$5,750,000
58 Oyster Bluff
Chatham, MA, 02633
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 .93-acre parcel with expansive frontage, it captures sweeping views of town and Oyster Pond, a lifestyle both connected and secluded. Originally built in Wellfleet as the Captain Holbrook House, it has been preserved and expanded over generations while modernized for gatherings. Seven bedrooms include a first-floor primary suite, while a Good Morning staircase with a hand-painted Chatham mural leads to additional bedrooms. Historic character endures throughout: the celebrated wood room with elements from the Plymouth Cordage Co. ropewalk (c.1824), hand-hewn beams, herringbone brick floors, central hearths, and built-ins. Outside, brick patios, sycamore trees, granite steps, and rock walls frame lawns rolling to the water’s edge, where a private catwalk and moorings await. A legacy property, ready for its next steward.
Property Details
Price:
$5,750,000
MLS #:
73421848
Status:
Pending
Beds:
7
Baths:
3.5
Address:
58 Oyster Bluff
Type:
Single Family
Subtype:
Single Family Residence
City:
Chatham
Listed Date:
Aug 25, 2025
State:
MA
Finished Sq Ft:
3,734
Total Sq Ft:
3,734
ZIP:
02633
Lot Size:
40,510 sqft / 0.93 acres (approx)
Year Built:
1930
Schools
Interior
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
None
Fireplaces Total
4
Heating
Central, Natural Gas
Exterior
Architectural Style
Cape
Parking Spots
6
Financial
Tax Year
2025
Taxes
$15,095
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
58 Oyster Bluff
Chatham, MA
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