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Central Florida › Orlando Metro › Orange County › Winter Park › Winter Park Pool Homes

Winter Park Pool Homes for Sale

Florida's nearly year round warm weather makes a pool a must have feature for many Florida home buyers. Winter Park offers many homes that feature a private swimming pool and/or spa. Below is a list of all currently available pool homes in Winter Park.

Winter Park Pool Homes for Sale

1260 Alabama Drive, Winter Park image
1260 Alabama Drive, Winter Park $6,900,000

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent mas...

  • 6 Beds
  • 7 Baths
  • J Kronenberger Sub SubDv.
  • 32789 Zip Code
901 Golfview Terrace, Winter Park image
901 Golfview Terrace, Winter Park $6,795,000 ▼

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
1011 Mckean Circle, Winter Park image
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
1571 Woodland Avenue, Winter Park image
1571 Woodland Avenue, Winter Park $6,000,000

Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square f...

  • 5 Beds
  • 8 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
1200 Via Salerno, Winter Park image
1200 Via Salerno, Winter Park $5,995,000

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live...

  • 5 Beds
  • 6 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
698 N New York Avenue, Winter Park image
698 N New York Avenue, Winter Park $5,995,000 ▼

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
2228 Azalea Place, Winter Park image
2228 Azalea Place, Winter Park $5,600,000

Virtually Staged. This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a l...

  • 5 Beds
  • 6 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
1166 Palmer Avenue, Winter Park image
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
2661 Via Tuscany, Winter Park image
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
825 Palmer Avenue, Winter Park image
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
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
231 Chelton Circle, Winter Park image
231 Chelton Circle, Winter Park $4,500,000 ▼

Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury...

  • 4 Beds
  • 7 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
857 Brock Street, Winter Park image
857 Brock Street, Winter Park $4,350,000 ▼

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind...

  • 5 Beds
  • 6 Baths
  • Park Grove SubDv.
  • 32789 Zip Code
702 Via Bella, Winter Park image
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
620 Virginia Drive, Winter Park image
620 Virginia Drive, Winter Park $3,890,000

Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of chara...

  • 6 Beds
  • 5 Baths
  • Timberlane Shores 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
276 Detmar Drive, Winter Park image
276 Detmar Drive, Winter Park $3,600,000

Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with excep...

  • 4 Beds
  • 5 Baths
  • Detmar Terrace Winter Park SubDv.
  • 32789 Zip Code
1441 Cardinal Court, Winter Park image
1441 Cardinal Court, Winter Park $3,600,000 ▼

Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style,...

  • 4 Beds
  • 6 Baths
  • Winflor Court Pt Rep SubDv.
  • 32789 Zip Code
1742 Temple Drive, Winter Park image
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
2240 Venetian Way, Winter Park image
2240 Venetian Way, Winter Park $3,500,000

Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Ch...

  • 4 Beds
  • 4 Baths
  • Maitland Shores 1st Add SubDv.
  • 32789 Zip Code
1600 Legion Drive, Winter Park image
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
662 Granville Drive, Winter Park image
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
1751 Glencoe Road, Winter Park image
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
1761 Legion Drive, Winter Park image
1761 Legion Drive, Winter Park $3,265,000

One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, ...

  • 5 Beds
  • 6 Baths
  • Green Oaks Rep 02 SubDv.
  • 32789 Zip Code
2823 Parkland Circle, Winter Park image
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
1825 Whitehall Drive, Winter Park image
1825 Whitehall Drive, Winter Park $3,195,000

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

  • 4 Beds
  • 6 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
2119 Howard Drive, Winter Park image
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
1836 Whitehall Drive, Winter Park image
1836 Whitehall Drive, Winter Park $2,995,000 ▼

Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perc...

  • 5 Beds
  • 7 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
532 Langholm Drive, Winter Park image
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
1821 Englewood Road, Winter Park image
1821 Englewood Road, Winter Park $2,950,000 ▼

This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues t...

  • 5 Beds
  • 6 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
1773 Walnut Avenue, Winter Park image
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
648 Worthington Drive, Winter Park image
648 Worthington Drive, Winter Park $2,700,000

Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable p...

  • 5 Beds
  • 5 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
1681 Woodland Avenue, Winter Park image
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
1823 Sunset Drive, Winter Park image
1823 Sunset Drive, Winter Park $2,549,000

Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of time...

  • 5 Beds
  • 5 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
450 Lakewood Drive, Winter Park image
450 Lakewood Drive, Winter Park $2,500,000

Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within wal...

  • 5 Beds
  • 6 Baths
  • Osceola Shores Sec 03 SubDv.
  • 32789 Zip Code
938 Enclave Place, Winter Park image
938 Enclave Place, Winter Park $2,300,000 ▲

Pre-Construction. To be built. Buyer incentive - limited time- $50,000 cash credit at closing or $70,000 credit towards upgrades. Thoughtfully designed with a refined co...

  • 5 Beds
  • 5 Baths
  • The Enclave Winter Park SubDv.
  • 32792 Zip Code
1840 Laurel Road, Winter Park image
1840 Laurel Road, Winter Park $2,299,000 ▲

Under Construction. Be in for the Holidays!!! Experience modern luxury in this exceptional new construction residence by LUIH Luxury Homes, scheduled for completion in De...

  • 5 Beds
  • 5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
930 Enclave Place, Winter Park image
930 Enclave Place, Winter Park $2,275,000 ▲

Pre-Construction. To be built. Buyer incentive - limited time - $50,000 cash credit at closing or $70,000 credit towards upgrades. Lot 19 at 930 Enclave Place presents a...

  • 5 Beds
  • 5 Baths
  • The Enclave Winter Park SubDv.
  • 32792 Zip Code
918 Enclave Place, Winter Park image
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
1271 Palmer Avenue, Winter Park image
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
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
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
914 Enclave Place, Winter Park image
914 Enclave Place, Winter Park $2,070,000 ▲

Pre-Construction. To be built. Buyer incentive - $50,000 cash credit at closing or $70,000 credit towards upgrades. Inspired by the timeless architecture of Alys Beach, ...

  • 5 Beds
  • 5 Baths
  • The Enclave Winter Park SubDv.
  • 32792 Zip Code
240 N Phelps Avenue, Winter Park image
240 N Phelps Avenue, Winter Park $1,999,900 ▼

A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desira...

  • 5 Beds
  • 5 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
2007 Edwin Boulevard, Winter Park image
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 image
513 Dunraven Drive, Winter Park $1,950,000

Under Construction. Anticipated for completion in January 2027, this new-construction luxury home in Winter Park's Kenilworth Shores neighborhood offers five bedrooms, 4....

  • 5 Beds
  • 5 Baths
  • Kenilworth Shores Sec 03 SubDv.
  • 32792 Zip Code
2614 Parkland Drive, Winter Park image
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
751 Pansy Avenue, Winter Park image
751 Pansy Avenue, Winter Park $1,875,000 ▼

Set along one of Winter Park’s charming brick streets just steps from Park Avenue, this beautifully maintained home pairs refined design with an exceptional location. Imp...

  • 3 Beds
  • 4 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
281 Brewer Avenue, Winter Park image
281 Brewer Avenue, Winter Park $1,800,000

Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers mar...

  • 5 Beds
  • 5 Baths
  • Osceola Shores Sec 02 SubDv.
  • 32789 Zip Code
1840 Anzle Avenue, Winter Park image
1840 Anzle Avenue, Winter Park $1,750,000

Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everyt...

  • 4 Beds
  • 3 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
1840 Bryan Avenue, Winter Park image
1840 Bryan Avenue, Winter Park $1,725,000

Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests on an expansive double lot in the highly sought-after Lakeview Terrace community...

  • 4 Beds
  • 4 Baths
  • Lakeview Terrace SubDv.
  • 32789 Zip Code
2613 Lafayette Avenue, Winter Park image
2613 Lafayette Avenue, Winter Park $1,699,900

Under Construction. Nearly complete... be in for the holidays!!!!! Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringin...

  • 4 Beds
  • 4 Baths
  • Charmont SubDv.
  • 32789 Zip Code
2343 Versailles Avenue, Winter Park image
2343 Versailles Avenue, Winter Park $1,699,000 ▼

This modern and sleek Winter Park residence, with over $130K of improvements, is tucked along a quiet dead-end street, offering a functional, open floorplan in an excepti...

  • 4 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
2308 Mulbry Drive, Winter Park image
2308 Mulbry Drive, Winter Park $1,699,000

Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet ...

  • 4 Beds
  • 4 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
2407 Lafayette Avenue, Winter Park image
2407 Lafayette Avenue, Winter Park $1,625,000

Discover this exceptional custom-designed modern pool home, ideally situated in one of Winter Park's most sought-after neighborhoods. Located on a quiet street, this spac...

  • 5 Beds
  • 5 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
250 Killarney, Winter Park image
250 Killarney, Winter Park $1,600,000

This home is an adorable 4 Bed 3.5 Bath Home in the heart of Winter Park. You will feel right at home the moment you step in. lovely kitchen showcases gorgeous cabinets, ...

  • 4 Beds
  • 4 Baths
  • Killarney Estates SubDv.
  • 32789 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
1864 Grinnell Terrace, Winter Park image
1864 Grinnell Terrace, Winter Park $1,599,000

Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern in...

  • 5 Beds
  • 4 Baths
  • Fremar SubDv.
  • 32789 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
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
641 Northwood Circle, Winter Park image
641 Northwood Circle, Winter Park $1,499,000 ▼

Virtually Staged. Now offered at $1,499,000. Attractive financing opportunities may be available to qualified buyers, including preferred lender financing incentives. Set...

  • 3 Beds
  • 5 Baths
  • Winter Park Oasis SubDv.
  • 32789 Zip Code
1570 Palmer Avenue, Winter Park image
1570 Palmer Avenue, Winter Park $1,485,000 ▼

Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functiona...

  • 4 Beds
  • 4 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
1737 Indiana Avenue, Winter Park image
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
1473 Berkshire Avenue, Winter Park image
1473 Berkshire Avenue, Winter Park $1,369,000 ▼

LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 ...

  • 5 Beds
  • 4 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
1939 Woodcrest Drive, Winter Park image
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
102 Bell Place, Winter Park image
102 Bell Place, Winter Park $1,299,000 ▼

Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for su...

  • 4 Beds
  • 4 Baths
  • Eastgate Sub SubDv.
  • 32792 Zip Code
2015 Summerfield Road, Winter Park image
2015 Summerfield Road, Winter Park $1,250,000 ▼

Recently appraised at $1,250,000! Welcome to one of Winter Park’s most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Co...

  • 4 Beds
  • 4 Baths
  • Kenilworth Shores Sec 07 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
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
1735 Demetree Drive, Winter Park image
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
1448 Lake Florence Way, Winter Park image
1448 Lake Florence Way, Winter Park $1,049,900 ▼

Located in an intimate gated community of just 28 homes and minutes from Downtown Winter Park, this exceptional former K. Hovnanian model home features over $200,000 in b...

  • 5 Beds
  • 5 Baths
  • Lake Florence Preserve SubDv.
  • 32792 Zip Code
616 Brechin Drive, Winter Park image
616 Brechin Drive, Winter Park $999,000 ▼

Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completel...

  • 4 Beds
  • 5 Baths
  • Kenilworth Shores Sec 04 SubDv.
  • 32792 Zip Code
1411 Devon Road, Winter Park image
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
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
338 Blue Heron Drive, Winter Park image
338 Blue Heron Drive, Winter Park $836,000 ▼

Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character an...

  • 3 Beds
  • 3 Baths
  • Flamingo Shores SubDv.
  • 32789 Zip Code
1521 Heron Wood Place, Winter Park image
1521 Heron Wood Place, Winter Park $829,500 ▼

A unique opportunity with two separate structures on one parcel! The main home provides comfortable living, while the second building was previously licensed and used as ...

  • 4 Beds
  • 2 Baths
  • 32792 Zip Code
722 S Ranger Boulevard, Winter Park image
722 S Ranger Boulevard, Winter Park $775,000 ▼

” TURN-KEY,” “PRIVATE POOL,” “NO HOA,” “RENOVATED,” and “POSSIBLE ADU Welcome to this beautifully renovated 4-bedroom, 3-bathroom home where modern updates, exceptional ...

  • 4 Beds
  • 3 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
1003 Golfside Drive, Winter Park image
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
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
1884 Jessica Court, Winter Park image
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
715 S Ranger Boulevard, Winter Park image
715 S Ranger Boulevard, Winter Park $695,000

Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet...

  • 4 Beds
  • 3 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
274 N Ranger Boulevard, Winter Park image
274 N Ranger Boulevard, Winter Park $659,900 ▼

Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! From the moment you enter, you will ...

  • 3 Beds
  • 2 Baths
  • Winter Park Pines 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
2322 Woodcrest Drive, Winter Park image
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
518 Gilbert Road, Winter Park image
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
2215 Woodcrest Drive, Winter Park image
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
1016 Aragon Avenue, Winter Park image
1016 Aragon Avenue, Winter Park $625,000 ▼

This duplex "Investment Opportunity" is centrally located on a quiet, tree-lined brick street. It has 2 units. Each unit has two Bedrooms, a "Jack & Jill" bath, and a hal...

  • 4 Beds
  • 4 Baths
  • Seville Park SubDv.
  • 32789 Zip Code
2758 Banchory Road, Winter Park image
2758 Banchory Road, Winter Park $619,500 ▼

FULLY PAID SOLAR PANELS INCLUDED — NO SOLAR LOAN TO ASSUME! A rare added value for the next owner: enjoy the benefits of solar energy with the system included in the sale...

  • 3 Beds
  • 3 Baths
  • Winter Park Pines SubDv.
  • 32792 Zip Code
4026 Tenita Drive, Winter Park image
4026 Tenita Drive, Winter Park $599,000

MOVE IN READY! New roof, new bathrooms, new kitchen, new floors, new electrical panels and more. Located in the beautiful lake community of Lake Waunatta Woods. Large ...

  • 3 Beds
  • 2 Baths
  • Lake Waunatta Wods SubDv.
  • 32792 Zip Code
7525 Lodge Pole Trail, Winter Park image
7525 Lodge Pole Trail, Winter Park $575,000 ▼

Welcome to this fully renovated four-bedroom, two-bathroom pool home offering close to 2,000 square feet of beautifully updated living space on an expansive .36-acre pie-...

  • 4 Beds
  • 2 Baths
  • Arrowhead Cove SubDv.
  • 32792 Zip Code
2627 Ambergate Road, Winter Park image
2627 Ambergate Road, Winter Park $530,000 ▼

Welcome home to this beautifully presented 4-bedroom, 3-bath home located in Winter Park Estates. Offering a comfortable single-story layout and solid block construction...

  • 4 Beds
  • 3 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
2641 Carvell Court, Winter Park image
2641 Carvell Court, Winter Park $525,000 ▼

WINTER PARK POOL HOME • NO HOA • OVER 2,100 SQ FT • NOW $525,000! Looking for space, a private pool and the freedom of no HOA — all in Winter Park? Welcome to 2641 Car...

  • 4 Beds
  • 2 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
1905 Bonanza Ct, Winter Park image
1905 Bonanza Ct, Winter Park $520,000

Enjoy the Florida lifestyle in this beautifully maintained SINGLE-STORY HOME, ideally positioned on a quiet roundabout with a spacious layout and impressive outdoor ameni...

  • 4 Beds
  • 2 Baths
  • Eastbrook Sub Unit 13 SubDv.
  • 32792 Zip Code
731 Bongart Road, Winter Park image
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
808 Densmore Drive, Winter Park image
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
2054 Eastbrook Boulevard, Winter Park image
2054 Eastbrook Boulevard, Winter Park $500,000

Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced b...

  • 4 Beds
  • 3 Baths
  • Eastbrook Sub Unit 8 SubDv.
  • 32792 Zip Code
5316 Halyard Court, Winter Park image
5316 Halyard Court, Winter Park $495,000

Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finish...

  • 3 Beds
  • 2 Baths
  • Woodcrest Unit 5 SubDv.
  • 32792 Zip Code
2217 Sussex Road, Winter Park image
2217 Sussex Road, Winter Park $485,000 ▼

NEW FLOORS, POOL, NO HOA, 4-YEAR-OLD ROOF & NEWER A/C!** Move-in ready 4-bedroom + office home offering 2,092 SF in the desirable Winter Woods/Lake Howell area of Winter ...

  • 4 Beds
  • 2 Baths
  • Winter Woods Unit 01 SubDv.
  • 32792 Zip Code
3020 Nicholson Drive, Winter Park image
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
2020 Leanne Court, Winter Park image
2020 Leanne Court, Winter Park $469,900 ▼

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
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