# 1065 GREGORY DR, Maitland, FL 32751

> **TL;DR:** 4bd/2ba single family, $519,000 ($269/sqft), built 1958, 1,929 sqft.
> Pool, Fireplace. Est. $2,249/mo. Listed 4 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $519,000 |
| Price/sqft | $269 |
| Bedrooms | 4 |
| Bathrooms | 2 full |
| Square Feet | 1,929 |
| Year Built | 1958 |
| Lot Size | 12,197 sqft (0.28 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 4 |

## Why This Home Stands Out

- **Pool** - Private pool

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $2,249 |
| **Total** | **$2,249** |

## Nearby Schools

- **Elementary:** Lake Orienta Elementary
- **Middle:** Milwee Middle
- **High:** Lyman High

## Key Amenities

- Pool
- Fireplace

## Property Highlights

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

## Description

### 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!

## Location

- **Address:** 1065 GREGORY DR, Maitland, FL 32751
- **County:** Seminole
- **Neighborhood:** DRUID HILLS ESTATES 1ST ADD
- **Coordinates:** 28.641613, -81.377382
- **Google Maps:** https://www.google.com/maps?q=28.641613,-81.377382

## Listing Agent

- **Name:** Cece Wong
- **Brokerage:** EXP REALTY LLC
- **Phone:** 4078091440
- **Email:** cece.wong@exprealty.com

## Primary Photo

![1065 GREGORY DR - Primary Photo](http://lh.rdcpix.com/3f5d308bd651a8b47cb929dd1d0016b8l-f541489726r.jpg)

*37 total photos available on [listing page](https://www.propertysimple.com/listing/1065-gregory-dr-maitland-fl-32751-o6411336)*

---

**MLS#:** O6411336 | **Updated:** 2026-06-18
**Source:** listhub

*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.*

[View on PropertySimple](https://www.propertysimple.com/listing/1065-gregory-dr-maitland-fl-32751-o6411336)

---

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