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 4,072 Sq Ft 1.94 acres 2 Car Garage
MLS# 22603375 · Residential / (Single Family Residence)
Listed: 07/12/26 (listing data as of 11/6/26 at 9:59 pm)
Open
Houses:
Saturday, November 7

11:00 am - 1:00 pm

Sunday, November 8

11:00 am - 1:00 pm

  • Hardwood Floors
  • Primary Suite
  • Laundry Room
  • Kayaking
  • 1st Floor Primary Bedroom
  • Central A/C
  • 4 Fireplaces
  • Renovated 2000
  • 2-Car Garage

About This Property

Exceptional Great Hill Estates retreat being offered fully furnished, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short foot path away. Located on a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out. A first-floor primary suite features ensuite bath and laundry for convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent great rooms with vaulted beamed ceilings and fireplaces. A wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs are two bedrooms and a full bath, including one bedroom with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, another laundry area, and direct access to a stone patio with custom seating and gas fire pit. Additional highlights include central ac, hardwood floors, two-car attached garage and new Bosch heating system. Close to Chatham Village, Lighthouse and Hardings beaches, bike path and tennis courts.

Property Details

Property TypeResidential
(Single Family Residence)
StatusFor Sale
MLS Number22603375
Year Built1970
Annual Taxes$5,655 (2026)
Total Assessment$1,540,900
Square Footage4,072
Price/Sq Ft$564/sq ft
Additional Finished Space706 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 Market117
WaterfrontNo
Miles to Beach0 - .1
Fireplaces4
Lot Features Corner Lot

Bedroom Details

Primary Bedroom

  • First Floor
  • Closet(s)
  • Laundry Areas
  • Private Full Bath

Bedroom 2

  • Second Floor
  • Closet(s)
  • Office/Sitting Area
  • Wood Burning Fireplace

Bedroom 3

  • Second Floor
  • Closet(s)

Bedroom 4

  • Basement Floor
  • Closet(s)

Living Area Details

Living Room

  • First Floor
  • Beamed Ceilings
  • French Door
  • Gas Fireplace
  • Hardwood Flooring
  • Recessed Lighting

Dining Room

  • First Floor
  • French Door
  • Hardwood Flooring
  • Recessed Lighting

Kitchen

  • Granite Counters
  • Hardwood Flooring
  • Recessed Lighting

Laundry

  • Basement Floor

Family Room

  • First Floor
  • Beamed Ceilings
  • Ceiling Fan(s)
  • Hardwood Flooring
  • Wood Burning Fireplace

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 11/06/2026. 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.