For Sale
Price CutPrice Drop: $50K (09/29)
Open House
Single family home for sale at 206 N Highland Ave, Winter Garden, FL 34787 | MLS# O6444632 | Listing updated on 2026-10-22
Photo 1 of Single family home for sale at 206 N Highland Ave, Winter Garden, FL 34787 | MLS# O6444632 | Listing updated on 2026-10-22
Photo 2 of Single family home for sale at 206 N Highland Ave, Winter Garden, FL 34787 | MLS# O6444632 | Listing updated on 2026-10-22
Photo 3 of Single family home for sale at 206 N Highland Ave, Winter Garden, FL 34787 | MLS# O6444632 | Listing updated on 2026-10-22
Photo 4 of Single family home for sale at 206 N Highland Ave, Winter Garden, FL 34787 | MLS# O6444632 | Listing updated on 2026-10-22
41+
Beds Icon

Virtual Tour

Beds Icon

Street View

$1,050,000

Monthly Est:$5,226

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon1,880sqft

206 N Highland Ave, Winter Garden, FL 34787

$5,226/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1925

  • $-- HOA

  • 10,488 sqft lot

  • $559/sq.ft

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.

  • Houzeo last checked: 3 hours ago
  • Listing updated: October 22, 2026 at 12:19 pm
  • Listing Provided by: Erica Diaz (407) 897-5400 , Mallory Guarino | HOMEVEST REALTY (407) 897-5400
  • Source: Stellar MLS-FL | MLS#: O6444632 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Orange County

  • City

    Winter Garden

  • Neighborhood

    --

  • Year Built

    1925

  • HOA Fees

    -

  • Finished Area

    1,880 sqft

  • Lot Size

    10,488 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6444632

  • MLS Status

    Active

  • Days on Market

    22

  • Cumulative Days on Market

    23

Open House

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

Interior

  • Appliances

    Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator

  • Interior Features

    Built In Features, Kitchen/family Room Combo, Living Room/dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Walk In Closet(s)

  • Cooling

    Central Air

  • Exterior Features

    Lighting

  • Sewer

    Public Sewer

  • Flooring

    Ceramic Tile, Wood

  • Heating

    Central

Construction

  • Year Built

    Year Built: 1925

  • Home type

    Single Family Residence

  • Architectural Style

    Craftsman, Historic

  • Foundation Details

    Crawlspace

  • Roof

    Shingle

  • Construction Materials

    Wood Siding

Utilities & Energy

  • Water Source

    Public

  • Utilities

    Electricity Connected, Natural Gas Available, Water Connected

  • Fireplace Features

    Family Room, Gas, Masonry, Non Wood Burning

  • Laundry Features

    Inside, Laundry Room

Other Features

  • Vegetation

    Mature Landscaping

  • Patio And Porch Features

    Covered, Front Porch, Porch, Rear Porch

  • Lot Features

    Historic District, City Limits, Paved

  • Subdivision Name

    Cooper & Sewell Add

Price History

DateEventPrice

10/13/2026

Source: mls_logoStellar MLS-FL #MFRO6444632

Price Decreased

$1,050,000 -4.55%

$559/sqft

09/29/2026

Source: mls_logoStellar MLS-FL #MFRO6444632

Listed for Sale

$1,100,000

$585/sqft

09/29/2026

Source: mls_logoStellar MLS-FL #MFRO6444632

Price Increased

$1,100,000 +124.49%

$585/sqft

08/01/2025

Source: mls_logoStellar MLS-FL #MFRO6314888

Sold

$490,000 -5.77%

$261/sqft

07/15/2025

Source: mls_logoStellar MLS-FL #MFRO6314888

Pending

$520,000

$277/sqft

Show more

Nearby Homes

Based on information from Stellar MLS® through Oct 22, 2026, 03:45PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

Advertising Broker: Fred McGill | Simple Showing, Inc