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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.

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

$443,190
3 Beds 3 Baths Silverleaf Oaks SubDv. 34787 Zip Code
Under Construction. Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Dahlia interior unit townhome, a new construction home that seamlessly combines luxury and convenience. This modern townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage, all complemented by our Move-In Ready appliance and window blinds package. The first floor is designed with entertainment in mind, offering an open-concept kitchen, café, and gathering room that flows together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Trenton Flagstone Cabinetry, a decorative tile backsplash, quartz countertops, and stainless-steel appliances, including a refrigerator. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, gathering room, bathrooms, and laundry room, is finished with elegant tile for both style and easy maintenance. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity, and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. The loft area provides the perfect space to unwind. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. With thoughtful design, high-end finishes, and a focus on everyday convenience, the Dahlia townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

6262 Sunny Time Avenue, Winter Garden

$219,000
2 Beds 2 Baths Townhomes Winter Garden SubDv. 34787 Zip Code
Presenting an affordable investment in the Winter Garden area between the infamous Plant St and Hwy 50! This larger 2 bedroom/2 bath condo provides convenience in the location added to the maintenance free exterior. It is a small quaint community with only 50 condos. The pool is large with depths up to 8 feet. The condo has been well maintained with upgrades. Whether you're a first-time homebuyer, looking for a winter home or searching for a fantastic investment opportunity, this home checks all the boxes. Location is everything…Just minutes from the award-winning Historic Downtown Winter Garden. On Saturday mornings make your way to the Winter Garden Farmers Market for all the fresh foods you can imagine, along with retail and cooked food items. Any day of the week head on over to the Plant St area for browsing boutiques, enjoying locally owned restaurants, coffee shops, breweries and year-round community events. Outdoor enthusiasts will appreciate easy access to the scenic West Orange Trail, offering miles of paved paths for walking, running and biking. Need to shop at the big box retail stores, head South to the popular Winter Garden Village, the ultimate shopping destination. Very close by is a Publix shopping center and an Aldi. Winter Garden continues to be one of Central Florida's most desirable communities thanks to its small-town charm, top-rated amenities, vibrant downtown, and convenient access to major highways, Orlando, world-famous attractions, shopping, dining and entertainment. Access to the Turnpike is a short distance away, along with the 429 Freeway (is the way to Disney) and the 408/I4 Freeway (is the way to Universal Studios). This property qualifies for low down payment programs for primary buyers. New roofs start August 2026!

320 Eron Way Unit 6, Winter Garden

$500,000
3 Beds 2 Baths Waterleigh Ph 3b 3c & 3d SubDv. 34787 Zip Code
Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.

16802 Oakboro Street, Winter Garden

$859,900
4 Beds 4 Baths Waterleigh Ph 2b SubDv. 34787 Zip Code
Welcome to 9572 Waterway Passage in the highly sought-after community of Winter Garden! This beautifully move-in ready upgraded D.R. Horton Cresswell floor plan offers the perfect blend of modern style, comfort, and energy efficiency. From the moment you arrive, you'll appreciate the thoughtful enhancements that make this home truly stand out. Inside, laminate flooring flows seamlessly throughout the home, creating a clean, cohesive look with easy maintenance. A stunning geometric accent wall adds a designer touch to the loft and staircase, making a striking first impression. The spacious primary suite has been transformed into a luxurious retreat with a fully customized walk-in closet and a beautifully updated en suite bathroom. The guest bathroom has also been tastefully renovated with contemporary finishes. Step outside to your own private backyard oasis. Enjoy Florida living year-round with a sparkling pool and spa, a fully equipped outdoor kitchen, and built-in Bluetooth speakers—perfect for entertaining family and friends. Privacy bushes and low-maintenance artificial turf create a lush, secluded setting, while permanent exterior lighting enhances both curb appeal and year-round ambiance. Additional highlights include owned solar panels that help improve energy efficiency and reduce utility costs, making this home as practical as it is beautiful. Every detail has been carefully curated, offering move-in-ready luxury in one of Winter Garden's most desirable locations. Don't miss the opportunity to make this exceptional home your own!

9572 Waterway Passage Drive, Winter Garden

$465,000
3 Beds 3 Baths Emerald Ridge SubDv. 34787 Zip Code
*Walkthrough Video Available* Welcome to the gated Emerald Ridge neighborhood that is conveniently located near the 429, Turnpike, shopping and restaurants in Winter Garden, Horizon West and Windermere as well as the charming downtown Winter Garden Plant Street and all of the local activities it brings. Cool off in the COMMUNITY POOL and enjoy staying active on the sidewalks that run throughout the neighborhood. This home has an OPEN FLOOR PLAN that greets you as soon as you enter. The spacious living room has nice natural lighting and opens to the eat-in kitchen which was recently remodeled. You’ll find NEW CABINETRY with soft-close doors, a TILE BACKSPLASH and STAINLESS STEEL appliances. The WALK-IN PANTRY is a dream as it gives storage space for kitchen wares and laundry needs. Sliding doors open to the SCREENED PATIO so you can enjoy the evening breeze. There’s a SPACIOUS LOFT upstairs which makes for a fantastic 2nd living room, home office, play space, or home gym. The primary suite in this model is extra large giving room for a sitting area! The WALK-IN CLOSET offers plenty of space to keep your wardrobe organized and the en-suite bathroom has a garden tub and separate shower. The secondary bedrooms share a hall bathroom. The ROOF, AC, AND WATER HEATER WERE REPLACED IN 2018. Additional upgrades include CROWN MOLDING and canned lighting throughout the home.

1830 Morning Sky Drive, Winter Garden

$750,000
4 Beds 4 Baths Hamlin Reserve SubDv. 34787 Zip Code
Virtually Staged. CUSTOM, Like-New HOME with a large fenced-in yard in the heart of WinterGarden’s highly sought after Hamlin/Horizon West area. This home features the most desired floor plan built by the custom builder - Ashton Woods homes. It features 4 Bedrooms, 3.5 Baths, office, formal dining/flex space, 2 story impressive great room that you must see in person, a wrap-around full lanai with nice private backyard views. On the main level is the office with french doors, flex space/dining room, a Grand Gourmet Kitchen with butlers pantry that has every upgrade imaginable: custom cabinets, Stainless appliances, quartz counters, custom tile backsplash, whole home water filtration, and wood plank floors. The open layout kitchen with dine-in island flows into the expansive 2 story great room which has nice views of the expansive backyard. You can enjoy the perfect space to spend time with family and friends under the expanded, extended screened, wrap around Lanai with plenty of space to enjoy time with friends and family. Upstairs you’ll find the 3 secondary bedrooms and baths. The large primary suite features plenty of windows, dual vanities, a frameless glass shower with designer tile work, and large walk in closets. Other notable features include: large fenced yard, whole home water filtration, and more. Located in a highly desired community with resort style pool and splash pad, plenty of amenities, parks, walking trails, lakes and more. This sought-after Horizon West community is part of one of the fastest growing communities in the country with shopping, restaurants, movie theater, high rated schools, parks and a hospital all a short distance to the home. The community has easy access to FL-429, FL turnpike and Disney is only 15 minutes away! Downtown Orlando is 25 minutes so a quick commute to about anywhere you would want to go.

15372 Sugar Citrus Drive, Winter Garden

$739,000
4 Beds 4 Baths Waterleigh Ph 3b 3c & 3d SubDv. 34787 Zip Code
Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom home in the highly sought-after Winter Garden area! Perfectly positioned on a premium homesite, this home offers breathtaking water and conservation views with NO REAR NEIGHBORS, providing exceptional privacy and a peaceful backdrop. Designed for both comfort and functionality, the open floor plan features a private first-floor guest suite with a full bathroom, ideal for multigenerational living, overnight guests, or a home office. The spacious kitchen flows seamlessly into the dining and family room, creating the perfect setting for entertaining and everyday living. Upstairs, you’ll find a versatile loft that can serve as a media room, playroom, or second living area, along with the remaining bedrooms, including the spacious primary suite. Step outside to relax and unwind while enjoying the tranquil pond and conservation views from your backyard. Best of all, the HOA MAINTAINS the LAWN, allowing you to enjoy a low-maintenance lifestyle. Residents enjoy outstanding community amenities, including multiple resort-style swimming pools, a fully equipped fitness center with a play area, tennis courts, and more. Conveniently located near top-rated schools, shopping, dining, major highways, and Orlando’s world-famous attractions, this home offers the perfect blend of luxury, comfort, and convenience. Don’t miss this rare opportunity to own a home with stunning water and conservation views in one of Winter Garden’s most desirable communities!

9152 Sonoma Coast Drive, Winter Garden

$260,000
3 Beds 2 Baths Grove Resort And Spa Hotel Condominium SubDv. 34787 Zip Code
** WOW** A rare opportunity to purchase a 7th (top) floor condo at the beautiful Grove Resort and Water Park! This 3-bedroom, 2-bathroom, with sleeper sofa, comes fully furnished and ready to go! Onsite management does all the work for you by obtaining bookings through major websites and travel companies, and whenever you want to stay just let them know and you can stay in your unit for up to 179 nights per year. Everything you need is in the unit, full kitchen, washer and dryer, dishes, linens, TV's in all rooms, screened-in balcony, and gorgeous view over the pond and Lake Austin! The Grove Resort has three pools located at The Springs Pools area, where the large hot tub is also situated! Nearby is the full service Valencia restaurant, and the 24/7 gym. A short walk down to Lake Austin brings you to a fishing dock, and you can also rent a swan paddle boat, or kayak!! The Surfari Water Park is a must for owners and guests! A large pool is central to the amenity, and there is a lazy river, water slides, a splash zone, the Flowrider surfing experience, and you can enjoy a meal or beverage at the Longboard Bar and Grill! For added fun pay a visit to Flip Flops games arcade which has over 6000 sf of games and a black light mini golf course!! If you need snacks or quick essentials, the Marketplace has food, drinks, Starbucks, and gifts!! The concierge located at the front desk area sells all park tickets and can arrange transportation to all the theme parks!!! The Grove Resort is a Disney Good Neighbor Hotel, so transportation is FREE every day to the Disney theme parks also!! Don't miss this one!!****

14501 Grove Resort Avenue Unit 1728, Winter Garden

$729,000
4 Beds 4 Baths Waterleigh Ph 2b SubDv. 34787 Zip Code
Designed for comfortable everyday living and easy gatherings, this inviting Waterleigh home pairs a flexible two-story layout with fresh interior finishes and thoughtfully connected living spaces. Brand-new interior paint creates a bright, polished backdrop throughout, while decorative wainscoting and chair rail added in 2021 bring character to the main living areas. Just off the foyer, a versatile flex room can serve as a home office, formal dining room, playroom, hobby space, or additional sitting area based on your needs. Wood-look tile extends across the first floor, where wide archways create an easy flow between the kitchen, casual dining area, and family room. The kitchen is anchored by a large island with seating and features white cabinetry, stainless steel appliances, a blue glass-tile backsplash, generous counter space, a walk-in pantry, and a cabinet-lined serving area. The refrigerator was replaced in July 2024, and the microwave was replaced in November 2023. The first-floor primary suite offers a comfortable retreat with a tray ceiling, multiple windows, and an en suite bath featuring dual vanities, a soaking tub, separate shower, and an exceptionally large walk-in closet. Upstairs, one secondary bedroom includes its own full bath, while two additional bedrooms share another full bathroom with dual sinks. The oversized loft provides adaptable space for media, recreation, work, or hobbies. A dedicated laundry room, powder bath, built-in drop zone cabinetry, and attached two-car garage add everyday convenience. Wi-Fi-enabled features include the refrigerator, washer, dryer, microwave, thermostat, garage door openers, Ring device, and two smoke detectors. The exterior was painted in August 2025, and the covered front porch, covered rear lanai, and grassy backyard provide additional space to relax outdoors. Waterleigh residents have access to amenities throughout every phase of the community, including four resort-style pools, three fitness centers, tennis courts, sand volleyball, mini-golf, multiple playgrounds, pavilions, and walking paths. Lawn maintenance is included with the HOA, allowing more time to enjoy the neighborhood and its convenient Horizon West location near SR-429, shopping, dining, and Central Florida attractions.

9561 Waterway Passage Drive, Winter Garden

$600,000
4 Beds 4 Baths Encore/Ovation Ph 2 SubDv. 34787 Zip Code
Welcome to this beautifully appointed 4-bedroom, 3.5-bath home offering over 2,800 square feet of thoughtfully designed living space in the highly desirable Encore at Ovation community of Horizon West. Perfectly positioned on a premium corner lot, this home combines modern style, functional living, and an unbeatable location just 20 minutes from Walt Disney World. Step inside to discover gorgeous flooring throughout, a light and airy open-concept layout, and a timeless palette of neutral colors that complements any décor. The spacious kitchen flows seamlessly into the dining and living areas, creating an ideal space for entertaining and everyday living. A highly sought-after first-floor guest suite provides privacy and flexibility for visitors or multi-generational living. Upstairs, you'll find a generous loft with an open bannister, offering the perfect space for a media room, playroom, or home office. The conveniently located second-floor laundry room makes daily living effortless. The spacious primary suite serves as a relaxing retreat, while the additional bedrooms provide ample room for family and guests. Step outside to enjoy Florida living year-round on the screened-in lanai, ideal for morning coffee, outdoor dining, or unwinding in the evenings. Located in the sought-after Encore at Ovation community, this exceptional home offers easy access to major highways, top-rated schools, and Central Florida's world-famous attractions. With its desirable floor plan, stylish finishes, and prime Horizon West location, this home is one you won't want to miss.

13155 Spring Grove Way, Winter Garden

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