Skip main navigation
Pending
    • $520,000

    1010 GREGORY DRIVE, MAITLAND, FL 32751

    4beds
    2,227sqft
    : 
    $3,479/mo
    Get pre-qualified
    Single Family Residence
    Built in 1969
    0.28 Acres Lot
    $-- Zestimate®
    $233/sqft
    $-- HOA

    What's special

    Beautiful vinyl fencingDesirable split-bedroom floor planNew exterior doorsDecorative stone half wallSparkling open poolSurrounded by mature treesHardscaped entertaining space
    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.
    63 days
    |
    92
    |
    6
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Kelly Hildebrand 407-310-5035,

    FANNIE HILLMAN & ASSOCIATES 407-644-1234

    Source: Stellar MLS,MLS#: O6411422MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 2
      • Full bathrooms: 2
      Rooms
      • Room types: Dining Room, Living Room, Utility Room
      Primary bedroom
      • Description: Room3
      • Features: En Suite Bathroom, Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 288 Square Feet
      • Dimensions: 18x16
      Bedroom 2
      • Description: Room9
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 10x12
      Bedroom 3
      • Description: Room10
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 10x12
      Bedroom 4
      • Description: Room11
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 110 Square Feet
      • Dimensions: 10x11
      Primary bathroom
      • Description: Room4
      • Features: Shower No Tub, Dual Sinks, Granite Counters, No Closet
      • Level: First
      • Area: 48 Square Feet
      • Dimensions: 16x3
      Bathroom 2
      • Description: Room12
      • Features: Tub With Shower, Dual Sinks, No Closet
      • Level: First
      • Area: 50 Square Feet
      • Dimensions: 10x5
      Dinette
      • Description: Room6
      • Features: Ceiling Fan(s), Built-In Shelving, No Closet
      • Level: First
      • Area: 154 Square Feet
      • Dimensions: 14x11
      Dining room
      • Description: Room2
      • Features: No Closet
      • Level: First
      • Area: 88 Square Feet
      • Dimensions: 11x8
      Family room
      • Description: Room7
      • Features: Ceiling Fan(s), No Closet
      • Level: First
      • Area: 272 Square Feet
      • Dimensions: 17x16
      Kitchen
      • Description: Room5
      • Features: No Closet
      • Level: First
      • Area: 91 Square Feet
      • Dimensions: 13x7
      Laundry
      • Description: Room13
      • Features: No Closet
      • Level: First
      • Area: 70 Square Feet
      • Dimensions: 10x7
      Laundry
      • Description: Room8
      • Features: No Closet
      • Level: First
      • Area: 70 Square Feet
      • Dimensions: 10x7
      Living room
      • Description: Room1
      • Features: Ceiling Fan(s), No Closet
      • Level: First
      • Area: 294 Square Feet
      • Dimensions: 21x14
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Wine Refrigerator
      • Laundry: Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
      Features
      • Built-in Features, Ceiling Fan(s), Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat
      • Flooring: Engineered Hardwood, Tile
      • Doors: French Doors
      • Windows: Window Treatments
      • Has fireplace: No
      Interior area
      • Total structure area: 2,671
      • Total interior livable area: 2,227 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage Door Opener
      • Attached garage spaces: 2
      • Details: Garage Dimensions: 18X18
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Patio
      • Exterior features: Irrigation System, Lighting, Sprinkler Metered
      • Has private pool: Yes
      • Pool features: Gunite, In Ground, Lighting
      • Fencing: Fenced
      Lot
      • Size: 0.28 Acres
      • Dimensions: 105 x 117
      • Features: Cleared, In County, Level
      • Residential vegetation: Mature Landscaping
      Details
      • Parcel number: 2421295070B000020
      • Zoning: R-1AA
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Ranch
      • Property subtype: Single Family Residence
      Materials
      • Block
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • Completed
      • New construction: No
      • Year built: 1969

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: BB/HS Internet Available, Electricity Connected, Water Connected

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: DRUID HILLS ESTATES 1ST ADD
      HOA
      • Has HOA: No
      Location
      • Region: Maitland

      Financial & listing details

      • Price per square foot: $233/sqft
      • Tax assessed value: $432,370
      • Annual tax amount: $4,288
      • Date on market: 5/27/2026
      • Cumulative days on market: 63 days
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/2/2026Pending sale$520,000$233/sqft
        Source: Stellar MLS #O6411422 Report a problem
        5/27/2026Listed for sale$520,000+48.6%$233/sqft
        Source: Stellar MLS #O6411422 Report a problem
        5/28/2020Sold$350,000$157/sqft
        Source: Public Record Report a problem
        4/14/2020Pending sale$350,000$157/sqft
        Source: RE/MAX TOWN & COUNTRY REALTY #O5852509 Report a problem
        4/1/2020Listed for sale$350,000+18.6%$157/sqft
        Source: RE/MAX TOWN & COUNTRY REALTY #O5852509 Report a problem
        4/18/2016Sold$295,000-1.6%$132/sqft
        Source: Stellar MLS #T2788852 Report a problem
        2/29/2016Pending sale$299,900$135/sqft
        Source: ADDvantage Real Estate #T2788852 Report a problem
        2/11/2016Price change$299,900-4.8%$135/sqft
        Source: ADDvantage Real Estate #T2788852 Report a problem
        12/5/2015Price change$314,900-3.1%$141/sqft
        Source: ADDvantage Real Estate #T2788852 Report a problem
        11/14/2015Listed for sale$324,900+51.1%$146/sqft
        Source: ADDvantage Real Estate #T2788852 Report a problem
        6/15/2015Sold$215,000-2.2%$97/sqft
        Source: Stellar MLS #O5338931 Report a problem
        6/10/2015Pending sale$219,900$99/sqft
        Source: RT CAPITAL INVESTING LLC #O5338931 Report a problem
        6/10/2015Listed for sale$219,900+56%$99/sqft
        Source: RT CAPITAL INVESTING LLC #O5338931 Report a problem
        12/1/2014Sold$141,000$63/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,653 +15.7%$354,310 +2.9%
        2024$4,020 +2.6%$344,325 +3%
        2023$3,918 +2.6%$334,296 +3%
        2022$3,818 -6.4%$324,559 +3%
        2021$4,078 +25%$315,106 +23.8%
        2020$3,263 +1%$254,469 +2.3%
        2019$3,231 $248,748 +1.9%
        2018$3,231 +1%$244,110 +2.1%
        2017$3,197 +0.6%$239,089 +4.8%
        2016$3,178 -11.7%$228,089 +28%
        2015$3,598 $178,195 +5.4%
        2014$3,598 +113.4%$169,119 +18%
        2013$1,686 +7.4%$143,270 +1.7%
        2012$1,570 +2.9%$140,875 +3%
        2011$1,526 +1%$136,772 +1.5%
        2010$1,510 +4.4%$134,751 +2.7%
        2009$1,446 +3.7%$131,208 +0.1%
        2008$1,395 -6.7%$131,077 +3%
        2007$1,495 -5.5%$127,259 +2.5%
        2006$1,582 +2.1%$124,155 +3%
        2005$1,549 +0.7%$120,539 +3%
        2004$1,538 +1%$117,028 +1.9%
        2003$1,523 +0.9%$114,846 +2.4%
        2002$1,510 +3.9%$112,154 +4.6%
        2000$1,453 $107,173
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.
        Get pre-qualified

        Climate risks

        Neighborhood: 32751

        Getting around

        7 / 100
        Car-Dependent
        35 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Lake Orienta Elementary
        • Middle: Milwee Middle
        • High: Lyman High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

        A local agent can set up tours, give advice and negotiate with sellers.

        A local lender can help you make sure your offer is ready when you are.

        Browse local experts

        Similar homes

            Nearby cities

            Nearby zip codes

            Other Maitland Topics

              Search
              Updates
              Favorites
              Plan
              Inbox