1075 Gregory Dr, Maitland, FL 32751
OFF MARKET

$514,000

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,031 sqft (on 0.28 acres)

1075 Gregory Dr, Maitland, FL 32751

Est. Refi. Payment $3,643/mo*
Refinance Your Home
Currently Off Market - Sold Jan 17, 2014 for $250,000

Home Value

Trulia Estimate
$514K
Since last month
Decreased$2K (-0.4%)
Since last year
Decreased$16K (-3.1%)
Since last sale
Increased$265K (+105.8%)
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 +71% in the last 10 years
MonthEstimated value
2026
August 2026$515K
August 2026$514K
July 2026$517K
June 2026$520K
May 2026$525K
April 2026$521K
March 2026$523K
February 2026$524K
January 2026$522K
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
1065 GREGORY DR, Maitland, FL
0.02
Single-Family Home
$510,000
08/07/26
3
2
1,929
1004 GREGORY DRIVE, Maitland, FL
0.02
Single-Family Home
$550,000
10/14/25
3
2
1,835
361 HICKORY DRIVE, Maitland, FL
0.18
Single-Family Home
$330,000
06/18/26
3
2
1,407
1606 Oranole Rd, Maitland, FL
0.25
Single-Family Home
$376,000
05/12/26
3
2
1,951
444 STONEWOOD LANE, Maitland, FL
0.16
Single-Family Home
$550,000
10/14/25
3
2
2,188
363 CROTON DRIVE, Maitland, FL
0.13
Single-Family Home
$350,000
11/24/25
3
2
1,386
1010 GREGORY DRIVE, Maitland, FL
0.14
Single-Family Home
$515,000
08/03/26
4
2
2,227
344 BANYAN DRIVE, Maitland, FL
0.23
Single-Family Home
$398,000
05/15/26
3
2
1,408
408 MONTICELLO DRIVE, Altamonte Springs, FL
0.20
Single-Family Home
$503,000
04/15/26
4
2
2,036
370 SULTANA LANE, Maitland, FL
0.12
Single-Family Home
$370,000
03/12/26
3
2
1,683

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
1004 GREGORY DRIVE, Maitland, FL 32751
0.02
$542,500
3
2
1,835
Off Market
1065 GREGORY DR, Maitland, FL 32751
0.02
$510,000
3
2
1,929
Recently Sold
1202 ORANOLE ROAD, Maitland, FL 32751
0.06
$412,800
3
2
1,750
For Sale
1120 DRUID ROAD, Maitland, FL 32751
0.12
$581,500
4
3
1,962
Off Market
395 SULTANA LANE, Maitland, FL 32751
0.07
$262,400
3
2
1,344
Off Market
1030 GREGORY DRIVE, Maitland, FL 32751
0.09
$516,000
5
2.5
2,289
Off Market
382 SULTANA LANE, Maitland, FL 32751
0.09
$385,200
3
2
1,279
Off Market
986 STONEWOOD LANE, Maitland, FL 32751
0.13
$727,000
4
2.5
2,195
Off Market
444 STONEWOOD LANE, Maitland, FL 32751
0.16
$542,500
3
2
2,188
Off Market
1225 ORANOLE ROAD, Maitland, FL 32751
0.12
$533,500
4
2.5
2,240
Off Market
987 STONEWOOD LANE, Maitland, FL 32751
0.15
$553,400
3
2
1,935
Off Market
1024 DRUID ROAD, Maitland, FL 32751
0.17
$912,800
3
2
2,200
Off Market

Local Information

  • Map ViewExplore the area around 1075 Gregory Dr.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1975
Lot Size
0.28 acres
Living Area
2,031 sqft
Price/Sqft
$253
Parking
Garage

About this House

Beautiful, totally remodeled Maitland home on large fenced lot ! Light and bright, wood floors, travertine, fireplace, large eat-in kitchen with custom cabinets and skylights. California Closets built ins with large built in desk area. Stylish light and plumbing fixtures. Sunroom/Bonus room with French doors leading to screened patio with slate flooring. Remodeled baths with travertine shower and oil rubbed bronze fixtures. Large, fenced landscaped lot with side entry driveway. Beautifully landscaped with mature trees and well maintained lawn. Move-in ready !!
1075 Gregory Dr, Maitland, FL 32751 is a 3 bedroom, 2 bathroom, 2,031 sqft single-family home built in 1975. It last sold for $250,000 on Jan 17, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $514,000, with a rent estimate of $2,481/month.

Home Details for 1075 Gregory Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Interior Details
Types of Rooms: Walk In Closet, Dining Room, Family Room, Master Bath, OfficeCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Stucco, Brick, Cement ConcreteFoundation Type: FootingLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 4Parking: Carport, Garage Attached, Off Street

Property Information

Year Built
Year Built: 1975Year Updated: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
Jan 17, 2014
Source: Stellar MLS #O5196534
Sold
$250,000
Nov 27, 2013
Source: Agent Provided
Listed For Sale
$264,900
Dec 31, 1996
Source: N/A
Sold
$106,000

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 1075 Gregory Dr

  • What is 1075 Gregory Dr estimated to be worth?
    Trulia's estimated value for 1075 Gregory Dr in Maitland, FL is $514,000.
  • What is the price history for 1075 Gregory Dr?
    1075 Gregory Dr in Maitland, FL last sold for $250,000 in January 2014.
  • What are the closest schools to 1075 Gregory Dr?
    The closest schools to 1075 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 1075 Gregory Dr have air conditioning?
    Yes, 1075 Gregory Dr in Maitland, FL has air conditioning.
  • How big is the lot at 1075 Gregory Dr?
    The lot at 1075 Gregory Dr in Maitland, FL is about 0.28 acres (12,371 sq ft).
  • Does 1075 Gregory Dr have a garage?
    Yes, 1075 Gregory Dr in Maitland, FL has a garage.

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Off Market Homes Near 1075 Gregory Dr

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