Winter Park Homes with Private Pool type

Winter Park Homes with Private Pool type

Welcome to Winter Park, Florida—a picturesque city that perfectly blends small-town charm with vibrant cultural experiences. Nestled just north of Orlando, Winter Park is renowned for its stunning lakes, lush parks, and historic architecture. The city is a haven for art lovers, boasting the renowned Charles Hosmer Morse Museum of American Art, which showcases an impressive collection of Tiffany glass. With its tree-lined streets and delightful boutiques, Winter Park offers a unique shopping experience, complemented by an array of gourmet dining options that cater to every palate.

For those seeking a home in this enchanting city, consider the allure of properties featuring private pools. Imagine stepping into your backyard oasis where you can unwind under the Florida sun or host summer barbecues with friends and family. Homes with private pools in Winter Park not only provide a refreshing escape but also enhance your lifestyle, offering a perfect blend of relaxation and entertainment.

Whether you're looking for a cozy bungalow or an elegant estate, Winter Park's real estate market offers a diverse selection of homes to suit your needs. Many of these properties are situated in serene neighborhoods, providing a peaceful retreat while still being in close proximity to the vibrant downtown area, where you can enjoy outdoor festivals, farmer's markets, and seasonal events.

Experience the best of Florida living in Winter Park, where stunning homes with private pools await you. Dive into a lifestyle filled with warmth, community, and endless sunshine. Your dream home is just a splash away!

Newest Winter Park Homes with Private Pool type

1667 Walnut Avenue, Winter Park
$2,275,000
4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Beautifully designed and appointed, this stunning contemporary residence offers the perfect combination of modern luxury, comfortable living, and exceptional indoor-outdoor entertaining. Ideally located in the quieter, more intimate section of Winter Park's coveted Nut streets, this home offers a wonderful neighborhood setting just minutes from the boutiques, acclaimed restaurants, and vibrant lifestyle of Park Avenue . Light-filled interiors, designer upgrades, and beautiful wood flooring create an inviting first impression. A spacious office features impressive eight-foot windows and beautiful built ins while the open-concept living area seamlessly connects the chef's kitchen, dining space, and expansive family room. The kitchen showcases light quartz countertops, premium appliances, a custom range hood, and designer lighting. The family room is anchored by a contemporary fireplace and custom shelf details. The downstairs primary suite provides a private retreat with dual vanities, a soaking tub, and an impressive 6-by-12-foot walk-through shower featuring dual showerheads and glass-tile walls. Oversized sliding glass doors extend the living space to an 18-by-15-foot covered lanai with tongue-and-groove ceilings, a fully equipped outdoor kitchen, and retractable screens. The beautifully landscaped backyard is an entertainer's dream, complete with a gas-heated pool, integrated hot tub, sun shelf, and generous green space. Upstairs, a sunlit staircase leads to a spacious loft with French doors opening to a front-facing balcony, offering flexibility for a second living area or playroom. Three additional bedrooms, two full bathrooms, and a large gym provide ample accommodations for family and guests. A large laundry room with custom built-ins completes the second floor. Enjoy walkable access to Phelps Park and the Winter Park YMCA, with Park Avenue, the Winter Park 9-hole golf course, and the popular Orlando Avenue dining and shopping districts just moments away. Zoned for highly sought-after Winter Park schools, this exceptional newer-construction home offers the opportunity to enjoy the very best of Winter Park living, combining contemporary luxury, a peaceful neighborhood setting, and an unparalleled lifestyle close to everything.

1667 Walnut Avenue, Winter Park
1008 N Pennsylvania Avenue, Winter Park
$2,500,000
4 Beds ⋅ 5 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code
Discover an exceptional opportunity to own a beautifully designed luxury home overlooking the prestigious Winter Park Nine Golf Course in one of Winter Park, Florida’s most desirable neighborhoods! Built in 2020, this stunning residence offers approximately 3,500 square feet of thoughtfully designed living space, featuring 4 bedrooms and 4.5 bathrooms. From the moment you step inside, you'll be welcomed by an abundance of natural light, an impressive open-concept floor plan, and soaring ceilings accented by elegant tray ceiling details. Every element of this home comes together to create an atmosphere of sophistication, comfort, and true luxury living. The spacious interior seamlessly blends the living, dining, and entertaining spaces, creating the perfect environment for both everyday living and hosting guests. Step outside to your own private backyard oasis, complete with an amazing pool, perfect for enjoying the beautiful Florida lifestyle. The property also features a spacious two-car garage and a highly desirable in-law suite located above the garage. Complete with its own private kitchen, this separate living space is ideal for extended family, overnight guests, multigenerational living, or a private retreat. Located in one of the most sought-after neighborhoods in Winter Park, this exceptional property offers the opportunity to enjoy golf course living while remaining close to everything that makes Winter Park so special. From its newer construction and light-filled open spaces to its impressive outdoor living area and versatile separate guest quarters, this home delivers the perfect combination of elegance, functionality, and luxury. Don't miss your opportunity to experience this remarkable Winter Park residence!

1008 N Pennsylvania Avenue, Winter Park
1351 Mayfield Avenue, Winter Park
$3,050,000
5 Beds ⋅ 5 Baths ⋅ Temple Heights SubDv. ⋅ 32789 Zip Code
Under Construction. A commanding front façade, and a coveted brick-street setting near the Vias. Interiors defined by natural stone, architectural detail, and a thoughtful balance of grandeur and intimacy. This distinctive Winter Park residence brings together the elements that make a luxury home memorable and a location that is difficult to replicate. The arrival is dramatic featuring a soaring two-story foyer that opens to a spacious living room where wood beams and substantial stonework establish a rich material palette. A stone-wrapped fireplace anchors the room, complemented by a built-in entertainment center and a wet bar with a wine refrigerator and sink. Whether hosting a large gathering or enjoying an evening by the fire, the space feels equally suited to both. Taj Mahal countertops take center stage in the kitchen, paired with custom cabinetry, a paneled refrigerator, and a Thermador appliance package. A generous adjoining dirty kitchen provides a separate sink and additional prep-space. The downstairs primary suite offers privacy and direct access to the backyard through sliding doors. In the bath, marble finishes, dual vanities, and a freestanding soaking tub create an elegant retreat. An arched shower entrance introduces a distinctive architectural detail, with dual shower heads completing the experience. An expansive closet by Idelli brings the same attention to detail to the dressing space. A second downstairs suite accommodates guests or a private office, while a laundry room supports everyday convenience. Upstairs, three additional bedrooms and a spacious bonus room create a separate setting for family, guests, and recreation. The outdoor living space is equally as impressive. A full summer kitchen sets the stage for open-air dining, with a heated pool and spa providing the centerpiece for afternoons and evenings at home. Substantial green space adds another dimension to the backyard, offering room to gather beyond the pool. The surrounding neighborhood places this residence in exceptional company, with impressive estates lining the street. Phelps Park and the YMCA are within walking distance; the Winter Park Racquet Club, Park Avenue’s boutiques and restaurants, and downtown Winter Park are close by. Interlachen Country Club further enhances the appeal of this sought-after location. With its stunning architecture, richly appointed interiors, and exceptional outdoor living, this residence makes a lasting statement on one of Winter Park’s coveted brick streets.

1351 Mayfield Avenue, Winter Park
Winter Park
$2,100,000
4 Beds ⋅ 5 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code
Experience elevated living in this exceptional two-story Winter Park residence featuring 4 bedrooms and 4.5 bathrooms, custom designed with comfort, style, and entertaining in mind. Enjoy your own private outdoor oasis with a heated wading pool and outdoor kitchen with a gas grill, sink and two refrigerated drawers, perfect for relaxing or hosting family and friends year-round. Mature podocarpus line the outdoor space for added privacy. The luxurious primary suite offers a spa-inspired steam shower, along with custom closets and beautifully appointed custom vanities. The kitchen features custom cabinetry with both electric and manual operating cabinets, built-in coffee/espresso maker and walk in pantry adding a distinctive touch of convenience and functionality. Additional highlights include a Ring camera security system and a professionally coated garage floor. A rare opportunity to enjoy access to the private waters of Lake Killarney, adding an extra element of lifestyle and recreation. This exceptional home combines stylish features, indoor comfort, and outdoor entertaining in a desirable Winter Park location.

Winter Park
2507 Lafayette Avenue, Winter Park
$1,850,000
4 Beds ⋅ 6 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
A striking modern façade introduces this exceptional new residence by SoulTech Homes, where bold architectural expression meets beautifully considered interiors. Distinguished by extensive custom millwork, sophisticated paneling, and integrated LED lighting, the home delivers a level of detail and finish rarely found at this price point. An intelligently designed floor plan balances dramatic gathering spaces creating a home equally suited to memorable entertaining and effortless everyday living. At the heart of the residence, a spectacular double-height living room makes an unforgettable impression. A soaring paneled feature wall, accented by ambient LED lighting and a custom entertainment center, brings depth, texture, and architectural presence to the space. The kitchen pairs White Paradise quartz countertops with custom cabinetry and a full suite of Thermador appliances. Designed to be as functional as it is beautiful, this culinary centerpiece is complemented by a wine bar featuring a wine refrigerator and display shelving illuminated with integrated LED lighting. A spacious walk-in pantry and mudroom area adds exceptional everyday convenience. A downstairs guest suite offers comfortable accommodations, while a dedicated office provides a refined setting for working from home. Upstairs, the primary suite becomes a private sanctuary. An expansive dressing room complements the retreat, while the luxurious bath invites relaxation with a freestanding soaking tub, dual vanities, and a generous walk-in shower. Two additional upstairs bedrooms each enjoy it's own bathroom, and a conveniently positioned laundry room completes the upper level. The backyard is designed for entertaining. Approx. 900 SF of outdoor living space flows straight from the main living area, anchored by a 201 SF covered patio for shaded dining and gatherings in any weather. Around it, a 702 SF pool deck frames a heated 12' x 24' pool, with plenty of room for loungers, a dining table, and guests spilling out from the house. A full summer kitchen turns the backyard into a true outdoor room, so hosting a dinner party or a weekend pool day feels like a natural extension of the home. A metal roof, and enhanced landscaping complete the property’s polished presentation. The location adds another compelling dimension. Set within an evolving neighborhood experiencing an exciting wave of new construction, the home places you close to Park Avenue’s celebrated shops and restaurants, within walking distance of the Winter Park Racquet Club, and near the Maitland Art Center and Phelps Park. From its commanding first impression to its thoughtfully appointed private spaces, this residence offers a distinctive expression of modern luxury, bringing together architectural drama, exceptional craftsmanship, and the ease of Winter Park living.

2507 Lafayette Avenue, Winter Park
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
647 Randy Lane, Winter Park
$1,699,999
4 Beds ⋅ 4 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code
WINTER PARK LUXURY LIVING! Welcome to 647 Randy Lane, where timeless elegance meets modern sophistication in one of Winter Park's most desirable locations! Offered for the first time in over a decade, this beautifully maintained residence is situated on an expansive 0.36-acre corner lot, surrounded by lush, mature landscaping and designed for exceptional Florida living. Step inside to discover a spacious, open-concept, floor plan that effortlessly blends comfort, style, and functionality. At the heart of the home is a stunning chef's kitchen featuring gorgeous quartz countertops, premium Wolf double ovens, and a built-in Sub-Zero refrigerator—perfect for everyday living and entertaining alike. Your private backyard oasis awaits! Enjoy an oversized swimming pool, expansive patio, and generous green space, all surrounded by tropical landscaping that creates a peaceful, resort-style atmosphere. Thoughtful outdoor lighting sets the stage for evening entertaining, while the seamless indoor-outdoor flow makes this home ideal for enjoying Florida's beautiful weather year-round. Impressive upgrades and features include a NEW ROOF (2024), SOLAR PANELS (2022), resurfaced pool and updated pool tile (2021), tankless gas water heater, well irrigation system, and an oversized indoor laundry room. LOCATION, LOCATION, LOCATION! Just minutes from Winter Park's iconic Park Avenue, you'll enjoy convenient access to exceptional dining, boutique shopping, beautiful parks, and cultural attractions. The property is also zoned for sought-after schools, including Audubon K-8 and Winter Park High School. Buyers should verify current school assignments. Luxury, privacy, and an unbeatable Winter Park lifestyle—all in one exceptional property! Don't miss this rare opportunity to make 647 Randy Lane your next home.

647 Randy Lane, 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
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