, offering ample room to park up to 14 cars! Enjoy the convenience of a Level 2 EV charger and the ambiance of solar lights adorning the fence, setting the stage for evening gatherings. Whether you're hosting a large gathering or enjoying a quiet evening, this home features a new outdoor grill perfect for BBQs and entertaining. This home combines style, functionality, and luxury, making it a must-see in the desirable Winter Woods community. Truly, one-of-a-kind home, a show stopper and ready to start making memories. No HOA & Everything renovated in 2022! Don’t miss out on this exceptional property!

1981 Japonica Road, Winter Park

$509,900

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

Renovated Winter Park home offering 3 bedrooms 2 baths with 1646 sq feet. Nice size lot .24 acre, fenced with a large open pool featuring brand new pool equipment & newly screened patio. 2024 Updates include: Roof, Luxury vinyl flooring, 5 1/4 in. baseboards, popcorn ceilings removed & retextured, Full Kitchen renovation with SS appliances, Soft close cabinets & Quartz counter tops. Fresh paint, New interior doors. Electric updates with new Decora switches, & LED light fixtures. New Ceiling Fans with remote controls in every room. The Living room is anchored with a stone wood burning Fireplace with Custom Built-ins which flows to the dining room. Both bathrooms updated with Porcelain tile, new vanities & fixtures. Water Heater 2021, AC 2016 completely serviced. Gorgeous natural light throughout. New Garage Door opener with Keypad. The Shed in the backyard offers additional storage. No HOA! Highly desirable area with easy access to shopping & main roads.

1710 Aster Drive, Winter Park

$1,275,000

3 Beds ⋅ 2 Baths ⋅ Tuscany Place SubDv. ⋅ 32789 Zip Code

Located in the Tuscany Place neighborhood in the heart of Winter Park, this home offers endless potential for those looking to create their dream residence. With its classic ranch architecture and original features, this property is a blank canvas awaiting your personal touch, or provides a great opportunity to build new on its 0.39-acre corner lot. The home includes 3 bedrooms and 2 bathrooms, a formal living room, separate dining room, family room, sunporch, and kitchen with a breakfast nook. It also has a two-car rear entry garage. The spacious backyard provides room for outdoor gatherings and gardening, with mature landscaping. The location is excellent, within walking distance to Winter Park Racquet Club, and just moments from Winter Park and Maitland's vibrant dining, shopping, and cultural scene. Zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. This home is perfect for investors or homeowners seeking a project in a sought-after neighborhood. Being sold AS IS, please see Realtor Remarks for comments.

1001 Tuscany Place, Winter Park

$169,900

1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code

Lovely and updated 2nd floor 1 bed, 1 bath condo in Winter Park’s Stratford condos with in-unit laundry available now. Enjoy the security and privacy of an upper floor condo with balcony and storage closet in this well-maintained community with low HOA fees that cover 2 pools, a clubhouse, fitness center, tennis court, exterior building/ground maintenance, water, sewer, and trash. Large open plan living room (12’x18’) with ceiling fan and spacious dining room area are very welcoming with the fresh light color paint. Wood-look, wide-plank laminate flooring adds to the upscale feeling along with wood cabinets in the kitchen and the newly re-coated ceilings (no more popcorn ceilings!). Quartz countertop vanity, newer toilet, and cool subway tile surround the tub/shower combo in the updated bathroom. The bedroom is quite large too (13’x15’) and offers 2 closets, ceiling fan, and stacked washer/dryer (included). If you’re looking for an affordable, centrally located condo just minutes away from Full Sail University, UCF, Rollins College, downtown Winter Park and convenient shopping plazas (Publix is right across the street) then come see this beautiful move-in ready home in Stratford.

126 Lewfield Circle, Winter Park

$425,000

3 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 2 SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer ~ Mid century modern charm and a renovated 3BD/2BA HOME with a NEW ROOF (2021), UPDATED ELECTRICAL (2021), WATER HEATER (2021), WOOD DECK/GAZEBO w/ SOLAR LIGHTS (2022), NEW WOOD LOOKS TILE FLOORS (2022), SOLAR PANELS to keep energy costs low and a BRAND NEW FRONT DOOR (2024)! Just blocks from the YMCA and Phelps Park your Winter Park oasis sits on a spacious .27 ACRE LOT where mature trees and landscaping create a park like setting. The OPEN CONCEPT is highlighted by the many large windows for fantastic NATURAL LIGHT with a comfortable flow from the living and dining areas into the modern kitchen and cozy Florida room. The home chef will appreciate the character added by the gold hardware, stylish flooring and subway tile backsplash paired perfectly with modern STAINLESS STEEL APPLIANCES. The three bedrooms include a PRIMARY SUITE complete with another picture window, ceiling fan and private en-suite bath while the other two bedrooms share a second full bath off the hall, also updated! Host family cookouts or gather with friends in the expansive backyard, there is a newer deck and gazebo outfitted with solar lighting, a large shed for storage and you can sit around the fire pit and roast marshmallows under the stars. There is NO HOA and you are zoned for TOP-RATED SEMINOLE COUNTY SCHOOLS including LAKE HOWELL HIGH. Just minutes from Howell Branch Road, 436 and I-4, shopping, dining and so much more! This prime location has access to everything Winter Park has to offer and you even have a view of the Interlachen fireworks. Call today!

5061 Lake Howell Road, Winter Park

$749,000

3 Beds ⋅ 1 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Discover a charming, single story home in the heart of Kenilworth Shores! This inviting three-bedroom residence offers a range of possibilities—live comfortably, expand, or build your dream home on a spacious 89 x 115 lot. As you step inside, you'll be greeted by beautiful original oak wood floors and a remodeled kitchen and bathroom featuring stunning, one-of-a-kind granite countertops designed by a top designer. Natural light pours into the kitchen through newer windows, enhanced by top-of-the-line window treatments, including $5,000 worth of plantation shutters. The spacious eat-in kitchen seamlessly connects to a separate dining room, making it perfect for both casual meals and entertaining. Enjoy the large screened-in back porch—ideal for birthday parties and barbecues—where you can relax and listen to the sounds of the WPHS marching band on fall nights. The expansive, fenced backyard is ready for pets and play, complete with mature landscaping and a newer irrigation system in the front to keep it looking its best. Well water for irrigation keeps utility bill $250-300 per month. Roof replaced in 2012. AC replaced in 2017. Tree work 2017. Professional inspection 2020. Professionally cleaned front and back porches, this home is truly move-in ready. Washer and dryer 2023 may be included with the sale of the home. Nestled on a quiet street wonderful with neighbors, you’ll find a welcoming community here, enhanced by an annual run organized by Track Shack. Located just minutes from Park Avenue, this home offers convenient access to some of the area’s best restaurants and is zoned for Brookshire, Glenridge, and WPHS. With increasing demand for larger homes in the neighborhood, this property also presents an excellent income-producing investment opportunity. Don’t miss your chance to own this lovely starter home in Kenilworth Shores—where charm meets potential! <div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=fNzponPT6ou&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

432 Worthington Drive, Winter Park

$470,000

4 Beds ⋅ 3 Baths ⋅ Kings Cove SubDv. ⋅ 32792 Zip Code

LOCATION!!!This amazing single family home features 4-bed, open-concept home with a private pool located in the desirable Kings Cove neighborhood. Furniture is available for sale! Nestled on an expansive (1/3 acre) cul-de-sac lot, you’ll enjoy a host of appealing exterior updates and upgrades including NEWER ROOF (2021), new covered lanai over pool-scape and privacy-fenced backyard greenspace. Covered terrace offers an ideal spot for outdoor seating, dining and entertaining poolside; adjoining cabana bath offers added convenience. Interior design details include vaulted ceilings, wood-look tile flooring (NO CARPET throughout), and updated fixtures and finishes. Open kitchen features a serving bar, granite countertops, Shaker-style cabinetry, and stainless steel appliances. Gorgeous owner’s retreat features cathedral ceilings, direct terrace access, walk-in closet, and updated en suite bath with double-sink granite vanity, custom tiled tub and step-in shower. Exceptional location close to highly rated schools, shopping, dining, recreation and major thoroughfares. A few minutes drive to Trinity Preparatory School, the best private middle and high school in Orlando area. This home is beautiful and ready for you and your family! Schedule your Showing today or click Virtual Tour link to view a video tour.

4444 Steed Terrace, Winter Park

$300,000

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

Great value for a three bedroom home in Winter Park! This two story town home has the primary bedroom on the first floor and two generous bedrooms on the second floor. While it does need some cosmetic work, there is a new roof, new ac and newer gutters. The first floor is all ceramic tile. The upstairs bedrooms are laminate. In the upstairs bath there is a new vanity and ceramic tile flooring. This is a great value in a very convenient location. Call now for your private showing!

5466 Bracken Court, Winter Park

$140,000

Glenmoor SubDv. ⋅ 32792 Zip Code

Rare opportunity! Buildable 0.26 acre lot in Winter Park. Come with builder, investor and a dream. Vacant lot ready for a new owner. Zoned for single family home. Wonderful neighborhood of Glenmoor. Conveniently located by Aloma, 436 and a quick drive to downtown Winter Park. Bring all offers.

4427 Glenview Lane, Winter Park

$1,695,000

4 Beds ⋅ 4.5 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code

Located in the heart of Winter Park, one of Orlando’s desirable metro regions. This stunning, year-old modern home offers both style and convenience. This house sits proudly on a spacious corner lot, featuring a large front lawn and striking architectural pillars that create a grand entrance. The property boasts a durable and sleek metal roof, adding both aesthetic appeal and long-term durability. The detached garage offers privacy and quiet, while still allowing for easy access to the main house. Inside, you’ll find an open, airy layout with sleek modern finishes. The kitchen is a true chef’s dream, equipped with high-end GE Café line appliances, bright white cabinetry accented with brass and gold finishes, and a stunning backsplash that ties the entire space together. The home features scratch-resistant flooring throughout, ensuring a blend of beauty and practicality. Perfect for entertaining, the spacious kitchen island overlooks the open living and dining areas, creating a seamless flow. Step outside to enjoy a courtyard-style outdoor space, ideal for al fresco dining or relaxing after a long day. The primary bedroom, conveniently located on the main floor, offers the ultimate in privacy and tranquility. The bedroom features a large window with electronic blackout shades and a beautifully designed en-suite bathroom. The primary bath includes a luxurious soaking tub, modern non-slip tiles, and marble countertops, providing a spa-like retreat. Upstairs, the home features a common loft area, offering additional living space perfect for a cozy lounge, home office, or media room. Each upstairs bedroom is complete with its own en-suite bathroom and walk-in closet with floor-to-ceiling cabinetry, providing both luxury and ample storage. The guest bathroom is conveniently located under the staircase near the entrance, offering easy access for visitors. Located in the Winter Park neighborhood, this home combines modern elegance with a prime location close to shopping, dining, parks, and top-rated schools. With its thoughtful design, premium features, and unbeatable location, this home is a rare gem in today’s market. Don’t miss your chance to own this extraordinary property!

2435 Chantilly Avenue, Winter Park

$695,000

3 Beds ⋅ 3.5 Baths ⋅ Mondrian/Winter Park Twnhms SubDv. ⋅ 32789 Zip Code

Welcome to The Mondrian Winter Park Townhomes, an exclusive waterfront community featuring 30 stunning contemporary homes on the picturesque shores of Lake Killarney. This exceptional former model home is a true standout, boasting a wealth of high-end upgrades that set it apart from the competition. Step inside to discover a freshly painted interior adorned with modern light fixtures, stylish ceiling fans, and a premium Viking appliance package. The private, fenced rear yard adds an extra touch of outdoor tranquility. The home’s clean, contemporary design is accentuated by expansive storefront-style windows and soaring 10'6" ceilings in the great room, creating a bright and airy ambiance throughout. This thoughtfully designed floor plan features three spacious bedrooms, each showcasing engineered wood flooring and generous walk-in closets. Two of the bedrooms offer luxurious ensuite baths for added convenience. The primary bedroom includes access to a private patio complete with a summer kitchen, perfect for enjoying serene evenings or entertaining loved ones. Nestled in the heart of Winter Park, just north of downtown Orlando, this luxury waterfront community is mere minutes from the vibrant shops, dining options, and recreational activities that both Winter Park and Orlando have to offer. Enjoy breathtaking views of Lake Killarney from the newly completed dock or unwind in the lakeside pavilion as you watch the sunset. Act quickly as only one private boat slip remains! With your own slip, you can easily cruise across the lake to shop at Trader Joe's or savor a meal at Shake Shack. The community also provides convenient racks for kayaks and paddleboards, perfect for fishing, exercising, or simply soaking up the sun on the lake. Nearby Winter Park Village offers a plethora of shopping and fine dining experiences for you and your family, while the charming Farmer’s Market and the renowned Enzian Theater provide opportunities for leisurely outings and entertainment. Experience the ultimate in luxury living in this prime location, where comfort and convenience come together seamlessly. Don't miss out on this incredible opportunity! We're excited to announce that this home is available at entry-level pricing for the community, making it the perfect time to act. If you're interested in embracing a luxurious lakeside lifestyle, we encourage you to reach out to us today.

1802 Mondrian Circle, Winter Park

$140,000

3 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code

Seller Motivated! Great Beautiful and Specious Condo in Winter Park ,2nd floor and 2 Story ,3 bedroom,2 bath condo with Tile and Wood flooring. Spacious Living room with a dinning area, Close to Full Sail University, University of Central Florida, Rollins College,Orlando International Airport, Express Way 408 and 417,Baldwin Park, Downtown Orlando and Restaurants & Shopping Centers.

170 Scottsdale Square Unit 170, Winter Park

$459,900

3 Beds ⋅ 2 Baths ⋅ Georgetown Estates SubDv. ⋅ 32792 Zip Code

Crown molding throughout; chair rail in all rooms except living room; plantation shutters; gutters on roof; 4 windows replaced w/Anderson windows; vinyl & tile floorings; carpeting in bedrooms. Refrigerator in garage & all appliances remain. Newer AC with regular maintenance check twice a year; new flooring/laminate in living areas; large back yard in quiet neighborhood; close to everything. A school district; pool. Sold As-Is.

3241 Raiders Run, Winter Park

$368,000

2 Beds ⋅ 2 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

Be prepared to be impressed with this stunning ground floor unit at Winter Park’s Killarney Bay; a lakefront community. Remodeled unit!!! As you enter the home you are greeted with a spacious living room and you will notice the beautiful wood-like laminate tile throughout main areas. Living room has an electric fireplace and it has a side patio. The open kitchen features new stainless steel appliances, kitchen island, new wood shaker style cabinets, and granite countertops. There is also a dry bar with plenty of counter space, with dual beverage and wine refrigerator. Primary bedroom features a walk in closet and en-suite bathroom with a very spacious shower. Second bedroom is ample and has a nice screened-in patio. Full size laundry room with stackable washer and dryer, and a utility sink. Unit also has a tankless water system. Enjoy your views of Lake Killarney or take a walk to the community pool and enjoy the sun. Winter Park Village and many restaurants closely. Don’t miss the opportunity, come and see it.

750 Killarney Bay Court Unit 1, Winter Park

$625,000

3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 07 SubDv. ⋅ 32792 Zip Code

Location! Location! Education! Sounds like a worn out expression in Real Estate but that is Exactly what the lucky buyer gets with this Winter Park Pool home and there are probably few better with this combination in Central Florida. To start the New owners will have Private access to Lake Berry about 2 blocks away which features a Boat ramp and Fishing dock. Skiing OK. From your New home head South about 5 miuntes to popular Baldwin Park which offers many choices in restaurants, shops and recreational areas such as baseball fields, soccer fields and open areas to walk and jog.Very nice Dog park. About 6 to 8 blocks to the North is well respected Advent Health hospital. Travel about 5 minutes to Aloma and about 5 more minutes West on Aloma and you are in Downtown Winter Park. East on Aloma there are also many choices to shop and dine. Winter Park high is about 4 blocks from home. Once home for the weekend invite the family and friends to enjoy this open floor plan as they relax in the 34 x 17 Pool or perhaps mingle in the 40 x 12 screen porch as you cook at the 26 x 07 Outdoor kitchen. Do not overlook the 18 x 10 wood shed as it has electric and surround sound and certainly can be developed into office, getaway or playroom for kids with an A/C unit and some paint. A few other features include a inside Laundry room and built in pullout drawers in pantry and kitchen. Built in Hutch. Primary bedroom has sliding doors with direct access to pool. Home has been and should be about your Family gatherings as it will accommodate them Perfectly !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

1926 Natalen Road, Winter Park

$860,000

2 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Welcome to this enchanting 1935-built home nestled in the heart of Orwin Manor, a neighborhood known for its historic charm and serene ambiance and conveniently located off Orange Avenue with easy access to Park Avenue, Downtown Orlando, College Park, and Thorton Park. This charming residence features 2 spacious bedrooms and 2 bathrooms, perfect for modern living while retaining its historic allure. The original hardwood floors add warmth and character, flowing seamlessly throughout the home. The charming kitchen offers a cozy and inviting space for culinary adventures, complete with updated appliances. Gather around the wood-burning fireplace in the living room, creating the perfect setting for cozy evenings. The expansive yard provides ample space for outdoor activities and gardening. Additionally, the home boasts versatile flex spaces, ideal for a home office, a formal den, or even a nursery, ensuring it suits your lifestyle needs. This home is a true gem.

1423 Westchester Avenue, Winter Park

$275,000

2 Beds ⋅ 1 Baths ⋅ Windward Square Sec 2 SubDv. ⋅ 32792 Zip Code

Welcome to this enchanting one-story townhome, a rare gem in today's market. Nestled in the coveted Winter Park community of Windward Square, this spacious, open-concept home is perfect for both relaxation and entertaining. A wrought iron gate leads you into the large front courtyard, offering a secluded yet inviting entrance. Inside, abundant natural light floods the home through custom plantation shutters windows, creating a warm and inviting atmosphere. The thoughtfully designed living space with 5inch custom baseboards features ample storage and counter space, making the kitchen ideal for entertaining. Stainless steel appliances, granite countertops, and a stainless steel backsplash add a touch of modern elegance. Both bedrooms open onto a private back courtyard, offering endless possibilities for creating your own outdoor oasis. Additional features include a recently replaced roof 2023 and electrical panel 2023, an inside laundry room, and a utility closet on the covered and screened patio perfect for additional storage. Enjoy the community amenities, including a large pool, clubhouse, tennis court, and playground. Located just moments away from top-rated schools, universities, popular dining, shopping, and transportation options, this townhome offers the perfect combination of comfort, style, and convenience. Don't miss the opportunity to make this delightful home yours!

2634 Cayman Way, Winter Park

$380,000

3 Beds ⋅ 2 Baths ⋅ Bridgewater Ph 2 SubDv. ⋅ 32792 Zip Code

Discover the charm of 5422 S Bracken Ct, a serene 3-bedroom, 2-bathroom home nestled on a peaceful cul-de-sac in the sought-after Winter Park area. This delightful residence boasts a bright and inviting kitchen with granite counters, perfect for culinary adventures and gatherings. Step outside to the screened pool area, complete with an attached spa and covered patio, offering a private oasis and ample room for outdoor activities and relaxation year-round. Located in a prime school district and close to shopping areas, outdoor recreation activities, restaurants, and highway access, this pool home is a gem just waiting for your personal touches.

5422 S Bracken Court, Winter Park

$274,900

2 Beds ⋅ 2 Baths ⋅ Goldenrod Villas Condo SubDv. ⋅ 32792 Zip Code

Very CLEAN Move In Ready. Upgraded unit with newer high end cabinets in kitchen and both baths, Granite counters in kitchen and baths. Custom tiled backsplash, NEW carpet in both bedrooms. Features a open eat in kitchen area on one end and other has a large granite breakfast bar. Spacious open floor plan with wood laminate floors and ceramic tile in baths. This unit has walk-in closets in both the main bedroom and second bedroom. Located in the back of small neighborhood which offers quiet and private area on the end of a dead end Street. The last Street in back like this one is the newer units which have the modern open floor plan and vaulted ceilings. Very clean condo. Was just professionally cleaned top to bottom for new owners. Community has swimming pool. Convenient location to all the shops, restaurants, Full Sail and UCF. Located in a good school district. Property did not have Homestead exemption so with homestead taxes should go down.

7794 Country Place Unit 7794, Winter Park

$335,000

2 Beds ⋅ 2.5 Baths ⋅ Huntington Condo SubDv. ⋅ 32789 Zip Code

Seize the opportunity to own this delightful townhouse within walking distance of downtown Winter Park, where the charm of Park Avenue and the vibrant Rollins College campus await just steps from your door. This two-bedroom, two-and-a-half-bathroom home presents an ideal canvas for creating your haven. As you enter, you'll be welcomed by a well-planned layout featuring a spacious great room with a cozy wood-burning fireplace, perfect for gathering with friends and family. The adjacent dining area flows seamlessly into a bright sunroom, offering a versatile space that could easily function as a home office or a tranquil retreat for reading and relaxation. Upstairs, discover two generously sized bedrooms, each boasting its covered balcony where you can enjoy peaceful mornings or unwind in the evening. The primary suite is a highlight, featuring a walk-in closet and a unique loft area that provides additional storage or a private nook for relaxation. The en-suite bath adds to the convenience and comfort. Step outside to a large, private backyard patio, ideal for hosting outdoor dinners, barbecues or simply soaking up the Florida sunshine in your secluded space. The property includes a covered, assigned parking space, with additional guest parking available for visitors. On a quiet dead-end street, this townhouse offers the ease of a lock-and-leave lifestyle, allowing you to fully embrace the vibrant offerings of Winter Park, from its eclectic dining and boutique shopping to the nearby SunRail station and bustling farmer’s market. Zoned for the highly regarded Audubon K-8 and Winter Park High School, this property combines convenience with potential to create the home you've always envisioned. Don’t let this rare opportunity pass you by.

647 Huntington Avenue Unit 8, Winter Park

$2,890,000

3 Beds ⋅ 3 Baths ⋅ Landmark Winter Park Condo SubDv. ⋅ 32789 Zip Code

INTRODUCING THE COVETED CORNER PENTHOUSE UNIT IN ONE OF WINTER PARK'S LUXURY CONDO BUILDING. THE LANDMARK BUILDING IS AN AWARD WINNING LUXURY CONDO BUILDING LOCATED IN DOWNTOWN WINTER PARK. AN EXTENSIVE PRIVATE BALCONY, UNIQUE ONLY TO THE PENTHOUSE UNIT PROVIDES AN ABUNDANCE OF LIGHT AS WELL AS PANORAMIC CITY AND TREE TOP VIEWS OF DOWNTOWN WINTER PARK. AS YOU ENTER THE SECURED MAIN ENTRY GATE, YOU ARE IMMEDIATELY IMPRESSED WITH THE AWARD WINNING ARCHITECTURAL DETAILS. A MOSAIC TILE FOUNTAIN AND CEILING IS THE CENTERPIECE OF THE OPEN AIR COURTYARD WITH A BEAUTIFUL SEATING AREA WITH PRIVATE SUMMER KITCHEN FOR ALL THE RESIDENTS TO ENJOY. TAKE THE SPACIOUS ELEVATOR TO THE PENTHOUSE FLOOR WHERE YOU WILL STEP INTO YOUR PRIVATE ENTRANCE BALCONY LEADING TO YOUR FRONT DOOR, THE FIRST OF 3 BALCONIES FOR THIS RESIDENCE. AS YOU ENTER YOU IMMEDIATELY ARE IMPRESSED WITH THE ARCHITECTURAL DETAILS OF THIS HOME. THIS UNIQUE PENTHOUSE FLOORPLAN HAS ALL UPGRADES YOU WOULD EXPECT IN A LUXURY HOME. THE RESIDENCE FEATURES 3 BEDROOMS AND 3 FULL BATHROOMS. FROM THE GOURMET KITCHEN BOASTING LUXURY APPLIANCES TO THE WELL THOUGHT OUT FLOOR PLAN. ENJOY A BEAUTIFUL MEAL WITH FAMILY AND FRIENDS IN THE SPACIOUS DINING ROOM WHILE ENJOYING THE VIEWS OF WINTER PARK FROM THE FRENCH GLASS DOORS. THE LIVING ROOM FEATURES A GAS FIREPLACE, ANOTHER UNIQUE FEATURE TO THIS UNIT. HIS AND HERS SEPARATE AREAS IN THE PRIMARY BATHROOM WITH A SHARED GLASS ENCLOSED WALK IN SHOWER. BEDROOM #2 WITH ACCESS TO A FULL BATH AND BEDROOM #3 ALSO HAS ACCESS TO A FULL BATH. BEDROOM #3 IS CURRENTLY BEING USED AS AN OFFICE WITH GORGEOUS VIEWS FROM THE FRENCH GLASS DOORS LEADING TO THE EXPANSIVE BALCONY! ANOTHER UNIQUE FEATURE OF THIS RESIDENCE IS THE UNFINISHED ROOF TOP AREA THAT IS DEEDED TO THIS PENTHOUSE UNIT. AN OPPORTUNITY TO BUILD A ROOF TOP PATIO! THE LANDMARK BUILDING IS CONSIDERED ONE OF WINTER PARK’S GEM. ENJOY THE WINTER PARK LIFESTYLE WITH DINING, SHOPPING AND MANY COMMUNITY EVENTS THAT TAKE PLACE IN CENTRAL PARK. IMAGINE SITTING ON YOUR BALCONY AND WATCHING THE SUNSETS OR TREE LIGHTING CEREMONY, OBSERVING THE ANNUAL PARADE OR LISTENING TO THE ANNUAL PHILHARMONIC CONCERT FROM THE COMFORTS OF YOUR PRIVATE PENTHOUSE WHILE ENJOYING YOUR FAVORITE BEVERAGE. BE SURE TO VISIT THE LANDMARK, THE GEM OF WINTER PARK. DEEDED 2 PARKING SPACES AND A/C STORAGE UNIT. SCHEDULE YOUR PRIVATE SHOWING TODAY. THIS RESIDENCE WILL NOT LAST.

140 E Morse Boulevard Unit J, Winter Park

$815,000

3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code

Discover your dream oasis in this exquisite 3-bedroom, 2-bathroom POOL home nestled on a coveted street in Winter Park on the 3rd hole on the GOLF COURSE. With designer-inspired upgrades and custom features throughout, this home offers a truly unique and luxurious living experience. As you approach the home, you'll be immediately impressed by the charming tile work adorning the walkway and accentuating the home's exterior. Step inside to be greeted by charming features such as crown moldings, gorgeous wood-look porcelain flooring, energy efficient LED lights and designer style lighting features throughout. Immediately to the right is a nice sized office/flex space with the potential for a 4th bedroom, featuring gorgeous built ins and natural light! The heart of the home is the oversized kitchen, a chef's masterpiece featuring custom soft-close cabinets with pull-out shelves, stainless steel appliances, and an ENORMOUS ACCENTED ISLAND with storage, perfect for entertaining. The adjacent family room is equally impressive, boasting custom built-ins, a wood-burning FIREPLACE, and surround sound. Both areas flow into an oversized canyon-like patio and sparkling pool with waterfall, protected by golf ball resistant screens and windows! French doors create a seamless indoor -outdoor flow perfect for gatherings with family and friends! The primary bedroom is a spacious haven with extra seating area and a large WALK IN CLOSET (the original 4th bedroom-converted). Bathroom with gorgeous warm tone tile work and cabinetry with a large walk-in shower and designer fixtures. Second and third bedrooms provide ample space with closets and new carpeting with a 25 year warranty! For added security, cameras are installed around the exterior of the property, and the home has been freshly painted with an EXPANDED concrete driveway. Roof replaced in 2013, and the AC system was updated in 2017. The home also boasts a new STATE OF THE ART water heater. Conveniently located across the road from Cady Way Trail and near the GOLF COUNTRY CLUB, this home offers easy access to downtown Winter Park and Baldwin Park, where you'll find a vibrant array of restaurants, entertainment, and attractions. Don't miss this opportunity to own a truly exceptional property. Schedule your private tour today!

1312 Golfside Drive, Winter Park

$1,499,000

4 Beds ⋅ 3.5 Baths ⋅ Lakemont Heights SubDv. ⋅ 32792 Zip Code

Welcome to this newly completed 4-bedroom, 3.5-bathroom home, located in the Lakemont Heights neighborhood of Winter Park. Spanning 2,843 square feet and built by the renowned Barefoot Brothers Construction, this home exemplifies the warm minimalistic style, blending modern elegance with a serene ambiance. With 10-foot ceilings throughout, spacious insulated casement windows, and wide plank engineered French oak flooring, the home offers a bright and open atmosphere bathed in natural light. The inviting covered front entry leads into an expansive interior, where the kitchen is a true showpiece. Custom millwork, floor-to-ceiling inset cabinets, and a premium Thermador appliance suite set the stage for both everyday meals and gourmet entertaining. The integrated butler’s pantry, complete with a wine cooler, microwave, and built-in shelving, adds even more luxury to the space. The open floor plan seamlessly connects the kitchen to the dining and living areas, which overlook the lush backyard oasis. Step outside to the large covered lanai, featuring a built-in summer kitchen and ample space for outdoor dining. A custom pool with a water feature is surrounded by tropical landscaping and an automated sprinkler system, creating a tranquil retreat perfect for both relaxation and entertainment. The first-floor primary suite is a luxurious escape, featuring sliding glass doors that open to the backyard and a spa-inspired bathroom with a zero-entry walk-in shower, double sinks, a makeup station with an LED mirror, and a custom walk-in closet. Upstairs, you’ll find a second master suite with its own ensuite bathroom, boasting double vanities and a standing shower. Two additional upstairs bedrooms share a Jack-and-Jill bathroom, with one offering a walk-in closet and an oversized fourth bedroom/flex space complete with a large walk-in storage room. This home is designed with both style and function in mind, offering built-in shelving in the upstairs hallway, a dedicated laundry room on the main floor, and smart home wiring with integrated in-ceiling speakers and stair lights. Two AC systems—one for each floor—keep the home comfortable year-round, while the tankless water heater, gas range, spray foam insulation, and an Aerobic treatment septic system add energy efficiency and environmental sustainability. Additional highlights include a spacious two-car garage with an epoxy floor finish, a feature wall with acoustic slat wood paneling, and a tropical landscape that provides privacy and tranquility. The property backs up to a protected, non-buildable area, offering a green sanctuary that enhances your sense of peace and seclusion. Located just a short walk from Phelps Park, the YMCA, and Lakemont Elementary, and only a quick drive from Winter Park’s top shops and restaurants, this Barefoot Brothers masterpiece presents a rare opportunity to own a thoughtfully designed, luxurious home in a prime location.

1830 Pineview Circle, Winter Park

$1,495,000

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

Completely renovated to perfection in 2022, this home combines sleek, modern design with an inviting, cozy atmosphere. This is where cutting-edge style meets everyday livability, making it a home that’s as striking as it is welcoming. The heart of the home showcases stunning modern finishes: polished floors, sleek countertops with waterfall edge island, state-of-the-art appliances, and custom cabinetry that offer ample storage and blend seamlessly into the open, airy layout. The expansive living room features a sophisticated wet bar, perfect for entertaining. A wall of sliding glass doors (hurricane-rated) invites abundant natural light, seamlessly blending the indoor and outdoor spaces while bathing the room in sunlight, and is the ideal backdrop for both social gatherings and quiet moments of relaxation. The primary suite offers plush textures, soft lighting, and neutral tones that evoke a sense of serenity. Two separate walk-in closets, a dual sink floating vanity, and a large walk-in rain-head shower make it the ultimate primary suite retreat. The secondary bedrooms are spacious and the renovated secondary full and half bathrooms offer clean lines and a sophisticated look. The indoor laundry room offers a separate, tub, a front-loading washer and dryer, and a state-of-the-art steam closet. Motorized remote control blinds on windows and sliders. In addition to a covered 2-car carport with a Tesla charging station, the home boasts a 2-car garage that has been temporally transformed into a versatile home gym and flex space that is fully under air (this space is NOT included in the SF listed and garage door is still functional) The home offers a whole house Generac Generator, a tankless water heater with a softener, and a filtration system. Both currently use propane gas, but natural gas lines are in the process of being connected in the area and sellers have already paid for the connection fee. Plumbing and electric updated in 2022, AC systems replaced in 2022, roof replaced in 2021, and all windows and sliders replaced in 2022 and are Hurricane Rated. With every detail thoughtfully curated, this property is more than just a home—it's a lifestyle.

1371 Lyndale Boulevard, Winter Park

$4,100,000

5 Beds ⋅ 6 Baths ⋅ Windsong North Shore 43/74 SubDv. ⋅ 32789 Zip Code

WINDSONG - WINTER PARK – A Maroon Fine Homes masterpiece and COMPLETELY renovated in 2022. This property combines luxury, functionality, and location, making it a perfect choice for those looking to enjoy the best of Winter Park living! Five bedrooms, six baths with the amazing primary suite located on first floor and shell stone flooring though out entire home except theater room. Master suite features a luxurious bath with double vanities, separate shower and tub plus washer and dryer in large walk-in closet to save a trip to the laundry room on the other side of this 6,215 sq. ft. home. From the living room with fireplace, you enter the informal dining area, large open kitchen, and a grand family room. A gourmet kitchen offers a hidden walk-in pantry, wonderful center island with nice long counter for seating open to the family room. Kitchen includes Dacor appliances with unmatched design, American made and the preferred choice for culinary enthusiasts. An office is on the first floor off from the foyer, which leads to a butler’s pantry (with another large walk-in pantry), which is adjacent to the large laundry room with another set of washer/dryer, and a custom dog bathing area! Across from the living room is a bedroom with ensuite bathroom perfect for guests or mother-in-law needs (pocket door separates this area from living room). Additionally downstairs is a theatre room with comfy chairs for family fun nights! Just outside the theatre room is a hall bar area with subzero tall wine fridge w/2 refrigerated beverage drawers/ 2 more subzero ones, another refrigerator and freezer w/ice maker and a pool full bath just down the hall. Upstairs is an open space perfect for a library, play area, another living room, etc. and is positioned between three more bedrooms with ensuite bathrooms. To enjoy morning coffee or evening wine there are 4 porches and 2 balconies. 3 garage spaces.....2 car garage and separate 3rd garage. The lay out of this luxury home is unique as it wraps around (U shape) the pool, lanai, and outdoor kitchen. Three a/c units replaced in 2014. Large, private backyard with NO rear neighbors. Located in one of Winter Park’s most sought-after neighborhoods, Windsong offers its residents Chain of Lake Access, community pools, splash park, pontoon boat, paddleboards. Top rated schools and minutes to Park Avenue shopping and dining.

465 Genius Drive, Winter Park

$635,000

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

Lovely updated Cloister's unit with LAKE VIEW. This 2 bed 2 bath large unit offers 1267 square feet of living space. Enjoy your expansive views of the picturesque lawn, pool, and LAKE OCSEOLA. Your updated kitchen boasts beautiful upgraded granite, white solid wood cabinets, stainless steel Kitchen Aid appliances, instant hot water dispenser, Ferguson fixtures, and Casablanca fan. All the bathrooms have been updated as well with granite, glass doors, heater/exhaust fans, Ferguson fixtures and safety bars. The secondary bedroom includes a built-in queen size murphy bed for added functionality. The Bosch washer/dryer are located in the primary bedroom closet area. Add hurricane windows, Primus bump proof locks, burglar bars, a covered parking space, a 2022 CARRIER AC system to the fact that unit can be purchased FURNISHED- including high-end, newer, furnishings make this a true move-in-ready property. The Cloister's is a well manicured and maintained community, located in downtown Winter Park. It offers a heated pool, putting green, fitness center, on site manager, clubhouse, not to mention private lake front park, dock and boat slips on the Winter Park chain of lakes. All this combined with your downtown Winter Park neighborhood. Two blocks from Park Avenue shops, restaurants, Art Festivals, concerts, farmers markets, and events equals the dream lifestyle.

104 S Interlachen Avenue Unit 215D, Winter Park

$233,000

2 Beds ⋅ 2 Baths ⋅ Winter Park Villas Bldg 23 SubDv. ⋅ 32792 Zip Code

**Investment Opportunity:** (TENANT IN PLACE. UNTIL MARCH 31, 2025. DO NOT DISTURBE THE TENANT!!!) Welcome to 618 Saint Johns Ct, Winter Park, FL 32792 – Attention All investor, this property offers a solid income potential. Winter Park's high demand for rentals, combined with the area's steady appreciation, ensures long-term value. Its proximity to local universities, shopping, and medical centers makes it highly attractive to renters, offering you an excellent opportunity to generate passive income. This charming 2-bed, 2-bath condo offering 1,037 sq. ft. of well-designed living space. Built in 1981, this home combines comfort with convenience in one of Central Florida’s most desirable locations. Situated in a peaceful community, the property boasts an open floor plan, spacious bedrooms, and ample natural light. Don't miss the chance to own or invest in this fantastic Winter Park condo! More photos coming soon.

618 Saint Johns Court, Winter Park

$409,990

3 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. Welcome to 1851 Maywood Road, a beautiful 3 bedroom, 2 bathroom home located in the highly sought after city of Winter Park! With just under 1,500 SqFt of living area and almost a 1/3rd acre of land, this home features an additional LARGE PRIVATE OFFICE AREA, a NEWER HVAC SYSTEM (2023), and tons of renovations including a completely REMODELED KITCHEN (2022), NEW LUXURY VINYL PLANK FLOORING (2022), and RENOVATED BATHROOM! Let's walk through the home: as you walk through the front door, you'll notice the renovated kitchen with all modern updates, stainless steel appliances, and separate dining room space. The office space is split from the other three bedrooms and could continue to be used as an office, a den/bonus room, or even potentially converted to a FOURTH BEDROOM. After the passing the spacious living room, you'll reach the beautifully updated full bathroom with upgraded vanity, tile flooring, tiled shower, and barn door style linen closet. The three bedrooms further down the hall offer a generous amount of private living areas, with the primary bedroom additionally having its own full bathroom. As mentioned before, the yard is oversized - containing almost 1/3rd acre of land, huge backyard with mature landscaping, and 2 storage sheds (one of which with electricity). The location is amazingly convenient! You'll be in very close proximity to Historic Downtown Winter Park & Baldwin Park which offers some of Orlando's best restaurants, shopping, parks, dog parks, nature trails, museums! Fast access to highways / major roads to get around to other areas of Orlando as well. This home will not last long on the market! Call now to schedule your private showing today!

1851 Maywood Road, Winter Park

$1,579,000

4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Nestled in the heart of Winter Park's prestigious "Tree Streets" neighborhood, this exquisite residence stands as a testament to refined living and architectural splendor. This four-bedroom, four-bathroom haven seamlessly blends sophistication with comfort. As you approach the property, you're greeted by manicured landscaping that hints at the paradise awaiting within. The paved driveway leads you to a home that has been thoughtfully updated, both inside and out, with recent paint refreshing its already striking appearance. Step inside, and you'll be captivated by the wide-plank, hand-carved engineered wood flooring that flows throughout, creating a sense of warmth and continuity. The interior is a symphony of elegant design, with extensive millwork adding character and depth to every room. The heart of this home is undoubtedly the kitchen—a culinary enthusiast's dream. Boasting a large island that opens to the living room, it's an entertainer's paradise. Quartz countertops gleam under carefully placed lighting, while the gas-fueled cooktop with a vent hood stands ready for gourmet creations. A wet bar between the kitchen and dining room adds a touch of sophistication, perfect for mixing cocktails or serving hors d'oeuvres. The living room is a space of tranquility and luxury, featuring an electric fireplace and offering breathtaking views of the backyard oasis. For the oenophiles, a built-in wine closet under the stairs provides the perfect storage for your prized vintages. This home's unique layout offers the convenience of two main-level suites and two second-level suites, ensuring privacy and comfort for all. Each bedroom is a retreat unto itself, with the primary bedroom offering a particularly sumptuous escape. Step outside, and you'll find yourself in a veritable Eden. The backyard is a masterpiece of landscape design, with mature plantings providing privacy and creating a lush, secluded atmosphere. The centerpiece is undoubtedly the pool, surrounded by paving that's as practical as it is beautiful. Whether you're hosting a soirée or enjoying a quiet morning coffee, this outdoor space is your personal slice of paradise. Located in the highly desirable Winter Park area, this home offers not just luxury within its walls, but a lifestyle to match. You're just a stone's throw from the Interlachen Country Club, perfect for golf enthusiasts, and a short drive from the Winter Park Station, offering convenient transportation options. Nature lovers will appreciate the proximity to Phelps Park, while everyday conveniences are easily accessible with a nearby Publix Super Market. This isn't just a house; it's a home that whispers of lazy Sunday mornings, of laughter-filled dinner parties, and of memories waiting to be made. It's more than a listing—it's an invitation to elevate your lifestyle in one of Winter Park's most coveted neighborhoods.

1521 Magnolia Avenue, Winter Park

$749,000

4 Beds ⋅ Cherokee Park SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Highly in demand, charming and rare 2 unit duplex for sale near the “College Quarter” in Winter Park: each unit offers 2 bedrooms and 1 bath plus each side has its own laundry room with washer/dryer included. Surrounded by luxury townhomes, lakefront mansions, and located on a tree lined, brick street close to Winter Park's famed Park Ave, it’s just a short 5 to10 minute walk to the shore of beautiful Lake Virginia and Rollins College campus. White tile floors run throughout unit 1101 & terra cotta tile is in unit 1107, with plenty of light coming through the energy efficient double pane windows. Both units have access to their own private paver patio to enjoy the lovely evening weather in beautiful Winter Park. There’s plenty of off-street parking with 2 dedicated spots in front and 2+ additional dedicated parking spots in back for residents and guests as well. Great value in just the land for future development too with the availability to start fresh and build two very large townhouses for resale, each over 2,000+ sq ft and each having a 1 car garage. The back unit is currently rented for $1,800 per month with lease through May 2025. The other unit is currently vacant and can easily be shown. Too many improvements to list here, please see features/updates attachments.

1101 S Pennsylvania Avenue, Winter Park

$999,999

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

*MORE PICTURES TO COME* Welcome to your dream opportunity in Winter Park! This charming 3-bedroom, 2-bathroom home is nestled on a spacious, buildable lot, perfect for those looking to expand or create their ideal living space. The current residence features an inviting floor plan, filled with natural light and offering a cozy living area, a well-equipped kitchen, and comfortable bedrooms. The highlight of this property is the large lot, providing ample room for outdoor activities, gardening, or even the possibility of future development. The seller includes plans from a reputable local custom builder, allowing you to seamlessly design your dream home or add value with a new construction project. Situated in a treelined neighborhood, you'll enjoy easy access to Winter Park’s charming shops, restaurants, and outdoor recreation. Don’t miss this rare chance to invest in a property with both immediate comfort and exciting potential for the future!

150 Dana Way, Winter Park

$89,900

1 Baths ⋅ Colonies SubDv. ⋅ 32792 Zip Code

Under contract-accepting backup offers. This conveniently located ground-floor studio condo offers a fantastic investment opportunity. Recently painted, tiled throughout, new electric panel, washer & dryer in unit. The condo is currently tenant-occupied, generating $1,100/month in rent. This well-maintained property provides easy access to University Boulevard, UCF, and Full Sail University, making it an attractive option for investors.

7309 Daniel Webster Drive Unit 1, Winter Park

Browse All Winter Park FL Just Listed Properties for Sale

Winter Park Just Listed Real Estate