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Homes for Sale with a Pool in Winter Garden, FL

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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

3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 2 SubDv. ⋅ 34787 Zip Code

Escape to your own luxurious, fully furnished condo-hotel residence at the prestigious Grove Resort & Water Park—just minutes from Walt Disney World. Designed for both personal enjoyment and investment, this exceptional unit offers the perfect combination of a turnkey vacation retreat and high-performing income asset. Located on the third floor of Condominium II, the sought-after Jasmine floor plan boasts an open-concept living area filled with natural light, a modern kitchen with stainless steel appliances, sleek countertops, and the convenience of in-unit laundry. Step out onto the extended screened balcony to enjoy tranquil resort and conservation views—an ideal space for morning coffee or evening relaxation. As an owner, you and your guests will experience resort living at its finest. The Surfari Water Park features a thrilling lazy river, water slides, and the FlowRider surf simulator. Multiple heated pools, hot tubs, and private cabanas create endless opportunities for relaxation, while children will love the splash zones, game arcade, and dedicated play areas. Beyond the water attractions, the resort offers on-site restaurants and bars, a grocery café, full-service spa, fitness center, mini-golf, boat rentals, and 24-hour concierge services—all within a secure, award-winning community. This unit is part of the professionally managed hotel rental program, offering truly hands-free ownership. With full-service management covering marketing, bookings, housekeeping, and maintenance, owners can enjoy strong cash-flow potential while eliminating the stress of day-to-day operations. Whether you’re looking for a private getaway near Orlando’s top attractions or a proven income-producing property, this Grove Resort condo presents an unmatched opportunity. Experience luxury, convenience, and investment potential in one of Central Florida’s premier resort communities. Schedule your private tour today!

14501 Grove Resort Avenue Unit 2334, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code

Welcome to Your Perfect Orlando Investment & Vacation Escape! This beautifully appointed condo-hotel unit offers the ideal combination of investment potential and vacation paradise. Featuring 3 spacious bedrooms, 2 modern bathrooms, and 1,396 sq. ft. of living space, this residence provides plenty of room for relaxation and entertainment—all with a picturesque fountain view. Enjoy gourmet meals at the Valencia Restaurant or satisfy your sweet tooth at the on-site coffee shop and ice cream parlor. Stay active in the state-of-the-art fitness center or unwind with rejuvenating spa treatments. Challenge friends in the game room, enjoy mini-golf, or dive into hours of arcade fun. Make the most of two sparkling pools complete with a waterpark, lazy river, splash zone, and poolside bar & grill. Perfectly located near Orlando’s world-famous attractions, this property is designed for both vacation enjoyment and lucrative investment returns. Whether you’re relaxing by the fountain, exploring the city, or maximizing rental income, this condo-hotel offers the best of both worlds. Own your slice of Orlando paradise today!

14501 Grove Resort Avenue Unit 3202, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code

Stunning Emerald serie house, Selden model built in 2018 well maintained, featuring 4 bedrooms, 3.5 bathrooms, and approximately 2,920 sq ft of living space. Situated on a premium corner lot of about 10,585 sq ft, this home offers a 3-car tandem garage, spacious backyard, private wooded views, and a screen-enclosed private pool—perfect for year-round Florida living. The open-concept design includes a formal dining room, elegant foyer with wrought-iron staircase, and a gourmet kitchen with a large island, 42” cabinets with crown molding, granite countertops, stainless steel appliances, and a convenient drop zone from the garage. The owner’s suite boasts a tray ceiling, a spa-like en-suite bathroom with dual sinks, a garden tub, and a spacious walk-in closet. Additional features include a durable concrete tile roof, dual A/C units, and numerous upgrades: exterior lighting, sealed paver driveway and porch, landscape lighting, decorative stonework, epoxy-finished garage floor, and professional landscaping. Lawn care is included with HOA fee. Located in the highly sought-after Waterleigh community in Winter Garden, residents enjoy resort-style amenities: two community clubhouses, 4 resort-style pools, 2 fitness center, beach volleyball, 2 tennis courts, mini-golf, community garden, dog park, fishing pier, and scenic walking/biking trails. The neighborhood is beautifully landscaped with lakes, green spaces, and planned community events. Conveniently located just minutes from Historic Downtown Winter Garden, Winter Garden Village, and easy access to SR-429 for a quick commute to Orlando and Walt Disney World. Zoned for top-rated schools: Atwater bay Elementary, Water Spring Middle, and Horizon High School.

10007 Little Alcove Loop, Winter Garden

Briley Farm SubDv. ⋅ 34787 Zip Code

Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room—airy yet cozy and ready for your personal touch. Enjoy the perfect balance of indoor and outdoor living, set against serene scenery while remaining close to shopping, restaurants, and major highways. Briley Farm offers comfortable countryside living under a canopy of welcoming trees, crafted to embody the lifestyle you’ve been searching for. Stop by our sales office today to start building your dream home with Pioneer Builders!

514 N Pollard Street, Oakland

4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code

A home full of charm, comfort, and practicality. It features four bedrooms, including a spacious master suite, three full bathrooms, and a powder room, distributed in a clever layout that enhances each room. Right at the entrance, the balcony invites you to slow down and enjoy the home's cozy atmosphere. The kitchen is modern and functional, equipped with all essential appliances and a central island perfect for quick meals or family time. The laundry room is also fully equipped and ready for everyday use. Upstairs, a spacious loft opens up to new possibilities—it could be a TV room, office, or leisure space—in addition to three bright and comfortable bedrooms. Sliding doors connect the interior area with the private backyard, where the covered balcony offers stunning views. With no neighbors in the back, the environment is quiet, private, and ideal for relaxation. The condominium offers a complete infrastructure, with swimming pools, gyms, and leisure areas for the whole family. The location is strategic, with supermarkets, schools, and various amenities nearby, as well as easy access to the region's main attractions. The house is currently occupied, but you can schedule a viewing. A rare opportunity to live well, with tranquility and quality of life.

17865 Adrift Road, Winter Garden

5 Beds ⋅ 6 Baths ⋅ 34787 Zip Code

Pre-Construction. To be built. To be Built, Rendering provided by master custom home builder, David Konkol of Konkol Custom Homes. However, buyer can work with builder to build any design buyer prefers (pricing to adjust accordingly). The property is spectacular waterfront acreage with boat dock on boatable, skiable Lake Roper. Acreage is 12.4 +/- with some conservation. Zoned A-1 (agricultural zoning designation). Very quiet. Very private. No HOA and close to Winter Garden and Windermere amenities as well as all theme parks.

13377 Lake Butler Boulevard, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Watermark Ph 2c SubDv. ⋅ 34787 Zip Code

Short Sale. BACK ON THE MARKET — THROUGH NO FAULT OF THE SELLER! Buyer financing fell through. Welcome Home! 14536 Golden Harbor – a beautifully designed 3-bedroom, 2.5-bathroom home offering 1,904 square feet of thoughtfully laid-out living space. Nestled on the desirable Watermark community on the Disney side of Winter Garden, this Meritage Angelou II model combines modern efficiency with everyday comfort. The home comes equipped with fully PAID OFF solar panels, already wired and ready for connection—making this an energy-smart choice for eco-conscious buyers. As you walk in you are greeted with open-concept living/ dining room area that is ideal for entertaining, with a spacious kitchen located at the rear of the home. Enjoy stainless steel appliances, crown-topped cabinetry, a walk-in pantry, and a generous granite island that flows seamlessly into the living and dining areas. You’ll also find a built-in office nook and a convenient half-bath on this level. Upstairs, a spacious loft adds flexibility—perfect as a second living area, playroom, or home office. The laundry area is thoughtfully tucked away, and the split-bedroom design offers added privacy. The primary suite includes a walk-in closet, dual vanity, and a walk-in shower. Two additional bedrooms are located toward the front of the home and extend access to a private, covered balcony—an ideal spot to catch Disney’s nightly fireworks with a glass of wine and a great book. Whether you're unwinding on the front porch, enjoying balcony views, or taking advantage of community amenities—including a resort-style pool, playground, fitness center, basketball court, and more—you’ll find the lifestyle here hard to beat. You are just walking distance to The Mark, a versatile retail neighborhood center, with stores, restaurants, gas station, and more! Best of all, you’re just minutes from Walt Disney World, Magic Kingdom, Epcot, and Hollywood Studios—each less than 20 minutes away.

14536 Golden Harbor Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamilton Gardens Ph 2a & 2b SubDv. ⋅ 34787 Zip Code

Welcome to 5963 Glory Bower Drive, Winter Garden, FLorida a beautifully Home 3 bedroom, 2.5 bathrooms, plus office space, offering over 2,120 square feet of thoughtfully designed living space. This modern residence features an open-concept layout perfect for both everyday living and entertaining. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, ample cabinetry, and a gas range. The home also features a gas water heater, providing efficiency and convenience. One of the standout features of this home is the solar panel system, providing incredible energy efficiency and keeping the average monthly electric bill at just $33. Enjoy the Florida lifestyle just minutes from Disney.

5963 Glory Bower Drive, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code

HUGE PRICE REDUCTION! Welcome to your fully furnished, turn-key 2-bedroom, 2-bath retreat at the Grove Resort & Water Park—just minutes from Disney! Whether you’re searching for the perfect vacation getaway or a smart investment property, this unit has it all. From your private balcony, enjoy peaceful conservation views while knowing your condo is working for you when you’re away. With a strong rental history and enrollment in the resort’s professionally managed short-term rental program, generating income couldn’t be easier. Enjoy the Surfari Water Park, multiple pools, spa, fitness center, restaurants, lakefront pier, and more—everything you and your guests need for a memorable stay. Don’t wait—units like this move quickly! Showings are by appointment only, as this condo is a guest favorite and often booked.

14501 Grove Resort Avenue Unit 3714, Winter Garden

1 Beds ⋅ 1 Baths ⋅ Grove Res & Spa Hotel Condo Iv SubDv. ⋅ 34787 Zip Code

Experience Orlando from a fresh perspective in this refined one-bedroom, one-bath condominium suite set inside, The Terraces at The Grove Resort & Waterpark, just minutes from Walt Disney World®. Nestled on a quiet rise above shimmering Lake Austin, the residence blends boutique-hotel with the comforts of a private retreat. Wake each morning to calming waterfront views, then step into interiors styled with crisp lines, contemporary finishes, and floor-to-ceiling glass that invites the Florida sunshine in. Owners enjoy full privileges at The Grove, including the thrilling Surfing Water Park with its wave pool and surf simulator, yet The Terraces preserves an upscale, adult-oriented ambiance all its own. Exclusive resident perks include: Secluded infinity pool reserved for Terraces guests only, Poolside bar for craft cocktails and light bites, State-of-the-art fitness studio that keeps wellness on track, Byte market for convenient grab-and-go meals and lounge, an intimate space to unwind with friends after a day of adventure Beyond the resort gates, world-class shopping, dining, and Orlando’s famed theme parks are a quick drive away placing endless entertainment at your doorstep while safeguarding the serenity of home. Whether you’re seeking a wonderful vacation rental or a personal escape from everyday routine, this condominium delivers a rare blend of luxury, location, and lifestyle. Secure your slice of paradise before someone else claims the view.

15695 Grove Resort Avenue Unit 4303, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel SubDv. ⋅ 34787 Zip Code

HUGE PRICE REDUCTION! Don’t miss this rare opportunity to own a fully furnished, turn-key 3-bedroom, 2-bath resort condo at the world-famous Grove Resort & Water Park, just minutes from Disney. Located in Building 2, Unit #2129 offers tranquil conservation views from your private balcony and quick access to the resort’s incredible amenities. Whether you’re seeking a personal vacation retreat or a hands-free income-producing property, this condo delivers both. With a proven rental history and participation in the professionally managed short-term rental program, you can generate income seamlessly when you’re not here. Guests can enjoy the Surfari Water Park, multiple pools, spa, fitness center, restaurants, lakefront pier, and more—completely worry-free. Act quickly—this unit is a guest favorite, showings are limited, and opportunities like this don’t last.

14501 Grove Resort Avenue Unit 2129, Winter Garden

4 Beds ⋅ 5 Baths ⋅ 34787 Zip Code

Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with approximately 844 linear feet of lakefront property on Lake Roper. Home could also be built as a multigen and could be larger if needed with ample room for multiple garage spaces as well. This is a RARE OPPORTUNITY to acquire this much lakefront property and land but be in close proximity to city center, major thoroughfares, restaurants, theme parks, international airports. Value is in the land -- get a free house!

13377 Lake Butler Boulevard, Winter Garden

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