Winter Garden Homes with Private Pool type

Winter Garden Homes with Private Pool type

Welcome to Winter Garden, Florida, a picturesque gem nestled in the heart of Orange County. Known for its charming historic downtown, vibrant community spirit, and lush landscapes, Winter Garden offers a delightful blend of small-town charm and modern conveniences. With its proximity to Orlando, residents enjoy easy access to world-class attractions, shopping, and dining, all while relishing the serene ambiance of suburban life.

One of the standout features of homes in Winter Garden is the abundance of properties boasting private pools. Imagine stepping into your own backyard oasis, where you can unwind after a long day or entertain friends and family on warm Florida evenings. These homes with private pools not only enhance your lifestyle but also provide a perfect retreat for those sunny days that Florida is famous for. Whether you’re looking for a sprawling estate or a cozy family home, Winter Garden’s real estate market offers a variety of options to suit your needs.

Beyond the allure of private pools, Winter Garden is renowned for its outdoor recreational opportunities. With an extensive network of parks, trails, and lakes, there are endless possibilities for outdoor adventures. The West Orange Trail, a favorite among cyclists and joggers, winds through the area, offering scenic views and a chance to connect with nature.

In Winter Garden, you’re not just buying a home; you’re investing in a lifestyle. With its friendly community, beautiful surroundings, and the luxury of a private pool, this city is the perfect place to call home. Explore the real estate offerings today and discover your dream oasis in Winter Garden!

Newest Winter Garden Homes with Private Pool type

1370 Portmoor Way, Winter Garden
$755,000
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
Nestled within the highly desirable golf course community of Stoneybrook West in Winter Garden, this beautifully renovated 5-bedroom, 4-bathroom residence offers a perfect blend of modern finishes, spacious living areas, and exceptional Florida living. Thoughtfully updated throughout, the home features a newer roof and HVAC system, fresh interior paint, new custom kitchen and bathroom cabinetry, luxury vinyl plank flooring, new bedroom carpeting, updated lighting and ceiling fans, and a newly re-screened enclosure. At the heart of the home, the stunning remodeled kitchen showcases custom cabinetry, all new stainless steel appliances, elegant quartz countertops, designer lighting, and an oversized breakfast bar ideal for gathering and entertaining. A charming breakfast nook provides the perfect spot for casual dining while enjoying picturesque views of the golf course. The inviting living spaces are enhanced by a beautiful double-sided fireplace, creating warmth and character throughout the home. A versatile downstairs flex room and bathroom offer endless possibilities for a home office, in-law suite, or playroom. Upstairs, a loft at the top of the stairs provides additional living space for relaxing, working, or entertaining. The private primary suite serves as a peaceful retreat, featuring a generous layout, a luxurious ensuite bathroom with an oversized walk-in shower, and a private balcony overlooking the golf course—an ideal place to enjoy your morning coffee or unwind at the end of the day. Four additional bedrooms provide flexibility for family, guests, or additional workspace. The thoughtfully designed outdoor living area includes a screened pool with spa, new pool equipment and a convenient fourth bathroom with a shower accessible from the pool area, making entertaining and enjoying Florida's year-round sunshine effortless. Beyond the home, Stoneybrook West offers an exceptional lifestyle with resort-style community amenities. The HOA includes access to the Olympic-sized community pool, splash pad, clubhouse with fitness center, basketball courts, tennis courts, and pickleball courts. Residents can also enjoy the community boat ramp, and fishing pier, providing even more opportunities for outdoor recreation and relaxation. Newer Roof and HVAC. Ideally located near excellent schools, shopping, restaurants, and everyday conveniences, Stoneybrook West is guard gated and offers easy access to the 429, Florida Turnpike, and 408, as well as historic downtown Winter Garden and Central Florida's world-famous theme parks. With its extensive renovations, golf course views, private pool, and outstanding community amenities, this exceptional home offers the perfect combination of comfort, style, and location. Schedule your showing today!

1370 Portmoor Way, Winter Garden
15823 Shorebird Lane, Winter Garden
$929,900
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Discover an exceptional opportunity to enjoy the Florida lifestyle in this beautiful Toll Brothers home in the sought-after Lakeshore Preserve community of Winter Garden. Offering 4 bedrooms, 4 full bathrooms, and 2,768 square feet, this thoughtfully designed residence combines elegant interior spaces with an outdoor living experience designed for entertaining. The heart of the home is its impressive kitchen, featuring an oversized 12-foot island, gas cooktop, convection oven, and stylish finishes. Multiple living spaces and abundant natural light create an inviting atmosphere throughout. The flexible floor plan includes a first-floor bedroom and full bathroom, additional upstairs bedrooms, a private junior suite, and a spacious primary retreat featuring tray ceilings, dual walk-in closets, two vanities, a soaking tub, and a separate walk-in shower. But the real highlight is outside. Enjoy your own private saltwater pool, beautifully appointed paver deck, and summer kitchen with natural gas. Whether hosting friends, enjoying a quiet afternoon by the pool, or making the most of Florida's beautiful weather, this outdoor space makes every day feel like a getaway. Lakeshore Preserve adds even more to the experience with its lakefront clubhouse, resort-style community pool, fitness center, barbecue area, and recreational amenities. Located in Winter Garden, this home offers an appealing combination of space, thoughtful design, outdoor entertaining, and community amenities. Come experience the home and the lifestyle for yourself.

15823 Shorebird Lane, Winter Garden
14423 Hampshire Bay Circle, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ Bay Isle 48 17 SubDv. ⋅ 34787 Zip Code
Luxury Living in Winter Garden – 14423 Hampshire Bay Circle 4 Bedrooms | 3.5 Bathrooms | Approximately 3,000 Sq. Ft. | Heated Saltwater Pool & Spa Welcome to 14423 Hampshire Bay Circle, where modern elegance meets luxury Florida living in the highly desirable Winter Garden area. This beautifully appointed residence offers approximately 3,000 square feet of sophisticated living space, featuring 4 spacious bedrooms, 3.5 bathrooms, and an impressive collection of high-end finishes throughout. At the heart of the home is a gourmet chef’s kitchen, thoughtfully designed with premium appliances, including a Sub-Zero refrigerator, professional-style gas range, and upscale finishes that create the perfect setting for both everyday living and entertaining. Step outside into your very own private resort-style oasis, featuring a heated saltwater swimming pool and relaxing spa, ideal for enjoying Florida’s beautiful weather year-round. Whether hosting unforgettable gatherings or unwinding after a long day, this outdoor retreat delivers the ultimate luxury lifestyle. Inside, the home offers an inviting combination of contemporary design, generous living areas, and refined details. The spacious primary suite provides a comfortable private retreat, while the additional bedrooms offer flexibility for family, guests, or a home office. Additional highlights include premium appliances, a high-end washer and dryer, and thoughtfully designed spaces that balance functionality with elegance. Conveniently located in Winter Garden, Florida, this exceptional property offers access to shopping, dining, entertainment, and major roadways while providing the comfort of an upscale residential setting. More than just a home, this is an opportunity to experience luxury, comfort, and resort-style living every day. Schedule your private showing and discover everything this remarkable property has to offer.

14423 Hampshire Bay Circle, Winter Garden
17224 Old Country Lane, Winter Garden
$1,699,000
6 Beds ⋅ 4 Baths ⋅ Lake Avalon Groves Rep SubDv. ⋅ 34787 Zip Code
Some homes are impressive. Others have a way of making you imagine an entirely different life. Behind private electric gates, 2.38 acres of mature trees and open grounds set the stage for a home that has been completely transformed. The owners originally envisioned it as their forever home, and the work reflects that ambition. This wasn’t a matter of replacing finishes or updating a few rooms. The kitchen was relocated, living spaces were expanded, oversized windows were introduced, and the entire home was reconsidered from the ground up. What emerged is a beautifully reimagined residence that feels almost entirely new, with a warmth and character that make it equally inviting. Inside, 3,629 square feet of living space includes six bedrooms and three and a half bathrooms, all on one level. Wood beams, custom cabinetry, ZLINE appliances, a spacious pantry, and carefully selected finishes bring sophistication without sacrificing comfort. A newly created ensuite bedroom adds flexibility, while extensive improvements, including a 2025 roof, updated electrical, new flooring, and windows, speak to the depth of the transformation. The same attention carries outdoors, where a striking covered A-frame porch overlooks a newly built screened pool and spa. Beyond the enclosure, mature trees and expansive grounds offer exceptional privacy, while a separate 1,200-square-foot boat garage with two bay entries provides generous space for watercraft, recreational vehicles, and storage. Together, these outdoor spaces offer a level of versatility rarely found so close to everyday conveniences. And that’s perhaps the most remarkable part. All of this sits just minutes from Hamlin and Horizon West, with easy access to Historic Downtown Winter Garden, the West Orange Trail, and SR 429. No HOA, no need to trade convenience for acreage, and no major transformation left for the next owner to undertake. The owners’ plans ultimately changed. The home they set out to create is complete. And the opportunity to make it your own is now here.

17224 Old Country Lane, Winter Garden
7723 Green Mountain Way, Winter Garden
$2,695,000
6 Beds ⋅ 7 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
Set along the shores of Lake Hancock with approximately 80 feet of lake frontage, this exceptional Winter Garden residence offers private boating amenities and expansive indoor-outdoor living. A two-story dock with a boat lift and two Jet Ski lifts, a screened pool and spa, and sweeping lake views define this waterfront setting. Offering 6 bedrooms, 6.5 bathrooms, over 5,100 square feet, a 3-car garage, and two primary suites on separate floors, the flexible layout is ideal for multigenerational living. A paver driveway, tile roof, stone accents, and mature landscaping welcome you home. Inside, engineered hardwood floors lead past a formal dining room on the right, connected to the kitchen through a butler's pantry, and a dedicated office on the left. The impressive two-story living room features decorative wood beams, a cascading chandelier, and a floor-to-ceiling stacked-stone accent wall. Expansive sliding glass doors open to the covered lanai, seamlessly connecting indoor and outdoor living while framing views of the pool and Lake Hancock. An open staircase with wood treads and wrought-iron balusters overlooks the living area. Just off the living room, the first-floor primary suite offers direct lanai access, a walk-in closet, separate vanities, and an oversized tiled shower. The spacious kitchen features a center island, an expansive wraparound peninsula with a farmhouse-style sink, granite countertops, cream-colored cabinetry, stainless steel appliances, a natural gas cooktop with pot filler and vent hood, a built-in microwave and wall oven, decorative tile backsplash, and built-in wine storage. A separate casual dining area overlooks Lake Hancock. Beyond it are a second downstairs bedroom and adjacent full bathroom with pool access. Near the 3-car garage, the laundry room provides a utility sink, cabinetry, and counter space. A half bath completes the first floor. Upstairs, the second primary suite features a tray ceiling, French doors to a private lakeview balcony, two walk-in closets, and an ensuite bath with dual vanities, soaking tub, and glass-enclosed shower. Three additional bedrooms and three full bathrooms, including two ensuite bedrooms, offer flexible accommodations. An expansive bonus room with hardwood flooring, lake-facing windows, and French doors to a separate balcony makes an ideal second living area, game room, or media room. Outdoor living takes center stage on the spacious covered lanai, with separate dining and lounge areas, ceiling fans, and a summer kitchen featuring a stainless steel grill, vent hood, refrigerator, and countertop space. The screened pool and spa, surrounded by an expansive paver deck, overlook Lake Hancock. Beyond the shoreline, the private two-story dock features a shaded lower seating area, boat lift, two Jet Ski lifts, and an open-air upper observation deck with panoramic lake views. From the living room and upstairs balconies to the pool and dock, the water is part of everyday life here. Summerlake community amenities include a pool, fitness center, tennis courts, playgrounds, and walking paths. Convenient to Hamlin Town Center, major highways, and Central Florida's world-famous attractions, this home offers an exceptional Lake Hancock waterfront lifestyle.

7723 Green Mountain Way, Winter Garden
665 Canopy Estates Drive, Winter Garden
$1,499,900
5 Beds ⋅ 5 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
Virtually Staged. EXCEPTIONAL LUXURY IN THE HEART OF WINTER GARDEN! Welcome to this stunning 5-bedroom, 4.5-bathroom pool home nestled within Canopy Oaks, an exclusive, Parade of Homes award-winning gated community featuring just 49 residences. This beautifully upgraded Lockhart II model delivers an exceptional blend of elegance, comfort, and sophistication, featuring TWO luxurious primary suites, one on each floor, a 3-car garage, and private front and rear balconies. Step through the magnificent arched double doors into a breathtaking two-story foyer, where timeless architectural details and modern finishes set the tone. The thoughtfully designed interior showcases a versatile office or flex space, an exquisite wine cellar with authentic Chicago brick flooring, and a gourmet kitchen featuring a 5-burner natural gas cooktop and oversized island. A beautiful wooden staircase with custom forged-iron railings leads upstairs to generously sized bedrooms, a spacious primary suite with an impressive walk-in closet, and a dedicated home theater complete with a movie projector. RECENT UPGRADES includes 2025 A/C system, contemporary light fixtures, updated countertops, fresh interior paint, new downstairs flooring, custom closets, and a beautifully remodeled backyard. Step outside into your private retreat, featuring a sparkling pool and an inviting setting for entertaining or unwinding. LOCATION IS EVERYTHING! Just minutes from Winter Garden Village and Historic Downtown Winter Garden, enjoy convenient access to premier shopping, exceptional dining, and entertainment. With easy connections to Florida’s Turnpike, SR 429, SR 408, and Highway 50, the best of Central Florida is within easy reach. Luxury, exclusivity, and an unbeatable location come together in one extraordinary home. Schedule your private showing today!

665 Canopy Estates Drive, Winter Garden
15633 Panther Lake Drive, Winter Garden
$2,395,000
4 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
**Organic Modern Design. Intelligently Connected. Effortlessly Luxurious.** Discover extraordinary lakefront living in Winter Garden's Lakeshore Preserve community. Reimagined with nearly $1 million in renovations, this stunning residence blends sophisticated design, intelligent technology, and five-star resort-inspired living. Featured in *The Local Magazine's 2026 Home Issue*, the home showcases organic modern design with European and Mediterranean influences. Limewash walls, graceful archways, wide-plank flooring, custom millwork, and designer lighting create a warm, sophisticated atmosphere. A sculptural staircase with sweeping curved walls and a dramatic cascading chandelier makes an unforgettable statement. The beautifully appointed kitchen features custom cabinetry, premium JennAir appliances, a double-stacked quartz island, quartz backsplash, and beverage refrigeration. A walk-in pantry and drop zone add functionality. The primary suite offers a spa-inspired bath with a freestanding soaking tub, programmable shower, and custom California Closets. Additional highlights include a designer laundry room, upstairs entertainment loft, and equipped home gym with sauna. What truly sets this home apart is its seamless integration of technology. Control4 automation connects customizable Philips Hue lighting, Sonos audio, motorized shades, smart thermostats, security, and other features, making everyday luxury feel effortless. Outdoors, an infinity-edge pool with cascading waterfall overlooks Panther Lake. A two-level pool deck, covered entertaining areas, outdoor fireplace, integrated speakers, and motorized lanai screens create a private resort experience. Architectural lighting and a mosquito misting system add comfort and ambiance. Additional features include a whole-house generator, climate-controlled garages, EV charging, extensive security, and a professional smart-home technology transfer service for the new owner. Lakeshore Preserve offers included lawn care and a convenient location near Walt Disney World and SR 429

15633 Panther Lake Drive, Winter Garden
14503 Avenue Of The Rushes, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ Signature Lakes SubDv. ⋅ 34787 Zip Code
Pro Pics Coming Soon - 1st time on the market * Welcome to this beautiful and incredibly maintained home offering 4 bedrooms, 3.5 bathrooms, and approximately 3,315 square feet of living space in the desirable Signature Lakes community of Independence * Built in 2007, this spacious two-story home offers an inviting blend of comfort, style, and room to entertain * Attractive curb appeal, a welcoming covered entry, paver driveway, and tropical landscaping create a memorable first impression * Inside, the generous floor plan provides flexibility for everyday living, entertaining guests, and enjoying the Florida lifestyle * Step outside to the private screened pool area and create your own backyard retreat, perfect for relaxing and enjoying the sunshine year-round * Conveniently located near shopping, dining, major roadways, and the many amenities of Winter Garden, this property offers an excellent opportunity to enjoy the Central Florida lifestyle, with community recreation and outdoor activities. Community amenities include a clubhouse, 2 resort-style swimming pools, fitness facilities, tennis and basketball courts, playgrounds, parks, and community boat ramps and docks providing access to Lake Hancock.

14503 Avenue Of The Rushes, Winter Garden
2010 Boss Hewett Street, Oakland
$1,450,000
5 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code
Beautiful 2022-built home in Hull Island featuring 5 bedrooms, 4 full bathrooms, approximately 3,781 heated square feet, a private pool, and a two-car garage. Open-concept living with a gourmet kitchen, quartz countertops, a spacious loft, and two primary suites, including one on the first floor. Community amenities include a pool, trails, playground, dog park, and private dock. Buyer to verify all measurements, HOA terms, and property details.

2010 Boss Hewett Street, Oakland
2139 Tillman Avenue, Winter Garden
$825,000
4 Beds ⋅ 4 Baths ⋅ Bronsons Landing SubDv. ⋅ 34787 Zip Code
STOP YOUR SCROLL!!! It's not everyday a GORGEOUS home inside the beautiful gated community of Bronson's Landing is available but this Pool Home offers SO MUCH! This 4 bedroom PLUS OFFICE and POSSIBLE 5th BEDROOM home has 4 FULL bathrooms with multiple living spaces, multiple dining areas as well as an extra large 3 car garage. At the heart of the home is the spacious kitchen with an island, perfectly positioned between the main living areas and designed for both everyday life and entertaining. You’ll find granite counter tops, a large center island, double ovens, plenty of cabinetry, and a pantry. One of the best features is that the primary suite and three additional bedrooms are all located on the main floor. The primary bedroom feels like its own private retreat on it's own side of the house with two walk-in closets, dual vanities, a soaking tub, and separate shower. Being a split floor plan, 2 bedrooms share a Jack-and-Jill bathroom that makes this home super functional. This home can easily handle generational living. Upstairs, the over-sized bonus room with its own full bathroom gives you even more possibilities. Use it as a game room, movie room, guest suite, home gym, second office, or even a possible 5th bedroom. There is plenty of flexibility to make the space work for your lifestyle. The backyard is where the Florida lifestyle really shines! Step outside to your own private oasis with a screened saltwater pool, covered lanai, paver deck, and convenient pool bath. The home backs to a beautiful tree-lined green space, giving you extra privacy and a peaceful setting with no home directly behind you. Imagine starting the morning with coffee by the pool, spending the afternoon soaking up the Florida sunshine, and ending the evening relaxing under the lanai. And YES! Location matters! Bronson’s Landing is a sought-after gated community in one of Winter Garden’s most desirable areas, with access to highly regarded schools and an amazing Central Florida location. You’re close to Winter Garden Village, shopping, dining, 429, and all the charm of Historic Downtown Winter Garden. ALSO! Walt Disney World is just a short drive away, making spontaneous trips to the parks, dinner at Disney Springs, or a night watching fireworks that much easier! This home gives you the space of a true family home, the privacy of a beautiful gated community, your own Florida pool, and easy access to everything that makes Winter Garden and the Disney area such a MAGICAL place to live. If you’ve been waiting for a home that offers space, flexibility, privacy with a pool, and a fantastic location, THIS IS THE ONE!

2139 Tillman Avenue, Winter Garden
14656 Pylon Court, Winter Garden
$2,300,000
7 Beds ⋅ 7 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful lake-view home in the desirable, gated Isles of Lake Hancock community in Horizon West / Winter Garden! This spacious 7-bedroom, 6.5-bathroom home offers approximately 4,634 square feet of living space on an oversized 0.43-acre lot, with beautiful lake views from both the front and back of the property. The first floor features a spacious primary suite with a sitting area and his-and-hers walk-in closets, three additional bedrooms with bathrooms, and a separate office perfect for working from home, and a formal dining area for family meals and entertaining.The split-bedroom floor plan offers added privacy and flexibility. Upstairs, you'll find three more bedrooms, two bathrooms, and a loft area, providing plenty of space for family and guests. The home also offers two separate garage spaces, with one currently enclosed and used as a gym that can be converted back into a garage if desired. Enjoy Florida living with a screened-in pool, summer kitchen, solar panels, and beautiful sunset views over the lake. Residents of this gated community enjoy tennis courts, playground and a private boat ramp. Lake Hancock is a nationally recognized water-skiing destination that hosts world-class tournaments. Located in the sought-after Horizon West / Winter Garden area, the community offers convenient access to Walt Disney World, shopping, dining, upscale golf courses, top-rated schools, and SR-429. With plenty of space, beautiful lake views, and a great location, this home has so much to enjoy. Schedule your private showing today!

14656 Pylon Court, Winter Garden
726 Regina Circle, Oakland
$695,000
5 Beds ⋅ 4 Baths ⋅ Johns Landing Ph 01 44/47 SubDv. ⋅ 34787 Zip Code
Welcome to 726 Regina Circle in Oakland, Florida! This spacious two-story home offers five bedrooms, four bathrooms, and an inviting layout designed to accommodate a variety of living needs. The interior features vaulted ceilings, a formal dining area, and comfortable living spaces, including a family room with a fireplace. The kitchen offers granite countertops, a breakfast bar, an island, and ample cabinetry, creating a functional space for everyday living and entertaining. The primary suite features an en-suite bathroom with dual vanities and a separate soaking tub and shower. Step outside to enjoy the private swimming pool and outdoor space, ideal for relaxing or entertaining guests. A two-car garage provides additional parking and storage. Conveniently located in the Oakland and Winter Garden area, the property offers access to nearby shopping, dining, parks, trails, and major roadways. Schedule your private showing and discover the possibilities this home has to offer.

726 Regina Circle, Oakland
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