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

Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham.

The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space.

Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating.

Hardwood floors, abundant windows and doors, central AC throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.

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 and can be reached at 6175153824.

JS

Janet Stuart

Agent at Coldwell Banker Realty

(617) 515-3824
Agent website

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.· 85 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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