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55 Winterset Drive Chatham, MA $ 2,390,000
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$ 2,390,000 Get more info
55 Winterset Drive
$ 2,390,000
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55 Winterset Drive

Chatham, MA, 02633
$ 2,390,000
Bedrooms4 Baths3.1 Sq 4,066

Monthly Estimate*

$ 15,091

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Single Family Home for sale in Chatham, MA

for $2,390,000 with 4 bedrooms and 3 full baths, 1 half bath. This 4,066 square foot home was built in 1970 on a lot size of 1.94.

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.

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Single Family Active

Price

$ 2,390,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 5,655

Style

Cape Cod, Contemporary

Lot Size

1.94

Year Built

1970

Town/City

Chatham

County/Region

Barnstable

MLS | Web ID

22603375
Features
General
Sewer Septic Tank
Heating Hot Water
Cooling Central Air
Roof Asphalt Shingle
Appliances Gas Water Heater
Zoning R60
HOA Fee 75
Garage Spaces 2
Patio/Porch Features Deck Patio
Architectural Style Cape Cod Contemporary
Construction Materials Shingle Siding
Year Built 1970
Stories Count 3
Township Chatham
Property Subtype Single Family Residence
Tax Year 2026
Assoc Fee Paid Per Annually
County Barnstable
New Construction false
Property Type Residential
HOA true
Attached Garage false
Subdivision Name Great Hills
Garage Y/N true
Total Rooms 8
Full Baths 3
Status Active
Directions Old Queen Anne Road to Winterset Drive house located at the end on the left.
City Chatham
High School District Monomoy
MLS Area West Chatham
Lot Size Units Acres
Lot Size Square Feet 84506
Carport Y/N false
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 5655
Showing Instructions Call Listing Agent Janet Stuart at 617-515-3824 for all showings.
Home Warranty Y/N false
Property Condition Updated/Remodeled Actual
Building Area Units Square Feet
Primary Bedroom Level First
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District Monomoy
Elementary School District Monomoy
Tax Assessed Value 1540900
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Interior
Interior Amenities Recessed Lighting
Basement Finished Interior Entry Full
Flooring Hardwood Carpet
Total Fireplaces 4
Kitchen Level First
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 1
Laundry Features Laundry Room First Floor
Total Bedrooms 4
Living Room Level First
Main Level Bathrooms 2
Below Grade Finished Area Unit Type Square Feet
Kitchen Features Kitchen Breakfast Bar Kitchen Island Recessed Lighting
Total Baths 4
Primary Bathroom Features Private Full Bath
Living Room Features Recessed Lighting Shared Half Bath Living Room Beamed Ceilings Cathedral Ceiling(s)
Bedroom 4 Features Bedroom 4
Bedroom 3 Features Bedroom 3 Closet
Bedroom 2 Features Office/Sitting Area Closet
Dining Room Features Recessed Lighting Shared Half Bath Dining Room
Kitchen Description Countertop(s): Granite Flooring: Wood Door(s): French
Primary Bedroom Features Laundry Areas Closet
Dining Room Level First
Bedroom 4 Level Basement
Bedroom 3 Level Second
Second Bedroom Level Second
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Exterior
Fencing Partial
Parking Features Basement
Lot Features Bike Path School Medical Facility Major Highway House of Worship Near Golf Course Cape Cod Rail Trail Shopping Public Tennis Marina Conservation Area Cul-De-Sac
Water Source Well
Total Parking 14
Lot Size Area 1.94
Foundation Details Poured
Building Area Total 4066
Lot Size Acres 1.94
Road Surface Type Paved
Lot Size Source Field Card
Waterfront Y/N false
Door Features French
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* Excluded Features
List By
Janet Stuart

Listing Agent

Coldwell Banker Realty

Broker

janet.stuart@nemoves.com

Email

Affordability Calculator

$15,562
Per Month
97%
3%
0%
Monthly Principal & Interest
$15,091
Monthly Property Taxes
$471
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4750209 Elementary School
4734083 Middle School
Unknown High School High School
See complete school information
Pricing History
DatePricePrice ChangeDescription
7/13/2026$2,390,000 Listed Price

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55 Winterset Drive, Chatham, MA, 02633 is a Single Family Home for sale at $2,390,000 with 4,066 sqft and a lot size of 1.94. 55 Winterset Drive has 4 bedrooms, 3.1 baths, and was built in 1970. The property's zip code is 02633 which is in Chatham, MA

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