For Sale
Price CutPrice Drop: $95K (10/02)
Single family home for sale at 55 Winterset Dr, Chatham, MA 02633 | MLS# 73548377 | Listing updated on 2026-10-25
Photo 1 of Single family home for sale at 55 Winterset Dr, Chatham, MA 02633 | MLS# 73548377 | Listing updated on 2026-10-25
Photo 2 of Single family home for sale at 55 Winterset Dr, Chatham, MA 02633 | MLS# 73548377 | Listing updated on 2026-10-25
Photo 3 of Single family home for sale at 55 Winterset Dr, Chatham, MA 02633 | MLS# 73548377 | Listing updated on 2026-10-25
Photo 4 of Single family home for sale at 55 Winterset Dr, Chatham, MA 02633 | MLS# 73548377 | Listing updated on 2026-10-25
36+
Beds Icon

Street View

$2,295,000

Monthly Est:$11,423

  • Beds Icon4 Beds
  • Beds Icon
    4 Baths
  • Beds Icon4,072sqft

55 Winterset Dr, Chatham, MA 02633

$11,423/moEst:

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  • Single Family Residence

  • Built in 1970

  • $6.25/mo HOA

  • 1.94 acres lot

  • $564/sq.ft

Description

Renovated and expanded Contemporary Cape at the end of a cul-de-sac on just under two acres allows for a unique amount of privacy while being less than a five minute drive to Chatham Village, Chatham Lighthouse, the Chatham Bars Inn and all that Chatham has to offer. As part of Great Hill Estates, this home has deeded rights to Lover's Lake for swimming, kayaking and canoeing. This home offers large open spaces perfect for entertaining and large gatherings. The first floor has a family room with vaulted beamed ceiling and wood burning fireplace open to a kitchen with large island and dining area, another large living room with gas fireplace open to a wraparound deck for grilling, dining and enjoying the views of nature looking out over the property. Enjoy a first floor primary with ensuite bathroom including laundry and a half bath. Upstairs are two more bedrooms, one as a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath. The lower level has a bedroom, a full bath, second laundry, and walk-out access to a stone patio with custom stone seating area and a built-in gas fire-pit. Features including central a/c, hardwood floors, two car attached garage, brand new Bosch heating system and newer roof. Just steps away from the Cape Cod Rail Trail Bike Path, tennis courts, and pickleball courts. Home is being offered fully furnished.

  • Houzeo last checked: 37 minutes ago
  • Listing updated: October 25, 2026 at 2:33 am
  • Listing Provided by: Janet Stuart (617) 515-3824 | Coldwell Banker Realty - Concord (978) 369-1000
  • Source: MLS Property Information Network-MA | MLS#: 73548377 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Barnstable County

  • City

    Chatham

  • Neighborhood

    --

  • Year Built

    1970

  • HOA Fees

    $6.25/mo

  • Finished Area

    4,072 sqft

  • Lot Size

    1.94 acres lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73548377

  • MLS Status

    Active

  • Days on Market

    107

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Location

HOA Management

N/A

HOA Fees

$75/ Annually

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 4

Interior

  • Heating

    Baseboard, Natural Gas

  • Cooling

    Central Air, Ductless

  • Appliances

    Gas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/dryer

  • Exterior Features

    Deck, Patio, Professional Landscaping, Outdoor Gas Grill Hookup

  • Interior Features

    Bathroom

  • Sewer

    Private Sewer

  • Window Features

    Insulated Windows

  • Flooring

    Tile, Carpet, Hardwood

Construction

  • Year Built

    Year Built: 1970

  • Home type

    Single Family Residence

  • Architectural Style

    Cape, Contemporary

  • Foundation Details

    Concrete Perimeter

  • Roof

    Shingle

  • Construction Materials

    Frame

Utilities & Energy

  • Utilities

    For Gas Range, For Gas Dryer, Outdoor Gas Grill Hookup

  • Parking Features

    Attached, Under, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street

  • Electric

    200+ Amp Service

  • Fireplace Features

    Family Room, Living Room, Bedroom

  • Basement

    Full, Finished, Walk Out Access, Interior Entry, Garage Access

  • Laundry Features

    First Floor, Gas Dryer Hookup

  • Water Source

    Public

  • Security Features

    Security System

Other Features

  • Patio And Porch Features

    Deck, Patio

  • Disclosures

    Home Being Sold Fully Furnished.

  • Lot Features

    Corner Lot

  • Community Features

    Shopping, Tennis Court(s), Park, Walk/jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House Of Worship, Marina, Public School

Price History

DateEventPrice

10/02/2026

Source: mls_logoCape Cod And Islands MLS-MA #22603375

Listed for Sale

$2,295,000

$564/sqft

09/23/2026

Source: mls_logoMLS Property Information Network-MA #73548377

Contingent (Active Under Contract)

$2,295,000

$564/sqft

09/11/2026

Source: mls_logoCape Cod And Islands MLS-MA #22603375

Pending

$2,295,000 -3.97%

$564/sqft

07/11/2026

Source: mls_logoMLS Property Information Network-MA #73548377

Listed for Sale

$2,390,000 +4.14%

$588/sqft

11/22/2025

Source: mls_logoCape Cod And Islands MLS-MA #22502257

Listing Removed

$2,295,000 -4.18%

$564/sqft

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Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 27, 2026, 01:15PM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. 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. MLS Property Information Network, Inc. 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. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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