$519,000
Active

1065 GREGORY DR

MAITLAND, FL 32751 — DRUID HILLS ESTATES 1ST ADD
4 Beds
2 Baths
1,929 sqft
0.28 acres
Built 1958
2-Car Garage

About This Property

VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home on over a ¼ acre offers something rare: a spacious 4th room addition with its own separate entrance in driveway and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, income-producing suite, or dedicated learning space — with no HOA to answer to. The main house features 3 bed/2bath and 2 separate living areas with a split bedroom floor plan. The cozy fireplace and hardwood floors 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!

Property Details

Basics

Property Type
Residential
Property Subtype
Single Family Residence
MLS Number
O6411336
Year Built
1958
Levels
One
Architectural Style
Florida, Ranch
Additional Rooms
Bonus Room
Direction Faces
East
Occupant Type
Owner

Size & Structure

Living Area
1,929 sqft
Total Area
2,609 sqft
Lot Size
0.28 acres
Lot Sq Ft
12,371 sqft
Bedrooms
4
Full Baths
2
Garage Spaces
2

Interior

Flooring
Tile, Wood
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Interior Features
Ceiling Fans(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat
Laundry
In Garage, Laundry Room
Windows
Blinds
Fireplace
Yes — Living Room, Wood Burning
Furnished
Unfurnished
A/C
Central Air
Heating
Central

Exterior & Lot

Exterior Features
French Doors, Storage
Construction
Block, Stucco
Roof
Shingle
Foundation
Crawlspace
Patio/Porch
Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
Other Structures
Shed(s), Storage
Fencing
Vinyl
Lot Features
Paved

Water & Pool

Pool
Yes — In Ground, Screen Enclosure

Community & HOA

HOA
No
Pets Allowed
Yes
Security
Security System Owned

Utilities & Systems

Water
Public
Sewer
Septic Tank
Utilities
Public
Cooling
Central Air
Heating
Central
Flood Zone
X
Parking
Driveway

Financial

List Price
$519,000
Annual Taxes
$5,684
Tax Year
2025
Listing Terms
Cash, Conventional, FHA
Special Conditions
None
Possession
Close Of Escrow

Schools

Elementary
Lake Orienta Elementary
Middle School
Milwee Middle
High School
Lyman High

Virtual Tour

View Virtual Tour

Location