Winter Garden Homes with Pool Community Features

Winter Garden Homes with Pool Community Features

Welcome to Winter Garden, a charming city located in Orange County, Florida. Known for its historic downtown area, Winter Garden offers a mix of small-town charm and modern amenities. Residents enjoy a thriving community with a variety of shops, restaurants, and entertainment options.

If you're looking for homes with pool community features in Winter Garden, you're in luck. Many neighborhoods in Winter Garden offer this desirable amenity, allowing residents to enjoy the Florida sunshine and stay cool during the hot summer months. Whether you're looking for a single-family home with a private pool or a community pool where you can socialize with neighbors, Winter Garden has options to suit your needs.

Living in a home with pool community features not only provides a great way to relax and stay active but also creates opportunities to meet new people and build lasting relationships within the neighborhood. If you're considering making Winter Garden your home, be sure to explore the various communities that offer homes with pool amenities to find the perfect fit for your lifestyle.

Newest Winter Garden Homes with Pool Community Features

14501 Grove Resort Avenue Unit 3420, Winter Garden
$169,900
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
This stunning 2-bedroom, 2-bathroom condo-hotel in Orlando, Florida, offers the perfect blend of luxury, comfort, and convenience. Located just minutes from the world-famous theme parks, this fully furnished unit is an excellent choice for both personal use and investment. The condo features a spacious open floor plan with modern finishes, a fully equipped kitchen with stainless steel appliances, and a private balcony with breathtaking views. The master suite boasts a luxurious en-suite bathroom, while the second bedroom and bath provide ample space for guests. Enjoy resort-style amenities, including a sparkling swimming pool, fitness center, full-service spa, on-site dining, concierge services, and a shuttle to major attractions. With its prime location near shopping, dining, and entertainment, this condo-hotel is an exceptional opportunity for those looking to experience the best of Orlando!

14501 Grove Resort Avenue Unit 3420, Winter Garden
231 Tbd Drive, Winter Garden
$973,550
5 Beds ⋅ 5 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Discover the Griffin by Toll Brothers at Westhaven at Ovation in Winter Garden, with estimated completion by the end of 2027! This beautifully designed home features an impressive foyer, formal dining room, and spacious kitchen overlooking the breakfast area and great room. The great room opens to a covered lanai, creating the perfect space for everyday living and entertaining. Upstairs, the primary suite offers a large walk-in closet and a private bath with a separate shower and private water closet. A spacious loft and generously sized secondary bedrooms provide additional flexibility. Experience the quality craftsmanship and thoughtful design of Toll Brothers. Model home available for walkthrough!

231 Tbd Drive, Winter Garden
233 Tbd Drive, Winter Garden
$867,555
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Winter Garden's Horizon West, with estimated completion by the end of 2027! Welcome home to this beautifully designed open-concept residence featuring a sought-after first-floor primary suite. The light-filled two-story foyer creates an impressive first impression and flows seamlessly into spacious living and entertaining areas. Thoughtfully designed with generous room sizes and abundant natural light, this home offers the perfect blend of comfort, style, and functionality for everyday living and entertaining.

233 Tbd Drive, Winter Garden
13011 Sunset Garden Lane, Winter Garden
$1,034,940
5 Beds ⋅ 5 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Discover the Griffin by Toll Brothers at Westhaven at Ovation in Winter Garden! This beautifully designed home features an impressive foyer, formal dining room, and spacious kitchen overlooking the breakfast area and great room. The great room opens to a covered lanai, creating the perfect space for everyday living and entertaining. Upstairs, the primary suite offers a large walk-in closet and a private bath with a separate shower and private water closet. A spacious loft and generously sized secondary bedrooms provide additional flexibility. Experience the quality craftsmanship and thoughtful design of Toll Brothers. Model home available for walkthrough!

13011 Sunset Garden Lane, Winter Garden
15126 Flannan Lane, Winter Garden
$534,170
3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to the Kelly bungalow by Toll Brothers at Westhaven at Ovation in Winter Garden! This thoughtfully designed home offers an inviting open-concept layout with a spacious great room, beautifully appointed kitchen, and dining area perfect for everyday living and entertaining. The private primary suite provides a relaxing retreat, while additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the charm of bungalow living with the quality craftsmanship and modern design Toll Brothers is known for. Conveniently located near shopping, dining, entertainment, and major roadways in desirable Horizon West.

15126 Flannan Lane, Winter Garden
15162 Flannan Street, Winter Garden
$702,570
5 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Winter Garden's Horizon West. Estimated completion Summer 2027. The Montpelier Bungalow features a covered entry leading to a spacious foyer and an expansive guest suite. The main living area offers a dining room, breakfast bar, great room, and access to the private courtyard. The second-floor features two bedrooms and a spacious primary suite with a large walk-in closet and private bath featuring dual vanities, a separate shower, and private water closet. An additional bedroom, loft, and full bathroom are located above the detached garage, offering flexible space for guests or family.

15162 Flannan Street, Winter Garden
12822 Sunset Walk Drive, Winter Garden
$528,396
3 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to the Crowley townhome by Toll Brothers in the desirable Winter Garden/Horizon West area. This beautifully designed home features an open-concept layout connecting the great room, kitchen, and dining area. Enjoy outdoor living in the private courtyard with direct access to the detached 2-car garage. The spacious primary suite offers a large walk-in closet and a well-appointed bathroom with dual vanities and a separate shower. Experience stylish, low-maintenance living in one of Central Florida’s most desirable locations.

12822 Sunset Walk Drive, Winter Garden
12826 Sunset Walk Drive, Winter Garden
$539,239
4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Horizon West with estimated completion in early 2027! This beautiful townhome features 4 bedrooms and 3 full bathrooms, including a first-floor bedroom and full bath, plus 3 bedrooms and 2 bathrooms on the second level. Enjoy an open-concept kitchen, dining area, and spacious great room with access to a private courtyard. The primary suite offers a large walk-in closet and a private bath with dual vanities and a separate shower. Conveniently located near shopping, dining, top-rated schools, and major roadways. Don't miss this opportunity!

12826 Sunset Walk Drive, Winter Garden
1076 Sadler Oaks Way, Oakland
$1,570,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
*** A RARE Offering in Oakland Park | Custom-Built Luxury | ONE-STORY Living *** An exceptional opportunity to own a custom-built residence in the highly sought-after community of Oakland Park, where timeless architectural details, refined finishes, and an extraordinary setting come together. This beautifully appointed 4 bedroom, 3.5 bath home with mudroom and OVERSIZED garage (2.5), with more than 700 square feet of space, offers a highly desirable feature rarely found in Oakland Park: a thoughtfully designed, single-story floor plan with TWO spacious PRIMARY suites. Situated on a premium corner lot, nearly a QUARTER acre, the property enjoys an exceptional sense of privacy, with mature oak trees, no rear neighbors, and a neighboring park, providing additional open space and lasting privacy. Inside, soaring vaulted ceilings, stunning WOOD flooring, elegant crown molding, a cozy FIREPLACE, and an impressive collection of custom millwork, including shiplap accents and exposed timber details, establish a warm yet sophisticated aesthetic appearance. The heart of the home is an expansive, open-concept kitchen and great room designed for both everyday living and effortless entertaining. The beautifully appointed kitchen features custom-panel THERMADOR appliances, including a 6 burner GAS cooktop, built-in oven and microwave, a walk-in pantry, and a coffee bar conveniently connected to the formal dining room. A charming breakfast nook completes this exceptional gathering space. One of the home’s most distinctive features is the expansive screened-in courtyard, creating a seamless extension of the indoor living areas. Finished with elegant travertine pavers, this private outdoor retreat features a kitchen complete with a grill and sink, making it ideal for entertaining or simply enjoying the Florida lifestyle. The generous courtyard also presents an exciting opportunity for a future swimming POOL, allowing the next owner to further customize the space. A separate covered rear porch and welcoming front porch provide additional opportunities to enjoy the home’s beautiful surroundings. The primary suite toward the back of the home includes a comfortable sitting area and an oversized eight-foot sliding glass door opening directly to the courtyard. The luxurious en-suite bath offers a quartz-topped vanity, walk-in shower, and garden tub. The second primary suite features an adjacent full bath and its own courtyard access, ideal for multigenerational living, visiting guests, or an extended-stay retreat. Two additional bedrooms with walk-in closets are towards the back of the home along with a full bath. A conveniently located half bath serves the main living areas and has access to the courtyard. The home is a short GOLF-CART ride to Historic Downtown Winter Garden's award-winning restaurants, shopping, farmers market, and events. This golf-cart-friendly waterfront community offers two pools (one resort styled pool), a clubhouse, parks, playgrounds, dog park, lake-side walking trails, and access to the 22-mile West Orange Trail, with easy reach to interstate travels, golf, and world-renowned theme parks. More than a home, it is the Winter Garden lifestyle. A rare combination of one story custom craftsmanship, privacy, exceptional outdoor living, and an irreplaceable location along the West Orange Trail, this remarkable Oakland Park residence offers a lifestyle that is increasingly hard to find.

1076 Sadler Oaks Way, Oakland
12818 Sunset Walk Drive, Winter Garden
$659,008
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Horizon West with estimated completion in early 2027! This unique townhome features 4 bedrooms and 3 full bathrooms, including a first-floor bedroom and full bath, plus 3 bedrooms and 2 bathrooms on the second level. A private loft and full bathroom above the detached garage provide additional flexible living space, perfect for guests, multigenerational living, or a home office. Enjoy an open-concept kitchen, dining area, and great room with access to a private courtyard. Conveniently located near shopping, dining, top-rated schools, and major roadways. Don't miss this unique opportunity!

12818 Sunset Walk Drive, Winter Garden
12834 Sunset Walk Drive, Winter Garden
$636,947
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction – Estimated Completion Early 2027! Welcome to the beautiful Autumn townhome, offering 2,447 square feet, 4 bedrooms, 4 bathrooms, and a versatile flex room and loft. The open concept main living area features a spacious kitchen with designer backsplash, modern cabinetry, and upgraded countertops, flowing seamlessly into the great room and casual dining area. Upstairs, the private primary suite includes a spacious walk-in closet, along with two additional bedrooms. A fourth bedroom and full bathroom are located on the first floor along with a loft and bathroom above the detached two-car garage. This provides additional flexibility and privacy. Enjoy a private rear courtyard and future resort-style community amenities. Closing cost assistance available! Schedule your appointment today!

12834 Sunset Walk Drive, Winter Garden
14501 Grove Resort Avenue Unit 1516, Winter Garden
$283,800
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
GREAT NEW LISTING: PRICE $283,800.00. MOTIVATED SELLER. WELCOME TO THE GROVE RESORT & WATERPARK, A CONDO HOTEL LOCATED CLOSE TO DISNEY AND ALL THE ORLANDO ATTRACTIONS. THIS BEAUTIFUL LUXURY FULLY FURNISHED 3 BEDROOM/2 BATHROOM JASMINE DESIGN CONDO HAS GREAT WATER VIEWS FROM THE SCREENED BALCONY ON THE 5TH FLOOR. YOU CAN OWN A BEAUTIFUL VACATION CONDO AT THE GROVE RESORT THAT OFFERS PROFESSIONAL ON SITE PROPERTY MANAGEMENT SERVICES TO OWNERS AND THEIR GUESTS. THE GROVE RESORT HAS MANY AMENITIES INCLUDING: WATERPARK, LAZY RIVER, SWIMMING POOLS, WATER SLIDES, SPA, INDOOR & OUTDOOR DINING, FITNESS CENTER, LAKE AUSTIN FOR FISHING AND PADDLE BOATING, SHOPPING AND MUCH MORE.

14501 Grove Resort Avenue Unit 1516, Winter Garden
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