Winter Garden/Oakland Homes for Sale

Winter Garden/Oakland Homes for Sale

Welcome to Winter Garden and Oakland, two enchanting communities nestled in the heart of Central Florida. Known for their picturesque landscapes and vibrant local culture, these charming towns offer a perfect blend of suburban tranquility and urban convenience, making them an ideal place to call home.

Winter Garden, with its historic downtown area, is brimming with quaint shops, delightful restaurants, and a lively farmers' market that takes place every Saturday. The lush greenery and scenic views of the West Orange Trail invite outdoor enthusiasts to explore the beauty of nature, whether it’s biking, walking, or jogging. Just a stone’s throw away, Oakland boasts its own unique charm with a rich history and a tight-knit community feel. The serene lakes and parks provide a peaceful escape, perfect for family picnics and leisurely strolls.

For those considering a move to this idyllic region, there are a plethora of homes for sale that cater to diverse tastes and budgets. From charming single-family homes adorned with Southern-style porches to modern townhouses featuring the latest amenities, Winter Garden and Oakland have something for everyone. Many properties are situated in family-friendly neighborhoods with excellent schools and community facilities, ensuring a nurturing environment for children and adults alike.

Whether you are looking for a tranquil retreat or an active lifestyle, Winter Garden and Oakland offer the perfect backdrop for your next chapter. Explore the available homes for sale today and discover the vibrant community that awaits you in this beautiful corner of Florida!

Newest Winter Garden/Oakland Homes for Sale

$870,000
5 Beds ⋅ 5 Baths ⋅ Harvest/Ovation Ph 2 SubDv. ⋅ 34787 Zip Code
A truly special luxury residence in the highly desirable Harvest at Ovation community of Winter Garden. Professionally designed and curated by a team of high-end architects and interior designers, this magazine-worthy home features soaring ceilings, premium finishes, designer furnishings, elegant décor, and exceptional attention to detail throughout. A standout feature is the fully finished private studio above the garage, complete with full bathroom, walk-in closet, and independent access—perfect as a guest suite, additional apartment, executive office, or private workspace. The gourmet kitchen features premium finishes and a state-of-the-art smart double-door refrigerator with internet connectivity. Enjoy Florida living in the screened outdoor area with mosquito protection, electric retractable awning, outdoor grill, and fenced yard. Additional upgrades include fully paid solar panels, whole-home water filtration, premium kitchen water purification, epoxy garage flooring, LED ceiling lighting, EV charger, and paver waterproofing. Ideally located near excellent schools, shopping, dining, major highways, and Central Florida attractions. **Designer furnishings and décor are negotiable.** A rare opportunity to own a beautifully designed luxury home where every detail has been thoughtfully perfected. This is one you truly need to see in person.

16192 Honey Harvest Street, Winter Garden
$2,050,000
5 Beds ⋅ 5 Baths ⋅ Avalon Cove SubDv. ⋅ 34787 Zip Code
Welcome to 9056 Morgana Ct, perfectly positioned on one of the most desirable lakefront homesites in the community, offering expansive water views and an exceptional setting on Hickorynut Lake. Designed to take full advantage of its waterfront location, the home features expansive windows and open living spaces that frame the lake from the moment you step inside. The views continue outdoors, where a resort-style pool and spa, covered outdoor living, and summer kitchen create a seamless connection between the home and the water. Beyond the pool, the backyard leads to a private covered dock with boat and jet ski lifts, making days on the lake effortless. Whether enjoying quiet mornings by the water, entertaining poolside, or watching the sunset over the lake, this is Florida waterfront living at its finest. Inside, soaring ceilings, abundant natural light, sophisticated finishes, and generously sized living spaces create a luxurious yet inviting atmosphere. With its remarkable lake views, private waterfront setting, and resort-style outdoor living, this is truly one of the premier lakefront opportunities in the community.

9056 Morgana Court, Winter Garden
$1,050,000
5 Beds ⋅ 5 Baths ⋅ Oxford Chase SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this truly exceptional estate home in the exclusive gated community of Oxford Chase, a residence that blends thoughtful design, upscale finishes, and resort-style living. Nestled on a serene lot, this 5-bedroom and 4.5-bathroom home offers a rare combination of space, privacy, and family-forward features. As you arrive, the three-car garage and manicured frontage set a high end tone. Inside, soaring high ceilings and an expansive open-concept layout create effortless flow with New Hardwood Flooring throughout. A dedicated office supports work-from-home needs, and an attached mother-in-law suite with its own private exterior entrance provides true multigenerational flexibility or guest privacy. Entertainment shines with a theater room, game room, and stylish bar area, ideal for gatherings large or small. Walk-in closets, abundant natural light, and premium finishes underscore quality throughout. This home comes with a New Dog/Pet Room and a Pet Shower. Step outside to your own gorgeous fully fenced backyard oasis featuring a fully equipped summer kitchen, perfect for grilling and gatherings. Situated across the street from SunRidge Elementary and SunRidge Middle Schools, the location is unmatched for families. Oxford Chase is a secure, gated enclave, and a new public park, Tucker Ranch Wellness Park, is under development on the neighborhood corner, bringing additional green space and recreation just steps away. The famous Winter Garden Farmers Market is just a few minutes away driving, making it even more special. Convenient to premier shopping, dining, and major roadways. This home delivers luxury and location in equal measure.

14825 Ellingsworth Lane, Winter Garden
$1,071,270
4 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
Under Construction. 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 4 bedrooms, 3 full bathrooms, a convenient first-floor powder room, an enclosed flex room, 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, a decorative tile backsplash, farmhouse sink, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and 48-inch side-by-side 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. The enclosed flex room at the front of the home adds valuable versatility and can easily function as a home office, fitness room, playroom, or creative studio. Two additional first-floor bedrooms located in the opposite back corner of the owner’s suite provide comfort and privacy for everyone. A conveniently located powder room further enhances the home's thoughtful design. Upstairs, enjoy an additional 884 square feet of flexible living space, complete with a generous loft, private fourth 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.

289 Crystal Wood Drive, Winter Garden
$1,395,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and presented in like-new condition, this exceptional single-story lakefront home blends an elevated luxe coastal feel with relaxed Florida waterfront living. Set on a rare oversized lot along skiable Huckleberry Lake, the property offers exceptional privacy and space, with approximately 40 feet of separation between neighboring homes. The light and inviting interior features four bedrooms, three full baths, and a spacious open-concept floor plan. The beautifully updated kitchen showcases quartz countertops and flows seamlessly into the main living and entertaining areas. A generously sized open flex room offers additional versatility as a formal dining room, home office, formal living room, or sitting room and can easily be enclosed for additional privacy. Step outside to a large fenced backyard with a private pool and spa, all overlooking Huckleberry Lake. Enjoy direct lake frontage and water access, with the opportunity for a private dock, subject to applicable HOA approval and permitting. The three-car garage includes a Tesla EV charger, and the expansive driveway accommodates up to six additional vehicles. Lakeview Pointe offers a community dock on Huckleberry Lake, resort-style pool with splash area, and fully equipped fitness center. The HOA also takes care of the home's exterior lawn maintenance, giving you more time to enjoy the lake, pool, and Florida lifestyle. Ideally located in Winter Garden's Horizon West area, with easy access to SR 429 and minutes from shopping, dining, entertainment, and everyday conveniences. The property is currently zoned for A-rated Summerlake Elementary, Hamlin Middle School, and Horizon High School. Nearby early-learning options include Primrose School of Horizon West, The Learning Experience - Horizon West, and KLA Schools of Horizon West. Walt Disney World is approximately 20 minutes away. Buyers should independently verify current school assignments and grades. A rare opportunity to own a beautifully remodeled single-story pool home on skiable Huckleberry Lake, combining privacy, flexible living spaces, an oversized lakefront lot, and true Florida waterfront living.

14048 Larkspur Lake Drive, Winter Garden
$774,990
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Experience elevated Florida living in this stunning 3-bedroom, 3-full-bathroom residence boasting 2,976 square feet of beautifully designed living space, plus a dedicated office, spacious loft, and versatile bonus room. Perfectly positioned on a premium lakeview homesite, this exceptional property offers tranquil water views and the spectacular bonus of enjoying Disney fireworks from your own backyard. Step outside into your private backyard oasis, where a sparkling pool creates the perfect setting for relaxing, entertaining, and enjoying the Florida lifestyle. The fully fenced backyard provides both privacy and space, while the premium lot offers a picturesque backdrop that truly sets this home apart. Inside, the home is thoughtfully appointed with upscale details throughout. The gourmet-inspired kitchen features 42-inch cabinetry, complemented by upgraded light fixtures and designer-style ceiling fans throughout the home. The spacious bonus room, enclosed by elegant frosted-glass doors, offers a flexible space ideal for a media room, home office, entertaining, or additional living space. The dedicated office and generous loft provide even more versatility for today’s lifestyle. Additional highlights include a 2024 A/C, 2025 water heater, and an impressive 25-foot extended garage offering exceptional storage and flexibility for vehicles, recreational equipment, or hobbies. Adding to the ease of Florida living, the HOA includes landscaping and hedge trimming, allowing you to spend more time enjoying your home and less time maintaining it. From the premium lakefront setting and private pool oasis to the thoughtful upgrades, expansive floor plan, and unforgettable Disney fireworks views, this is a home that delivers an exceptional blend of luxury, comfort, and lifestyle.

14735 Snowy Egret Street, Winter Garden
$479,900
4 Beds ⋅ 3 Baths ⋅ M C Britt Sub 1 SubDv. ⋅ 34787 Zip Code
Brand-New Construction in Winter Garden! Welcome to 231 E Lafayette Street, a beautifully designed 4-bedroom, 3-bathroom new construction home offering modern luxury, thoughtful craftsmanship, and exceptional functionality. From the moment you arrive, the striking contemporary exterior, covered front entry, and attached garage create an inviting first impression. Inside, the open-concept floor plan features luxury vinyl plank flooring throughout, soaring ceilings, recessed lighting, and an abundance of natural light. The stunning chef's kitchen is the centerpiece of the home, showcasing custom cabinetry, elegant quartz countertops, a large center island with breakfast bar, designer backsplash, stainless steel appliances, and a statement gold-finished faucet. The spacious island provides the perfect gathering space for entertaining or everyday living. The generously sized living area has a dramatic custom built-in feature wall with integrated shelving and a modern electric fireplace, creating a focal point. Large windows overlook the backyard and bring the outdoors in, while the contemporary ceiling fan and designer lighting add to the home's polished aesthetic. The primary suite provides a private retreat with ample space and a beautifully appointed en-suite bathroom, while three additional bedrooms, flexibility for family, guests, a home office, or media space. The home's three full bathrooms are finished with modern fixtures and elevated designer details. Outside, the property has a private fenced backyard with plenty of room to create your own outdoor oasis. The attached one-car garage and extended driveway provide convenient parking and storage. Ideally located in Winter Garden, this exceptional new construction home combines modern luxury with the charm and convenience of one of Central Florida's most desirable communities. Enjoy easy access to downtown Winter Garden, shopping, dining, parks, major roadways, and everything the area has to offer. New construction. Modern design. Premium finishes. Prime Winter Garden location. This is a home you don't want to miss.

231 E Lafayette Street, Winter Garden
$1,170,000
5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Welcome home to this like-new luxury home in Lakeshore Preserve, the highly desirable community in Horizon West (West Orange County). Great location just off the 429 Western Beltway providing easy access to Orlando and Tampa, and less than 8 miles to Disney parks. You can even view the Disney fireworks nightly from this neighborhood. Wonderfully situated on one of the largest Executive Home sites with views of the green space in the back and a pond across the street, the Toll Brothers Gardenia Model is sure to please the pickiest buyers. This floor plan of just under 4200 sf offers 10' ceilings, 2 primary suites, 3 additional bedrooms, an enormous bonus room, 4 1/2 bathrooms, an extended screened patio downstairs and screened balcony upstairs to enjoy the views and outdoors. Attractive tile roof, tankless water heater, low-e windows and natural gas provide the maximum energy efficiency. Beautiful upgrades are found throughout the home starting with the luxury vinyl plank flooring in all the downstairs living areas. The well-appointed kitchen features an extended island with eating area, upgraded appliances and fixtures, convection oven, deep farmhouse sink and plenty of cabinetry. Off the kitchen is the butler's pantry and walk-in pantry leading to a formal dining room. Entertaining is a breeze with the open floor plan combining the kitchen with the family room with 3 huge sliding doors opening to the oversized brick-paver screened patio. The downstairs primary suite is spacious and works well for multi-generational households. The upstairs primary suite is even larger and its luxury, spa-like bathroom is like no other with a custom stand-alone 7' tub, oversized frameless shower with multiple shower heads, and 2 walk-in closets with custom organizers. A 22' x 18' loft separates the primary bedroom from the remaining 3 bedrooms and 2 additional full bathrooms. Come enjoy the Lakeshore lifestyle and amenities including clubhouse where numerous social activities are held to network with fabulous neighbors, a resort-style pool, fitness center, volleyball court, playgrounds, dog park, and canoes to enjoy Panther Lake which wraps around the clubhouse. The HOA fee includes grounds maintenance, 1 gig internet, cable, sidewalk pressure washing, and all amenities. Make your appointment to view this one in person. It's even more beautiful than the photos.

8222 Topsail Place, Winter Garden
$899,990
5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
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. Step into the Imperial, where luxury and convenience seamlessly combine to create a truly elevated living experience. This remarkable 5-bedroom, 3.5-bathroom home with a 2-car garage situated on a conservation view homesite offers unparalleled craftsmanship and thoughtful design throughout. The open-concept layout flows effortlessly, creating an expansive, airy feel that exudes both sophistication and comfort. On the first floor, discover a private en suite bedroom with a walk-in closet and elegant quartz countertops—a perfect retreat for guests. At the heart of the home, the chef-inspired kitchen is a true masterpiece, featuring Winstead White stacked cabinetry, striking quartz countertops and a decorative tile backsplash. Built-in Whirlpool stainless steel appliances, including a refrigerator and natural gas cooktop, make cooking a pleasure. The kitchen seamlessly connects to the café and gathering room, where a sliding glass door opens to the covered lanai, featuring pre-plumbing for an outdoor kitchen to enhance indoor-outdoor living, all overlooking tranquil conservation views. The first floor also offers a convenient powder room, perfect for guests, as well as a bedroom with an attached bathroom. Upstairs, the luxurious owner’s suite is a private sanctuary, featuring a spacious walk-in closet and a spa-like en suite bathroom with quartz-topped dual vanity sinks and a frameless glass enclosed shower. The loft area provides the perfect space to unwind, while three additional bedrooms and another bathroom complete the upper level. For added convenience, a thoughtfully located upstairs laundry room simplifies everyday tasks. Beautiful wood-look tile flooring is found throughout the first floor, laundry room, and bathrooms, while plush, stain-resistant carpet complements the loft and bedrooms. Designer-curated finishes elevate every corner of this home, including thoughtfully placed brushed nickel plumbing fixtures and hardware, comfort height toilets, Whirlpool washer and dryer, 2” faux wood blinds, and wood treads and risers at the staircase. This home is equipped with a smart thermostat, video doorbell, and LED down lights ensuring your home is as connected as it is beautiful. This home offers the perfect combination of luxury, convenience, and modern design—an ideal place to live and relax. Schedule a tour today!

427 Winter Grove Boulevard, Winter Garden
$975,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3a SubDv. ⋅ 34787 Zip Code
Welcome to 9566 Bolero Rd, where luxury, space, and location come together in one of Central Florida’s most desirable and rapidly growing communities—Winter Garden. Situated on a premium 60-foot lot with beautiful pond views, this impressive North Haven model offers 5 bedrooms, 3.5 baths, a first-floor primary suite, spacious loft, and oversized fenced yard, all tucked away on a quiet cul-de-sac. Step inside through the dramatic two-story foyer and discover a bright, modern floor plan designed for both everyday living and entertaining. The gourmet kitchen features 42” cabinetry with crown molding, upgraded stainless-steel appliances, a vent hood, generous workspace, and an open layout overlooking the family room and picturesque pond beyond. Extend your living outdoors to the spacious backyard featuring a pergola, fenced yard, and tranquil water views—the perfect setting for morning coffee, entertaining, or relaxing at the end of the day. The first-floor primary suite offers privacy and convenience with a spacious walk-in closet and ensuite bath featuring dual vanities, a large walk-in shower, and garden tub. Upstairs, a generous loft provides flexible space for a media room, playroom, home office, or second living area. Bedrooms 2 and 3 share a full bath, while Bedrooms 4 and 5 are connected by a convenient Jack-and-Jill bath. The laundry room is also pre-plumbed for a utility sink. Enjoy the benefits of a resort-style, maintenance-free community while being surrounded by everything that makes Winter Garden such an exceptional place to call home. The area continues to flourish with new restaurants, shopping, grocery stores, entertainment, and everyday conveniences, while still offering the charm and lifestyle Winter Garden is known for. Enjoy easy access to Walt Disney World, Disney Springs, Publix, SR-429, I-4, and SR-417, connecting you to Orlando’s world-class attractions, employment centers, and entertainment. Whether you're enjoying peaceful pond views from your backyard, exploring nearby dining and shopping, or heading out for a day at Disney, 9566 Bolero Rd offers the space, lifestyle, and location you've been looking for. Welcome home!

9566 Bolero Road, Winter Garden
$575,000
3 Beds ⋅ 3 Baths ⋅ Chapin Station SubDv. ⋅ 34787 Zip Code
Virtually Staged. Every update you'd hope to find is already done here — and then some. Fresh interior paint throughout, brand new flooring in every room (Aug 2026), and designer lighting and hardware that give the whole place a current, put-together feel. No projects waiting for you here — just move in. The big-ticket items are already handled too. A newer roof (2021) and owned solar panels (yours outright, no lease) mean lower bills and real peace of mind from day one. That's the kind of upgrade you feel every month. Inside, 2,630 square feet gives everyone room to spread out, with three bedrooms plus a dedicated home office, an upstairs bonus room, and three full baths. Upstairs you'll find a den/flex space that's yours to shape — bedroom, home office, playroom, media room, whatever fits your life — with easy access to attic storage to keep everything else tucked away. The layout is open where it matters, so hosting is easy and everyday life feels effortless. The location is the ultimate standout. Being in the heart of Winter Garden’s golf cart district means you’re just a quick cruise away from the vibrant energy of historic downtown. Spend your Saturdays at the award-winning farmers market, grab a bite on Plant Street, or hop onto the West Orange Trail for some fresh air. With quick access to the 429 and Winter Garden Village, you’re perfectly positioned to enjoy the best of the area. New roof, owned solar, fresh everything, and a golf cart ride from downtown — homes like this don't sit long. Come see it before it's gone.

1331 Lindzlu Street, Winter Garden
$1,750,000
4 Beds ⋅ 4 Baths ⋅ West Lake Hancock Estates SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to an exceptional lakefront estate on the shores of Lake Hancock, one of Central Florida's premier ski lakes. Situated on an expansive 1.26-acre homesite, this beautifully designed residence offers 4 bedrooms, 3 full bathrooms, 1 half bathroom, and nearly 3,400 square feet of thoughtfully crafted living space with breathtaking water views. The open-concept floor plan is perfect for both everyday living and entertaining, featuring formal living and dining rooms, a spacious family room, and a gourmet kitchen complete with quartz countertops, 42-inch cabinetry, stainless steel gas appliances, a pot filler, farmhouse sink, and a convenient butler's pantry. The split-bedroom layout provides privacy, while the bonus room offers endless possibilities as a media room, game room, home office, or home gym. Step outside to your private Florida oasis featuring a screened-in pool and private boat dock with direct access to Lake Hancock. Spend your days boating, skiing, or simply relaxing while enjoying spectacular sunsets and nightly Disney fireworks from your own backyard. Additional highlights include a 3-car garage, high ceilings, elegant architectural details, and access to outstanding community amenities including a resort-style pool, splash pad, clubhouse, fitness center, and scenic walking and biking trails. Ideally located just minutes from Hamlin Town Center, shopping, dining, top-rated schools, SR 429, and Walt Disney World, this remarkable waterfront home offers the perfect combination of luxury, privacy, and convenience.

7573 Green Mountain Way, Winter Garden
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