For Sale

Listed by Tara Schiffmann from Bayview Real Estate

Source: Cape Cod & Islands Association of REALTORS #22502257

55 Winterset Dr, Chatham, MA, 02633

$2,295,000

4
4
6
4072 sq. ft.
82328 sq. ft.

SingleFam

30+ days on the market

What's around 55 Winterset Dr

About this property

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham's bustling village & ocean beaches. New flat partial Roof & Boiler

Looking for more information on 55 Winterset Dr?

Explore comparables, sales history and growth for this property.
Learn more

Similar properties for sale nearby

For Sale
$4,495,000
335 Stage Island Rd
Chatham MA 02633
4
6
6
Single-Family
Listing courtesy of Gibson Sotheby's International Realty
For Sale
$1,800,000
213 Main Street
Chatham MA 02633
4
2
3
Single-Family
Listing courtesy of Gibson Sotheby's International Realty
For Sale
$3,600,000
60 Harbor Hill Rd
Chatham MA 02633
4
4
6
Single-Family
Listing courtesy of Shore Road Realty, LLC

Other properties for sale by Bayview Real Estate

For Sale
$830,000
16 Old Toll Rd
Barnstable Town MA 02668
3
3
3
Single-Family
Listing courtesy of Bayview Real Estate
For Sale
$1,825,000
46 Main Street
Yarmouth Port MA 02675
3
3
1
Single-Family
Listing courtesy of Bayview Real Estate

Browse properties sold in nearby areas

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent