Winter Garden Homes with Pool Community Features

Winter Garden Homes with Pool Community Features

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County, where Southern hospitality meets modern living. Known for its picturesque landscapes, vibrant downtown area, and rich history, Winter Garden has become a sought-after destination for families and individuals alike. With its lush parks, scenic trails, and proximity to the stunning Lake Apopka, outdoor enthusiasts will find endless opportunities for recreation.

One of the standout features of Winter Garden is its diverse selection of homes, particularly those nestled within communities that boast private pools. Imagine coming home to your own oasis, where you can unwind after a long day or host lively gatherings with friends and family. These homes with pool community features provide a perfect blend of relaxation and entertainment, making them ideal for enjoying Florida's warm climate year-round.

The allure of Winter Garden extends beyond its beautiful homes. The city is home to a thriving downtown district, filled with charming boutiques, delightful cafes, and a variety of dining options that cater to every palate. The historic Garden Theatre offers a glimpse into the city’s cultural scene, showcasing local talent and providing a hub for the arts.

With excellent schools, family-friendly events, and a strong sense of community, Winter Garden is the perfect place to call home. Whether you're looking for a tranquil retreat or an active lifestyle, the homes with pool community features in this idyllic city offer the best of both worlds. Discover your dream home in Winter Garden and embrace the enchanting Florida lifestyle!

Newest Winter Garden Homes with Pool Community Features

4 Beds ⋅ 4 Baths ⋅ O6435581 MLS

Welcome to 17336 Lake Star Road, a beautifully appointed 2024-built pool residence framed by unobstructed conservation views at both the front and rear. Featuring Ashton Woods’ highly desirable Griffin floor plan, this move-in-ready home includes thoughtful upgrades throughout, a fenced backyard and exceptional privacy with no immediate neighbors directly in front or behind. Abundant windows throughout the home fill the interiors with natural light while capturing peaceful views of the surrounding greenery and natural setting from nearly every room. A dedicated butler’s pantry adds both functionality and an elegant transition between the kitchen and dining spaces. Among a limited selection of 2024-built residences currently offered for sale in Winter Garden with a private pool, the home also benefits from notably low HOA fees and no CDD. For buyers seeking a seamless move-in experience, designer furniture and furnishings are also available as a separate package, offering the opportunity to enjoy the home beautifully furnished from day one. Ideally situated in Ovation at Horizon West and near top-rated schools, the property combines newer construction and peaceful conservation surroundings with easy access to Central Florida’s most desirable destinations. Walt Disney World Resort is approximately 5 miles away, with direct access via SR 429 and Western Way, while Universal Orlando is approximately 25 miles away. Publix, Starbucks and Target are just minutes away, along with an excellent selection of nearby dining, shopping, entertainment and everyday essentials. Schedule a private showing to experience the conservation views, natural light, and privacy of this Northlake at Ovation residence firsthand.

17336 Lake Star Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6441092 MLS

Located in the desirable Winding Bay community in Horizon West, this impeccably maintained home offers 3 spacious bedrooms, 2.5 bathrooms and a versatile flex room that can easily serve as a home office, playroom or potential 4th bedroom. Luxury tile flooring, upgraded in 2025, flows throughout the entire home for a clean and consistent look that is stylish, durable and easy to maintain. The kitchen serves as the centerpiece of the main living space, featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, hard-wired under-cabinet lighting and abundant counter and storage space. Crown molding, oversized baseboards, decorative columns, and custom finishes bring an elevated feel and distinctive detail to the interior. The spacious owner’s suite features plantation shutters and a beautiful en-suite bathroom, fully upgraded in 2026 with floor-to-ceiling tile, modern finishes and a large walk-in closet. The two secondary bedrooms share a convenient Jack-and-Jill bathroom. Double sliding doors lead to the screened lanai with sun shades, overlooking the fully fenced backyard with iron fencing. In the evening, relax outdoors and enjoy views of the Disney fireworks in the distance, adding a special touch to the Florida lifestyle. Additional features include an extended driveway with pavers, gutters, whole-home security camera system, whole-home water softener, reverse osmosis filtration in the kitchen and a dedicated garage outlet for an additional refrigerator or freezer. Solar panels provide an added energy-efficiency benefit, with electric bills averaging approximately $34 during the hot summer months. With no carpet, extensive upgraded tile flooring, flexible living space, a renovated owner’s bathroom, solar panels, and numerous thoughtful upgrades, this Horizon West home is truly move-in ready. This home offers convenient access to shopping, dining, schools, major roadways, and the many amenities throughout Winter Garden and West Orange County. Schedule your showing today!

10750 Petrillo Way, Winter Garden

2 Beds ⋅ 3 Baths ⋅ O6440912 MLS ⋅ 26 BLDG.

Welcome to this beautifully maintained 2 bedroom, 2 bath townhome in the highly sought-after Independence community at Signature Lakes. This home offers a bright, open layout with comfortable living spaces perfect for both everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, creating a welcoming atmosphere filled with natural light. Both bedrooms are generously sized, offering privacy and flexibility for guests, a home office, or a cozy retreat. The attached 2-car garage provides secure parking and additional storage—an added convenience rarely found in townhome living. The HOA includes internet access, pest control, ground maintenance and access to the pool, clubhouse and fitness center. Independence is known for its peaceful surroundings, well-kept landscaping, and prime location near top Winter Garden attractions and highly rated schools. Enjoy easy access to major highways, shopping, dining, and the vibrant Hamlin and Horizon West areas. Whether you're relaxing at home or exploring everything the community has to offer, this townhome delivers comfort, convenience, and a true sense of home. Come experience the lifestyle waiting for you at Independence.

14766 Peekskill Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ O6440957 MLS

Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!

1016 Catori Road, Winter Garden

4 Beds ⋅ 3 Baths ⋅ G5117627 MLS

A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor bedroom and full bath ideal for guests, extended family, or an in-law arrangement**, plus the exceptional Winter Garden lifestyle buyers are looking for. Tall ceilings, 8-foot doors, elegant architectural details, high-end décor, and thoughtfully designed living spaces create an elevated yet comfortable feel throughout. (If the buyer prefers not to keep the furniture and furnishings, they can be excluded from the sale.) The showpiece kitchen is truly the heart of the home, featuring premium quartz countertops, a 5-burner gas range, stainless steel hood, striking designer backsplash, and spacious walk-in pantry. The spa-inspired primary suite offers an expansive private bathroom and generous walk-in closet, creating the perfect retreat. And for a little extra personality, the home even has its very own “Harry Potter” closet! Enjoy Florida living from the inviting screened front porch, complete with a porch swing perfect for morning coffee, an afternoon book, or relaxing at the end of the day. The back patio and fenced yard provide another comfortable setting for entertaining, outdoor dining, or simply enjoying the beautiful Florida weather. An expansive 3-car garage offers exceptional space and storage. Offered fully furnished with beautiful, high-end furnishings and décor, this home is truly turnkey—just bring your suitcase and start enjoying the lifestyle. Located near highly regarded schools and just moments from the West Orange Trail, walk, bike, take your golf cart, or drive to charming Downtown Winter Garden, the Farmers Market, restaurants, shopping, and entertainment. Move in before the holidays and experience everything this incredible community has to offer, including festive neighborhood traditions and upcoming celebrations such as the golf cart parade, fall festival, and more. An exceptional opportunity to own a remarkably equipped home in one of the area’s most desirable communities at an amazing value.

226 Hammock Preserve Loop, Winter Garden

3 Beds ⋅ 3 Baths ⋅ S5156826 MLS ⋅ 10119 BLDG.

This stylish townhome in one of Winter Garden’s most desirable resort-style communities, offers a blend of comfort, convenience, and everyday luxury. The home sits in a beautifully planned neighborhood known for its amenities,GainesvillecinfgainesLoo surroundings, and welcoming atmosphere—an ideal setting for anyone seeking a relaxed yet connected lifestyle. Its location is a major highlight. Winter Garden is home to some of Central Florida’s top-rated schools, making this property especially appealing for families who value strong educational options. You’re also just minutes from premier shopping and dining at places like Hamlin Town Center and Winter Garden Village, giving you easy access to everything from groceries to entertainment. And of course, the magic of Disney theme parks is right around the corner, making weekend outings effortless and adding a touch of excitement to everyday life. This townhome places you in a thriving, fast-growing area where convenience meets resort-style living. With beautiful community amenities, excellent schools, nearby shopping, and world-famous attractions close enough to enjoy anytime, it’s a standout opportunity in one of Winter Garden’s most sought-after.

10119 Salt Point Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ TB8539994 MLS ⋅ 988 BLDG.

Beautiful Family-Oriented Townhouse in a Great Location! Well-maintained and move-in ready, this home offers low-maintenance living with a low HOA fee. Conveniently located approximately 10–17 miles from Walt Disney World, Disney Springs, and many of Orlando’s top entertainment destinations. Easy access to major highways makes commuting and exploring the area convenient. A wonderful opportunity for a family, second home, or investment property. More photos coming soon!

988 Stucki Terrace, Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6438757 MLS ⋅ 1017 BLDG.

Welcome home to a place where life feels just a little easier. Tucked inside the peaceful Westbrook community of Winter Garden, this beautifully maintained, move in ready townhome offers the perfect blend of comfort, style, and convenience. Step inside to discover an inviting open living and dining space that naturally brings everyone together. The heart of the home is the kitchen, thoughtfully designed with gleaming granite countertops, stainless steel appliances, a contemporary tile backsplash, and plenty of space to prepare everything from quick weekday breakfasts to weekend gatherings with friends. Stylish upgraded lighting throughout adds a fresh, modern touch to every room. Upstairs, all three bedrooms create a private retreat away from the main living areas. The spacious primary suite is designed for relaxation and features dual walk in closets, giving everyone room to stay organized. With two additional bedrooms and two and a half bathrooms, there's plenty of flexibility for family, guests, or a dedicated home office. Behind the scenes, a newer high efficiency HVAC system with a UV germicidal light provides year round comfort and added peace of mind. Outside your front door, you'll love being just minutes from Winter Garden Village, the award winning shops and restaurants of Historic Downtown Winter Garden, and the excitement of Disney Springs. Easy access to SR 429 puts Orlando, Tampa, and Central Florida's top attractions within easy reach, making both your daily commute and weekend adventures effortless. Beautiful, meticulously cared for, and ideally located, this is more than a townhome. It's the beginning of your next chapter. Schedule your private showing today.

1017 Priory Circle, Winter Garden

5 Beds ⋅ 4 Baths ⋅ O6440648 MLS

Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 5 bedrooms, 4 full bathrooms, a loft, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and a refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. Three additional first-floor bedrooms and two bathrooms provide comfort and privacy for everyone. Upstairs, enjoy an additional 709 square feet of flexible living space, complete with a generous loft, private fifth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

285 Crystal Wood Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ O6439183 MLS

FORMER BUILDER MODEL HOME - and it shows. When a builder builds their own model, they hold nothing back, and this 4-bedroom, 3.5-bath, 2,958 sq ft home in Waterside on John's Lake is the proof: Upgrades everywhere! Gourmet kitchen with stacked cabinets, 8-foot doors throughout, recessed lighting, wood panel on ceiling, a whole-home speaker system, plus so much more! A finish package that is nearly impossible to replicate today. The open kitchen-living-dining space was designed to entertain. The kitchen is finished wall to wall with stacked upper cabinets plus crown molding, lighted glass-front uppers, quartz countertop, double built-in ovens, gas cooktop, decorative tile backsplash and an oversized island with seating. A butler's pantry and a fully built-out walk-in pantry with its own seating area keep everything in place, and the laundry room is also finished with custom cabinetry, a sink and extra countertop space. Across the room, a floor-to-ceiling stacked-stone wall anchors the living area, with an electric fireplace and the TV and entertainment system built right in, framed by lighted shelving and cabinets. A dedicated study sits off the dining room with its own work island, wall-to-wall shelving and a wood-planked ceiling. A first-floor bedroom with an en-suite bath makes an ideal guest or in-law suite, plus a powder bath for visitors. Upstairs, the primary suite features a wood beam ceiling and a walk-in closet outfitted with a custom shelving system. The primary bath is built around an oversized walk-in glass shower spanning an entire wall, with dual vanities opposite. Two additional bedrooms, a full bath, and a generous loft with a built-in media center complete the second level. Bidets in the baths. Engineered hardwood in the loft and primary bedroom, wood-look tile downstairs. Outside, a screened lanai with a tongue-and-groove wood ceiling opens to a private paver courtyard. The 2-car garage is already fitted with a NEMA 14-50 EV charging outlet, providing extra storage and parking for your Tesla or other electric car. Best of all: NO FRONT NEIGHBORS. The community pool and amenity center sit directly across the street with plenty of guest parking, and there are water views of John's Lake from the front of the home. Waterside on John's Lake offers something most communities do not: a true lap pool with lane markers for training and distance swimming, plus a separate leisure pool. Add a playground, fitness center, clubhouse and oak-canopied trails with picnic and grill areas leading to a lakefront pier for an evening walk or a little fishing. Minutes from Winter Garden Village, Hamlin and SR-429, with downtown Winter Garden's Plant Street, farmers market and the West Orange Trail just up the road - and Disney a short drive away. Model homes are built to sell a neighborhood. Here is your chance to own one - schedule your private showing today.

16924 Tradewind Point, Winter Garden

5 Beds ⋅ 4 Baths ⋅ O6440535 MLS ⋅ 8866 BLDG.

Luxury living in the ENZO Model townhome located in Lakeshore Preserve, a Toll Brothers community surrounded by million-dollar homes in Winter Garden. This spacious executive style townhome offers 5 bedrooms, 4 bathrooms, and over 3,100 square feet of living space, including a private 1-bedroom apartment with kitchenette above the garage and its own private entrance perfect for guests, multigenerational living, or a student retreat. Built in 2017, this home features an open concept layout, Wolf gas cooktop, two gas tankless water heaters, whole home water softener, and two A/C systems with Nest thermostats. Recent updates include luxury vinyl flooring throughout the downstairs, all new carpet installed upstairs and in all bedrooms, and plantation shutters, adding both style and functionality. The home has also been upgraded with over $20,000 in custom closet systems, providing exceptional storage, organization, and convenience throughout. Enjoy the extended wrap around front porch, private courtyard, and even views of Disney fireworks and space launches from the front of the home. Lakeshore Preserve offers resort style amenities including a lakefront clubhouse, fitness center, pool, lake access, kayak launch, volleyball court, firepit, and dog park. Conveniently located near Disney, Hamlin shopping and dining, Flamingo Crossings, Orlando Health, and top rated schools. HOA includes exterior maintenance, cable, internet, and community amenities. A rare opportunity to own a luxury townhome in one of Winter Garden’s most desirable communities.

8866 Bismarck Palm Drive, Winter Garden

2 Beds ⋅ 2 Baths ⋅ S5156278 MLS ⋅ Building 3 BLDG.

Own your piece of the Orlando vacation market at The Grove Resort & Water Park! Located on the 4th floor of Building 3, near the water park, this fully furnished 2-bedroom, 2-bath condo offers the perfect combination of a personal vacation retreat and investment opportunity. The Grove is a Walt Disney World Good Neighbor Hotel located just minutes from the parks, with complimentary shuttle service to Walt Disney World. Owners and guests enjoy resort-style amenities including Surfari Water Park with a lazy river, water slides and FlowRider surf simulator, multiple pools, spa, fitness center, mini golf, arcade, and on-site restaurants and bars. With an on-site rental management program and a prime location near Central Florida’s top attractions, this turnkey condo offers an easy, hands-off ownership opportunity while giving you your own place to enjoy when visiting Orlando.

14501 Grove Resort Avenue Unit 3403, Winter Garden

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