Winter Park Pool Homes for Sale

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area...

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...

Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue...

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...

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...

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom b...

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,...

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

In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered ...

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...

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...

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...

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...

Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansi...

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

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

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...

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...

Under Construction. Welcome to 2228 Howard, a designer home that complements the irreplaceable natural beauty surrounding it with a one-of-a-kind façade. This curved stre...

Under Construction. A refined expression of new construction by LUIH Homes, this exceptional two-story residence blends timeless architecture with thoughtfully curated mo...

This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community...

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...

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...

Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, L...

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

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

Pre-Construction. To be built. Discover refined modern living in The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 custom residen...

Winter Park Luxury Awaits You! Welcome to your dream home—a stunning custom-built luxury residence offering the perfect blend of elegance, comfort, and modern design. Fe...

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...

Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes cas...

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. 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 PRIVATE RESORT-STYLE SANCTUARY 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...

Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoug...

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...

Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom resid...

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

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...

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

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...

This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function...

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...

On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throu...

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

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...

Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private...

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, ...

Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned architect Gary Hancock is a masterclass in crafts...

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...

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 ...

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...

NEW PRICE — NOW $1,399,500 — THE BEST DEAL IN WINTER PARK! Discover sophisticated modern living at 607 Ellen Drive — a brand-new construction masterpiece by the acclaime...

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...

Now offered out an exceptional new price, the seller has thoughtfully repositioned this home to encourage serious buyer interest – seller is actively moving. This remarka...

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,...

Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Or...

Located within an intimate gated community of just 28 homes and only a short drive to Downtown Winter Park, this exceptional former model home by K. Hovnanian Homes showc...

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...

Seller is offering a generous $25,000 credit toward price or closing costs, giving the next owner an incredible opportunity to personalize this Winter Park residence to t...

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...

Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides im...

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

Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-...

Completely reimagined and professionally renovated, this stunning Winter Park POOL home offers approximately 1,950 square feet of thoughtfully designed living space with ...

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...

Virtually Staged. This move-in-ready classic ranch-style pool home offers a relaxed 60’s retro vibe with vaulted ceilings, 4 bedrooms, 2 full bathrooms, and light-filled ...

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...

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...

Nested on a spacious, tree lined lot just steps from Lake Killarney, 2361 Roxbury Road offers a rare opportunity to create your dream home in one of Winter Park’s most co...

Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beau...

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...

Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity. The bac...

PRICE REDUCED!!! ROOF 4 yrs. old, newer A/C, In-ground Pool. Enclosed Patio — a beautifully maintained turnkey home nestled in the heart of Winter Park, one of Central F...

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 ...

Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House...

Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, of...

Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and di...

Virtually Staged. Welcome to 2223 Conifer Ave, recently enhanced with a new roof, fresh interior paint, and fresh exterior paint. The kitchen features all stainless steel...

Virtually Staged. Discover this spacious 3-bedroom, 2-bathroom home offers 1,483 sq ft of comfortable living space with a functional layout and plenty of room for everyda...

PRICE IMPROVEMENT! This 4-bedroom, 2-bath pool home in the heart of Winter Park is priced to sell and offers an incredible opportunity to make it your own. While the prop...

One or more photo(s) has been virtually staged. Pool Home *No HOA *Paid-Off Solar Panels **Roof (2018) Welcome to this well-maintained 3-bedroom, 2-bathroom home offering...

Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa pe...

Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully...