About This Home

This 4-bedroom, 4-bathroom single family at 55 Winterset Drive in Chatham, MA is listed for $2,295,000 ($564 per sqft). Built in 1970, the home offers 4,066 sqft of living space on a 1.94 acres lot.

Key Features

  • Built in 1970
  • 1.94 acre lot
  • 3 stories
  • 14 parking spaces
  • Fireplace

Property Details

3 stories
3 full, 1 half
2-car garage
1970

Amenities

FireplaceHardwoodA/C
Listing 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.

Monthly Cost Estimate

$12,349/mo

20% down · 6.5% · 30 years

Principal$1,660
Interest$9,945
Insurance$669
HOA$75

Estimates only. Actual payments may vary.

Location

55 Winterset Drive

Chatham, MA 02633

Great Hills

Features & Amenities

Interior Features

Central VacuumRecessed LightingKitchen IslandBreakfast BarEat-in Kitchen

Exterior Features

Private Yard

Property Details

Flooring

CarpetHardwood

Construction

Shingle Siding

Outdoor Features

PatioDeck

Parking

OpenOff Street

Heating

Natural Gas

Cooling

Central Air

Appliances

Water Heater

Questions & Answers

This 4-bedroom, 4-bathroom single family at 55 Winterset Drive is listed at $2,295,000 ($564/sqft). The estimated monthly payment is $12,349 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance, HOA fees.

HOA fees are $75/month.

Key features include: Built in 1970, 1.94 acre lot, 3 stories, 14 parking spaces, Fireplace. Interior Features: Central Vacuum, Recessed Lighting, Kitchen Island. Exterior Features: Private Yard.

This property is listed by Janet Stuart.

JS

Janet Stuart

Agent at Coldwell Banker Realty

Listed by Coldwell Banker Realty · Broker phone: (508) 962-6990 · View on Broker Site · Broker website

MLS# 22603375· Source: Cape Cod & Islands Association of REALTORS®, Inc.· 108 days on PropertySimple

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

55 Winterset Drive, Chatham, MA 02633

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