Skip main navigation
Pending
    • $519,000

    1065 GREGORY DR, MAITLAND, FL 32751

    3beds
    1,929sqft
    : 
    $3,437/mo
    Get pre-qualified
    Single Family Residence
    Built in 1958
    0.28 Acres Lot
    $511,100 Zestimate®
    $269/sqft
    $-- HOA

    What's special

    Cozy fireplaceStorage shedWhite vinyl fenceScreen enclosureHardwood floorsSplit bedroom floor planOversized rectangular pool
    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!
    60 days
    |
    450
    |
    34
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Cece Wong 407-809-1440,

    EXP REALTY LLC 888-883-8509

    Source: Stellar MLS,MLS#: O6411336MLS LogoOriginating MLS: Sarasota - Manatee

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Rooms
      • Room types: Bonus Room
      Primary bedroom
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: First
      • Area: 156 Square Feet
      • Dimensions: 13x12
      Bedroom 2
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 132 Square Feet
      • Dimensions: 11x12
      Bedroom 3
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 132 Square Feet
      • Dimensions: 11x12
      Primary bathroom
      • Features: Shower No Tub, Single Vanity
      • Level: First
      • Area: 32 Square Feet
      • Dimensions: 8x4
      Bathroom 2
      • Features: Tub With Shower
      • Level: First
      • Area: 35 Square Feet
      • Dimensions: 5x7
      Balcony porch lanai
      • Level: First
      • Dimensions: 10x23
      Bonus room
      • Features: Ceiling Fan(s), No Closet
      • Level: First
      • Area: 361 Square Feet
      • Dimensions: 19x19
      Dining room
      • Level: First
      • Area: 110 Square Feet
      • Dimensions: 10x11
      Family room
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 180 Square Feet
      • Dimensions: 12x15
      Kitchen
      • Features: Pantry
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 12x10
      Living room
      • Level: First
      • Area: 300 Square Feet
      • Dimensions: 15x20
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
      • Laundry: In Garage, Laundry Room
      Features
      • Ceiling Fan(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat
      • Flooring: Tile, Hardwood
      • Doors: French Doors
      • Has fireplace: Yes
      • Fireplace features: Living Room, Wood Burning
      Interior area
      • Total structure area: 2,609
      • Total interior livable area: 1,929 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Driveway
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Enclosed, Front Porch, Patio, Porch, Rear Porch, Screened
      • Exterior features: Irrigation System, Storage
      • Has private pool: Yes
      • Pool features: In Ground, Screen Enclosure
      • Fencing: Vinyl
      Lot
      • Size: 0.28 Acres
      • Residential vegetation: Mature Landscaping
      Details
      • Additional structures: Shed(s), Storage
      • Parcel number: 2421295070A000120
      • Zoning: R-1AA
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Florida,Ranch
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Crawlspace
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1958

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Public

      Community & HOA

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

      Financial & listing details

      • Price per square foot: $269/sqft
      • Tax assessed value: $416,920
      • Annual tax amount: $5,684
      • Date on market: 5/28/2026
      • Cumulative days on market: 50 days
      • Listing terms: Cash,Conventional,FHA
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Road surface type: Paved, Asphalt

        Estimated market value

        $511,100

        $486,000 - $537,000

        $3,358/mo

        Price history

        DateEventPrice
        7/10/2026Pending sale$519,000$269/sqft
        Source: eXp Realty #O6411336 Report a problem
        6/22/2026Listed for sale$519,000$269/sqft
        Source: eXp Realty #O6411336 Report a problem
        6/12/2026Pending sale$519,000$269/sqft
        Source: eXp Realty #O6411336 Report a problem
        5/28/2026Listed for sale$519,000+22.1%$269/sqft
        Source: Stellar MLS #O6411336 Report a problem
        11/11/2024Listing removed$425,000-4.5%$220/sqft
        Source: Stellar MLS #O5975285 Report a problem
        11/11/2023Listing removed--
        Source: Stellar MLS #O5975285 Report a problem
        11/17/2021Sold$445,000+4.7%$231/sqft
        Source: Public Record Report a problem
        9/27/2021Pending sale$425,000$220/sqft
        Source: Stellar MLS #O5975285 Report a problem
        9/24/2021Listed for sale$425,000+49.1%$220/sqft
        Source: Stellar MLS #O5975285 Report a problem
        3/16/2018Sold$285,000$148/sqft
        Source: Public Record Report a problem
        2/9/2018Pending sale$285,000$148/sqft
        Source: KELLER WILLIAMS HERITAGE REALTY #O5560686 Report a problem
        2/8/2018Listed for sale$285,000+8.6%$148/sqft
        Source: KELLER WILLIAMS HERITAGE REALTY #O5560686 Report a problem
        7/8/2016Sold$262,500$136/sqft
        Source: Stellar MLS #O5395746 Report a problem
        6/24/2016Pending sale$262,500$136/sqft
        Source: KELLY PRICE & COMPANY LLC #O5395746 Report a problem
        6/3/2016Price change$262,500-9%$136/sqft
        Source: KELLY PRICE & COMPANY LLC #O5395746 Report a problem
        2/3/2016Price change$288,500-3.4%$150/sqft
        Source: KELLY PRICE & COMPANY LLC #O5395746 Report a problem
        10/26/2015Price change$298,500-8.2%$155/sqft
        Source: KELLY PRICE & COMPANY LLC #O5395746 Report a problem
        10/2/2015Listed for sale$325,000+132.5%$168/sqft
        Source: KELLY PRICE & COMPANY LLC #O5395746 Report a problem
        5/3/1999Sold$139,800+47.2%$72/sqft
        Source: Public Record Report a problem
        11/13/1995Sold$95,000$49/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$6,068 +11.8%$416,920 +1.5%
        2024$5,425 +7.4%$410,724 +8.2%
        2023$5,050 +7.7%$379,470 +8.5%
        2022$4,688 +48.3%$349,622 +40.6%
        2021$3,162 +0.8%$248,722 +1.4%
        2020$3,135 +1%$245,288 +2.3%
        2019$3,104 $239,773 +93.1%
        2018$3,104 +109.7%$124,198 +2.1%
        2017$1,480 +1.1%$121,643 -20%
        2016$1,465 -41.5%$152,104 +17.1%
        2015$2,505 $129,898 +0.8%
        2014$2,505 +73.9%$128,867 +1.5%
        2013$1,441 +7.6%$126,963 +1.7%
        2012$1,339 +3%$124,841 +3%
        2011$1,300 +1.1%$121,205 +1.5%
        2010$1,285 +4.6%$119,414 +2.7%
        2009$1,229 +3.7%$116,275 +0.1%
        2008$1,185 -8.6%$116,159 +3%
        2007$1,296 -5.4%$112,776 +2.5%
        2006$1,370 +2.2%$110,025 +3%
        2005$1,341 +0.8%$106,820 +3%
        2004$1,330 +1.1%$103,709 +1.9%
        2003$1,316 +1.5%$101,775 +2.4%
        2002$1,296 +4.8%$99,390 +4.6%
        2000$1,237 $94,976
        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

        10 / 100
        Car-Dependent
        32 / 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