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206 N HIGHLAND AVENUE, WINTER GARDEN, FL - photo 1

$1,050,000

206 N HIGHLAND AVENUE

WINTER GARDEN, FL 34787

Estimated payment $5,884/month

no HOA · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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3Beds
3Baths
1,880Sq Ft
$559Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

No HOA
Fireplace
Garage
Built in 1925
10,488 sqft Lot

About This Home

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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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:3
  • •Bathrooms:3
  • •Full bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:1,880 sqft
  • •Total interior livable area:1,880 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:10,488 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1925

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Price history

DateEventPrice
2026-09-29T00:00:00.000ZListed for sale$1,050,000$559/sqft

Listing Agent

Erica Diaz

HOMEVEST REALTY

Brokerage Phone: 407-897-5400

Source: Stellar MLS · MLS #O6444632

Data Powered by Home Junction, Inc.

Nearby

Schools

WILLIAM S MAXEY ELEMENTARY

Elementary · 1.1 mi

ORANGE TECHNICAL COLLEGE WEST CAMPUS

High · 1.2 mi

WEST ORANGE HIGH

High · 2.3 mi

Supermarkets

Mundaze

1.0 mi

Horizon Foods Brokers

1.4 mi

Dining

Sugar Rush Marshmallows

0.8 mi

Daniel's Cheesesteak House

1.0 mi

The BreakRoom

1.3 mi

Parks

Irrgain Park

0.7 mi

Beaches

Conrad Beach

11.7 mi

West Beach

11.7 mi

East Beach

11.8 mi

Nearby amenity locations include data © OpenStreetMap contributors.