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    • Listed by: RE/MAX Town & Country • Vincent Dolan
    Price cut: $5K (5/29)
    $720,000

    27 Headlands Road, Winchester, NH 03470

    2beds
    1,351sqft
    : 
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    Single Family Residence
    Built in 1992
    6,970 Square Feet Lot
    $691,600 Zestimate®
    $533/sqft
    $-- HOA

    What's special

    Direct waterfrontGas fireplaceFamily roomCenter island
    Stunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on Forest Lake. Gorgeous views from every window. Modern Kitchen with stainless appliances and center island. Cozy Living Room with gas Fireplace. The downstairs living area contains a Family Room, Kitchen, Bedroom and Bathroom. This is a perfect year-round retreat or possible short term rental. Also being offered as part of a portfolio of short-term rental properties.
    397 days
    |
    521
    |
    29
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Vincent Dolan,

    RE/MAX Town & Country 603-357-4100,

    Alejandra L Patton Spruill,

    RE/MAX Town & Country

    Source: PrimeMLS,MLS#: 5045812MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 1
      • 1/2 bathrooms: 1
      Heating
      • Baseboard
      Cooling
      • Mini Split
      Appliances
      • Included: Dishwasher, Microwave, Mini Fridge, Gas Range, Refrigerator
      Features
      • Cathedral Ceiling(s), Kitchen Island
      • Flooring: Carpet, Softwood, Vinyl
      • Basement: Finished,Interior Stairs,Walkout,Interior Entry
      • Has fireplace: Yes
      • Fireplace features: Gas
      Interior area
      • Total structure area: 1,471
      • Total interior livable area: 1,351 sqft
      • Finished area above ground: 973
      • Finished area below ground: 378

      Property

      Parking
      • Total spaces: 4
      • Parking features: Gravel, Parking Spaces 4
      Features
      • Levels: One and One Half
      • Stories: 1.5
      • Exterior features: Boat Mooring, Dock, Deck, Shed
      • Has view: Yes
      • View description: Lake
      • Water view: Lake
      • Waterfront features: Lake Front, Waterfront
      • Body of water: Forest Lake
      • Frontage length: Road frontage: 71
      Lot
      • Size: 6,970 Square Feet
      • Features: Sloped
      Details
      • Parcel number: WNCHM00033B000016L000000
      • Zoning description: Forest Lake District

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape
      • Property subtype: Single Family Residence
      Materials
      • Post and Beam, Wood Frame
      • Foundation: Concrete, Poured Concrete
      • Roof: Architectural Shingle
      Condition
      • New construction: No
      • Year built: 1992

      Utilities & green energy

      • Electric: 100 Amp Service, Circuit Breakers
      • Sewer: Private Sewer, Septic Tank
      • Utilities for property: Cable Available, Propane, Underground Gas

      Community & HOA

      Community
      • Security: Smoke Detector(s)
      HOA
      • Amenities included: Beach Access, Beach Rights
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $533/sqft
      • Tax assessed value: $294,800
      • Annual tax amount: $9,340
      • Date on market: 6/11/2025

        Estimated market value

        $691,600

        $657,000 - $726,000

        $2,162/mo

        Price history

        DateEventPrice
        5/29/2026Price change$720,000-0.7%$533/sqft
        Source: PrimeMLS #5045812 Report a problem
        11/19/2025Price change$725,000-1.4%$537/sqft
        Source: PrimeMLS #5045812 Report a problem
        6/11/2025Listed for sale$735,000+13.1%$544/sqft
        Source: PrimeMLS #5045812 Report a problem
        12/22/2022Sold$650,000-4.3%$481/sqft
        Source: PrimeMLS #4911086 Report a problem
        12/21/2022Contingent$679,000$503/sqft
        Source: PrimeMLS #4911086 Report a problem
        5/20/2022Listed for sale$679,000+153%$503/sqft
        Source: PrimeMLS #4911086 Report a problem
        5/15/2019Sold$268,391-6.5%$199/sqft
        Source: PrimeMLS #4742566 Report a problem
        4/9/2019Pending sale$287,000$212/sqft
        Source: Keller Williams Realty Metropolitan #4742566 Report a problem
        3/29/2019Listed for sale$287,000$212/sqft
        Source: Keller Williams Realty-Metropolitan #4742566 Report a problem
        12/17/2018Listing removed$287,000$212/sqft
        Source: BH&G - The Masiello Group #4696476 Report a problem
        10/2/2018Price change$287,000-0.7%$212/sqft
        Source: Better Homes & Gardens Real Estate/The Masiello Group #4696476 Report a problem
        7/26/2018Price change$289,000-2%$214/sqft
        Source: Better Homes & Gardens Real Estate/The Masiello Group #4696476 Report a problem
        5/30/2018Listed for sale$295,000-1.3%$218/sqft
        Source: BH&G - The Masiello Group #4696476 Report a problem
        12/16/2017Listing removed$299,000$221/sqft
        Source: Better Homes & Gardens Real Estate/The Masiello Group #4628399 Report a problem
        4/20/2017Listed for sale$299,000-0.3%$221/sqft
        Source: BH&G - The Masiello Group #4628399 Report a problem
        1/2/2017Listing removed$299,950$222/sqft
        Source: RE/MAX Town Country #4478531 Report a problem
        3/25/2016Listed for sale$299,950-2.9%$222/sqft
        Source: RE/MAX Town Country #4478531 Report a problem
        12/8/2015Listing removed$309,000$229/sqft
        Source: Better Homes and Gardens Real Estate The Masiello Group #4418351 Report a problem
        7/10/2015Price change$309,000-0.6%$229/sqft
        Source: Better Homes and Gardens Real Estate The Masiello Group #4418351 Report a problem
        5/5/2015Listed for sale$311,000-2.5%$230/sqft
        Source: Better Homes and Gardens Real Estate The Masiello Group #4418351 Report a problem
        11/2/2014Listing removed$319,000$236/sqft
        Source: Better Homes and Gardens-The Masiello Group #4352899 Report a problem
        5/6/2014Listed for sale$319,000+25.1%$236/sqft
        Source: Better Homes and Gardens-The Masiello Group #4352899 Report a problem
        1/31/2005Sold$255,000+100%$189/sqft
        Source: Public Record Report a problem
        1/18/2001Sold$127,500$94/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$8,623 -8.6%$294,800 -1%
        2023$9,434 +24.4%$297,800 +12.7%
        2022$7,585 +0.5%$264,300 +0.8%
        2021$7,546 $262,300
        2020$7,546 -11.9%$262,300 +9.2%
        2019$8,564 +2.6%$240,300
        2018$8,346 +32.8%$240,300 +16.7%
        2016$6,286 -0.2%$205,900
        2015$6,296 -7%$205,900 -7%
        2014$6,767 -0.9%$221,300 -0.4%
        2013$6,831 +10.1%$222,300
        2012$6,207 -7%$222,300
        2011$6,676 -2.9%$222,300 -12.9%
        2009$6,875 -4.7%$255,200
        2008$7,215 +3.2%$255,200
        2007$6,992 $255,200
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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: 03470

        Getting around

        0 / 100
        Car-Dependent
        1 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Winchester School
        • District: Winchester

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

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