1004 Gregory Dr, Maitland, FL 32751
SOLD
OCT 14, 2025

1004 Gregory Dr
Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,835 sqft (on 0.31 acres)

$550,000

Last Sold: Oct 14, 2025
2% below list $559K
$300/sqft
Est. Refi. Payment $3,806/mo*
Refinance Your Home

$550,000

Last Sold: Oct 14, 2025
2% below list $559K
$300/sqft
Est. Refi. Payment $3,806/mo*
Refinance Your Home
3 Beds
2 Baths
1,835 sqft
(on 0.31 acres)

Local Information

  • Map ViewExplore the area around 1004 Gregory Dr.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Immaculate three bedroom, two bathroom home located in the highly desirable Druid Hills neighborhood. This home boasts warmth and charm. Impeccably designed, this home offers the farmhouse style you have been searching for. From the custom kitchen cabinetry to the roof, no detail has been left unattended. Upon entering through the front door you are immediately immersed by the charm of this home. The centerpiece, the kitchen, opens itself to all living areas of the home. The kitchen features custom concrete countertops, classic farmhouse sink, gas range (propane), dual pantries, custom solid wood cabinetry accompanied by upgraded appliances that blend perfectly into the cabinetry setting, all brought together by a vast 9 foot center island featuring a custom made butcher block counter top. Lying just off the kitchen is a cozy, yet elegant dining room accompanied by a quaint dry bar with a beautiful cedar board backdrop. Venturing down the hallway, extended from the main living areas, rests the master suite. Featuring vinyl flooring, the master suite offers a peaceful retreat. The home features a mudroom, including washer and dryer connections and a custom built shoe cubby and coat rack. Some of the newer updates include Low-E Windows 2021, new AC and Ductwork 2022, new Electric Hot Water Heater 2022, a new Vinyl Fence 2022, and new Roof 2024. Enjoy the peaceful sights and sounds of the majestic live oaks that surround this beautiful home, while relaxing on the back patio. Convenience cannot be overstated, located within close proximity and access to Downtown Maitland, I-4 (with quick access to I-4 Express West Bound), superb Seminole County schools, and many local restaurants and establishments.
1004 Gregory Dr, Maitland, FL 32751 is a 3 bedroom, 2 bathroom, 1,835 sqft single-family home built in 1959. It last sold for $550,000 on Oct 14, 2025 (2% below the $559,000 asking price). It is currently off market. The Trulia Estimate is $540,500, with a rent estimate of $2,595/month.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch
View
No Info
HOA
None
Price/Sqft
$300/sqft
Listed
180+ days ago

Home Details for 1004 Gregory Dr

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dining Room, Kitchen, Laundry, Living Room, Office
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1835 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Fiber Optics, PropaneAppliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer, Wine RefrigeratorDishwasherDryerLaundry: InsideMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family Room, Wood BurningHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Low Emissivity WindowsDoor: French DoorsFlooring: Laminate, Vinyl
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Laminate, Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Rear PorchFencing: VinylVegetation: Oak Trees, Trees/LandscapedExterior: LightingFoundation: CrawlspaceNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 22x25No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener,Garage Faces Rear
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 57

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Block, BrickNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 2421295070A000100

Price & Status

Price
List Price: $559,000Price Per Sqft: $300/sqft
Status Change & Dates
Off Market Date: Sun Sep 14 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

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: 2529 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.31 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6328342Back On Market Date: Tue Aug 26 2025Showing Requirements: Appointment Only, Call Listing AgentUniversal Property Id: US-12117-N-2421295070000100-R-N
Last check for updates: about 3 hours ago
Listed by Nicholas Giovanetti, (321) 239-7622
KELLY PRICE & COMPANY LLC, (407) 645-4321
Bought with: Kemper Turner, CHARLES RUTENBERG REALTY ORLANDO, (407) 622-2122
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6328342
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

Price History for 1004 Gregory Dr

DatePriceEventSource
10/14/2025$550,000Sold
Stellar MLS #O6328342
09/16/2025$559,000PendingStellar MLS #O6328342
08/26/2025$559,000PendingToActiveStellar MLS #O6328342
08/26/2025$559,000PendingStellar MLS #O6328342
08/25/2025$559,000PriceChange
Stellar MLS #O6328342
08/12/2025$565,000PriceChange
Stellar MLS #O6328342
08/04/2025$579,900PriceChange
Stellar MLS #O6328342
07/28/2025$599,900PriceChange
Stellar MLS #O6328342
07/23/2025$624,000PriceChange
Stellar MLS #O6328342
07/18/2025$639,000Listed For SaleStellar MLS #O6328342
09/06/2019$325,000Sold
N/A
06/14/2019$325,000PendingToActiveAgent Provided
06/14/2019$325,000PendingAgent Provided
05/23/2019$325,000Listed For SaleAgent Provided

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
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Property Tax and Assessment

Year2025
Tax$3,569
Assessment$382,289
Home facts updated by county records

Comparable Sales for 1004 Gregory Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
444 Stonewood Ln, Maitland, FL
0.15
Single-Family Home
$550,000
10/14/25
3
2
2,188
408 Monticello Dr, Altamonte Springs, FL
0.22
Single-Family Home
$503,000
04/15/26
4
2
2,036
344 Banyan Dr, Maitland, FL
0.25
Single-Family Home
$398,000
05/15/26
3
2
1,408
815 Arlington Blvd, Altamonte Springs, FL
0.36
Single-Family Home
$575,000
06/12/26
3
2
2,055
417 Monticello Dr, Altamonte Springs, FL
0.28
Single-Family Home
$520,000
08/15/25
4
2
2,077
361 Hickory Dr, Maitland, FL
0.20
Single-Family Home
$330,000
06/18/26
3
2
1,407
363 Croton Dr, Maitland, FL
0.13
Single-Family Home
$350,000
11/24/25
3
2
1,386
380 Banyan Dr, Maitland, FL
0.18
Single-Family Home
$400,000
01/16/26
3
2
1,404

Nearby homes

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Assigned Schools

These are the assigned schools for 1004 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 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

  • 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.
  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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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
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Homes for sale near 1004 Gregory Dr

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Off Market Homes Near 1004 Gregory Dr

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