Winter Garden Homes with Playground Amenities

Winter Garden Homes with Playground Amenities

Welcome to Winter Garden, Florida – a vibrant city where charming small-town vibes meet modern convenience! Nestled just a short drive from the bustling heart of Orlando, Winter Garden is known for its picturesque landscapes, historic downtown, and an array of outdoor activities that cater to residents of all ages. With its rich agricultural history, the city boasts delightful farmers' markets, scenic walking trails, and a thriving community spirit that makes it a perfect place to call home.

One of the standout features of Winter Garden is its commitment to family-friendly living, particularly evident in the neighborhoods that offer homes with playground amenities. Imagine stepping out of your front door to find well-maintained playgrounds just a short stroll away, where your children can play, explore, and make new friends. These vibrant community spaces are designed to foster connections among families while providing safe environments for kids to enjoy outdoor adventures.

The homes in Winter Garden are as diverse as the community itself, with options ranging from charming single-family residences to luxurious estates. Many of these properties are situated within family-oriented neighborhoods, ensuring that you have easy access to parks, playgrounds, and recreational facilities. The blend of beautiful architecture and modern amenities creates a welcoming atmosphere for families looking to grow and thrive.

Whether you’re drawn by the allure of outdoor activities, the charm of a close-knit community, or the convenience of nearby urban amenities, Winter Garden is a place where dreams of homeownership come to life. Explore this enchanting city and discover your perfect home today!

Newest Winter Garden Homes with Playground Amenities

17449 Water Hemlock Road, Winter Garden
$1,099,990
5 Beds ⋅ 5 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. The Newport home at 17449 Water Hemlock Road has something for everyone! Learn more about this 5-bedroom home by contacting our team today! Welcome to your new home at 17449 Water Hemlock Road in Winter Garden, a thoughtfully designed quick move-in opportunity ready when you are! This beautifully crafted new construction home offers 5 spacious bedrooms and 5 full baths, designed for comfort and everyday living. The open-concept layout creates a seamless connection between the kitchen, dining, and living areas, making the home feel bright, open, and welcoming. Natural light pours in throughout the day, accentuating stylish finishes and a layout that’s as practical as it is inviting. The owner’s bedroom serves as a private retreat with plenty of room to relax and recharge. Your en-suite owner’s bathroom provides a comfortable, spa-inspired setting with thoughtful finishes and ample space designed to make daily routines feel effortless and relaxing. Additional bedrooms provide versatility for guests, a home office, or creative spaces to fit your lifestyle, while a 2-car garage adds everyday convenience and extra storage. Located in a welcoming neighborhood, this home home offers the perfect balance of style and simplicity. Whether you’re enjoying a quiet morning at home or hosting friends and family, the layout supports a comfortable, easygoing lifestyle designed to grow with you for years to come. This new construction home delivers style, comfort, and move-in-ready ease without the wait. This move-in-ready new construction home delivers modern style, thoughtful design, and the convenience of no build wait. Contact us today to learn more about this exceptional home at 17449 Water Hemlock Road!

17449 Water Hemlock Road, Winter Garden
17437 Water Hemlock Road, Winter Garden
$869,990
4 Beds ⋅ 4 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to this stunning new construction home by M/I Homes, located at Lake Star At Ovation, Winter Garden, Florida. This 2-story home offers 2,343 square feet of thoughtfully designed living space with 4 bedrooms and 4 bathrooms, delivering both comfort and functionality for today's lifestyle. Step inside to discover an open-concept living space that creates a seamless flow between the main gathering areas, perfect for everyday living and entertaining. The quality of design is evident throughout, with carefully selected finishes and attention to detail in every room. Key Features: 4 bedrooms and 4 bathrooms 2,343 square feet of living space 2-story new construction by M/I Homes Open-concept living space Spacious owner's bedroom with en-suite bathroom Covered lanai for outdoor relaxation Quality construction and premium finishes throughout The owner's bedroom features a private en-suite bathroom, providing a comfortable retreat at the end of the day. The lanai extends your living space outdoors, offering a wonderful area to unwind and enjoy the Florida weather. This home is nestled within a vibrant neighborhood with convenient proximity to parks, making it an ideal setting for families and outdoor enthusiasts alike. The well-planned layout maximizes every square foot, ensuring that each room serves a purpose while maintaining an inviting atmosphere throughout.

17437 Water Hemlock Road, Winter Garden
6099 Flowering Cherry Bend, Winter Garden
$829,496
4 Beds ⋅ 3 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
Under Construction. Find room to spread out in this thoughtfully configured Biscayne, Elevation B, at Avalon Woods. Four bedrooms and three full baths include a first-floor bedroom and full bath, giving you flexibility for guests or a home office. The open great room, dining area and gourmet kitchen make it easy to stay connected, with laminate flooring adding warmth to the main living spaces. The kitchen brings together an island, quartz countertops, white cabinetry, a built-in oven, electric cooktop, microwave and range hood. Upstairs, the extended primary suite offers generous walk-in storage and a spa-style shower, while a spacious bonus room gives you another place to relax, play or gather. Two additional upstairs bedrooms and an upstairs laundry room with cabinets and a sink add everyday convenience. Open the hidden sliding glass door to the covered rear lanai for a quiet morning or an easy evening outdoors. A covered front porch, stone accents and an attached two-car garage complete the picture. Discover the possibilities of this home under construction in Winter Garden.

6099 Flowering Cherry Bend, Winter Garden
9228 Bradleigh Drive, Winter Garden
$975,000
5 Beds ⋅ 5 Baths ⋅ Latham Park South SubDv. ⋅ 34787 Zip Code
Having Mickey Mouse as a neighbor, excellent schools nearby & convenient access to everything Central Florida has to offer, this extraordinary home in Winter Garden's desirable LATHAM PARK community delivers location, luxury & a lifestyle worth getting excited about! Built in 2019, this stunning DUVAL floor plan is over 3,600 sq. ft, offers 5 bedrooms, 4 1/2 baths, a 3 car tandem garage and no rear neighbors! Lovingly cared for by its original owners, this will be one of the most immaculate preowned homes you'll ever experience! From the original splurge of design center selections to the thoughtfully chosen aftermarket upgrades, attention to detail is evident throughout. The exceptional floor plan strikes a beautiful balance between a grand, open living space to cozy, intimate retreats. An elegant paver driveway welcomes you home, while the charming front porch offers the perfect spot to escape with a good book and enjoy your morning coffee. Step inside to discover a beautifully coordinated color palette, w/ a custom created “Heather Taupe” paint & sophisticated finishes that create a warm & inviting atmosphere. Just off the foyer, a downstairs bedroom w/ access to a full bathroom provides wonderful flexibility for guests or multigenerational living (currently a gym). Continue through the home, where a formal dining area (pottery barn pool/dining table) & convenient butler's pantry lead into the breathtaking 2 story family room, with soaring ceilings, abundant natural light & a spectacular sense of openness! The adjoining gourmet kitchen is designed for anyone who loves to cook, entertain, or simply appreciate a gorgeous space. A magnificent oversized quartz island anchors the room, surrounded by abundant real wood cabinetry w/ soft close drawers and all the goodies offered to store utensils, spices including a concealed garbage/recycle cabinet! From your holiday dinnerware to your ever growing collection of charcuterie boards and entertaining essentials, everything is within reach! Beautifully upgraded lighting & plumbing fixtures throughout the home add another layer of refinement. Downstairs, top of the line waterproof luxury vinyl plank flooring lets each room flow nicely into the other. And of course the “why didn’t we have one of these in our old house” water filtration system that provides safe and delicious water for your family. Downstairs has a cute drop zone just off the garage w/ a bench & ample storage closet under the stairs. Upstairs, the spacious primary suite offers a peaceful private retreat, complemented by generously sized secondary bedrooms with large walk in closets & an ensuite bath. A large 5th bedroom has double doors and is used as a media room! Internet is hardwired & speakers sweeten the experience! Speakers were added throughout the house, including the outdoor area! (All can be found behind a tidy panel in the amazing upstairs laundry!) As you step outside to the screened lanai, the peaceful conservation setting invites you to sit awhile, creating a lovely backdrop, with the added magic of enjoying Disney fireworks from home! Latham Park residents also enjoy a beautiful community pool that looks like Joanna Gaines herself designed. Other neighborhood amenities include a nature walk & playground. Historic Downtown Winter Garden & Hamlin are just minutes away & always creating nostalgic hometown activities! WHY BUILD WHEN THIS ONE IS ALREADY SO BEAUTIFULLY DONE & ON A PREMIUM LOT!

9228 Bradleigh 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
15530 Sunquat Dr, Winter Garden
$599,999
4 Beds ⋅ 4 Baths ⋅ Hamlin Reserve SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this stunning 4-bedroom, 3.5-bath home located in the highly desirable Hamlin Reserve community in Horizon West, Winter Garden! Thoughtfully designed with spacious living areas, modern finishes, and a versatile floor plan, this home offers the perfect setting for comfortable everyday living and effortless entertaining. Upon entering, you are greeted by an inviting foyer featuring soaring volume ceilings and stylish vinyl flooring throughout the entire first floor. A versatile flex room just off the entry provides endless possibilities and can be customized to suit your needs as a home office, den, formal living room, or additional dining space. The open-concept layout seamlessly connects the spacious family room, kitchen, and dining area, creating a warm and welcoming atmosphere. The well-appointed kitchen is sure to impress with its oversized island with seating, granite countertops, solid wood cabinetry, gas range, stainless steel appliances, and beautiful decorative backsplash. Conveniently located nearby are a half bath, a dedicated mudroom area with access to the garage, and sliding glass doors that open to the covered rear patio, offering the perfect spot to unwind or enjoy outdoor gatherings. Upstairs, you'll discover a spacious loft that provides additional flexible living space, ideal for a media room, playroom, or secondary family gathering area. The thoughtfully designed split-bedroom floor plan offers added privacy and functionality. The generously sized primary suite serves as a peaceful retreat, featuring a private en-suite bathroom with dual sinks, a standalone shower, and a walk-in closet. The second floor is completed by a conveniently located laundry room just off the loft, a private en-suite bedroom with its own standalone shower, two additional spacious bedrooms, and a full bathroom. For added convenience and modern appeal, all four bathrooms feature smart toilets. Residents of Hamlin Reserve enjoy wonderful community amenities, including a community pool, playground, and clubhouse. Ideally situated in the heart of Horizon West, this home is within walking distance of local dining and everyday conveniences, with Cinepolis, PopStroke, an exciting variety of restaurants, breweries, shopping, and entertainment just minutes away. Experience the best of the Horizon West lifestyle with this beautiful home offering space, comfort, community amenities, and an unbeatable location. Schedule your private showing today!

15530 Sunquat Dr, Winter Garden
17316 Melogold Way, Winter Garden
$530,047
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a two-car garage, perfectly located in the heart of Winter Garden. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. This popular Walden plans features finishes from the AW Collection Milan with clean, modern touches. The kitchen boards 42" cabinets, quartz countertops and tiled backsplash. Additional highlights include a detached two-car garage with private fenced courtyard space and upgraded 8' doors. Ideally situated, you’re just 37 minutes from Orlando International Airport, 20 minutes from world-famous Disney theme parks, and 30 minutes from Celebration. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17316 Melogold Way, Winter Garden
271 Daniels Pointe Drive, Winter Garden
$355,000
3 Beds ⋅ 2 Baths ⋅ Daniels Crossing SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the desirable Daniels Crossing community of Winter Garden! Featuring a bright, open floor plan, fresh modern finishes, and a comfortable living and dining area, this home offers the perfect blend of style and functionality. Enjoy peaceful pond views from your backyard, creating a relaxing setting to unwind and enjoy Florida living. The split-bedroom layout provides added privacy, while the attached 2-car garage offers convenience and extra storage. Residents can also enjoy the community pool. Conveniently located near shopping, restaurants, major roadways, and the popular Winter Garden Village, this home offers both comfort and an excellent location. Don't miss the opportunity to make this home yours!

271 Daniels Pointe Drive, Winter Garden
704 Caterpillar Run, Winter Garden
$675,000
4 Beds ⋅ 3 Baths ⋅ Mcallister Lndg SubDv. ⋅ 34787 Zip Code
Don't miss this one-of-a-kind, move-in-ready corner home featuring 4 bedrooms, 3 full baths, a dedicated office, and a 3-car attached garage, all on one level! Built in 2019, this spacious 3,000+ sq. ft. home offers an open, functional floor plan with vinyl flooring throughout, ceramic tile in wet areas, window treatments that convey and high ceilings. The home features separate living and dining areas, a spacious family room, and an open kitchen with granite countertops, center island, stainless steel appliances, and built-in oven and cooktop. The primary suite offers a large walk-in closet, double vanity, walk-in shower, separate soaking tub, and sliding glass door access to the oversized screened lanai. Additional bedrooms include a convenient guest suite with private bath. Enjoy the extended, full-length screened lanai with two ceiling fans, perfect for relaxing or entertaining. The sellers have made numerous improvements, including gutters, exterior paint (2022), epoxy-coated garage floor, built-in workbench, wall storage systems, and four overhead storage racks. The outdoor space features paver walkways and grilling pad, artificial turf with stepping stones, and a variety of fruit trees, including avocado, papaya, grapefruit, orange, and key lime, along with raised garden beds and an underground irrigation system. A transferable termite bond adds peace of mind. This beautifully maintained home offers space, functionality, and numerous upgrades. Schedule your private showing today!

704 Caterpillar Run, Winter Garden
15543 Kinnow Mandarin Lane, Winter Garden
$648,000
3 Beds ⋅ 3 Baths ⋅ Highlands/Summerlake Grvs #1 SubDv. ⋅ 34787 Zip Code
Discover the best of Horizon West living in this beautifully maintained home nestled in the sought-after Highlands at Summerlake Groves in Winter Garden! Offering 3 bedrooms, 2.5 bathrooms, and a spacious open-concept design, this inviting residence blends modern comfort, thoughtful features, and exceptional indoor-outdoor living. Step inside to light-filled living spaces and an airy atmosphere that welcomes you home. The beautifully appointed kitchen features elegant quartz countertops, abundant cabinetry, and stainless steel appliances, opening seamlessly to the spacious great room, an ideal setting for entertaining or enjoying everyday moments. Walk upstairs to impressive high ceilings that adds to the home's open and spacious feel. The generous primary suite provides a peaceful retreat, complete with a walk-in closet and an en-suite bathroom featuring a relaxing Jacuzzi tub. The three additional generously sized bedrooms are conveniently located upstairs, offering guests and family members added privacy and comfortable personal space. This well-designed layout provides the perfect balance of togetherness and privacy for everyone to enjoy. Enjoy the added ease of natural gas service, 1 Gbps high-speed internet for streaming, working, and staying connected, and an attached two-car garage featuring a high-profile garage door and built-in storage shelving. Another appealing feature is the average monthly electric bill of approximately $150–$200, depending on usage and season. Take your Florida lifestyle outdoors in the private backyard retreat, where an inviting outdoor summer kitchen and natural gas fire pit create the perfect setting for weekend gatherings, evening relaxation, and entertaining family and friends. Both the outdoor kitchen and fire pit are plumbed directly to the home's natural gas supply for added convenience. Beautifully upgraded landscaping further enhances the home's curb appeal and outdoor setting. The Highlands at Summerlake Groves offers an outstanding array of community amenities, including a swimming pool, two tennis courts, dog park, two playgrounds, soccer field, and picnic areas with grills. Ideally situated near Orange County National Golf Center, Hamlin Town Center, shopping, restaurants, grocery stores, Orlando Health Hospital, major roadways including the 429, and local schools. Walt Disney World and the area's many attractions are also just a short drive away. With its desirable location, inviting living spaces, natural gas outdoor entertaining features, and wonderful community amenities, this home offers an exceptional opportunity to enjoy the very best of Winter Garden living. Come see all this beautiful home has to offer!

15543 Kinnow Mandarin Lane, Winter Garden
7723 Green Mountain Way, Winter Garden
$2,695,000
6 Beds ⋅ 7 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
Set along the shores of Lake Hancock with approximately 80 feet of lake frontage, this exceptional Winter Garden residence offers private boating amenities and expansive indoor-outdoor living. A two-story dock with a boat lift and two Jet Ski lifts, a screened pool and spa, and sweeping lake views define this waterfront setting. Offering 6 bedrooms, 6.5 bathrooms, over 5,100 square feet, a 3-car garage, and two primary suites on separate floors, the flexible layout is ideal for multigenerational living. A paver driveway, tile roof, stone accents, and mature landscaping welcome you home. Inside, engineered hardwood floors lead past a formal dining room on the right, connected to the kitchen through a butler's pantry, and a dedicated office on the left. The impressive two-story living room features decorative wood beams, a cascading chandelier, and a floor-to-ceiling stacked-stone accent wall. Expansive sliding glass doors open to the covered lanai, seamlessly connecting indoor and outdoor living while framing views of the pool and Lake Hancock. An open staircase with wood treads and wrought-iron balusters overlooks the living area. Just off the living room, the first-floor primary suite offers direct lanai access, a walk-in closet, separate vanities, and an oversized tiled shower. The spacious kitchen features a center island, an expansive wraparound peninsula with a farmhouse-style sink, granite countertops, cream-colored cabinetry, stainless steel appliances, a natural gas cooktop with pot filler and vent hood, a built-in microwave and wall oven, decorative tile backsplash, and built-in wine storage. A separate casual dining area overlooks Lake Hancock. Beyond it are a second downstairs bedroom and adjacent full bathroom with pool access. Near the 3-car garage, the laundry room provides a utility sink, cabinetry, and counter space. A half bath completes the first floor. Upstairs, the second primary suite features a tray ceiling, French doors to a private lakeview balcony, two walk-in closets, and an ensuite bath with dual vanities, soaking tub, and glass-enclosed shower. Three additional bedrooms and three full bathrooms, including two ensuite bedrooms, offer flexible accommodations. An expansive bonus room with hardwood flooring, lake-facing windows, and French doors to a separate balcony makes an ideal second living area, game room, or media room. Outdoor living takes center stage on the spacious covered lanai, with separate dining and lounge areas, ceiling fans, and a summer kitchen featuring a stainless steel grill, vent hood, refrigerator, and countertop space. The screened pool and spa, surrounded by an expansive paver deck, overlook Lake Hancock. Beyond the shoreline, the private two-story dock features a shaded lower seating area, boat lift, two Jet Ski lifts, and an open-air upper observation deck with panoramic lake views. From the living room and upstairs balconies to the pool and dock, the water is part of everyday life here. Summerlake community amenities include a pool, fitness center, tennis courts, playgrounds, and walking paths. Convenient to Hamlin Town Center, major highways, and Central Florida's world-famous attractions, this home offers an exceptional Lake Hancock waterfront lifestyle.

7723 Green Mountain Way, Winter Garden
6123 Flowering Cherry Bend, Winter Garden
$844,073
6 Beds ⋅ 5 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
Under Construction. Discover the Anna Maria with Bonus in Avalon Woods! This two-story home offers 6 bedrooms, 4 full bathrooms, 1 half bathroom, and approximately 3,412 square feet of living space. The main level features a spacious great room, dining area, kitchen, and a private primary suite with a walk-in closet and bath. Upstairs, enjoy a versatile bonus room and additional bedrooms and bathrooms. A two-car garage adds everyday convenience. Community amenities include a park, playground, and trails. Conveniently located near shopping, dining, and major roadways in Winter Garden. Pricing, features, and availability are subject to change; confirm details with the builder.

6123 Flowering Cherry Bend, Winter Garden
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