About 206 N Highland Avenue
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.
Open House
Features of 206 N Highland Avenue
| MLS® # | O6444632 |
|---|---|
| Price | $1,100,000 |
| Bedrooms | 3 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 1,950 |
| Acres | 0.24 |
| Year Built | 1925 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Craftsman, Historical |
| Status | Active |
Community Information
| Address | 206 N Highland Avenue |
|---|---|
| Area | Winter Garden/Oakland |
| Subdivision | COOPER & SEWELL ADD |
| City | WINTER GARDEN |
| County | Orange |
| State | FL |
| Zip Code | 34787 |
Amenities
| # of Garages | 1 |
|---|---|
| Is Waterfront | No |
| Has Pool | No |
Interior
| Interior Features | Built-in Features, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s) |
|---|---|
| Appliances | Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator |
| Heating | Central |
| Cooling | Central Air |
| Fireplace | Yes |
| Fireplaces | Family Room, Gas, Masonry, Non Wood Burning |
Exterior
| Exterior Features | Lighting |
|---|---|
| Lot Description | Historic District, City Lot |
| Roof | Shingle |
| Foundation | Crawlspace |
School Information
| Elementary | Dillard Street Elem |
|---|---|
| Middle | Lakeview Middle |
| High | West Orange High |
Additional Information
| Date Listed | September 29th, 2026 |
|---|---|
| Zoning | R-2 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | HOMEVEST REALTY |
|---|