New Listing
Open House LogoIn-Person: 10/03 1:00 PM - 4:00 PM
In-Person: 10/04 1:00 PM - 4:00 PM
$529,000
 $2,840 est/mo Sourced by Back At You

1060 Gregory Dr,MAITLAND, FL 32751

MAITLAND, FL 32751

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Description

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 dual closets. 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, HVAC and REROOF 2020, WATER HEATER 2022, a NEW FENCE installed in 2023 and REPIPED 2009. 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.

Details

MLS #O6445281
Listing TypeFor Sale
StyleHouse
Sub-TypeFor-sale
StatusActive
Year1962
Days On Site2
Listing Provided ByKELLER WILLIAMS WINTER PARK | Jill Healey

Features

Bed(s)3
Bath(s) 2 Total
SQ Feet1,734
Garage2
Story(s)1
ZoningR-1AA
Acreage0.28

Taxes

Property2349

Area Information

StateFL
CountySeminole
CityMAITLAND
Zip Code32751
Area32751 Maitland | Eatonville
Community NameDRUID HILLS ESTATES 1ST ADD
School DistrictLyman High
Elementary SchoolLake Orienta Elementary
High SchoolLyman High
Listing VS Median (in DRUID HILLS ESTATES 1ST ADD)
Price:
$529,000
low | high
Med:
$539,000
48.109640831758% of Average
sqft:
1,734
low | high
Med:
1,709
51.441753171857% of Average
$ / sqft:
$305
low | high
Med:
$316
46.568953207998% of Average
On site:
2
low | high
Med:
42
4.761904761905% of Average
Sourced by Back At You

Market Activity 32751

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 Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of October 3, 2026 at 12:41:10 AM PDT 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. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

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Learn More About This Property

Open House
In-Person
10/03 1:00 PM - 4:00 PM
In-Person
10/04 1:00 PM - 4:00 PM
StateFL
CountySeminole
CityMAITLAND
Zip Code32751
Area32751 Maitland | Eatonville
Community NameDRUID HILLS ESTATES 1ST ADD
School DistrictLyman High
Elementary SchoolLake Orienta Elementary
High SchoolLyman High
Listing VS Median (in DRUID HILLS ESTATES 1ST ADD)
Price:
$529,000
low | high
Med:
$539,000
48.109640831758% of Average
sqft:
1,734
low | high
Med:
1,709
51.441753171857% of Average
$ / sqft:
$305
low | high
Med:
$316
46.568953207998% of Average
On site:
2
low | high
Med:
42
4.761904761905% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $396K - $661K
sqft: 1,000 - 2,000
Nearby Listings Property ImageNearby Listings Details
1055 DRUID DR Property Photo 1
$549,000
1055 Druid Dr
Maitland, FL 32751
Listing Updated: October 3, 2026 at 12:41:10 AM PDT