Winter Garden Homes with Private Pool type

Winter Garden Homes with Private Pool type

Winter Garden, located in the state of Florida, is a charming city that offers a perfect blend of natural beauty, rich history, and modern amenities. Known for its warm climate and picturesque landscapes, Winter Garden is a sought-after destination for those looking to settle down in the Sunshine State.

One of the standout features of Winter Garden is its abundance of homes with private pools. If you're someone who enjoys the luxury and convenience of having your own pool, Winter Garden is the place to be. Whether you're looking for a cozy single-family home or a spacious estate, you'll find a variety of options that cater to your desire for a private oasis.

Having a private pool in your home not only provides a refreshing escape during the hot summer months but also adds value to your property. It's an excellent feature for entertaining guests, hosting pool parties, or simply enjoying some quality family time. Imagine lounging by the poolside, sipping a cool drink, and soaking in the Florida sun - it's the epitome of relaxation and indulgence.

Winter Garden offers a range of homes with private pools to suit different tastes and budgets. From modern and contemporary designs to traditional and classic styles, you'll find a variety of architectural options to choose from. Additionally, many of these homes are nestled in beautiful communities that offer additional amenities such as parks, playgrounds, and walking trails.

If you're considering a move to Winter Garden, the availability of homes with private pools is certainly a compelling factor. Not only will you enjoy the benefits of year-round sunshine and a vibrant community, but you'll also have the luxury of a private pool right in your backyard. Start exploring the real estate market in Winter Garden and find your dream home with a private pool today.

Newest Winter Garden Homes with Private Pool type

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 den, 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
15023 Guava Bay Drive, Winter Garden
$835,000
5 Beds ⋅ 4 Baths ⋅ Watermark Ph 4a SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully 2021-built home offering 4 bedrooms, 3.5 bathrooms, and versatile living spaces designed for modern Florida living! The first floor features tile flooring, a dedicated den ideal for a formal dining room, home office, or playroom, a welcoming family room, and a guest suite. Upstairs, a spacious bonus room provides additional flexibility for a media room, game room, or secondary living area. Step outside to your private, screened-in, heated swimming pool and covered lanai, perfect for relaxing, entertaining, and enjoying Florida’s year-round outdoor lifestyle with a view of Disney fireworks on your backyard. Additional highlights include a 2-car garage with epoxy flooring, an Universal EV charger, and an outdoor summer kitchen. Located in a growing Central Florida area, this home offers an opportunity to enjoy today’s lifestyle while keeping an eye on the area’s future development, including planned residential, commercial, and infrastructure projects that continue to shape the region. Conveniently located near the SR 429 exit toward Tampa, this home in the desirable Watermark community offers easy access to major roadways and every convenience. Across the street is the highly regarded Panther Lake Elementary with the HorizonWest High School right next door, walking distance. Enjoy the proximity with the The Mark, that features a pharmacy, gas station, Starbucks, and restaurants only a mile way. Nearby is the Hamlin Town Center's shopping, dinning, entertainment, brand new Library,and the nearby parks and recreational amenities. This property offers a wonderful combination of convenience, lifestyle, and accessibility.

15023 Guava Bay Drive, 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
900 Allendale Lane, Oakland
$1,799,000
4 Beds ⋅ 5 Baths ⋅ Oakland Parkb-2 SubDv. ⋅ 34787 Zip Code
Beautifully crafted by J&J Building, this exceptional 4-bedroom, 4.5-bath custom home combines thoughtful design, elegant finishes, and effortless indoor-outdoor living. Situated on a desirable corner lot, the home is filled with incredible natural light and offers a layout designed for both everyday comfort and entertaining. At the heart of the home, the stylish kitchen is complemented by a wet bar and a full scullery (back kitchen) with a second refrigerator, oven, sink and built-in pantry, creating the perfect blend of style and functionality. The main-level primary suite provides a private retreat, while three additional upstairs bedrooms each feature their own en-suite bathroom, offering comfort and privacy for family and guests alike. The downstairs office and upstairs loft area also provide flexible options to meet all your needs. The oversized attic storage with drop down stairs is perfect for all your seasonal items! Step outside to your own private oasis through the huge pocketing sliding glass doors, and enjoy the salt water pool, spa, and inviting outdoor living space with automated retractable screens—ideal for enjoying Florida living year-round. And the large garage has 2 EV plugs and 2 garage doors- 1 perfect for your golf cart! Just across the street, a beautiful pond provides a peaceful natural backdrop, with scenic sunset views and abundant wildlife adding to the home's special setting. Enjoy an exceptional lifestyle just steps from the West Orange Trail and within the Golf Cart District, offering convenient access to downtown Winter Garden's charming shops, restaurants, and vibrant community atmosphere. A rare opportunity to enjoy custom craftsmanship, beautiful surroundings, and an unbeatable location—all in one remarkable home.

900 Allendale Lane, Oakland
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
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