Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Living Area Square Feet: 1000 to 1499
Do Not Show Listings
Winter Garden - 16 properties found
306 DANIELS POINTE DR, WINTER GARDEN, FL 34787
$310,000115 Days on yellowkey MLS ID: O6371413
0 Days Off yellowkey (back on 3/18/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1326 Built: 1999Monthly Fee: $78 Tax: $4,120 (2024)Community: Daniels CrossingSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,120
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. This charming 3 bedroom, 2 bath home offers a fantastic opportunity to make it your own. Featuring a fully fenced backyard, the property provides privacy and plenty of space for outdoor living, pets, or entertaining. Located just a short distance from Winter Garden Village and historic Plant Street, you’ll enjoy easy access to shopping, dining, and local events. With so much potential, this home is perfect for buyers looking to add their personal touch in a highly desirable location.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Claire Jesso (407-436-5039)
236 DONALD DR, WINTER GARDEN, FL 34787
$465,00010 Days on yellowkey MLS ID: O6401940
2 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1080 Built: 1930 Tax: $410 (2025)Community: Showalter ParkSingle Family
Taxes:$410
Elementary School: Dillard Street Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Calling all buyers, builders, and investors, this is a rare opportunity to secure land with no HOA in the heart of Downtown Winter Garden. Located within the highly sought after Golf Cart District, just 0.5 miles from the iconic Plant Street Market, seconds from the West Orange Trail, and with convenient access to the Florida's Turnpike, this spacious quarter acre lot offers the ultimate combination of freedom, location, and connectivity. Set on a private street, this property is the perfect canvas to build your custom dream home without restrictive guidelines or additional monthly fees. With an existing structure already on site, electricity, water, and essential utilities are already in place, making the building process significantly easier, faster, and more cost effective. Whether you envision a modern custom estate, a charming bungalow, or an investment opportunity, the flexibility here is unmatched. Enjoy the ability to walk, bike, or golf cart to everything downtown has to offer, while being positioned in an area experiencing exciting growth with new dining, retail, and commercial development continuing to expand throughout Winter Garden. Opportunities like this, a no HOA quarter acre lot in the Golf Cart District with prime access and growth around it, rarely come available. This is your chance to build exactly what you have been dreaming of in one of Central Florida’s most desirable and rapidly evolving communities.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Lauren Bouchard (352-978-6837)
113 W DIVISION ST, WINTER GARDEN, FL 34787
$549,9906 Days on yellowkey MLS ID: S5148787
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1487 Built: 1951 Tax: $4,920 (2025)Community: Winter Garden Shores RepSingle Family
Taxes:$4,920
Remarks: 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!
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Marcelo Garrido (321-388-1824)
15187 HARROWGATE WAY, WINTER GARDEN, FL 34787
$450,00018 Days on yellowkey MLS ID: TB8497081
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1296 Built: 2003Monthly Fee: $46 Tax: $5,808 (2025)Community: Stone CrkSingle Family
Taxes:$5,808
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Maria Howard (410-422-3518)
636 S PARK AVE, WINTER GARDEN, FL 34787
$298,90016 Days on yellowkey MLS ID: O6400433
3 Days Off yellowkey (back on 4/25/2026)
Bed: 4 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1272 Built: 1953 Tax: $3,751 (2025)Community: BurchshireSingle Family
Taxes:$3,751
Remarks: Under contract-accepting backup offers. Location! Location! This 4 bedroom 1 1/2 bath Winter Garden home is a block away from Veterans Memorial Park, and close to Downtown Historic Winter Garden. Home appears larger than records indicate, and has 4 full bedrooms and 1 1/2 baths. Almost 1/4 Acre Lot (.22). Newer roof (2021), Newer A/C, Newer Kitchen with Wood Cabinets, Granite, and SS Appliances. Tile floors in Great Room, and wood laminate floors in bedrooms. Large 544 Sq Ft 2 Car Garage with Work Shop Area. Large partially fenced lot.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: David Kravitz (407-656-7653)
632 DHARMA CIR, WINTER GARDEN, FL 34787
$380,00031 Days on yellowkey MLS ID: O6396151
1 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1315 Built: 2000Monthly Fee: $78 Tax: $5,780 (2025)Community: Daniels Crossing Ph 03Single Family
Taxes:$5,780
Remarks: Located in Winter Garden, this 3-bedroom, 2-bath home features a private in-ground pool and a solar energy system. The home includes a new A/C unit, stainless steel appliances, and an extended driveway for guests. The pool (28’ x 15’) offers a screened enclosure, lighting, auto cleaner, child safety fence, and is both saltwater and solar-heated—perfect for year-round enjoyment. The home has a Screened in Patio. There is an underground drainage next to the pool for the overflow. Conveniently located near Highway 429 and the Florida Turnpike, with easy access to Winter Garden Village, Disney, the West Orange Trail, and Publix. Please schedule showings in advance.
Listing is courtesy of: LA ROSA RTY WINTER GARDEN LLC (407-614-5158)
Listing Agent: Edul Mohamed, Pa (407-760-0090)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,00017 Days on yellowkey MLS ID: O6396654
1 Days Off yellowkey (back on 4/23/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1235 Built: 1986Monthly Fee: $7 Tax: $5,354 (2025)Community: Kings BaySingle Family
Taxes:$5,354
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in this charming 3-bedroom, 2-bath ranch-style home, perfectly positioned on a spacious corner lot in one of Winter Garden’s most desirable areas. With its single-story layout and inviting curb appeal, this home offers both comfort and convenience in a relaxed, open setting. Step inside to discover a bright and functional floor plan designed for everyday living and effortless entertaining. The generous living spaces flow seamlessly, while ample natural light enhances the home’s warm and welcoming feel. The split-bedroom design provides privacy, with a well-appointed primary suite and comfortable secondary bedrooms. Outside, the oversized corner lot offers endless possibilities—plenty of room for outdoor gatherings, gardening, or simply enjoying the Florida sunshine. Located well within the golf cart district, you’re just a short ride from the charm and energy of historic downtown Winter Garden. Enjoy easy access to local shops, dining, community events, and the popular weekly farmers market, all just minutes from your doorstep. This is a rare opportunity to own a beautifully situated home that combines classic ranch-style living with an unbeatable location. Call Today!
Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)
Listing Agent: Jim Kernohan (407-450-3861)
604 FOSTER AVE, WINTER GARDEN, FL 34787
$400,00023 Days on yellowkey MLS ID: O6389095
0 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1275 Built: 1975 Tax: $1,633 (2024)Community: Westchester PlaceSingle Family
Taxes:$1,633
Elementary School: Tildenville Elem
Remarks: Under contract-accepting backup offers. Situated just two blocks outside the Golf Cart District and directly across from Veterans Memorial Park, this property offers a lifestyle that blends convenience, privacy, and outdoor living. BRAND NEW ROOF JUST INSTALLED! (April 2026, 10-yr warranty) Set on a rare double lot, the home welcomes you with mature landscaping, an orchid tree in the front yard, stylish Bermuda hurricane shutters, and a covered front porch that provides a charming place to relax and enjoy the neighborhood. Inside, the spacious layout features durable porcelain wood-grain tile flooring installed in 2017, a bright living area, and a generous kitchen designed for everyday functionality and gathering. Major updates provide peace of mind, including all new double-pane windows installed in 2021, a water heater replaced in 2020, HVAC from 2019 (installed 2021) under warranty with American Air & Heat, and upgraded WiFi. Outside is where the property truly shines. The fully fenced backyard offers exceptional privacy with mature landscaping, fruit trees including kumquat, green apple, mango, and pineapple, along with bananas, plantains, pecan, and raised herb beds featuring aloe, basil, spearmint, and Italian oregano. Entertain or unwind on the recently resealed paver patio or under the pergola, while the powered shed with custom shelving and ramp provides flexible space for hobbies or storage. Additional features include a large private driveway, gutters, double weather-stripped front doors, and a chicken coop. With extensive updates, functional living space, and a backyard designed for gardening, relaxing, and entertaining, this home offers a unique opportunity to enjoy both comfort and outdoor lifestyle.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Jackie Isham (407-917-8954)
375 REGAL DOWNS CIR, WINTER GARDEN, FL 34787
$334,90068 Days on yellowkey MLS ID: O6377205
0 Days Off yellowkey (back on 3/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1464 Built: 2001 Tax: $4,413 (2024)Community: Regal Pointe Ph 01 43/129Single Family
Taxes:$4,413
Elementary School: Maxey Elem
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 3-bedroom, 2-bathroom home with a two-car garage in the heart of the Regal Pointe subdivision of Winter Garden. Upon entry, you are welcomed by the large kitchen overlooking the living room, embracing open-concept living. The kitchen features laminate countertops, a tile backsplash, a breakfast eating area, and stainless steel Whirlpool appliances. The primary bedroom offers a private retreat, situated on the opposite side of the house from the secondary bedrooms. The large, open living room provides sliding door access to a screened-in patio with a peaceful pond view, making it the perfect place to enjoy a morning coffee or evening drink. You’re conveniently located within 25 minutes of Orlando’s theme parks, the airport, and downtown Orlando. Schedule your showings today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
14804 COSCESTER ST, WINTER GARDEN, FL 34787
$399,990263 Days on yellowkey MLS ID: O6333959
1 Days Off yellowkey (back on 4/16/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1456 Built: 2025 Tax: $1,129 (2024)Community: Black LakeSingle Family
Taxes:$1,129
Remarks: 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.
Listing is courtesy of: KARDOSH REALTY (407-499-4466)
Listing Agent: Stephanie Li (407-538-7599)
483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787
$339,90020 Days on yellowkey MLS ID: O6398208
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1988 Tax: $2,702 (2025)Community: East Garden Manor Add 03Single Family
Taxes:$2,702
Remarks: Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roff, new pluming, close to major roads, schools, minutes to Winter Garden dawn town.
Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)
Listing Agent: Rosa Rodriguez (407-832-1185)
238 N MAIN ST, WINTER GARDEN, FL 34787
$600,00026 Days on yellowkey MLS ID: O6397340
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1005 Built: 1950 Tax: $5,389 (2025)Community: Orange Grove SubSingle Family
Taxes:$5,389
Remarks: **** HEART OF DOWTOWN WINTER GARDEN **** CAN'T GET MUCH CLOSER TO ***HISTORIC DOWNTOWN WINTER GARDEN *** THAN THIS! SERIOUSLY! FRESH OWNER REDO WITH DISCERNING DESIGN CHOICES ON THIS SOLID & ADORABLE 3 BEDROOM/2 BATH FENCED YARD (SOLID CONCRETE BLOCK) CHARMER. *** NO HOA OR FEES*** HOOOORAY! & WITHIN STEPS TO DOWNTOWN PLANT STREET, TONY'S, HARLOW GROVE RESTAURANT, CHURCHES, FARMERS MARKET, CROOKED CAN FOOD HALL, JESSIE BROCK COMMUNITY PARK, PUBLIC BOAT RAMP AT NEWTON PARK, AND ALL THAT FAST GROWING DOWNTOWN HISTORIC WINTER GARDEN HAS TO OFFER!!! AMAZING CHANGES ARE ON THE HORIZON!!!----GET IN ON YOUR OWN LOCKED IN LOCATION NOW!!!----- (LOCATED WITHIN THE ZONED GOLF CART DISTRICT). WITHIN MINUTES TO HWY 50, FOWLER GROVES/LOWES/TARGET & 429 FREEWAY ENTRANCE, AS WELL AS FLORIDA TURNPIKE AND E-W EXPRESSWAY ENTRANCES BEING MERE MINUTES AWAY ON EAST PLANT STREET; OH SO CENTRALLY LOCATED DIRECTLY IN "TOWN PROPER" JUST A FEW LOTS UP FROM PLANT STREET; & JUST A LITTLE FURTHER DOWN MAIN STREET AND YOU ARE AT THE PUBLIC BOAT RAMP, NEWTON PARK AND THE FARNSWORTH CITY POOL!!! BEYOND EXCELLENT ACCESS TO MULTIPLE GROCERIES, TAILORS & SHOPPING OPTIONS AT HWY 50, PARK AVENUE, DILLARD STREET AND NEARBY OAKLAND! ALSO, THE WEST ORANGE TRAIL RUNS PERPENDICULAR TO MAIN STREET (YOUR STREET) & IS STEPS FROM YOUR HOME-----CONCRETE BLOCK CONSTRUCTION BUILT W/TERMITE BOND/MONTHLY PEST TREATMENT-ALL WITH MASSEY SENTRICON & TRANSFERABLE BOND TO THE NEW OWNER--- HOME HAS GROOMED MATURE OAKS WITH FENCED IN BACK YARD (WOOD PLANK AND VINYL) WITH ELEVATED WOOD DECK FOR FLIPPING OPEN THE BRAND NEW DOUBLE FRENCH DOORS AND ENJOYING FOR ENTERTAINING!!! ***EXCELLENT VALUE/EXCELLENT LOCATION/GOLF CART DISTRICT/NO HOA!***--WHY RENT WHEN YOU CAN (OWN) YOUR OWN PROPERTY FOR JUST A FEW BUCKS MORE PER MONTH? -----HOME WARRANTY OPTIONS AVAILABLE. WITHIN ZILLOW RANGE PRICING! GREAT DEAL. COME SEE FOR YOURSELF...........
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Jason Fulmer (321-303-6670)
13147 SUBURBAN TER, WINTER GARDEN, FL 34787
$245,00033 Days on yellowkey MLS ID: G5110298
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1479 Built: 1971Monthly Fee: $15 Tax: $4,142 (2025)Community: Suburban ShoresSingle Family
Taxes:$4,142
Remarks: Call for HIGHEST and BEST - Wednesday 4-8-2-26 at 7:00 PM!!! Fixer Upper!! Located in one of Winter Garden's older, established neighborhoods with deeded lake access to the beach. This house was built in 1971 using old-fashioned construction, and it is said to be very solid. This house is a 2/2 with large bedrooms, two nice baths, and an oversized living room with a brick fireplace. As you enter the property, to the right is the dining room, then the kitchen, and the garage entrance. Single-car garage, with a door to the nicely sized backyard. The pool was just recently drained, and originally had a diving board. The house has been vacant for many years, and the prolonged vacancy has damaged the roof. The screened pool lanai is large and will need updating. Don't overlook the sauna and the brick BBQ Grill along the side of the pool. This is a good opportunity to put a property back into order, creating a lovely residential property. Look up on FB, 'Suburban Shores Improvement Association'. So many photos of the community, gatherings, and fun times.
Listing is courtesy of: REALTEAM REALTY INC. (352-394-1144)
Listing Agent: Trish Leisner (352-267-6216)
514 DUNBAR AVE, WINTER GARDEN, FL 34787
$295,00033 Days on yellowkey MLS ID: O6394414
0 Days Off yellowkey (back on 4/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1162 Built: 2006 Tax: $2,616 (2025)Community: Joe Louis ParkSingle Family
Taxes:$2,616
Remarks: Under contract-accepting backup offers. Welcome to this charming and beautifully updated 3-bedroom, 2-bath bungalow located minutes from the heart of highly desirable Winter Garden! This move-in ready home offers the perfect blend of character, comfort, and modern upgrades—including a brand-new roof for peace of mind. Step inside to discover a warm and inviting layout with stylish updates throughout, creating a light and airy feel that’s perfect for both everyday living and entertaining. The cozy bungalow design offers functionality and charm, making it an ideal primary residence, second home, or investment opportunity. Living in Winter Garden means enjoying one of Central Florida’s most sought-after communities, known for its historic downtown, vibrant lifestyle, and strong sense of community. Just minutes away, you’ll find the award-winning Winter Garden Farmers Market, held every Saturday and featuring over 100 vendors, live music, and a lively, family-friendly atmosphere . Stroll along the charming brick-lined streets of downtown, filled with boutique shops, local dining, and cultural attractions. Don’t miss your opportunity to own this adorable, updated bungalow in one of Central Florida’s most beloved communities—schedule your private showing today!
Listing Agent: Tara Heard (407-637-4634)
1040 MAXEY DR, WINTER GARDEN, FL 34787
$250,00044 Days on yellowkey MLS ID: O6391395
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1184 Built: 1968Community: Bay St ParkSingle Family
Taxes:
Tax Year:
Remarks: Some properties check a box. This one opens a door. This 3-bed, 2-bath home in the heart of Winter Garden is more than a place to live. It's a wealth-building opportunity sitting in plain sight. The floor plan sets up beautifully for a duplex conversion: a 1/1 in the front and a 2/1 in the back. Live in one side and let your tenant cover the mortgage, or rent both and start building cash flow from day one. At approximately 1,184 sq ft, the footprint is manageable, the concept is proven, and the location makes it work. You're minutes from historic downtown Winter Garden, major shopping corridors, top dining, and highway access. The kind of address that attracts reliable tenants and holds long-term value in one of Orange County's strongest markets. House hacking, buy-and-hold, or straight investment play. However you run the numbers, this one makes sense. ROOF is 2020, WATER HEATER 2021 and HVAC 2016
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Phat Nguyen (407-452-8751)
884 KLONDIKE ST, WINTER GARDEN, FL 34787
$375,000 MLS ID: O6389922
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1485 Built: 2023Community: Loveless J S Add 01Single Family
Remarks: Welcome to Historic Winter Garden, Florida — No HOA! Where small-town charm, community, and modern living come together and you keep more of what's yours with no HOA fees. Built in 2023, this beautifully designed 4-bedroom, 2-bath home with a 1-car garage offers the perfect blend of contemporary comfort and timeless neighborhood character. Start your mornings on the inviting front porch, the ideal spot for coffee, fresh air, and easy neighborhood conversations. Step inside to an open-concept layout that feels bright, spacious, and instantly welcoming, whether you're hosting friends or enjoying a quiet evening in. The modern kitchen impresses with granite countertops, sleek cabinetry, and generous workspace, flowing seamlessly into the main living areas. Laminate flooring throughout the main living spaces adds a clean, low-maintenance finish. Beyond your front door, downtown Winter Garden is just minutes away, one of Central Florida's most beloved historic districts. Spend your weekends at the popular Saturday Farmers Market, dining at local restaurants ranging from cozy cafés to fine dining, or soaking in the seasonal festivals and community events that give this area its unmistakable energy. Newer construction. Modern finishes. A welcoming, active community. And no HOA. This Winter Garden gem checks every box, so don't miss your chance to make it yours.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nicole Mickle (407-353-0826)
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