Under contract-accepting backup offers. Welcome to your own piece of Downtown Winter Garden paradise! This beautifully maintained 3-bedroom, 2.5-bathroom residence, built in 2019, offers the perfect blend of modern comfort, thoughtful design, and an unbeatable location just moments from one of Central Florida’s most sought-after historic downtowns.
Ideally situated just a short stroll from the award-winning Winter Garden Farmers Market, this exceptional home places you in the heart of one of Florida’s most vibrant communities. Walk to the renowned Crooked Can Brewing Company, Garden Theatre, boutique shopping, charming cafés, and an outstanding selection of local restaurants, wine bars, and entertainment venues. Whether enjoying a weekend brunch, an evening out, or one of the many community events held throughout the year, everything Downtown Winter Garden has to give is just minutes from your front door.
Inside, you’ll immediately appreciate the bright, open-concept layout designed for comfortable everyday living and effortless entertaining. The spacious kitchen overlooks the living and dining areas, creating a warm, inviting atmosphere where family and guests naturally gather. Featuring modern finishes, generous cabinetry, quality appliances, and ample counter space, the kitchen is ideal for casual meals or hosting dinner parties.
The highly desirable first-floor primary suite provides privacy and convenience with an en-suite bathroom and generous closet space. Also on the first floor are the laundry room, convenient half bath, and direct access to the attached two-car garage.
Upstairs are two additional well-proportioned bedrooms and a full bathroom, creating the ideal setup for family, guests, or a dedicated home office.
A standout feature is the dedicated surround-sound movie theatre, creating the ultimate in-home entertainment experience for movies, sporting events, and family movie nights.
Step outside to your own peaceful retreat. The recently created butterfly garden provides a colorful outdoor sanctuary, thoughtfully landscaped to attract butterflies and pollinators while creating the perfect place to relax with your morning coffee or unwind after a busy day.
Built in 2019, this home offers the advantages of modern construction, energy-efficient features, and low-maintenance living while combining timeless curb appeal with an exceptional floor plan.
Opportunities to own a newer home within minutes of Historic Downtown Winter Garden are rare. Whether you’re looking for a primary residence, a lock-and-leave lifestyle, or simply want to enjoy one of Central Florida’s most desirable communities, this property delivers an exceptional combination of location, comfort, and lifestyle.
Experience everything that makes Winter Garden one of Florida’s most celebrated places to live—from its tree-lined streets and award-winning Farmers Market to the renowned West Orange Trail, live entertainment, breweries, dining, shopping, and year-round community events—all just a short walk from your front door.
Agent is the Owner.
Ideally situated just a short stroll from the award-winning Winter Garden Farmers Market, this exceptional home places you in the heart of one of Florida’s most vibrant communities. Walk to the renowned Crooked Can Brewing Company, Garden Theatre, boutique shopping, charming cafés, and an outstanding selection of local restaurants, wine bars, and entertainment venues. Whether enjoying a weekend brunch, an evening out, or one of the many community events held throughout the year, everything Downtown Winter Garden has to give is just minutes from your front door.
Inside, you’ll immediately appreciate the bright, open-concept layout designed for comfortable everyday living and effortless entertaining. The spacious kitchen overlooks the living and dining areas, creating a warm, inviting atmosphere where family and guests naturally gather. Featuring modern finishes, generous cabinetry, quality appliances, and ample counter space, the kitchen is ideal for casual meals or hosting dinner parties.
The highly desirable first-floor primary suite provides privacy and convenience with an en-suite bathroom and generous closet space. Also on the first floor are the laundry room, convenient half bath, and direct access to the attached two-car garage.
Upstairs are two additional well-proportioned bedrooms and a full bathroom, creating the ideal setup for family, guests, or a dedicated home office.
A standout feature is the dedicated surround-sound movie theatre, creating the ultimate in-home entertainment experience for movies, sporting events, and family movie nights.
Step outside to your own peaceful retreat. The recently created butterfly garden provides a colorful outdoor sanctuary, thoughtfully landscaped to attract butterflies and pollinators while creating the perfect place to relax with your morning coffee or unwind after a busy day.
Built in 2019, this home offers the advantages of modern construction, energy-efficient features, and low-maintenance living while combining timeless curb appeal with an exceptional floor plan.
Opportunities to own a newer home within minutes of Historic Downtown Winter Garden are rare. Whether you’re looking for a primary residence, a lock-and-leave lifestyle, or simply want to enjoy one of Central Florida’s most desirable communities, this property delivers an exceptional combination of location, comfort, and lifestyle.
Experience everything that makes Winter Garden one of Florida’s most celebrated places to live—from its tree-lined streets and award-winning Farmers Market to the renowned West Orange Trail, live entertainment, breweries, dining, shopping, and year-round community events—all just a short walk from your front door.
Agent is the Owner.
Property Details
Price:
$1,099,000
MLS #:
S5154193
Status:
Active Under Contract
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
DOWNTOWN WINTER GARDEN
Neighborhood:
34787wintergardenoakland
Listed Date:
Jul 22, 2026
Finished Sq Ft:
2,700
Total Sq Ft:
3,485
Lot Size:
8,190 sqft / 0.18 acres (approx)
Year Built:
2020
See this Listing
Schools
Elementary School:
Dillard Street Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Disposal, Microwave
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Hardwood
Heating
Central, Electric
Interior Features
Open Floorplan, Primary Bedroom Main Floor, Walk-In Closet(s)
Laundry Features
Laundry Room
Levels
Two
Exterior
Architectural Style
Traditional
Attached Garage YN
1
Construction Materials
Block, Stucco, Wood Siding
Covered Spaces
2
Direction Faces
North
Exterior Features
French Doors, Sidewalk
Garage Spaces
2
Lot Features
City Lot, Sidewalk
New Construction YN
1
Parking Features
Covered, Garage Door Opener, Garage Faces Rear
Patio And Porch Features
Covered, Front Porch
Roof
Shingle
Financial
Tax Year
2026
Taxes
$12,866
Map
Community
- Address215 S HIGHLAND AVENUE WINTER GARDEN FL
- SubdivisionDOWNTOWN WINTER GARDEN
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Aug 29, 2026
827
Single Family Listed
112
Avg DOM
279
Avg $ / SqFt
$758,725
Avg List Price
Property Summary
- Located in the DOWNTOWN WINTER GARDEN subdivision, 215 S HIGHLAND AVENUE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $1,099,000 and features 3 beds, 3 baths, and has approximately 2,700 square feet of living space, and was originally constructed in 2020. The current price per square foot is $407. The average price per square foot for Single Family listings in WINTER GARDEN is $279. The average listing price for Single Family in WINTER GARDEN is $758,725. To schedule a showing of MLS#s5154193 at 215 S HIGHLAND AVENUE in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of REAL BROKER, LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 215 S HIGHLAND AVENUE
WINTER GARDEN, FL
