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Property for sale at 206 N HIGHLAND AVENUE, WINTER GARDEN, FL, 34787
Property for sale at 206 N HIGHLAND AVENUE, WINTER GARDEN, FL, 34787
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206 N Highland AvenueWinter Garden, FL, 34787

3beds
3baths
1,950sqft
Single Family Residence
Built in 1925
$1,100,000
For sale
Price per sqft
$564
Days on market
9
Listed Sep 29, 2026
MLS #O6444632Updated Oct 6, 2026

About this property

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.

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Property details

Property type
Single Family Residence
Street address
206 N Highland Avenue
City
Winter Garden
State
FL
ZIP code
34787
Year built
1925
New construction
No
Faces
West
Rooms
10
Living area
1,950 sqft
Total building area
2,326 sqft
Architectural style
Craftsman
Levels
One

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 12:01 AM EDT

Price & sale history

EventPrice
Listed for saleMLS #O6444632$1,100,000
SoldMLS #O6314888$490,000
Price reducedMLS #O6314888$520,000Change: −5%−$27,500
Listed for saleMLS #O6314888$547,500
History may be incomplete.
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Property for sale at 206 N HIGHLAND AVENUE, WINTER GARDEN, FL, 34787
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