55 Winterset Drive
Chatham, MA · $2,390,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

55 Winterset Drive

Chatham, MA 02633
$2,390,000
45 days on market · DEL → ACT on Aug 24, 2026
Data refreshed Aug 25, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
4
Baths
3.5
Sq Ft
4,072
Acres
1.94
Year Built
1970
$ / Sq Ft
$587
Days on Market
45

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
    0.57 mi
  • B
    🌲 Rolf E. Sylvan Gardens
    0.71 mi
  • C
    🚴 Old Colony Rail Trail - Chatham End
    0.77 mi
  • D
    🍽️ Branches Grill and Cafe
    0.80 mi
  • E
    🍽️ Pates Restaurant
    0.82 mi
  • F
    🍽️ Del Mar Bar & Bistro
    0.85 mi
  • G
    🍽️ Chatham Cheese Co
    0.85 mi
  • H
    🍽️ Pain d’Avignon Restaurant Boulangerie
    0.86 mi

About this property

Spectacular four bedroom home set on almost two acres in sought-after Great Hill. Enjoy breezy nights and summer days with deeded rights to 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, four fireplaces, open floor plan and wraparound decks with elevated views of the expansive property, all perfect for entertaining and large family gatherings. The first floor has two large great rooms with soaring beamed ceilings and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.

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📋 Chatham Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Chatham
Listed by Janet Stuart, Coldwell Banker Realty - Concord