Maitland, FL · Single Family Residence
1060 Gregory Dr
Active · MLS MFRO6445281 · Listed by KELLER WILLIAMS WINTER PARK · 407-545-6430.
THE SETTING, AND THE DETAILS
A closer look.
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.
The details that help you decide.
Details supplied with the listing. Information that was not provided is marked below.
Home essentials
- Price per square foot
- $305
- Full bathrooms
- 2
- Half bathrooms
- 0
- Heated living area
- 1734
- Lot size (acres)
- 0.28
- Lot size (sq ft)
- 12386
- Year built
- 1962
- Property type
- Residential
- Property style
- Florida
Interior & rooms
- Interior features
- Primary Bedroom Main Floor, Window Treatments
- Appliances
- Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
- Flooring
- Wood
- Additional rooms
- Not provided
Land, water & community
- Waterfront
- No
- Waterfront type
- Not provided
- Water body / lake name
- Not provided
- Water view
- Not provided
- Dock
- Not provided
- Dock features
- Not provided
- Other views
- Not provided
- Lot features
- City Limits, In County, Landscaped, Level, Near Public Transit, Paved
- Exterior features
- Private Yard, Rain Gutters
- Community amenities
- Not provided
- Zoning
- R-1AA
- Current use
- Not provided
- Horse amenities
- Not provided
- Fencing
- Not provided
- Other structures
- Not provided
Pool, parking & systems
- Private pool
- No
- Pool features
- Not provided
- Garage
- Yes
- Garage spaces
- 2
- Carport
- No
- Carport spaces
- Not provided
- Parking features
- Driveway, Ground Level
- Fireplace
- Yes
- Fireplace features
- Family Room, Wood Burning
- Heating
- Central
- Cooling
- Central Air
- Water supply
- Public
- Sewer
- Septic Tank
- Utilities
- Cable Connected, Electricity Connected, Public, Water Connected
Construction
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Crawlspace, Other
- Stories
- 1
- Levels
- One
Location & schools
- City
- MAITLAND
- Subdivision
- DRUID HILLS ESTATES 1ST ADD
- County
- Seminole
- ZIP code
- 32751
- Elementary school
- Lake Orienta Elementary
- Middle school
- Milwee Middle
- High school
- Lyman High
Association, taxes & listing
- HOA / association
- No
- Association fee
- Not provided
- Fee frequency
- Not provided
- Included services
- Not provided
- Association amenities
- Not provided
- Additional association fee
- Not provided
- Additional fee frequency
- Not provided
- Condo fee
- Not provided
- Condo fee frequency
- Not provided
- Annual property taxes
- $2,349.01
- Tax year
- 2025
- Other annual assessments
- Not provided
- CDD
- No
- Listing status
- Active
- Days on market
- 1
- Listing broker
- KELLER WILLIAMS WINTER PARK
- MLS number
- MFRO6445281
Explore the area
Location supplied with the listing. Confirm boundaries and access for the property.
Listed by KELLER WILLIAMS WINTER PARK · MLS MFRO6445281
Source: mfrmls · Listing updated 2026-10-02 13:42:11 UTC.
Information is deemed reliable but is not guaranteed. Availability and details may change.
A GOOD CONVERSATION IS A GOOD START
Let’s talk about
your next move.
Ask about this home, arrange a showing, or talk through what you’re looking for.
Call Scott: (407) 760-0382Your inquiry goes directly to Scott.