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Active under contract
    • Price cut: $25K (6/12)
    $849,900

    23 Pennywhistle Drive, Windham, ME 04062

    3beds
    2,856sqft
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    Single Family Residence
    Built in 2022
    1.03 Acres Lot
    $848,200 Zestimate®
    $298/sqft
    $21/mo HOA

    What's special

    Cozy fireplaceModern finishesBeautifully designed contemporary farmhouseQuality craftsmanship throughoutFull sprinkler systemLuxury vinyl plank flooringPeaceful setting
    Welcome to 23 Pennywhistle Drive, a beautifully designed contemporary farmhouse located in one of Windham's most desirable neighborhoods. Built in 2022 and thoughtfully crafted with both comfort and style in mind, this stunning home offers over 2,400 square feet of beautifully finished living space on a private 1+ acre lot. Inside, you'll find a bright and inviting open-concept layout filled with natural light, modern finishes, and quality craftsmanship throughout. The spacious kitchen flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. Luxury vinyl plank flooring, a cozy fireplace, and clean contemporary farmhouse design elements add warmth and character throughout the home. The home features three bedrooms, including a spacious primary suite complete with a private bath and custom built-ins in the closet. In addition to the bedrooms, there is a large bonus room above the garage offering flexible space for a media room, playroom, guest area, or home office. The walkout basement includes an additional bonus room and a convenient half bath, providing even more versatility and functionality. An expansive oversized three-door, four-car garage provides exceptional storage and workspace, perfect for vehicles, outdoor equipment, recreational gear, or hobby space. Designed for efficiency and convenience, the property also features solar panels and a full sprinkler system. Enjoy the peaceful setting while being just minutes from Westbrook, North Windham amenities, shopping, dining, lakes, outdoor recreation, and an easy commute to Portland. This nearly new home offers the perfect blend of modern farmhouse charm, efficiency, and convenience in the heart of Southern Maine.
    67 days
    |
    530
    |
    19
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Better Homes & Gardens Real Estate/The Masiello Group

    Source: Maine Listings,MLS#: 1662103MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 4
      • Full bathrooms: 2
      • 1/2 bathrooms: 2
      Bedroom 1
      • Level: Second
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Exercise room
      • Level: Basement
      Family room
      • Level: Second
      Kitchen
      • Level: First
      Living room
      • Level: First
      Heating
      • Baseboard, Heat Pump, Hot Water, Zoned, Other
      Cooling
      • Heat Pump
      Appliances
      • Included: Cooktop, Dishwasher, Dryer, Gas Range, Refrigerator, Washer
      Features
      • Bathtub, Pantry, Shower, Storage, Primary Bedroom w/Bath
      • Flooring: Luxury Vinyl
      • Windows: Double Pane Windows
      • Basement: Doghouse,Interior Entry,Walk-Out Access,Daylight,Finished,Full
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 2,856
      • Total interior livable area: 2,856 sqft
      • Finished area above ground: 2,476
      • Finished area below ground: 380

      Property

      Parking
      • Total spaces: 3
      • Parking features: Paved, 1 - 4 Spaces, On Site, Off Street, Garage Door Opener, Tandem
      • Attached garage spaces: 3
      Features
      • Levels: Multi/Split
      • Patio & porch: Deck, Porch
      • Has view: Yes
      • View description: Scenic, Trees/Woods
      Lot
      • Size: 1.03 Acres
      • Features: Abuts Conservation, Near Country Club, Near Golf Course, Near Public Beach, Near Town, Neighborhood, Rural, Cul-De-Sac, Level, Landscaped, Wooded
      Details
      • Parcel number: WINMM6B25L16
      • Zoning: F
      • Other equipment: Internet Access Available

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Farmhouse
      • Property subtype: Single Family Residence
      Materials
      • Wood Frame, Vinyl Siding
      • Foundation: Poured Concrete
      • Roof: Composition,Fiberglass,Metal,Shingle
      Condition
      • New Construction
      • New construction: Yes
      • Year built: 2022

      Utilities & green energy

      • Electric: On Site, Circuit Breakers, Generator Hookup, Photovoltaics Seller Owned, Photovoltaics Third-Party Owned
      • Sewer: Private Sewer, Septic Design Available, Septic Tank
      • Water: Well
      Green energy
      • Energy efficient items: Ceiling Fans, Water Heater, Thermostat

      Community & HOA

      Community
      • Security: Fire Sprinkler System, Air Radon Mitigation System
      • Subdivision: Durant Homestead
      HOA
      • Has HOA: Yes
      • HOA fee: $250 annually
      Location
      • Region: Windham

      Financial & listing details

      • Price per square foot: $298/sqft
      • Tax assessed value: $660,700
      • Annual tax amount: $8,573
      • Date on market: 5/16/2026
      • Exclusions: televisions, large cabinet in bonus room
      • Electric utility on property: Yes
      • Road surface type: Paved

        Estimated market value

        $848,200

        $806,000 - $891,000

        $4,867/mo

        Price history

        DateEventPrice
        7/14/2026Contingent$849,900$298/sqft
        Source: Maine Listings #1662103 Report a problem
        6/12/2026Price change$849,900-2.9%$298/sqft
        Source: Maine Listings #1662103 Report a problem
        6/9/2026Listed for sale$874,900$306/sqft
        Source: Maine Listings #1662103 Report a problem
        6/6/2026Contingent$874,900$306/sqft
        Source: Maine Listings #1662103 Report a problem
        5/28/2026Listed for sale$874,900$306/sqft
        Source: Maine Listings #1662103 Report a problem
        5/24/2026Contingent$874,900$306/sqft
        Source: Maine Listings #1662103 Report a problem
        5/16/2026Listed for sale$874,900$306/sqft
        Source: Maine Listings #1662103 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$7,578 +8.6%$660,700 +6.1%
        2023$6,975 +9.9%$622,800 +13.9%
        2022$6,347 +541.8%$546,700 +729.6%
        2020$989 $65,900
        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: 04062

        Getting around

        5 / 100
        Car-Dependent
        19 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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