Raymond M. Hall, REALTOR® | Call | Text | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
This property was previously sold — it has since been re-listed. You are now viewing the current active listing.
$2,295,000
-4.0% from original list of $2,390,000 · September 11, 2026

55 Winterset Drive, Chatham, MA 02633

4 bedrooms 3 Full Baths 1 Half Bath 4,066 Sq Ft 1.94 acres 2 Car Garage
MLS# 22603375 · Residential / (Single Family Residence)
Listed: 07/12/26 (listing data as of 09/22/26 at 7:12 pm)
  • Hardwood Floors
  • Built-Ins
  • Cul-de-Sac
  • Kayaking
  • 1st Floor Primary Bedroom
  • Central A/C
  • 4 Fireplaces
  • Renovated 2000
  • 2-Car Garage

About This Property

Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central AC throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.

Property Details

Property TypeResidential
(Single Family Residence)
StatusFor Sale
MLS Number22603375
Year Built1970
Annual Taxes$5,655 (2026)
Total Assessment$1,540,900
Square Footage4,066
Price/Sq Ft$564/sq ft
Additional Finished Space700 sqft
Lot Size1.94 acres
Total Rooms8
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 Market72
WaterfrontNo
Miles to Beach0 - .1
Fireplaces4
Lot Features Corner Lot

Bedroom Details

Primary Bedroom

  • First Floor
  • Private Full Bath
  • Laundry Areas

Bedroom 2

  • Second Floor
  • Office/Sitting Area

Bedroom 3

  • Second Floor

Bedroom 4

  • Basement Floor

Living Area Details

Living Room

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

Dining Room

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

Kitchen

  • First Floor
  • French Door
  • Recessed Lighting
  • Kitchen Island
  • Wood Flooring
  • Granite Counters
  • Breakfast Bar

Laundry

  • 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

Sold History 55 Winterset Drive last sold April 10, 2023 for $1,770,000
Listed At $1,795,000
Sale / List 98.6%
Days on Market 2
View full sold details

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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 09/22/2026. 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.