Raymond M. Hall, REALTOR® | (508) 221-2544 | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$2,390,000

55 Winterset Drive, Chatham, MA 02633

4 Beds 3 Full Baths 1 Half Baths 4,066 Sq Ft 1.94 acres 2 Car Garage
MLS# 22603375 · Residential / (Single Family Residence)
Listed: 07/12/26 (listing data as of 07/30/26 at 3:50 pm)

About This Property

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.

Property Details

Property TypeResidential
(Single Family Residence)
StatusActive
MLS Number22603375
Year Built1970
Annual Taxes$5,655 (2026)
Total Assessment$1,540,900
Square Footage4,066
Price/Sq Ft$588/sq ft
Additional Finished Space700 sqft
Lot Size1.94 acres
Bedrooms4
Full Baths3
Half Baths1
RenovatedYes
Year Renovated2000
Heat Source Natural Gas
Add'l Heating Forced Hot Water
Cooling A/C Central Air
Association Fee $75.00 (Annually)
Association Fee Includes Beach Access
Garage Spaces2
Days on Market18
WaterfrontNo
Miles to Beach0 - .1
Fireplaces4
Lot Features Corner Lot

Bedroom Details

Primary Bedroom

  • First Floor
  • Closet
  • Laundry Areas
  • Private Full Bath

Bedroom 2

  • Second Floor
  • Closet
  • Office/Sitting Area

Bedroom 3

  • Second Floor
  • Closet

Bedroom 4

  • Basement

Living Area Details

Living Room

  • First Floor
  • Beamed Ceilings
  • Cathedral Ceiling
  • Wood Flooring
  • Recessed Lighting
  • Shared Half Bath
  • French Door Access

Dining Room

  • First Floor
  • Wood Flooring
  • Recessed Lighting
  • Shared Half Bath
  • French Door Access

Kitchen

  • First Floor
  • Breakfast Bar
  • Wood Flooring
  • Recessed Lighting
  • French Door Access

Laundry Room

  • First Floor

Convenient To

  • Bike Path
  • Cape Cod Rail Trail
  • Conservation Area
  • Golf Course
  • House of Worship
  • Major Highway
  • Marina
  • Medical Facility
  • Public Tennis
  • School
  • Shopping
  • Convenient to Lovers Lake
  • Convenient to Hardings Beach

Exterior Features

  • Private Yard

Interior Features

  • Central Vacuum
  • Recessed Lighting

Location

Nearby Listings

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Listing Courtesy of: Janet Stuart / Coldwell Banker Realty
The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than John C. Ricotta & Associates are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 07/30/2026. Neither the listing broker nor John C. Ricotta & Associates shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.