Curious about this home?

Ask anything — no agents, no pressure

Try asking

About This Home

This 4-bedroom, 2-bathroom single family at 1065 GREGORY DR in Maitland, FL is listed for $519,000 ($269 per sqft). Built in 1958, the home offers 1,929 sqft of living space on a 0.28 acres lot.

Agent Description

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!

Key Features

  • Built in 1958
  • 0.28 acre lot
  • Private pool
  • Fireplace

Property Details

2 full
1958

Amenities

PoolFireplace

Monthly Cost Estimate

$2,776/mo

20% down · 6.5% · 30 years

Principal$375
Interest$2,249
Insurance$151

Estimates only. Actual payments may vary.

Location

1065 GREGORY DR

Maitland, FL 32751

DRUID HILLS ESTATES 1ST ADD

Features & Amenities

Interior Features

Ceiling Fans(s)Kitchen/Family Room ComboPrimary Bedroom Main FloorSplit BedroomThermostat

Exterior Features

PavedFencingFrench DoorsStoragePool

Property Details

Flooring

TileWood

Construction

BlockStucco

Parking

DrivewayGarageGarage - Attached

Heating

CentralFireplace(s)

Cooling

Central Air

Appliances

DishwasherDryerMicrowaveRangeRefrigeratorWasher

Questions & Answers

This 4-bedroom, 2-bathroom single family at 1065 GREGORY DR is listed at $519,000 ($269/sqft). The estimated monthly payment is $2,249 based on 20% down at 6.5% interest.

Key features include: Built in 1958, 0.28 acre lot, Private pool, Fireplace. Interior Features: Ceiling Fans(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor. Exterior Features: Paved, Fencing, French Doors.

This property is listed by Cece Wong and can be reached at 4078091440 or cece.wong@exprealty.com.

CW

Cece Wong

Agent at EXP REALTY LLC

(407) 809-1440

Listed by EXP REALTY LLC · View on Broker Site

MLS# O6411336· Source: listhub· Updated 4 days ago

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

1065 GREGORY DR, Maitland, FL 32751

Open this listing in: