Winter Garden Homes with Private Pool type

Winter Garden Homes with Private Pool type

Welcome to Winter Garden, Florida, a hidden gem nestled just a short drive from the bustling heart of Orlando. Known for its charming downtown area, vibrant community spirit, and picturesque landscapes, Winter Garden offers a delightful blend of small-town charm and modern conveniences. This city is surrounded by lush greenery and scenic lakes, providing residents with ample opportunities for outdoor recreation, from biking along the West Orange Trail to enjoying leisurely afternoons at the nearby Lake Apopka.

For those seeking the ultimate in luxury and relaxation, Winter Garden boasts an impressive selection of homes with private pools. Imagine stepping into your own backyard oasis, where you can unwind under the Florida sun or host memorable gatherings with family and friends. These homes are designed for both comfort and entertainment, featuring spacious layouts, modern amenities, and beautifully landscaped outdoor spaces.

The allure of a private pool not only enhances your lifestyle but also adds significant value to your property. Whether you prefer a serene morning swim or evening barbecues by the water, having a private pool transforms your home into a personal retreat. With a variety of styles and sizes available, you can find the perfect home that fits your needs and desires.

Winter Garden is not just a place to live; it’s a community that embraces a vibrant lifestyle. With top-rated schools, diverse dining options, and year-round events, you’ll find everything you need right at your fingertips. Explore the charm of Winter Garden and discover your dream home with a private pool today!

Newest Winter Garden Homes with Private Pool type

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
5513 New Independence Parkway, Winter Garden
$575,000
3 Beds ⋅ 2 Baths ⋅ Independence / Signature Lakes Ph 02 SubDv. ⋅ 34787 Zip Code
Nestled in the heart of the desirable Winter Garden, this beautifully updated 3-bedroom, 2-bathroom SALTWATER POOL HOME offers 1,920 square feet of thoughtfully designed living space, modern elegance, and an exceptional resort-style lifestyle! From the moment you arrive, you’ll fall in love with the picturesque curb appeal, lush landscaping, charming brick-paver walkway, and inviting covered front porch. Step inside to discover a bright, open-concept floor plan featuring beautiful bamboo flooring, abundant natural light, and inviting living spaces perfect for everyday comfort and entertaining. The heart of the home is the stunning kitchen, completely remodeled in 2019! Featuring gorgeous quartz countertops, rich cabinetry, stainless steel appliances, stylish pendant lighting, and an expansive island with seating, this space is designed for gathering and making memories. A charming, sun-filled dining nook completes the picture! Your own private backyard oasis awaits! Step through beautiful French doors to your sparkling SALTWATER POOL, surrounded by an expansive screened enclosure and spacious covered lanai. Whether you're enjoying a refreshing afternoon swim, hosting weekend gatherings, or relaxing in the shade, this outdoor retreat makes every day feel like a vacation! Additional highlights include a convenient rear-entry garage with a beautifully finished epoxy floor. The lifestyle doesn't stop at your front door! Enjoy RESORT-STYLE COMMUNITY AMENITIES and a vibrant calendar of year-round events, including themed movie nights, ice cream socials, fireworks, and seasonal celebrations. Even better, the HOA includes internet and cable. Ideally located in the beautiful Winter Garden, walkable to schools, shopping, dining, entertainment, and conveniently located to Central Florida attractions, this home offers the perfect blend of modern comfort, neighborhood charm, and Florida living. More than a home....it's a lifestyle! Schedule your private showing today! *Wine fridge and weather station on the lanai screen does not convey.

5513 New Independence Parkway, 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
8270 Topsail Place, Winter Garden
$849,900
4 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Luxury Single-Story Pool Home in Lakeshore Preserve | 4BR/3BA | Disney Fireworks Views Enjoy luxury living in this heavily upgraded Toll Brothers home in Lakeshore Preserve, featuring a private pool with a brand new pool heater, no rear neighbors, and views of Magic Kingdom fireworks. The light-filled, open floor plan features 12-foot ceilings, 8-foot doors, and upscale lighting throughout the kitchen, dining area, and great room. The gourmet kitchen offers upgraded cabinetry, a butler’s pantry, quartz countertops, stainless steel appliances, a built-in wall oven, and an impressive 12-foot center island. The owner’s suite overlooks the pool and includes two walk-in closets and a spa-style bathroom with dual vanities and a frameless glass shower. The flexible layout includes a dedicated office with a closet that can serve as the fourth bedroom, a private guest suite with an ensuite bathroom and walk-in closet, and a third full bathroom off the hall. Outside, your backyard retreat awaits with a private pool, extended screened lanai, and oversized covered patio pre-plumbed for a summer kitchen. Take in peaceful sunrise views and enjoy Magic Kingdom fireworks after dark. Lakeshore’s resort-style amenities include a lakefront clubhouse, event room, fitness and yoga rooms, meditation room, zero-entry community pool with splash features, summer kitchen, sand volleyball, dock, trails, playgrounds, parks, fire pit, dog park, and kayak launch. Dining, shopping, schools, golf, and area attractions are just minutes away. HOA includes Wi-Fi and lawn care. Minutes to dining, shopping, schools, golf, and area attractions. Available for immediate occupancy; contact for a private showing.

8270 Topsail Place, Winter Garden
816 E Fullers Cross Road, Winter Garden
$1,150,000
4 Beds ⋅ 4 Baths ⋅ Crown Point Town SubDv. ⋅ 34787 Zip Code
Rare gated, custom-built home on an oversized 1.28-acre lot within the Winter Garden golf cart district. This property is a dream for an investor or family planning for a multi-generational property. The primary residence is over 3000 sq. ft with 4 bedrooms, 3.5 bathrooms and a two-car garage. Additionally, it includes a permitted pad for a four-car garage, which currently serves as both a basketball court and an outdoor entertainment area perfect for hosting large gatherings. The original plat had 6 houses, and the current layout would be ideal for adding an ADU. Buyer to contact city for permitting/building regulations. Finding property near downtown Winter Garden or close to the West Orange Trail with space to play a game of soccer, football, or volleyball in the front or back yard is nearly impossible. The property is fully fitted with a saltwater pool, raised bed gardens, tire swing, and other outdoor amenities. It's perfect for the green thumb with a litany of fruiting trees and shrubs. This is a once in a generation opportunity to customize a lot-set home with country-style living adjacent to one of the most desirable downtown districts in Orlando. Roof 2018, AC units 2025 & 2026, Hot Water Heater 2021.

816 E Fullers Cross Road, Winter Garden
725 Tranquil Trail, Winter Garden
$669,000
5 Beds ⋅ 3 Baths ⋅ Black Lake Park Ph 02 SubDv. ⋅ 34787 Zip Code
Enjoy the best of Winter Garden living in this inviting pool home, ideally situated in the desirable gated community. Located in a premier area close to shopping, dining, entertainment, and everyday conveniences, this home combines spacious interiors, welcoming curb appeal, and a backyard made for enjoying the Florida lifestyle. A striking exterior, tropical landscaping, and a covered front entry create a memorable first impression. Inside, abundant natural light, soft interior colors, and attractive flooring lend warmth to the main living spaces. The thoughtfully arranged two-story layout offers room to gather, entertain, and unwind, with a welcoming front living area and an open kitchen, dining, and family room that keep the heart of the home connected. The kitchen is a standout, featuring wood cabinetry, stainless steel appliances, recessed lighting, and a generous contrasting island topped with a light countertop. Ample cabinet storage and expansive work surfaces provide both style and practicality, while the adjoining dining area offers a comfortable setting for everything from casual breakfasts to holiday gatherings. Large windows and sliding glass doors brighten the surrounding living spaces and connect the interior to the backyard. Upstairs, a spacious loft adds valuable flexibility to the floor plan. Create a second lounge, media room, play area, or workspace tailored to your needs. The generously sized primary bedroom provides a relaxing retreat with room for a sitting area, while the additional bedrooms give versatility for guests, hobbies, or working from home. Step outside to discover one of the home’s most appealing features: a private backyard retreat with a swimming pool, raised spa, and an expansive paver deck. Spend sunny afternoons poolside, enjoy outdoor dining, or gather with friends beneath the evening sky. Privacy fencing, surrounding greenery, and lawn space complete this inviting setting, bringing together room for recreation and relaxation. This community enhances the lifestyle with gated entry and community amenities that include a swimming pool, playground, sports courts, and a community boat ramp and dock. Beyond the neighborhood, enjoy convenient access to Winter Garden Village’s shopping and restaurants, historic downtown Winter Garden, and major roadways connecting you to Orlando and Central Florida’s attractions. With its bright living spaces, flexible layout, appealing kitchen, and beautiful poolside setting, this home offers an exceptional combination of comfort and convenience in a sought-after Winter Garden location. Schedule your private showing.

725 Tranquil Trail, Winter Garden
15646 Sweet Lemon Way, Winter Garden
$1,950,000
5 Beds ⋅ 4 Baths ⋅ Highlands/Summerlake Grvs Ph 3 SubDv. ⋅ 34787 Zip Code
LAKEFRONT LUXURY, a PRIVATE POOL, and room to grow in sought-after Winter Garden! PRICED BELOW APPRAISED VALUE! BUILT IN 2021, this beautifully upgraded 5-bedroom, 3.5-bath home sits on an OVERSIZED .37 ACRE CUL-DE-SAC LOT overlooking SKIABLE LAKE HUCKLEBERRY in the Highlands at Summerlake Groves community. Surrounded by WOODED, LAKE, and POND VIEWS with minimal neighbors, this property offers a rare sense of privacy while keeping everyday conveniences close by. Lake Huckleberry is a 150-ACRE SKIABLE LAKE, and the county has approved a private dock to be built, opening the door to enjoying lake life right from your backyard! Beautiful landscaping, a PAVER DRIVEWAY, and inviting curb appeal welcome you home to a light-filled interior where thoughtful design meets comfortable luxury. Large-format MARBLE-LOOK TILE flows diagonally throughout the main living areas, complemented by crown molding, upgraded lighting, and elegant finishes. The OPEN CONCEPT living spaces are designed for effortless entertaining, with wide sliding glass doors connecting the indoors to the COVERED LANAI and SCREENED POOL. At the heart of the home, the UPGRADED GOURMET KITCHEN impresses with timeless cabinetry, glass-front display cabinets, crown molding, elegant countertops, a large ISLAND with seating, decorative tile backsplash, BUILT-IN GAS COOKTOP, stainless steel range hood, and statement pendant lighting. Your MAIN FLOOR PRIMARY SUITE offers a private retreat with a spacious en-suite bath featuring a double vanity and huge glass-enclosed, custom-tiled WALK-IN SHOWER with a built-in bench and rain shower head. Flexible living spaces include a formal dining area, FLEX/FAMILY ROOM, and an additional OFFICE or MAIN FLOOR BEDROOM converted from the original single-car side-load garage, ideal for working from home or creating a space that fits your needs. A PROFESSIONAL-GRADE ARAKNIS ROUTER AND WHOLE-HOME WI-FI SYSTEM keep you connected throughout the home. A custom BUILT-IN MUDROOM/DROP ZONE adds everyday convenience, while decorative iron staircase balusters, wood handrails, crystal-style chandeliers, and window blinds throughout bring character and style. Outside, your backyard feels like a private resort! Relax under the covered lanai, cool off in the sparkling pool with mosaic tile detailing, or entertain on the expansive paver deck, all within a screened enclosure featuring PANORAMIC SCREEN PANELS that showcase the lake and peaceful natural surroundings. A 6-FOOT BLACK ALUMINUM FENCE surrounds the side and rear yards, defining the outdoor space while preserving the open views. Located in the Highlands at Summerlake Groves, this home offers easy access to SR 429, shopping, dining, and all that Winter Garden has to offer, with sought-after A-RATED SCHOOLS – Summerlake Elementary, Hamlin Middle, and Horizon High. BONUS ~ FURNISHINGS ARE NEGOTIABLE! Spacious, beautifully appointed, and perfectly positioned for lakefront living, this is a home that truly offers something special!

15646 Sweet Lemon Way, Winter Garden
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