Explore Winter Garden, FL Homes for Sale

Winter Garden, FL with a Pool for Sale Map Search

Homes for Sale with a Pool in Winter Garden, FL

Welcome to your dedicated resource for homes for sale with a pool in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

< Back to all Homes for Sale in Winter Garden, FL

All Homes for Sale with a Pool in Winter Garden, FL

$996,975
3 Beds 3 Baths Country Lakes SubDv. 34787 Zip Code
Virtually Staged. Rarely does a property offer over an acre of land in the heart of Winter Garden. Tucked away in an intimate lake-access community, this beautifully refreshed pool home combines privacy, mature trees, and an unbeatable location just minutes from everything Central Florida has to offer. Set on a beautifully landscaped 1.1-acre lot with no rear neighbors, this stunning residence offers a rare opportunity to enjoy space, serenity, and flexibility in one of Winter Garden's most desirable locations. Designed for both everyday living and effortless entertaining, the home features fresh interior paint, new luxury vinyl plank flooring throughout the main living areas and bedrooms, a newer roof, new water heater, oven, range, custom woodwork, and a beautiful wood-burning brick fireplace that anchors the living space. The expansive covered lanai, refinished screened-in pool with a new pump, and spa create a true indoor-outdoor lifestyle, with multiple access points from the home and a kitchen pass-through window that opens directly to the entertaining area. Privately situated on the opposite side of the main 3 bedrooms, the light-filled bonus room features two closets, French doors, its own exterior entrance, and tranquil views of the mature landscaping. Paired with the adjacent full bath, it offers exceptional flexibility as a potential 4th bedroom, private guest suite, in-law suite, home office, or creative space. The 3rd full bath also serves as a convenient pool bath with direct outdoor access to the lanai. Outside, enjoy beautifully maintained gardens, mature trees, a fully fenced backyard, abundant outdoor living space, and a large detached storage building with electricity. Residents also enjoy private access to Black Lake and Lake Tilden, complete with a boat ramp, tennis court, pavilion, and the peaceful charm of one of Winter Garden's hidden-gem communities. Just minutes from Winter Garden Village, historic Downtown Winter Garden, major highways, area hospitals, and world-famous attractions including Disney World, Universal Orlando, and SeaWorld, this property delivers a combination of land, location, and lifestyle that is rare to find.

14140 Country Estate Drive, Winter Garden

$540,000
3 Beds 3 Baths Silverleaf Reserve Bungalows SubDv. 34787 Zip Code
Located in the highly desirable Silverleaf at Hamlin in Winter Garden, this exceptional bungalow offers the perfect blend of location, lifestyle, and design. Surrounded by top-rated schools within short distance, premier dining, and a rapidly growing area with strong appreciation, this is one of the most sought-after communities in the region. This beautifully designed home features 3 bedrooms, 2/1 bathrooms, and an additional loft room, with a layout that is both functional and inviting. What truly sets this property apart is its interior. Unlike anything else currently available in the area, this home has been fully customized with high-end finishes and a cohesive, thoughtfully curated design throughout. Every element was carefully selected to create a seamless flow of elegance, comfort, and functionality. The home showcases custom-built cabinetry in every space, including closets, storage solutions, and integrated desk areas, all designed specifically for the home. The custom-made curtains were designed to fit each space perfectly, enhancing both aesthetics and comfort. Throughout the home, you’ll find LED lighting and carefully selected fixtures that complement one another, creating a warm, modern, and visually harmonious atmosphere. Custom mirrors, wood panel details, and built-in elements elevate each room, making every space feel intentional and refined. The kitchen is a true highlight a gourmet, built-in design that is highly practical, ideal for everyday living and entertaining. This is a rare opportunity to own a home that is completely move-in ready at a level rarely found, and everything has already been done with impeccable taste. Simply bring your belongings and start living. Homes like this are truly one of a kind in the area, and once you step inside, it’s impossible not to fall in love.

4863 Lacewing Drive, Winter Garden

$333,000
3 Beds 3 Baths Tucker Oaks SubDv. 34787 Zip Code
Welcome to your new dream home! Located in the gated community of Tucker Oaks, this 2-story townhome offers 3 bedrooms, 2.5 bathrooms, and 1,544 square feet of comfortable, thoughtfully designed living space. As a corner unit backing to a peaceful conservation area, you’ll enjoy added privacy and tranquil views with no rear neighbors! Step inside to an open-concept first floor where high ceilings, recessed lighting, and natural light create a warm and inviting atmosphere. The layout is ideal for both everyday living and entertaining, with a seamless flow between the living, dining, and kitchen spaces. A conveniently located half bath downstairs adds ease and privacy when hosting guests. The kitchen is designed for functionality and style, featuring stainless steel appliances, crown-molded cabinetry, ample counter space, and a breakfast bar that’s perfect for quick meals or morning coffee. Upstairs, all bedrooms and full bathrooms are tucked away for optimal privacy. The primary suite offers a spacious retreat with a large closet and a private en suite bath complete with a generous vanity and a roomy shower, making it perfect for starting your day or winding down in the evening. Additional bedrooms provide comfortable space for family, guests, or a home office setup. Beyond the home, Tucker Oaks offers amenities including a community pool, playground, dog park, and sidewalks for enjoying the outdoors. The location places you just minutes from major highways, making commuting simple, while also being close to downtown Winter Garden where you can explore local farmers markets, community events, and boutique shopping. The nearby West Orange Trail offers even more ways to stay active and enjoy the Florida sunshine. With theme parks like Walt Disney World and Universal Studios just 25 minutes away, this home combines convenience, comfort, and lifestyle all in one. Don't wait on this amazing opportunity, schedule your private showing TODAY!!!

15316 Oak Apple Court Unit B, Winter Garden

$538,000
3 Beds 3 Baths Waterleigh Ph 1b SubDv. 34787 Zip Code
Welcome to the highly desirable Horizon West community of Waterleigh – Marina Bay, where lifestyle, convenience, and a true sense of community come together in one of Central Florida’s most sought-after neighborhoods. This beautifully upgraded south-facing Cordale model is move-in ready and thoughtfully designed, offering a perfect blend of style, comfort, and functionality for modern living. From the moment you arrive, you’ll appreciate the effortless curb appeal with HOA-included landscaping, allowing you to enjoy a pristine exterior year-round without the maintenance. Inside, the home immediately impresses with a clean, modern aesthetic and ZERO carpet throughout. Ceramic tile spans the main living areas, laundry room, and bathrooms, while matching hardboard vinyl plank flooring flows seamlessly through all bedrooms, the upstairs loft, and even the staircase, creating a cohesive and elevated look. Designed with both everyday living and entertaining in mind, the open-concept layout creates a warm and inviting atmosphere. The living room features a stunning modern accent wall that serves as a stylish focal point, while the primary suite offers its own beautifully designed accent wall, creating a private retreat with a touch of luxury. The kitchen is both functional and upgraded, complete with an enhanced stove and custom pantry shelving, while additional custom closet shelving throughout the home provides exceptional organization and storage. Step outside to your screened-in lanai and fully fenced backyard, perfect for relaxing evenings, entertaining guests, or creating a safe and enjoyable space for family and pets. Just outside your front door, a charming park offers a peaceful setting to unwind and even catch nightly fireworks from Walt Disney World, adding a little extra magic to your everyday life. Waterleigh offers an unmatched resort-style lifestyle, with amenities including a community pool, fitness center, scenic trails, clubhouse, dock, volleyball court, community garden, dog park, playground, and more. Residents also enjoy access to additional amenities throughout the greater Waterleigh community, along with a full calendar of events that bring neighbors together year-round. Location is everything, and this home delivers with quick access to FL-429, making commuting a breeze while keeping you close to top-rated dining, shopping, and everyday conveniences. Zoned for highly sought-after A-rated schools, this home is an exceptional opportunity for families looking to combine comfort, style, and community in one perfect place. This is more than just a home, it’s a lifestyle opportunity in one of Horizon West’s most vibrant communities. Don’t miss your chance to own this beautifully upgraded, move-in ready home in Waterleigh. Schedule your private tour today!

16197 Wind View Lane, Winter Garden

$1,219,000
4 Beds 4 Baths Lakeshore Preserve Ph 4 SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. EXPERIENCE ELEVATED LAKEFRONT LIVING IN THE HEART OF HORIZON WEST!!! Welcome to 15594 Shorebird Lane, an exceptional Toll Brothers lakefront residence located in the Lakeshore Preserve community of Winter Garden. Perfectly positioned on a premium oversized 0.34-acre homesite overlooking beautiful Panther Lake, this stunning 4-bedroom, 3.5-bath home offers over 3,000 square feet of thoughtfully designed living space, breathtaking water views, and nightly Disney fireworks from your own backyard. From the moment you enter the grand two-story foyer, you'll be captivated by the home's elegant design, abundant natural light, and seamless connection between indoor and outdoor living. The open-concept floor plan showcases a spacious great room, gourmet chef's kitchen with oversized island, and expansive windows framing panoramic lake views throughout the main living areas. The luxurious first-floor owner's retreat serves as a private sanctuary featuring tranquil water views, custom closet systems, and a spa-inspired bathroom. Upstairs, a spacious loft provides endless possibilities as a media room, game room, home office, or secondary living space. Step outside and discover one of the most impressive outdoor living spaces in the community. The enormous 1,250-square-foot screened lanai creates the perfect setting for entertaining, relaxing in the hot tub, enjoying the peaceful fountain, or gathering around the fire pit while watching spectacular sunsets and Disney fireworks illuminate the night sky. Designed with comfort and efficiency in mind, the home features Fully paid solar panel system for substantial energy savings, Tankless water heater, Advanced foam insulation, Plantation shutters throughout, Built-in pest control system, Upgraded irrigation system, and Custom storage and closet solutions. Move-in ready condition! This beautiful gem includes RESORT-STYLE AMENITIES, Residents of Lakeshore Preserve enjoy an unmatched lifestyle with access to Resort-style swimming pool, State-of-the-art fitness center, Yoga and wellness studio, Clubhouse and gathering spaces, Sand volleyball courts, Playground and dog park, Community canoes and lake access, and walking, and biking trails. One of the greatest advantages of this home is its unbeatable prime location in the highly desirable Horizon West area: Minutes to Walt Disney World Resort, Approximately 15 minutes to Winter Garden Village's premier shopping, dining, and entertainment, Convenient access to Flamingo Crossings Town Center, Close to Hamlin Town Center featuring restaurants, retail, movie theater, and waterfront events, Near Orange County National Golf Center and Lodge, one of Florida's premier golf destinations, Easy access to SR-429, Florida's Turnpike, and I-4, Approximately 30 minutes to Orlando International Airport, Close to Downtown Winter Garden, known for its award-winning farmers market, boutique shopping, breweries, and dining. Whether you're seeking a luxury primary residence, a relocation destination, or simply a home that delivers unforgettable lakefront sunsets and resort-style amenities every day, this extraordinary property offers a lifestyle few homes can match. Wake up to sparkling lake views. Spend your evenings watching Disney fireworks. Live where every day feels like a vacation. It won't last. Schedule your showing today!

15594 Shorebird Lane, Winter Garden

$299,000
3 Beds 2 Baths Grove Residence & Spa Hotel Condo SubDv. 34787 Zip Code
RARE opportunity to own a TOP-FLOOR UNIT with SWEEPING LAKE VIEWS! This 3-bedroom, 2-bathroom Jasmine floor plan is located in The Grove Resort & Spa, one of Central Florida’s premier vacation investment communities. Just minutes from Disney World, with Universal Orlando and SeaWorld also nearby, this resort offers an unparalleled combination of luxury and convenience. Enjoy incredible amenities, including theFlowRider® surf simulator, a lazy river with waterfalls, multiple water slides, a zero-entry resort-style pool, private cabanas with poolside food and drink service, and an activity pool. Beyond the waterpark, the resort also features three large pools and a jacuzzi conveniently located near the unit’s building. After a day of excitement, guests can unwind at the Longboard Bar & Grill or take advantage of the resort’s many luxurious amenities. The unit itself boasts a beautifully designed, well-equipped kitchen, an open-concept layout, and comes FULLY FURNISHED for a seamless move-in or rental experience. The great room, master bedroom, and one of the additional bedrooms all feature stunning LAKE VIEWS, with the great room opening to a private balcony where you can relax and take in the scenery. The master suite offers a spa-like ensuite bathroom with a garden tub, separate tiled shower, and dual vanities. The split-bedroom layout ensures privacy, and the unit comes equipped with four large-screen TVs for entertainment. As a turn-key investment, this condo includes all bookings upon purchase, with on-site management handling hotel operations and maintenance, a truly hassle-free opportunity that generates immediate income. Schedule your showing today!

14501 Grove Resort Avenue Unit 1703, Winter Garden

$185,000
2 Beds 2 Baths Grove Resort SubDv. 34787 Zip Code
Welcome to your fully furnished, turn-key vacation retreat at The Grove Resort & Spa Orlando—a highly sought-after, full-service luxury resort located just minutes from Walt Disney World Resort. As part of the Walt Disney World Good Neighbor Hotel Program, this property offers exceptional appeal for both personal use and income-generating potential. This spacious 2-bedroom, 2-bathroom condo (Cypress/Jasmine model) offers over 1265 square feet of thoughtfully designed living space. Positioned on a high floor as a desirable corner unit, it features an open-concept layout with split bedrooms for enhanced privacy. The oversized primary suite includes a separate sitting area, while the guest bedroom is equipped with two queen beds. Altogether, the unit comfortably accommodates up to 8 guests—ideal for families and vacation renters. The interior showcases modern finishes throughout, including solid wood cabinetry, granite countertops in both the kitchen and bathrooms, stainless steel appliances, and the convenience of in-unit laundry. The condo is fully furnished and professionally decorated, making it truly move-in or rental ready. A screened-in private balcony offers peaceful views, perfect for relaxing after a day at the parks. Residents and guests enjoy access to world-class resort amenities, including a full water park with dual water slides, a FlowRider® double surf simulator, lazy river, multiple pools, splash zones, private cabanas, on-site restaurants and bars, spa, fitness center, arcade game room, mini golf, walking trails, and private access to Lake Austin. The resort also features a convenient marketplace and complimentary shuttle service to Disney parks. This condo operates under a condo-hotel model with an on-site professional rental management program, allowing owners to generate income when not using the property. Owners also benefit from VIP check-in privileges. Notably, all utilities are included in the monthly maintenance fee, simplifying ownership and expense management. Conveniently located just off U.S. Route 192, the property is close to a wide variety of shopping, dining, and entertainment options, and only about 4.3 miles from Margaritaville Resort Orlando. This is resort-style living at its finest—perfect as a vacation home, investment property, or both.

14501 Grove Resort Avenue Unit 1110, Winter Garden

Start Your Search