1060 GREGORY DR, Maitland, FL 32751
1060 GREGORY DR, Maitland, FL 32751,Video Tour
1060 GREGORY DR, Maitland, FL 32751
32
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$529,000
Est. payment /mo
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3 Beds
2 Baths
1,734 SqFt
Open Fri 5PM-7PM

1060 GREGORY DR Maitland, FL 32751

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Jill Anayas

Jill Anayas

+1(904) 962-1098

Open House

Fri Oct 02, 5:00pm - 7:00pm

Sat Oct 03, 1:00pm - 4:00pm

Sun Oct 04, 1:00pm - 4:00pm

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 1,734 sqft

Price per Sqft $305

Subdivision Druid Hills Estates 1St Add

MLS Listing ID O6445281

Bedrooms 3

Full Baths 2

HOA Y/N No

Year Built 1962

Annual Tax Amount $2,349

Lot Size 0.280 Acres

Acres 0.28

Lot Dimensions 117x105

Property Sub-Type Single Family Residence

Source Stellar MLS

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 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.

Location

State FL

County Seminole

Community Druid Hills Estates 1St Add

Area 32751 - Maitland / Eatonville

Zoning R-1AA

Interior

Interior Features Primary Bedroom Main Floor, Window Treatments

Heating Central

Cooling Central Air

Flooring Wood

Fireplaces Type Family Room, Wood Burning

Furnishings Unfurnished

Fireplace true

Appliance Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer

Laundry In Garage

Exterior

Exterior Feature Private Yard, Rain Gutters

Parking Features Driveway, Ground Level

Garage Spaces 2.0

Utilities Available Cable Connected, Electricity Connected, Public, Water Connected

View Y/N No

Water Access No

Roof Type Shingle

Porch Covered, Front Porch

Attached Garage true

Exposure West

Garage true

Private Pool No

Building

Lot Description City Limits, In County, Landscaped, Level, Near Public Transit, Paved

Story 1

Entry Level One

Foundation Crawlspace, Other

Lot Size Range 1/4 to less than 1/2

Sewer Septic Tank

Water Public

Architectural Style Florida

Structure Type Block,Stucco

New Construction false

Schools

Elementary Schools Lake Orienta Elementary

Middle Schools Milwee Middle

High Schools Lyman High

Others

Senior Community No

Ownership Fee Simple

Acceptable Financing Cash, Conventional, FHA, VA Loan

Listing Terms Cash, Conventional, FHA, VA Loan

Special Listing Condition None

Virtual Tour https://www.zillow.com/view-imx/8c4c31f4-6969-4546-8aed-3c553a78740b?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard

Stellar MLS
© 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved.
Listed by Jill Healey KELLER WILLIAMS WINTER PARK

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Jill Anayas
Jill Anayas

REALTOR ®

+1(904) 962-1098 | jillanayas@pm.me

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1060 GREGORY DR