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$519,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,929 Sq. Ft.
  • Updated 30 minutes ago

Next open house:

Open House: 10:00 AM - 12:00 PM

Saturday 5/30 10:00 AM - 12:00 PM

1065 Gregory Dr,Maitland, FL 32751

1065 Gregory DrMaitlandFL32751

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VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home on over a ¼ acre offers something rare: a spacious 4th room addition with its own separate entrance in driveway and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, income-producing suite, or dedicated learning space - with no HOA to answer to. The main house features 3 bed/2bath and 2 separate living areas with a split bedroom floor plan. The cozy fireplace and hardwood floors 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!

Full Property Details for 1065 Gregory Dr

General

  • Price: $519,000
  • Taxes: $5,684 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6411336
  • Updated: Today (5/28/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 11
  • Interior Features: Ceiling Fan(s), Kitchen and Family Room Combination, Primary Bedroom Main Floor, Split Bedroom, Thermostat
  • Fireplace: Yes
  • Fireplace(s): Living Room, Wood Burning
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: In Garage, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Screen Enclosure
  • Security/Safety: Security System Owned

Exterior

  • Exterior Features: French Doors, Irrigation System, Storage
  • Deck/Patio: Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Enclosed, Front Porch, Patio, Porch, Rear Porch, Screen

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway

Location

  • Area: 32751 - Maitland / Eatonville
  • County: Seminole
  • Development Name: 32751 - Maitland / Eatonville
  • Subdivision: DRUID HILLS ESTATES 1ST ADD
  • Driving 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.
  • Direction Faces: East

School Information

  • Elementary School: Lake Orienta Elementary
  • Middle School: Milwee Middle
  • High School: Lyman High

Community

  • Community Name: 32751 - Maitland / Eatonville
  • Pet Restrictions: Buyer and Buyer's Agent's responsibility to verify pet restrictions with the county.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Public

Structural Information

  • Architectural Info: Florida, Ranch
  • Architectural Style: Florida, Ranch
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Blinds
  • Stories/Levels: One
  • Square Feet: 1,929
  • Sq. Ft. Source: Public Records
  • Year Built: 1958

Additional Structures

  • Other Structures: Shed(s), Storage

Lot Features

  • Lot Size (Acres): 0.28
  • Lot Size (Sq. Ft.): 12,371
  • Lot Size: 12371
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Vinyl

Financial Considerations

  • Tax Amount: $5,684
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 12 BLK A DRUID HILLS ESTATES 1ST ADD PB 11 PG 42
  • Flood Zone Info: X
  • APN: 2421295070A000120
  • Property ID: 2421295070A000120
  • Block/Lot/Section: A

Listed by Exp Realty Llc

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— 1065 Gregory Dr —

  • Exp Realty Llc

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1065 Gregory Dr

School District:Seminole County School District
NameGradesDistance
Lake Orienta Elementary School
612 Newport Avenue, Altamonte Springs, FL 32701
K-50.6 mi
Lyman High School
865 South Ronald Reagan Boulevard, Longwood, FL 32750
9-123.7 mi
Milwee Middle School
1341 S Ronald Reagan Blvd, Longwood, FL 32750
6-83.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1065 Gregory Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/28/2026
Listed
$519,000
16.63%
MLS
11/10/2021
Sold
$445,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1065 Gregory Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,684
-1%
$416,920
2%
2024
$5,765
7%
$410,724
8%
2023
$5,390
70%
$379,470
53%
2021
$3,162
-37%
$248,722
-29%
2022
$5,023
59%
$349,622
43%
2021
$3,162
2%
$245,288
2%
2019
$3,104
110%
$239,773
93%
2018
$1,480
1%
$124,198
2%
2017
$1,465
-42%
$121,643
-19%
2016
$2,505
50%
$149,324
15%
2015
$1,673
1%
$129,898
1%
2014
$1,654
-1%
$128,867
1%
2013
$1,673
—
$126,963
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Exp Realty Llc

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1065 Gregory Dr, Maitland, FL 32751 (MLS# O6411336) is a Single Family property with 4 bedrooms and 2 full bathrooms. 1065 Gregory Dr is currently listed for $519,000 and was received on May 28, 2026. Want to learn more about 1065 Gregory Dr? Do you have questions about finding other Single Family real estate for sale in Maitland? You can browse all Maitland real estate or contact a Coldwell Banker agent to request more information.

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