Winter Park Pool Homes for Sale

Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer repr...

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...

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...

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...

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 large, elevated cor...

Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportun...

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...

There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the pro...

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winni...

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,...

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 ...

Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully craft...

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...

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...

Perfectly positioned in the heart of Old Winter Park, the quaint Forrest Hills neighborhood is lined with charming cobblestone streets that wind around Lake Sue. This cus...

One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly...

Virtually Staged. This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single l...

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, ...

Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a ...

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...

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

Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orl...

Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredibl...

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. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...

Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...

Pre-Construction. To be built. Welcome to The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 thoughtfully crafted residences by FG...

Under Construction. Experience modern luxury in this exceptional new construction residence by LUIH Luxury Homes, scheduled for completion in December 2026.Offering 5 bed...

Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...

Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends...

Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, feat...

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...

Thoughtfully designed with an uncompromising commitment to quality, craftsmanship, and detail, this exceptional new construction residence is an expression of luxury livi...

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...

Set along a charming, tree-lined street in Winter Park, this stunning new construction home brings together modern farmhouse character, thoughtfully designed interiors, a...

Built in 2017 and thoughtfully enhanced with over $130K in recent improvements, this modern and sleek Winter Park residence is tucked along a quiet dead-end street, offer...

Under Construction. LUXURY NEW CONSTRUCTION IN WINTER PARK'S HIGHLY SOUGHT-AFTER TREE STREETS! Welcome to 1550 Palm Avenue, a thoughtfully designed new residence by LUIH ...

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...

A PRIVATE BALINESE RESORT IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park Avenue Welcome to a rare offering where ...

Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom...

Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come toget...

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

Under Construction. Currently under construction by LUIH Luxury Homes, this exceptional new construction residence is anticipated for completion in November 2026 and brin...

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...

Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. T...

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

Available furnished or unfurnished, lease-to-own or straight lease (6-12 months). On a picturesque brick street in Winter Park, this beautifully designed modern traditio...

Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park...

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...

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...

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 ...

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, ...

Virtually Staged. 641 Northwood Circle is a rare opportunity to own newer construction in the heart of Winter Park at a newly repositioned price of $1,599,000. Tucked wit...

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...

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

A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Su...

New Construction! New photos coming soon! First photo is a rendering of the new home and the following photos are interiors of a similar model by the builder. Discover Mo...

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exc...

Under Construction. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunni...

BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern desi...

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

Virtually Staged. Welcome to your dream home in the highly sought-after Lakeside Estates neighborhood in Winter Park! This elegant 6-bedroom, 5-bathroom, 2 laundry rooms ...

Welcome to an exceptional opportunity in Waters Edge at Hawks Crest, one of Winter Park's premier gated, resort-style communities. Positioned on a desirable premium lot w...

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...

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...

Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated,...

Welcome to this charming 3 bedroom, 2 bath home located in the highly desirable area of Winter Park. Situated on an oversized lot, this property offers both comfort and s...

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...

A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN b...

Virtually Staged. Set on nearly an acre in Winter Park, this stately two-story home offers five bedrooms and three and a half bathrooms across more than 3,200 square feet...

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 ...

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...

Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranqu...

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

Virtually Staged. Nestled on an OVERSIZED HOMESITE of well over half an acre in the sought-after Lake Ann Estates of Winter Park, this BEAUTIFULLY UPDATED 4-bedroom, 3-ba...

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...

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 ...

Welcome to 2333 Westminster Court, a stunningly reimagined residence that perfectly captures the effortless elegance of Winter Park living. A thoughtful and meticulous re...

This "Investment Opportunity" duplex is centrally located on a quiet, tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Me...

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...

Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated fr...

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-...

MOTIVATED SELLER – QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove community of Winter Park. From the mom...

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 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...

Modern Ranch Gem on a Corner Lot | 4 Bed | 2 Bath | 2,126 Sq Ft | Screened Pool | No HOA | Winter Park, FL Welcome to this beautiful 4-bedroom, 2-bathroom ranch-style ...

Welcome to this beautifully updated 4-bedroom, 2-bath pool home located in the highly desirable Winter Woods community of Winter Park. From the moment you step inside, yo...

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, ...

Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from...

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...

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...

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...

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, ...

Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house ...