206 N HIGHLAND AVENUE WINTER GARDEN FL 34787 | MLS #O6444632

206 N HIGHLAND AVENUE WINTER GARDEN FL 34787 | MLS #O6444632

206 N HIGHLAND AVENUE
WINTER GARDEN, FL, 34787
$1,100,000
3 Beds
2.5 Baths
1,950 SqFt
0.24 Acres
Add
MLS #O6444632 image #0
Open House Oct 03, 2026
12:00 – 02:00
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.

Property Details

Price:
$1,100,000
MLS #:
O6444632
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
COOPER & SEWELL ADD
Neighborhood:
34787wintergardenoakland
Listed Date:
Sep 29, 2026
Finished Sq Ft:
1,950
Total Sq Ft:
2,326
Lot Size:
10,488 sqft / 0.24 acres (approx)
Year Built:
1925
Primary Bedroom Main Floor34787 – Winter Garden/oakland34787wintergardenoaklandCooper & Sewell AddDillard Street ElemLakeview MiddleWest Orange HighPlease Verify With The City Of Winter Garden8-12 MonthsPets Allowed

Ask a Question

See this Listing

Send
  

Schools

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

Interior

Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Hardwood
Heating
Central
Interior Features
Built-in Features, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Levels
One

Exterior

Architectural Style
Craftsman, Historical
Construction Materials
Wood Siding
Covered Spaces
1
Direction Faces
West
Exterior Features
Lighting
Garage Spaces
1
Lot Features
Historic District, City Lot
Patio And Porch Features
Covered, Front Porch, Porch, Rear Porch
Roof
Shingle

Financial

Tax Year
2025
Taxes
$2,054

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Sep 30, 2026
794
Single Family Listed
120
Avg DOM
278
Avg $ / SqFt
$752,803
Avg List Price

Property Summary

    Located in the COOPER & SEWELL ADD subdivision, 206 N HIGHLAND AVENUE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $1,100,000 and features 3 beds, 3 baths, and has approximately 1,950 square feet of living space, and was originally constructed in 1925. The current price per square foot is $564. The average price per square foot for Single Family listings in WINTER GARDEN is $278. The average listing price for Single Family in WINTER GARDEN is $752,803. To schedule a showing of MLS#o6444632 at 206 N HIGHLAND AVENUE in WINTER GARDEN, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.

Similar Listings Nearby

broker reciprocity
MLS# O6434371broker reciprocity
1112 HULL ISLAND DRIVE
OAKLAND, FL

$1,400,000

3.6 miles away

broker reciprocity
MLS# O6436608broker reciprocity
1720 LAKE ROBERTS LANDING DRIVE
WINTER GARDEN, FL

$1,399,999

3.2 miles away

broker reciprocity
MLS# G5115613broker reciprocity
1304 APOPKA ROAD
OCOEE, FL

$1,399,000

2.7 miles away

broker reciprocity
MLS# O6414639broker reciprocity
16614 HARBOR SAIL WAY
WINTER GARDEN, FL

$1,399,000

4.3 miles away

broker reciprocity
MLS# O6399958broker reciprocity
12718 ISLES PLACE
WINDERMERE, FL

$1,375,000

4.7 miles away

broker reciprocity
MLS# O6433810broker reciprocity
2317 FARMWOOD CIRCLE
GOTHA, FL

$1,374,999

4.7 miles away

broker reciprocity
MLS# O6410847broker reciprocity
1700 LAKE ROBERTS COURT
WINDERMERE, FL

$1,350,000

3.7 miles away

broker reciprocity
MLS# S5156404broker reciprocity
16730 RUSTY ANCHOR ROAD
WINTER GARDEN, FL

$1,350,000

4.4 miles away

broker reciprocity
MLS# O6442710broker reciprocity
81 MILLHOLLAND STREET
OAKLAND, FL

$1,275,000

2.3 miles away

broker reciprocity
MLS# O6406297broker reciprocity
1554 LAKE RHEA DRIVE
WINDERMERE, FL

$1,275,000

4.1 miles away

206 N HIGHLAND AVENUE
WINTER GARDEN, FL

Schedule An Appointment!

Our team has decades of experience working with buyers and sellers, providing a stress-free experience with proven results.