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$435,000
8 Beds 3 Baths Twin City Dev Co Sub SubDv. 34787 Zip Code
8 bedrooms. 3 full baths. Approximately 1,750 SF. Just blocks from Plant Street. Space and location set this property apart. Offering 8 bedrooms and 3 full baths across approximately 1,750 SF, the home sits on a 9,431 SF fully fenced lot—a combination of interior space and land increasingly difficult to find this close to Historic Downtown Winter Garden. Built in 1925 and sold as-is, the home presents an opportunity to update and personalize to your own vision. The flexible room count provides options for bedrooms, guest space, home offices, or additional living needs, while the generous 75' x 125' lot leaves plenty of outdoor space to create a garden, entertaining area, or backyard retreat. No HOA, city utilities, and R-2 zoning add to the property's flexibility and long-term appeal. Location is the part that cannot be renovated. Enjoy being just blocks from Plant Street, the Saturday farmers market, restaurants, cafés, shops, entertainment, and the West Orange Trail, with Lake Apopka, SR-429, and Florida's Turnpike conveniently nearby. Currently income producing, the property offers the flexibility to maintain its existing rental use or be delivered vacant upon request. 8 Bedrooms. 3 Full Baths. Approx. 1,750 SF. 0.22 Acres. 9,431 SF Lot. 75' x 125'. No HOA. Bring your vision and make the space your own in a location that's increasingly difficult to replicate. Schedule your private showing today.

208 3rd Street, Winter Garden

$849,900
4 Beds 3 Baths Winter Garden Shores Add 02 SubDv. 34787 Zip Code
This Downtown Winter Garden stunner has continued to evolve with thoughtful, high-value upgrades that make it even more exceptional today. Located in the much sought after golf cart district and just steps from Plant Street’s restaurants, markets, and year-round events, this home blends timeless character with modern convenience in a way few properties can match. Originally reimagined with a full professional remodel in 2023 — including brand-new roof, windows, electrical, plumbing, insulation, luxury vinyl plank flooring, Bosch appliances, Carrara quartz surfaces, and a magnificent, redesigned kitchen. Additional upgrades include a newly constructed one-car garage with parking pad - 2026 and a whole-home generator providing both functionality and peace of mind rarely found in homes of this era. These additions compliment the already impressive split-floorplan featuring 4 bedrooms (and bonus room), 2.5 baths, an oversized island kitchen with fireplace feature wall, gallery-style windows, and a private primary suite with walk-in closet. Every inch of this home reflects quality, style, and intention — from the high-grade materials used throughout to the continued improvements that elevate daily living. Homes like this, with extensive permitted renovations and meaningful new upgrades, simply do not come to market often in Winter Garden. Homes this special in the heart of Winter Garden are rarely available for long — claim it before it’s gone.

368 N Boyd Street, Winter Garden

$289,000
2 Beds 2 Baths Joe Louis Park First Add SubDv. 34787 Zip Code
Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden. Blending modern updates with timeless charm, this move-in-ready residence offers stylish finishes, functional living spaces, and a convenient location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright, refreshed interior featuring contemporary flooring, recessed lighting, updated fixtures, and an open, inviting atmosphere. The fully remodeled kitchen showcases elegant white shaker cabinetry, sleek countertops, stainless steel appliances, and modern hardware, creating a clean and sophisticated space for everyday living and entertaining. The renovated bathrooms feature designer-inspired finishes, including a spacious walk-in shower with stunning marble-look tile, upgraded fixtures, and a modern vanity. Thoughtful updates throughout the home provide a fresh, cohesive look while maintaining comfort and functionality. Outside, enjoy a spacious lot shaded by mature trees, offering room for outdoor entertaining, gardening, pets, or future expansion. Fresh exterior improvements and landscaping enhance the home's curb appeal, while the absence of HOA restrictions provides added flexibility and freedom. Conveniently located near shopping, dining, parks, the West Orange Trail, major highways, and all that Downtown Winter Garden has to offer, this turnkey property presents an exceptional opportunity for homeowners and investors alike. Don't miss your chance to own a beautifully updated home in one of Central Florida's most sought-after communities.

1701 E Bay Street, Winter Garden

$1,020,000
4 Beds 3 Baths Winter Garden Shores First Add SubDv. 34787 Zip Code
Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!

20 E Division Street, Winter Garden

$3,200,000
41 Beds 75 Baths Lake Johns Motel Apts. & Tr. Pk SubDv. 34787 Zip Code
15992 W Colonial Dr, Oakland, FL – 32-Unit Income Producing Multifamily Opportunity Exceptional opportunity to acquire a 32-unit income-producing asset in the heart of West Orange County, ideally positioned along the high-visibility W Colonial Dr / SR-50 corridor in the Town of Oakland. Situated on approximately 2.15 acres, this unique property offers a diverse mix of duplex-style residences, mobile home/RV units, and additional rental pads, creating multiple income streams and long-term upside. Currently generating $34,860 per month in gross rental income the property delivers immediate cash flow while offering significant future value-add and redevelopment potential. Located just minutes from the Florida Turnpike interchange, Downtown Winter Garden, Clermont, and the greater Orlando employment hubs, this site sits directly in the path of West Orange’s continued expansion. The C-1 zoning and strategic frontage on SR-50 make this an especially compelling opportunity for investors seeking stable income today with the flexibility for future repositioning. Whetherd workforce housing and RV income asset, repositioned into a boutique rental community, or held for future redevelopment, opportunities with this combination of location, scale, frontage, and in-place revenue are increasingly rare. (Seller is selling 112 units in total varying in diffrent locations this is 32 of those 112)

15992 W Colonial Drive, Oakland

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

205 Surprise Drive, Winter Garden

$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

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