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55 Winterset Drive, Chatham MA 02633

$2,295,000

Estimated $14,612/month Calculator

Single Family

4 Bedrooms

Baths

4072

Total Parking: 12 (2 Garage)

84,506 (1.94)

Built in 1970

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.

This home has been viewed 56 times

Last Checked: October 26th, 2026 at 4:28am (Source: MLS PIN #73548377)

Garage Parking

Air Conditioning

Waterview

Lead Paint Free

General Information for 55 Winterset Drive, Chatham MA 02633

Listing ID73548377

Property TypeSingle Family / Detached

Price$2,295,000 ($563.61/SqFt)

StyleColonial

CityChatham

CountyBarnstable

Neighborhood(s)

Garage Parking2

Zoningres

Association0

Year Built1970

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 55 Winterset Drive, Chatham MA 02633

Approximate Living Area Total4072

Living Area Includes BasementYes

Rooms8

Bedrooms4

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric220 Volts

Exterior Features for 55 Winterset Drive, Chatham MA 02633

Approximate Lot Size (Acres)1.94

Approximate Lot Size (Square Feet)84506

Total Parking12 (2 Garage)

Garage Parking2

WaterPublic

SewerPrivate Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction MaterialsFrame

Road Frontage Type

Patio & PorchCovered

Roof MaterialAsphalt/fiberglass Shingles

Utility Connections110 Volts

Water ViewsNo

Water Views Features

Waterfront0

Waterfront FeaturesRiver

Pool Features

Horse Permitted0

Horse AmenitiesRiver

Disclosures for 55 Winterset Drive, Chatham MA 02633

Lead PaintNone

UFFI

Living Area Includes BasementYes

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsAll Tenant Possessions

Title 5A

Compensation Based On

Financial Information for 55 Winterset Drive, Chatham MA 02633

Association0

Association Fee

Association Fee FrequencyAnnually

Association Fee Includes

Real Estate Tax5655

Tax Year2026

Assessed Value$1,540,900

Location Information for 55 Winterset Drive, Chatham MA 02633

Elementary SchoolChatham

Middle SchoolChatham

High SchoolMonomoy

Neighborhood(s)

Area AmenitiesWalk/jog Trails

Contact Information for 55 Winterset Drive, Chatham MA 02633

Agent

Name: Janet Stuart

Office

Name: Coldwell Banker Realty - Concord

Phone: 978-369-1000

Payment Calculator

, Interest

Property Taxes 471.25

Principal & Interest 14141.06

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Coldwell Banker Realty - Concord

Janet Stuart

Agent Phone

Office Phone

(978) 369-1000

Text Agent Call Agent Call Office

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EXIT

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