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For sale
  • Price cut: $50K (8/1)
    $2,445,000

    55 Winterset Drive, Chatham, MA 02633

    4beds
    4,072sqft
    : 
    Single Family Residence
    Built in 1970
    1.94 Acres Lot
    $2,318,200 Zestimate®
    $600/sqft
    $-- HOA

    What's special

    Tennis courtStunning stone wallsWrap-around decksGuest room and bathCathedral great roomsDaylight lower levelSprawling lawn
    Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. May be sold furnished.
    89 days
    on Zillow
    |
    1,056
    |
    43
    |

    Zillow last checked: 7 hours ago

    Listing updated: August 01, 2025 at 05:31pm

    Listed by:

    Tara J Schiffmann 774-810-6381,

    Bayview Real Estate

    Source: CCIMLS,MLS#: 22502257MLS Logo
    Travel times

    Tour with a buyer's agent

    We'll find a local expert to take you on a private tour of 55 Winterset Drive.

    Next available tour time:Today at 11am

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 4
    • Full bathrooms: 3
    • 1/2 bathrooms: 1
    • Main level bathrooms: 2
    Primary bedroom
    • Description: Flooring: Carpet
    • Features: Recessed Lighting
    • Level: First
    Bedroom 2
    • Description: Fireplace(s): Wood Burning,Flooring: Carpet
    • Features: Bedroom 2, Shared Full Bath, Walk-In Closet(s), Recessed Lighting
    • Level: Second
    Bedroom 3
    • Description: Flooring: Carpet
    • Features: Bedroom 3, Closet
    • Level: Second
    Bedroom 4
    • Description: Flooring: Carpet
    • Features: Bedroom 4
    • Level: Basement
    Primary bathroom
    • Features: Private Full Bath
    Dining room
    • Description: Flooring: Wood,Door(s): French
    • Features: Dining Room
    • Level: First
    Kitchen
    • Description: Flooring: Wood,Stove(s): Gas
    • Features: Pantry, Upgraded Cabinets, Kitchen Island
    Living room
    • Description: Fireplace(s): Wood Burning,Flooring: Wood
    • Features: Cathedral Ceiling(s), Living Room, Beamed Ceilings
    Heating
    • Hot Water, Other
    Cooling
    • Has cooling: Yes
    Appliances
    • Included: Dishwasher, Washer, Refrigerator, Microwave, Gas Water Heater
    • Laundry: Laundry Room, In Basement
    Features
    • Recessed Lighting, Pantry, Mud Room, Linen Closet, HU Cable TV
    • Flooring: Hardwood, Carpet, Tile, Other
    • Doors: French Doors
    • Windows: Bay/Bow Windows
    • Basement: Bulkhead Access,Interior Entry,Full,Finished
    • Number of fireplaces: 4
    • Fireplace features: Wood Burning
    Interior area
    • Total structure area: 4,072
    • Total interior livable area: 4,072 sqft

    Property

    Parking
    • Total spaces: 6
    • Parking features: Basement
    • Attached garage spaces: 2
    • Has uncovered spaces: Yes
    Features
    • Stories: 2
    • Entry location: First Floor
    • Exterior features: Garden
    • Fencing: Fenced
    Lot
    • Size: 1.94 Acres
    • Features: Bike Path, Near Golf Course, Marina, Conservation Area, Cleared, East of Route 6, North of Route 28
    Details
    • Parcel number: 11G74H108
    • Zoning: R60
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • Shingle Siding
    • Foundation: Block, Slab
    • Roof: Asphalt, Pitched, Flat
    Condition
    • Updated/Remodeled, Actual
    • New construction: No
    • Year built: 1970
    • Major remodel year: 1999

    Utilities & green energy

    • Sewer: Private Sewer

    Community & HOA

    Community
    • Features: Deeded Beach Rights
    • Subdivision: Great Hills Estates
    HOA
    • Has HOA: Yes
    Location
    • Region: Chatham

    Financial & listing details

    • Price per square foot: $600/sqft
    • Tax assessed value: $2,122,900
    • Annual tax amount: $5,179
    • Date on market: 5/14/2025
    • Road surface type: Paved
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