128 N Highland Avenue, WINTER GARDEN, FL

$965,000

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4

Beds

3

Baths

2,325

Square feet

0.34

Acres

About 128 N Highland Avenue

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!

Features of 128 N Highland Avenue

MLS® # O6442723
Price $965,000
Bedrooms 4
Bathrooms 3.00
Full Baths 2
Half Baths 1
Square Footage 2,325
Acres 0.34
Year Built 1920
Type Residential
Sub-Type Single Family Residence
Style Bungalow, Craftsman
Status Pending

Community Information

Address 128 N Highland Avenue
Area Winter Garden/Oakland
Subdivision COOPER & SEWELL ADD
City WINTER GARDEN
County Orange
State FL
Zip Code 34787-2738

Amenities

Parking Driveway, On Street, Oversized, Workshop in Garage
# of Garages 1
View Garden, Trees/Woods
Is Waterfront No
Has Pool No

Interior

Interior Features Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, PrimaryBedroom Upstairs, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-In Closet(s)
Appliances Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Heating Central, Electric
Cooling Central Air
Fireplace Yes
Fireplaces Decorative, Electric

Exterior

Exterior Features Lighting, Outdoor Shower, Rain Gutters, Sidewalk, Storage
Lot Description Historic District, City Lot, Level, Oversized Lot, Sidewalk
Roof Shingle
Foundation Crawlspace, Stilt/On Piling

School Information

Elementary Dillard Street Elem
Middle Lakeview Middle
High West Orange High

Additional Information

Date Listed September 17th, 2026
Zoning R-2
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeDENIZ REALTY PARTNERS LLC

Listing Map

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