Front of property - 128 N HIGHLAND AVE, WINTER GARDEN
Artificial Turf yard - 128 N HIGHLAND AVE, WINTER GARDEN
New gravel driveway - 128 N HIGHLAND AVE, WINTER GARDEN
Front porch - 128 N HIGHLAND AVE, WINTER GARDEN
Front porch - 128 N HIGHLAND AVE, WINTER GARDEN
Living area - 128 N HIGHLAND AVE, WINTER GARDEN
Living area - 128 N HIGHLAND AVE, WINTER GARDEN
Dining area - 128 N HIGHLAND AVE, WINTER GARDEN
Dining area - 128 N HIGHLAND AVE, WINTER GARDEN
Dining area - 128 N HIGHLAND AVE, WINTER GARDEN
Kitchen - 128 N HIGHLAND AVE, WINTER GARDEN
Kitchen - 128 N HIGHLAND AVE, WINTER GARDEN
Kitchen - 128 N HIGHLAND AVE, WINTER GARDEN
Laundry room - 128 N HIGHLAND AVE, WINTER GARDEN
Loft - 128 N HIGHLAND AVE, WINTER GARDEN
Primary bedroom - 128 N HIGHLAND AVE, WINTER GARDEN
Primary bedroom - 128 N HIGHLAND AVE, WINTER GARDEN
Primary bathroom - 128 N HIGHLAND AVE, WINTER GARDEN
Primary bathroom - 128 N HIGHLAND AVE, WINTER GARDEN
Primary bathroom - 128 N HIGHLAND AVE, WINTER GARDEN
Primary bathroom - 128 N HIGHLAND AVE, WINTER GARDEN
Bedroom #2 - 128 N HIGHLAND AVE, WINTER GARDEN
Bedroom #2 - 128 N HIGHLAND AVE, WINTER GARDEN
Bedroom #3 - 128 N HIGHLAND AVE, WINTER GARDEN
Bedroom #3 - 128 N HIGHLAND AVE, WINTER GARDEN
Bathroom #2 - 128 N HIGHLAND AVE, WINTER GARDEN
Bedroom #4/ Flex Space or Home Office - 128 N HIGHLAND AVE, WINTER GARDEN
Bedroom #4/ Flex Space or Home Office - 128 N HIGHLAND AVE, WINTER GARDEN
Half bathroom - 128 N HIGHLAND AVE, WINTER GARDEN
Half bathroom - 128 N HIGHLAND AVE, WINTER GARDEN
Workshop space - 128 N HIGHLAND AVE, WINTER GARDEN
Patio - 128 N HIGHLAND AVE, WINTER GARDEN
Backyard - 128 N HIGHLAND AVE, WINTER GARDEN
Backyard - 128 N HIGHLAND AVE, WINTER GARDEN
Backyard - 128 N HIGHLAND AVE, WINTER GARDEN
35 photos

$965,000

128 N HIGHLAND AVE
WINTER GARDEN, FL 34787
Listed by DENIZ REALTY PARTNERS LLC
Bedrooms
4
Bathrooms
2.5
Living area
2,325 sqft
Year built
1920

About this home

Welcome to a piece of history, right in the Winter Garden's golf cart district! This stunning Craftsman bungalow is nestled in the Historic District, where timeless character meets extensive modern updates. Set on a 0.34-acre lot beneath grandfather oaks, this home creates an atmosphere that feels peaceful while placing you just steps from the energy of downtown. From the moment you arrive, you're greeted by a gravel driveway(2021) that leads to the front of the property, while outdoor lighting (2021) creates a welcoming glow as the sun goes down. Step through the beautiful leaded glass front door into a home filled with warmth and character. Rich heart pine floors, 9-foot ceilings, and crown molding create a timeless backdrop that is sure to make everyone feel at home.The front living and dining area provides a comfortable place to entertain or settle in with loved ones. Nearby, a flexible room can function as a bedroom or home office, and includes its own half bath, giving you the freedom to shape the space around your family's needs. At the center of the home, the farmhouse-inspired kitchen includes real wood cabinetry, granite countertops, and a convenient side entry to make everything from everyday cooking to hosting dinners feel effortless. The side entrance also makes bringing in groceries especially convenient. Down the hall, two bedrooms create comfortable retreats and share a guest bathroom with subway tile detailing. The guest bathroom tub drain line was replaced in 2025, while extensive flooring and subfloor improvements completed throughout the home provide a refreshed foundation from room to room. Upstairs, you’ll find the new flooring that was installed in 2025, along with recessed lighting (2018), and a bright and inviting loft space with flexibility for a reading area or home office. The primary bedroom was remodeled in 2025 and includes a custom built-in closet for exceptional organization. The upstairs bathroom was also remodeled in 2025, creating a beautifully updated space to begin and end your day. The home has received extensive upgrades, providing the new owners with peace of mind that this home was truly cared for. Upgrades include a downstairs HVAC system (2023), a replacement of the downstairs ductwork (2025), foundation support installed beneath the rear half of the home with concrete footers (2024), and a new water heater (2025). The home's exterior has been refreshed as well, including Artificial turf (2021) for easy upkeep, new exterior paint (Dec, 2024) and a new roof (2023). Heading outside, you're bound to love the private fenced in backyard space. Whether you're imagining weekend gatherings, letting little ones play, or simply enjoying a quiet afternoon outdoors, there's room to create the backyard you've always wanted. The detached 25' x 25' garage and workshop adds another layer of flexibility, complete with 100-amp electrical service. For a hobbyist, craftsman, or anyone who needs additional storage and workspace, this building can become whatever your lifestyle requires.This is a home with character you simply can't recreate, paired with the extensive updates and improvements. And perhaps best of all, you're living in the heart of Historic Downtown Winter Garden, where morning walks, farmers markets, local dining, shopping, live entertainment, and community events can become part of your daily routine. Don't wait on this amazing home, schedule your private showing TODAY!

Highlights

Fireplace

Property details

MLS #
MFRO6442723
Property type
Single Family Residence
Subdivision
COOPER & SEWELL ADD
Status
Active
Days on market
1
On market date
September 17, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
1
Parking spaces
N/A
Lot size
0.34 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
DILLARD STREET ELEMENTARY
0.48 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
0.84 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
1.2 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: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 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
Nearby-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 1 days -- 77 fewer days than WINTER GARDEN's current average of 78 days.
For reference, the median list price across 985 active listings in WINTER GARDEN right now is $485,000.

Mortgage calculator

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Est. monthly payment
$5,961/mo
$193,000 down
$772,000 loan
Principal & interest$5,007
Property tax (est.)$804
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 1 days 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.