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Listing broker remarks

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, an 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 air conditioning 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.— Coldwell Banker Realty - Concord

Key details

  • 4,072 sq ft
  • 1.94 acres
  • 4 beds
  • 3.5 baths
  • 1970 built
  • $563 / sq ft
  • $5,655 2026 taxes
  • HOA yearly
MLS #
7⁠3⁠5⁠4⁠8⁠3⁠7⁠7⁠
Last updated
Address
55 Winterset Drive
Town
Chatham, MA
ZIP
02633
Deed (Bk/Pg)
20038 / 79

Map

Neighborhood: Great Hill

National Historic Landmark

Federally designated as nationally significant — the highest U.S. historic recognition. Section 106 review applies to federal undertakings affecting the property.

National Register

Listed on the National Register of Historic Places. Owners may qualify for the 20% federal Historic Rehabilitation Tax Credit on certified rehabilitation work.

State Register

Listed on the Massachusetts State Register of Historic Places.

Local Historic District

Inside a Local Historic District. Exterior changes visible from a public way require approval from the local historic district commission.

Local Landmark

Individually designated by the town as a local landmark. Exterior alterations require commission approval.

MACRIS Inventory

Documented in MACRIS, the state historic inventory. Informational only — no regulatory constraints.

Article 85 (Boston)

Subject to Boston Article 85 demolition-delay review, which can pause demolition of buildings 50+ years old for up to 90 days.

Ch. 91 Waterways License

An active MassDEP permit for a dock, pier, seawall, or other structure on or over a Massachusetts waterway. Many older licenses are not digitized; this record is provided for reference only.

Massachusetts Great Pond

A Great Pond under M.G.L. Ch. 91 — the Commonwealth retains public rights to fish and navigate these state-designated waters. Private docks and other waterfront structures require a Waterways License from MassDEP.

Likely Great Pond

The MLS listing describes this property as being on a Great Pond, which would be a state-designated water body under M.G.L. Ch. 91. GIS data did not independently confirm the pond name — verification needed.