Winter Park Homes with Private Pool type

Winter Park Homes with Private Pool type

Located in the beautiful state of Florida, Winter Park is a charming city that offers a perfect blend of natural beauty, cultural attractions, and a warm community atmosphere. Nestled in Orange County, Winter Park is known for its tree-lined streets, stunning lakes, and historic charm.

One of the most sought-after features in real estate in Winter Park is homes with a private pool. With the year-round warm weather that Florida is famous for, having a private pool is not only a luxury but also a necessity for many residents. Whether you want to take a refreshing dip on a hot summer day or simply relax by the poolside, homes with private pools provide the ultimate oasis for relaxation and entertainment.

Winter Park offers a wide variety of homes with private pools to suit different tastes and budgets. From cozy bungalows to spacious estates, you can find a range of options to meet your specific requirements. Imagine waking up in the morning and enjoying a refreshing swim before starting your day or hosting poolside parties with friends and family on weekends - owning a home with a private pool in Winter Park allows you to create lasting memories and live a resort-style lifestyle.

In addition to the private pool amenities, Winter Park boasts a vibrant downtown area with boutique shops, art galleries, and a thriving dining scene. The city is also home to the renowned Rollins College, which adds to the cultural and intellectual atmosphere of the community.

If you are looking for a city that combines natural beauty, cultural attractions, and the luxury of homes with private pools, Winter Park, Florida is the perfect place to call home.

Newest Winter Park Homes with Private Pool type

640 N Park Avenue Unit 26, Winter Park
$629,500
2 Beds ⋅ 2 Baths ⋅ Park Aire Condo SubDv. ⋅ 32790 Zip Code
renovated 2 years ago new AC and air vents, downtown Winter Park living at its best, iconic Park Aire condominiums, auto window shades built in, new kitchen - association approval - laundry is on 3rd floor or basement

640 N Park Avenue Unit 26, Winter Park
1400 Pelican Bay Trail, Winter Park
$968,000
5 Beds ⋅ 4 Baths ⋅ Pelican Bay SubDv. ⋅ 32792 Zip Code
Awesome 5 bedroom 3.5 bathroom custom built home on gorgeous 1.2 acre WATERFRONT cul-de-sac lot in lovely Pelican Bay of Winter Park. A True Gem on the Lake on a private dead-end street! Step through the front door and into a welcoming foyer with beautiful wood floors and oversized living and family rooms featuring dual wood-burning fireplaces. 4 BRAND NEW CUSTOM BAY WINDOWS (NOV 2026) installed in living room. The gourmet kitchen features classic oak cabinetry and upgraded granite counters, as well as BRAND NEW STAINLESS STEEL SIDE BY SIDE REFRIGERATOR (NOV 2026). Kitchen bay windows overlook massive screened rear porch, screened pool oasis, and breathtaking backyard waterfront views of Lake Florence. Main bedroom is downstairs and features large ensuite bathroom with dual sinks, garden tub, and walk in shower. Additional 4 bedrooms and 2 full bathrooms as well as bonus room are located upstairs and enjoy wonderful lakefront views. BRAND NEW ROOF INSTALLED NOV 2021. This oversized lot contains a variety of wonderful fruit trees and edible plants located around the property including avocado, purple yam, lychee, chinese chives, jujube, apple cactus, persimmon, mango, and dragon eye. The lake frontage speaks for itself, but as you can imagine the sunsets are truly superb. The Winter Park location is one of the best, close to shopping, schools, major roads, international airport, and amazing restaurants. Bring your buyers so they can make this beautiful custom home their own.

1400 Pelican Bay Trail, Winter Park
1507 Golfside Drive, Winter Park
$849,000
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Virtually Staged. Perfectly positioned on the 13th tee box and 16th fairway of the Winter Park Pines Golf Course, this home sits on an corner lot and offers a rare opportunity to create your dream home while enjoying breathtaking golf course views.  **The current floor plan features three bedrooms, as the original fourth bedroom has been converted into an expansive walk-in closet for the primary suite, Featuring over 2,000 square feet of single-story living space, this home has been extensively renovated throughout the interior, offering the charm of an established Winter Park neighborhood with the comfort and appeal of modern finishes. Step inside to discover new luxury vinyl flooring, beamed ceilings, modern fireplace. Brand new kitchen appliances with modern grey cabinetry, crown molding and white quartz counter tops.  Step outside to your own private backyard retreat, complete with a 30x11 covered patio and screen-enclosed swimming pool overlooking the lush fairways of WP18. Whether enjoying your morning coffee, entertaining guests, or simply relaxing poolside, this outdoor living space offers a peaceful setting that’s increasingly difficult to find in Winter Park. Additional highlights include a NEW ROOF (NOVEMBER 2024), New pool pump, resurfaced pool with new pavers surrounding,  a large indoor laundry room and no HOA. Located just a few doors from the Cady Way Trail on one of the neighborhood's most picturesque oak-canopied streets, the setting is truly exceptional. This is a rare opportunity to purchase a home set directly on one of Winter Park's premier golf courses, where major mechanical system upgrades and costly infrastructure improvements have already been completed, creating the perfect opportunity to transform the interior into your own custom vision. This is move in ready so schedule your showings today!

1507 Golfside Drive, Winter Park
1735 Meadowgold Lane, Winter Park
$480,000
3 Beds ⋅ 2 Baths ⋅ Autumn Glen Ph 1 SubDv. ⋅ 32792 Zip Code
Virtually Staged. More photos coming soon! YOUR FLORIDA DREAM LIFESTYLE STARTS HERE! Welcome to 1735 Meadowgold Lane in the desirable Autumn Glen community! This beautifully updated pool home combines modern style, comfortable living, and the outdoor lifestyle Florida is famous for. Step inside and discover soaring ceilings, skylights, beautiful flooring, and a stunning white marble wood-burning fireplace. The renovated kitchen is a showstopper, featuring crisp white and frosted-glass cabinetry, Blue Moon granite countertops, a contemporary glass backsplash, and stainless steel appliances. Need extra space? The spacious, climate-controlled bonus room offers endless possibilities for a home office, gym, media room, or additional living area. Enjoy beautifully updated bathrooms, including a primary suite with a double vanity and elegant marble-accented, glass-enclosed shower as well as a spacious walk in closet in the primary suite and an oversized walk in closet in the bonus room. Your private backyard oasis awaits! Relax in the screened-in pool, entertain on the spacious covered patio, or enjoy the privacy of your fully fenced backyard. BIG UPDATES. BEAUTIFUL LIVING. PEACE OF MIND. Major improvements include: - 2019 Roof and skylight - 2019 Pool resurfaced - 2022 New Windows - 2023 Whole-house repiping, Updated flooring, New HVAC - 2026 New pool pump This is Move-in ready home, located in the established Autumn Glen Community, featuring sidewalks, tennis/pickleball courts and a neighborhood playground. Plus, you're zoned for top rated Seminole County schools.

1735 Meadowgold Lane, Winter Park
1663 N Park Avenue, Winter Park
$2,750,000
4 Beds ⋅ 5 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
An exceptional expression of contemporary luxury on Winter Park’s historic Park Avenue! This newly constructed residence presents a luxurious design and elevated craftsmanship. From the sleek metal roof to the dramatic 11-foot custom statement entrance door, this 4 bedroom, 5 bath home makes an unforgettable first impression. At the heart of the home, the expansive designer kitchen makes a striking statement with sleek GOLA-profile cabinetry, an expansive 9 foot center island, and exquisite quartzite countertops and backsplash. Premium Wolf and Thermador appliances deliver exceptional culinary performance. Discreetly concealed behind a door adjacent to the main kitchen, a fully equipped secondary prep kitchen features a six burner gas range with double ovens, offering an exceptional level of functionality for everyday living and entertaining. The living area is equally impressive, featuring a pre-wired entertainment wall ready for a personalized audio-visual experience. The first-floor primary suite serves as a private sanctuary, highlighted by a luminous LED aura ceiling. The spa-inspired primary bathroom features floating contemporary cabinetry with integrated sensor lighting, Kohler Purist collection faucets and fixtures, and anti-fog LED mirrors. A luxurious freestanding soaking tub creates an elegant focal point, while the spacious, glass enclosed, walk-in shower showcases beautiful tilework and separate shower systems on both sides. Sensor-activated lighting throughout the bathrooms and closets add another layer of modern sophistication. The custom-designed primary closet rivals a luxury boutique, featuring a full-length mirrored door, valet rod, convertible vanity, central island with integrated electrical outlets, and built-in shoe bench. The second level features a dedicated bonus room offering the flexibility to create a private home theater, office, or a creative studio. A separate den area provides another versatile living retreat along with three generously appointed bedrooms, each with its own en-suite bathroom and custom walk-in closet. Additional appointments include modern switches and outlets, smart thermostats, Minka-Aire ceiling fans, CAT 6 cabling in every room, and smart-home pre-wiring. The garage is well-appointed, featuring wall-mounted garage door openers with battery backup, a Tesla charging station compatible with other electric vehicles, and a separate 50-amp outlet to accommodate additional EV charging equipment. The outdoor living experience is a defining feature of this extraordinary property. Designed by Complete Outdoors, a stunning, salt water swimming pool featuring two dramatic 24-inch water bowls, a custom pebble interior, natural stone coping, and integrated heating and cooling capabilities, is being installed. A complete summer kitchen creates an inviting setting for alfresco dining,. This creation offers a distinctive lifestyle opportunity in the heart of Winter Park. Enjoy a walkable lifestyle surrounded by upscale boutiques, restaurants, charming sidewalk cafés, and the lush beauty of Central Park. Experience the beautiful Winter chain of lakes and the Winter Park Golf course, a 9 hole gem in the heart of Winter Park. Explore the Saturday Farmers Market, discover local art museums, and experience the vibrant community events and timeless traditions that make downtown Winter Park such an exceptional place to call home.

1663 N Park Avenue, Winter Park
1398 Grove Terrace, Winter Park
$1,949,000
4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Improved! Positioned on a charming brick-lined street in historic Winter Park adjacent to Windsong, this custom-built residence pairs solid architectural craftsmanship with extensive modern upgrades. Refinished Mahoghany double doors open to 12-foot ceilings, soft curved archways and a thoughtful layout finished with travertine on the main level and reclaimed maple and beech hardwoods upstairs and in the primary suite. The expansive, open family room centers around a gorgeous gas fireplace and flows seamlessly into a true chef’s kitchen featuring a new marble tile backsplash, Rejuvenation drum chandelier, granite countertops, prep island, custom lighted cabinetry, a six-burner gas range with pot filler, double ovens with warming drawer and a Thermador French-door refrigerator. An adjoining butler’s pantry with wine fridge and wet bar connects directly to the formal dining room, complemented by a newly constructed dedicated wine room and a quiet main-level office or library. The first-floor primary suite offers a private retreat with detailed tray ceilings, dual walk-in closets, a jetted soaking tub, twin vanities and direct French-door access to the outdoor living area. Upstairs, three spacious bedrooms and two full baths including a private en-suite accompany a classic Juliet balcony overlooking the pretty front yard. Designed for effortless Florida living, the covered summer kitchen is perfect for relaxing with friends and watching football, featuring a built-in grill, custom copper hood and beverage fridge, while the second covered lanai is perfectly situated for a hot tub. Both look out over a private saltwater pool framed by maintence-free turf, lighting and a newly planted podocarpus privacy hedge. Recent capital improvements include new dual HVAC units, a tankless water heater, whole-home surge protection, central vacuum, smart-home automation for pool, security and irrigation, six new exterior fixtures, complete interior and exterior repainting, epoxy-coated garage floors, extensive kitchen renovations, refinished front entry doors and fully refreshed landscaping. Enjoy no HOA dues, seasonal neighborhood block gatherings and quick access to Lake Mizell, premier schools (Brookshire, WPHS, Park Maitland, Lake Highland, Geneva) and a convenient pedestrian cut-through directly to Park Avenue dining and shopping.

1398 Grove Terrace, Winter Park
1350 Lyndale Boulevard, Winter Park
$1,499,000
4 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
Photos coming soon. Experience timeless elegance and exceptional living in the heart of Winter Park! Nestled along a charming, quiet brick-lined street just moments from iconic Park Avenue, this beautifully designed custom residence offers the perfect combination of sophistication, comfort, and Florida indoor-outdoor living. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and 3,478 square feet of living space, this impressive home welcomes you with soaring 10-foot ceilings, rich Brazilian cherry hardwood floors, elegant architectural details, and an abundance of natural light. At the heart of the home, the gourmet kitchen is designed for both everyday living and effortless entertaining, featuring a spacious center island, natural wood cabinetry, premium cooking appliances, built-in refrigerator, and wine refrigerator. The kitchen flows seamlessly into the inviting family room, complete with a beautiful gas fireplace. The luxurious first-floor primary suite offers a peaceful retreat with generous walk-in closets, a spa-inspired bathroom, and French doors opening to the private screened pool and patio. Upstairs, additional bedrooms and a spacious bonus room provide flexibility for a home office, fitness studio, media room, or guest accommodations. Step outside to your own private oasis, where a sparkling pool, relaxing spa, mature landscaping, and inviting outdoor living spaces create an ideal setting for entertaining or unwinding year-round. Additional highlights include formal living and dining spaces, an attached two-car garage, abundant storage, and a desirable location with no HOA. Enjoy the best of the Winter Park lifestyle, with convenient access to Park Avenue's celebrated restaurants, boutique shopping, cafés, cultural attractions, parks, and nearby lakes. An exceptional opportunity to own a distinctive residence in one of Central Florida's most desirable communities. Schedule your private showing and discover everything this Winter Park home has!

1350 Lyndale Boulevard, Winter Park
1441 Grove Terrace, Winter Park
$5,950,000
5 Beds ⋅ 6 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park lot with 130 feet of water frontage, the home pairs timeless architecture, richly detailed interiors, and expansive outdoor living. Led by a husband-and-wife team originally from Europe, Vimaro Homes brings together her expertise in interior design and his in construction. Their hands-on approach brings a personal commitment to every selection and detail, prioritizing lasting quality, thoughtful design, and craftsmanship over the cost-driven formulas common in investment-built spec homes. A striking façade and tile roof establish an elegant arrival, complemented by a dual-entry driveway featuring a diamond-patterned composition of turf and concrete. An underground three-car garage preserves the architectural approach, while an elevator connects all three levels. Inside, a marble mosaic entry introduces intricate trim work and classic reeded crown molding, establishing the home’s enduring character. The spacious living room features a marble-wrapped fireplace, custom built-ins with LED up-lighting, and expansive sliding doors framing views of the pool and lake. The kitchen pairs marble countertops and custom inset cabinetry with Perrin & Rowe fixtures and Thermador appliances, including a paneled refrigerator. A substantial scullery with a prep kitchen and pantry supports entertaining, while the nearby dining room overlooks the water. The downstairs primary suite offers a private retreat with its own fireplace and an expansive, custom-fitted walk-in closet with a center island. The primary bath features Casablanca marble tile, dual vanities, Perrin & Rowe fixtures, and a spacious walk-in shower. Upstairs, four additional bedrooms each offer an ensuite bath and walk-in closet, alongside a bonus room, laundry room, and terrace. Throughout the home, natural stone, finely crafted cabinetry, and classic architectural details reflect the team’s European influences. Outdoors, a generous lanai with retractable screens and a full summer kitchen extends the living spaces toward Lake Sylvan. A three-tiered deck brings together a pool, spa, and sweeping water views, while expansive green space and a dock complete the waterfront setting. Set on a brick street moments from Park Avenue’s restaurants, boutiques, and cafés, this residence combines Winter Park’s distinctive character with an exceptional lakefront setting. Shaped by the personal vision and craftsmanship of Vimaro Homes, it offers a refined expression of waterfront living.

1441 Grove Terrace, Winter Park
1534 Miller Avenue, Winter Park
$1,379,900
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Under Construction. NEW CONSTRUCTION! New photos coming soon! Photos of a similar model. Welcome to Winter Park Grove — Winter Park’s newest community by one of the area's finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, an oversized island, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool & lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual sink vanity, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. Upstairs, a large bonus room with a closet offers versatility as a second living, game room and it can even be enclosed to create an additional bedroom. Two spacious bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. Photos are of a similar model, finishes may vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1534 Miller Avenue, Winter Park
1441 Palm Avenue, Winter Park
$2,449,000
5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Under Construction. In the heart of Winter Park’s coveted Tree Streets, this stunning residence brings together impeccable finishes, a striking architectural presence, and a location that puts so much of daily life within easy reach. Opportunities to find new construction in this established neighborhood are becoming harder to come by, making this home an especially exciting offering. The front façade makes a memorable first impression, with beautiful curb appeal that carries naturally into the interiors. In the spacious living room, a stone-wrapped fireplace anchors the space, complemented by a built-in entertainment center and display shelving with soft LED underlighting. The kitchen is a standout. Calacatta quartz countertops and an intricate mosaic backsplash set an elegant tone, while a full suite of Thermador appliances, including a paneled refrigerator, brings substance to the beautiful design. A spacious pantry keeps everything tucked away, and a wine bar with a dedicated wine refrigerator makes hosting feel effortless. The primary suite offers a lovely sense of retreat. This spacious bedroom is complemented by a beautifully finished bath with marble mosaic tile, a freestanding tub, and a generous walk-in shower with a rain showerhead. An oversized closet adds the kind of everyday luxury that is just as valuable as the finishes themselves. A rare first-floor guest bedroom gives visitors a comfortable place of their own or offers a space for a dedicated office. Upstairs, three additional bedrooms, each with a walk-in closet, surround a loft that offers room for a second living area, movie nights, or a quiet place to unwind. The outdoor living is equally impressive, with a spacious covered lanai and full summer kitchen overlooking the pool and spa, a beautiful setting for dinners or a quiet afternoon at home. Surrounding green space gives the backyard a sense of openness and room to enjoy the Florida sunshine. With Phelps Park and the YMCA moments away, and Park Avenue’s restaurants and boutiques just a golf cart ride from home, the location is every bit as appealing as the residence itself. Beautifully finished and thoughtfully arranged, this is a chance to enjoy the ease of a brand-new home in a neighborhood whose charm has long been established.

1441 Palm Avenue, Winter Park
1825 Chilean Lane, Winter Park
$450,000
5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home offers 1,636 square feet of stylish, thoughtfully designed living space with modern finishes throughout. Light gray wood-look plank tile flooring and recessed lighting create a bright, cohesive feel. The contemporary kitchen showcases gray shaker-style cabinetry, sleek black granite countertops, a marble-look tile backsplash with black mosaic accents, stainless steel appliances, and a breakfast bar with seating for four. The first primary suite is privately positioned away from the additional bedrooms and features an ensuite bathroom with a marble-look tiled shower, decorative mosaic accents, multiple shower heads including a rain shower, a frameless glass enclosure, and a gray vanity topped with black granite. The second primary suite provides added flexibility for multigenerational living, extended guests, or a private retreat. Step outside to enjoy your own backyard oasis, complete with an in-ground pool, screened lanai, and fully fenced, spacious backyard with plenty of green space for relaxing, entertaining, and outdoor activities. Ideally located approximately 10 minutes from the restaurants and boutiques of Park Avenue, with convenient access to UCF, Full Sail University, Rollins College, major transportation routes, shopping, and dining. Orlando International Airport is approximately 25 minutes away. With its modern renovations, dual primary suites, and inviting outdoor living space, this home offers a unique combination of comfort, flexibility, and convenience! ROOF - 2024 HVAC - 2025 PLUMBING - 2026 ELECTRICAL - 2024

1825 Chilean Lane, Winter Park
1021 Princess Gate Boulevard, Winter Park
$410,000
3 Beds ⋅ 2 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to this 3-bedroom, 2-bath pool home in the established Howell Estates neighborhood of Winter Park! Situated on a spacious 0.31-acre lot, this single-story residence offers 1,318 square feet of living space with a split-bedroom layout and a combination of tile and luxury vinyl flooring. The living room features built-in cabinetry with a granite countertop, while the kitchen offers stone countertops, a tile backsplash, and a closet pantry. The primary suite includes dual closets and a private bathroom with a walk-in shower. Sliding glass doors from the dining area open to a covered lanai and screened-in pool, creating an inviting setting for outdoor relaxation and entertaining. The spacious, fenced backyard offers additional room to enjoy the outdoors. Other highlights include a brand-new water heater, a 2018 roof, a 2024 HVAC system, and no HOA fees. Conveniently located near Howell Branch Road and Semoran Boulevard, the property provides access to shopping, dining, parks, and everyday essentials throughout the Winter Park area. With its private pool, generous lot size, and convenient location, this home offers a wonderful opportunity to enjoy Florida living. Schedule your private showing today!

1021 Princess Gate Boulevard, Winter Park
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