Winter Garden/Oakland Homes with Playground Community Features

Winter Garden/Oakland Homes with Playground Community Features

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Central Florida. Known for their picturesque landscapes, vibrant downtown areas, and family-friendly atmosphere, these regions offer a perfect blend of suburban tranquility and urban convenience. With a rich history dating back to the early 1900s, Winter Garden has blossomed into a thriving hub, boasting beautiful parks, scenic lakes, and a bustling farmers market that draws locals and visitors alike.

One of the standout features of homes in this area is the abundance of community amenities, particularly those designed for families. Many neighborhoods in Winter Garden and Oakland are equipped with playgrounds, ensuring that children have safe and fun spaces to play and explore. These playgrounds are not just for kids; they serve as gathering spots for families, fostering a sense of community and camaraderie among neighbors. Imagine watching your children laugh and play while you enjoy a leisurely afternoon with friends or neighbors, all within the comfort of your own community.

Additionally, the proximity to top-rated schools, shopping centers, and recreational activities makes Winter Garden and Oakland an ideal choice for families looking to settle down. With easy access to major highways, residents can enjoy the best of both worlds—serene suburban living with the excitement of Orlando just a short drive away. Whether you’re seeking a cozy single-family home or a spacious residence with modern amenities, Winter Garden and Oakland have something for everyone. Come experience the warmth and charm of these delightful communities, where your dream home awaits!

Newest Winter Garden/Oakland Homes with Playground Community Features

5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code

Experience refined living in this exceptional 5-bedroom, 3-full and 2-half bath residence nestled in one of Winter Garden's most desirable communities. Thoughtfully designed with an open-concept floor plan, the expansive great room seamlessly connects to the gourmet kitchen, creating an inviting space for both everyday living and elegant entertaining. The first-floor primary suite offers a private retreat, complete with a spacious layout and spa-inspired bathroom. The primary bath connects to your California style closet and laundry room. Throughout the home, you'll appreciate upscale finishes, including designer lighting, elegant flooring, stone countertops, stainless steel appliances, and architectural details that elevate every space. New carpets and a new Kitchen Aid refrigerator installed in July 2026. Large windows fill the home with natural light, enhancing the bright and airy atmosphere. Four additional bedrooms located upstairs with jack and jill style bathrooms. This home has two bonus areas for maximum entertaining potential, comfort and functionality. This home is also equipped with a whole house water softener, Tesla charger and Govee lights. The backyard is set for entertainment with your summer kitchen, firepit and turf grass. Ideally located near premier shopping, dining, entertainment, parks, and top-rated schools, this home combines luxury, convenience, and timeless style in the heart of Winter Garden. A rare opportunity to own a beautifully appointed turn-key ready home in an exceptional location.

1664 Holcomb Creek St., Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Porter floor plan offers modern living tailored to meet everyday needs with style and functionality.

7276 Windy Willow Street, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage

17320 Wild Daisy Drive, Winter Garden

6 Beds ⋅ 5 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code

Virtually Staged. Pre-Construction. To be built. Anna Maria with Bonus Room: Welcome to this spacious, thoughtfully designed 6-bedroom, 4.5-bath home, offering the perfect blend of comfort and functionality. The heart of the home is the expansive kitchen, featuring a large center island that's ideal for cooking, entertaining, and gathering with friends. The private primary suite is conveniently located on the first floor, providing a peaceful retreat with added privacy. Upstairs, you'll find two generously sized bedrooms, each with access to it's own bathroom, along with a spacious game room that's perfect for movie nights, a play area, or a second living space.

17314 Wild Daisy Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Welcome to The Regina II in Northlake at Ovation, where modern design meets everyday convenience. This thoughtfully crafted home offers spacious living areas perfect for both relaxing and entertaining. Nestled in the highly sought-after Winter Garden area, this home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World. This low maintenance townhome includes a detached two car garage with private fenced courtyard space. The open kitchen boasts plenty of modern upgrades from the AW Collection Coastal such as beautiful 42 inch cabinets, tiled backsplash, and stainless steel appliances. Large island with upgraded quartz countertops perfect for gatherings. The main living areas feature wood look luxury vinyl plank flooring and the bedrooms include upgraded carpet for comfort, plus find upgraded 8' doors throughout the home. Enjoy the neighborhood amenities including a community pool, clubhouse, shaded playground, and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17398 Sweet Moro Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Chapin Station A SubDv. ⋅ 34787 Zip Code

Welcome home to this beautifully maintained pool home in the desirable Chapin Station community of Winter Garden, where location truly sets it apart. Just outside the neighborhood, you'll enjoy direct access to the West Orange Trail at the Chapin Station Trailhead, making it easy to bike, walk, run, or explore miles of scenic trails connecting Winter Garden, Clermont, Oakland, and beyond. Situated on an oversized homesite, this property offers the perfect blend of indoor comfort and outdoor Florida living with a private screened pool and spacious backyard ideal for entertaining and relaxing. Inside, you'll find a thoughtfully designed floor plan with generous living spaces, abundant natural light, and plenty of room for everyday living and hosting family and friends. Conveniently located just minutes from Historic Downtown Winter Garden, residents can enjoy the award winning Farmers Market, Plant Street, Crooked Can Brewing Company, boutique shopping, restaurants, live entertainment, and community events throughout the year. Downtown Clermont, Winter Garden Village, major highways including SR 429 and the Florida Turnpike, Walt Disney World Resorts, Disney Springs, world class sports training facilities, championship golf, and state of the art hospitals and medical centers are all within easy reach. This exceptional home combines an unbeatable location, outdoor recreation, convenient access to Central Florida's top attractions and amenities, and the vibrant lifestyle buyers are searching for.

1339 Hunterman Lane, Winter Garden

4 Beds ⋅ 5 Baths ⋅ Winter Garden Shores 2nd Add SubDv. ⋅ 34787 Zip Code

Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Brewery and West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the character of this historic city, this exquisite 4 bedroom, 4.5-bath home blends timeless charm with refined modern finishes throughout. Majestic oaks beautifully frame the home’s craftsman-inspired architecture, while the expansive front porch invites relaxation. Inside, an open-concept design and modern kitchen are curated for both everyday comfort and endless entertaining. Inviting living spaces are complemented by elevated finishes, a wine bar, custom built-ins, a butler’s pantry & outdoor kitchen. Creatively designed to include a drop zone with a one-of-a-kind dog wash station. All bedrooms feature ensuites and custom closets. Don't miss this one-of-a-kind opportunity. Schedule your private showing today!

412 N Boyd Street, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code

LOCATION, LOCATION, LOCATION! Discover a rare gated lakefront retreat in the heart of Winter Garden, tucked away on a quiet, tree-lined cul-de-sac and conveniently located just minutes from local schools, grocery stores, dining, and Downtown Winter Garden. Enjoy grandfathered boat access on Lake Luntz, breathtaking sunset views, a screened pool with grotto seating and waterfall, a fully equipped Florida Grill/Bar room, and a private boathouse with a covered dock, boat lift, pontoon slip, and jet ski slips. Additional highlights include a guest suite, loft, media room, air-conditioned garage with gym/rec space, and two new AC systems installed in 2025—an exceptional combination of privacy, recreation, and waterfront living.

2450 Dahlgren Way, Winter Garden

2 Beds ⋅ 3 Baths ⋅ Daniels Lndg A-J SubDv. ⋅ 34787 Zip Code

LISTED AT APPRAISED VALUE! Welcome to this beautifully updated townhome in the highly desirable gated community of Daniels Landing in Winter Garden. Combining modern upgrades with an ideal location, this move-in-ready residence offers the perfect blend of style, comfort, and convenience. Step inside to discover an inviting open-concept main level featuring a spacious living room, a well-appointed kitchen with granite countertops, ample cabinetry, a dining area, and a convenient half bath for guests. Luxury wood plank flooring flows throughout the living room and both bedrooms, creating a warm and cohesive feel. Upstairs, you'll find two generously sized primary suites, each complete with walk-in closets and private en-suite bathrooms. The bathrooms were fully renovated in 2025 with designer tile flooring, new vanities, LED mirrors, beautifully tiled showers, new toilets, and contemporary fixtures, creating spa-inspired spaces you'll love. A conveniently located upstairs laundry area adds to the home's thoughtful layout. Extensive recent improvements provide exceptional peace of mind, including a complete HVAC system replacement (2022), new garage door and garage door opener (2025), professionally cleaned air ducts with a UV air purification system (2025), new ceiling fans throughout (2025), and a full suite of brand-new LG stainless steel appliances including the refrigerator, dishwasher, microwave, washer, and dryer (2025). Enjoy Florida living in your private courtyard, accessible from the rear-entry garage, offering a quiet outdoor retreat for relaxing or entertaining. Residents of Daniels Landing enjoy an array of community amenities, including a resort-style pool, fitness center, clubhouse, playground, and gated entry. Ideally situated just minutes from the award-winning Downtown Winter Garden, the West Orange Trail, shopping, dining, major highways, and approximately 20 minutes from Walt Disney World, this exceptional home offers the perfect combination of low-maintenance living and an unbeatable location.

241 Deepcove Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Ready in November 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms, a powder room, spanning 1,881 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your spacious flex space. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Your inner gourmet will be delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.

15159 Groveside Road, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code

Under Construction. Discover elevated living in this thoughtfully designed home at Northlake at Ovation, offering flexible spaces and curated finishes to fit your everyday lifestyle. From the inviting covered lanai to the spacious loft and soaring ceilings, this floor plan provides room to relax, work, and entertain with ease. Inside, you’ll find a balance of bold and neutral finishes from the AW Collection Rosemary. Design upgrades include 8' interior doors, quartz countertops, tiled backsplash, stainless steel appliances and more. Whether you’re hosting gatherings or enjoying quiet evenings at home, the open layout and versatile rooms adapt to your needs. Perfectly located in Winter Garden near some of Central Florida’s most beloved destinations, this home is just 35 minutes from Orlando International Airport, 15 minutes from world-famous Disney theme parks, and 30minutes from charming Celebration. Residents can also enjoy the charm and rich local history of nearby downtown Winter Garden, known for its vibrant shops, and eateries. Paired with great local schools and a peaceful community setting, this home delivers the ideal blend of comfort, convenience, and Central Florida living. Residents also enjoy a clubhouse, community pool, playground areas and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17625 Lake Star Road, Winter Garden

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