55 Winterset Drive
Chatham, MA · $2,295,000
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55 Winterset Drive

Chatham, MA 02633
$2,295,000
83 days on market · Listed Oct 3, 2026
Data refreshed Oct 3, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
4
Baths
3.5
Sq Ft
4,066
Acres
1.94
Year Built
1970
$ / Sq Ft
$564
Days on Market
83

Investment Snapshot

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STR Range (P50)
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Location & Nearby

Map of 55 Winterset Drive, Chatham MA with nearby beaches and points of interest
HThis property
  • A
    🐟 White Pond
    0.56 mi
  • B
    🌲 Rolf E. Sylvan Gardens
    0.71 mi
  • C
    🚴 Old Colony Rail Trail - Chatham End
    0.78 mi
  • D
    🍽️ Branches Grill and Cafe
    0.80 mi
  • E
    🍽️ Pates Restaurant
    0.81 mi
  • F
    🍽️ Chatham Cheese Co
    0.85 mi
  • G
    🍽️ Del Mar Bar & Bistro
    0.85 mi
  • H
    🐟 White's Pond Public Swimming Area
    0.86 mi

About this property

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, 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 AC 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.

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Listed by Janet Stuart, Coldwell Banker Realty