1060 Gregory Drive, Maitland, FL 32751
For Sale $515,000
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Contact the Listing Agent directly:
Listing Agent: Jill Healey
Agent Phone:
407-797-1420
Agent Email:
jillhealey@kw.com
Scheduled Open Houses
2026-11-15 11:00 am - 1:00 pm
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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.
Primary Bedroom Main Floor
Window Treatments
Taxes: $2,349.01
Tax Year: 2025
Private Yard
Rain Gutters
Dishwasher
Disposal
Dryer
Microwave
Range
Refrigerator
Washer
Elementary School: Lake Orienta Elementary
Middle School: Milwee Middle
Junior High: Milwee Middle
High School: Lyman High
Building Description: Florida
MLS Area: 32751 - Maitland / Eatonville
Total Square Footage: 2,347
Price per Square Feet: $297.00
Total Floors: 1
Water: Public
Construction: Block, Stucco
Date Listed: 2026-10-01 00:00:00
Furnished: Unfurnished
Parking: Driveway, Ground Level
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Wood
Roof: Shingle
Heating: Central
Cooling: Central Air
Fireplace: Y
Laundry: In Garage
Sewer: Septic Tank
Lot Desc.: City Limits, In County, Landscaped, Level, Near Public Transit, Paved
Parcel ID: 24-21-29-507-0B
Listing Courtesy Of: Keller Williams Winter Park
jillhealey@kw.com
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.
Property Details
Price: $515,000
Sq Ft: 1,734
($297 per
sqft)
Bedrooms: 3
Bathrooms: 2
City: Maitland
County: Seminole
Type: Single Family
Development: Druid Hills Estates 1St Add
Acres: 0.2800
Virtual Tour/Floorplan: View
Year Built: 1962
Listing Number: O6445281
Status Code: A-Active
Taxes: $2,349.01
Tax Year: 2025
Garage:
2
/
Y
Furnishings: Unfurnished
Interior Features:
Primary Bedroom Main Floor
Window Treatments
Financial Information:
Taxes: $2,349.01
Tax Year: 2025
Exterior Features:
Private Yard
Rain Gutters
Equipment:
Dishwasher
Disposal
Dryer
Microwave
Range
Refrigerator
Washer
School Information:
Elementary School: Lake Orienta Elementary
Middle School: Milwee Middle
Junior High: Milwee Middle
High School: Lyman High
Additional Information:
Building Description: Florida
MLS Area: 32751 - Maitland / Eatonville
Total Square Footage: 2,347
Price per Square Feet: $297.00
Total Floors: 1
Water: Public
Construction: Block, Stucco
Date Listed: 2026-10-01 00:00:00
Furnished: Unfurnished
Parking: Driveway, Ground Level
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Wood
Roof: Shingle
Heating: Central
Cooling: Central Air
Fireplace: Y
Laundry: In Garage
Sewer: Septic Tank
Lot Desc.: City Limits, In County, Landscaped, Level, Near Public Transit, Paved
Parcel ID: 24-21-29-507-0B
Map of 1060 Gregory Drive, Maitland, FL 32751
Listing Courtesy Of: Keller Williams Winter Park
jillhealey@kw.com