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55 Winterset Drive

Chatham, MA 02633
  • $2,390,000
  • STATUS: Active
  • ON SITE: 26 Days
  • MLS #: 22603375
UPDATED: 29 min ago
$2,390,000
  • 4
    BEDS
  • 1.94
    ACRES
  • 3
    BATHS
  • 1
    1/2 BATHS
  • 4,066
    SQFT
  • $588
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1970
County:
Area:

School Ratings & Info

School District:

Description

Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and 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. Home is being offered fully furnished if desired.

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Cape Cod & Islands MLS logo © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Rand Atlantic Cape Cod Realty. Data last updated: 2026-08-08T20:25:23.033.
www.randatlantic.com/homes/178749366
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55 Winterset Drive Chatham, MA 02633

  • Price: $2,390,000
  • Status: Active
  • On Site: 26 Days
  • Updated: 29 min ago
  • MLS #: 22603375
4
Beds
3
Baths
1
½ Baths
1.94
Acres
4,066
SQFT
$588
$/SQFT
1970
Built
Neighborhood:
Great Hills
County:
Barnstable
Area:
Chatham
School District:
Monomoy
Property Description
Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and 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. Home is being offered fully furnished if desired.
Exterior Features

Architectural Style Cape CodContemporary Carport No Construction Materials Shingle Siding Dock No Fencing Partial Foundation Details Poured Lot Features Bike PathSchoolMedical FacilityMajor HighwayHouse of WorshipNear Golf CourseCape Cod Rail TrailShoppingPublic TennisMarinaConservation AreaCul-De-Sac Open Parking No Parking Features Basement Parking Total 14 Patio And Porch Features DeckPatio Pool Private No Roof AsphaltShingle Water Front No Water View No

Interior Features

Appliances Gas Water Heater Attached Garage No Basement Yes Basement1 FinishedInterior EntryFull Cooling True Cooling Features Central Air Door Features French Fireplace YN Yes Fireplaces Total 4 Flooring HardwoodCarpet Garage Yes Heating Yes Heating Features Hot Water Interior Features Recessed Lighting Kitchen Dining Combo Yes Laundry Features Laundry RoomFirst Floor Living Dining Combo Yes Master Bedroom Level First Rooms Total 8

Property Features

Association Yes Association Fee 75 Association Fee Frequency Annually Flood Insurance Required Not Verified Flood Zone Not Applicable Improvement Assessments 1152900 Land Assessments 388000 Land Lease No Lead Paint Unknown Membership Required No Miles From Beach 0 - .1 New Construction No Nitrogen Sensitive Area No Other Assessments 0 Property Attached No Property Sub Type Single Family Residence Road Surface Type Paved Sewer Septic Tank Special List Conditions Standard Tax Annual Amount 5655 Tax Assessed Value 1540900 Tax Year 2026 Warranty Available False Water Source Well Year Built Description Updated/RemodeledActual Year Built Effective 2000 Year Round Yes Zoning R60

Cape Cod & Islands MLS logo Listing information © 2026 Cape Cod & Islands Multiple Listing Service, Inc.
Listing provided courtesy of Janet Stuart of Coldwell Banker Realty:


Cape Cod & Islands MLS logo © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Rand Atlantic Cape Cod Realty. Data last updated: 2026-08-08T20:25:23.033.
 
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229 Old Main Road
North Falmouth MA, 02556