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

$375,000
2 Beds 3 Baths Orchard Hills Ph 4 SubDv. 34787 Zip Code
Welcome to Cypress Hill Road, featuring a beautifully maintained townhome located in the highly desirable Horizon West area of Winter Garden. Built in 2018, this move-in-ready residence offers approximately 1,594 square feet of thoughtfully designed living space featuring 2 spacious bedrooms, 2.5 bathrooms, and a rear-entry two-car garage. Step inside to discover an open-concept floor plan that seamlessly blends the living, dining, and kitchen areas, creating the perfect space for both everyday living and entertaining. Pride of ownership is evident throughout, with the home having been exceptionally maintained and cared for. Upstairs, you'll find two generously sized bedroom suites, each designed for comfort and privacy. The spacious secondary bedroom is a standout feature, offering its own private en-suite bathroom and a large walk-in close, making it ideal for guests, roommates, or a growing family. The primary suite provides a relaxing retreat with ample space and storage. Outside, enjoy the low-maintenance lifestyle that townhome living provides while taking advantage of the incredible community amenities nearby. Residents enjoy access to resort-style amenities, including community pools, playgrounds, walking trails, parks, sports courts, and beautifully maintained common areas that make this one of Winter Garden's most sought-after communities. Conveniently located near shopping, dining, entertainment, major roadways, and top-rated schools, this home places you in the heart of everything Horizon West and Winter Garden has to explore. Don't miss your opportunity to own this meticulously maintained townhome in one of Central Florida's most desirable locations. Schedule your private showing today!

5863 Cypress Hill Road, Winter Garden

$550,000
4 Beds 3 Baths Highland Rdg Ph 2 SubDv. 34787 Zip Code
SPECIAL FINANCING AVAILABLE! The seller is offering a promotional 3.875 interest rate through a rate buy-down program, plus ALL closing costs paid when using the preferred lender—creating an incredible opportunity for qualified buyers to significantly reduce their monthly payment and cash needed at closing. Welcome to this stunning newer construction home located in the highly desirable Horizon West area of Winter Garden! Nestled in one of Central Florida’s most sought-after communities, this beautiful two-story residence offers spacious open-concept living, soaring ceilings, and an abundance of natural light throughout. Designed for modern living, the home features expansive living and dining areas, generously sized bedrooms, and a functional floor plan perfect for entertaining or everyday comfort. Enjoy outdoor living with a semi-private fenced backyard, providing the perfect balance of privacy and open space. Ideally situated just minutes from Flamingo Crossings, Walt Disney World, shopping, dining, entertainment, and major highways, this location offers unmatched convenience and lifestyle. Residents also benefit from access to highly rated A+ schools, making this an excellent choice for families. Don’t miss this incredible opportunity to own a beautiful home in one of Winter Garden’s fastest-growing and most desirable neighborhoods. Schedule your private showing today!

14123 Frasier Street, Winter Garden

$725,000
4 Beds 4 Baths Lakeview Preserve SubDv. 34787 Zip Code
Experience elevated Florida living in this beautifully upgraded Lakeview Preserve home, where luxury, efficiency, and low-maintenance comfort come together seamlessly. Featuring a fully owned solar energy system complete with dedicated NEMA 14-50R for your EV, this thoughtfully enhanced residence offers exceptional value with no solar lease or financing to assume. Inside, an open-concept design welcomes you with upgraded flooring, elegant tray ceilings, custom feature walls, and abundant natural light. The spacious living area is highlighted by a stylish electric fireplace, creating a warm and inviting gathering space. The gourmet kitchen is designed for both everyday living and entertaining, featuring luxury stainless steel appliances, ample cabinetry, and seamless flow into the dining and family rooms. The private owner’s suite provides a relaxing retreat with a well-appointed ensuite bath, while the versatile floor plan offers flexibility for growing families, multi-generational living, remote work, or visiting guests. Step outside to your own backyard oasis featuring premium artificial turf for year-round beauty without the upkeep. A dedicated area is perfectly manicured for putt-putt, bocce, corn hole and other outdoor games while powered/motorized awnings and a lanai sunshade create the perfect setting for outdoor dining, entertaining, or relaxing evenings. Permanent exterior accent lighting adds curb appeal and convenience throughout the year. Additional highlights include an extended two-car garage, luxury appliance package, and numerous owner-selected upgrades throughout. Residents of Lakeview Preserve enjoy resort-style amenities including a community pool and cabana, splash pad, fitness center, playground, walking trails, and access to Johns Lake for kayaking, canoeing, and fishing. Conveniently located just minutes from Downtown Winter Garden, shopping, dining, top-rated schools, and SR-429, this home offers the perfect blend of tranquility and accessibility. Rarely does a home combine energy efficiency, premium upgrades, and an exceptional lifestyle in one of Winter Garden’s most desirable communities. Schedule your private showing today.

3447 Current, Winter Garden

$495,000
3 Beds 2 Baths Alexander Rdg SubDv. 34787 Zip Code
Virtually Staged. Back on market buyer's financing fell through. Welcome to 1950 Pantheon Drive, a charming 3-bedroom, 2-bath home located in the desirable Alexander Ridge community of Winter Garden. Offering 1,769 square feet of living space, this thoughtfully designed split-bedroom floor plan provides comfort, privacy, and easy everyday living. From the moment you arrive, the home makes a welcoming first impression with a bright exterior, paver driveway, covered entryway, mature landscaping, and a large front tree that adds shade and curb appeal. Inside, the open living, kitchen, and dining areas create a functional flow for relaxing, gathering, and entertaining. The living room features warm engineered wood flooring, neutral tones, and natural light from multiple windows, creating a bright and inviting main living space. The kitchen overlooks the living area and features granite countertops, warm wood cabinetry, stainless steel appliances, pendant lighting, recessed lighting, a breakfast bar, a center island, a deep kitchen sink, and a modern pull-down faucet.  Just beyond the kitchen, the dining area provides a dedicated space for meals while remaining connected to the heart of the home. The private primary suite offers neutral tones and direct access to the ensuite bathroom. The primary bath features dual sinks, granite countertops, warm wood cabinetry, upgraded lighting, a walk-in shower with a glass enclosure, a separate soaking tub, and direct access to the walk-in closet. The walk-in closet also includes convenient door access to the laundry room, adding a smart everyday function. Bedrooms 2 and 3 are located on the opposite side of the home and share a spacious second bathroom. Recent updates include HVAC replaced in August 2024, PAID OFF Solar Panels in 2018, ROOF installed in 2023. The solar system is paid off, helping create an energy-efficient home with low-cost utilities. Alexander Ridge offers inviting community amenities, including a resort-style pool with paver decking, lounge areas, a covered pavilion, playground, open green space, and beautifully maintained common areas surrounded by mature landscaping and palm trees. This Winter Garden home blends comfort, function, efficiency, and community living in one inviting package.

1950 Pantheon Drive, Winter Garden

$510,000
3 Beds 3 Baths Signature Lakes Ph 3b-4, 3b-5 & SubDv. 34787 Zip Code
Welcome to 15183 Bridgewater Crossings Blvd, a 3-bedroom, 2 full/1 half bath home with a versatile bonus room featuring newly installed sliding barn doors, perfect for a home office, playroom, or guest space. Fresh exterior and interior paint, new ceiling fans and crown molding in the living room, kitchen, and primary bedroom add character throughout. Enjoy Florida living from your fully fenced in backyard with rear porch, or relax on your front porch, where you can view the nightly Disney fireworks. Located in the highly desirable Horizon West area, this amenity-rich community offers two pools, two clubhouses with fitness centers, an arcade room, billiards, tennis, basketball courts, dog parks, walking and bike paths, expansive green spaces, and a community boat ramp with access to Lake Hancock. HOA INCLUDES CABLE and Wi-Fi. Enjoy exceptional convenience with SR 429 minutes away, providing quick access throughout Central Florida. Minutes from Hamlin Town Center, where you can enjoy the new recreational destination Horizon West Regional Park, PopStroke, Cinepolis, shopping & dining galore, the new Horizon West Library and Orange County National Golf. Bonus... you are so close to the magic of Downtown Winter Garden, Disney World and zoned for top-rated schools. This home offers the perfect blend of comfort, recreation and location! ALL INFORMATION CONTAINED HEREIN IS FROM SOURCES DEEMED RELIABLE, HOWEVER, NO REPRESENTATION OR WARRANTY IS MADE TO THE ACCURACY THEREOF.

15183 Bridgewater Crossings Boulevard, Winter Garden

$170,000
2 Beds 2 Baths Grove Resort And Spa Hotel Condominium SubDv. 34787 Zip Code
Calling ALL Snowbirds & Anyone Looking For A Florida Experience! * This Condo Is An INCREDIBLE VALUE For A Resort Style Stay For Up To Half The Year! Then Turn It Into Your Orlando Investment Dream For The Other Half Of the Year! * Imagine Waking Up To This Nature View From Up On This 5th Floor. Enjoy Your Morning Coffee Or * FIREWORKS * View At Night! Unit 1527 Is Located Immediately Next To The Condo Walkway, Which Overlooks Out Into Nature And Water View. Upon Entering This 2 Bedrooms/2 Bathrooms Condo, Be Greeted With A View Of The Balcony! The Condo Has A Grand Kitchen That Is Fully Stocked With Cooking Utensils & Coffee Machine. * Kitchen Has Stainless Steel Appliances And Long Granite Countertops With Tons Of Storage Space. *Living Room And *Dining Room Combo Has A Great Entertaining Space. Kickback & Watch A Movie While Peering Out Through The Window To See Disney's Nightly Fireworks! That's Incredible! *Bedrooms Are Fully Furnished With A Full Bathrooms And Massive Walk-In Closet. * Water Heater 2008 * HVAC 2021 * Condo Amenities Are Included! Water Parks, Gym, Water/Electricity, And MUCH More. Conveniently Located ~ 7 Miles To Walt Disney World, ~ 4 Miles To Flamingo Crossings Town Center, ~ 20 Miles From Winter Garden Village At Fowlers Grove & West Orange Trail, And ~10 Miles To Interstate 4 (I-4)! This Fully Furnished Condo Won’t Last! * Priced To Sell! * Book Your Showing Today!

14501 Grove Resort Avenue Unit 1527, Winter Garden

$656,500
4 Beds 4 Baths Lakeshore Preserve Ph 1 SubDv. 34787 Zip Code
Welcome to a beautifully upgraded residence in Lakeshore Preserve, one of Horizon West premier Toll Brothers communities. Perfectly positioned in the heart of Winter Garden’s most desirable growth corridor, this home offers the rare combination of refined design, intelligent functionality, and private outdoor living. With over 2,500 square feet of thoughtfully designed space, this home stands apart from the ordinary. From the moment you enter, the quality is evident. Designer lighting, premium flooring, upgraded interior doors, extensive trimwork, crown molding, wainscoting, and a custom accent wall create a polished, elevated feel throughout. Every detail has been carefully selected to add warmth, character, and sophistication. The heart of the home flows beautifully for everyday living and entertaining, while the private courtyard creates a true outdoor retreat. Enhanced by a full breezeway and additional separation from the adjoining residence, this space offers a level of privacy rarely found in this style of home. Whether enjoying morning coffee, evening wine, or quiet time outdoors, the courtyard feels like your own secluded escape. One of the home’s most valuable and unique features is the detached garage with an impressive private suite above, offering nearly 500 square feet of flexible living space. Complete with a spacious bedroom area, family room, ensuite bath, walk-in closet, and wet bar with both upper and lower cabinetry, this suite is ideal for guests, extended family, a private office, studio or media room. This is not just another home in Lakeshore Preserve. It is a thoughtfully upgraded property with exceptional use of space, privacy, and versatility. For buyers seeking luxury, comfort, and function in one of Winter Garden’s most desirable communities, this residence is a must-see. Experience the lifestyle, the quality, and the rare flexibility this home offers

8878 Bismarck Palm Drive, Winter Garden

$719,000
5 Beds 3 Baths Johns Lake Pointe SubDv. 34787 Zip Code
Welcome to 552 Egret Place in beautiful Winter Garden, Florida—an exceptional Meritage Homes residence thoughtfully designed to combine modern style, everyday comfort, and outstanding energy efficiency. From the moment you arrive, you'll appreciate the quality craftsmanship and attention to detail that Meritage Homes is known for. Inside, an open and inviting floor plan creates the perfect setting for both daily living and entertaining. The spacious living areas flow seamlessly into the well-appointed kitchen, featuring abundant cabinetry, generous counter space, a large island, and modern finishes that make gathering with family and friends effortless. The private owner's suite provides a peaceful retreat with a spacious bedroom, an elegant en-suite bath, and a generous walk-in closet. Additional bedrooms provide flexibility for family, guests, or a dedicated home office. One of the standout features of this home is its energy-efficient construction. This home incorporates advanced energy-saving features designed to provide year-round comfort while helping reduce utility costs. Spray foam insulation and energy efficient windows are just some of the certified features that contribute to a more efficient home. Step outside to enjoy the outdoor living space—ideal for morning coffee, weekend barbecues, or simply relaxing while enjoying Florida's beautiful weather. Located in one of Winter Garden's most desirable areas, you'll enjoy convenient access to top-rated schools, shopping, dining, parks, major highways, and the charm of Historic Downtown Winter Garden, known for its award-winning farmers market, local restaurants, boutique shopping, and the West Orange Trail. Whether you're looking for a move-in-ready family home or a smart investment in one of Central Florida's fastest-growing communities, 552 Egret Place offers the perfect blend of quality construction, energy efficiency, modern amenities, and an unbeatable location. Don't miss this opportunity to own a beautifully crafted home where comfort, savings, and Florida living come together.

552 Egret Place Drive, Winter Garden

Start Your Search