Winter Garden FL Historical Real Estate, Homes for Sale

2 Beds ⋅ 1 Baths ⋅ Jewel Heights SubDv. ⋅ 34787 Zip Code

Exceptional Downtown Winter Garden Investment Opportunity! Located in one of the most desirable areas of Downtown Winter Garden, this property presents an outstanding opportunity to build your dream home or complete a substantial renovation in an area where redevelopment continues to thrive. The existing 1924 home is approximately 912 square feet with 2 bedrooms and 1 bathroom and is being sold AS-IS, with the value primarily in the location and land. Public records indicate a 5,024-square-foot lot zoned R. Enjoy the unmatched lifestyle that Downtown Winter Garden is known for, with convenient access to Plant Street's award-winning restaurants, boutique shopping, the weekly Farmers Market, Crooked Can Brewing Company, live entertainment, and the West Orange Trail. Whether you're a builder, investor, or buyer looking to create a custom home in one of Central Florida's most sought-after downtown districts, this is a rare opportunity to secure a property with tremendous potential in a location where new construction and beautifully renovated homes continue to command premium values. Don't miss your chance to invest in the future of Downtown Winter Garden!

641 S Boyd Street, Winter Garden

$179,000

2 Beds ⋅ 1 Baths ⋅ Solomon Sub SubDv. ⋅ 34787 Zip Code

Under contract-accepting backup offers. ATTENTION INVESTORS & BUILDERS! Rare, low-priced opportunity in the highly sought after Walk to Downtown Winter Garden! This is a rare chance to secure a spacious lot with endless possibilities in a premium location with NO HOA, top-rated schools, and city water and sewer connections available. Zoned R-2, this property is a blank canvas perfect for savvy investors or builders. Maximize your investment by exploring options for a duplex, an ADU, or applying to split the lot. The current structure requires a complete remodel or teardown, making it the perfect site for your next project. Cash buyers only. Opportunities at this price point ($179,000) in 34787 do not last. Schedule your showing today!

341 E Lafayette Street, Winter Garden

$434,000

4 Beds ⋅ 2 Baths ⋅ Joe Louis Park Q162 SubDv. ⋅ 34787 Zip Code

PHENOMENAL Double corner LOT NO HOA, newer updates INCLUDE: brand new AC, new roof, Re-Plumb, house/ Electrical Panel/rewired. Updated kitchen and bathrooms, Located off the Kitchen is the Dining room area which is open to the Living Room area. The master Bathrooms is completely updated features a standing shower. The Laundry is located inside. The carport/workshop is spacious to hold 2 cars and storage. Enjoy the nice-sized Backyard with a that is big enough for the whole family. You don't want to miss this opportunity to make this house your home! very nice WORKSHOP ** VALUE IS IN THE both property/land

689 Bethune Avenue, Winter Garden

$440,000

2 Beds ⋅ 1 Baths ⋅ Borders & Woosley Sub SubDv. ⋅ 34787 Zip Code

Located within Winter Garden’s golf cart district and just minutes from Plant Street, this property offers a distinctive combination of current residential use, C-2 General Commercial zoning, and no HOA. The single-story, concrete-block home includes 2 bedrooms, 1 bathroom, 1,034 square feet of heated living space, an enclosed porch that provides additional flexible space, and a roof replaced in 2023. The interior is ready for renovation, allowing the next owner to update the property according to their intended use and vision. Situated on an approximately 0.19-acre homesite, the property also features mature shade trees, a concrete driveway, and fenced sections of the yard. Its central Winter Garden location provides convenient access to the restaurants, shops, farmers market, community events, and West Orange Trail surrounding downtown and Plant Street, while nearby golf-cart-friendly roadways offer another way to explore the area. Whether considered for continued residential use, a renovation project, or a future business opportunity, this property presents a range of possibilities in a well-connected location. Buyers should independently verify all intended uses, permitting requirements, and zoning regulations with the City of Winter Garden.

721 S Woodland Street, Winter Garden

$525,000

3 Beds ⋅ 2 Baths ⋅ Edgewater Beach SubDv. ⋅ 34787 Zip Code

Welcome to this charming 3 bedroom, 2 bathroom LAKEFRONT home, offering the perfect blend of comfort and convenience with NO HOA fees! The home features timeless terrazzo flooring in the main living areas and guest bedrooms while the primary bedroom is finished with stylish wood plank tile. The updated kitchen boasts stainless steel appliances and both bathrooms have been beautifully renovated. Outside, enjoy your private oasis with a serene view of John's Lake, where you can relax on the front porch and enjoy the beautiful sunrise and take advantage of the floating dock for boating and fishing. The fenced-in yard offers plenty of space for outdoor activities and a shed provides additional storage. Conveniently located next to boat ramp, this property is ideal for lake lovers who want easy access to all the fun John's Lake has to offer. The home is also just minutes from Hwy 50, the Turnpike, Downtown Winter Garden, Hospitals, Shopping and only 30 minutes from Orlando International Airport—making it a prime location for both peaceful living and easy travel. Roof and AC are 10 years old. New septic 4 years ago. Don't miss out on this rare find—schedule your showing today! Great for investment and short term rental!

13619 Lake Boulevard, Winter Garden

$450,000

3 Beds ⋅ 2 Baths ⋅ Pleasant Park SubDv. ⋅ 34787 Zip Code

Welcome to 217 W. Story Road, a beautifully located home in Downtown Winter Garden, Florida, offering the walkable, golf cart friendly lifestyle that has made Winter Garden real estate some of the most sought after in Central Florida. Situated just a few blocks from the iconic Plant Street Market, this home places you in the center of everything that makes historic Downtown Winter Garden one of the area's premier destinations. Enjoy convenient access to local restaurants, boutique shopping, coffee shops, breweries, and the award winning West Orange Trail. Spend your weekends at the popular Winter Garden Farmers Market, live entertainment events, and seasonal festivals, all just minutes from your front door. Located in the highly desirable golf cart district, residents can easily access Downtown Winter Garden's newest restaurants and exciting developments that continue to enhance the area's charm and long term appeal. With close proximity to Winter Garden Village, major highways, Walt Disney World, and all that Central Florida has to offer, this location combines small town character with modern convenience. Whether you're searching for a home near Plant Street Market, a property in the golf cart district, or a home in historic Downtown Winter Garden, 217 W. Story Road offers a rare opportunity to experience one of the most desirable lifestyles in Winter Garden, FL.

217 W Story Road, Winter Garden

$255,000

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

This beautifully updated 3 bedroom, 1 bathroom home offers modern comfort at an unbeatable value. With 814 sq ft of living space, it features a brand-new roof, newer A/C, fresh interior and exterior paint, a fully remodeled kitchen with a new fridge, 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 must be verified by the buyer.** FHA buyers are welcome!

1105 Lincoln Terrace, 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

$1,080,000

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

Appraisal in hand! 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

$800,000

4 Beds ⋅ 2 Baths ⋅ Fries Winter Garden SubDv. ⋅ 34787 Zip Code

Coming Soon! Awesome Opportunity to own in Historic Winter Garden. LOT parcels in the front are being sold seperate.

214 S Woodland Street, Winter Garden

$410,000

3 Beds ⋅ 2 Baths ⋅ Overstreet Crate SubDv. ⋅ 34787 Zip Code

Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.

420 E Cypress Street, Winter Garden

$500,000

3 Beds ⋅ 2 Baths ⋅ Rep Pt Pleasant Park Sub SubDv. ⋅ 34787 Zip Code

Under contract-accepting backup offers. Some Photos virtually staged. Solidly built mid-century home in an exceptional Downtown Winter Garden location, just moments from Plant Street shopping and dining, Crooked Can Brewing Company, Garden Theatre, the splash pad, and all the charm of the golf cart district. Enjoy dinner downtown, then take your golf cart to Newton Park to catch breathtaking sunsets over Lake Apopka. Hard to find, timeless charm and well maintained! Offering 1,716 sq. ft. per the property appraiser, including a spacious laundry room. The roof was replaced in 2016, windows have been updated, and the home includes a termite bond for added peace of mind. Rare opportunity to own a one owner (since the 60's) home, lovingly cared for in a Prime Downtown location~ Schedule your private showing today!

516 S Highland Avenue, Winter Garden

$544,900

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

Along a charming brick street in one of the desirable areas of southwest Orange County, this beautifully updated 1938 cottage-style home offers a blend of historic character and modern convenience in the heart of downtown Winter Garden. On an oversized, fully fenced corner lot within the sought-after golf cart district, this rare gem is just blocks from historic Plant Street, the famed Plant Street Market, weekend farmers market, premier dining, shopping, entertainment and scenic West Orange Trail. This inviting three-bedroom, two-bath home features 1,273 square feet of thoughtfully updated living space with stylish laminate and ceramic tile flooring throughout, blending timeless charm with modern finishes. Inside, you'll find a functional layout with inside laundry, a warm and welcoming atmosphere, and a newer air-conditioning system for added peace of mind. Enjoy quiet mornings or relaxing evenings from the desired front and rear porches overlooking the fully fenced yard, ideal for entertaining, pets or simply enjoying the Florida lifestyle. The oversized double carport and extended driveway provide abundant parking, while the exterior storage room within the carport offers exceptional flexibility for hobbies, tools, golf cart accessories or additional storage needs. Homes with this level of charm, character and accessibility rarely become available in downtown Winter Garden. Combining an unbeatable location, oversized corner lot and the convenience of golf cart living just near everything Plant Street has to offer, this is a special opportunity to own a piece of one of Central Florida's beloved historic communities.

46 W Vining Street, Winter Garden

$335,000

2 Beds ⋅ 2 Baths ⋅ Shadow Lawn L/125 Lot 9 Blk F SubDv. ⋅ 34787 Zip Code

Fully Renovated Turnkey Home in the Heart of Winter Garden, Better Than New! This beautifully reimagined 2-bedroom, 2-bath home has been transformed from the ground up. Every major system and finish is brand new, including the foundation, structural reinforcement, roof, windows, flooring, A/C system, and fully remodeled bathrooms, plus an ADDED second bathroom. The modern kitchen features a brand-new refrigerator, stove, and microwave. No projects, no deferred maintenance, no surprises. Just move in and start enjoying life. Minutes from historic downtown Winter Garden, Plant Street, the West Orange Trail, the Saturday Farmers Market, top dining and shopping, with quick access to SR 429 and the Florida Turnpike for easy commutes to Orlando, Disney, and MCO Airport. First-time buyers may qualify for up to $30,000 in down payment assistance through Orange County and additional Florida state programs. All financing welcome, including Cash, Conventional, FHA, and VA buyers. Turnkey homes like this don't last. Schedule your showing today!

243 Florida Avenue, Winter Garden

$525,990

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

Welcome a beautifully remodeled Winter Garden home that seamlessly blends classic charm with modern upgrades! step inside to discover an open-concept kitchen, top appliances, quartz countertops, sleek modern bathrooms, new windows, and durable waterproof laminate floors, excellent screen porch. Perfect for everyday living and entertaining alike. New windows flood the interior with natural light, while luxury flooring flows throughout for effortless style and maintenance. This inviting 4-bed, 2-bath residence offers 1,487 sq ft of thoughtfully reimagined living space on a generous 0.17-acre lot in the desirable Winter Garden Shores neighborhood. Relax in sleek, modern bathrooms and enjoy the lush Florida weather from your excellent screened porch, ideal for morning coffee or evening gatherings. The home also includes an attached garage and has been upgraded with central air and updated finishes throughout. Located just moments from top schools, City Hall, dining, parks, and major commute routes, this home offers convenience without compromising. Whether you’re a growing family, first-time buyer, or relocating to the area, this Winter Garden gem is not to be missed! Owner offering 5k to closing cost..

113 W 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

$699,000

7 Beds ⋅ 3 Baths ⋅ Burchshire SubDv. ⋅ 34787 Zip Code

ATTENTION INVESTORS! Rare opportunity to own a fully occupied triplex in the heart of Winter Garden. Located within minutes to the popular Plant Street district with its vibrant shops, restaurants, and entertainment. This true triplex sits on an oversized lot and features three renovated units with reliable tenants. Each unit is individually metered for electricity, and the property is connected to city water and city sewer. Tenants pay their own utilities and are responsible for yard maintenance. The oversized lot provides additional flexibility and potential for future expansion such as a garage apartment or in-law suite (buyer to verify zoning and building requirements). Roof replaced approximately 10 years ago. Excellent location with strong long-term appreciation potential.

721 Foster Avenue, Winter Garden

$725,000

4 Beds ⋅ 2 Baths ⋅ Mt Park Orange Grove SubDv. ⋅ 34787 Zip Code

Welcome to 17134 Lake Ingram Rd, which offers LAKEFRONT living with NO HOA on Lake Ingram, The property is 1.16-acres and has 118 feet of waterfront. WALT DISNEY WORLD is approximately 15 minutes away, while Orlando College of Osteopathic Medicine is just minutes away. Opportunity awaits for the current home and pool to be updated to suit the buyer’s personal style and taste. Zoned A-1, the parcel may appeal to buyers seeking space for a custom home or long-term investment. Property sold as-is. Due diligence recommended regarding zoning and development options. Call today to see this unique property in the desirable area of Horizon West.

17134 Lake Ingram Road, Winter Garden

$342,000

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

Updated 2 Bedroom, 1 Bath Home Near Downtown Winter Garden. Welcome to your dream home! This beautifully updated 2-bedroom, 1-bath home is located just minutes from the heart of downtown Winter Garden, Florida. Property Highlights: Fully updated with brand-new cabinetry throughout the home, giving it a sleek, modern look. Stylish bathroom completely renovated with updated fixtures and finishes. New elegant and durable flooring that complements the home's fresh, contemporary design. Freshly painted interior and exterior for a clean, vibrant feel. New roof ensuring peace of mind and energy efficiency. Just minutes away from the charming shops, restaurants, and entertainment of downtown Winter Garden. Easy access to walking and biking trails, local parks, and the farmer's market. This is a rare opportunity to live in a move-in-ready home with so many updates and such a prime location.

636 Coke Avenue, Winter Garden

$1,200,000

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

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

205 Surprise Drive, Winter Garden

$285,000

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

$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

$2,999,000

Fries Winter Garden SubDv. ⋅ 34787 Zip Code

COMMERCIAL property in downtown WINTER GARDEN! Located directly on PLANT STREET in the Historic District Overlay this property offers great exposure. It is currently zoned C-1 and has many permitted uses such as retail establishments, eating and drinking establishments, office & studios, financial institutions, private club, personal service, church and more. Permitted use list available upon request. Total property consist of over 3300 square feet and almost 2700 square feet of interior space. Property is split up unit two units. The first unit is approximately 1050 interior space offering a main retail area measuring 25x22, an office 9x14 and additional room 18x8. There is additional walkway space and two restrooms. The second unit is approximately 2050 interior space offering a 31x14 retail space, and additional spaces measuring 6x14, 8x12,10x17,18x24 and 7x15. There is additional walkway space and one restroom plus rear entrance/exit ability. ENJOY the downtown Winter Garden life.

18 & 20 E Plant Street, Winter Garden

$160,000

. SubDv. ⋅ 34787 Zip Code

Business for Sale Only - Exceptional opportunity to own a well-established beauty Salon in the heart of Winter Garden. Great Located. This Beauty Salon offers unbeatable visibility and foot traffic, making it a high-demand business with strong revenue potential. Key Features: Turnkey Operation: Fully equipped with modern chairs, mirrors, workstations, and a reception area. High-traffic, constant flow of customers. Established Clientele: has built a solid reputation and loyal customer base. This business is perfect for an owner-operator or an investor looking to step into a thriving market with significant foot traffic. With its prime location and steady clientele, this is poised for continued growth. Call to set an appointment.

120 S Dillard Street, Winter Garden

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