55 Winterset DriveChatham, MA 02633MLS Number 73548377

  • Price: $2,295,000
  • Est. Mortgage of $/month
  • 92 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 8, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • 4Bedrooms
  • 1.94Acreage
  • 4Bathrooms
  • 1970Year Built
Active
55 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 0263355 Winterset Drive Chatham MA 02633
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Cape Coastal Sotheby's International Realty
Cape Coastal Sotheby's International Realty
Office: 508-477-6688
540 Falmouth Road (Mashpee Rotary)
Mashpee, MA 02649
Set high on 1.8 acres at the end of a quiet cul-de-sac, this expanded renovated contemporary Cape offers privacy, beautiful natural surroundings, and an exceptional setting for large family gatherings and entertaining. Located in one of Chatham's most sought-after areas, the home offers the best of both worlds-a peaceful, private setting with convenient access to Chatham Village, the bike path, and some of Chatham's most beautiful beaches. As a member of the Great Hill Estates Association, the property also includes rights to Lovers Lake. Treetop views, abundant windows, and multiple decks bring the beauty of the setting into the home. The expansive outdoor living spaces are designed for entertaining, with a large deck, additional seating areas, a gas line for grilling, and a stone patio with a gas fire pit and built-in stone seating. A fenced area in the backyard provides a convenient space for a dog. The first floor features two spacious great rooms, each with dramatic open-beamed ceilings and fireplaces, along with a large kitchen with granite countertops, island seating, and an open dining area. A half bath and first-floor primary suite with an en-suite full bath and laundry complete the main level. Upstairs, another bedroom offers its own fireplace and sitting area, along with an additional bedroom and full bath. The lower level provides a fourth bedroom, full bath, laundry, and walkout access to the patio. With generous living spaces indoors and out, this home is perfectly suited for entertaining, holidays, and gathering with family and friends. A new Bosch heating system adds peace of mind. Enjoy the privacy and natural beauty of this special property while being just minutes from all that makes Chatham such a sought-after destination.

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Basic Information

  • Bedrooms4
  • Mls StatusActive
  • Bathroom4
  • Lot Features Corner Lot
  • Parcel Number 2260871

Basic Information

  • List Price$2,295,000
  • MLSPIN 73548377
  • Modification Date10/06/2026
  • Property SubTypeSingle Family Residence
  • Virtual TourView Tour

Building

  • Attached Garage YN Yes
  • BasementFull, Finished, Walk-Out Access, Interior Entry, Garage Access
  • Building Area Units Square Feet
  • Construction Materials Frame
  • Door Features Insulated Doors, French Doors
  • FireplaceYes
  • Fireplace Features Family Room, Living Room, Bedroom
  • Fireplaces Total 4
  • FoundationConcrete Perimeter
  • Garage Spaces2
  • Patio And Porch Features Deck, Patio
  • Property StyleCape, Contemporary
  • Rooms8
  • Utilities For Gas Range, For Gas Dryer, Outdoor Gas Grill Hookup
  • Window Features Insulated Windows
  • Year Built1970
  • Year Built Details Actual
  • Year Built Source Public Records

Other

  • Association Fee $75
  • Association Fee Frequency Annually
  • Association YN Yes
  • Date Listed07/11/2026
  • Farm Land Area Units Square Feet
  • View Count7

Tax Information

  • Tax Assessed Value $1,540,900
  • Tax Year 2026
  • Taxes$5,655

Parking

  • Parking Spaces14
  • Covered Spaces 2
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features
    • Attached
    • Garage Door Opener
    • Garage Faces Side
    • Off Street
    • Paved Drive
    • Under

Location

  • SubdivisionGreat Hill
  • Address55 Winterset Drive
  • Building Number55
  • CountyBarnstable
  • StateMA
  • StreetWinterset Drive
  • TownChatham
  • Zip02633

Property

  • Acreage1.94

Exterior

  • Exterior Features Deck, Patio, Professional Landscaping, Outdoor Gas Grill Hookup
  • RoofShingle

Property Information

  • Square Feet4,072
  • Building Area Source Public Records
  • Living Area 4,072
  • Lot Size Square Feet 84,506
  • Lot Size Units Acres

Amenities

  • Amenities
    • Bike Path
    • Conservation Area
    • Golf
    • Highway Access
    • House of Worship
    • Marina
    • Medical Facility
    • Park
    • Public School
    • Shopping
    • Tennis Court(s)
    • Walk/Jog Trails
  • Appliances IncludedGas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/Dryer
  • Security Features Security System

School Information

  • High School Monomoy
  • Elementary SchoolChatham
  • High SchoolMonomoy Regional
  • Junior HighChatham

Rooms

  • Bathroom 1 First
  • Bathroom 2 First
  • Bathroom 3 Second
  • Bathrooms Total Decimal 3.5
  • Bedroom 2 Second
  • Bedroom 3 Second
  • Bedroom 4 Basement
  • Dining Room Main, First
  • Family Room First
  • Full Bath3
  • Half Baths1
  • Kitchen First
  • Living Room Main, First
  • Main Level Bedrooms 1
  • Master Bedroom Main, First

Interior

  • Flooring Tile, Carpet, Hardwood
  • Interior Features Bathroom

Utilities

  • Cooling Central Air, Ductless
  • Cooling YN Yes
  • Electric 200+ Amp Service
  • Heat SystemYes
  • Heating Baseboard, Natural Gas
  • Sewer Private Sewer
  • Water Source Public

Water Body

  • Miles to Beach0.1
  • Waterfront Features Lake/Pond,0 to 1/10 Mile To Beach, Beach Ownership(Private)

Driving Directions

Listed by Janet Stuart of Coldwell Banker Realty - Concord

Chatham, MA Demographics

There is no data available

Chatham, MA Real Estate Market Data

There is no data available

Chatham, MA Schools

School NameDistanceTypeGrades

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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