Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 2 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 3 of 45
Virtually Staged - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 5 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 6 of 45
Virtually Staged - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 8 of 45
Virtually Staged - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 10 of 45
Virtually Staged - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 12 of 45
Virtually Staged - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 14 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 15 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 16 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 17 of 45
Virtually Staged- Flex space/ office - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 19 of 45
Butler Pantry - 206 N HIGHLAND AVE, WINTER GARDEN
Virtually Staged- Primary Suite - 206 N HIGHLAND AVE, WINTER GARDEN
Virtually Staged- Primary Closet - 206 N HIGHLAND AVE, WINTER GARDEN
Primary Bathroom - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 24 of 45
Virtually Staged - 206 N HIGHLAND AVE, WINTER GARDEN
Jack and Jill Bathroom - 206 N HIGHLAND AVE, WINTER GARDEN
Virtually Staged - 206 N HIGHLAND AVE, WINTER GARDEN
Guest Bathroom - 206 N HIGHLAND AVE, WINTER GARDEN
Virtually Staged- Laundry Room - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 30 of 45
Virtually Staged- Mud Room - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 32 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 33 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 34 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 35 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 36 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 37 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 38 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 39 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 40 of 45
Virtually Staged- Laundry Room - 206 N HIGHLAND AVE, WINTER GARDEN
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 42 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 43 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 44 of 45
Single Family Residence at 206 N HIGHLAND AVE, WINTER GARDEN, photo 45 of 45
45 photos

$1,100,000

206 N HIGHLAND AVE
WINTER GARDEN, FL 34787
Listed by Erica Diaz · HOMEVEST REALTY
Bedrooms
3
Bathrooms
2.5
Living area
1,950 sqft
Year built
1925

About this home

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.

Highlights

Fireplace

Property details

MLS #
MFRO6444632
Property type
Single Family Residence
Subdivision
COOPER & SEWELL ADD
Status
Active
Days on market
N/A
On market date
September 29, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
1
Parking spaces
N/A
Lot size
0.24 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
DILLARD STREET ELEMENTARY
0.44 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
528
Student:teacher ratio
16.0:1
District
ORANGE
Middle
LAKEVIEW MIDDLE
0.86 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
828
Student:teacher ratio
18.8:1
District
ORANGE
High
ORANGE TECHNICAL COLLEGE WESTSIDE CAMPUS
1.23 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
0
Student:teacher ratio
0.0:1
District
ORANGE

Walkability

Blended score for WINTER GARDEN's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

80
Highly walkable
out of 100
EPA National Walkability Index
13.3 / 20 -- Above average walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores17
Parks10
Schools20
Transit stops9
Pharmacies4

Market position

How this listing compares to current activity in WINTER GARDEN, from live MLS data.

On the market 0 days -- 75 fewer days than WINTER GARDEN's current average of 75 days.
For reference, the median list price across 1,018 active listings in WINTER GARDEN right now is $489,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$6,774/mo
$220,000 down
$880,000 loan
Principal & interest$5,708
Property tax (est.)$917
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 12 hr ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.