Perched high above Oyster Pond, this generational estate-first

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Home Sale Pending

58 Oyster Bluff

Chatham, Massachusetts 02633

Barnstable County

Waterfront: Yes

Community: 

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$5,750,000 7 br, 0.0 bath 3734 sq. ft. 0.930 acres

Perched high above Oyster Pond, this generational estate-first known as ''The Beach Plum House'' and later as ''Adsamore''-is one of Chatham's rarest offerings. Set on a remarkable .93-acre parcel with expansive frontage, it offers sweeping views of town and Oyster Pond, a lifestyle at once connected and secluded. Originally built in Wellfleet as the Captain Holbrook House, the home has been lovingly preserved and expanded over time while being modernized for hosting and gathering. The seven bedrooms include a private first-floor primary suite with walk-in closet and ensuite bath, while a Good Morning staircase, adorned with a hand-painted Chatham mural, leads to the upper level bedrooms. Historic character endures throughout: the wood room with elements from the Plymouth Cordage Co. ropewalk (circa 1824), hand-hewn structural beams, herringbone brick floors, central hearths, and authentic built-ins. Outside, brick patios, mature sycamore trees, granite steps, and rock walls frame rolling lawns that meet the water's edge, where a private catwalk and moorings await. Spacious yet intimate, this is a true legacy property-an irreplaceable waterfront setting ready for its next steward.

Interior:
  • Bedrooms: 7
  • Baths: 0.0
  • Sq Ft: 3734
  • Year Built: 1930
  • Utilities: 
  • Fireplaces: 
  • Stories: 2
  • Heat/AC: Natural Gas
  • Garage: 
Exterior:
  • Lot Size: 0.930 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: Lake
  • Yard: 
  • Siding: Clapboard
  • Roof: Asphalt
  • Property Taxes: $15,095
  • MLS #: 22504136
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Contact Information:
Beach Home Sale Pending in Chatham, Massachusetts
Listing Agent: Guthrie Schofield Group, Robert Paul Properties, Inc., 774-487-8554, 508-945-5553 Listing Site, Listing Status: Pending
Copyright © 2025 Cape Cod & Islands Association of REALTORS®, Inc.. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 6554040
Viewed 67 times.
Updated: Oct 15, 2025

This property is a Home located at 58 Oyster Bluff, Chatham, Massachusetts 02633, and is currently Sale Pending at $5,750,000. This Home has 7 bedrooms, 0.0 baths, 3734 sq ft.