1060 GREGORY DRIVE MAITLAND, FL 32751

$529,000

3 Beds

2 Baths

1734 sqft

Property Details

MLS#

O6445281

Type

Single Family Residence

Status

Active Listing

Square Footage

1,734

Bedrooms

3

Bathrooms

2 full

Year Built

1962

Tax Amount

$2,349

Garage Spaces

2

Property Description

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.

Amenities

Cooling:Central Air

French Doors

Private Yard

Rain Gutters

Primary Bedroom Main Floor

Window Treatments

Payment Calculator

per month

, 

 Principal & Interest

 Property Tax

 Mortage Insurance

 HOA

 Home Owners Insurance

Home Price
Interest Rate
Down Payment
 Customize Calculations
Property Taxes
/ year
Homeowner's Insurance
/ month
HOA Dues
Mortgage Insurance
Loan Type
Location Map

The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations. Copyright 2026 Southwest Florida MLS organizations. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.

All listings featuring the BMLS logo are provided by Beaches MLS Inc. Copyright 2026 Beaches MLS. This information is not verified for authenticity or accuracy and is not guaranteed.

© 2026 Beaches Multiple Listing Service, Inc. All rights reserved.

The data relating to real estate for sale on this web site comes in part from the participating Associations/MLS's Miami Association of Realtors, and the Realtor Association of Greater Ft. Lauderdale.

Information is deemed reliable but not guaranteed. Copyright 2026, Miami Association of Realtors, Realtor Association of Greater Ft. Lauderdale, and the South Broward Board of Realtors. All rights reserved. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited.

Some properties that appear for sale on this limited electronic display may no longer be available. For the most current information, contact one of our agents.