1010 GREGORY DRIVE, Maitland, FL 32751
Property image
Property image
PENDING
3D VIEW
0.28 ACRES

1010 GREGORY DRIVE
Maitland, FL 32751

  • 4 Beds
  • 2 Baths
  • 2,227 sqft (on 0.28 acres)

$520,000

Est. Mortgage $3,638/mo*
Get Pre-Qualified

$520,000

Est. Mortgage $3,638/mo*
Get Pre-Qualified
4 Beds
2 Baths
2,227 sqft
(on 0.28 acres)

Home Highlights

Parking
2 Car Garage
Outdoor
Patio, Pool
Climate Control
Heating & Cooling
HOA
None
Price/Sqft
$233
Listed
61 days ago

Local Information

  • Map ViewExplore the area around 1010 GREGORY DRIVE.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Nestled in the heart of highly desirable Maitland, this spacious 4-bedroom, 2-bath pool home offers the perfect blend of location, functionality, and outdoor living on an oversized .28-acre lot with more than 12,000 square feet of property. Surrounded by mature trees and established neighborhoods, this prime location places you just minutes from Downtown Maitland, Historic Winter Park, Downtown Orlando, world-class shopping, dining, entertainment, and Central Florida’s renowned attractions. Maitland is loved for its charming restaurants, weekend farmer’s market, beautiful lakes, and scenic tree-lined streets, all while bordering some of the most prestigious real estate in Central Florida.The backyard is truly the showstopper of this property, featuring a sparkling open pool, beautiful vinyl fencing, and an expansive yard that is far larger than many homes in the area. Recent landscaping enhancements include a hardscaped entertaining space and decorative stone half wall, creating the perfect setting for relaxing, hosting guests, or enjoying Florida outdoor living under the shade of the beautiful oak tree.Inside, the home features a desirable split-bedroom floor plan with formal living and dining rooms, plus a spacious family room offering plenty of flexibility for everyday living and entertaining. The galley-style kitchen is equipped with granite countertops and overlooks the living areas for easy functionality. Attractive laminate wood flooring and tile flow throughout the home, while all bedrooms have been updated with new ceiling fans. Additional improvements include electrical upgrades, new exterior doors, a new roof installed in 2020, and added attic insulation for enhanced energy efficiency. Built with sturdy concrete block construction, this home offers lasting durability and peace of mind. The indoor laundry room includes the washer and dryer for added convenience. This is a rare opportunity to own a pool home with a large backyard in one of Central Florida’s most established and desirable locations.

Home Details for 1010 GREGORY DRIVE

Interior Features

Interior Details
Number of Rooms: 13Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Primary Bathroom, Bathroom 2, Dinette, Dining Room, Family Room, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2227 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Electricity Connected, Water ConnectedAppliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Electric Dryer Hookup,Inside,Laundry Room,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window TreatmentsDoor: French DoorsFlooring: Engineered Hardwood, Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Engineered Hardwood, Tile
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PatioFencing: FencedVegetation: Mature LandscapingExterior: Irrigation System, Lighting, Sprinkler MeteredFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 18X18No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Door Opener
Pool
Pool: Gunite, In Ground, LightingPool
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: 5Days on Market: 61

Property Information

Year Built
Year Built: 1969
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: BlockNot a New ConstructionNot Attached PropertyNo Additional Parcels
Property Information
Condition: CompletedParcel Number: 2421295070B000020

Price & Status

Price
List Price: $520,000Price Per Sqft: $233
Status Change & Dates
Off Market Date: Mon Jun 01 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: O6411422

Building

Building Area
Building Area: 2671 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 0.28 acres

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6411422Showing Requirements: Appointment Only, ShowingTimeUniversal Property Id: US-12117-N-2421295070000020-R-N
Last check for updates: about 7 hours ago
Listing Provided by: Kelly Hildebrand, (407) 310-5035
FANNIE HILLMAN & ASSOCIATES, (407) 644-1234
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6411422
Also Listed on Stellar MLS.
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 June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$508K
Sale-to-List Price
97.3%
Price per sq ft
$293
Available listings
116
3MoM

Price History for 1010 GREGORY DRIVE

DatePriceEventSource
06/02/2026$520,000PendingStellar MLS #O6411422
05/27/2026$520,000Listed For SaleStellar MLS #O6411422
05/28/2020$350,000Sold
N/A
04/14/2020$350,000PendingAgent Provided
04/01/2020$350,000Listed For SaleAgent Provided
04/18/2016$295,000Sold
Stellar MLS #T2788852
02/29/2016$299,900PendingAgent Provided
02/11/2016$299,900PriceChange
Agent Provided
12/05/2015$314,900PriceChange
Agent Provided
11/14/2015$324,900Listed For SaleAgent Provided
06/15/2015$215,000Sold
Stellar MLS #O5338931
06/10/2015$219,900PendingAgent Provided
06/10/2015$219,900Listed For SaleAgent Provided
12/01/2014$141,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$4,653
Assessment$432,370
Home facts updated by county records

Comparable Sales for 1010 GREGORY DRIVE

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
408 MONTICELLO DRIVE, Altamonte Springs, FL
0.06
Single-Family Home
$503,000
04/15/26
4
2
2,036
407 HERMITAGE DRIVE, Altamonte Springs, FL
0.15
Single-Family Home
$511,000
07/21/26
4
2
2,192
417 MONTICELLO DRIVE, Altamonte Springs, FL
0.14
Single-Family Home
$520,000
08/15/25
4
2
2,077
407 WESTCHESTER DRIVE, Altamonte Springs, FL
0.21
Single-Family Home
$520,000
07/29/25
4
2
2,200
361 HICKORY DRIVE, Maitland, FL
0.18
Single-Family Home
$330,000
06/18/26
3
2
1,407
806 ARLINGTON BOULEVARD, Altamonte Springs, FL
0.25
Single-Family Home
$520,000
06/16/26
4
2
1,917
1004 GREGORY DRIVE, Maitland, FL
0.16
Single-Family Home
$550,000
10/14/25
3
2
1,835
444 STONEWOOD LANE, Maitland, FL
0.22
Single-Family Home
$550,000
10/14/25
3
2
2,188
815 ARLINGTON BOULEVARD, Altamonte Springs, FL
0.22
Single-Family Home
$575,000
06/12/26
3
2
2,055

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Assigned Schools

These are the assigned schools for 1010 GREGORY DRIVE.
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
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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
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  • 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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  • Karen M.
    "Lots of dogs walking around but not many sidewalks. Most owners are good about picking up after their pet. "
    0
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  • 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

Kelly Hildebrand, FANNIE HILLMAN & ASSOCIATES, (407) 644-1234
Agent Phone: (407) 310-5035
1010 GREGORY DRIVE, Maitland, FL 32751 is a 4 bedroom, 2 bathroom, 2,227 sqft single-family home built in 1969. This property is currently available for sale and was listed by Stellar MLS on May 27, 2026. The MLS # for this home is MLS# O6411422.