1065 GREGORY DR Maitland, FL $ 519,000
1065 GREGORY DR
$ 519,000
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1065 GREGORY DR

Maitland, FL, 32751
$ 519,000
Bedrooms3 Baths2.0 Sq 1,929

Monthly Estimate*

$ 3,277

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View a Virtual Tour

Single Family Home for sale in Maitland, FL

for $519,000 with 3 bedrooms and 2 full baths. This 1,929 square foot home was built in 1958 on a lot size of 0.28.

VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home features 3 bed/2 bath in the main house with a 4th room addition on the other side of the garage. The 4th room has it's own separate entrance and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, or income-producing suite — with no HOA to answer to. The cozy fireplace, hardwood floors, and split bedroom floor plan makes it feel like home. The oversized rectangular pool and deck were recently resurfaced and a screen enclosure was added to make maintenance a breeze. There’s still plenty of backyard space to enjoy on the huge 0.28 acre lot equipped with a white vinyl fence and storage shed. Minutes from excellent Maitland private schools and the Winter Park private school corridor, you’ll love the area! It’s close to Trader Joe’s, Winter Park Shopping & Dining, Audubon Center for Birds of Prey, Maitland Art Center, Lake Lily Park, and Enzian Theater. The RDV Sportsplex Athletic Club — with 400+ monthly classes — is an incredible convenience as well! Highway I-4 is close by and the SunRail Maitland Station is only 1 mile away, making downtown Orlando just 24 min commute on the Sunrail. Downtown Maitland is walkable with acclaimed restaurants anchored by a weekly Farmers' Market and the annual Jazz & Blues Festival. Roof is 2020, and water heater is brand new 2026. To see more of the house, WATCH THE VIDEO/VIRTUAL TOUR!

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Single Family Pending

Price

$ 519,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 5,684

Style

Florida Ranch

Lot Size

0.28

Year Built

1958

Town/City

Maitland

County/Region

Seminole

MLS | Web ID

O6411336

Features
General
Sewer Septic Tank
Heating Central
Cooling Central Air
Utilities Public
Possession Close Of Escrow
Roof Shingle
Appliances Dishwasher Dryer Microwave Range Refrigerator Washer
Zoning R-1AA
Garage Spaces 2
Patio/Porch Features Enclosed Front Porch Patio Porch Rear Porch Screened
Architectural Style Florida Ranch
Pool Features In Ground Screen Enclosure
Security Features Security System Owned
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 1958
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Seminole
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name DRUID HILLS ESTATES 1ST ADD
Facing Direction East
Garage Y/N true
Other Structures Shed(s) Storage
Total Rooms 11
Full Baths 2
Status Pending
Directions From the intersection of Maitland Ave and Maitland Blvd head north on Maitland Ave. Turn left onto Oranole Rd then turn left onto Gregory Dr. The property will be on your left.
High School Lyman High
City MAITLAND
Senior Community Y/N false
MLS Area 32751 - Maitland / Eatonville
Lot Size Units Square Feet
Lot Size Square Feet 12371
Carport Y/N false
Listing Terms Cash Conventional FHA
Elementary School Lake Orienta Elementary
Land Lease Y/N false
Tax Annual Amount 5684
Middle/Junior High School Milwee Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://player.vimeo.com/video/1196194213?h=66d5dd2252&badge=0&autopause=0&player_id=0&app_id=58479
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Pending
Occupancy Type Owner
Tax Lot 12
Legal Description LOT 12 BLK A DRUID HILLS ESTATES 1ST ADD PB 11 PG 42
Minimum Lease No Minimum
Water Access Y/N false
Additional Rooms Bonus Room
Water View Y/N false
Flood Zone Code X
In Law Suite YN false
DockY/N false
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Interior
Interior Amenities Ceiling Fan(s) Kitchen/Family Room Combo Primary Bedroom Main Floor Split Bedroom Thermostat
Flooring Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Living Room Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds
Fireplace Y/N true
Half Baths 0
Laundry Features In Garage Laundry Room
Total Bedrooms 3
Total Baths 2
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Exterior
Exterior Amenities French Doors Irrigation System Storage
Vegetation Mature Landscaping
Fencing Vinyl
Parking Features Driveway
Water Source Public
Lot Size Area 12371
Foundation Details Crawlspace
Building Area Total 2609
Lot Size Acres 0.28
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Paved
Road Responsibility Public Maintained Road
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* Excluded Features
List By
cece.wong@exprealty.com

Email

Affordability Calculator

$3,751
Per Month
87%
13%
0%
Monthly Principal & Interest
$3,277
Monthly Property Taxes
$474
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Lyman High High School High School
Pricing History
DatePricePrice ChangeDescription
5/28/2026$519,000 Listed Price

Map


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1065 GREGORY DR, Maitland, FL, 32751 is a Single Family Home for sale at $519,000 with 1,929 sqft and a lot size of 0.28. 1065 GREGORY DR has 3 bedrooms, 2.0 baths, and was built in 1958. The property's zip code is 32751 which is in Maitland, FL