1060 Gregory Drive MAITLAND, FL 32751-3209
3
Beds
2
Baths
1,734
Square feet
0.28
Acres
$529,000
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 |
|---|---|
| Zoning | R-1AA |
| Flood Zone Code | X |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | KELLER WILLIAMS WINTER PARK |
|---|