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55 Winterset Drive

Chatham, MA 02633
  • $2,495,000
  • STATUS: Active
  • ON SITE: 30 Days
  • MLS #: 22502257
UPDATED: 16 min ago
$2,495,000
  • 4
    BEDS
  • 1.94
    ACRES
  • 3
    BATHS
  • 1
    1/2 BATHS
  • 4,072
    SQFT
  • $613
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1970
County:
Area:

School Ratings & Info

School District:

Description

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. May be sold furnished.

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Cape Cod & Islands MLS logo © 2025 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: 2025-06-13T00:25:23.367.
www.randatlantic.com/homes/163778949
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55 Winterset Drive Chatham, MA 02633

  • Price: $2,495,000
  • Status: Active
  • On Site: 30 Days
  • Updated: 16 min ago
  • MLS #: 22502257
4
Beds
3
Baths
1
½ Baths
1.94
Acres
4,072
SQFT
$613
$/SQFT
1970
Built
Neighborhood:
Great Hills Estates
County:
Barnstable
Area:
Chatham
School District:
Monomoy
Property Description
Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. May be sold furnished.
Exterior Features

Carport No Construction Materials Shingle Siding Dock No Exterior Features Garden Fencing Fenced Foundation Details BlockSlab Lot Features Bike PathNear Golf CourseMarinaConservation AreaClearedEast of Route 6North of Route 28 Open Parking Yes Parking Features Basement Parking Total 6 Pool Private No Road Frontage Type Public Roof AsphaltPitchedFlat Water Front No Water View No

Interior Features

Appliances DishwasherWasherRefrigeratorMicrowaveGas Water Heater Attached Garage Yes Basement Yes Basement1 Bulkhead AccessInterior EntryFullFinished Cooling True Door Features French Entry Level 1 Entry Location First Floor Fireplace Features Wood Burning Fireplace YN Yes Fireplaces Total 4 Flooring HardwoodCarpetTileOther Garage Yes Heating Yes Heating Features Hot WaterOther Interior Features Recessed LightingPantryMud RoomLinen ClosetHU Cable TV Kitchen Dining Combo No Laundry Features Laundry RoomIn Basement Living Dining Combo No Master Bedroom Level First Rooms Total 8 Window Features Bay/Bow Windows

Property Features

Association Yes Association Fee 0 Association Fee Frequency Annually Community Features Deeded Beach Rights Elevation Certificate No Flood Insurance Required No Flood Zone X Improvement Assessments 1133300 Land Assessments 989600 Land Lease No Lead Paint Unknown Membership Required Unknown Miles From Beach 1 to 2 New Construction No Nitrogen Sensitive Area Yes Other Assessments 0 Property Attached No Property Sub Type Single Family Residence Road Surface Type Paved Sewer Private Sewer Special List Conditions None Tax Annual Amount 5179 Tax Assessed Value 2122900 Tax Book Number 35723 Tax Year 2025 Warranty Available False Year Built Description Updated/RemodeledActual Year Built Effective 1999 Year Round Yes Zoning R60

Cape Cod & Islands MLS logo Listing information © 2025 Cape Cod & Islands Multiple Listing Service, Inc.
Listing provided courtesy of Tara J Schiffmann of Bayview Real Estate:


Cape Cod & Islands MLS logo © 2025 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: 2025-06-13T00:25:23.367.
 
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229 Old Main Road
North Falmouth MA, 02556