Sign up to get new listings emailed daily! JOIN SIGN IN
Ellen Clancy
REALTOR®
VCard Icon 

55 Winterset Drive, Chatham, MA 02633

$2,390,000
  • Main Photo

42 Total Photos [Click to View All]

Active
BEDS4 BATHS3 full 1 partial SQUARE FEET4,072 MLS#73548377
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONGreat Hill

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.

55 Winterset Drive | MLS# 73548377

This single family home located at 55 Winterset Drive, Chatham, MA 02633 is currently listed for sale with an asking price of $2,390,000. This property was built in 1970 and has 4 bedrooms and 3 full and 1 partial baths with 4072 sq. ft. Winterset Drive is located in the Great Hill subdivision. Search Great Hill real estate on ellenclancy.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Full, Finished, Walk-Out Access, Interior Entry, Garage Access
Basement: Yes
Cooling: Central Air, Ductless
Fireplaces: 4
Garage: 2 car attached
Heating: Baseboard, Natural Gas
Home Style: Cape, Contemporary
Lot Size: 1.94 Acres
Roof Type: Shingle
Taxes: $5,655
Year Built: 1970

Amenities

Bathroom
Deck
Patio
Professional Landscaping
Outdoor Gas Grill Hookup

Feature Descriptions

Appliances: Gas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer, Washer/Dryer
Association Fee: $75/Annually
Building Area Total: 4072
Community Features: Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Public School
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 10
Door Features: Insulated Doors, French Doors
Electric: 200+ Amp Service
Exterior: Frame
Fireplace Y/N: Yes
Flooring: Tile, Carpet, Hardwood
GarageY/N: Yes
HeatingY/N: 1
HOA Y/N: Yes
Laundry: First Floor, Gas Dryer Hookup
Lot Features: Corner Lot
Master Bathroom: Yes
Open Parking Y/N: Yes
Parcel Number: 2260871
Parking Features: Attached, Under, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street
Parking Total: 14
Patio And Porch: Deck, Patio
Rooms Total: 8
Security: yes
Security Features: Security System
Sewer: Private Sewer
Utilities: for Gas Range, for Gas Dryer, Outdoor Gas Grill Hookup
Water: Public
Waterfront Features: Lake/Pond,0 to 1/10 Mile To Beach, Beach Ownership(Private)
Window Features: Insulated Windows

Local Schools

High School: Monomoy
Middle School: Chatham
Elementary School: Chatham

Listed By / Shown By

Listed By

Agency Name: Coldwell Banker Realty - Concord
Agent Name: Janet Stuart
Agency Phone: 978-369-1000

IDX logo

TOUR THIS HOME

Choose a date and time to see 55 Winterset Drive, Chatham, MA 02633.
I will get in touch with you shortly.

Request a Showing
Choose your video chat app
  • Wednesday July 22
  • Thursday July 23
  • Friday July 24
  • Saturday July 25
  • Sunday July 26
  • Monday July 27
  • Tuesday July 28
  • Wednesday July 29
  • Thursday July 30
  • Friday July 31
  • Saturday August 1
  • Sunday August 2
  • Monday August 3
  • Tuesday August 4
  • Wednesday August 5
  • 7:00 AM
  • 7:30 AM
  • 8:00 AM
  • 8:30 AM
  • 9:00 AM
  • 9:30 AM
  • 10:00 AM
  • 10:30 AM
  • 11:00 AM
  • 11:30 AM
  • 12:00 PM
  • 12:30 PM
  • 1:00 PM
  • 1:30 PM
  • 2:00 PM
  • 2:30 PM
  • 3:00 PM
  • 3:30 PM
  • 4:00 PM
  • 4:30 PM
  • 5:00 PM
  • 5:30 PM
  • 6:00 PM
  • 6:30 PM
  • 7:00 PM
  • 7:30 PM
  • 8:00 PM
  • 8:30 PM
  • 9:00 PM
Preferred Communication Method

Estimate Your Payment

Estimated Payment

$ 6,487.44 per month $5,319.10 Principal & Interest $471.25 Property Tax $697.08 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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 on this site was last updated 07/21/2026. The listing information on this page last changed on 07/21/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 07/21/2026 6:55:10 AM EST) or MLSPIN MLS (last updated Mon 07/20/2026 11:38:26 PM EST) or Prime MLS (last updated Mon 07/20/2026 11:33:29 PM EST) or MREIS (last updated Tue 07/21/2026 2:05:12 AM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility

Agency License Information: Better Homes and GardensĀ® and the Better Homes and Gardens Real Estate Logo are registered service marks owned by Meredith Corporation and licensed to Better Homes and Gardens Real Estate LLC. The Masiello Group Limited fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC nor any of its affiliated companies.


Login to My Homefinder

Pixel