About This Home

This 4-bedroom, 4-bathroom single family at 55 Winterset Drive in Chatham, MA is listed for $2,390,000 ($588 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
14 spaces
1970

Amenities

FireplaceHardwoodA/C
Listing Description

Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & views of nature at every turn.

Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath.

Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Possible subdivision opportunity.

Monthly Cost Estimate

$12,857/mo

20% down · 6.5% · 30 years

Principal$1,728
Interest$10,357
Insurance$697
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

HardwoodCarpet

Construction

Shingle Siding

Pool 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 $2,390,000 ($588/sqft). The estimated monthly payment is $12,857 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

Listed by Coldwell Banker Realty · View on Broker Site

MLS# 22603375· Source: listhub· 2 days on market

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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