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355 Boylston St / (617) 233-5800

55 Winterset Drive

Chatham, MA ID #73548377

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55 Winterset Drive

- Chatham, MA ID #73548377

Property Description

This 4BR Contemporary Cape is set back at the end of a quiet cul-de-sac on just under two acres offering privacy and nature at every turn. As part of Great Hill, this home includes deeded rights to Lover's Lake for swimming, kayaking, and canoeing just a short footpath away. Features include hardwood floors, lots of windows and french doors for loads of sunlight, open floor plan, vaulted ceilings and multiple decks all perfect for entertaining and large family gatherings. The first floor includes two great rooms each with vaulted beamed ceilings, one with a gas fireplace and one with a wood-burning fireplace, a renovated kitchen with a wall of windows at the kitchen sink overlooking the property, a large dining area, a half bath and a primary suite with ensuite renovated bathroom with large walk-in shower and laundry. Off the great room is a large wraparound deck with gas connection for the grill and room for full dining, lounging and taking in the professionally landscaped grounds, sprawling flower beds and quaint stone walls. Off the other great room and connecting with the kitchen is another deck overlooking the property with a perfect spot for morning coffee, reading and relaxing. On the second floor is a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath with shower and separate spa tub. The lower level has a bedroom with sitting area and full window, a full bath, another laundry, and walk-out access to a stone patio with custom stone wraparound seating and a built-in gas fire-pit. Enjoy brand new Bosch heating system, central a/c, central vac, attached 2 car garage, gas connection and town water. Key location with easy access to Route 6 for commuting off cape and the outer cape areas.yet a 5-minute drive to Chatham Village, Chatham Light, Lighthouse Beach, Chatham Bars Inn, Seaside Links Golf Course, and Hardings Beach. Steps to tennis courts, pickleball courts and the Chatham Scenic Bike Loop connecting to the Cape Cod Rail Trail bike path. House comes fully furnished.

Additional Details

  • Status: Active
  • Type: Single Family, Single Family Residence
  • Zip Code: 02633
  • HOA Fee: $75
  • Taxes: 5,655
  • Acres: 1.94

Parking

  • Garage: 2
  • Garage Capacity: 2
  • Parking: Paved, Attached, Garage Door Opener, Garage Faces Side, Off Street, Garage
  • Parking Spaces: 10

Rooms/Dimensions

  • Total Rooms: 8
  • Has Basement: Yes

Location

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55 Winterset Drive, Chatham, MA

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Content © 2026 MLS Property Information Network, Inc.
The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Janet Stuart of Coldwell Banker Realty - Concord. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.