1065 GREGORY DR, Maitland, FL 32751
SOLD
AUG 7, 2026

$509,500

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

1065 GREGORY DR, Maitland, FL 32751

Est. Refi. Payment $3,582/mo*
Refinance Your Home
Currently Off Market - Sold Aug 7, 2026 for $510,000 (2% below list price)

Home Value

Trulia Estimate
$510K
Since last month
Decreased$2K (-0.5%)
Since last year
Decreased$5K (-0.9%)
Since last sale
Decreased$500 (-0.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +90% in the last 10 years
MonthEstimated value
2026
August 2026$510K
July 2026$512K
June 2026$513K
May 2026$521K
April 2026$507K
March 2026$509K
February 2026$509K
January 2026$509K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1004 GREGORY DRIVE, Maitland, FL
0.04
Single-Family Home
$550,000
10/14/25
3
2
1,835
1010 GREGORY DRIVE, Maitland, FL
0.12
Single-Family Home
$515,000
08/03/26
4
2
2,227
444 STONEWOOD LANE, Maitland, FL
0.17
Single-Family Home
$550,000
10/14/25
3
2
2,188
408 MONTICELLO DRIVE, Altamonte Springs, FL
0.18
Single-Family Home
$503,000
04/15/26
4
2
2,036
815 ARLINGTON BOULEVARD, Altamonte Springs, FL
0.32
Single-Family Home
$575,000
06/12/26
3
2
2,055
407 HERMITAGE DRIVE, Altamonte Springs, FL
0.26
Single-Family Home
$511,000
07/21/26
4
2
2,192
344 BANYAN DRIVE, Maitland, FL
0.22
Single-Family Home
$398,000
05/15/26
3
2
1,408
361 HICKORY DRIVE, Maitland, FL
0.17
Single-Family Home
$330,000
06/18/26
3
2
1,407

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1030 GREGORY DRIVE, Maitland, FL 32751
0.07
$516,000
5
2.5
2,289
Off Market
1004 GREGORY DRIVE, Maitland, FL 32751
0.04
$542,500
3
2
1,835
Off Market
395 SULTANA LANE, Maitland, FL 32751
0.06
$262,400
3
2
1,344
Off Market
986 STONEWOOD LANE, Maitland, FL 32751
0.12
$727,000
4
2.5
2,195
Off Market
1010 GREGORY DRIVE, Maitland, FL 32751
0.12
$515,000
4
2
2,227
Recently Sold
911 ORANOLE ROAD, Maitland, FL 32751
0.10
$404,100
3
2
1,784
Off Market
987 STONEWOOD LANE, Maitland, FL 32751
0.14
$553,400
3
2
1,935
Off Market
1202 ORANOLE ROAD, Maitland, FL 32751
0.08
$412,800
3
2
1,750
For Sale
382 SULTANA LANE, Maitland, FL 32751
0.09
$385,200
3
2
1,279
Off Market
408 MONTICELLO DRIVE, Altamonte Springs, FL 32701
0.18
$503,000
4
2
2,036
Recently Sold
380 BANYAN DRIVE, Maitland, FL 32751
0.15
$400,000
3
2
1,404
Recently Sold

Local Information

  • Map ViewExplore the area around 1065 GREGORY DR.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1958
0.28 acre lot
1,929 sqft
$264/sqft
2 Car Garage

About this House

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!
1065 GREGORY DR, Maitland, FL 32751 is a 3 bedroom, 2 bathroom, 1,929 sqft single-family home built in 1958. It last sold for $510,000 on Aug 7, 2026 (2% below the $519,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $509,500, with a rent estimate of $3,226/month.
Last check for updates: about 23 hours ago
Listed by Cece Wong, (407) 809-1440
EXP REALTY LLC, (888) 883-8509
Bought with: Barrett Spray, (407) 927-3650, KELLER WILLIAMS ADVANTAGE REALTY, (407) 977-7600
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#O6411336
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

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
Door: 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: 32

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: $264/sqft
Status Change & Dates
Off Market Date: Fri Jul 10 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

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

Building

Building Area
Building Area: 2609 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Sarasota - ManateeNo HOA

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: O6411336Back On Market Date: Mon Jun 22 2026Showing Considerations: See RemarksShowing Requirements: Appointment Only, Lockbox - Electronic, See Remarks, ShowingTimeUniversal Property Id: US-12117-N-2421295070000120-R-N

Price and Tax history

DateEventPrice
Aug 7, 2026
Source: Stellar MLS #O6411336
Sold
$510,000
Jul 10, 2026
Source: eXp Realty #O6411336
Pending
$519,000
Jun 22, 2026
Source: eXp Realty #O6411336
PendingToActive
$519,000
Jun 12, 2026
Source: eXp Realty #O6411336
Pending
$519,000
May 28, 2026
Source: Stellar MLS #O6411336
Listed For Sale
$519,000

Market trends in Maitland

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$511K
$2.33KMoM
Sale-to-List Price
—
Price per sq ft
$305
$12MoM
Available listings
120
3MoM

Around this home

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 170 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

  • 67 % 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

  • 49 % 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.
  • Che F
    "We have great neighborhood events but day to day is quiet and peaceful."
    0
    Flag
  • Monica.maeda.mhc
    "Many people take care of their property, there are many parks and shops that are walking distant, and it is quiet"
    0
    Flag
  • 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
    Flag
  • 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."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 1065 GREGORY DR

  • What is 1065 GREGORY DR estimated to be worth?
    Trulia's estimated value for 1065 GREGORY DR in Maitland, FL is $509,500.
  • What is the price history for 1065 GREGORY DR?
    1065 GREGORY DR in Maitland, FL last sold for $510,000 in August 2026.
  • What are the closest schools to 1065 GREGORY DR?
    The closest schools to 1065 GREGORY DR in Maitland, FL are Lake Orienta Elementary School (Pre-K, rated 3/10), Lyman High School (Pre-K, rated 6/10), Milwee Middle School (rated 6/10).
  • Does 1065 GREGORY DR have air conditioning?
    Yes, 1065 GREGORY DR in Maitland, FL has air conditioning.
  • Does 1065 GREGORY DR have a pool?
    Yes, 1065 GREGORY DR in Maitland, FL has a pool.
  • Does 1065 GREGORY DR have laundry facilities?
    Yes, 1065 GREGORY DR in Maitland, FL has in-unit laundry.

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