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
MLS #:
O6411336
Status:
Pending
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
DRUID HILLS ESTATES 1ST ADD
Neighborhood:
32751maitlandeatonville
Listed Date:
May 28, 2026
Finished Sq Ft:
1,929
Total Sq Ft:
2,609
Lot Size:
12,371 sqft / 0.28 acres (approx)
Year Built:
1958
See this Listing
Schools
Elementary School:
Lake Orienta Elementary
Middle School:
Milwee Middle
High School:
Lyman High
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Tile, Hardwood
Heating
Central
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat
Laundry Features
In Garage, Laundry Room
Levels
One
Exterior
Architectural Style
Florida, Ranch
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
East
Exterior Features
French Doors, Irrigation System, Storage
Fencing
Vinyl
Garage Spaces
2
Open Parking YN
1
Other Structures
Shed(s), Storage
Parking Features
Driveway
Patio And Porch Features
Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
Roof
Shingle
Security Features
Security System Owned
Window Features
Blinds
Financial
Tax Year
2025
Taxes
$5,684
Map
Community
- Address1065 GREGORY DR MAITLAND FL
- SubdivisionDRUID HILLS ESTATES 1ST ADD
- CityMAITLAND
- CountySeminole
- Zip Code32751
Subdivisions in MAITLAND
- ACREAGE & UNREC
- ADAMS GROVE
- BEG 635 FT E & 430 FT N OF SW COR OF SW1/4 OF NE1/
- BRANCH TREE
- BRITTANY GARDENS
- BUCHER HGTS
- CALHOUNS SUB
- CARRINGTON PARK A CONDO
- CHERRYWOOD GARDENS
- COFFINS SUB
- COMMONS AT MAITLAND CENTER SEC 02
- COOL-MORE SUB
- COOPERS SUB
- DIXIE TERRACE
- DOMMERICH
- DOMMERICH ESTATES 1ST ADD
- DOMMERICH ESTATES 2ND ADD
- DOMMERICH HILLS 2ND ADD
- DOMMERICH HILLS 3RD ADD
- DOMMERICH HILLS FIFTH ADD
- DOMMERICH HILLS SECOND ADD
- DOMMERICH WOODS
- DRUID HILLS
- DRUID HILLS PARK
- EATONVILLE
- ENCLAVE/MAITLAND A-F
- ENGLISH ESTATES UNIT 1
- ENGLISH ESTATES UNIT 2
- ENGLISH ESTATES UNIT 3
- ENGLISH ESTATES UNIT 4
- ENGLISH ESTS UNIT 1
- ENGLISH WOODS
- FOREST BROOK
- FOREST BROOK 3RD SEC
- FOREST BROOK 5TH SEC
- GREENWOOD GARDENS REP
- GREENWOOD GARDENS SEC 01
- HAMLET AT MAITLAND
- HIGHLAND PARK ESTATES FIRST ADD
- HOLDEN BROS SUB
- HOLLIEANNA SHORES
- HOLLIEANNA SHORES 1ST ADD
- INDIAN HILLS UNIT 1 REP
- INDIAN HILLS UNIT 9
- KINGS ROW
- LAKE EULALIA HEIGHTS
- LAKE FAITH VILLAS CONDO
- LAKE MAITLAND OWL PRESERVE
- LAKE MAITLAND TERRACE APTS
- LAKE SYBELIA COVE
- LAKEWOOD SHORES 1ST ADD
- MAITLAND CLUB
- MAITLAND EXCHANGE
- MAITLAND GROVE
- MAITLAND HARBOUR APTS
- MAITLAND VILLAGE
- MAITLAND WOODS
- MOORINGS ON LAKE MAITLAND CONDO
- MOORINGS ON LAKE MAITLAND CONDO BLDG 03
- MOORINGS ON LAKE MAITLAND CONDO BLDG 05
- NORTHGATE
- NORTHWOOD HEIGHTS
- OAKLAND SHORES
- OAKLAND SHORES 1ST ADD
- OAKLAND SHORES 3RD ADD REP
- OAKLEIGH 3RD ADD
- OAKWOOD
- ORANGEDALE PARK
- PACKWOODS PLAN/MAITLAND
- PARK LAKE GROVE CONDO PH B
- PARK LAKE SHORES
- PARK LAKE TOWNHOUSES
- PARK LAKE TWNHS
- PARK LAKE TWNHS PH 02
- PARK LAKE VILLAS CONDO
- PARK LAKE VILLAS CONDO CB 2/52
- PARK LAKE WOODS CONDO
- PRESERVE AT MAITLAND
- REPLAT BLK B POORS ADD
- RIDGEWOOD VILLAS CONDO
- ROOSEVELT PLACE
- SHOPPES/MAITLAND
- SIERRA CONDOMINIUMS
- STONEWOOD
- SUN BAY CLUB CONDO
- THOMPSON SUB
- ULTRA VISTA CONDO
- VERSAILLES
- VISCONTI EAST
- VISCONTI EST
- VISCONTI WEST
- VISCONTI WEST BLDG 3
- VISCONTI WEST BLDG 5
- VISCONTI WEST CONDO
- WEST COVE
- WINFIELD
- WOODBRIDGE
Market Summary
Current real estate data for Single Family in MAITLAND as of Jun 13, 2026
101
Single Family Listed
71
Avg DOM
353
Avg $ / SqFt
$1,033,576
Avg List Price
Property Summary
- Located in the DRUID HILLS ESTATES 1ST ADD subdivision, 1065 GREGORY DR MAITLAND FL is a Single Family for sale in MAITLAND, FL, 32751. It is listed for $519,000 and features 3 beds, 2 baths, and has approximately 1,929 square feet of living space, and was originally constructed in 1958. The current price per square foot is $269. The average price per square foot for Single Family listings in MAITLAND is $353. The average listing price for Single Family in MAITLAND is $1,033,576. To schedule a showing of MLS#o6411336 at 1065 GREGORY DR in MAITLAND, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
Similar Listings Nearby
Courtesy of EXP REALTY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 1065 GREGORY DR
MAITLAND, FL