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$529,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,734 Sq. Ft.
  • Updated 2 hours ago

Next open house:

Open House: 5:00 PM - 7:00 PM

Friday 10/2 5:00 PM - 7:00 PM

1060 Gregory Drive,Maitland, FL 32751

1060 Gregory DriveMaitlandFL32751

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Join us at 1060 Gregory Drive on:

  • Open House: 1:00 PM - 4:00 PM

    Saturday 10/3 1:00 PM - 4:00 PM

    1060 Gregory Drive,Maitland, FL 32751
    1060 Gregory DriveMaitlandFL32751
  • Open House: 1:00 PM - 4:00 PM

    Sunday 10/4 1:00 PM - 4:00 PM

    1060 Gregory Drive,Maitland, FL 32751
    1060 Gregory DriveMaitlandFL32751
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See This Home
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Some homes have a character that simply cannot be recreated-and 1060 Gregory Drive is one of them. Built in 1962 and tucked beneath mature oaks draped in Spanish moss, this three-bedroom, two-bath Maitland home celebrates its original charm while offering the updates today's buyers appreciate. Warm hardwood floors flow through the home, while a dramatic brick feature wall separates the living and family rooms, with a fireplace facing each space. It is a memorable architectural detail that makes both rooms feel welcoming and distinct. The updated kitchen pairs shaker-style cabinetry with granite countertops and stainless steel appliances, while plantation shutters and ceiling fans add comfort and classic style throughout. The primary bedroom features a walk-in closet and updated ensuite bath with a new quartz topped vanity. The guest bathroom also benefits from a new vanity. Step outside to an expansive backyard deck with plenty of room for dining, entertaining and lingering beneath the trees on beautiful Florida evenings. Major improvements include an ELECTRICAL UPDATE 2026, ALL NEW DUCTWORK 2026, REPIPED 2025, HVAC and REROOF 2020, WATER HEATER 2022, along with a NEW FENCE installed in 2023. Set in an established Maitland neighborhood with quick access to Winter Park, Maitland and Interstate 4, this is a home with a story, a setting and a style all its own. Come experience the character, comfort and tree-lined charm that make 1060 Gregory Drive feel like home from the moment you arrive.

Full Property Details for 1060 Gregory Dr

General

  • Price: $529,000
  • Taxes: $2,349 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6445281
  • Updated: Today (10/1/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 6
  • Interior Features: Primary Bedroom Main Floor, Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Family Room, Wood Burning
  • Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: In Garage

Exterior

  • Exterior Features: French Doors, Private Yard, Rain Gutters
  • Deck/Patio: Covered, Front Porch
  • Porch/Patio/Deck: Covered, Front Porch

Parking

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

Location

  • Area: 32751 - Maitland / Eatonville
  • County: Seminole
  • Development Name: 32751 - Maitland / Eatonville
  • Subdivision: DRUID HILLS ESTATES 1ST ADD
  • Driving Directions: From the intersection of North Maitland Avenue and Oranole Road, head west on Oranole, left on Gregory Drive and the home is on the left.
  • Direction Faces: West

School Information

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

Community

  • Community Name: 32751 - Maitland / Eatonville

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Public, Water Connected

Structural Information

  • Architectural Info: Florida
  • Architectural Style: Florida
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,734
  • Sq. Ft. Source: Public Records
  • Year Built: 1962

Lot Features

  • Lot Size (Acres): 0.28
  • Lot Size (Sq. Ft.): 12,386
  • Lot Size: 12386
  • Lot Dimensions: 117 x 105
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt

Financial Considerations

  • Tax Amount: $2,349.01
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 7 BLK B DRUID HILLS ESTATES 1ST ADD PB 11 PG 42
  • Flood Zone Info: X
  • APN: 2421295070B000070
  • Property ID: 2421295070B000070
  • Block/Lot/Section: B

Listed by Keller Williams Winter Park

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— 1060 Gregory Dr —

  • Keller Williams Winter Park

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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

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Schools serving 1060 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
9-123.6 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 1060 Gregory Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/01/2026
Listed
$529,000
112.88%
MLS
3/19/2014
Sold
$248,500
—
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 1060 Gregory Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,435
-4%
$217,575
3%
2024
$2,538
3%
$211,443
3%
2023
$2,474
6%
$205,284
6%
2021
$2,331
-3%
$193,500
-3%
2022
$2,406
3%
$199,305
4%
2021
$2,331
4%
$190,828
4%
2018
$2,252
-1%
$183,060
-2%
2019
$2,281
2%
$186,538
4%
2017
$2,233
-2%
$179,295
2%
2016
$2,272
-4%
$175,607
1%
2015
$2,375
46%
$174,386
38%
2014
$1,626
-1%
$126,195
2%
2013
$1,644
—
$124,330
—
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 Keller Williams Winter Park

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1060 Gregory Drive, Maitland, FL 32751 (MLS# O6445281) is a Single Family property with 3 bedrooms and 2 full bathrooms. 1060 Gregory Drive is currently listed for $529,000 and was received on October 01, 2026. Want to learn more about 1060 Gregory Drive? 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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