Skip to main contentSkip to navigation
1 / 43

Land with Home for Sale in Chatham, Massachusetts

55 Winterset Dr, Chatham, MA 02633

$2,295,000
2 acres
Active sale
$95k drop
Est $13,065/mo

Wonderfully renovated and expanded Contemporary Cape set back at the end of a quiet cul-de-sac on just under two acres offering total 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.

4,066
Sq feet
4
Beds
3
Full baths
1
1/2 bath
1970
Built

Location

Street address
55 Winterset Dr
Zip code
02633
Community
Great Hills
School district
Monomoy
Elevation
47 feet
Coordinates
41.6942, -69.977

Directions

Old Queen Anne Road to Winterset Drive, house located at the end on the left.

Property details

Acreage
1.94 acres84,506 sq ft
Zoning
R60
MLS #
CCIAOR 22603375
Posted

Property taxes

2026
$5,655

Expenses

Homeowner Association Fee
$75 annually

Parcels

  • CHAT M:0011G B:0074 L:H108-0

Details and features

Listing

Type
Residential
Subtype
Single Family Residence
Franchise
Coldwell Banker Real Estate

Lot

Features
Corner Lot

Exterior

Parking Spaces
14
Parking
Off Street, Open
Pool
Deck, Patio
Features
Private Yard

Structure

Style
Cape Cod, Contemporary
Stories
3
Basement
Finished, Full, Walk-Out Access
Water
Public
Sewer
Septic Tank
Heating
Natural Gas
Cooling
Central Air
Materials
Shingle Siding
Roof
Asphalt, Shingle

Interior

Room Count
8
Rooms
Basement, Bathroom x 4, Bedroom x 4
Flooring
Carpet, Hardwood
Fireplaces
Yes
Appliances
Water Heater
Features
Breakfast Bar, Central Vacuum, Eat-In Kitchen, Kitchen Island, Recessed Lighting

Property utilities

CategoryTypeStatus
GasNatural GasConnected

Listing history

DateEventPriceChangeSource
Oct 2, 2026Back on market$2,295,000—CCIAOR
Sept 24, 2026Under contract$2,295,000—CCIAOR
Sept 11, 2026Price drop$2,295,000$95,000 -4%CCIAOR
July 13, 2026New listing$2,390,000—CCIAOR
Subscribe to listing updates

Payment calculator

This 1.94-acre property is located at 55 Winterset Dr in Chatham, MA 02633. The property is available for sale, priced at $2,295,000. It has a 4,066 square foot 4-bedroom, 3.5-bath house built in 1970.

Listed by Coldwell Banker Realty, (508) 962-6990

Checked 1 hour agoUpdated Source

Report listing issue

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.

Contact listing agent Rules
By submitting, I agree to the terms of use and to be contacted by real estate professionals. Message and data rates may apply.
Contact