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
1 days on market · Listed Jul 11, 2026
Data refreshed Jul 12, 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
1

Investment Snapshot

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