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55 Winterset Drive, Chatham MA 02633

$2,390,000

Estimated $15,198/month Calculator

Single Family

4 Bedrooms

Baths

4072

Total Parking: 16 (2 Garage)

84,506 (1.94)

Built in 1970

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.

This home has been viewed 11 times

Last Checked: July 12th, 2026 at 4:33pm (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$2,390,000 ($586.94/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 Parking16 (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 Connections

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

ExclusionsSome Of The Sellers' Personal Items Are Not Included In The Sale.

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 14726.42

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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