Central Florida › Orlando Metro › Orange County › Winter Park › Winter Park Pool Homes
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.
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...
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...
Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabin...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmans...
Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of chara...
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in ...
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...
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,...
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 ...
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...
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...
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...
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...
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, ...
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...
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...
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...
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...
Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-...
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...
Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined...
Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable p...
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...
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...
Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within wal...
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...
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...
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...
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...
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'...
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...
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...
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, ...
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...
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...
Under Construction. Anticipated for completion in January 2027, this new-construction luxury home in Winter Park's Kenilworth Shores neighborhood offers five bedrooms, 4....
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...
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...
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...
Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everyt...
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...
Under Construction. Nearly complete... be in for the holidays!!!!! Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringin...
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...
Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet ...
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...
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, ...
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...
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...
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 ...
Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impr...
Virtually Staged. Now offered at $1,499,000. Attractive financing opportunities may be available to qualified buyers, including preferred lender financing incentives. Set...
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...
WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an im...
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 ...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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 ...
” TURN-KEY,” “PRIVATE POOL,” “NO HOA,” “RENOVATED,” and “POSSIBLE ADU Welcome to this beautifully renovated 4-bedroom, 3-bathroom home where modern updates, exceptional ...
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...
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...
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...
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...
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 ...
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, ...
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...
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...
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...
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...
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...
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 ...
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-...
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...
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...
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...
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...
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...
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...
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...
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 ...
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...
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...
David Myers 407-801-3286
Your Winter Park Real Estate Expert