Raymond M. Hall, REALTOR® | Call | Text | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$16,500,000

143 Bayberry Way, Osterville, MA 02655

8 bedrooms 9 Full Baths 2 Half Baths 8,763 Sq Ft 3.02 acres 2 Car Garage
MLS# 22605034 · Residential / (Single Family Residence) · Osterville Waterfront
Listed: 10/02/26 (listing data as of 10/2/26 at 7:17 pm)
  • Finished Lower Level
  • Waterfront
  • Private Dock
  • Ch. 91 License
  • Water Views
  • Private Pool
  • Central A/C
  • 3 Fireplaces
  • Renovated 2014

About This Property

Set along the soothing waters of West Bay, this exceptional waterfront estate, with approx. 400' of waterfront, captures magnificent western exposure, offering ever-changing views of boats navigating to and from the harbor and spectacular evening sunsets dancing across the water. This 'Wianno Head' area is one of the most coveted areas of Osterville with large, private estate settings. This property also benefits from protected conservation 'Land Trust' land directly across from its gated entrance to the property. The main residence encompasses warm, luxurious living spaces, distinguished by extensive custom millwork, custom stone, tile and brick work, and refined architectural details throughout. The gourmet kitchen and butler's pantry are designed to delight, while the grand living room and adjoining dining room provide an elegant setting for entertaining. A sunroom overlooks the water, while the inviting family room and adjacent dining area create comfortable spaces for everyday living. The residence offers a 1st floor bedroom suite, and the 2nd floor provides three bedroom suites and a glorious master suite with his-and-her bathrooms and dressing rooms, a private sitting room, and a deck with exceptional water views. The third floor features an additional bedroom and bath, a family room, and a charming widow's walk overlooking the surrounding landscape and bay. A finished lower level provides additional flexible living and recreational space. A separate two-bedroom, two-bath carriage house offers a full kitchen and living room, providing an ideal private retreat for guests and extended family. Encompassing three acres of beautifully landscaped, park-like grounds, that are irrigated by a private well, the property offers an extraordinary sense of privacy. Manicured lawns and gracious mature trees frame an inviting PebbleTech-finish pool, an expansive terrace, perfectly suited for outdoor entertaining and enjoying unforgettable sunsets. Steps lead down to the water's edge, where a private sitting area provides a peaceful place to take in the views. A permanent deep-water dock on West Bay complete this remarkable waterfront setting. The prestigious Wianno Club and Oyster Harbors Club, as well as Nauticus Yacht Club, Crosby Boatyard, and the numerous shops and restaurants in the village, are only minutes away. All information stated here in or verbally stated, should be verified by the Buyer(s) and their representatives.

Property Details

Property TypeResidential
(Single Family Residence)
StatusFor Sale
MLS Number22605034
Year Built1914
Annual Taxes$78,578 (2026)
Total Assessment$9,636,700
Square Footage8,763
Price/Sq Ft$1883/sq ft
Additional Finished Space8,763 sqft
Lot Size3.02 acres
Total Rooms20
Bedrooms8
Full Baths9
Half Baths2
RenovatedYes
Year Renovated2014
Heat Source Forced Air, Natural Gas
Add'l Heating Forced Air
Cooling A/C Central Air
Garage Spaces2
Days on MarketLess than 24 hours
WaterfrontYes
Private Dock Yes, Ch. 91 License, Deep Water, Fixed
Private PoolYes
Private Pool Description Heated, In Ground
Water Body ViewWest Bay
Fireplaces3

Convenient To

  • Conservation Area
  • Golf Course
  • In Town Location
  • Marina
  • Shopping

Exterior Features

  • Private Yard
  • Underground Sprinkler System

Interior Features

  • Recessed Lighting
  • Walk-In Closet(s)

Location

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Listing Courtesy of: John J Hopkins / Frank A Sullivan Real Estate

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than John C. Ricotta & Associates are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 10/02/2026. Neither the listing broker nor John C. Ricotta & Associates shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.