About This Home

This 3-bedroom, 3-bathroom single family at 206 N HIGHLAND Avenue in Winter Garden, FL is listed for $999,999 ($532 per sqft). Built in 1925, the home offers 1,880 sqft of living space on a 0.24 acres lot.

Key Features

  • Built in 1925
  • 0.24 acre lot
  • Fireplace

Property Details

1 story
2 full, 1 half
1-car garage
1925

Amenities

FireplaceA/C
Listing Description

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.

Monthly Cost Estimate

$5,348/mo

20% down · 6.5% · 30 years

Principal$723
Interest$4,333
Insurance$292

Estimates only. Actual payments may vary.

Location

206 N HIGHLAND Avenue

Winter Garden, FL 34787

COOPER & SEWELL ADD

Features & Amenities

Interior Features

Built-in FeaturesKitchen/Family Room ComboLiving Room/Dining Room ComboPrimary Bedroom Main FloorStone CountersWalk-In Closet(s)

Exterior Features

Lighting

Property Details

Flooring

WoodTile - Ceramic

Construction

Wood Siding

Outdoor Features

Porch

Heating

Central

Cooling

Central Air

Appliances

DishwasherDisposalElectric Water HeaterMicrowaveRangeRange HoodRefrigerator

Questions & Answers

This 3-bedroom, 3-bathroom single family at 206 N HIGHLAND Avenue is listed at $999,999 ($532/sqft). The estimated monthly payment is $5,349 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1925, 0.24 acre lot, Fireplace. Interior Features: Built-in Features, Kitchen/Family Room Combo, Living Room/Dining Room Combo. Exterior Features: Lighting.

This property is listed by Erica Diaz.

ED

Erica Diaz

Agent at Homevest Realty

Listed by Homevest Realty · Broker phone: (407) 897-5400 · View on Broker Site · Broker website

MLS# O6444632· Source: Stellar MLS· 33 days on PropertySimple

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

206 N HIGHLAND Avenue, Winter Garden, FL 34787

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