34787 Zip Code FL Real Estate, Homes with No HOA Fee for Sale

2 Beds ⋅ 1 Baths ⋅ Westchester Place SubDv. ⋅ 34787 Zip Code

Charming bungalow that's been completely renovated and is now move-in ready! Rebuilt down to the studs in 2022, with all-new systems and finishes, new roof, electrical, plumbing, central HVAC, flooring and appliances, makes it a very solid investment—whether as a starter home or potentially as a bed-and-breakfast (B&B) option. With two bedrooms and one bath, this bungalow would make for a cozy and functional space. The inside laundry is a great modern convenience, and a breakfast bar is perfect for casual meals. Walking distance to Plant Street the vibrant downtown area of Winter Garden, known for its historic charm and many local businesses. You will enjoy access to the popular indoor artisan food hall, a craft brewery, restaurants, and shops. Outdoor enthusiasts will love being close to West Orange bike trail and Veterans Memorial Park. It is a 2 minute walk to Colonial and Hyde Park bus stop.

634 Foster Avenue, Winter Garden

$595,000

4 Beds ⋅ 4 Baths ⋅ Mcallister Lndg SubDv. ⋅ 34787 Zip Code

MCALLISTER LANDING 96/92 LOT 83

693 Caterpillar Run, Winter Garden

$639,658

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

Info Only - Chapin by Ashton Woods.

17603 Japonica Bloom, Winter Garden

$645,954

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

Info Only - Chapin by Ashton Woods.

17579 Japonica Bloom Drive, Winter Garden

$673,392

4 Beds ⋅ 4 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code

SOLD - Data entry only

15591 Gentle Rain Drive, Winter Garden

$665,000

3 Beds ⋅ 2 Baths ⋅ 34787 Zip Code

Beautiful lake front home with 340 feet of direct John's Lake frontage, sitting on over 4 acres of land. Property is directly adjoining the Scrub Jay Point Preserve for ultimate privacy, walking trails, and surrounded by nature. Home has a dock, pool, and fireplace, as well as a 4 car garage. A must see estate.

Winter Garden

$419,990

3 Beds ⋅ 3 Baths ⋅ Serenade/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Under Construction. Sample Images SAGE Townhome offers 3 Bedrooms, 2.5 Baths with a large open first floor. Lot 39 Ready Winter 2024 (Pre-Design Center Pricing) Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando, where Dream Finders Homes proudly presents Serenade at Ovation. Nestled amidst picturesque lakes and pristine conservation areas, our collection of award-winning single-family homes and contemporary townhomes beckons you. Embracing the essence of classic Florida architectural styles, each residence seamlessly blends indoor and outdoor living. Enrich your life with Winter Garden's local history and charm, while relishing easy access to top-tier schools, Orlando's business hubs, delectable dining, iconic attractions, and endless entertainment. Whether indulging in nearby theme parks or exploring local shopping, your options are limitless. Within the community, relish leisurely walks to the pavilion, let the little ones thrive at the tot lot, bask in the sun-drenched community clubhouse, and embrace tranquil evenings under the starlit sky. At Serenade at Ovation, a meticulously crafted home designed by experts eagerly awaits, ready to cocoon your cherished memories within the embrace of Florida living.

13235 Calming Breeze Way, Winter Garden

$445,986

3 Beds ⋅ 3 Baths ⋅ Northlake Townhomes SubDv. ⋅ 34787 Zip Code

Stunning townhome with the Regina II floor plan from Ashton Woods! Located just 10 minutes from Disney World.

17508 Northlake Grove Drive, Winter Garden

$553,963

3 Beds ⋅ 2 Baths ⋅ Northlake At Ovation Phase 2 & 3 SubDv. ⋅ 34787 Zip Code

New Construction

11377 Pixie Mandarin, Winter Garden

$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

$460,252

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

Ashton Woods new construction townhome. Great Horizon West community. Upgrades include luxury vinyl flooring on 1st floor, quartz countertops, stainless steel appliances, and more.

17693 Japonica Bloom Drive, Winter Garden

$510,000

4 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve At Hamlin Phase 2 SubDv. ⋅ 34787 Zip Code

Brand new, energy-efficient home ready NOW! Dry pond in backyard. The open first floor boasts a spacious great room and dining area that flow seamlessly together. The upstairs primary suite features an oversized walk-in closet, dual sinks, and a standing shower. Now selling from the mid $500's, Silverleaf Reserve offers spacious open floorplan concepts fit for every lifestyle. Located in the heart of Winter Garden, you'll have easy access to eateries and entertainment alike. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

16394 Silver Brook Way, 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

$509,000

3 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code

Enjoy this beautiful brand new 3 Beds 2.5 baths with 2 car garage + loft up stairs. Amazing location, close to markets, restaurants and highway. Near Disney and perfect for your family! Located in a friendly neighborhood, this single family offers comfort and convenience in a prime location. Top-rated schools inside the community. Shopping centers, and dining options, and just minutes from Disney. Easy to apply!!! Schedule a visit, you will love it! Enjoy this community with pool, pickleball court, playground and enjoy all life style Winter Garden / Horizon West provide.

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

$839,541

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

Data Entry Only

11081 Hollow Bay Drive, Winter Garden

$995,610

4 Beds ⋅ 3 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

Sold. New construction

210 Woodfall Lane, Winter Garden

$400,000

Overstreet Crate SubDv. ⋅ 34787 Zip Code

Winter Garden 2 lots surrounded by commercial/industrial properties. Close to Highway 50, the Turnpike, and SR 429.

12325 & 12303 Stagg Road, Winter Garden

$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

$470,000

Park Sub SubDv. ⋅ 34787 Zip Code

Prime commercial lot in the heart of Winter Garden. 0.30-acre site with approved architectural, structural, and engineering plans for a 2,250 SF retail/office shell under the 2023 Florida Building Code. Zoned R-NC (Neighborhood Center), ideal for medical, office, or professional use. Permit-ready site with city water and sewer available. Excellent visibility and access from W Story Rd, minutes from Downtown Winter Garden. Save 9–12 months of design and permitting time—ready to build now.

244 W Story Road, Winter Garden

$796,191

4 Beds ⋅ 4 Baths ⋅ Waterleigh Phase 5 SubDv. ⋅ 34787 Zip Code

NEW CONSTRUCTION HOME

16140 Point Rock Drive, 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

$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

$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

$696,307

4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code

Step inside and find a beautiful 4 bedroom and 5 bathroom home with a formal dining room which flows seamlessly into the family room, kitchen, and casual dining area, creating a welcoming space for everyday moments and special occasions.

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

$768,390

4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation Phase SubDv. ⋅ 34787 Zip Code

Great investment opportunity

16107 Honey Harvest Street, Winter Garden

$819,006

4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation Phase 2 SubDv. ⋅ 34787 Zip Code

Great investment opportunity

16125 Honey Harvest Street, Winter Garden

$730,000

4 Beds ⋅ 4 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code

SDEO

13117 Faro Court, Winter Garden

$428,500

3 Beds ⋅ 3 Baths ⋅ Serenade/Ovation Ph 1 SubDv. ⋅ 34787 Zip Code

Sold Data entry Only

13217 Calming Breeze Way, Winter Garden

$214,000

2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 02 SubDv. ⋅ 34787 Zip Code

Come and see why this spacious 2 bedrooms, 2 bathrooms second floor open floor plan condo that is conveniently located only minutes to Winter Garden Historic Downtown, with easy access to cafés, boutique shops, a vibrant farmers market, shopping, dining, hospitals, and major roads, with quick access to Downtown Orlando, Universal, Disney, and the airport. A/C - July 2025, Fridge - April 2025, Dishwasher - May 2025 and second bathroom renovated February 2025. The well-maintained community includes lush landscaping, a pool, clubhouse, and basketball courts. A fantastic opportunity whether you’re looking for a starter home, retirement retreat, or rental investment!

68 Windtree Lane Unit 201, Winter Garden

$479,990

3 Beds ⋅ 2 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code

New Construction Single Family Home 3 bedroom 2 bathroom.

12615 Clear Sapphire Drive, Winter Garden

$542,071

4 Beds ⋅ 2 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code

Brand New Single Family Home 4 bedroom 2 bathroom.

12639 Clear Sapphire Drive, Winter Garden

$1,015,000

3 Beds ⋅ 3 Baths ⋅ Lake Avalon Heights SubDv. ⋅ 34787 Zip Code

Located in the Rare Lake Avalon Rural Settlement where oversized lots and protected rural zoning create one of Winter Garden’s last truly rare, low-density communities. Welcome to this fully remodeled, modern lakefront retreat on the shores of Lake Avalon, offering the perfect balance of sophistication, privacy, and convenience. Situated on almost 1.5 acres of fenced, irrigated land, this stunning single-story home features 3 bedrooms, 3.5 baths, and approximately 2,400 sq. ft. of living space with an attached 2-car garage—all meticulously updated with high-end finishes throughout. Step inside to an open, airy floor plan filled with natural light and luxury vinyl wood flooring that flows seamlessly from room to room. The gourmet kitchen is the heart of the home, featuring a dramatic quartz waterfall island, soft-close cabinetry, elegant gold accent hardware, and premium GE Cafe Matte white kitchen appliances, all included, along with washer and dryer. The kitchen overlooks a spacious dining area and family room, perfect for entertaining or relaxing by the wood-burning fireplace while taking in serene views of the backyard and lake beyond. The primary suite is a luxurious private retreat with two walk-in closets, direct access to the back porch, and a spa-style bathroom featuring double vanities, a beautifully tiled walk-in shower, and a freestanding soaking tub. The two additional bedrooms each have their own custom; modern bathrooms designed with premium tile and fixtures. Outside, the possibilities are endless. Enjoy the peaceful setting surrounded by mature trees, a large fire pit area, and a private pathway leading to your own dock—perfect for skiing, fishing, kayaking, or simply watching the sunset over Lake Avalon. Lake Avalon is a freshwater lake of about 184 acres in size and the lake supports fish species including largemouth bass and blue catfish. The property offers ample space for a boat, RV, or multiple vehicles along the extended paved driveway, with no HOA restrictions, allowing you the freedom to add a guest house, barn, or workshop if desired. Major updates include: Roof (2021), A/C (2021), Plumbing (2019), Water Heater (2020), Windows (2019), Septic (2019 and clean out 2025), Well Pump (2025), Water Softener & Purification System (2021). The home operates on well and septic, ensuring low utility costs and self-sufficiency. Located just minutes from Historic Downtown Winter Garden, Fowler’s Grove, and Hamlin Town Center, you’ll enjoy the best of both worlds—city conveniences with a peaceful, country feel. This home truly has it all: acreage, lake access, privacy, and luxurious modern design—all move-in ready for the holidays. There’s simply nothing else like it on the market. Come experience lakefront living at its finest in one of Central Florida’s most desirable locations. Call for your private tour today!

17661 Davenport Road, Winter Garden

$929,500

3 Beds ⋅ 2 Baths ⋅ Rolling Hills Avalon Annex SubDv. ⋅ 34787 Zip Code

This home in the rural community of Lake Avalon features a beautiful 2+ acre property with mature oaks with fresh landscaping, long paved driveway, and a separate workshop/barn or possible 6+ car garage with separate electric meter. A 3 bedroom 2 bathroom plus office with a large Florida room, gas burning fireplace, and large kitchen with wood cabinetry and center island which are all wonderful features of this country home. Brand new roof and newer AC with a freshly painted interior. This community features one of the best locations in the county with a rural feel yet close to amenities and easy commute routes. This community prides itself with rural protection from the county with an Agricultural zoning which allows small farming, horses and livestock, and opportunity for an ADU building approval. Schools in the area are top rated. Property is fully fenced with a smart gate opener and fully irrigated. Own your piece of Florida paradise!

17234 Cork Street, Winter Garden

$979,000

4 Beds ⋅ 3 Baths ⋅ Emerald Acres SubDv. ⋅ 34787 Zip Code

Welcome home to a true Winter Garden gem that perfectly blends modern comfort, timeless design, and small-town charm. Nestled on a spacious private lot with no HOA, this beautifully expanded and reimagined residence captures the spirit of historic Winter Garden while delivering every modern luxury. Step inside and feel the warmth of a home lovingly transformed from its original 3-bedroom ranch into a stunning 4-bedroom, 3-bath retreat spanning more than 3,300 sf. Every detail has been thoughtfully curated — from the chef-inspired kitchen to the inviting gathering spaces that make this home a haven for family life and entertaining. The kitchen is the heart of the home, featuring cashmere-white granite countertops, a 5-burner gas cooktop with high-velocity vent hood, pot filler, and a walk-in pantry with concrete counters. Dual full-size refrigerator and freezer units provide professional-grade storage, and the open design keeps everyone connected across the bar-top seating and living area. Multiple living and entertaining zones make this home truly special. Enjoy cozy evenings around the double-sided fireplace, host friends at the Tiki-bar porch (complete with built-in beer tap and refrigerator), or unwind on the two-level back deck featuring an outdoor kitchen, built-in hot tub, and paver patio with fire-pit wall — all set against a backdrop of breathtaking sunset views over the treetops. The home was designed to complement Winter Garden’s historic district, drawing inspiration from nearby vintage architecture and timeless details found throughout downtown. Brick column bases, tapered columns, and graceful arches pay homage to the area’s early 20th-century charm while interiors balance modern function with warmth and character. Skylights and a solar tube bathe the home in natural light, while thoughtful craftsmanship ensures every space feels welcoming. Enjoy your morning coffee on the front porch and wave to neighbors passing by — this is the kind of street where community still matters. The fenced backyard with a built-in dog door is ideal for pets and play, and there’s ample room to add a pool if you wish. Additional features include dedicated RV parking with power hookup, offering the perfect setup for your camper, boat, or extra vehicle — a rare find in this desirable location. Located in the highly coveted golf cart district of downtown Winter Garden, you’re just a five-minute golf cart ride from the heart of Plant Street — home to the Crooked Can Brewery & Marketplace, Axum Coffee, Plant Street Market, Matthew’s Steakhouse, and an ever-growing array of boutiques, cafés, and entertainment. Stroll or ride to the West Orange Trail, enjoy the Saturday Farmers Market, or take part in year-round events like Music Fest, Spring Fever in the Garden, and Oktoberfest. Every feature of this property reflects thoughtful living — from the expansive 0.33-acre lot on a quiet dead-end street to the custom addition adding over 1,800 square feet of living space, an expanded primary suite with spa-style bath, and multiple social zones perfect for entertaining. Abundant natural light pours through skylights and large windows, while the private backyard oasis offers serene sunset views and generous outdoor living space. This is more than a house — it’s a lifestyle. With space to grow, room to gather, and proximity to one of Florida’s most vibrant downtown districts, this Winter Garden treasure offers the perfect place to live, play, and thrive.

100 Temple Grove Drive, Winter Garden

$375,000

2 Beds ⋅ 1 Baths ⋅ Lake View Add SubDv. ⋅ 34787 Zip Code

Investor special or perfect project home just steps from historic Downtown Winter Garden! This 2-bedroom, 1-bath bungalow sits on a generous lot and offers tons of potential for renovation or redevelopment. Bring your vision to life—restore its original charm or reimagine the space entirely. The location can’t be beat—walk or bike to the West Orange Trail, popular shops, restaurants, and the weekly farmers market. With its prime downtown location and solid bones, 329 W Bay Street is a rare opportunity to create your dream home or next investment property in one of Central Florida’s most sought-after communities.

329 W Bay Street, Winter Garden

$1,260,826

5 Beds ⋅ 5 Baths ⋅ Oakland Pk Un 7 South SubDv. ⋅ 34787 Zip Code

new construction.

1143 Bulwark Oaks Lane, Oakland

$800,000

5 Beds ⋅ 5 Baths ⋅ Horizon Isle Llc SubDv. ⋅ 34787 Zip Code

Brand new K Hovnanian 5 bed/4.5 bath home in Winter Garden.

13159 Faro Court, Winter Garden

544 Walker, Oakland

5 Beds ⋅ 5 Baths ⋅ Oakland Pk Un 7 South SubDv. ⋅ 34787 Zip Code

new construction.

1143 Bulwark Oaks Lane, Oakland

$235,000

2 Beds ⋅ 1 Baths ⋅ Loveless & Sewell Add SubDv. ⋅ 34787 Zip Code

Great Opportunity for a solid home on a half acre lot. Two bedrooms with an open floor plan. Lots of upgrades. Near Downtown Winter Garden and all the cafes and shops on Historic Plant Street. Close to the 429, Florida Turnpike, the 408 and 15 minutes to Downtown Orlando. This one will not last. Call for more details.

364 N West Crown Point Road, Winter Garden

$470,690

4 Beds ⋅ 3 Baths ⋅ 34787 Zip Code

SDEO

Winter Garden

$150,001

G T Smith Sub 4 SubDv. ⋅ 34787 Zip Code

***PLEASE DO NOT GO SEE HOME WITHOUT AN APPOINTMENT APPROVED BY LISTING AGENT***** *****HIGHEST AND BEST OFFER DUE BY 900PM MONDAY 10/13/25... THANK YOU***** Prime Winter Garden Location – Investor special to renovate or build new! Welcome to 143 W Morgan Street in Winter Garden, Florida — a rare opportunity to own a piece of property in one of Central Florida’s most desirable communities. This 2-bedroom, 1-bathroom fixer upper offers 780 sq. ft. of living space on a generous .17-acre lot with no HOA — meaning no fees, no restrictions, and the freedom to truly make it your own. Built in 1940, this single-story residence sits in unincorporated Orange County and is zoned R-2, offering excellent versatility. You can renovate the existing home, or build new — either a single-family home or a modular residence with a permanent foundation. Setbacks are 25’ front and rear, 6’ sides, with a maximum building height of 35’. The lot meets the required 45’ minimum width for new construction, giving you flexibility for your future plans. The property features copper plumbing, city water, a septic system, and Duke Energy for electricity. Outdoor living is easy to enjoy with an oversized yard — perfect for gardening, play, or even raising up to four backyard chickens (no roosters; requires class and permit). You’re also allowed to store one boat and one RV onsite (though not for living purposes). Inside, the home is equipped with wall air-conditioning units and has a functional layout, but it is ready for major updates and vision. Whether you choose to restore it with TLC or start fresh with a new build, the potential is endless. Why Winter Garden? This area has become one of Central Florida’s most sought-after destinations. Known for its historic charm and small-town feel, Winter Garden offers a vibrant downtown with boutique shopping, award-winning dining, and the central Florida famous Winter Garden Farmers Market. The West Orange Trail runs right through town, inviting you to bike, jog, or stroll for miles. Recreation abounds with nearby lakes for boating and fishing, scenic parks, golf courses, and community events year-round. Disney World, Universal Studios, SeaWorld and Downtown Orlando are within 30 minutes. The Orlando International Airport is just as convenient, making travel a breeze. And in 90 minutes or less, you can enjoy Florida’s sandy east coast beaches or the stunning Gulf Coast. This property is truly about location, freedom, and opportunity. Whether you’re an investor, a builder, or a homeowner dreaming of a new start, 143 W Morgan St offers the perfect canvas in one of Florida’s fastest-growing and most beloved communities. Don’t miss this chance to create your vision in Winter Garden — schedule a showing today!

143 W Morgan Street, Winter Garden

$150,001

2 Beds ⋅ 1 Baths ⋅ G T Smith Sub 4 SubDv. ⋅ 34787 Zip Code

***PLEASE DO NOT GO SEE HOME WITHOUT AN APPOINTMENT APPROVED BY LISTING AGENT***** *****HIGHEST AND BEST OFFER DUE BY 900PM MONDAY 10/13/25... THANK YOU***** Prime Winter Garden Location – Investor special to renovate or build new! Welcome to 143 W Morgan Street in Winter Garden, Florida — a rare opportunity to own a piece of property in one of Central Florida’s most desirable communities. This 2-bedroom, 1-bathroom fixer upper offers 780 sq. ft. of living space on a generous .17-acre lot with no HOA — meaning no fees, no restrictions, and the freedom to truly make it your own. Built in 1940, this single-story residence sits in unincorporated Orange County and is zoned R-2, offering excellent versatility. You can renovate the existing home, or build new — either a single-family home or a modular residence with a permanent foundation. Setbacks are 25’ front and rear, 6’ sides, with a maximum building height of 35’. The lot meets the required 45’ minimum width for new construction, giving you flexibility for your future plans. The property features copper plumbing, city water, a septic system, and Duke Energy for electricity. Outdoor living is easy to enjoy with an oversized yard — perfect for gardening, play, or even raising up to four backyard chickens (no roosters; requires class and permit). You’re also allowed to store one boat and one RV onsite (though not for living purposes). Inside, the home is equipped with wall air-conditioning units and has a functional layout, but it is ready for major updates and vision. Whether you choose to restore it with TLC or start fresh with a new build, the potential is endless. Why Winter Garden? This area has become one of Central Florida’s most sought-after destinations. Known for its historic charm and small-town feel, Winter Garden offers a vibrant downtown with boutique shopping, award-winning dining, and the central Florida famous Winter Garden Farmers Market. The West Orange Trail runs right through town, inviting you to bike, jog, or stroll for miles. Recreation abounds with nearby lakes for boating and fishing, scenic parks, golf courses, and community events year-round. Disney World, Universal Studios, SeaWorld and Downtown Orlando are within 30 minutes. The Orlando International Airport is just as convenient, making travel a breeze. And in 90 minutes or less, you can enjoy Florida’s sandy east coast beaches or the stunning Gulf Coast. This property is truly about location, freedom, and opportunity. Whether you’re an investor, a builder, or a homeowner dreaming of a new start, 143 W Morgan St offers the perfect canvas in one of Florida’s fastest-growing and most beloved communities. Don’t miss this chance to create your vision in Winter Garden — schedule a showing today!

143 W Morgan Street, Winter Garden

$243,900

3 Beds ⋅ 1 Baths ⋅ Bay St Park SubDv. ⋅ 34787 Zip Code

**NOW FHA AVAILABLE** DISCOVER THE SERENE BEAUTY OF THIS STUNNING HOME! GORGEOUS 3-BEDROOM, 1-BATHROOM, 1-CARPORT HOME boasting a SPACIOUS FLOOR PLAN that effortlessly blends functionality with modern style. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. Cook like a pro in the NEWER KITCHEN featuring NEW QUARTZ COUNTERTOPS and SLEEK STAINLESS STEEL APPLIANCES—perfect for culinary enthusiasts. This home is LOADED WITH UPGRADES, including: New Roof with 30-Year Shingles, New HVAC System, New Laminate Flooring Throughout, Renovated Bathrooms, Fresh Interior & Exterior Paint, New Light Fixtures, Faucets, Toilets, Interior Doors, and Closet Doors. CONVENIENTLY LOCATED near all major highways, shopping, restaurants, and entertainment—this move-in-ready home truly has it all! All measurements are approximate and should be verified by the buyer for accuracy. Virtual Staging was added to some of the pictures.

1125 Lincoln Terrace, Winter Garden

$395,000

2 Beds ⋅ 1 Baths ⋅ Ellman Park SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Downtown Winter Garden charmer in the Golf Cart District—set on a picturesque brick street, this beautifully updated 2 bedroom, 1 bath home sits on an oversized 0.24-acre lot with approximately 75 feet of frontage. Substantially remodeled in 2019, it blends classic character with modern comfort and welcomes you with a wide front porch perfect for morning coffee and sunset chats. Inside, light-filled living spaces and a smart, flexible layout make the home live larger than its size, and the convenience of an interior laundry with washer and dryer located inside adds everyday ease. The deep backyard offers room to play, garden, entertain, or plan future enhancements. Zoned R-2 (Two-Family), the property also presents valuable flexibility in one of Winter Garden’s most coveted locations. From the driveway, you are minutes by cart, bike, or foot to Plant Street dining, coffee shops, boutiques, and the award-winning Saturday Farmers Market. Plant Street Market with Crooked Can Brewing, the West Orange Trail, and the historic Garden Theatre are all close by—park the car, grab the cart keys, and enjoy downtown living at its best.

18 W Vining Street, Winter Garden

$580,000

Mckeys Regal Woods SubDv. ⋅ 34787 Zip Code

Rare opportunity in Downtown Winter Garden! One acre of buildable land in the highly sought-after golf cart district—come build your dream home in the heart of it all

104 Regal Place Drive, Winter Garden

$907,610

5 Beds ⋅ 5 Baths ⋅ Silverleaf Oaks/Hamlin Ph 3a SubDv. ⋅ 34787 Zip Code

Scarlett Floorplan: 5bd + office, 4.5baths, 3 car garage.

6232 Argent Wood Drive, Winter Garden

$220,000

2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 05 SubDv. ⋅ 34787 Zip Code

Welcome to this move-in ready 2-bedroom, 2-bathroom located just minutes from historic downtown Winter Garden famous for its shopping, dining and regular entertainment. Enter to an open layout with natural light, new flooring, paint and updated kitchen. Enjoy a split-bedroom layout for added privacy. Spacious bedrooms with walk in closets and new flooring throughout. Windtree offers low maintenance living in a well-kept community with a pool and tennis courts with the added convenience of being just minutes from major highways

145 Windtree Lane Unit 145, Winter Garden

$883,656

4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation Phase 2 Pb 117/82 Lot 209 SubDv. ⋅ 34787 Zip Code

new construction

16089 Honey Harvest St, Winter Garden

$330,000

3 Beds ⋅ 2 Baths ⋅ Merchants Sub SubDv. ⋅ 34787 Zip Code

READY NOW! THE SELLER WILL CONTRIBUTE $ 5,000 TOWARDS CLOSING COST FOR THE BUYER. This spacious 3-bedroom, 2-bathroom home is perfect for anyone seeking modern comfort and style. Step inside and you'll immediately notice the open floorplan, which boasts plenty of natural light and provides ample space for entertaining. No HOA, one-story floorplans featured in Winter Garden, Florida. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,210 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. The kitchen features quartz countertops, stainless-steel appliances and a which are sure to both turn heads and make meal prep easy. You’ll never be too far from the action with the living and dining area right there. In every bedroom you’ll have tile floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom located in the rear of the home has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity. just minutes from the vibrant and historic Downtown Winter Garden.

823 Magnolia Avenue, Winter Garden

$625,000

4 Beds ⋅ 2 Baths ⋅ Glenview Estates SubDv. ⋅ 34787 Zip Code

*Spacious Family Retreat with Pool & Entertaining Space* Welcome to this large family home designed for both comfort and connection, perfectly set in a highly desirable golf cart community with no HOA, just 5 minutes from historic downtown Winter Garden. With its spacious layout, private pool, and beautifully landscaped backyard, this home offers the ideal blend of indoor elegance and outdoor living. Home as 2 AC units to keep you cool on those hot summer days. Also has 2 water heaters, one for each side of the house. Roof is just 3 years old. Step inside to discover an open and inviting floor plan filled with natural light. The separate office provides a quiet, dedicated space for remote work or study, while the large laundry room adds everyday convenience with room to spare. The heart of the home flows effortlessly into the backyard oasis—your very own retreat for relaxation and entertaining. Enjoy a refreshing swim in the private pool, gather with friends in the generous outdoor entertaining area, or simply take in the beauty of the yard designed for year-round enjoyment. Living here means more than just a beautiful home—you’ll be part of a welcoming golf cart community, where local shops, dining, weekend markets, and festivals in historic downtown Winter Garden are just a short ride away. This property offers the perfect balance of location, lifestyle, and space—a rare find in today’s market.

617 Glenview Drive, Winter Garden

$105,000

G T Smith Sub 4 SubDv. ⋅ 34787 Zip Code

R2 vacant land in downtown Winter Garden! This recently cleared lot, just outside the golf cart district is perfect for any investor. Located just minutes from 408, Turnpike, and 429. Don't hesitate, motivated seller, won't last long!

136 W Morgan Street, Winter Garden

$847,400

5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

Imperial model at Winter Grove by Pulte Homes. 5 bedrooms, 3.5 bathrooms and 2,631 sq ft.

264 Summer Pine Street, Winter Garden

$790,000

3 Beds ⋅ 3 Baths ⋅ Magnolia Wood SubDv. ⋅ 34787 Zip Code

Welcome to 1507 N Fullers Cross Road, a rare lakefront opportunity on Lake Apopka. This spacious three-bedroom, two-and-a-half-bath home sits on an impressive 1.12-acre lot with direct Lake Apopka frontage, offering privacy, tranquility and year-round sunset views. Surrounded by mature trees and natural wildlife, the property provides a peaceful lakefront retreat while remaining close to everything Winter Garden has to offer. Significant upgrades have been made, including a newer metal roof less than five years old, full re-plumbing, mostly completed new electrical rough-in, and fully paid-off solar panels. The home is being sold in unfinished condition, giving buyers a unique opportunity to complete the residence to their specifications and create a custom lakefront estate. Construction was started and then paused. Electrical and plumbing rough ins are mostly complete, with some finishing work needed. No drywall has been installed, leaving a clean slate for buyers to design and finish to their preferences. The seller will also convey valuable materials on site, including various cabinets, quartz countertops, bath fixtures, and kitchen appliances—saving buyers time and upfront costs. Whether you choose to complete the remodel, design a luxury lakefront retreat, or build a new custom home, the potential of this Lake Apopka property is unmatched. The location is exceptional. Just a short golf cart ride takes you to historic downtown Winter Garden, home to award-winning restaurants, a local brewery, live music, artisan eateries, museums, a theater, galleries and boutique shopping. The nationally recognized Winter Garden Farmers Market and the 22-mile West Orange Trail for biking, recreation and running are also nearby. With easy access to major highways, area golf courses and Orlando’s world-class attractions, this property combines lakefront lifestyle, convenience and investment potential. This Winter Garden lakefront home on Lake Apopka will not be completed by the seller prior to closing and is being offered as-is, providing a once-in-a-lifetime chance to own over an acre of prime Florida lakefront real estate with endless possibilities.

1507 N Fullers Cross Road, Winter Garden

$456,990

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

Beautifully designed townhome featuring 3 bedrooms, 3 bathrooms, and a flex room/office, located in the highly desirable Hamlin Ridge community, just off SR 429. Enjoy unmatched convenience with easy access to major interchanges. Hamlin Ridge offers the perfect blend of comfort and Central Florida living.

16376 Hamlin View Street, Winter Garden

$345,000

Showalter Park SubDv. ⋅ 34787 Zip Code

Build your dream home in the heart of Winter Garden on this rare .18-acre vacant lot, perfectly positioned for lifestyle and convenience. Just a short stroll from Historic Downtown Winter Garden, you’ll have easy access to charming shops, award-winning restaurants, live entertainment, and the scenic West Orange Trail for biking or walking. Enjoy the vibrant community atmosphere and weekend farmers markets that make this area one of Central Florida’s most beloved destinations. This prime homesite offers the flexibility to design and build a custom residence that reflects your unique vision. Nestled in a peaceful neighborhood of beautiful homes, yet only minutes from Disney and major highways, it’s an ideal balance of tranquility and accessibility. With utilities nearby and top-rated schools in the area, this property is ready for your plans to take shape. Whether you’re an investor or future homeowner, this location promises strong long-term value. Don’t miss the chance to create something truly special — your custom home in the heart of Winter Garden awaits.

282 E Newell Street, Winter Garden

$445,000

4 Beds ⋅ 2 Baths ⋅ East Garden Manor Second Add SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Move in ready, great location, 5 minutes to Downtown Winter Garden, property offers 4 bedrooms 2 bedrooms, metal roof, huge back yard,No HOA, a gazebo. Walking g distance to elementary school. Close to major Roads, highways, hospitals, shopping centers, restaurants.

320 Pennsylvania Avenue, Winter Garden

$774,500

2 Beds ⋅ 3 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code

Sold Data Only

15515 Orchid Rose, Winter Garden

$1,875,000

5 Beds ⋅ 5 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code

Step into luxury with this brand-new, custom-built J&J home! Featuring 5 spacious bedrooms, 4.5 baths, plus a loft and flex space, this home is designed for both comfort and style. GREEN certified home. The primary bedroom and two additional bedrooms are conveniently located on the main floor, offering easy living. Chef's kitchen with monogram appliances and a scullery kitchen complete with another refrigerator, sink, and tons of shelving. Enjoy quick access to the West Orange Fitness Trail and just 1.2 miles to historic downtown Winter Garden, with all its charming shops and dining options. Located in the Golf Cart District, this home is perfect for an active, convenient lifestyle. Relax in your private backyard oasis with a sparkling pool, spa, outdoor kitchen, and fully fenced-in yard. No HOA, and an oversized 3-car garage complete this exceptional property. Don’t miss your chance to own this one-of-a-kind home!

1020 Tildenville School Road, Winter Garden

$687,200

4 Beds ⋅ 4 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

New Construction - Sold Data Entry Only

18076 Cider Mill Lane, Winter Garden

$1,304,755

5 Beds ⋅ 5 Baths ⋅ Lake Star/Ovation Ph 1a SubDv. ⋅ 34787 Zip Code

New Construction Data Entry Only

17420 Glossy Pomelo Way, Winter Garden

$470,000

3 Beds ⋅ 3 Baths ⋅ Harvest/Ovation SubDv. ⋅ 34787 Zip Code

Sold Date Entry Only

13813 Luna Harvest Avenue, Winter Garden

$670,000

3 Beds ⋅ 4 Baths ⋅ Hickory Lake Estates SubDv. ⋅ 34787 Zip Code

Rare opportunity to own a true lakefront property in the heart of Winter Garden. This 3-bedroom, 2 full and 2 half-bath home sits on 100 feet of frontage on Lake Hickory Nut, offering endless potential for renovation or a complete custom transformation. Built in 1983, the home features solid bones and has been well maintained structurally, with a new roof installed in 2021 and a composite dock added in 2018. The interior is original and ready for a buyer with vision to bring it to life. Located on a quiet street with no HOA, the property offers direct lake access and incredible views. Enjoy fishing, boating, paddleboarding, and serene sunsets right from your backyard. Conveniently located minutes from Hamlin Town Center with access to dining, shopping, a movie theater, hospital, and major highways including SR-429 for easy commuting. Zoned for top-rated schools and surrounded by new development, this is one of the last original lakefront homes in the area, making it a true hidden gem. Don't miss your chance to invest in location, lifestyle, and long-term value. Interior photos will be posted on 8/20. Inside is all original.

9354 Lake Hickory Nut Drive, Winter Garden

$1,051,200

5 Beds ⋅ 5 Baths ⋅ Silverleaf Oaks/Hamlin Ph 3a SubDv. ⋅ 34787 Zip Code

Sold Data Entry Only

16353 Bright Leaf Road, Winter Garden

$375,000

3 Beds ⋅ 3 Baths ⋅ Black Lake SubDv. ⋅ 34787 Zip Code

Best-Priced New Construction Opportunity in Winter Garden - Unlock Immediate Value. Welcome to 14804 Coscester Street, a modern new-construction home offering the perfect combination of space, functionally, and value in one of Winter Garden's fastest-growing corridors. This thoughtfully designed residence features an open-concept layout, spacious living areas, and a contemporary kitchen equipped with sleek cabinetry, stainless steel appliances, and ample counter space - ideal for both everyday living and entertaining. Generous bedroom and well-appointed bathrooms provide comfort and flexibility for a variety of lifestyles. What truly sets this home apart is its exceptional pricing relative to surrounding communities, making it one of the best vale opportunities currently available in Winter Garden. For buyers seeking maximum square footage, modern constructions, and long-term upside potential, this property delivers. Whether you're a first-time homebuyer looking to enter the market, or an investor seeking a strong rental asset in a high-demand area, this home offers immediate equity potential and long-term growth positioning. Additional highlights include: modern construction with efficient features; open layout with abundant natural light; competitive pricing designed to create instant value; ideal for primary residence or investment strategy. Priced to Sell - opportunities like this are rare in today's market. Schedule your private showing today and secure one of Winter Garden's best value homes.

14804 Coscester Street, Winter Garden

$465,000

2 Beds ⋅ 1 Baths ⋅ Mountain Park Orlange Groves SubDv. ⋅ 34787 Zip Code

**Imagine waking up to the gentle shimmer of lake water through a canopy of ancient oaks…** Tucked away on 1.75 wooded acres along the shores of Lake Ingram, this property is a rare opportunity to own a piece of “Old Florida” in the middle of one of Central Florida’s most vibrant growth areas. The moment you arrive, you’re greeted by the sound of rustling leaves, dappled sunlight through sprawling oak branches, and the peaceful calm of life by the water. Spend your mornings sipping coffee on your porch as the lake comes alive with birds and soft breezes. Afternoons can be filled with fishing from your private shoreline, kayaking across the water, or simply relaxing in the shade of your trees. Evenings bring stunning sunsets over the lake—nature’s daily masterpiece—right in your own backyard. The existing small wood-frame home offers endless possibilities: restore it for a cozy lakeside getaway or start fresh and build your dream home to take full advantage of the views. A separate laundry room and a large storage building is ready for your tools, toys, or hobby space. The property is on well and septic, giving you independence and lower utility costs. While the setting feels like a private retreat, you’re just minutes from modern conveniences—highly rated new schools, Winter Garden Village, historic downtown Winter Garden’s shops and weekly farmers market, state-of-the-art medical facilities, and major roadways for quick access to Disney, Horizon West, and beyond. This is more than property—it’s a lifestyle. A chance to slow down, breathe deeply, and enjoy the timeless beauty of lakefront living, all while being moments from the best that Central Florida has to enjoy.

17226 Lake Ingram Road, Winter Garden

$495,000

3 Beds ⋅ 2 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code

Come see this Lovely mid-century home located in a highly desirable Winter Garden neighborhood! 3 blocks north of historic Plant St in the Golf Cart District. NO HOA! 3 Bedroom, 2 Bath home has been updated and comes with solar panels. Open floor plan, split bedrooms, inside laundry room, custom tile floors and so much more!

237 N Central Avenue, Winter Garden

$560,000

2 Beds ⋅ 2 Baths ⋅ Johns Lake Homesites SubDv. ⋅ 34787 Zip Code

Stunning Sunset views embellish this 2 bedroom / 2 bathroom bungalow on beautiful Johns Lake. Enjoy the peace and tranquility as you feel the breeze off the picturesque setting from your back patio or head out on the water for boating, skiing, or fishing for trophy largemouth Bass. This charming home provides incredible lake views from the Kitchen, Primary Suite, and Family room (ordained with rustic stone walls and wood burning fireplace). This Gem awaits your finishing touches to create a true masterpiece! Conveniently located to downtown Winter Garden, Winter Garden Village, restaurants, shops, Disney theme parks, and Universal theme parks. Come and see all that this prize property has to offer.

38 Live Oak Road, Winter Garden

$1,570,500

3 Beds ⋅ 4 Baths ⋅ 34787 Zip Code

A Rare Slice of Serenity in the Heart of Horizons West — 5526 Tiny Road Almost five acres in the middle of one of Central Florida's most sought-after communities isn't just rare — it's nearly impossible to find. While the rest of Horizons West builds closer together, 5526 Tiny Road sits on almost five rolling, private acres surrounded by open sky, a private pond, and natural Florida landscape — all within walking distance of community trails, top-rated schools, and the brand-new Orange County Library currently under construction just steps away. This is the property buyers spend years waiting for. The freedom of acreage. The convenience of community. No HOA. No compromise. The custom-built 2007 estate offers 2,400 square feet of thoughtfully designed living space — three bedrooms, a spacious loft, and 2.5 bathrooms inside, plus a half bath in the oversized 3.5-car garage built for the enthusiast, the workshop, the toys, or all three. The open-concept layout is filled with natural light, anchored by a gourmet kitchen and flowing living spaces designed for both everyday comfort and effortless entertaining. Step outside and the property truly comes alive. A front gazebo attached to the home frames sweeping views across the acreage. The screened rear lanai overlooks a nature preserve. Sunrises and sunsets paint the elevated ridge in a way that no subdivision lot can replicate. Wild turkeys, native birds, and open Florida sky are your neighbors. Just a short ride to Hamlin Town Center, Disney World, SR-429, and everything Horizons West continues to build around you — including planned road enhancements to Tiny Road itself, with landscaped medians and expanded sidewalks that will further elevate the entrance to this property. Properties like this don't come back to market. Once it's gone, it's gone — because there is nothing left to build like it here. 3 Bed | Loft | 2.5 Bath + Garage Half Bath | 3.5-Car Garage | Almost 5 Acres | No HOA | Custom 2007 Build | Private Pond | Horizons West / Independence-Summerport

5526 Tiny Road, Winter Garden

$799,900

Acreage & Unrec SubDv. ⋅ 34787 Zip Code

Serene 5 acre property! Zoned for residential and agricultural use. Whether you envision building your dream home, farming or simply enjoying the peaceful landscape, this land offers country living without sacrificing city amenities. For those looking for a turnkey solution, the property is also available as a to-be-built custom home opportunity with Lionshead Homes, allowing buyers to design and build a luxury residence tailored to their lifestyle. Conveniently located just 7 minutes to Publix at Hamlin or Publix at Stoneybrook. Shopping, dining, medical offices, hospitals, movie theater are all close by! Disney World 20 minutes. Orlando International Airport 35 min. Contact us for additional information and take the first step towards owning your slice of rural paradise!

9940 Black Bear Lane, Winter Garden

$154,000

3 Beds ⋅ 2 Baths ⋅ Bay St Park SubDv. ⋅ 34787 Zip Code

This is a fantastic fixer-upper opportunity for investors or homeowners seeking a project in a prime Winter Garden location. Just 5 minutes from the charming Downtown Winter Garden and conveniently close to major routes like SR-429, this property offers immense potential. The home is being sold as-is and requires a complete rehab, allowing you to fully customize it to your vision. It features a carport, two bathrooms, and four versatile flex rooms, which can be transformed to suit your needs. Whether you're looking to flip or renovate for long-term investment, this property offers a solid foundation and great location to build equity. Don't miss the chance to unlock its potential!

1065 Lincoln Terrace, Winter Garden

$655,000

3 Beds ⋅ 2 Baths ⋅ Winter Garden Shores First Add SubDv. ⋅ 34787 Zip Code

Mid-Century Charm Meets Modern Comfort in Winter Garden! Discover the perfect blend of classic appeal and contemporary upgrades in this delightful 3-bedroom, 2-bath pool home, ideally situated on a generous .30+ acre lot just blocks from downtown Winter Garden. Best of all, there's no HOA! Step inside and appreciate the thoughtful updates that complement the home's timeless mid-century architecture. The kitchen boasts updated Bosch appliances, including a 2021 induction range and 2023 wall oven for a total of two ovens, along with quartz countertops and an updated farm sink. You'll find engineered hardwood floors in the family room, kitchen, and hallway, and custom window blinds throughout. Peace of mind comes with a brand-new roof (July 2025), rain gutters, an AC unit replaced in 2019, and a gas hot water heater from 2018. The primary bedroom suite offers three deep closets with custom doors and a renovated en-suite bath (2021) featuring new tile, a walk-in low threshold shower, and modern fixtures that maintain the home's classic character. The hall bath was also renovated in 2023 with new tile and paint. The dining room provides a cozy ambiance with a gas fireplace and built-in shelves, while French doors open to a spacious 26x17 covered and screened back porch wired with Bluetooth speakers and also has a 220 power hookup for a hot tub. A versatile mud room/art studio/office and a dedicated laundry room add to the home's functionality. The outdoor living space is a true oasis, featuring a fenced backyard (2019) with an amazing heated saltwater pool (2019), complete with a sun ledge. The yard is kept lush with an irrigation system fed by a well (pump replaced 2020) and a French drain system (2019) for optimal drainage. The north gate is a double gate, allowing boat or RV parking behind the fence, with an RV electric outlet on the side of the house. Plus, there's a large elevated workshop building with electricity and AC for your projects (As Is). In 2023, a variance was obtained through the City of Winter Garden to build a new structure where the current workshop sits, which also allows for an attached covered veranda to be built. Beyond your doorstep, the vibrant heart of Winter Garden awaits. This home is located in the golf cart district, allowing you to drive your own golf cart on approved roads. Enjoy leisurely strolls to the weekend farmers market, participate in festive holiday events, and explore a diverse array of restaurants and shops. You're also within walking distance to Lake Apopka, where breathtaking sunsets are a daily spectacle, and it's renowned as one of Florida's top three birding areas. The Jessie Brock Community Center (offering exercise and Crealde art classes) and its pond with a paved walking circuit and exercise stations are also just a short walk away, as is the West Orange Bike Trail. This Winter Garden gem offers not just a home, but a lifestyle. Don't miss your chance to own a piece of this charming and convenient community!

423 N Main Street, Winter Garden

$1,780,000

5 Beds ⋅ 5 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code

Exquisite New Construction in the Heart of Winter Garden’s Golf Cart District – Over 4,000 Sq Ft of Craftsman Charm! Step into timeless style and modern luxury with this brand new Craftsman-style masterpiece, perfectly situated on a charming cobblestone one-way street in the highly sought-after Golf Cart District of historic Winter Garden. Boasting over 4,000 square feet of beautifully appointed living space, this 5-bedroom, 4.5-bathroom estate offers the perfect blend of character, comfort, and convenience—all with NO HOA dues or restrictions. Set on over a third of an acre, the home impresses at first glance with custom landscaping, a massive covered front porch, and timeless curb appeal. Inside, enjoy warm wood flooring throughout, striking custom wooden beams in the foyer, and a spacious great room with electric fireplace—all flooded with natural light. Designed for entertaining, the open-concept layout includes a chef’s kitchen with custom cabinetry, gas appliances including professional grade gas range, built-in refrigerator and freezer stacks, walk-in pantry, wet bar with wine refrigerator, and a spacious island. Step outside to your private oasis complete with a large covered and pavered back patio, summer kitchen (grill + outdoor refrigerator), fenced yard, and a sparkling pool with heated spa—perfect for entertaining year-round. The downstairs primary suite offers a peaceful retreat with a spa-inspired bath, spacious shower, and massive walk-in closet finished with built-ins. A second downstairs bedroom with its own walk-in closet and nearby bath is perfect for guests or a home office. Upstairs, you'll find three additional bedrooms (each with walk-in closets), a loft living area, and even a second laundry/utility room for added convenience. The main laundry room downstairs is oversized, filled with natural light and extensive cabinetry, and an adorable mudroom just off the garage. Additional features include: Two-car garage PLUS a golf cart garage, dual tankless gas water heaters, gas appliances, and fully fenced back yard. This rare Winter Garden gem offers the best of both worlds—new construction luxury with the charm of Downtown Winter Garden living. Just moments from shops, dining, and everything downtown Winter Garden is known for. Don’t miss this opportunity to own a truly one-of-a-kind home in one of Central Florida’s most desirable communities.

958 Tildenville School Road, Winter Garden

$965,960

5 Beds ⋅ 9 Baths ⋅ Silverleaf Oaks/Hamlin Ph 3a SubDv. ⋅ 34787 Zip Code

Sold Data Only. Beautiful Scarlett home designed by Pulte Homes at Silverleaf Oaks, with tons of upgrades

16337 Grey Pine Drive, Winter Garden

$533,990

4 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve At Hamlin Phase 2c 115/07 Lot 2 SubDv. ⋅ 34787 Zip Code

Meritage Homes New construction

16448 Silver Brook Way, Winter Garden

$575,000

4 Beds ⋅ 2 Baths ⋅ Garden Heights SubDv. ⋅ 34787 Zip Code

Welcome to 517 Garden Heights Drive — a fully renovated 4-bedroom, 2-bath modern farmhouse on a spacious 0.33-acre lot in the highly desirable golf cart district of Winter Garden. Just one mile from the vibrant Plant Street district and offering Lake Apopka views from the driveway, this home delivers the perfect blend of lifestyle and long-term value. Key updates include a brand-new roof (installed July 2025), a newer HVAC system (2021), and a new water heater (2025) — providing essential peace of mind from day one. With the ongoing upturn in the Winter Garden real estate market, this property also represents a smart investment opportunity in one of Central Florida’s most thriving communities. Step inside to discover nearly 2,000 square feet of carefully curated living space with all-new tile flooring, fresh paint, updated texture, and modern wood paneling accents. The open-concept layout features a striking shiplap fireplace, brand-new ceiling fans and lighting fixtures throughout, and a showstopping kitchen designed for both function and flair — complete with quartz countertops, shaker cabinetry, gold hardware, stainless steel appliances, and stylish pendant lighting. Both bathrooms have been thoughtfully redesigned with custom tile work, dual vanities, and designer finishes, while the spacious primary suite includes a sliding barn door and spa-style bath. Enjoy seamless indoor-outdoor living with a fully screened-in porch and outdoor wet bar, ideal for entertaining or relaxing with a view of your expansive backyard. A detached shed offers convenient storage, and the 2-car garage adds practical convenience. Best of all? No HOA. This move-in ready home checks all the boxes with thoughtful upgrades, timeless style, and an unbeatable location — the perfect place to live, enjoy, and grow equity for years to come.

517 Garden Heights Drive, Winter Garden

$440,000

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

Welcome to Tribute at Ovation, a stunning new construction townhome now for sale. This beautiful townhome offers 3 bedrooms, 2.5 bathrooms, an open-concept living space perfect for entertaining and family gatherings, brand new construction with modern finishes, a 2-car detached garage, and more. The open-concept layout creates a spacious feel while maintaining functional living areas. Winter Garden offers residents a charming neighborhood atmosphere with tree-lined streets and community parks within easy reach. The area boasts numerous parks and recreational facilities where you can enjoy Florida's beautiful weather year-round.

15328 Burgtheater Dr, Winter Garden

$609,290

3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code

Sold data entry only

6436 Tabebuia Parkway, Winter Garden

$470,000

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

Sold data entry only.

15340 Burgtheater Drive, Winter Garden

$2,625,000

4 Beds ⋅ 5 Baths ⋅ Acreage SubDv. ⋅ 34787 Zip Code

Fabulous private location with 5 beautiful acres and gated entry - Bring your horses! ** 2538sf horse barn with 4 stalls, tack room and 2nd room that could also be used as a tack room ** Nelson automatic horse waterers included ** Horse corral and 1 pasture/paddock that could be divided into 2 ** Additional 1800sf pole barn ** Home, barn and 1800sf pole barn and casita all 2019 BUILT ** 1800sf pole barn perfect for storing all your equipment or an RV with 12' overhead doors on both ends ** Casita / guest house has a separate entry, full bath and full AC unit perfect for an in-law situation, guests or work out space ** 5 car attached garage (3.5 & 1.5 car) and tile roof ** All bedrooms are ensuite ** Stroll the 2500sf trail around the property and 300+/- sf of bamboo trails around the front & side of the property ** 2 Rainbird sprinkler irrigation systems (well) used for the home and another for the horses & pastures ** 1000 gallon + 500 gallon propane generators that run the house & barn ** Luxurious outdoor living space with well designed pool offering raised planting beds with lovely waterfalls, sun shelf and unique curved heated raised spa ** Enjoy the lovely patio space offering a travertine patio, attractive tongue and groove wood ceiling, Nevada cobblestone decorative archways and sitting space complete with a cozy 2 sided fireplace w granite hearth, TV and screened lanai ** Outdoor kitchen (never used) with Nevada cobblestone, a grill and refrigerator ** 12' ceilings, 10' doors & Venetian plaster accents accentuate the beauty of this home ** Beautiful primary bedroom featuring a tray ceiling with wood tongue and groove inlay, fireplace with Nevada cobblestone and triple sliding glass doors to the outdoor living area and hall leading to the ensuite bath with zero entry full shower with rainhead shower, stone tub and room size walk in closet with custom built ins **The well apportioned great room features a fireplace, wood beams, tongue and groove ceilings, built in display areas and 3 sets of triple sliding glass doors leading to the amazing outdoor space ** Fabulous Kitchen with attractive Nevada cobblestone enhancements around the counters and cooking area, stone COUNTERS & flowing backsplash, breakfast bar, espresso cabinets and built in convection stove **

9201 Tower Pine Drive, Winter Garden

$775,000

3 Beds ⋅ 3 Baths ⋅ Winter Garden Shores SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Welcome to your personal retreat in the heart of Winter Garden! Just a short distance from the charm of historic Plant Street. This meticulously maintained three-bedroom, three-bath pool home with a dedicated office blends relaxed luxury with everyday function in one of Central Florida's accessible, vibrant neighborhoods and with no HOA to limit your lifestyle. Go inside to find beautiful wood-look tile throughout, an open kitchen with stainless steel appliances, and an expansive 34-by-19-foot family room with vaulted ceilings centered around a stunning floor-to-ceiling stone fireplace. French doors open to your private backyard oasis, where a resort-style heated pool and spa (new pump 2024, new heater 2025) are surrounded by lush planting beds, a gas fire pit, and a covered dining area that's ideal for hosting year-round. The luxurious primary suite is a retreat, featuring a spa-like bath with a huge walk-in shower, double vanities, a soaking tub, and a custom walk-in closet. Practical updates include a new roof and air conditioner (2022), new windows (2017) and water heater (2018), giving you peace of mind and turnkey convenience. Privacy is guaranteed with a full vinyl fence, and the gated rear alley access makes room for your boat or RV, an exceptional find in this neighborhood. Enjoy golf cart rides to the West Orange Trail, weekly farmers markets, local restaurants and community events just minutes away.

426 N Boyd Street, Winter Garden

$838,115

5 Beds ⋅ 4 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code

Beautiful Thoreau model with spacious 3,208 sq ft home in the SilverLeaf community

5277 Citrus Leaf Boulevard, Winter Garden

$459,000

3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks At Hamlin SubDv. ⋅ 34787 Zip Code

Discover the Julep—Silverleaf Oaks’ most spacious townhome design, offering 1,770 square feet of modern living. The bright and open main level features a stylish kitchen, convenient powder bath, and a spacious gathering room that flows seamlessly to a private patio—perfect for indoor/outdoor entertaining. Upstairs, you’ll find a relaxing owner’s suite, a flexible loft area, and additional bedrooms that create a comfortable retreat for everyone. With 3 bedrooms, 2.5 baths, and a 2-car garage, this two-story layout blends style and functionality in one of Winter Garden’s most desirable communities.

6430 Tabebuia Parkway, Winter Garden

$485,000

4 Beds ⋅ 2 Baths ⋅ Glenview Estates 2nd Add SubDv. ⋅ 34787 Zip Code

Beautifully remodeled home near Historic Downtown Winter Garden. This 2-story 4 bed / 2 bath home with a 2-car garage sits on over half an acre with a creek in the backyard on a quiet, low traffic circle. This home has so many great features including a completely remodeled kitchen (2022) a family room with a wood burning fireplace with a stone hearth and mantel, nicely remodeled hall bath, and nice neutral colors.. Other features include New A/C in 2019 ** New Water Heater ** Roof 8 years ** New Vinyl Flooring throughout ** New Garage Door Opener ** New Seamless Gutters ** Parking Extended for Boat/RV/Golf Cart ** Transferable Termite Bond. Ride your golf cart to enjoy one of the quaint restaurants in Winter Garden's popular historic district, or visit one of the many parks downtown. Enjoy no HOA in this quiet neighborhood with mature trees, so close to Lake Apopka.

956 Glenview Circle, Winter Garden

$1,058,290

5 Beds ⋅ 4 Baths ⋅ Silverleaf Oaks At Hamlin Phase 3a SubDv. ⋅ 34787 Zip Code

Seek out new heights in this two-story home design that takes easy living to the next level. Entertain in the connected gathering room, kitchen, and café area. Transform the flex space into a home office or den. After a long day, enjoy family movie night in the upstairs loft or escape to the private Owner's Suite.

16311 Bright Leaf Road, Winter Garden

$750,000

3 Beds ⋅ 2 Baths ⋅ Lake Avalon Groves Rep 02 SubDv. ⋅ 34787 Zip Code

Previous buyer financing fell through. RARE Winter Garden Opportunity — Over 2.5 Acres! Welcome to your own private retreat in the heart of Winter Garden's most exciting growth corridor. Whether you're envisioning a peaceful country lifestyle or planning your next luxury estate, this property offers endless opportunities. Nestled behind a private gate and framed by a breathtaking canopy of mature trees, the entrance opens to a driveway leading to the home, completely surrounded by lush, usable land. The single-story well-maintained pool home offers over 2,500 square feet of living space. Originally built in 1982, the home features original hardwood floors in most of the living areas, a well-equipped kitchen with quartz countertops, and spacious living areas centered around a beautiful stacked-stone, wood-burning fireplace. All three bedrooms are generously sized, with two cocated at the rear of the home—one offering direct access to the pool area. An added 400-square-foot bonus room at the front of the home provides versatile space for your needs. Just off the main living area, double French doors lead to a charming Florida room—perfect for relaxing or entertaining family and friends. Step outside to your private oasis: a large custom-designed pool surrounded by nature. With agriculture zoning and all 2.57 acres high-and-dry, you have the freedom to build your custom dream home, create a nursery, hobby farm, establish a small agricultural business, or simply enjoy wide-open space and privacy. Enjoy peaceful evenings under the stars in your own slice of paradise. Located just minutes from Hamlin Town Center, Horizon West, and a short drive to Disney, this is a rare blend of rural serenity and suburban convenience.

17877 Phil C Peters Road, Winter Garden

$990,900

4 Beds ⋅ 4 Baths ⋅ Oakland Park South SubDv. ⋅ 34787 Zip Code

Sold Data entry only

1180 Riverway Drive, Oakland

$280,000

2 Beds ⋅ 1 Baths ⋅ Shadow Lawn SubDv. ⋅ 34787 Zip Code

Charming Bungalow Just Minutes from Downtown Winter Garden Welcome to your chance to own a slice of Winter Garden charm! This cozy 2-bedroom, 1-bath bungalow is perfectly located within one mile from Plant Street, the Crooked Can Brewery, and all the energy of Historic Downtown Winter Garden. Enjoy your weekends strolling through the award-winning Farmers Market, grabbing coffee from a local café, biking the West Orange Trail, or catching live music and seasonal festivals. You're also just minutes from the Pickleball Courts at Veteran's Park, boutique shopping and community events - everything you love about Winter Garden is right outside your door. Filled with character and charm, this home is ready for everyday living with room to make it your own. Whether you're a first-time buyer, looking for a winter retreat, or seeking a smart investment, this is a rare opportunity to be in one of Central Florida’s most sought-after neighborhoods. Step outside to a spacious yard that’s perfect for relaxing, entertaining, or even planning your dream garden or outdoor living area. With top-rated schools nearby, easy access to major highways, and less than 30 minutes to Disney, Universal, and Orlando’s top attractions—you’ll enjoy small-town charm without giving up modern convenience. Come see what makes this home and location so special—and imagine your life in beautiful Winter Garden!

135 E Story Road, Winter Garden

$1,795,000

5 Beds ⋅ 6 Baths ⋅ 34787 Zip Code

New Custom Home in Winter Garden.

502 Winter Garden Vineland Road Unit R, Winter Garden

$739,000

4 Beds ⋅ 4 Baths ⋅ Quesinberry Sub SubDv. ⋅ 34787 Zip Code

Duplex home in Downtown Winter Garden! 3 bedroom and 2 bathrooms on each side with a total of 6 bedrooms and 4 bathrooms. One block from Plant street in Winter Garden!

209 S Boyd Street, Winter Garden

34787 Zip Code Real Estate & Homes with No HOA Fee

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