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$515,000
4 Beds 3 Baths Oakland Trls Ph 1 SubDv. 34787 Zip Code
INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by newer(2024) luxury plank flooring, a large living/dining area, built-in OFFICE SPACE, and a half sized bathroom. The kitchen is a CHEF'S DREAM featuring granite counters, a large eat-in island, stainless steel appliances, built-in oven and microwave, designer pendant lighting, closet style pantry, and a dedicated coffee/work station. WOW! Head upstairs and pass through the BONUS LOFT area into an OVERSIZED MASTER SUITE with tray ceilings, a large split vanity master bath, and a MASSIVE WALK-IN CLOSET equipped with built-in shelving and organizers. The second floor also contains three secondary bedrooms, a full size hallway bathroom, and a large laundry room. Additional features of the home include: a FULL SOLAR PANEL SYSTEM(providing significant energy savings), an oversized two car garage, built-in security system, and paver driveway. The Oakland Trails community includes a community pool and clubhouse, dog park, playground, and walking trails. Located minutes away from the WEST ORANGE TRAIL this area is a hotbed for outdoor recreation and is ZONED FOR EXCELLENT SCHOOLS! In close proximity to major commuting highways, downtown Winter Garden, and ample shopping amenities, this is a PRIME LOCATION home and MOVE-IN ready for it's next owners. DON'T DELAY!! Book your private showing today.

2259 White Feather Loop, Oakland

$539,900
3 Beds 3 Baths Oakland Trls Ph 2 SubDv. 34787 Zip Code
Welcome to the highly desirable Oakland Trails, where this 2019 Meritage Home combines modern style, energy efficiency, and a thoughtfully designed layout for everyday comfort. Ideally situated approximately 30 minutes from Walt Disney World, Universal Orlando, and Downtown Orlando, the home provides convenient access to Central Florida's most popular destinations while preserving the peaceful atmosphere of an established neighborhood. Designed with functionality and flexibility in mind, this residence offers 3 bedrooms, 2.5 bathrooms, a two-car garage, and over 3,200 square feet of total living space. The open floor plan connects the living area, dining space, and gourmet kitchen, creating an inviting setting for daily living and entertaining. A spacious first-floor flex room offers endless possibilities as a home office, media room, formal living room, playroom, fitness space, guest room, or potential fourth bedroom. The gourmet kitchen features KitchenAid stainless steel appliances, quartz countertops, a custom tiled island, abundant cabinetry, and generous workspace while overlooking the main living and dining areas. High ceilings and oversized interior doors enhance the bright, open feel throughout the home. Upstairs, the primary suite includes a custom walk-in closet system and an ensuite bathroom. Additional bedrooms are generously sized, with ample storage throughout. Built with Meritage Homes' renowned energy-efficient construction, the home includes spray foam insulation, an advanced HVAC system with fresh-air intake and enhanced air purification, a combination metal and shingle roof, and a full gutter system. Enjoy the private courtyard, perfect for relaxing or entertaining. Oakland Trails offers scenic walking and biking trails, a community pool, clubhouse, dog park, beautifully maintained common areas, and top-rated schools. Historic Downtown Winter Garden, with its restaurants, breweries, boutiques, farmers market, and year-round events, is just minutes away. The property is well suited for long-term rental investment. For buyers with pet-related allergies or sensitivities, it may be helpful to know that no pets have lived in the home during the current ownership. A detailed list of builder upgrades and owner improvements will be provided to prospective buyers. Quality construction, flexible living, and an exceptional location make this move-in-ready home an outstanding opportunity in one of Winter Garden's most sought-after communities.

2065 White Feather Loop, Oakland

$834,000
3 Beds 4 Baths Park Place/Winter Garden SubDv. 34787 Zip Code
131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable Park Place community in the heart of historic Winter Garden, Florida. This beautifully designed three-story home offers 3 bedrooms, 3.5 bathrooms, and 1,906 square feet of heated living space. Each bedroom features its own en-suite bathroom, providing privacy and comfort for all. This home includes an elevator that conveniently connects the first and second floors along with an oversized rear-entry two-car garage, a small balcony, and a convenient in-unit laundry closet. Inside, the open-concept main level boasts a gourmet kitchen with stainless steel appliances, a large island, and ample cabinetry. Premium finishes throughout include wood-look tile flooring, crown molding, and plantation shutters. The primary suite offers generous closet space and a spa-inspired bath with dual vanities, a soaker tub, and a walk-in shower. Thoughtful design and quality craftsmanship combine with a prime location just steps from downtown Winter Garden’s restaurants, shops, and the Plant Street Market, making this property an exceptional opportunity to enjoy upscale living in one of the area’s most sought-after neighborhoods.

131 Oak Laurel Drive, Winter Garden

$2,098,000
4 Beds 4 Baths Oakland Park SubDv. 34787 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!

1258 Ridge Lake Way, Oakland

$182,000
2 Beds 2 Baths Townhomes Winter Garden SubDv. 34787 Zip Code
Short Sale. SHORT SALE APPROVED READY TO CLOSE AND MOVE-IN READY and quietly positioned within a well-established Winter Garden community, this updated 2-bedroom, 2-bath condo offers a NEW ROOF, and an easy, comfortable lifestyle in one of Central Florida’s most desirable areas. Approaching the home, you’ll appreciate the tucked-away cul-de-sac location with paved private streets and sidewalks that create a calm, residential feel. Step inside through the front entrance and you’re immediately welcomed into a bright, open living space where natural light enhances the clean layout and efficient use of square footage. The living room feels inviting and functional, offering enough space to relax, entertain, or simply enjoy a quiet evening at home. Continuing through the home, the upgraded kitchen with GRANITE counter tops, anchors the main living area with modern appliances, ample cabinetry, and practical counter space. Its open connection to the living room allows for easy conversation while cooking, hosting, or enjoying everyday routines, making the space feel connected and intentional. The primary bedroom is set apart as a comfortable retreat, featuring brand-new carpeting and a private en-suite bathroom. The bathroom has been thoughtfully renovated with updated finishes that feel fresh and clean without excess. The secondary bedroom is well-sized and flexible, ideal for guests, a home office, or additional living space, with a second fully updated bathroom conveniently nearby. Throughout the condo, the layout flows efficiently from room to room, offering smart storage, comfortable proportions, and a low-maintenance design well suited for full-time living or long-term ownership. Assigned parking adds convenience, while the community’s shared amenities—including a COMMUNITY POOL—enhance the overall lifestyle. Located just minutes from downtown Winter Garden, residents enjoy close proximity to local shops, dining, farmers markets, and the West Orange Trail. Easy access to major highways makes commuting throughout Central Florida simple, whether heading toward downtown Orlando, major employment centers, or nearby attractions. This location is ideal for buyers exploring Orlando homes for sale or those planning an Orlando relocation home in a walkable, community-oriented area. While not intended as a short-term rental investment, this Winter Garden property represents a strong opportunity within the Central Florida real estate market for buyers seeking comfort, location, and value. Contact us today for a private tour or more details on this exceptional opportunity.

373 Eron Way Unit 47, Winter Garden

$1,200,000
4 Beds 3 Baths Winter Garden Shores Rep SubDv. 34787 Zip Code
PRICE ADJUSTED to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. This property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.

205 Surprise Drive, Winter Garden

$796,000
5 Beds 3 Baths Oakland Trls Ph 2 SubDv. 34787 Zip Code
Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE UPGRADES—creating a home that truly feels “better than new.” Step inside to an inviting OPEN-CONCEPT LAYOUT, where the chef’s kitchen overlooks the spacious living area. Recessed lighting, NEW TILE FLOORING on the main level (2023), and ceiling fans throughout (2020) elevate the home’s comfort and style. The entire home is also PREWIRED WITH CAT 6, ideal for high-speed connectivity. The DREAM KITCHEN is a showstopper with stylish cabinetry, stone countertops, a breakfast bar, built-in oven, cooktop stove with POT FILLER, tile backsplash, walk-in pantry, and a GALLEY-STYLE COFFEE BAR AREA—perfect for morning routines or entertaining. A spacious Kitchen dinette area overlooks the backyard, adding a warm and functional touch to the heart of the home. In the Living room, enjoy a CUSTOM ACCENT WALL (2023) and views of the large backyard through dual sliding glass doors. A separate Dining room offers flexibility for family gatherings or can easily serve as a formal living room. The first floor also includes a VERSATILE OFFICE/PLAYROOM, convenient under-stair storage, and ONE OF THE FIVE BEDROOMS—complete with laminate wood flooring—located next to a full bathroom, providing a perfect space for guests or multigenerational living. Upstairs, a GENEROUS LOFT creates a perfect secondary living area. The UPDATED PRIMARY SUITE (2025) features a beautiful tray ceiling, a LUXURIOUS EN SUITE BATH with dual vanities, a step-in shower, and a huge walk-in closet. Three additional bedrooms and another full bath offer plenty of comfortable space for family and guests. A paver driveway leads to the generous 3-CAR GARAGE featuring epoxy flooring, additional kitchen-style cabinetry, and PREWIRING for an electric vehicle. Outside, enjoy a large covered patio and an EXPANSIVE BACKYARD, ideal for future customization, gatherings, or play. Oakland Trails is loved for its peaceful setting and small-town charm, offering access to the West Orange Trail, playgrounds, green spaces, and TOP-RATED SCHOOLS. Ideally positioned near DOWNTOWN WINTER GARDEN, residents enjoy quaint dining and gatherings spots, PLANT STREET MARKET, charming shops, and easy access to SR 429 for seamless commuting. Every detail has been thoughtfully crafted for ELEVATED LIVING—come experience the exceptional quality and SOPHISTICATION this home offers. Schedule your showing today!

1970 Standing Rock Circle, Oakland

$2,310,600
5 Beds 6 Baths Grove At The Harvest District SubDv. 34787 Zip Code
Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floor plan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Heath Stone also features a 2-car detached garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Hearth Stone model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.

1146 Prado Lane, Oakland

$2,380,160
5 Beds 6 Baths Grove At The Harvest District SubDv. 34787 Zip Code
Pre-Construction. To be built. Introducing the Sunburst Model by Davila Homes Discover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floorplan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Sunburst also features a 3-car garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Upstairs, enjoy a stunning covered terrace, ideal for morning coffee, evening gatherings, or simply taking in the views of your surroundings. With its blend of functionality and sophistication, every space in the Sunburst is designed to make daily living both easy and elegant. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Sunburst model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.

1173 Prado Lane, Oakland

$1,599,000
4 Beds 4 Baths Lakeview Reserve 46/149 SubDv. 34787 Zip Code
COMPLETELY REMODELED WATERFRONT HOUSE WITH COVERED PRIVATE DOCK AND BOAT LIFT ON THE LARGEST LAKE IN CENTRAL FLORIDA!!! A highly energy-efficient house with owned solar panels ($30 monthly grid surcharge vs. $500-600 electric bill before). The cost of solar panels is included in the purchase price. The price can be reduced by $37K if the buyer assumes a solar panel loan at 3.49%. Experience the ultimate LAKEFRONT living with this stunning, COMPLETELY REMODELED HOUSE ($400K investment) on Lake Apopka in Winter Garden, in the heart of a highly desirable GOLF CART DISTRICT. Boasting over 3,700 sq. ft. of beautifully remodeled living space, this 4-bedroom, 3.5-bathroom residence combines modern luxury with waterfront charm. Every inch of this home has been meticulously upgraded, creating a move-in-ready oasis with high ceilings, open-concept living, designer lighting and upgraded finishes throughout. Gorgeous porcelain tile and hardwood floors flow seamlessly across two stories, complemented by abundant natural light from all-new, PANORAMIC WINDOWS. The gourmet kitchen is a chef’s dream, featuring quartz countertops, a large island with built-in cabinetry, stainless steel appliances, a backlit quartz bar, a wine fridge and a modern backsplash. Entertain effortlessly in the expansive high-ceiling dining room and living room, framing incredible LAKE APOPKA VIEWS, GORGEOUS SUNRISES AND BREATHTAKING SUNSETS! The spacious master suite on the ground floor is a serene retreat with a high ceiling, two walk-in closets, an oversized bathroom with two sinks, Jacuzzi and a massage shower and a private screened patio. Two additional bedrooms on the ground floor boast lake views, California closets and high ceilings. A second-floor oversized loft offers a full bathroom, a walk-in closet, separate HVAC and noise-reducing flooring and window treatment —perfect for another master bedroom or entertainment room. Two Florida rooms on both floors provide stunning panoramic lake views. A dedicated office/den on the ground floor is ideal for work or study. All bathrooms have windows and exhaust. Enjoy 90 feet of open-view waterfront—perfect for skiing, boating, fishing, or relaxing. The oversized COVERED BOAT DOCK has electric BOAT LIFT, lighting, WATER, and a Margaritaville-themed bar. The backyard features a RECENTLY RESURFACED SALTWATER POOL with a NEW PUMP, NEW POOL FILTER, a REFENCED PRIVATE YARD, fruit trees & mature, landscaped greenery. Additional highlights include NEW WINDOWS, HVAC, SOLAR PANELS, SMART THERMOSTAT, upgraded irrigation and landscaping, a TWO-CAR GARAGE with a lot of built-in storage and an OVERSIZED DRIVEWAY to park multiple boats or vehicles. Located in a quiet, family-friendly GATED COMMUNITY with golf-cart-friendly streets and DIRECT ACCESS to the scenic WEST ORANGE TRAIL and high-rated elementary and middle SCHOOLS NEARBY. Enjoy Winter Garden’s historic downtown just minutes away, with A-rated schools, shopping, dining, and the farmer's market. Only 20 minutes to Downtown Orlando and close to Disney, Universal, and major highways. There are 6 highly rated Golf Clubs within a 5-mile radius. This is more than a home—it’s a boater’s and fisherman’s paradise, a lakefront retreat, and a perfect family haven all in one. Don’t miss this rare opportunity to own a completely remodeled luxury waterfront home with unmatched views and lifestyle amenities on Lake Apopka, offering over 30,000 acres of endless water fun!

261 Zachary Wade Street, Winter Garden

$1,499,999
4 Beds 3 Baths J L Dillard Sub 3 SubDv. 34787 Zip Code
Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

241 N Dillard Street, Winter Garden

$575,000
Briley Farm SubDv. 34787 Zip Code
Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room—airy yet cozy and ready for your personal touch. Enjoy the perfect balance of indoor and outdoor living, set against serene scenery while remaining close to shopping, restaurants, and major highways. Briley Farm offers comfortable countryside living under a canopy of welcoming trees, crafted to embody the lifestyle you’ve been searching for. Stop by our sales office today to start building your dream home with Pioneer Builders!

514 N Pollard Street, Oakland