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$2,390,000
New Listing

55 Winterset Drive
Chatham, MA 02633

For Sale|Single Family Residence|Active
4
Beds
4
Total Baths
3
Full Baths
1
Partial Bath
4,072
SqFt
$587
/SqFt
1970
Built
Subdivision:
Great Hill
County:
Barnstable

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55 Winterset Drive55 Winterset Drive55 Winterset Drive55 Winterset Drive
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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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Listing Snapshot
Price 
$2,390,000
Days On Site 
0 Days
Bedrooms 
4
Inside Area (SqFt) 
4,072 sqft
Total Baths 
4
Full Baths 
3
Partial Baths 
1
Lot Size 
1.94 Acres
Year Built 
1970
MLS® Number 
73548377
Status 
Active
Property Tax 
$5,655
HOA/Condo/Coop Fees 
$6.25 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
13 hours agoListing updated with changes from the MLS®
21 hours agoListing first seen on site
General Features
Acres 
1.94
Attached Garage 
Yes
Disclosures 
Potential to subdividebuyer to do due diligence.
Foundation 
Concrete Perimeter
Garage 
Yes
Garage Spaces 
2
Parking 
PavedOff StreetAttachedGarage
Parking Spaces 
14
Property Sub Type 
Single Family Residence
Security 
Security System
Sewer 
Private Sewer
SqFt Above 
3366
SqFt Below 
706
SqFt Total 
4072
Style 
CapeContemporary
Water Source 
Public
Zoning 
res
Interior Features
Appliances 
Gas Water HeaterOvenDishwasherMicrowaveRangeRefrigeratorWasherDryerWasher/Dryer
Basement 
FullFinishedWalk-Out AccessInterior Entry
Cooling 
DuctlessZoned
Electric 
200+ Amp Service
Fireplace 
Yes
Fireplaces 
4
Flooring 
TileCarpetHardwood
Heating 
Natural GasBaseboardZoned
Interior 
Master Downstairs
Window Features 
Insulated Windows
Bathroom 1 
Level - First
Bathroom 2 
Level - First
Bathroom 3 
Level - Second
Bedroom 2 
Level - Second
Bedroom 3 
Level - Second
Bedroom 4 
Level - Basement
Dining Room 
Level - First
Family Room 
Level - First
Kitchen 
Level - First
Living Room 
Level - First
Master Bedroom 
Level - First
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Exterior Features
Construction Details 
Frame
Lot Features 
Corner LotLandscaped
Patio And Porch 
DeckPatio
Roof 
Shingle
Windows/Doors 
Insulated Windows
Community Features
Association Dues 
75
Community Features 
Tennis Court(s)ParkGolf
HOA Fee Frequency 
Annually
Schools
School District
Unknown
Elementary School
Chatham
Middle School
Chatham
High School
Monomoy
Listing courtesy of Janet Stuart of Coldwell Banker Realty - Concord



The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords, and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Last checked 2026-07-12 05:31 PM UTC

Neighborhood & Commute
Source: Walkscore
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