153 Shore Road
Chatham, MA · $9,995,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

153 Shore Road

Chatham, MA 02633
$9,995,000
1 days on market · Listed Jul 22, 2026
Data refreshed Jul 22, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
3
Baths
2.5
Sq Ft
3,079
Acres
1.06
Year Built
1957
$ / Sq Ft
$3,246
Days on Market
1

Investment Snapshot

Monthly Carrying
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Cash Flow / yr
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Cash-on-Cash
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Cash Required
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Projected Revenue / yr
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Avg Daily Rate
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Occupancy
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STR Range (P50)
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Location & Nearby

Map of 153 Shore Road, Chatham MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ J. Bar
    0.23 mi
  • B
    🍽️ The Patio on Main
    0.24 mi
  • C
    🍽️ Cuvée at Chatham Inn
    0.24 mi
  • D
    🍦 Buffy's Ice Cream Cafe
    0.32 mi
  • E
    🍦 Brick Block Ice Cream and Crepe shop
    0.33 mi
  • F
    🍽️ Beach House Grill
    0.34 mi
  • G
    🍽️ Impudent Oyster
    0.34 mi
  • H
    🍦 Chatham Candy Manor
    0.36 mi

About this property

Shore Road is more than an address. It's a feeling. The moment you turn onto it, the mood quietly shifts. Clipped hedges, impossibly pretty gardens, sparkling water views, and the grand Chatham Bars Inn create a storybook setting. Offered for the first time in almost four decades, ''Offshore'' encompasses more than an acre on Shore Road - an exceptional combination of land, privacy, and possibility. Beyond the home's welcoming presence, a surprisingly private landscape unfolds, where mature plantings, a sweeping lawn, a carriage-style garage, and a swimming pool create an extraordinary retreat. Inside, the home was designed for gracious living, with spacious rooms and classic details, equally suited to entertaining or savoring a quiet afternoon. Views of Chatham Harbor, North Beach, and the Atlantic provide a lovely backdrop from the main living areas, while upstairs, charming windows frame picture-perfect coastal scenes. Whether enjoyed as it is today or reimagined, this is a rare opportunity to begin its next chapter. This special property invites its next owner to create a lasting legacy along one of Chatham's most iconic streets.

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📋 Chatham Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Chatham
Listed by Sarah Keith, eXp Realty,LLC