206 N HIGHLAND AVENUE
Winter Garden, FL 34787
$1,050,000
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.
Listing Courtesy of: HOMEVEST REALTY
407-897-5400
| Listing Id: | O6444632 |
|---|---|
| List Price: | $1,050,000 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Active |
| Bedrooms Total: | 3 |
| Bathrooms Full: | 2 |
| Bathrooms Half: | 1 |
| Living Area: | 1,880 |
| Tax Annual Amount: | $2,054 |
| Lot Size Square Feet: | 10,488 |
| Lot Size Acres: | 0.24 |
| Architectural Style: | Craftsman, Historic |
| Waterfront?: | No |
| City: | Winter Garden |
| County Or Parish: | Orange |
| Subdivision Name: | Cooper & Sewell Add |
| Postal Code: | 34787 |
| Year Built: | 1925 |
| Appliances: | Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator |
| Bathrooms Total Integer: | 3 |
| Building Area Source: | Public Records |
| Building Area Total: | 2326 |
| Building Area Units: | Square Feet |
| Direction Faces: | West |
| Foundation Details: | Crawlspace |
| Construction Materials: | Wood Siding |
| Cooling: | Central Air |
| Fireplace Features: | Family Room, Gas, Masonry, Non Wood Burning |
| Directions: | From Plant Street, head north on N Highland. Home will be on the left. |
| Elementary School: | Dillard Street Elem |
| Exterior Features: | Lighting |
| Flooring: | Ceramic Tile, Wood |
| Furnished: | Unfurnished |
| Garage Spaces: | 1 |
| Garage?: | Yes |
| Heating: | Central |
| High School: | West Orange High |
| 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 |
| Ownership: | Fee Simple |
| Living Area Source: | Owner |
| Living Area Units: | Square Feet |
| Lot Features: | Historic District, City Limits, Paved |
| Lot Size Acres: | 0.24 |
| Middle Or Junior School: | Lakeview Middle |
| MLS Area Major: | 34787 - Winter Garden/Oakland |
| MLS Area Major: | 34787 - Winter Garden/Oakland |
| Original List Price: | $1,100,000 |
| Parcel Number: | 14-22-27-1728-04-020 |
| Patio And Porch Features: | Covered, Front Porch, Porch, Rear Porch |
| Pets Allowed: | Yes |
| Township: | 22 |
| Road Surface Type: | Paved |
| Roof: | Shingle |
| Listing Terms: | Cash, Conventional, FHA, VA Loan |
| Tax Year: | 2025 |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Utilities: | Electricity Connected, Natural Gas Available, Water Connected |
| Water Source: | Public |
| Public Survey Range: | 27 |
| Public Survey Section: | 14 |
| Zoning: | R-2 |
| Vegetation: | Mature Landscaping |
| Additional Lease Restrictions: | Please verify with the City of Winter Garden |
| Additional Rooms: | Den/Library/Office, Inside Utility |
| Available For Lease Yn: | Yes |
| Building Area Total Srch Sq M: | 216.09 |
| Calculated List Price By Calcula: | 558.51 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6444632?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6444632?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | x |
| Green Verification Count: | 0 |
| Homestead Yn: | No |
| Lease Restrictions Yn: | Yes |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 174.66 |
| Lot Size Square Meters: | 974 |
| Minimum Lease: | 8-12 Months |
| Realtor Info: | As-Is, Floor Plan Available, Sign |
| Room Count: | 10 |
| Sdeo yn: | No |
| Total Acreage: | 0 to less than 1/4 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-897-5400 |
| Originating System Name : | Stellar MLS |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-09-29 |
| Fireplace?: | Yes |
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Property Last Updated: October 21, 2026 08:54 AM - ET
