$529,000
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 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.
Highlights
Property details
- MLS #
- MFRO6445281
- Property type
- Single Family Residence
- Subdivision
- DRUID HILLS ESTATES 1ST ADD
- Status
- Active
- Days on market
- N/A
- On market date
- October 1, 2026
- Stories
- N/A
- Total bathrooms
- 2
- Garage spaces
- 2
- Parking spaces
- N/A
- Lot size
- 0.28 acres
Location
Get directions →Nearby schools
Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).
- Enrollment
- 631
- Student:teacher ratio
- 15.0:1
- District
- SEMINOLE
- Enrollment
- 774
- Student:teacher ratio
- 19.8:1
- District
- ORANGE
- Enrollment
- 39
- Student:teacher ratio
- 9.8:1
- District
- SEMINOLE
Walkability
Blended score for MAITLAND's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).
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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 1 days ago.
Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.