Winter Park FL. Homes For Sale

Accurate Listings Updated Every 5 Minutes

Located in Orange County, Florida, and just outside of the bustling city of Orlando, lies the town of Winter Park, where residents enjoy the beautiful scenery, fun recreation, and family-friendly community. Enjoy the peace of this suburban city, with its serene lakes and botanical gardens bringing a slow-paced atmosphere to the neighborhood. Founded as a resort community, Winter Park contains many recreational facilities, from a beach, boat launch, numerous museums, and golf courses, there is an endless array of things to do in Winter Park.

Bounded by numerous lakes, Winter Park residents enjoy boating, fishing and kayaking in vast stretches of blue water. With nature trails winding around the shores of Lake Virginia and Lake Maitland, outdoor enthusiasts enjoy biking, hiking, and observing nature along these beautiful paths. Additionally, residents will find many beautiful parks and gardens to enjoy, with Ward Park and the Mead Botanical Gardens hosting sports facilities, walking trails, and lovely scenery. Along with a vast array of recreation, Winter Park residents love the conveniences and amenities provided by the downtown district, from shopping malls, restaurants, and local cafes, you will find great shopping and dining options in the area.

There is a variety of homes in Winter Park that range anywhere from humble beach cottages to elegant lakefront mansions. This suburban residential community consists of single-family homes, large estates, and condominiums. Depending on the property’s size, location, and age, the prices range anywhere from affordable starter homes to high-end extravagant residences. There really is a home for everyone here in Winter Park, Florida.

If you would like more information regarding homes for sale in Winter Park, Florida, please allow us to assist you and contact us today.

Newest Winter Park Listings

1735 Demetree Drive, Winter Park $1,050,000

Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of estab...

4 Beds
3 Baths
Waterbridge SubDv.
32789 Zip Code

603 Carnation Drive, Winter Park $419,900

Welcome to 603 Carnation Dr in Winter Park! This 4-bedroom, 2-bathroom home offers 1,427 square feet of living space with an updated kitchen and inviting living and dinin...

4 Beds
2 Baths
Eastbrook Sub SubDv.
32792 Zip Code

506 Lander Road, Winter Park $450,000

Investor or renovation opportunity in the Winter Park High school district! This solid block home features a great location for the buyer with vision. Opportunity await...

3 Beds
2 Baths
Eastgate Sub SubDv.
32792 Zip Code

2330 Westminster Ct., Winter Park $985,000

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigne...

5 Beds
3 Baths
Glencoe Sub SubDv.
32789 Zip Code

624 Dunraven Drive, Winter Park $620,000

Welcome to this charming Winter Park home, featuring classic terrazzo floors and wonderful natural light. This home boasts a cozy wood-burning fireplace that serves as a...

3 Beds
2 Baths
Kenilworth Shores Sec 05 SubDv.
32792 Zip Code

808 Densmore Drive, Winter Park $509,999

Welcome to 808 Densmore Drive, a beautifully updated 3-bedroom, 2-bathroom pool home tucked into the established Winter Park Estates neighborhood! Blending modern farmhou...

3 Beds
2 Baths
Winter Park Estates SubDv.
32792 Zip Code

1884 Jessica Court, Winter Park $699,900

Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natu...

3 Beds
2 Baths
Waterbridge SubDv.
32789 Zip Code

1631 Hillcrest Avenue, Winter Park image

1631 Hillcrest Avenue, Winter Park $4,500,000

Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, ab...

5 Beds
6 Baths
Ellno Willo SubDv.
32789 Zip Code

1825 Whitehall Drive, Winter Park $3,195,000

1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed natural stone, a stately brick entry, and striking black-framed windows define its European-ins...

4 Beds
6 Baths
Kenilworth Shores Sec 06 SubDv.
32789 Zip Code

239 Orange Terrace Drive, Winter Park image

239 Orange Terrace Drive, Winter Park $450,000

Welcome to 239 Orange Terrace Drive! This charming 4 bedroom, 2.5 bath home offers 1,866 square feet of living space in a convenient Winter Park location. Situated on a s...

4 Beds
3 Baths
Orange Terrace SubDv.
32789 Zip Code

1458 Lone Feather Trail, Winter Park image

1458 Lone Feather Trail, Winter Park $650,000

Virtually Staged. Set within the guard-gated community of Hawk’s Crest, this inviting single-story residence offers a beautifully maintained open floor plan with more tha...

4 Beds
3 Baths
Landings At Hawks Crest SubDv.
32792 Zip Code

617 N Interlachen Avenue, Winter Park image

617 N Interlachen Avenue, Winter Park $4,695,000

Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival e...

11 Beds
8 Baths
Winter Park SubDv.
32789 Zip Code

1600 Legion Drive, Winter Park $3,495,000

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a produc...

5 Beds
6 Baths
Green Oaks Rep SubDv.
32789 Zip Code

1681 Woodland Avenue, Winter Park $2,629,000

Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, th...

5 Beds
5 Baths
Comstock Park SubDv.
32789 Zip Code

7536 Village Green Drive, Winter Park image

7536 Village Green Drive, Winter Park $479,900

Beautifully renovated home near the end of a quiet Winter Park cul-de-sac. Luxurious tile floors run throughout, paired with all-new vinyl windows, a sliding glass door,...

3 Beds
2 Baths
Village Green SubDv.
32792 Zip Code

2640 Beverly Avenue, Winter Park $305,000

Solid 1949 bungalow on a usable 50 x 150 lot (approx. 7,553 sq ft) in unincorporated Orange County with a Winter Park mailing address, just blocks from Lake Killarney. A ...

3 Beds
1 Baths
Killarney Circle SubDv.
32789 Zip Code

1939 Woodcrest Drive, Winter Park $1,349,000

Welcome to refined modern living in the heart of Winter Park. Meticulously crafted in 2020, this stunning two story residence showcases four bedrooms, three full baths, a...

4 Beds
4 Baths
Acreage SubDv.
32792 Zip Code

1445 Via Sangro Place, Winter Park image

1445 Via Sangro Place, Winter Park $1,249,000

Virtually Staged. Welcome to your dream estate inside the highly sought-after, gated enclave of Lakeside Estates in Winter Park! This magnificent 2-story residence, built...

6 Beds
6 Baths
Lakeside Estates SubDv.
32792 Zip Code

1740 Puritan Avenue, Winter Park $314,000 ▼

WINTER PARK POOL HOME PRICE IMPROVEMENT Looking for a pool home you can truly make your own? Welcome to 1740 Puritan Ave in Winter Park! This property offers an exciti...

3 Beds
2 Baths
Eastbrook Sub Unit 06 2nd Rep SubDv.
32792 Zip Code

148 Oak Grove Rd, Winter Park $320,000

Virtually Staged. Winter Park living, without the Winter Park price tag! This 3 bed, 2 bath block home has already done the big stuff for you: 2020 roof, 2020 HVAC, 2023 ...

3 Beds
2 Baths
Winter Park Oaks SubDv.
32789 Zip Code

8061 Pleasant Pine Circle, Winter Park image

8061 Pleasant Pine Circle, Winter Park $750,000

Welcome to this great 5 bedroom, 3 and a half bathroom almost 3500 square foot Winter Park home! The home not only has these spaces but also is in excellent condition wit...

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

1011 Mckean Circle, Winter Park — Wooten Built $6,000,000

Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabin...

5 Beds
7 Baths
Palmer Park SubDv.
32789 Zip Code

3409 Ferndell Drive, Winter Park $415,900

Welcome to this beautifully updated 3-bedroom, 2-bathroom home in Winter Park’s established Eastbrook community, with no HOA! New front entrance door and windows, recesse...

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

1399 Aloma Avenue, Winter Park $575,000

Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter P...

3 Beds
2 Baths
Galloway Place Rep SubDv.
32789 Zip Code

1751 Glencoe Road, Winter Park $3,390,000

Set along a picturesque brick street in Winter Park’s coveted Lake Sue District, this extraordinary residence delivers the scale, craftsmanship, and thoughtful design rar...

5 Beds
7 Baths
Forest Hills SubDv.
32789 Zip Code

2219 Winter Woods Boulevard, Winter Park image

2219 Winter Woods Boulevard, Winter Park $479,999

This 3-bedroom, 2.5-bath home offers approximately 1,776 square feet of living space on a spacious 0.24-acre lot. The two-story floor plan provides flexible living arrang...

3 Beds
3 Baths
Winter Woods Unit 01 SubDv.
32792 Zip Code

1611 Chestnut Avenue, Winter Park $985,000

Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering near...

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

1411 Devon Road, Winter Park $950,000

Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless characte...

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

1737 Indiana Avenue, Winter Park $1,399,900 ▲

WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an im...

4 Beds
4 Baths
Lawndale SubDv.
32789 Zip Code

731 Bongart Road, Winter Park $519,900

Completely Renovated Winter Park Pool Home on a Spacious Corner Lot! Discover this beautifully renovated Winter Park home featuring a spacious corner lot, private swim...

4 Beds
3 Baths
Winter Park Estates SubDv.
32792 Zip Code

2228 King Charles Court, Winter Park image

2228 King Charles Court, Winter Park $575,000

Virtually Staged. PRICED TO SELL, UNDER APPRAISED VALUE!! Come check out this GORGEOUS, SOLID 4/5 BR, 3 BA, 2,500+ sqft home in Winter Park with everything you need. This...

4 Beds
3 Baths
Winter Woods Unit 03 SubDv.
32792 Zip Code

2067 Poinciana Road, Winter Park $560,000

No need to look further! This move-in-ready 4-bedroom, 2-bathroom home in Winter Woods is ready for you! Enjoy a fenced yard, no rear neighbors, lush greenery, and privat...

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

2020 Leanne Court, Winter Park $479,900

Virtually Staged. Welcome home to 2020 Leanne Ct, a spacious pool residence offering versatile living and classic Florida charm in Winter Park! According to updated Semin...

4 Beds
3 Baths
Eastbrook Sub Unit 14 SubDv.
32792 Zip Code

518 Gilbert Road, Winter Park $649,000

Welcome to 518 Gilbert Road, a beautifully updated 3-bedroom, 2-bath pool home offering 1,573 square feet of single-story living in the desirable Winter Park Pines neighb...

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

2613 Lafayette Avenue, Winter Park image

2613 Lafayette Avenue, Winter Park $1,699,900

Under Construction. Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringing warm contemporary design and effortless living...

4 Beds
4 Baths
Charmont SubDv.
32789 Zip Code

112 Bell Place, Winter Park $575,000

Welcome to 112 Bell Place, a spacious 3-bedroom, 2-bath home offering 2,253 square feet in an established Winter Park neighborhood. Tucked away on a quiet cul-de-sac with...

3 Beds
2 Baths
Eastgate Sub SubDv.
32792 Zip Code

2322 Woodcrest Drive, Winter Park $650,000 ▼

Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a rare combination of privacy, space and neighborhood charm - all within the Kenilwo...

4 Beds
2 Baths
Kenilworth Estates 1st Add SubDv.
32792 Zip Code

310 Granada Drive, Winter Park $325,000 ▼

Welcome to 310 Granada Drive, an excellent opportunity to own a single-family home in the highly desirable Winter Park 32789 area. Situated in the established Fairview He...

3 Beds
2 Baths
Fairview Heights Rep SubDv.
32789 Zip Code

2052 Wood Thrush Lane, Winter Park image

2052 Wood Thrush Lane, Winter Park $900,000

Welcome to Waters Edge at Hawks Crest, one of Winter Park’s premier gated communities! This beautifully appointed 4-bedroom, 3-bath home offers nearly 3,000 square feet o...

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

918 Enclave Place, Winter Park $2,125,000

Pre-Construction. To be built. Buyer incentive - limited time - $50,000 cash credit at closing or $70,000 credit towards upgrades. The Hawthorn, an exceptional new custo...

5 Beds
5 Baths
The Enclave Winter Park SubDv.
32792 Zip Code

712 Baffie Avenue, Winter Park $419,900 ▼

Welcome to 712 Baffie Avenue, a charming and thoughtfully updated bungalow in one of Winter Park’s most sought-after areas. This home blends classic character with modern...

3 Beds
1 Baths
Dubsdread Heights SubDv.
32789 Zip Code

2823 Parkland Circle, Winter Park $3,250,000

JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, thi...

5 Beds
6 Baths
Lake Forest Park SubDv.
32789 Zip Code

2007 Edwin Boulevard, Winter Park $1,995,000

Virtually Staged. Pre-Construction. To be built. POOL + SAUNA • DOUBLE PRIMARY SUITES • 3-CAR GARAGE • CUSTOM NEW CONSTRUCTION IN WINTER PARK Pool, sauna, double prima...

4 Beds
4 Baths
Eastgate Sub SubDv.
32792 Zip Code

513 Dunraven Drive, Winter Park $1,950,000

Under Construction. Set in Winter Park’s desirable Kenilworth Shores, this exceptional new residence blends timeless architecture, elevated finishes and thoughtfully desi...

5 Beds
5 Baths
Kenilworth Shores Sec 03 SubDv.
32792 Zip Code

266 N Ranger Boulevard, Winter Park image

266 N Ranger Boulevard, Winter Park $724,900

FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where mode...

4 Beds
3 Baths
Winter Park Pines SubDv.
32792 Zip Code

1760 Oakhurst Avenue, Winter Park $2,500,000

Experience the pinnacle of modern luxury in this architectural masterpiece, perfectly situated in the highly coveted City of Winter Park. Boasting five bedrooms and four-...

5 Beds
5 Baths
Jenkins Second Add SubDv.
32789 Zip Code

7786 Fox Knoll Place, Winter Park $398,000 ▼

PHENOMENAL DEAL, newer updates INCLUDE: beautifully renovated 4-bedroom, 2-bathroom, two car garage home that perfectly blends modern design with everyday comfort. From ...

3 Beds
2 Baths
Bridgewater SubDv.
32792 Zip Code

1003 Golfside Drive, Winter Park $759,900 ▼

Welcome to 1003 Golfside, a fully reimagined single-story pool home in the Winter Park area, set beneath a mature oak canopy on a beautifully landscaped lot. Major update...

3 Beds
3 Baths
Golfside Sec 02 SubDv.
32792 Zip Code

1660 Orange Avenue, Winter Park $479,900

Don’t miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, conveniently located just minutes from AdventHealt...

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

2818 Ambergate Road, Winter Park $429,900

Welcome home to this charming Winter Park residence located in the desirable 32792 zip code. Nestled on a quiet street at 2818 Ambergate Road, this inviting property offe...

3 Beds
2 Baths
Winter Park Estates Sec 5 SubDv.
32792 Zip Code

1951 Winter Park Road, Winter Park image

1951 Winter Park Road, Winter Park $2,089,000

Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concepts, this Louisiana-inspired 4-bedroom, 4-bath home...

4 Beds
4 Baths
Charmont SubDv.
32789 Zip Code

532 Langholm Drive, Winter Park $2,990,000

Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-...

5 Beds
5 Baths
Kenilworth Shores Sec 01 SubDv.
32789 Zip Code

2614 Parkland Drive, Winter Park $1,890,000

PRICED BELOW APPRAISED VALUE | FULLY REMODELED WINTER PARK POOL HOME Pre-approval or proof of funds required in advance of showing. A rare opportunity to own more t...

4 Beds
4 Baths
Parklando 03 SubDv.
32789 Zip Code

7348 Grand Avenue, Winter Park $285,000

Welcome! This three-bedroom, two-bathroom home in Winter Park presents a genuine opportunity for buyers ready to reimagine this one-story residence. The open floor plan c...

3 Beds
2 Baths
Oakcrest-516 SubDv.
32792 Zip Code

5303 Pine Lily Circle, Winter Park image

5303 Pine Lily Circle, Winter Park $659,000 ▲

POOL HOME IN WINTER PARK! Beautifully maintained 2015-built one-story in the quiet, gated community of Sanctuary at Aloma, offering 2,265 sq ft with 3 spacious bedrooms, ...

3 Beds
2 Baths
Sanctuary At Aloma SubDv.
32792 Zip Code

533 Country Club Drive, Winter Park image

533 Country Club Drive, Winter Park $1,599,000

Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Sho...

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

120 Broadview Avenue, Winter Park $1,250,000

SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. ...

3 Beds
2 Baths
Killarney Estates SubDv.
32789 Zip Code

4260 Bear Gully Road, Winter Park $594,000 ▼

4 Beds
4 Baths
Bear Gully Forest SubDv.
32792 Zip Code

1742 Temple Drive, Winter Park $3,545,995 ▼

The Art of Living Well: A New Chapter at "Moon Haus" Winterpark From the moment the custom 10-foot glass pivot door swings open, you realize this is not just a house—it ...

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

555 E Lake Sue Avenue, Winter Park image

555 E Lake Sue Avenue, Winter Park $2,095,000

Welcome to the Timberlane Shores area, one of Winter Park's most desirable and established neighborhoods. This beautifully updated home sits on over a third of an acre wi...

4 Beds
4 Baths
Lake Virgina Shores SubDv.
32789 Zip Code

1517 Harmon Avenue, Winter Park $1,049,000 ▼

Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining...

4 Beds
4 Baths
Lawndale SubDv.
32789 Zip Code

1803 Barker Drive, Winter Park $2,190,000

A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning pro...

4 Beds
3 Baths
South Lakemont Shores SubDv.
32789 Zip Code

5080 Seminole Avenue, Winter Park $299,900

FULLY FURNISHED and ready for its next owner! This 3-bedroom, 2-bath Winter Park home offers an excellent combination of recent improvements, location, and flexibility. M...

3 Beds
2 Baths
Suburban Homes SubDv.
32792 Zip Code

3334 Young Street, Winter Park $469,900 ▼

This beautifully transformed 3-bedroom, 2-bathroom block home offering modern updates, quality finishes, and true move-in-ready appeal in Winter Park. This standout prope...

3 Beds
2 Baths
Winter Park Forest SubDv.
32792 Zip Code

2572 Fifeshire Drive, Winter Park $899,900 ▼

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after com...

4 Beds
3 Baths
Brookshire Heights 2nd Add SubDv.
32792 Zip Code

662 Granville Drive, Winter Park $3,495,000

Timeless elegance meets effortless modern living in this exceptional five-bedroom, 5.5-bath residence in Park Grove, one of Winter Park's most coveted neighborhoods. Desi...

5 Beds
6 Baths
Park Grove SubDv.
32789 Zip Code

1166 Palmer Avenue, Winter Park $5,500,000

Pre-Construction. To be built. PRE-CONSTRUCTION: Introducing an exceptional new construction residence by Nautilus Homes, ideally positioned in the heart of Winter Park n...

5 Beds
7 Baths
Palmer Ave Lakeside Prop SubDv.
32789 Zip Code

2215 Woodcrest Drive, Winter Park $637,500 ▼

PRICE JUST REDUCED!! Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully ha...

4 Beds
2 Baths
Kenilworth Estates 1st Add SubDv.
32792 Zip Code

1386 Clematis Lane, Winter Park $427,000

LOCATION! LOCATION! Winter Park property located in Seminole County. Proximity to Rollins, Full Sail, UCF, and Valencia colleges. Great income producer, with "Flex Space"...

4 Beds
3 Baths
Eastbrook Sub Unit 06 SubDv.
32792 Zip Code

2345 Brookshire Avenue, Winter Park image

2345 Brookshire Avenue, Winter Park $825,000 ▼

Welcome to this beautiful Winter Park home where a flagstone, ivy-lined entry sets the tone for the inviting spaces found within. Tucked away on a private .21-acre lot, t...

3 Beds
3 Baths
Brookshire Heights SubDv.
32792 Zip Code

3209 Heartwood Avenue, Winter Park image

3209 Heartwood Avenue, Winter Park $439,900 ▼

Completely refreshed and ready to enjoy. This home features an updated kitchen with new appliances, stylish tile flooring throughout the main living areas, and an open fl...

4 Beds
2 Baths
Bel Aire Pines SubDv.
32792 Zip Code

1271 Palmer Avenue, Winter Park $2,125,000 ▼

Set on a generous corner lot, this stunning single-story pool home in Winter Park has been beautifully remodeled and offers the kind of effortless, one-level living that'...

4 Beds
5 Baths
J Kronenberger Sub SubDv.
32789 Zip Code

2119 Howard Drive, Winter Park $3,195,000

Pre-Construction. To be built. A striking new custom residence by FG Schaub Custom Homes, located at 2119 Howard Drive in Winter Park. This exceptional 5-bedroom, 5.5-bat...

5 Beds
6 Baths
Timberlane SubDv.
32789 Zip Code

618 Blairshire Circle, Winter Park image

618 Blairshire Circle, Winter Park $875,000 ▼

Virtually Staged. FULLY RENOVATED 4-BEDROOM, 3-BATH POOL HOME IN THE HEART OF WINTER PARK! this beautifully updated home sits on a spacious 9,915-square-foot lot surroun...

4 Beds
3 Baths
Brookshire Heights 4th Add SubDv.
32792 Zip Code

2301 Conifer Avenue, Winter Park $405,000 ▼

VIRTUALLY STAGED! EXCEPTIONAL POOL HOME IN EASTBROOK! Welcome to Conifer Avenue, where pride of ownership, and an unbeatable Winter Park-area location come together beaut...

4 Beds
2 Baths
Eastbrook Sub Unit 16 SubDv.
32792 Zip Code

913 Moss Lane, Winter Park $950,000

913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park...

3 Beds
2 Baths
Maitland Shores First Add SubDv.
32789 Zip Code

540 N Pennsylvania Avenue, Winter Park image

540 N Pennsylvania Avenue, Winter Park $3,950,000

Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density R...

4 Beds
2 Baths
Winter Park SubDv.
32789 Zip Code

2410 Sherbrooke Road, Winter Park $769,000 ▼

Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car g...

4 Beds
3 Baths
Sherbrooke SubDv.
32792 Zip Code

825 Palmer Avenue, Winter Park $5,195,900 ▲

Pre-Construction. To be built. A rare convergence of timeless French Country architecture, brand-new custom construction, and coveted access to the Winter Park Chain of L...

5 Beds
7 Baths
J Kronenberger Sub SubDv.
32789 Zip Code

1773 Walnut Avenue, Winter Park $2,725,000

Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined...

5 Beds
5 Baths
Conwill Estates SubDv.
32789 Zip Code

2622 Lake Howell Lane, Winter Park image

2622 Lake Howell Lane, Winter Park $3,750,000

Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in ...

4 Beds
3 Baths
Acreage & Unrec SubDv.
32792 Zip Code

1257 Wading Waters Circle, Winter Park image

1257 Wading Waters Circle, Winter Park $1,550,000 ▼

Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most ...

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

2260 Coldstream Drive, Winter Park image

2260 Coldstream Drive, Winter Park $675,000 ▼

Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can ...

4 Beds
2 Baths
Brookshire Heights SubDv.
32792 Zip Code

698 N New York Avenue, Winter Park image

698 N New York Avenue, Winter Park $6,195,000 ▼

Brand new 2026 custom residence in the heart of downtown Winter Park, just completed and showcasing elevated finishes thoughtfully curated by FG Schaub Construction & SOC...

5 Beds
6 Baths
Greens/Pk SubDv.
32789 Zip Code

2661 Via Tuscany, Winter Park $5,500,000 ▼

Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordina...

4 Beds
5 Baths
Maitland Shores First Add SubDv.
32789 Zip Code

2626 Ambergate Road, Winter Park $380,000

Mid-century style meets modern convenience in this beautifully updated Winter Park home, offering a move in opportunity with no HOA. Extensively improved since 2022, the ...

3 Beds
1 Baths
Winter Park Estates SubDv.
32792 Zip Code

508 Brechin Drive, Winter Park $609,000 ▼

Renovated and move-in ready, this updated Winter Park home offers a fresh, modern interior without the hassle of renovations. The brand-new kitchen features new cabinetry...

3 Beds
2 Baths
Kenilworth Shores Sec 01 SubDv.
32792 Zip Code

1922 Hammerlin Avenue, Winter Park image

1922 Hammerlin Avenue, Winter Park $1,095,000 ▲

WELCOME TO CONTEMPORARY LUXURY IN THE HEART OF WINTER PARK! This stunning two-story pool residence has been beautifully remodeled from top to bottom and offers high end d...

3 Beds
3 Baths
Edgewood Sub SubDv.
32789 Zip Code

901 Golfview Terrace, Winter Park $6,995,000

Gorgeous custom five-bedroom, five-and-one-half-bath residence built by Maroon Fine Homes in 2023 and ideally positioned on arguably one of the most sought after location...

5 Beds
6 Baths
Golfview Terrace SubDv.
32789 Zip Code

1320 Orchid Avenue, Winter Park $1,350,000

Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Or...

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

3020 Nicholson Drive, Winter Park $470,000 ▼

UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, a...

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

4039 Cool Water Court, Winter Park image

4039 Cool Water Court, Winter Park $739,777

Welcome to Lake Waunatta Woods, where neighbors become family. It is rare to find an exclusive, tight-knit community where neighbors look out for one another, and friends...

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

1850 Bryan Avenue, Winter Park $699,000 ▼

Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors f...

3 Beds
2 Baths
Lakeview Terrace SubDv.
32789 Zip Code

702 Via Bella, Winter Park $4,250,000 ▼

Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmans...

4 Beds
6 Baths
Palmer Ave Lakeside Prop SubDv.
32789 Zip Code

443 Broadview Avenue, Winter Park $999,000 ▼

A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one hom...

4 Beds
3 Baths
Killarney Estates SubDv.
32789 Zip Code

471 Holt Avenue, Winter Park $925,000 ▼

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential. THIS HOUSE IS AVAILABLE FOR LEASING OPTION. Discover the opportunity to own a versatile prop...

4 Beds
3 Baths
Winter Park SubDv.
32789 Zip Code

1220 Howell Branch Road, Winter Park image

1220 Howell Branch Road, Winter Park $950,000 ▼

A RARE WINTER PARK RENOVATION OPPORTUNITY DIRECTLY ACROSS FROM HOWELL BRANCH PRESERVE! Situated on an approximately 0.23-acre lot, this distinctive 3-bedroom, 2-bath home...

3 Beds
2 Baths
Lake Maitland SubDv.
32789 Zip Code

2430 Chantilly Avenue, Winter Park image

2430 Chantilly Avenue, Winter Park $1,550,000 ▼

Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impr...

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

3302 Royal Street, Winter Park $269,900 ▼

Come see this 3 bedroom 2 bath split plan home. All tile throughout home. Granite kitchen countertops. Eat in area in kitchen. Kitchen bar opens to great room. Huge cor...

3 Beds
2 Baths
Coronation Add SubDv.
32792 Zip Code

2207 Kindel Avenue, Winter Park $1,600,000

WELCOME TO LAKEFRONT LUXURY ON LAKE BELL. This exceptional custom residence brings together refined craftsmanship and design, and an extraordinary waterfront setting in t...