1065 GREGORY DR, MAITLAND, FL 32751

3 Beds

2 Full baths

1,929SqFt

Active

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!

Property Details
Price $519,000
Bedrooms 3
Full Baths 2
Half Baths 0
Property Style Florida, Ranch
Lot Size Area 12371
Lot Size Area Units Square Feet
Acres 0.28
Property Type Residential
Sub type SingleFamilyResidence
MLS Sub type Single Family Residence
Features Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat
Exterior Features French Doors, Irrigation System, Storage
Year Built 1958
Subdivision DRUID HILLS ESTATES 1ST ADD
Roof Shingle
Heating Central
Foundation Crawlspace
Laundry Features In Garage, Laundry Room
Pool features In Ground, Screen Enclosure
Parking Description Driveway
Garage spaces 2
Geographic Data
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.
County Seminole
Latitude 28.641613
Longitude -81.377382
Market Area 32751 - Maitland / Eatonville
Address Information
Address 1065 GREGORY DR, MAITLAND, FL 32751
Postal Code 32751
City MAITLAND
State FL
Country United States
Listing Information
Listing Office EXP REALTY LLC
Listing Agent Cece Wong
Special listing conditions None
Ownership Fee Simple
Terms Cash, Conventional, FHA
Virtual Tour URL https://player.vimeo.com/video/1196194213?h=66d5dd2252&badge=0&autopause=0&player_id=0&app_id=58479
School Information
Elementary School Lake Orienta Elementary
Middle School Milwee Middle
High School Lyman High
MLS Information
Days on market 20
MLS Status Active
Listing Date May 28, 2026
Listing Last Modified Jun 28, 2026
Tax ID 2421295070A000120
Tax Year 2025
Tax Annual Amount 5684
MLS Area 32751 - Maitland / Eatonville
MLS # O6411336

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