206 N HIGHLAND AVENUE, MLS# – O6444632

206 N HIGHLAND AVENUE
Residential $1,100,000.00 - Single Family Residence
1950 Square Feet 3 Bedrooms 2.5 Bathrooms 1 Garage 1925 Year Built 0.24 Square Feet

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.

Additional Details

  • Elementary School: Dillard Street Elem
  • Middle Or Junior School: Lakeview Middle
  • High School: West Orange High
  • Architectural Style: Craftsman, Historical
  • Baths Full: 2
  • Baths Half: 1
  • Modification Timestamp: 2026-09-30T08:36:06.378Z
  • Building Area: 2326
  • Cooling: Central Air
  • Days on the Market: 1
  • Direction Faces: West
  • Directions: From Plant Street, head north on N Highland. Home will be on the left.
  • Fireplace Features: Family Room, Gas, Masonry, Non Wood Burning
  • Flooring: Ceramic Tile, Hardwood
  • Foundation Details: Crawlspace
  • Furnished: Unfurnished
  • Heating: Central
  • Laundry Features: Inside, Laundry Room
  • Levels: One
  • List Agent Email: [email protected]
  • List Agent: Erica Diaz
  • List Agent Phone: 407-897-5400
  • List Office: HOMEVEST REALTY
  • List Office Phone: 407-897-5400
  • Listing Terms: Cash, Conventional, FHA, VA Loan
  • Lot Features: Historic District, City Lot
  • MLS Area Major: 34787 - Winter Garden/Oakland
  • MLS Status: Active
  • Modification Time Stamp: 2026-09-30T05:16:55.027Z
  • Roof: Shingle
  • Source System: 812313959
  • Status Change Time: 2026-09-29T17:00:45.233Z
  • WaterSource: Public
  • Zoning: R-2
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30 Years Fixed, 3.5% Interest
  • Principle and Interest

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Julia Roberts