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$1,100,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,950 Sq. Ft.
  • Updated 1 day ago

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Open House: 12:00 PM - 2:00 PM

Saturday 10/3 12:00 PM - 2:00 PM

206 N Highland Avenue,Winter Garden, FL 34787

206 N Highland AvenueWinter GardenFL34787

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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.

Full Property Details for 206 N Highland Ave

General

  • Price: $1,100,000
  • Taxes: $2,054 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6444632
  • Updated: 9/30/2026
  • Added to Site: 3 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 10
  • Interior Features: Built-in Features, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Family Room, Gas, Masonry, Non Wood Burning
  • Appliances: Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room

Exterior

  • Exterior Features: Lighting
  • Deck/Patio: Covered, Front Porch, Porch, Rear Porch
  • Porch/Patio/Deck: Covered, Front Porch, Porch, Rear Porch

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Covered Spaces: 1

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: COOPER & SEWELL ADD
  • Driving Directions: From Plant Street, head north on N Highland. Home will be on the left.
  • Direction Faces: West

School Information

  • Elementary School: Dillard Street Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Natural Gas Available, Water Connected

Structural Information

  • Architectural Info: Craftsman, Historical
  • Architectural Style: Craftsman, Historical
  • Exterior Const.: Wood Siding
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,950
  • Sq. Ft. Source: Owner
  • Year Built: 1925

Lot Features

  • Lot Size (Acres): 0.24
  • Lot Size (Sq. Ft.): 10,488
  • Lot Size: 10488
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Financial Considerations

  • Tax Amount: $2,054
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: COOPER & SEWELL ADDITION F/39 LOT 2 BLKD
  • Flood Zone Info: x
  • APN: 142227172804020
  • Property ID: 142227172804020
  • Block/Lot/Section: 4

Listed by Homevest Realty

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Listing agents

— 206 N Highland Ave —

  • Homevest Realty

  • Homevest Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 206 N Highland Ave

School District:Orange County School District
NameGradesDistance
Dillard Street Elementary School
311 North Dillard Street, Winter Garden, FL 34787
PK-50.5 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-80.9 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 206 N Highland Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/29/2026
Listed
$1,100,000
124.49%
MLS
7/29/2025
Sold
$490,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 206 N Highland Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,054
—
$404,230
-7%
2025
$2,054
5%
$433,840
168%
2024
$1,947
4%
$161,904
3%
2023
$1,866
6%
$157,188
6%
2021
$1,765
-2%
$148,165
-3%
2022
$1,800
2%
$152,610
4%
2021
$1,765
2%
$146,119
2%
2019
$1,724
119%
$142,834
67%
2018
$786
5%
$85,760
2%
2017
$750
1%
$83,996
2%
2016
$740
-2%
$82,268
1%
2015
$754
—
$81,696
1%
2014
$757
4%
$81,048
2%
2013
$730
—
$79,850
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Homevest Realty

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206 N Highland Avenue, Winter Garden, FL 34787 (MLS# O6444632) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 206 N Highland Avenue is currently listed for $1,100,000 and was received on September 29, 2026. Want to learn more about 206 N Highland Avenue? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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