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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

$459,000
3 Beds 3 Baths Harvest/Ovation SubDv. 34787 Zip Code
***** PRICE REDUCED ***** Rare Dual Owner's Suite Townhome — Priced to Move, Near Disney This 3-bedroom, 3-bath, 1,808 sq ft Newton model townhome in Harvest at Ovation is one of the best values in the community right now. Built in 2024 and less than 2 years old, it shows like a model and is ready for immediate move-in, while comparable new construction in the area runs 7+ months out. What sets this home apart is its dual owner's suite layout, a rare find at this price point, with one suite offering a private balcony retreat overlooking the pond, with peaceful water views and nightly glimpses of Magic Kingdom fireworks. Step outside to your own covered patio, a comfortable outdoor living space perfect for everyday relaxation and entertaining. Upgraded flooring and fixtures run throughout, adding a polished, elevated feel without the premium price tag typically attached to that level of finish. Enjoy a community pool and playground, less than 10 minutes from Walt Disney World in one of Central Florida's fastest-growing corridors. With Winter Garden's shopping and dining nearby, this home offers exceptional value for buyers and investors who know the market. This home also includes a transferable 2-10 Pinnacle home warranty (active through May 2027) with zero service history, giving buyers added peace of mind on top of the builder's coverage. Priced competitively for a fast sale. Schedule your showing today.

14014 Scarlet Aster Alley, Winter Garden

$585,000
3 Beds 3 Baths Lakeshore Preserve Ph 1 SubDv. 34787 Zip Code
Stunning Luxury Townhome in Highly Sought-After Lakeshore Community! Welcome to this beautifully appointed 3-bedroom, 2.5-bath townhome offering a PRIVATE POOL (salt-water and heated), modern elegance, thoughtful design, and exceptional comfort in the heart of Horizon West. Located in the prestigious Lakeshore by Toll Brothers community, this residence showcases upscale finishes (Restoration Hardware fixtures), abundant natural light, and a spacious open-concept layout perfect for both everyday living and entertaining. Step inside to discover a bright and inviting living space, gourmet kitchen with premium cabinetry and top-of-the-line stainless-steel appliances, and a dining area that flows seamlessly to your private outdoor retreat. Upstairs, the luxurious owner’s suite features a spa-inspired bath with soaking tub, separate shower and generous customized walk-in closet, accompanied by two additional well-sized bedrooms and a stylish full bath. A convenient 2-car garage adds practicality and storage. Other features include whole house water filtration system, built-in speakers, custom woodwork, Haiku fans, upgraded sliding doors to patio with recently resealed pavers. Lakeshore offers resort-style amenities including a sparkling pool, clubhouse, fitness center, playgrounds, and scenic walking paths—plus you’re just minutes from top-rated schools, shopping, dining, Disney, and all the excitement of Hamlin and the Horizon West lifestyle. This is refined townhome living at its best—move-in ready and waiting for you. The HOA fee includes all amenities plus yard maintenance, exterior painting and pressure washing, roof replacement, irrigation water, 1 gig internet and basic cable.

8937 Lakeshore Pointe Drive, Winter Garden

$1,100,000
5 Beds 4 Baths Hickory Hammock Ph 1d SubDv. 34787 Zip Code
Welcome to this exceptional pool home in the highly sought-after gated community of Hickory Hammock in Winter Garden. Offering more than 3,600 square feet beautifully designed living space, this impressive five bedroom, four bathroom, 4 car garage residence blends timeless elegance with everyday functionality. From the moment you step inside, you'll be captivated by soaring ceilings, georgous formal dining space, elegant coffered and wainscoting details, custom built-ins, and an abundance of natural light. The open concept floor plan creates an effortless flow, making the home ideal for both intimate gatherings and grand entertaining. At the heart of the home, the gourmet kitchen overlooks the expansive living and dining areas, it features quartz counter tops, abundant cabinetry, generous prep space, and a layout designed for both entertaining and everyday living. A downstairs private home office offers a refined work from home setting, while the expansive upstairs loft is an entertainer's dream, complete with a projector and oversized movie screen, creating the perfect setting for cinematic experiences, game days, or a stylish media lounge. The luxurious primary suite serves as a peaceful retreat with a spacious walk-in closet and spa-inspired ensuite bath. Thoughtfully designed secondary bedrooms and bathrooms provide comfort and privacy for family and guests. Step outside to your own private outdoor oasis where a screened resort-style pool and covered lanai create the ultimate setting for year-round Florida living. Whether hosting guests or enjoying a quiet evening at home, this backyard is designed for relaxation and entertaining. Recent enhancements that showcase true pride of ownership, including a freshly repainted interior, whole home pressure washing, new landscape, and a professionally serviced and cleaned air conditioning system. Residents of the gated community of Hickory Hammock enjoy an exceptional lifestyle with resort-style amenities including a clubhouse, fitness center, community pool, playgrounds, dog park, scenic walking trails, fishing pier, and boat ramp access to the beauty of Johns Lake. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, top rated schools, shopping, dining, SR 429, Walt Disney World, and Orlando's world class attractions, this remarkable home offers the perfect balance of luxury, lifestyle, and convenience. Schedule your showing today!

16044 Citrus Knoll Drive, Winter Garden

$1,195,000
5 Beds 4 Baths Oakland Park Unit 1b-1b SubDv. 34787 Zip Code
Virtually Staged. More than a home, this is a lifestyle. Perfectly positioned in the highly sought-after Oakland Park community, this exceptional residence combines timeless design, generous living spaces, and effortless indoor-outdoor living just a golf cart ride from the heart of downtown Winter Garden. With 5 large bedrooms plus a den spread across over 3,500 square feet, the home provides ample space for everyday living and entertaining. Upon arrival, a welcoming front porch sets the tone, offering the perfect place to enjoy a quiet morning coffee or unwind with a glass of wine at sunset. Inside, elegant French doors open to a private home office, while engineered hardwood flooring flows throughout the main living areas. The open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. At the heart of the home, the spacious kitchen overlooks the living area and seamlessly connects to the expansive screened lanai through double French doors. The first-floor primary suite is a private retreat, highlighted by a tray ceiling and a spa-inspired bath featuring dual vanities, a soaking tub, a separate walk-in shower, and an oversized walk-in closet. A secondary bedroom and full bath on the main level provide ideal accommodations for guests or multigenerational living. Upstairs, a spacious loft offers endless possibilities as a media room, game room, or additional gathering space. Three generously sized secondary bedrooms—each with its own walk-in closet—along with two full bathrooms provide comfort and privacy for family and guests alike. Step outside to one of the home's most impressive features: an expansive screened lanai overlooking a fully fenced backyard with ample room to design the pool of your dreams. Completing the property is a coveted three-car garage, offering abundant space for vehicles, storage, and recreation. Residents of Oakland Park enjoy a picturesque, tree-lined community known for its welcoming atmosphere, resort-style amenities, seasonal community events and unmatched location. Just minutes from the award-winning shops, restaurants, farmers market, and West Orange Trail in historic downtown Winter Garden, this home offers the perfect balance of luxury, convenience, and the quintessential Central Florida lifestyle.

844 Oakland Park Boulevard, Winter Garden

$395,000
3 Beds 3 Baths Waterleigh Ph 4a SubDv. 34787 Zip Code
Welcome to the highly sought-after Waterleigh community in Winter Garden, where resort-style living meets everyday convenience! This beautiful Dr. Horton Ibis Model offers 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed two-story layout in a desirable middle-unit townhome. Step inside to an open-concept floor plan featuring a spacious kitchen with granite countertops, ample cabinetry, and all appliances included—making this home truly move-in ready. The washer and dryer are conveniently located on the second floor alongside all three bedrooms, adding ease to your daily routine. Enjoy peace of mind with an air conditioning system and hot water heater that are only 1.5 years old. Outside, a paver driveway leads to the attached one-car garage, providing both curb appeal and functionality. Living in Waterleigh means enjoying exceptional community amenities, including three resort-style pools, a state-of-the-art fitness center, tennis courts, sand volleyball, scenic walking trails, playgrounds, and beautifully maintained green spaces. The HOA takes care of lawn maintenance and mulch, allowing you to spend more time enjoying everything this incredible community. Ideally located near top-rated schools, shopping, dining, major highways, and all that Winter Garden has to enjoy, this home is the perfect combination of comfort, convenience, and Florida living. Don't miss your opportunity to own in one of Central Florida's most desirable master-planned communities!

13158 Bounty Avenue, Winter Garden

$380,000
3 Beds 3 Baths Watermark Ph 3 SubDv. 34787 Zip Code
Discover refined, low-maintenance living in this impeccably cared-for townhome located in the sought-after Watermark community of Horizon West. Built by Meritage Homes in 2018 with a focus on energy efficiency, this residence combines comfort, style, and everyday functionality. The main level showcases an open-concept layout with elegant tile flooring throughout, leading into a well-appointed kitchen designed for both daily living and entertaining. Highlights include 42-inch cabinetry with crown molding, polished granite countertops, and a spacious walk-in pantry. Step outside to a private brick-paver lanai, along with access to a detached two-car garage. Upstairs, you’ll find all three bedrooms, including a peaceful primary suite featuring dual granite vanities and a generous walk-in closet. The secondary bedrooms are equally well-sized, sharing a full bathroom with granite finishes. An upstairs laundry room—with washer and dryer included—adds extra convenience. This home is complete with all essential appliances. Living in the Watermark community means enjoying an array of resort-style amenities such as a pool, spa, fitness center, tennis courts, splash pad, playground, picnic areas, and a beautifully appointed clubhouse ideal for gatherings. Conveniently located near top-rated schools, Hamlin Town Center, Walt Disney World, and major roadways including 429, 408, 192, and the Turnpike, this home offers a lifestyle. Don’t miss the opportunity to enjoy everything Florida living has to offer in this vibrant and amenity-rich community. Property is tenant occupied. Showings by appointment only. Listing Agent can provide a video tour of the property upon request.

14031 Picard Alley, Winter Garden

$2,615,320
6 Beds 7 Baths Grove/Oakland SubDv. 34787 Zip Code
Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the exclusive, boutique enclave of The Grove at the Harvest District in the charming Town of Oakland, Florida. Spanning an impressive 4,658 square feet, this stunning residence offers six generously sized bedrooms, each with its own private ensuite bath, delivering the ultimate in comfort and privacy for family and guests alike. A dedicated home office provides the perfect retreat for focused work, while the airy upper-level loft adds flexible living space ideal for a media room, playroom, or secondary lounge. Step outside and experience true Florida luxury a custom pool serves as the centerpiece of the outdoor living area, perfectly positioned to capture serene pond views that make every morning and evening feel like a private escape. Seamless indoor-outdoor integration defines this home's design philosophy, with expansive windows flooding the interior with natural light and blurring the line between inside and out. Inside, Davila Homes' signature craftsmanship is evident at every turn: timeless architecture, high-end finishes, an open-concept layout designed for effortless entertaining, and a gourmet kitchen appointed with state-of-the-art appliances. Every detail was thoughtfully curated and personalized through Davila's exclusive Design Center experience. The Grove is one of Oakland's most intimate and sought-after communities, featuring just 44 homesites surrounded by lush common areas, water features, walking trails, and bike paths. Minutes from the vibrant shops and dining of Downtown Winter Garden, top-rated West Orange County schools, and the beloved West Orange Trail, yet tucked away in the quiet charm of one of Central Florida's most historic small towns.

1152 Prado Lane, Oakland

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