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1065 GREGORY DR

House For Sale
$519,000

BTC: 8.10937500

ETH: 297.25085911

6 days
3 bds
2 ba
1,929 sqft

Overview

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!

Location

Details

Type:
Residential
Parking:
Driveway
Year Built:
1958
Lot:
0.28 Acres
Heating:
Central
Price/sqft:
$269
Cooling:
Central Air
HOA:
No Data

Valuation

Our model vs. what's actually selling nearby.
Estimate
$409,000
$261K – $745K
Confidence Low
List vs. estimate
$110K above estimate
List $519,000 · +26.9%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$269
-15.5% vs. city median $318
Based on
15 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$5,684
2025
Pool
In Ground
Garage
2 car garage
Pets
Allowed
All facts and features
  • Flooring

    • Tile

    • Hardwood

    Heating

    • Central

    Cooling

    • Central Air

    Appliances

    • Dishwasher

    • Dryer

    • Microwave

    • Range

    • Refrigerator

    • Washer

    Other interior features

    • Ceiling Fan(s)

    • Kitchen/Family Room Combo

    • Primary Bedroom Main Floor

    • Split Bedroom

    • Thermostat

    Bedrooms and bathrooms

    • Bedrooms: 3

    • Full bathrooms: 2

  • Parking

    • Driveway

    Property

    • Levels: One

    • Pool Private: Yes

    • Exterior Features: French Doors / Irrigation System / Storage

    Lot

    • Lot: 0.28 Acres

    Other Property Information

    • Parcel Number: 2421295070A000120

    • Zoning: R-1AA

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • Public

  • Other financial information

    • Annual tax amount: $5,684

  • Source details

    • MLS ID: O6411336

    Other facts

    • Construction Materials: Block / Stucco

    • Foundation Details: Crawlspace

    • Fireplace Features: Living Room / Wood Burning

    • Laundry Features: In Garage / Laundry Room

    • Patio And Porch Features: Enclosed / Front Porch / Patio / Porch / Rear Porch / Screened

    • Pool Features: In Ground / Screen Enclosure

    • Window Features: Blinds

    • Direction Faces: East

    • Other Structures: Shed(s) / Storage

    • Architectural Style: Florida / Ranch

    • Fireplace: Yes

    • Garage Spaces: 2

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 1929

    • Water Source: Public

    • Subdivision Name: DRUID HILLS ESTATES 1ST ADD

Private inquiry
Talk to the advisor on this listing.
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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: EXP REALTY LLC