$519,000

1065 GREGORY DR, Maitland, FL 32751

Active
3
Beds
2
Baths
1,929
Sq Ft
$269
Per Sq Ft
1958
Built
20
Days Listed

About This Property

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

TypeSingle Family Residence
Garage2 spaces
Lot0.28 ac
PoolYes
WaterfrontNo
SubdivisionDRUID HILLS ESTATES 1ST ADD
HOANo
Tax/yr$5,684
HeatingCentral
CoolingCentral Air
FlooringTile, Wood
RoofShingle

Schools

ElementaryLake Orienta Elementary
MiddleMilwee Middle
High SchoolLyman High

Listed by EXP REALTY LLC · MLS# O6411336

Similar Homes in 32751

View all Homes For Sale in 32751 →

Recently Sold in 32751

341 CHERRYWOOD GARDENS DR #2
$185,600
341 CHERRYWOOD GARDENS DR #2, 32751
2 bd · 2 ba · 905 sqft
Sold Jun 2026
190 W VENTRIS AVE
$1,595
190 W VENTRIS AVE, 32751
2 bd · 1 ba · 770 sqft
Sold Jun 2026
400 W TROTTERS DR
$985,000
400 W TROTTERS DR, 32751
4 bd · 4 ba · 3,397 sqft
Sold Jun 2026

Properties displayed may be listed or sold by various participants in the MLS


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved. Data deemed reliable but not guaranteed. Last updated: 2026-06-28.
IDX information is provided exclusively 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.
Schedule a Showing
Rise Team · LPT Realty, LLC
Mike Valdes
Mike Valdes
Rise Team · LPT Realty
(813) 548-5618
Browse More

🏠 Open House

Sunday, Jun 28
11:00 AM – 1:00 PM EDT
+ Add to Calendar

Monthly Payment

Estimate your all-in monthly cost.

%
%
EST. MONTHLY PAYMENT

Estimate only. Taxes, insurance, and HOA may vary.

🔔

Get notified of similar listings

Be the first to know when a similar home hits the market.

Sign up free to get alerts

Already a member? Log in

Property photo
🤖

Rise AI Assistant

Ask anything about this listing