1060 Gregory Drive, Maitland, FL 32751
Local realty services provided by:Bingham Realty ERA Powered
Upcoming open houses
- Sun, Oct 0401:00 pm - 04:00 pm
Listed by: jill healey
Office: keller williams winter park
MLS#:O6445281
Source:MFRMLS
Price summary
- Price:$529,000
- Price per sq. ft.:$225.39
About this home
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 dual closets. 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, HVAC and REROOF 2020, WATER HEATER 2022, a NEW FENCE installed in 2023 and REPIPED 2009. 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....
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Home facts
- Year built:1962
- Subdivision & Development:DRUID HILLS ESTATES 1ST ADD
- Listing ID #:O6445281
- Added:2 day(s) ago
- Updated:October 03, 2026 at 08:43 PM
Rooms and interior
- Bedrooms:3
- Total bathrooms:2
- Full bathrooms:2
- Flooring:Wood
- Kitchen Description:Dishwasher, Disposal, Microwave, Range, Refrigerator
- Bedroom Description:Primary Bedroom Main Floor
- Basement Description:Crawlspace
- Living area:1,734 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central
- Central air:Yes
Structure and exterior
- Roof:Shingle
- Year built:1962
- Building area:1,734 sq. ft.
- Lot area:0.28 Acres
- Lot Features:Landscaped, Level, Near Public Transit, Paved
- Architectural Style:Florida
- Construction Materials:Block, Stucco
- Exterior Features:Covered Porch/Patio, Front Porch, Rain Gutters
- Levels:1 Story
Schools
- High school:Lyman High
- Middle school:Milwee Middle
- Elementary school:Lake Orienta Elementary
Utilities
- Water:Public, Water Connected
- Sewer:Public, Septic Tank
Finances and disclosures
- Price:$529,000
- Price per sq. ft.:$225.39
- Tax amount:$2,349 (2025)
Features and amenities
- Appliances:Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
- Laundry features:Dryer, In Garage, Washer
- Amenities:Cable Connected, Primary Bedroom Main Floor, Window Treatments
- Pool features:Public Pool
Parking
- Parking description:Attached Garage, Driveway, Ground Level
- Garage:Yes
- Garage spaces:2
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