Refine Search
Map
Sort by
524 S Highland Avenue, Winter Garden
$518,000
3 Beds ⋅ 2 Baths ⋅ Rep Pt Pleasant Park Sub SubDv. ⋅ 34787 Zip Code
**DOWNTOWN WINTER GARDEN UPDATED GEM -- GOLF CART OR WALK TO PLANT STREET** **THREE BEDROOMS + LARGE FLEX SPACE** **UPDATED KITCHEN & FLOORING** **LARGE FULLY FENCED LOT - NEARLY 1/4 ACRE** **NO HOA - LIVE WITHOUT RULES & RESTRICTIONS** Located just blocks from Plant Street, this updated home welcomes you with a charming front porch, beautiful mature trees and an oversized lot...nearly 1/4 acre & fully fenced. Fantastic & flexible floor plan with three bedrooms PLUS additional large flex space…office, den, gym, play room…endless options. Spacious foyer entry with storage and large living room with solid wood floors. Lots of natural light throughout. FULLY UPDATED KITCHEN in 2022...including cabinets, countertop & appliances. UPDATED TILE & HARDWOOD throughout. Large primary suite with vaulted ceiling, hardwood flooring & spacious ensuite bath with walk-in shower. Live the FLORIDA lifestyle outdoors in the large & private backyard with multiple patio areas, both covered & uncovered. Large storage shed. Long driveway for ample parking space. Zoned R-2. FULLY FENCED. NO HOA...live without rules & restrictions! Enjoy the lifestyle of Central Florida's most desirable and growing historic downtown...welcome to the GOLF CART LIFE, the West Orange Trail, HUGE weekly farmer's market, incredible annual festivals, shopping, dining, art gallery, the Crooked Can Brewery & Plant Street Market, parks & recreation...come JOIN THE FUN! Also conveniently located minutes from the Winter Garden Village shopping center and just minutes from HWY 429 with direct connect to the Turnpike and 408 for an easy commute to anywhere in Central Florida. DO NOT MISS your opportunity to own this one-of-a-kind dream home & LOCATION! WELCOME HOME!

524 S Highland Avenue, Winter Garden
234 N Lakeview Avenue, Winter Garden
$2,199,900
5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to The Birdhouse, one of Downtown Winter Garden's most iconic residences. Situated just blocks from Plant Street, the West Orange Trail, and the shores of Lake Apopka, this remarkable property offers a rare opportunity to own a thoughtfully restored home that seamlessly blends timeless architecture with modern luxury. Set on an expansive and highly coveted 0.51-acre lot, The Birdhouse delivers an unrivaled combination of character, sophistication, and downtown living. Originally built in 1920, this meticulously restored home preserves its historic charm through exposed brick walls, wood-beamed ceilings, vintage glass doorknobs, original lighting fixtures, multiple fireplaces, beautifully maintained hardwood floors and more. Natural light pours through original diamond-pane windows into the spacious family room, while the formal living and dining rooms showcase timeless character and thoughtful custom details. The chef's kitchen is a true focal point with a distinctive mix of old-world charm and modern design that combine luxury and function. Features include Cambria Portrush quartz countertops, custom floor-to-ceiling cabinetry, premium ZLINE appliances with an 8 burner gas stove range below exposed brick walls, a statement tile backsplash and custom range hood. Floating wood shelves, an expansive breakfast bar and cozy breakfast nook with built-in seating complete its design. A spacious mudroom and custom laundry room offer extensive cabinetry and counterspace for both storage and everyday convenience and a dedicated home office includes a custom built in desk. Set apart from the living areas and secondary bedrooms, the newly designed primary suite serves as a private sanctuary. Accessed through its own hallway, this spacious retreat features vaulted wood-paneled ceilings, an enormous walk-in closet, and a spa-inspired bath with dual vanities, two private water closets, a large glass-enclosed shower and elevated finishes throughout. Four additional generously sized bedrooms provide exceptional flexibility, including a second primary suite with dual closets and an ensuite bath, an additional ensuite bedroom overlooking the pool, and two bedrooms with a full guest bath positioned in between. The enormous fully fenced backyard is designed for year round enjoyment with a gas-heated saltwater sport pool, outdoor kitchen, expansive brick paved deck, detached covered lanai, and low-maintenance turf. Towering above it all is one of the property's most extraordinary features: a majestic 390-year-old oak tree, recognized as the oldest recorded oak tree in Orange County, providing unparalleled beauty and shade. Equally noteworthy, the home's original exterior waterspout remains in place and fully operational, offering a unique connection to the property's storied past. A double carport includes both a Tesla and golf cart charging station as well as a large storage closet equipped with power and a shop desk. Recent home improvements include a new roof (May 2026), updated PVC plumbing and drain field, new air handler, new tankless hot water heater, new water filtration system and new structural support trusses installed beneath the home to enhance long-term stability and strengthen the property's foundation for generations to come. A rare blend of historic significance, modern luxury, and premier location, The Birdhouse represents one of Downtown Winter Garden's most exceptional residential offerings. Schedule your private viewing today!

234 N Lakeview Avenue, Winter Garden
345 E Maple Street, Winter Garden
$295,000
2 Beds ⋅ 1 Baths ⋅ J W Jones Add SubDv. ⋅ 34787 Zip Code
VALUE IS IN THE LAND AND LOCATION! Discover the possibilities in an established Golf Cart Winter Garden neighborhood, conveniently located near historic Downtown Winter Garden, with its charming shops, restaurants, farmers market, and community events. Enjoy proximity to Plant Street and the city's planned East Winter Garden revitalization improvements. An existing tenant-occupied residence is situated on the property, with a roof approximately three years old (2023). Whether considering the existing residence or exploring future possibilities, this property offers an opportunity in a growing Central Florida community. Buyer to independently verify zoning, permitted uses, and highest and best use with the City of Winter Garden.

345 E Maple Street, Winter Garden
206 N Highland Avenue, Winter Garden
$1,050,000
3 Beds ⋅ 3 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. The roof was replaced in 2024, and the home features all-new electrical, plumbing, HVAC, and thoughtful renovations throughout while preserving the charm that makes historic homes so special. inside, you'll find a dedicated home office, inviting living spaces, and original character blended seamlessly with modern finishes and everyday functionality. Outside, two charming porches provide the perfect spots to enjoy your morning coffee, relax with friends, or take in the character of this established neighborhood. Location is everything, and this home puts you right in the heart of the Downtown Winter Garden lifestyle. Located within the highly sought-after Golf Cart District and in close proximity to Downtown Winter Garden, you can easily enjoy the weekly farmers market, seasonal festivals, local restaurants, boutique shops, entertainment, and community events. If you've been searching for a historic home in Winter Garden, a renovated Craftsman, a move-in-ready home with major systems already updated, a golf-cart-friendly property, or a home close to Downtown Winter Garden, this is a rare opportunity to enjoy historic charm without sacrificing modern comfort.

206 N Highland Avenue, Winter Garden
128 N Highland Avenue, Winter Garden
$965,000
4 Beds ⋅ 3 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to a piece of history, right in the Winter Garden's golf cart district! This stunning Craftsman bungalow is nestled in the Historic District, where timeless character meets extensive modern updates. Set on a 0.34-acre lot beneath grandfather oaks, this home creates an atmosphere that feels peaceful while placing you just steps from the energy of downtown. From the moment you arrive, you're greeted by a gravel driveway(2021) that leads to the front of the property, while outdoor lighting (2021) creates a welcoming glow as the sun goes down. Step through the beautiful leaded glass front door into a home filled with warmth and character. Rich heart pine floors, 9-foot ceilings, and crown molding create a timeless backdrop that is sure to make everyone feel at home.The front living and dining area provides a comfortable place to entertain or settle in with loved ones. Nearby, a flexible room can function as a bedroom or home office, and includes its own half bath, giving you the freedom to shape the space around your family's needs. At the center of the home, the farmhouse-inspired kitchen includes real wood cabinetry, granite countertops, and a convenient side entry to make everything from everyday cooking to hosting dinners feel effortless. The side entrance also makes bringing in groceries especially convenient. Down the hall, two bedrooms create comfortable retreats and share a guest bathroom with subway tile detailing. The guest bathroom tub drain line was replaced in 2025, while extensive flooring and subfloor improvements completed throughout the home provide a refreshed foundation from room to room. Upstairs, you’ll find the new flooring that was installed in 2025, along with recessed lighting (2018), and a bright and inviting loft space with flexibility for a reading area or home office. The primary bedroom was remodeled in 2025 and includes a custom built-in closet for exceptional organization. The upstairs bathroom was also remodeled in 2025, creating a beautifully updated space to begin and end your day. The home has received extensive upgrades, providing the new owners with peace of mind that this home was truly cared for. Upgrades include a downstairs HVAC system (2023), a replacement of the downstairs ductwork (2025), foundation support installed beneath the rear half of the home with concrete footers (2024), and a new water heater (2025). The home's exterior has been refreshed as well, including Artificial turf (2021) for easy upkeep, new exterior paint (Dec, 2024) and a new roof (2023). Heading outside, you're bound to love the private fenced in backyard space. Whether you're imagining weekend gatherings, letting little ones play, or simply enjoying a quiet afternoon outdoors, there's room to create the backyard you've always wanted. The detached 25' x 25' garage and workshop adds another layer of flexibility, complete with 100-amp electrical service. For a hobbyist, craftsman, or anyone who needs additional storage and workspace, this building can become whatever your lifestyle requires.This is a home with character you simply can't recreate, paired with the extensive updates and improvements. And perhaps best of all, you're living in the heart of Historic Downtown Winter Garden, where morning walks, farmers markets, local dining, shopping, live entertainment, and community events can become part of your daily routine. Don't wait on this amazing home, schedule your private showing TODAY!

128 N Highland Avenue, Winter Garden
325 W Newell Street, Winter Garden
$575,000
2 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code
**Click the Link for Virtual Tour** RARE TURNKEY OPPORTUNITY IN THE HEART OF DOWNTOWN WINTER GARDEN! Just three blocks from Plant Street and located within the golf-cart district, this beautifully renovated 2-bedroom, 2-bathroom cottage combines one of Winter Garden?s most sought-after locations with the flexibility of a primary residence, second home or established short term rental. Thoughtfully renovated down to the studs in 2016, the home blends historic cottage character with extensive modern improvements including updated electrical and plumbing, engineered hardwood floors, renovated kitchen and baths, double-pane windows, natural gas tankless water heater, metal roof and A/C was replaced in 2022. The open floor plan features a charming window seat in the living room, while the primary suite offers a walk-in closet and en-suite bath with dual sinks and oversized shower. A second full bath provides direct exterior access to the backyard - convenient for outdoor entertaining or future pool. Outside, the nearly quarter-acre fenced property offers something increasingly difficult to find this close to downtown: room to enjoy. Relax on the restored rear deck beneath the mature shade tree, utilize the approximately 200-sq.-ft. powered shed as storage, workshop or hobby space, and enjoy the convenience of a carport and additional outdoor space. Leave the car at home and walk, bike or take your golf cart to Plant Street, the West Orange Trail, Plant Street Market, Crooked Can, restaurants, boutiques, the farmers market, festivals and downtown entertainment. Currently operating as a successful short-term rental with reservations extending through March 2027, this property offers immediate income potential and exceptional flexibility. Whether you're searching for a downtown residence, vacation home or investment property, this is an opportunity to own a distinctive piece of the Downtown Winter Garden lifestyle.

325 W Newell Street, Winter Garden
113 W Division Street, Winter Garden
$455,000
4 Beds ⋅ 2 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
Fully Renovated and Move-In Ready! This beautiful 4-bedroom, 2-bath home features a spacious open-concept layout with bright and modern living areas. The designer kitchen showcases premium-quality cabinetry and elegant quartz countertops, perfect for both everyday living and entertaining. Enjoy relaxing in the screened porch or take advantage of the large backyard, ideal for gatherings, BBQs, or simply enjoying your outdoor space. A perfect blend of style, comfort, and functionality — don’t miss this opportunity!

113 W Division Street, Winter Garden
225 1st Street, Winter Garden
$288,000
3 Beds ⋅ 1 Baths ⋅ Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code
Charming 3-bedroom, 1-bath home in Winter Garden offering 1,020 sq. ft. of comfortable living space. This inviting home features a welcoming front porch, spacious living and dining areas, LVP flooring throughout the main living areas, and carpeted bedrooms. The kitchen is equipped with stainless steel appliances, including a refrigerator, range, and microwave. The upgraded bathroom adds a modern touch. Enjoy additional outdoor storage, a rear patio, and a large, fully fenced backyard—perfect for relaxing or entertaining. Conveniently located just minutes from Downtown Winter Garden, with its shops, restaurants, and entertainment. Close to West Oaks Mall and West Colonial Drive, providing easy access to shopping, dining, and major roadways.

225 1st Street, Winter Garden
208 3rd Street, Winter Garden
$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
208 3rd Street, Winter Garden
$435,000
Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code
Most Winter Garden listings sell on charm. This one sells on the rent roll. Eight rooms currently rented — seven at $175 weekly and one at $200 — generating $1,425 per week / $74,100 annualized gross income at current rents. In place, occupied, and income producing. The land adds another layer to the opportunity. Situated on approximately 0.22 acres / 9,500+ SF with a 75' x 125' lot, the fully fenced property offers R-2 zoning, no HOA, city water and city sewer, along with ample yard space and future flexibility. Hold the existing income while exploring the property's longer-term expansion or redevelopment potential, subject to applicable zoning requirements and City approvals. The location carries its own value. Just a few blocks from Historic Downtown Winter Garden, Plant Street, the West Orange Trail, shops, restaurants and the farmers market, with SR-429, Florida's Turnpike and Lake Apopka nearby. The surrounding area continues to evolve with renovated properties and new construction. 0.22 Acres. 9,500+ SF Lot. R-2. Eight Rented Rooms. $1,425/Week Gross. Income in place. Land underneath. Future upside ahead. A rare opportunity to own all three near Downtown Winter Garden—schedule your private showing today.

208 3rd Street, Winter Garden
1422 Basin Street, Winter Garden
$260,000
4 Beds ⋅ 1 Baths ⋅ Joe Louis Park SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome home to this quaint WINTER GARDEN gem, offering thoughtful updates throughout the property! It is freshly painted inside and out, and this inviting 4-bedroom, 1-bath home is move-in ready and waiting for its next homeowner. Updated vinyl flooring is installed throughout the home for creating a modern feel and easy maintenance. The bright kitchen features updated white cabinets, granite countertops, and new stainless appliances, creating a stylish but functional space. Additional updates include a newer water heater, updated HVAC, and new washer and dryer in the laundry closet. Utilize one of the four bedrooms as a a home office, home gym or hobby space. Conveniently located in desirable Winter Garden a historic citrus community located west of Orlando featuring brick-lined streets, unique local dining spots, and access to a variety of ecotourism and recreation. Call today to schedule your tour of this affordable opportunity to live in Central Florida. All information within the listing is intended to be correct and should be independently verified by buyer and buyer's agent(s).

1422 Basin Street, Winter Garden
368 N Boyd Street, Winter Garden
$774,900
4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Add 02 SubDv. ⋅ 34787 Zip Code
Exciting news for potential buyers! We've just reduced the listing price significantly and we're offering $10,000 in closing cost assistance or a rate buydown, your choice! This is a fantastic opportunity to make Winter Garden even more affordable! 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
689 Bethune Avenue, Winter Garden
$397,000
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
721 S Woodland Street, Winter Garden
$400,000
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
13619 Lake Boulevard, 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
1701 E Bay Street, Winter Garden
$289,000
2 Beds ⋅ 2 Baths ⋅ Joe Louis Park First Add SubDv. ⋅ 34787 Zip Code
Under contract-accepting backup offers. 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
20 E Division Street, Winter Garden
$985,000
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
420 E Cypress Street, Winter Garden
$400,000
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
15992 W Colonial Drive, Oakland
$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
17134 Lake Ingram Road, Winter Garden
$625,000
4 Beds ⋅ 2 Baths ⋅ Mt Park Orange Grove SubDv. ⋅ 34787 Zip Code
LAKEFRONT • 1.16 ACRES • NO HOA • A-1 ZONING • HORIZON WEST / WINTER GARDEN • CUSTOM HOME OPPORTUNITY! Rare lakefront property with over 1 acre in the highly desirable Horizon West/Winter Garden area. An exceptional opportunity for a custom home buyer, luxury home builder, developer or investor looking for a large waterfront homesite with NO HOA. Bring your custom home builder and create the lakefront home you've been dreaming about. The property offers exciting potential for a new construction luxury home, including the possibility of a multi-story modern home with balconies and a rooftop terrace designed to capture lake views, Florida sunsets, stargazing and Disney fireworks views. Existing home is located on the property. Buyer and builder to independently verify zoning, setbacks, building requirements, rooftop terrace feasibility, lakefront restrictions and intended use with the appropriate governing authorities.

17134 Lake Ingram Road, Winter Garden
205 Surprise Drive, Winter Garden
$1,200,000
4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
Welcome to Winter Garden, which has been ranked by Money Magazine "Best Places To Live In America" and is a finalist for Hallmark Channel's 2026 "Merriest Christmas Towns" Contest. This exceptional property in the heart of the 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. Priced to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. 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. A large shed, rated as a detached garage, 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. The 3/4 acre property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. SELLER WILL CONSIDER SUB-DIVIDINGTHE LOTS. 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
241 N Dillard Street, Winter Garden
$1,499,999
4 Beds ⋅ 3 Baths ⋅ J L Dillard Sub 3 SubDv. ⋅ 34787 Zip Code
Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

241 N Dillard Street, Winter Garden
18 & 20 E Plant 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
120 S Dillard 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

How much is your home worth?

Get instant property value now!