1060 Gregory Drive MAITLAND, FL 32751-3209

3

Beds

2

Baths

1,734

Square feet

0.28

Acres

$529,000

Open House

  • Friday, October 02, 2026 (Start Time: 5:00 PM - End time: 7:00 PM)
  • Saturday, October 03, 2026 (Start Time: 1:00 PM - End time: 4:00 PM)
  • Sunday, October 04, 2026 (Start Time: 1:00 PM - End time: 4:00 PM)

About 1060 Gregory Drive

Some homes have a character that simply cannot be recreated—and 1060 Gregory Drive is one of them. Built in 1962 and tucked beneath mature oaks draped in Spanish moss, this three-bedroom, two-bath Maitland home celebrates its original charm while offering the updates today’s buyers appreciate. Warm hardwood floors flow through the home, while a dramatic brick feature wall separates the living and family rooms, with a fireplace facing each space. It is a memorable architectural detail that makes both rooms feel welcoming and distinct. The updated kitchen pairs shaker-style cabinetry with granite countertops and stainless steel appliances, while plantation shutters and ceiling fans add comfort and classic style throughout. The primary bedroom features a walk-in closet and updated ensuite bath with a new quartz topped vanity. The guest bathroom also benefits from a new vanity. Step outside to an expansive backyard deck with plenty of room for dining, entertaining and lingering beneath the trees on beautiful Florida evenings. Major improvements include an ELECTRICAL UPDATE 2026, ALL NEW DUCTWORK 2026, REPIPED 2025, HVAC and REROOF 2020, WATER HEATER 2022, along with a NEW FENCE installed in 2023. Set in an established Maitland neighborhood with quick access to Winter Park, Maitland and Interstate 4, this is a home with a story, a setting and a style all its own. Come experience the character, comfort and tree-lined charm that make 1060 Gregory Drive feel like home from the moment you arrive.

Residential home for sale in MAITLAND, FL at 1060 Gregory Drive. This 3 bedroom Residential home is priced at $305/sqft

Features of 1060 Gregory Drive

MLS® # O6445281
Price $529,000
Bedrooms 3
Bathrooms 2.00
Full Baths 2
Square Footage 1,734
Acres 0.28
Year Built 1962
Type Residential
Sub-Type Single Family Residence
Style Florida
Status Active

Community Information: Maitland

Address 1060 Gregory Drive
Area Maitland / Eatonville
Subdivision DRUID HILLS ESTATES 1ST ADD
City MAITLAND
County Seminole
State FL
Zip Code 32751-3209

Amenities of 1060 Gregory Drive

Parking Driveway, Ground Level
# of Garages 2
Is Waterfront No
Has Pool No
Senior Community No

Interior of 1060 Gregory Drive

Interior Features Primary Bedroom Main Floor, Window Treatments
Appliances Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
Heating Central
Cooling Central Air
Fireplace Yes
Fireplaces Family Room, Wood Burning
# of Stories 1
Furnished Unfurnished

Exterior of 1060 Gregory Drive

Exterior Features French Doors, Private Yard, Rain Gutters
Lot Description City Lot, In County, Landscaped, Level, Near Public Transit
Roof Shingle
Foundation Crawlspace, Other

School Information

Elementary Lake Orienta Elementary
Middle Milwee Middle
High Lyman High

Additional Information On 1060 Gregory Drive

Date Listed October 1st, 2026
Days on Market 1
Zoning R-1AA
Flood Zone Code X
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeKELLER WILLIAMS WINTER PARK

Map To 1060 Gregory Drive, MAITLAND

Request a Showing

Provide a valid email address.
When would you like to view this property?