206 N HIGHLAND AVENUE Winter Garden, FL $ 1,100,000
206 N HIGHLAND AVENUE
$ 1,100,000
Recently Listed
Open House 10/10 12pm - 2pm
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206 N HIGHLAND AVENUE

Winter Garden, FL, 34787
$ 1,100,000
Bedrooms3 Baths2.1 Sq 1,950

Monthly Estimate*

$ 7,597

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View a Virtual Tour

Single Family Home for sale in Winter Garden, FL

for $1,100,000 with 3 bedrooms and 2 full baths, 1 half bath. This 1,950 square foot home was built in 1925 on a lot size of 0.24.

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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Open House

10/10/2026 12:00 PM - 2:00 PM
206 N HIGHLAND AVENUE Winter Garden, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 1,100,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 2,054

Style

Craftsman Historical

Lot Size

0.24

Year Built

1925

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6444632

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Electricity Connected Natural Gas Available Water Connected
Roof Shingle
Appliances Dishwasher Disposal Electric Water Heater Microwave Range Range Hood Refrigerator
Zoning R-2
Garage Spaces 1
Patio/Porch Features Covered Front Porch Porch Rear Porch
Architectural Style Craftsman Historical
Construction Materials Wood Siding
Pets Allowed Yes
Year Built 1925
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Attached Garage false
Subdivision Name COOPER & SEWELL ADD
Facing Direction West
Garage Y/N true
Total Rooms 10
Full Baths 2
Status Active
Directions From Plant Street head north on N Highland. Home will be on the left.
High School West Orange High
City WINTER GARDEN
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 10488
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Dillard Street Elem
Land Lease Y/N false
Tax Annual Amount 2054
Middle/Junior High School Lakeview Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6444632
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 020
Legal Description COOPER & SEWELL ADDITION F/39 LOT 2 BLKD
Minimum Lease 8-12 Months
Water Access Y/N false
Additional Rooms Den/Library/Office Inside Utility
Water View Y/N false
Flood Zone Code x
In Law Suite YN false
Flood Zone Code X Y
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Interior
Interior Amenities Built-in Features Kitchen/Family Room Combo Living Room/Dining Room Combo Primary Bedroom Main Floor Stone Counters Walk-In Closet(s)
Flooring Ceramic Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Family Room Gas Masonry Non Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities Lighting
Vegetation Mature Landscaping
Lot Features Historic District City Lot
Water Source Public
Lot Size Area 10488
Foundation Details Crawlspace
Building Area Total 2326
Lot Size Acres 0.24
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
Covered Spaces 1
Road Frontage Type Street Paved
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* Excluded Features
List By
Homevest Realty

Broker

erica@ericadiazteam.com

Email

Affordability Calculator

$7,769
Per Month
98%
2%
0%
Monthly Principal & Interest
$7,597
Monthly Property Taxes
$171
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
9/29/2026$1,100,000 Listed Price

Map


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206 N HIGHLAND AVENUE, Winter Garden, FL, 34787 is a Single Family Home for sale at $1,100,000 with 1,950 sqft and a lot size of 0.24. 206 N HIGHLAND AVENUE has 3 bedrooms, 2.1 baths, and was built in 1925. The property's zip code is 34787 which is in Winter Garden, FL