1065 Gregory Dr, Maitland, FL 32751
PENDING
3D VIEW
0.28 ACRES

1065 Gregory Dr
Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,929 sqft (on 0.28 acres)

$519,000

Est. Mortgage $3,574/mo*
Get Pre-Qualified

$519,000

Est. Mortgage $3,574/mo*
Get Pre-Qualified
3 Beds
2 Baths
1,929 sqft
(on 0.28 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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!

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio, Pool
View
No Info
HOA
None
Price/Sqft
$269
Listed
20 days ago

Home Details for 1065 Gregory Dr

Interior Features

Interior Details
Number of Rooms: 11Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Bathroom 2, Balcony Porch Lanai, Bonus Room, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1929 Square Feet
Appliances & Utilities
Utilities: PublicAppliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, WasherDishwasherDryerLaundry: In Garage,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living Room, Wood BurningHas a Fireplace
Windows, Doors, Floors & Walls
Window: BlindsDoor: French DoorsFlooring: Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Tile, Hardwood
View
No View
Security
Security: Security System Owned

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Enclosed, Front Porch, Patio, Porch, Rear Porch, ScreenedFencing: VinylVegetation: Mature LandscapingOther Structures: Shed(s), StorageExterior: Irrigation System, StorageFoundation: CrawlspaceHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway
Pool
Pool: In Ground, Screen EnclosurePool
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 14Days on Market: 20

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Florida,Ranch
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 2421295070A000120

Price & Status

Price
List Price: $519,000Price Per Sqft: $269
Status Change & Dates
Off Market Date: Thu Jun 11 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Pending

Media

Location

Direction & Address
City: MAITLANDCommunity: DRUID HILLS ESTATES 1ST ADD
School Information
Elementary School: Lake Orienta ElementaryJr High / Middle School: Milwee MiddleHigh School: Lyman High

Agent Information

Listing Agent
Listing ID: O6411336

Building

Building Area
Building Area: 2609 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Sarasota - ManateeNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 0.28 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6411336Showing Considerations: See RemarksShowing Requirements: Appointment Only, Lockbox - Electronic, See Remarks, ShowingTimeUniversal Property Id: US-12117-N-2421295070000120-R-N
Last check for updates: about 13 hours ago
Listing Provided by: Cece Wong, (407) 809-1440
EXP REALTY LLC, (888) 883-8509
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#O6411336
Also Listed on Stellar MLS, eXp Realty.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Market trends in Maitland

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
119
5MoM

Price History for 1065 Gregory Dr

DatePriceEventSource
06/12/2026$519,000PendingeXp Realty #O6411336
05/28/2026$519,000Listed For SaleStellar MLS #O6411336
11/11/2024$425,000ListingRemovedStellar MLS #O5975285
11/11/2023ListingRemovedStellar MLS #O5975285
11/17/2021$445,000Sold
N/A
09/27/2021$425,000PendingStellar MLS #O5975285
09/24/2021$425,000Listed For SaleStellar MLS #O5975285
03/16/2018$285,000Sold
N/A
02/09/2018$285,000PendingAgent Provided
02/08/2018$285,000Listed For SaleAgent Provided
07/08/2016$262,500Sold
Stellar MLS #O5395746
06/24/2016$262,500PendingAgent Provided
06/03/2016$262,500PriceChange
Agent Provided
02/03/2016$288,500PriceChange
Agent Provided
10/26/2015$298,500PriceChange
Agent Provided
10/02/2015$325,000Listed For SaleAgent Provided
05/03/1999$139,800Sold
N/A
11/13/1995$95,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$6,068
Assessment$416,920
Home facts updated by county records

Comparable Sales for 1065 Gregory Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1004 Gregory Dr, Maitland, FL
0.04
Single-Family Home
$550,000
10/14/25
3
2
1,835
444 Stonewood Ln, Maitland, FL
0.17
Single-Family Home
$550,000
10/14/25
3
2
2,188
408 Monticello Dr, Altamonte Springs, FL
0.18
Single-Family Home
$503,000
04/15/26
4
2
2,036
344 Banyan Dr, Maitland, FL
0.22
Single-Family Home
$398,000
05/15/26
3
2
1,408
380 Banyan Dr, Maitland, FL
0.15
Single-Family Home
$400,000
01/16/26
3
2
1,404
354 Hickory Dr, Maitland, FL
0.17
Single-Family Home
$401,000
05/13/26
3
2
1,395
417 Monticello Dr, Altamonte Springs, FL
0.24
Single-Family Home
$520,000
08/15/25
4
2
2,077
363 Croton Dr, Maitland, FL
0.13
Single-Family Home
$350,000
11/24/25
3
2
1,386
815 Arlington Blvd, Altamonte Springs, FL
0.32
Single-Family Home
$575,000
06/12/26
3
2
2,055

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 1065 Gregory Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Maitland

At least 169 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 85 % Say car is needed

  • 80 % Say there are sidewalks

  • 79 % Say parking is easy

  • 72 % Say there's holiday spirit

  • 66 % Say streets are well-lit

  • 65 % Say it's quiet

  • 65 % Say people would walk alone at night

  • 58 % Say kids play outside

  • 55 % Say yards are well-kept

  • 52 % Say it's walkable to restaurants

  • 51 % Say it's walkable to grocery stores

  • 48 % Say neighbors are friendly

  • 45 % Say they plan to stay for at least 5 years

  • 40 % Say there's wildlife

  • 30 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Nickwilson1997.nw
    "Very homey and friendly. Feels very safe and around many things. Great schools and work places to be around "
    0
    Flag
  • Che F
    "Lots of dogs, mostly all on leash and well behaved. Most of the local restaurants are dog friendly as well."
    0
    Flag
  • Winterparkhomes
    "Lots of dog friendly places and parks located throughout the City of Maitland and surrounding areas. "
    0
    Flag
  • Jdburry
    "Many community events and a private neighborhood boat dock. Two parks nearby with tennis, pickleball, basketball, walking trails with exercise equipment. Bicycle routes as well."
    0
    Flag
  • Emmrickgarca
    "Schools are good! The library in WinterPark is really close. We’re about to get a new library in Maitland."
    0
    Flag
  • Jeane hennessy
    "It has all the stores around here. I feel safe working and living here. The traffic is not bad. Lots of trees. "
    0
    Flag
  • Amber H. .
    "Safe and clean always see many parents out walking with there kids and the city maintains to streets and planters "
    8
    Flag
  • Arelis R.
    "I’ve lived here for two years. People are friendly there is no crime and I feel safe when I go running alone very early in the morning and late at night. It’s clean and I have never had a package stolen from outside my door. I wish every neighborhood was this safe ! "
    1
    Flag
  • Pennyalberry
    "Plenty of nice areas for walks around the lakes. Many restaurants offer and love catering to dog owners with snacks, food, treats and water available."
    1
    Flag
  • Mandy M.
    "Maybe monthly popcorn and free movies in the park, monthly city block party, weekly farmers market, plenty of parks, trees, and space for bicycle rides."
    1
    Flag
  • Jonathan H.
    "You will like the dog friendly community. You want like the fact that dog parks are non existent. But all in all a great neighborhood. "
    0
    Flag
  • Giovanni L.
    "The commute to the highways and shopping is very close as well. There are public transportation routes as well. "
    0
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  • Christen R.
    "It’s a growing area and everything is always changing but there is a lot of apartments being built in a concentrated area that leads to the i4 which will one day create a lot of traffic."
    1
    Flag
  • Jennifer D.
    "The area is nice. It seems safe for families of all kinds. I’m not sure about the schools because I don’t have children. But the parks are very nice. "
    2
    Flag
  • Jonathan H.
    "I’ve lived in this neighborhood for five years and I love it. Quiet and Quaint. Easy access to Orlando, attractions and surrounding entertainment. "
    0
    Flag
  • Nicolerossi1003
    "I’ve lived in Maitland for over 12 years. It’s a great community but within the last couple of years, the apartment complexes have gone up surrounding the area which makes traffic unbearable at times."
    2
    Flag
  • Crhayman
    "It has both suburban and urban elements, and quality elementary schools and a good middle school. The Enzian movie theatre also makes it unique. "
    0
    Flag
  • Lisarulesall
    "Its somewhat quiet. There are nostly office buildings. Plenty of grocery stores. Cute library. Close to I4. Itll be walkable to sun rail soon. "
    1
    Flag
  • Elizabeth H.
    "Sheriff picnics, outdoor movies, farmers market, and various sports games. Apartment complex does events like waffle Wednesdays"
    1
    Flag
  • Rhonda T.
    "This is a great place to raise a family or to enjoy retirement. I love all the parks and lakes great shopping and entertainment. "
    3
    Flag
  • elle
    "There is not enough grass for dogs to walk and no where on the property for pets to run and play. Apt bldg has lot's concrete parking but not enough land. The owners do not always pick up after their pets and part of the reason is dog bag stations are not easily accessible, they are quite a distance away. The upside is we have elevators which is helpful for the senior dogs if you live above first floor. The dogs are leashed and owners communicate if their dog if friendly or not. There are parks in driving distance to walk your dig on a leash. Lakes/ parks are clean and dogs love all the smells. Dogs are leashed at the park; its a safe environment."
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  • Arisellmarte5
    "It’s nice I like this spot over here I go to school over here I see a lot people walking their dogs "
    2
    Flag
  • MHB
    "It is truly a great community!! Very safe for children. Friendly neighbors and we have a neighborhood watch set up! The community really looks out for one another. Very happy to live in Maitland."
    0
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  • Salimaharris
    "My commute is by car and in the early afternoon so traffic is pretty light but can be very hectic in the morning. "
    0
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  • Otis5468
    "Quiet and safe, great place to live for young singles and couples, more business types not a lot of kids"
    0
    Flag
  • Otis5468
    "Safe and quiet, nice area, mostly business types, some families , lots of traffic , stores and places to eat"
    0
    Flag
  • Zeus Garca
    "I walk to work 1/2 block every morning. Lake Lilii park is beautiful, safe and a great start to my day"
    1
    Flag
  • Madison S.
    "It’s a great neighborhood for dogs. Sidewalks and neighbors all pick up after animals. Most everyone has a fenced in backyard. "
    1
    Flag
  • Lashana Q.
    "I think the area is secluded and without a car it's hard getting around. I love my place but the gas is ridiculous "
    0
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  • Lydia w.
    "It has a small town feel with modern day amenities. It's quiet and busy at the same time. Neighbors are nice but not intrusive."
    0
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  • Karen M.
    "Lots of dogs walking around but not many sidewalks. Most owners are good about picking up after their pet. "
    0
    Flag
  • Maria M.
    "It’s a great neighborhood. I have the police station close and so far it’s safe. I have quick access to I4."
    1
    Flag
  • Maesojua
    "Excellent community, gated, safe, private, nice neighborhood, love the green and lake view. Close to shops and great restaurants."
    0
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LGBTQ Local Legal Protections

Cece Wong, EXP REALTY LLC, (888) 883-8509
Agent Phone: (407) 809-1440
1065 Gregory Dr, Maitland, FL 32751 is a 3 bedroom, 2 bathroom, 1,929 sqft single-family home built in 1958. This property is currently available for sale and was listed by Stellar MLS on May 28, 2026. The MLS # for this home is MLS# O6411336.