31 photos in the listing
1060 Gregory Drive
Maitland, FL 32751 · Seminole County
$529,000
3
Beds
2
Baths
1,734
Sq ft
1962
Year built
Location
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 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.
Facts & features
Interior
- Bedrooms
- 3
- Bathrooms
- 2
- Living area
- 1,734 sq ft
- Stories
- 1
- Flooring
- Wood
- Appliances
- Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
- Features
- Primary Bedroom Main Floor, Window Treatments
- Fireplace
- Yes
- Cooling
- Central Air
- Heating
- Central
Exterior & lot
- Lot size
- 0.28 acres
- Construction
- Block, Stucco
- Roof
- Shingle
- Features
- Private Yard, Rain Gutters
Parking
- Garage spaces
- 2
Financial
- Price / sqft
- $305/sqft
- Annual tax
- $2,349.01
- Tax year
- 2025
Utilities
- Utilities
- Cable Connected, Electricity Connected, Public, Water Connected
- Water
- Public
- Sewer
- Septic Tank
Property
- Property type
- Single Family
- Year built
- 1962
- Subdivision
- Druid Hills Estates 1st Add
- Days on market
- 19 days
Estimate your monthly cost
Twenty percent down over thirty years at 6.5%. Insurance is not included.
- Principal & interest
- $2,675
- Property tax
- $196
- Estimated monthly
- $2,871
Ask about this property
Answered from this listing’s own figures and the sales around it.
Similar homes nearby
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Oct 1, 2026 | Listed | $529,000 | — |
Neighbourhood
The schools below come from the MLS record for this home. Walking, transit and cycling figures for Maitland, FL are not connected yet, so this page does not show them.
About this area
MAITLAND, FL sits in Seminole County. Asking prices on the 8 nearest homes we hold run from $394,900 to $600,000, with $502,000 in the middle. Those are asking prices, not closed sales. The MLS record names Lake Orienta Elementary (elementary), Milwee Middle (middle), Lyman High (high) as the assigned schools.
Written from this listing’s own record and the homes we hold nearby.
- Elementary school
- Lake Orienta Elementary
- Assigned school from the MLS record
- Middle school
- Milwee Middle
- Assigned school from the MLS record
- High school
- Lyman High
- Assigned school from the MLS record
Frequently asked questions
What would 1060 GREGORY DRIVE, MAITLAND cost per month?
About $2,871 a month: $2,675 principal and interest, $196 property tax. That assumes 20% down at 6.5% over 30 years, and leaves out insurance.
Is 1060 GREGORY DRIVE, MAITLAND priced fairly?
Comparable homes nearby put it between $470,079 and $540,843, with $505,461 in the middle. Those are asking prices, not closed sales: 8 properties of the same type within three miles, each within 20% of this one's size and a bedroom either way, at a median of $292 a square foot.
How does 1060 GREGORY DRIVE, MAITLAND compare to nearby homes?
8 comparable properties within three miles. The nearest: 1055 DRUID DRIVE, MAITLAND, FL at $549,000, 1,684 sq ft, 0.03 miles away; 1202 ORANOLE ROAD, MAITLAND, FL at $394,900, 1,750 sq ft, 0.09 miles away; 370 SULTANA LANE, MAITLAND, FL at $484,000, 1,683 sq ft, 0.15 miles away.
How long has 1060 GREGORY DRIVE, MAITLAND been on the market?
17 days on the market.
Has the price of 1060 GREGORY DRIVE, MAITLAND changed?
The price has not moved since it was listed.
How big is 1060 GREGORY DRIVE, MAITLAND?
3 bed, 2 bath, 1,734 square feet. That is $305 a square foot.
What year was 1060 GREGORY DRIVE, MAITLAND built?
Built in 1962.
What is the HOA fee at 1060 GREGORY DRIVE, MAITLAND?
The feed lists no association fee for this property.
What are the property taxes at 1060 GREGORY DRIVE, MAITLAND?
Property tax works out to about $196 a month, $2,349 a year, on the 2025 assessment.
Is 1060 GREGORY DRIVE, MAITLAND still available?
It is still on the market.
Listing
- Listed by
- Jill Healey
- Brokerage
- KELLER WILLIAMS WINTER PARK
- MLS number
- MFR812547242
Listing information is deemed reliable but is not guaranteed.