MAITLAND, FL 32751 1065 GREGORY DR

OPEN HOUSE Sat, Jun 13 2026 11:00 AM - 02:00 PM
1065 GREGORY DR MAITLAND, FL - Image 11065 GREGORY DR MAITLAND, FL - Image 21065 GREGORY DR MAITLAND, FL - Image 3
32 more
1065 GREGORY DR MAITLAND, FL - Image 41065 GREGORY DR MAITLAND, FL - Image 51065 GREGORY DR MAITLAND, FL - Image 61065 GREGORY DR MAITLAND, FL - Image 71065 GREGORY DR MAITLAND, FL - Image 81065 GREGORY DR MAITLAND, FL - Image 91065 GREGORY DR MAITLAND, FL - Image 101065 GREGORY DR MAITLAND, FL - Image 111065 GREGORY DR MAITLAND, FL - Image 121065 GREGORY DR MAITLAND, FL - Image 131065 GREGORY DR MAITLAND, FL - Image 141065 GREGORY DR MAITLAND, FL - Image 151065 GREGORY DR MAITLAND, FL - Image 161065 GREGORY DR MAITLAND, FL - Image 171065 GREGORY DR MAITLAND, FL - Image 181065 GREGORY DR MAITLAND, FL - Image 191065 GREGORY DR MAITLAND, FL - Image 201065 GREGORY DR MAITLAND, FL - Image 211065 GREGORY DR MAITLAND, FL - Image 221065 GREGORY DR MAITLAND, FL - Image 231065 GREGORY DR MAITLAND, FL - Image 241065 GREGORY DR MAITLAND, FL - Image 251065 GREGORY DR MAITLAND, FL - Image 261065 GREGORY DR MAITLAND, FL - Image 271065 GREGORY DR MAITLAND, FL - Image 281065 GREGORY DR MAITLAND, FL - Image 291065 GREGORY DR MAITLAND, FL - Image 301065 GREGORY DR MAITLAND, FL - Image 311065 GREGORY DR MAITLAND, FL - Image 321065 GREGORY DR MAITLAND, FL - Image 331065 GREGORY DR MAITLAND, FL - Image 341065 GREGORY DR MAITLAND, FL - Image 351065 GREGORY DR MAITLAND, FL - Image 36
Presented By: EXP REALTY LLC with 888-883-8509. - 888-883-8509
  • MLS# O6411336
  • 05/28/2026
  • Request Tour
  • Request Info
Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 3
  • Baths • 2
  • SQFT • 1,929
  • Garage • 2

Home Details

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!
Presented By: EXP REALTY LLC with 888-883-8509. - 888-883-8509

Interior Features for 1065 GREGORY DR

Bedrooms

Total Bedrooms3

Bathrooms

Half Baths0
Total Baths2

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace FeaturesLiving Room, Wood Burning
Fireplace Y/NYes
FlooringTile, Hardwood
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesCeiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat
Laundry FeaturesIn Garage, Laundry Room
Window FeaturesBlinds

General for 1065 GREGORY DR

Additional Parcels Y/NNo
Additional RoomsBonus Room
AppliancesDishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Architectural StyleFlorida, Ranch
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityMAITLAND
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountySeminole
DirectionsFrom 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.
DockY/NNo
Elementary SchoolLake Orienta Elementary
Facing DirectionEast
Flood Zone CodeX
Flood Zone Code XY
Full Baths2
Garage Spaces2
Garage Y/NYes
HeatingCentral
High SchoolLyman High
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionLOT 12 BLK A DRUID HILLS ESTATES 1ST ADD PB 11 PG 42
LevelsOne
Listing TermsCash, Conventional, FHA
Living Area UnitsSquare Feet
Lot Size Square Feet12371
Lot Size UnitsSquare Feet
MLS Area32751 - Maitland / Eatonville
Middle/Junior High SchoolMilwee Middle
Minimum LeaseNo Minimum
New ConstructionNo
Occupancy TypeOwner
Other StructuresShed(s), Storage
OwnershipFee Simple
Patio/Porch FeaturesEnclosed, Front Porch, Patio, Porch, Rear Porch, Screened
Pets AllowedYes
Pool FeaturesIn Ground, Screen Enclosure
PossessionClose Of Escrow
Property SubtypeSingle Family Residence
Property TypeResidential
RoofShingle
STELLAR_InLawSuiteYNNo
Security FeaturesSecurity System Owned
Senior Community Y/NNo
SewerSeptic Tank
Standard StatusActive
StatusActive
Subdivision NameDRUID HILLS ESTATES 1ST ADD
Tax Annual Amount5684
Tax Lot12
Tax Year2025
Total Rooms11
UtilitiesPublic
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built1958
ZoningR-1AA

Exterior for 1065 GREGORY DR

Building Area Total2609
Covered Spaces2
Exterior AmenitiesFrench Doors, Irrigation System, Storage
FencingVinyl
Foundation DetailsCrawlspace
Lot Size Acres0.28
Lot Size Area12371
Parking FeaturesDriveway
Private PoolYes
Road Frontage TypeStreet Paved
Road ResponsibilityPublic Maintained Road
Road Surface TypePaved, Asphalt
VegetationMature Landscaping
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Pugh

Broker Associate | Team Leader
Price $519,000
MLS#O6411336
List Date 05/28/2026
Property Type Single Family
Request Tour
Request Info
Visit My Website

Similar Properties to 1065 GREGORY DR

MLS® Disclaimer

MLS Logo Copyright © MFRMLS.com All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of MFR MLS. All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

33. Required DMCA Notice

DMCA Disclaimer

The Digital Millennium Copyright Act of 1998, 17 U.S.C. §512, the DMCA, provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owners behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.