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For sale
  • Price cut: $95K (9/11)
    $2,295,000

    55 Winterset Drive, Chatham, MA 02633

    4beds
    4,066sqft
    : 
    $13,502/mo
    Get pre-qualified
    Single Family Residence
    Built in 1970
    1.94 Acres Lot
    $2,213,600 Zestimate®
    $564/sqft
    $6/mo HOA

    What's special

    Brand-new bosch heating systemWraparound decksHardwood floorsNew roofWalkout lower levelPrivate natural settingCentral ac throughout
    Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central AC throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.
    86 days
    733
    35

    Zillow last checked:

    Listing updated:

    Listed by:

    Janet Stuart 617-515-3824,

    Coldwell Banker Realty

    Source: CCIMLS,MLS#: 22603375MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Heating
      • Natural Gas
      Cooling
      • Central Air
      Appliances
      • Included: Natural Gas, Water Heater
      Features
      • Central Vacuum, Recessed Lighting
      • Flooring: Hardwood, Carpet
      • Basement: Finished,Full
      • Number of fireplaces: 4
      Interior area
      • Total structure area: 4,066
      • Total interior livable area: 4,066 sqft

      Property

      Parking
      • Total spaces: 14
      • Parking features: Direct Access, Garage Door Opener, Off Street, Paved
      • Garage spaces: 2
      Features
      • Stories: 3
      • Patio & porch: Deck, Patio
      • Fencing: Partial
      Lot
      • Size: 1.94 Acres
      • Features: Corner Lot
      Details
      • Parcel number: CHAT M:0011G B:0074 L:H1080
      • Special conditions: Standard

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Shingle Siding
      • Roof: Asphalt,Shingle
      Condition
      • Year built: 1970

      Utilities & green energy

      • Water: Public

      Community & HOA

      Community
      • Subdivision: Great Hills
      HOA
      • Has HOA: Yes
      • Amenities included: Beach Access
      • HOA fee: $75 annually
      Location
      • Region: Chatham

      Financial & listing details

      • Price per square foot: $564/sqft
      • Tax assessed value: $1,540,900
      • Annual tax amount: $5,655
      • Date on market: 7/13/2026
      • Cumulative days on market: 76 days

        Estimated market value

        $2,213,600

        $2.10M - $2.32M

        $4,776/mo

        Price history

        DateEventPrice
        10/2/2026Listed for sale$2,295,000$564/sqft
        Source: CCIMLS #22603375 Report a problem
        9/24/2026Pending sale$2,295,000$564/sqft
        Source: CCIMLS #22603375 Report a problem
        9/23/2026Contingent$2,295,000$564/sqft
        Source: MLS PIN #73548377 Report a problem
        9/11/2026Price change$2,295,000-4%$564/sqft
        Source: CCIMLS #22603375 Report a problem
        7/11/2026Listed for sale$2,390,000+4.1%$588/sqft
        Source: MLS PIN #73548377 Report a problem
        11/22/2025Listing removed$2,295,000$564/sqft
        Source: CCIMLS #22502257 Report a problem
        8/27/2025Price change$2,295,000-4.2%$564/sqft
        Source: CCIMLS #22502257 Report a problem
        8/14/2025Price change$2,395,000-2%$589/sqft
        Source: CCIMLS #22502257 Report a problem
        8/1/2025Price change$2,445,000-2%$601/sqft
        Source: CCIMLS #22502257 Report a problem
        5/14/2025Listed for sale$2,495,000+41%$614/sqft
        Source: CCIMLS #22502257 Report a problem
        4/10/2023Sold$1,770,000-1.4%$435/sqft
        Source: CCIMLS #22300802 Report a problem
        3/12/2023Pending sale$1,795,000$441/sqft
        Source: CCIMLS #22300802 Report a problem
        3/10/2023Listed for sale$1,795,000+88%$441/sqft
        Source: CCIMLS #22300802 Report a problem
        8/29/2003Sold$955,000+267.3%$235/sqft
        Source: Public Record Report a problem
        6/7/1999Sold$260,000$64/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,180 +3%$1,492,700 +5.9%
        2024$5,030 +10.2%$1,409,000 +19.7%
        2023$4,566 +16.4%$1,176,800 +38.6%
        2022$3,922 $849,000
        2021$3,922 +8.7%$849,000 +13.4%
        2020$3,609 +2.3%$748,700 +2.9%
        2019$3,528 +6.5%$727,400 +6.9%
        2018$3,314 -0.3%$680,400 +3%
        2017$3,323 +1.3%$660,700 +1.1%
        2016$3,281 +1.8%$653,600 +1.2%
        2015$3,223 -1.6%$645,800 +0.1%
        2014$3,276 +4.2%$644,900 +3.2%
        2013$3,144 +4.7%$625,100 -7.3%
        2012$3,002 +4%$674,500
        2011$2,887 +12%$674,500
        2010$2,577 -5.7%$674,500 -7.7%
        2009$2,733 -3.3%$730,700 -5.1%
        2008$2,826 $770,100
        2007$2,826 $770,100
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 02633

        Getting around

        21 / 100
        Car-Dependent
        26 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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