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Under contract
    • $495,000

    14126 Winterset Dr, Orlando, FL 32832

    3beds
    1,960sqft
    : 
    $3,278/mo
    Get pre-qualified
    Single Family Residence
    Built in 1985
    0.33 Acres Lot
    $-- Zestimate®
    $253/sqft
    $-- HOA

    What's special

    Under contract-accepting backup offers. Rare opportunity to own an authentic log home in the heart of Isle of Pines! Combining timeless rustic charm with thoughtful modern updates, this beautifully maintained 3-bedroom, 2-bath retreat offers the perfect blend of rustic character and modern updates. This one-of-a-kind home feels like a peaceful country retreat while remaining just a short drive from Lake Nona, SR 417, shopping, dining, and Orlando International Airport. Step inside to find an updated kitchen with a large island that's perfect for gathering with family and friends, new appliances (2024), beautifully updated bathrooms, and wood and tile flooring throughout. Cozy up beside the wood-burning fireplace on cooler evenings or enjoy the abundance of natural light streaming through all-new windows. Major improvements include a roof (2024) and A/C (2023) H2O system (2023), Water Heater (2025). Outside, the lifestyle continues with a screened-in pool, a spacious front porch that's perfect for morning coffee while watching the local wildlife, including baby deer that visit often!, and a fully fenced side yard just off the kitchen that's ideal for dogs or little ones to play safely. Need room for your hobbies, toys, or future plans? In addition to the detached two-car garage, you'll find a second detached building currently housing three vehicles, it's ready to become a workshop, studio, home gym, additional storage, or potentially an accessory dwelling unit. This home is served by well and septic, offering lower monthly utility costs, and residents have the option to join the voluntary Isle of Pines Property Owners Association. For a small annual fee you can enjoy access to Lake Mary Jane with a private boat ramp and dock, community events, playground, trails, and more. If you've been dreaming of a home with character, privacy, room to spread out, and a little piece of Old Florida charm, this is one you won't want to miss.
    14 days
    |
    520
    |
    34
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Kerry Stafford 407-821-8600,

    CHARLES RUTENBERG REALTY ORLANDO 407-622-2122

    Source: Stellar MLS,MLS#: O6423922MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Rooms
      • Room types: Attic, Storage Rooms
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      Bedroom 2
      • Features: Built-in Closet
      • Level: First
      Bedroom 3
      • Features: Built-in Closet
      • Level: First
      Dining room
      • Level: First
      Kitchen
      • Level: First
      Living room
      • Level: First
      Workshop
      • Level: First
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Water Filtration System
      • Laundry: Inside, Laundry Room
      Features
      • Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)
      • Flooring: Ceramic Tile, Hardwood
      • Doors: Sliding Doors
      • Windows: Window Treatments
      • Has fireplace: Yes
      • Fireplace features: Living Room, Masonry, Wood Burning
      Interior area
      • Total structure area: 3,220
      • Total interior livable area: 1,960 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 5
      • Parking features: Boat, Driveway, Garage Door Opener, RV Access/Parking, Split Garage
      • Garage spaces: 5
      • Has uncovered spaces: Yes
      Features
      • Levels: One
      • Stories: 1
      • Exterior features: Dog Run, Other, Rain Gutters, Storage
      • Has private pool: Yes
      • Pool features: Gunite, Heated, In Ground, Screen Enclosure
      • On waterfront: Yes
      • Waterfront features: Lake, Waterfront, Beach Access, Lake Privileges, Private Lake Dues Required, Skiing Allowed
      • Body of water: LAKE MARY JANE
      Lot
      • Size: 0.33 Acres
      • Residential vegetation: Mature Landscaping, Oak Trees
      Details
      • Additional structures: Storage, Workshop
      • Parcel number: 252431388203090
      • Zoning: R-1A
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Log
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1985

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cable Available, Electricity Connected, Private

      Community & HOA

      Community
      • Features: Community Boat Ramp, Dock, Fishing, Lake, Private Boat Ramp, Water Access, Waterfront, Park, Playground
      • Pet fee: $0 monthly
      • Subdivision: ISLE OF PINES FIFTH ADD
      HOA
      • Has HOA: No
      • Amenities included: Optional Additional Fees, Park, Playground, Recreation Facilities, Trail(s)
      Location
      • Region: Orlando

      Financial & listing details

      • Price per square foot: $253/sqft
      • Tax assessed value: $438,044
      • Annual tax amount: $4,413
      • Date on market: 7/9/2026
      • Cumulative days on market: 13 days
      • Listing terms: Cash,Conventional,FHA,USDA Loan,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt, Gravel

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/11/2026Contingent$495,000$253/sqft
        Source: Stellar MLS #O6423922 Report a problem
        7/9/2026Listed for sale$495,000+45.6%$253/sqft
        Source: Stellar MLS #O6423922 Report a problem
        12/30/2020Sold$340,000-2.6%$173/sqft
        Source: DBAMLS #1068574 Report a problem
        11/4/2020Listed for sale$349,000$178/sqft
        Source: Coldwell Banker Coast Realty #1068574 Report a problem
        10/2/2020Listing removed$349,000$178/sqft
        Source: Coldwell Banker Coast Realty #1068574 Report a problem
        9/18/2020Price change$349,000-3.1%$178/sqft
        Source: Coldwell Banker Coast Realty #1068574 Report a problem
        7/10/2020Price change$360,000-4%$184/sqft
        Source: Coldwell Banker Coast Realty #1068574 Report a problem
        3/2/2020Listed for sale$375,000+1667.7%$191/sqft
        Source: Coldwell Banker Coast Realty #1068574 Report a problem
        12/31/2008Sold$21,214-88.2%$11/sqft
        Source: Public Record Report a problem
        4/29/2004Sold$180,000+71.4%$92/sqft
        Source: Public Record Report a problem
        1/19/2000Sold$105,000$54/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$4,190 +7.4%$285,857 +3%
        2023$3,902 +2%$277,531 +3%
        2022$3,826 -21.1%$269,448 -7.1%
        2021$4,849 +87.3%$290,132 +56%
        2020$2,589 +1.6%$185,925 +2.3%
        2019$2,548 +1%$181,745 +1.9%
        2018$2,524 0%$178,356 -18.9%
        2017$2,524 +1.7%$219,805 +2%
        2016$2,481 +1.1%$215,412 +8.3%
        2015$2,454 -3.7%$198,889 -2.4%
        2014$2,547 +2.3%$203,841 +22.5%
        2013$2,490 +1.3%$166,442 +1.9%
        2012$2,459 -3.2%$163,291 -2.4%
        2011$2,541 -9%$167,268 -10%
        2010$2,793 $185,845 -4.7%
        2009-- $195,089 -14.6%
        2008$3,169 -2.1%$228,347 -14.1%
        2007$3,237 +24%$265,854 +2.6%
        2006$2,610 +0.9%$259,031 +67.4%
        2005$2,588 +75.7%$154,762 +33.1%
        2004$1,473 +0.8%$116,303 +16.2%
        2003$1,462 +3%$100,071 +3.5%
        2002$1,419 -0.6%$96,715 +6.3%
        2001$1,428 -17.2%$90,948 +13.4%
        2000$1,726 $80,230
        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.
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        Climate risks

        Neighborhood: 32832

        Getting around

        12 / 100
        Car-Dependent
        0 / 100
        No Nearby Transit
        27 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Moss Park Elementary
        • Middle: Innovation Middle School
        • High: Innovation High

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

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