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$1,249,000
5 Beds 4 Baths Avalon Estates SubDv. 34787 Zip Code
Welcome to your very own slice of Winter Garden paradise! This impressive 5.3-acre, high-and-dry property is fully fenced, offers no HOA, and is ready for its next owner. The custom-built 2003 ranch-style home now features a brand-new roof, new windows, and 2025 spray foam insulation, offering enhanced comfort, efficiency, and peace of mind. Property features high end solar panels that all set your electric bill substantially. The electric bill prior to the solar panel is $1100 per month, but after it reduce the payment. Buyer will need to assume the existing solar lease. A 3-car garage, a spacious circular driveway, and a massive covered lanai—complete with a sparkling pool and relaxing jacuzzi—set the tone for luxury living. Inside, you’ll find four full bedrooms, four full bathrooms, a dedicated movie room, a wet bar, and a desirable split floor plan. The property also provides the opportunity to construct an additional structure—whether for a second residence, barn, stable, or garage with heated living space. Stylish ceiling fans and updated light fixtures add a refined touch throughout. The luxurious primary suite features direct access to the covered lanai, creating seamless indoor-outdoor living. Step outside to enjoy your private pool area, enhanced by retractable screen shades that offer extra comfort and make the patio ideal for both relaxing and entertaining. This exceptional estate combines luxury, sustainability, and expansive space in a beautifully updated environment. Don’t miss your chance to own this remarkable Winter Garden property—a true gem offering the perfect blend of serenity, modern convenience, newly upgraded features, and the freedom of no HOA.

17117 Heartwood Loop, Winter Garden

$652,316
4 Beds 4 Baths Harvest At Ovation SubDv. 34787 Zip Code
Welcome to this beautiful move-in ready home located in the desirable community of Summerlake in Winter Garden! This spacious property features an open-concept floor plan with abundant natural light, modern finishes, and a thoughtfully designed layout perfect for both everyday living and entertaining. The kitchen offers stainless steel appliances, granite countertops, and a large island overlooking the living and dining areas. Upstairs, you’ll find generously sized bedrooms, including a comfortable primary suite with a walk-in closet and an en-suite bathroom. Enjoy Florida living with a private backyard and access to resort-style community amenities such as a pool, fitness center, clubhouse, tennis courts, and playgrounds. Conveniently located near top-rated schools, shopping, dining, and major highways. Don’t miss this opportunity to own a beautiful home in one of Winter Garden’s most sought-after neighborhoods!

16108 Honey Harvest St, Oakland

$1,240,000
4 Beds 3 Baths Acreage SubDv. 34787 Zip Code
SUBSTANTIAL PRICE ADJUSTMENT on this special property, in Winter Garden, but just inside Lake County! For a champion equestrian, home is more than four walls, it’s land that performs, space that protects your horses, and a setting that allows you to train, restore, and win.Tucked away in a quiet corner of Winter Garden, yet located in Lake County for lower taxes, this rare brick estate delivers exactly that balance. Privacy when you need it. Convenience when you want it. Properties like this don’t come along often. The heart of the estate is the oversized barn, designed with intention and function: aluminum siding, a durable metal roof, six 12x12 stalls with running water, feeding stations, and a dedicated tack room that keeps everything organized and competition-ready. The fully fenced acreage is thoughtfully divided, giving your horses room to move while maintaining safety and control. A separate utility building: currently serving as an aviary adds flexibility for training, storage, or future pursuits. Mature fruit trees enhance the landscape, reinforcing the feeling of a working yet beautiful agricultural retreat. Inside, the home reflects the same balance of strength and refinement. The renovated kitchen is a showpiece, featuring GE Café appliances, waterfall-edge granite countertops, and modern floating shelves, perfect for gathering after long days in the saddle. The expansive 17x21 family room, with soaring 19-foot ceilings, creates a dramatic yet inviting space, while the freshly updated dining room adds polish with new paint and trim. Upstairs, a versatile loft can easily become a fifth bedroom, and the oversized bonus room (13x31) offers endless possibilities: gym, media room, or additional living space and complete with full-length storage. Each secondary bedroom includes its own private sink, connected by a Jack-and-Jill bath, with thoughtful reading lights for quiet moments of rest. Finished with a newly installed epoxy garage floor, every detail of this home has been carefully considered. This is where championship-level function meets everyday comfort. Just minutes from Winter Garden’s restaurants, shopping, and hospitals yet worlds away when you return home, this five-acre agricultural retreat offers the tranquility, space, and prestige of true country living. Not just a home. A lifestyle built for those who compete and expect more.

11714 Flynn Court, Winter Garden

$1,100,000
34787 Zip Code
BUILD YOUR CUSTOM RETREAT!! Discover an exceptional opportunity in the highly desirable Winter Garden area. This rare offering includes a 3.59-acre elevated homesite showcasing unobstructed, sweeping views of Black Lake, paired with a separate lakefront parcel. Both parcels are sold together, providing unmatched flexibility for your dream estate. The main parcel offers a stunning natural backdrop for a luxury custom residence, guest house, private garden, or personal retreat, all set against breathtaking lake views from morning to sunset. The bonus lakefront parcel allows you to design your own waterfront amenities, such as a private dock, pavilion, boat launch, or tranquil lakeside sitting area just steps from your home. Nestled in a peaceful, established setting with convenient access to Winter Garden’s premier dining, shopping, top-rated schools, and major highways, this property represents a truly unique opportunity to secure a generational lake-view estate in one of Central Florida’s most sought-after communities. Whether you envision a signature custom home, a multi-parcel compound, or a premium investment in West Orange County, this offering delivers an unparalleled blend of land, location, and lifestyle. Both parcels sold together. Rare opportunity, don’t miss your chance.

14424 Ellerbee Street, Winter Garden

$743,148
3 Beds 3 Baths Vinings Add Winter Garden SubDv. 34787 Zip Code
Experience the perfect blend of historic charm and modern comfort in this home nestled in the sought-after golf cart district of Downtown Winter Garden. This residence captures the character of the hip historic neighborhood while offering the convenience and style of newer construction. Step instide to find an open floor plan featuring high ceilings with elegant crown molding, cermamic tile, luxury laminate flooring, and solid surface countertops thoughout. With 3 bedrooms and 2.5 bathrooms, the layout is both functional and flexible. The first floor features the primary bedroom with an on suite bathroom and seperate office that provides an ideal workspace. For convenience it has a built out laundry room and tankless water heater for energy efficiant living. While the second floor houses the additional bedrooms with a loft that offers the space for relaxation and recreation. Outdoor living is just as inviting. Enjoy morning coffee on the covered front porch, or unwind in the paved, fenced backyard complete with a built-in gazebo, perfect for entertaining. Conveniently located and a short distiance to Downtown Winter Garden's Plant Street and the picturesque Lake Apopka sunsets, this home offers a life-style that is both vibrant and relaxed. Don't miss this opportunity. Call for a showing appointment today.

417 S Main Street, Winter Garden

$687,000
5 Beds 4 Baths Waterleigh Ph 3b 3c & 3d SubDv. 34787 Zip Code
Discover an incredible opportunity in Winter Garden. This spacious home offers five bedrooms and four full bathrooms, including a convenient first-floor bedroom perfect for guests or multigenerational living. Situated on a generous lot with no rear neighbors and a serene lake view, you’ll enjoy exceptional privacy and a beautiful natural setting. The property features a gourmet kitchen and modern vinyl flooring throughout the second floor, with no carpet. The community provides unmatched convenience with a Publix and schools located within the neighborhood, and you’ll also be just minutes away from shopping, dining, and major access roads. This is a special-priced home you don’t want to miss.

9374 Bolero Road, Winter Garden

$482,000
3 Beds 2 Baths Magnolia Wood Fifth Add SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Live your best downtown Winter Garden life in this updated, no-HOA home that perfectly blends comfort, character, and modern vibes. This 3-bedroom, 2-bathroom gem has all the big stuff done for you-new roof, new AC, new windows, and upgraded piping-so you can move right in and start enjoying the good life. The split floor plan gives everyone their own space, and the wood-burning fireplace brings the perfect cozy touch for movie nights or chill weekends. Need a little extra room? The bonus den, office, playroom, or sunroom (yes, it's under air!) gives you options-whether you're working from home, gaming, or just want a bright spot to relax with your coffee. Put back, you'll find a huge fenced yard with fruit trees, a garden bed, and plenty of room to host friends or hang out with pets. The sunsets are seriously next level, with peaceful partial views of Lake Apopka setting the mood. Tucked in a quiet neighborhood just minutes from Plant Street's restaurants, shops, and weekend farmers market, this home gives you all the downtown Winter Garden charm without any HOA drama.

1436 Coluso Drive, Winter Garden

$849,000
4 Beds 2 Baths Hull Island At Oakland SubDv. 34787 Zip Code
Discover a rare opportunity to own a private estate property in one of West Orange County’s most desirable corridors. Situated in Oakland, this 2.55-acre parcel offers space, privacy, and future potential just minutes from the conveniences of West Colonial Drive, Florida Turnpike (Exit 275), Clermont, and the vibrant districts of Oakland and Downtown Winter Garden. Properties like this are increasingly difficult to find. The home sits in an unincorporated area, giving flexibility and freedom while still being close to everything that makes this area so special. Walk or bike to the West Orange Trail, enjoy easy access to local parks, and connect quickly to shopping, dining, and major commuter routes. The residence offers approximately 2,700 square feet of living space and has been thoughtfully maintained in its original 1983 character, making it ideal for buyers seeking land, privacy, and the opportunity to personalize or modernize over time. Inside, you’ll find an open floor plan with soaring vaulted ceilings and large picture windows that fill the home with natural light. A dramatic floor to ceiling stone fireplace anchors the main living area and creates a warm focal point for gatherings or quiet evenings at home. The kitchen is spacious and functional, featuring abundant cabinetry, a large center island, built in appliances, and generous room for entertaining and everyday living. A large enclosed sunroom extends the living space and offers endless possibilities for a game room, fitness studio, home office, or year round relaxation overlooking the backyard. The home includes four generously sized bedrooms and two full bathrooms, all preserving their original charm and offering a strong foundation for updates, renovation, or a curated vintage aesthetic. Step outside and the true value of this property becomes clear. The 2.55 acres provide room for gardens, animals, workshops, RV and boat storage, or the creation of a private retreat. A detached casita adds flexibility for guests, extended family, a home office, or potential future income use. The property operates on a private well and septic system, offering independence, lower utility costs, and a rural lifestyle feel without sacrificing proximity to major roads, downtown Winter Garden, and the growing Oakland corridor. A unique blend of land, location, and opportunity this is a property where you can create, expand, and invest in a lifestyle that is increasingly rare in Central Florida.

624 Hull Island Drive, Oakland

$550,000
3 Beds 2 Baths Fries Winter Garden SubDv. 34787 Zip Code
Located in the heart of Historic Downtown Winter Garden…golf cart district! Walkable to amazing restaurants, boutiques, breweries, splash pad, Saturday Farmer’s Market or one of the many specialty events held throughout the year! This darling 1930’s craftsman bungalow had a complete restoration in 2017 and is still in mint condition! All the vintage charm without all the headaches! Spaces were thoughtfully reconfigured, new energy efficient windows were installed, a tankless gas hot water heater, electrical updates including a new panel and plumbing update from cast iron to PVC. Also, NEW HVAC in 2025! Now, let’s take a tour! Imagine a nostalgic brick walk way leads to the prettiest shade of vintage blue door, tidy landscaping and crisp wood work frame the picture. As the door opens, your eyes are drawn upward to the sparkling chandelier casting prismatic light across the vaulted ceilings. Raising the ceilings was part of the restoration and such a good choice! The natural light in the home is also quite nice. This space would be great as a family room or formal sitting area. Double doors open to a sunroom/ private office that would also make a fantastic playroom. The kitchen update included new appliances, including a gas range! Attractive gray shaker wood cabinets & white quartz countertops seem timeless, not trendy in this historic style. Another nice feature is having the kitchen and eating area in the center of the home, not closed off like many homes of this era. A stackable washer and dryer is also centrally located making laundry a breeze! The great room stretches across the back of the house with a bay window and wood beam accents. A spacious and relaxing place to admire the lush fenced backyard, tree canopy and fun macramé swing. The authentic vintage shed, paver patio and large level yard is the perfect back drop for BBQ’s and parties! At night, you’ll love the bistro lighting that gives the entire space a glow! After a fun evening of entertaining, retire to one of the three cozy bedrooms. Ensuite and spare baths are both ones you’d “PIN” as favorites with stunning tile work, ornate mirrors and funky shabby chic vanities! Little fact…The center bedroom lost the closet in the remodel, however there’s room for an armoire or space saving Ikea closet! Winter Garden is a suburb of Orlando that embraces modern luxuries with old world charm. A place to put roots down and stay forever!

315 S Boyd Street, Winter Garden

$1,910,500
5 Beds 7 Baths Avalon Estates SubDv. 34787 Zip Code
Discover Winter Garden’s best-kept secret in Avalon Estates, a peaceful, horse-friendly enclave where timeless country charm meets modern luxury. This custom-built residence offers an impressive 6,400 sq. ft. under air and nearly 10,000 sq. ft. under roof, set on 4.6 picturesque acres surrounded by nature and serenity. From the moment you arrive, the inviting curb appeal and sprawling front porch set the tone for what awaits inside. Step through the double entry doors into a grand living space filled with soaring ceilings, abundant natural light, and an airy, open feel that defines Florida living at its finest. The modern farmhouse kitchen is a dream for entertaining, featuring two expansive islands, generous counter space, and seamless flow into the family room, where a wood-burning fireplace adds warmth and charm. French doors open to the pool area, complete with two oversized covered lanais, creating an ideal setting for relaxing or hosting guests. The downstairs primary suite is both spacious and inviting, featuring a private fireplace, large walk-in closet, and a magazine-worthy en suite bath. A private office sits just off the primary suite, offering a quiet retreat for work or study. Upstairs, you’ll find a large bonus room with kitchenette, three additional bedrooms, and two full bathrooms—perfect for family or guests. Don’t miss the panoramic views through the large windows—on clear nights, you can watch Disney fireworks sparkle in the distance and even catch NASA rocket launches from the east coast. Built with poured concrete tilt-wall construction, this home is as strong and resilient as it is beautiful. The laundry room doubles as a safe room, featuring metal doors, bullet-resistant glass, and reinforced concrete walls and ceiling. Additional highlights include a new roof (2025), an attached three-car garage, plus a detached 2.5-car garage with studio and full bath—ideal for guest quarters, an office, or hobby space. Located just minutes from shopping, dining, and major highways (Florida Turnpike, 429, and 408), this estate is 11 miles from Disney World, 12 miles from Universal Studios, and 23 miles from Orlando International Airport. With its combination of space, craftsmanship, and location, this property also offers excellent potential as a luxury short-term rental. Experience the tranquility and grandeur of Avalon Estates—schedule your private tour today and start creating lifelong memories in your new home.

17261 Heartwood Loop, Winter Garden

$750,000
5 Beds 4 Baths Fries Survey Of Winter Garden SubDv. 34787 Zip Code
Welcome to 410 S Main Street — where small-town charm meets modern living in the heart of downtown Winter Garden’s historic golf cart district. Built in 2020, this single-story ranch rests on a fully fenced **.32-acre lot**, offering both privacy and potential just steps from the vibrant energy of Plant Street. Step through the front door and imagine the possibilities. With a little paint, drywall love, and your personal touch, this home is ready to shine. The split floor plan was designed for comfort and connection, open, airy living spaces flow naturally into a chef-inspired eat-in kitchen featuring a massive center island, gas cooktop, wine fridge, and a walk-in pantry that’s ready for every grocery run. A tucked-away workspace within the kitchen makes multitasking easy, while a nearby homework desk area keeps everyone organized. The owners’ retreat is your private escape, complete with French doors that open to a covered patio overlooking the spacious backyard — perfect for morning coffee or evening unwinding. Inside, you’ll find dual sinks, a large walk-in shower, and a comfortable walk-in closet for everyday ease. A courtyard-style 3-car garage offers generous storage, a deep freeze, and pull-down attic stairs leading to floored attic space for those extras. Two tankless water heaters ensure endless comfort and efficiency. Bring your golf cart, imagination, and love for Winter Garden’s walkable lifestyle — you’re just moments away from boutique shops, farmers markets, award-winning restaurants, and the West Orange Trail. 410 S Main Street isn’t just a house — it’s a story ready for its next chapter.

410 S Main Street, Winter Garden

$465,000
4 Beds 3 Baths Showalter Park SubDv. 34787 Zip Code
Discover the best of community and convenience at 275 Virginia Drive! This charming, mid-century gem created treasured memories for the same owners since 1955. A perfect blend of vintage character with some fresh updates, this classic 4-bedroom, 2.5 bath ranch has been meticulously cared for and is move-in-ready, but could also present an ideal canvas for a designer’s brush. Situated on a quiet street in the golf cart district of downtown Winter Garden, this home has the benefit of being closely located to the vibrant downtown area where top-rated dining, trendy shops, and the weekly farmer’s market await. For even more recreation, the West Orange Trail is one block away for jogging and biking, or take a quick golf cart ride to appreciate the serenity of Lake Apopka. Beyond a front entrance showcasing the original owner’s beveled-glass artistry, natural light from a large picture window enhances the vintage hardwood floors and neutral colors flowing throughout the living room and secondary bedrooms. An efficient kitchen features a cozy breakfast nook adjacent to the combined great room and dining area; an ample, open space for entertainment and holiday gatherings with loved ones. The separate, primary bedroom is generous, boasting a private entrance and a full, tiled bath. The roof, HVAC, and some plumbing fixtures were replaced within the last few years and in August 2025, a new and upgraded electrical system was installed. Outside, a handy sprinkler-system helps keep the sunny front yard lush while the backyard is surrounded by mature trees and shrubbery, making it a perfect spot for little ones and four-legged friends to roam freely without worry, as well as cookouts, or just outdoor relaxation in the warm Florida weather. Creative folks will spend countless hours in the custom workshop situated on its own concrete slab, and complete with attic storage and window A/C. This shed could easily be insulated and upgraded to create a comfortable space for a hobby area, man cave or anything else to suit your needs! This charming home is brimming with nostalgia and is ready and waiting to be your new forever home. Don’t miss your chance to own a piece of Winter Garden history, schedule a private showing TODAY!!!

275 Virginia Drive, Winter Garden

$650,000
3 Beds 2 Baths Glenview Estates 2nd Add SubDv. 34787 Zip Code
This stunningly updated 3 bedrooms, plus an office/den 2-bathroom residence blends contemporary design with warm, inviting charm. Nestled in a golf cart-friendly area of Winter Garden with no HOA, it offers both convenience and freedom. The open and split concept layout offers lots of privacy with the master located on the left side of the house offering two separate walk-in- closets and a separate ac unit. The 2nd and third beds are located on the right side of the house and a completely renovated 2nd bath. The living and dining room are open to the kitchen and are bathed in natural light, highlighting neutral walls colors and neutral tile wood planks floorings beautifully contrasted by sleek golden hardware and accents for a modern yet cozy vibe and as a final touch a wood burning fireplace. Vaulted cathedral ceilings amplify the spaciousness, and brand-new luxury tile planks flooring throughout the house. The kitchen is a true centerpiece, boasting newer stainless-steel appliances, soft-close custom-made cabinetry, and a striking stone backsplash and pot filler. A chef dreams gas range. A generously oversized quarts island provides ample storage, expansive prep space, and seating — perfect for entertaining or everyday family life. Recent upgrades include a 2023 roof, gutters and fully paid solar panels. A newer energy efficient water heater, ensuring comfort and peace of mind for years to come. Step outside to enjoy a large, fully fenced backyard featuring a 2023 heated new pool and hot tub, with extended open patio and a 2023 new covered summer kitchen with a bar and seating area — an ideal spot to relax and enjoy the outdoors grilling, drinking and entertaining family and friends. The backyard also offers a 28X12 carport, ideal for your RV parking, and a 12X10 shed built in 2022. The extended driveway is the perfect parking for those large trucks and SUV and golf cart as well. The location is unbeatable: just minutes from Winter Garden Village’s shopping, dining, and entertainment, and a short drive to the lively Plant Street Market. Lake Apopka is also nearby, offering scenic trails, water activities, and tranquil views. Don’t miss your chance to own this beautifully renovated gem in one of Winter Garden’s most desirable neighborhoods. Schedule your showing today and make this dream home yours!

963 Glenview Circle, Winter Garden

$280,000
3 Beds 2 Baths Bay St Park SubDv. 34787 Zip Code
This beautifully updated 3 bedroom, 2 bathroom home offers modern comfort at an unbeatable value. With 910 sq ft of living space, it features a brand-new roof, newer A/C, fresh interior and exterior paint, a fully remodeled kitchen with brand new appliances, and brand new remodeled bathrooms—giving you peace of mind and a move-in ready lifestyle. Located in the heart of Winter Garden, this home is close to shops, dining, and entertainment, all while being tucked into a welcoming neighborhood. Whether you’re a first-time buyer, downsizing, or looking for an investment property, this gem checks all the boxes. Don’t miss this rare opportunity to own a beautifully renovated home in one of Central Florida’s most sought-after communities—for less than $300K! All measurements are estimates**

1065 Lincoln Terrace, Winter Garden

$119,000
Mary Jean Sub SubDv. 34787 Zip Code
Build your dream home or investment property! Owner is willing to turn over the plans for a single family home for you to start the project right away and potentially saving you thousands. Quiet street with lots of mature oak trees and new construction in the area. 5 min from the iconic downtown Winter Garden, 3 minutes away from gorgeous Lake Apopka, and less than a mile from the 429. You will enjoy super convenient access to SR 429, SR 50, Florida's Turnpike, and the SR 408. Disney, Universal, downtown Orlando, and the Orlando Eye are easy drives. The neighborhood is not part of an HOA, so no annual association fees are due. Public Water/Sewer/Electric connections are available. Don't miss this opportunity. Make an offer now!

188 Mary Street, Winter Garden