New Listing
In-Person: 10/03 1:00 PM - 4:00 PMSome 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.
| MLS # | O6445281 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | For-sale |
| Status | Active |
| Year | 1962 |
| Days On Site | 2 |
| Listing Provided By | KELLER WILLIAMS WINTER PARK | Jill Healey |
| Bed(s) | 3 |
|---|---|
| Bath(s) | 2 Total |
| SQ Feet | 1,734 |
| Garage | 2 |
| Story(s) | 1 |
| Zoning | R-1AA |
| Acreage | 0.28 |
| Property | 2349 |
|---|
| State | FL |
|---|---|
| County | Seminole |
| City | MAITLAND |
| Zip Code | 32751 |
| Area | 32751 Maitland | Eatonville |
| Community Name | DRUID HILLS ESTATES 1ST ADD |
| School District | Lyman High |
| Elementary School | Lake Orienta Elementary |
| High School | Lyman High |
| Listing VS Median (in DRUID HILLS ESTATES 1ST ADD) | |
Price: $529,000 low | high Med: $539,000 sqft: 1,734 low | high Med: 1,709 $ / sqft: $305 low | high Med: $316 On site: 2 low | high Med: 42 | |
| Open House |
|---|
| In-Person 10/03 1:00 PM - 4:00 PM |
| In-Person 10/04 1:00 PM - 4:00 PM |
| State | FL |
|---|---|
| County | Seminole |
| City | MAITLAND |
| Zip Code | 32751 |
| Area | 32751 Maitland | Eatonville |
| Community Name | DRUID HILLS ESTATES 1ST ADD |
| School District | Lyman High |
| Elementary School | Lake Orienta Elementary |
| High School | Lyman High |
| Listing VS Median (in DRUID HILLS ESTATES 1ST ADD) | |
Price: $529,000 low | high Med: $539,000 sqft: 1,734 low | high Med: 1,709 $ / sqft: $305 low | high Med: $316 On site: 2 low | high Med: 42 | |
![]() | $549,0001055 Druid DrMaitland, FL 32751 |