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.
Property Details
Price:
$1,050,000
MLS #:
O6444632
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
COOPER & SEWELL ADD
Neighborhood:
34787wintergardenoakland
Listed Date:
Sep 29, 2026
Finished Sq Ft:
1,880
Total Sq Ft:
2,326
Lot Size:
10,488 sqft / 0.24 acres (approx)
Year Built:
1925
See this Listing
Schools
Elementary School:
Dillard Street Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Hardwood
Heating
Central
Interior Features
Built-in Features, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Architectural Style
Craftsman, Historical
Construction Materials
Wood Siding
Covered Spaces
1
Direction Faces
West
Exterior Features
Lighting
Garage Spaces
1
Lot Features
Historic District, City Lot
Patio And Porch Features
Covered, Front Porch, Porch, Rear Porch
Roof
Shingle
Financial
Tax Year
2025
Taxes
$2,054
Map
Community
- Address206 N HIGHLAND AVENUE WINTER GARDEN FL
- SubdivisionCOOPER & SEWELL ADD
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Oct 19, 2026
806
Single Family Listed
120
Avg DOM
278
Avg $ / SqFt
$744,002
Avg List Price
Property Summary
- Located in the COOPER & SEWELL ADD subdivision, 206 N HIGHLAND AVENUE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $1,050,000 and features 3 beds, 3 baths, and has approximately 1,880 square feet of living space, and was originally constructed in 1925. The current price per square foot is $559. The average price per square foot for Single Family listings in WINTER GARDEN is $278. The average listing price for Single Family in WINTER GARDEN is $744,002. To schedule a showing of MLS#o6444632 at 206 N HIGHLAND AVENUE in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of HOMEVEST REALTY. 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. 206 N HIGHLAND AVENUE
WINTER GARDEN, FL