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 a 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.
Listed By
Agency Name: KELLER WILLIAMS WINTER PARK
Agency Contact: 407-545-6430
Shown By
Agent Name: Lydia Walls
Agent Phone: (937) 935-5597
Agency Title: Key Realty
Estimated Payment
$ 3,309.12 per month $2,959.08 Principal & Interest $195.75 Property Tax $154.29 Homeowner's InsuranceIf the email address was found in our system, your password has been sent. Please check your inbox.
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1060 Gregory Drive | MLS# O6445281
This single family home located at 1060 Gregory Drive , Maitland, FL 32751 is currently listed for sale with an asking price of $529,000. This property was built in 1962 and has 3 bedrooms and 2 full baths with 1734 sq. ft. Gregory Drive is located in the DRUID HILLS ESTATES 1ST subdivision. Search DRUID HILLS ESTATES 1ST real estate on www.lydiawalls.com today.