55 Winterset Drive, Chatham, MA 02633

Chatham
Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
55 Winterset Drive,Chatham, MA 02633
$2,390,000
Virtual Tour
  • 4 Beds
  • 4 Baths
  • 4,066 sq. ft.
  • Single family
  • Active
Upcoming open houses
  • Fri, Jul 17
    03:30 pm - 05:00 pm
  • Sat, Jul 18
    10:00 am - 11:30 am
Listed by: janet stuart
Office: coldwell banker realty
MLS#:22603375
Source:CAPECOD

Price summary

  • Price:$2,390,000
  • Price per sq. ft.:$587.8
  • Monthly HOA dues:$6.25

About this home

Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover's Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & 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. Possible subdivision opportunity.

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Home facts

  • Year built:1970
  • Listing ID #:22603375
  • Added:3 day(s) ago
  • Updated:July 15, 2026 at 11:22 AM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:4
  • Rooms Total:8
  • Basement Description:Finished, Full, Garage Access, Interior Access, Walk-Out Access
  • Living area:4,066 sq. ft.

Heating and cooling

  • Cooling:Central Air

Structure and exterior

  • Year built:1970
  • Building area:4,066 sq. ft.
  • Lot area:1.94 Acres
  • Lot Features:Corner Lot
  • Construction Materials:Shingle Siding

Finances and disclosures

  • Price:$2,390,000
  • Price per sq. ft.:$587.8
  • Tax amount:$5,655

Features and amenities

  • Amenities:Central Vacuum, Recessed Lighting

Parking

  • Parking description:Direct Access, Garage Door Opener, Off Street, Paved
  • Garage spaces:2
MLS LogoDisclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Coldwell Banker Realty include the name of the listing broker. Neither the listing company nor Better Homes and Gardens Real Estate The Shanahan Group shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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