128 HIGHLAND AVENUE
WINTER GARDEN, FL 34787
Location
About this home
Under contract-accepting backup offers. 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!
Facts & features
Interior
- Bedrooms
- 4
- Bathrooms
- 3
- Living area
- 2,325 sqft
- Heating
- Central, Electric
- Cooling
- Central Air
- Flooring
- Carpet, Ceramic Tile, Wood
- Fireplace
- Yes
- Features
- Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Living Room/Dining Room Combo, PrimaryBedroom Upstairs…
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range…
Exterior & lot
- Lot size
- 14,649 sqft (0.34 ac)
- Roof
- Shingle
- Construction
- Frame
- Exterior
- Lighting, Outdoor Shower, Rain Gutters, Sidewalk, Storage
Parking
- Garage
- 1 space
Financial
- Annual tax
- $6,372 (2025)
- Price / sqft
- $415/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Available, Public, Sewer Available, Sprinkler Well…
Property
- Property type
- Single Family
- Year built
- 1920
- Subdivision
- COOPER & SEWELL ADD
- County
- Orange
Assigned schools
- Elementary
- Dillard Street Elem
- Middle
- Lakeview Middle
- High
- West Orange High
Listing
- Status
- Under Contract
- Days on market
- 4 days
- MLS #
- MFR811637652
- Source
- Stellar MLS
Listed by Kurt Gunter · DENIZ REALTY PARTNERS LLC
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Estimate your monthly cost
PITI + HOA- Principal & interest
- $4,880/mo
- Property tax
- $531/mo
- Home insurance
- Left out until you enter a quote
Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own 2025 bill. Insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.
Ask about this property
Answered from this listing’s own figures and the sales around it.
Similar homes nearby
Homes for sale in WINTER GARDEN within the same price band.
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Sep 17, 2026 | Listed | $965,000 | — |
Neighbourhood
The schools below come from the MLS record for this home. Walking, transit and cycling figures for WINTER GARDEN, FL are not connected yet, so this page does not show them.
Frequently asked questions
What would 128 HIGHLAND AVENUE, WINTER GARDEN cost per month?
About $5,411 a month: $4,880 principal and interest, $531 property tax. That assumes 20% down at 6.5% over 30 years, and leaves out insurance.
Is 128 HIGHLAND AVENUE, WINTER GARDEN priced fairly?
Comparable homes nearby put it between $773,005 and $889,371, with $831,188 in the middle. Those are asking prices, not closed sales: 8 properties of the same type within three miles, each within 20% of this one's size and a bedroom either way, at a median of $358 a square foot.
How does 128 HIGHLAND AVENUE, WINTER GARDEN compare to nearby homes?
8 comparable properties within three miles. The nearest: 213 TILDEN STREET, WINTER GARDEN, FL at $765,000, 2,151 sq ft, 0.2 miles away; 18 & 20 PLANT STREET, WINTER GARDEN, FL at $2,999,000, 2,699 sq ft, 0.27 miles away; 368 BOYD STREET, WINTER GARDEN, FL at $829,000, 2,331 sq ft, 0.28 miles away.
How long has 128 HIGHLAND AVENUE, WINTER GARDEN been on the market?
It came on the market today.
Has the price of 128 HIGHLAND AVENUE, WINTER GARDEN changed?
The price has not moved since it was listed.
How big is 128 HIGHLAND AVENUE, WINTER GARDEN?
4 bed, 3 bath, 2,325 square feet. That is $415 a square foot.
What year was 128 HIGHLAND AVENUE, WINTER GARDEN built?
Built in 1920.
What is the HOA fee at 128 HIGHLAND AVENUE, WINTER GARDEN?
The feed lists no association fee for this property.
What are the property taxes at 128 HIGHLAND AVENUE, WINTER GARDEN?
Property tax works out to about $531 a month, $6,372 a year, on the 2025 assessment.
Is 128 HIGHLAND AVENUE, WINTER GARDEN still available?
It is under contract.
