$519,000
1065 Gregory Dr
Maitland, FL 32751
Listing updated: June 23, 2026 at 5:20 PM ET
Listing courtesy of Exp Realty Llc · Cece Wong · MLS #O6411336 · Active · 888-883-8509Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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!
Local Insight
This 1958 ranch sits at the sweet spot of Maitland's Family Starter tier—solid value at $269/sqft with a private pool and no HOA, but you're buying an older home that will likely need systems attention (roof, HVAC, plumbing) within the next few years, so factor that into your offer. The location is genuinely convenient for Maitland Center commuters, and the non-X flood zone is a real plus, though at 1,929 sqft on a modest 0.28-acre lot, you're getting more established neighborhood character than space—worth it if proximity to top-rated schools and a short commute matters more than square footage.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history15 days on market
- Status: ActiveJun 22, 2026
- Listed$519,000May 28, 2026
- Price increased$519,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 15
- Subdivision
- Druid Hills Estates 1st Add
- County
- Seminole
- Year built
- 1958
- Living area
- 1,929 sq ft
- Price/sq ft
- $269
- Building area
- 2,609 sq ft (Public Records)
- Lot size
- 12,371 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $5,684 (2025)
- Parcel #
- 24-21-29-507-0A00-0120
- Zoning
- R-1AA
- MLS #
- O6411336
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Flooring
- Tile, Wood
- Appliances
- Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Interior features
- Ceiling Fans(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat
- Laundry
- In Garage, Laundry Room
- Stories / Levels
- One
- Direction faces
- East
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Driveway
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional, FHA
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Buyer and Buyer's Agent's responsibility to verify leasing restrictions with the county.
Exterior & Construction
- Exterior features
- French Doors, Storage
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Crawlspace
- Pool
- Private pool
- Road surface
- Asphalt
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- Public
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | 13x12 |
| Primary Bathroom | First | 8x4 |
| Bedroom 2 | First | 11x12 |
| Bedroom 3 | First | 11x12 |
| Bonus Room | First | 19x19 |
| Bathroom 2 | First | 5x7 |
| Living Room | First | 15x20 |
| Dining Room | First | 10x11 |
| Kitchen | First | 12x10 |
| Family Room | First | 12x15 |
| Balcony/Porch/Lanai | First | 10x23 |
Listing Details
- Listing date
- 2026-05-28
- On market date
- 2026-05-28
- Original list price
- $519,000
- Occupant type
- Owner
- MLS area
- 32751 - Maitland / Eatonville
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-06-22
- Tax legal description
- LOT 12 BLK A DRUID HILLS ESTATES 1ST ADD PB 11 PG 42
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From 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.
Listings courtesy of Stellar MLS as distributed by MLS GRID
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.
Based on information submitted to the MLS GRID as of June 23, 2026 at 5:20 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA