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For SaleWaterfrontMLS# 22605034

143 Bayberry Way

Osterville, MA 02655
$16,500,000
8Beds
11Baths
8,763Sq Ft
2 carGarage
3.02 acres · Built 1914
Waterfront· Waterview, Waterfront, Bay/Harbor

Home For Sale in Osterville, MA

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 Type
Single Family Residence
Style
Colonial, Shingle
Year Built
1914
Bedrooms
8
Bathrooms
9 full · 2 half
Sq Footage
8,763
Lot / Acres
3.02 acres
County
Barnstable
Rooms Total
20
Stories
3
Garage
2 car
Basement
Finished, Full
Flooring
Wood, Tile
Fireplace
3
Roof
Wood, Shingle
Construction
Shingle Siding
Waterfront
Yes
Annual Taxes
$78,577.66
Tax Year
2026
Assessed Value
$9,636,700

Features & Amenities

Natural Gas
Water Heater
Recessed Lighting
Walk-In Closet(s)
Underground Sprinkler System
Patio

Interior Details

Appliances
Natural Gas, Water Heater
Interior Features
Recessed Lighting, Walk-In Closet(s)

Exterior & Location Details

Exterior Features
Underground Sprinkler System
Patio / Porch
Patio
Directions
Wianno Avenue to Sea View Avenue to Bayberry Way.

Listed by: John J Hopkins from Frank A Sullivan Real Estate

© 2026 Cape Cod & Islands Multiple Listing Service. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of CCIMLS. Information provided is deemed reliable but not guaranteed.

Location

143 Bayberry Way

Osterville, MA 02655

Open in Google Maps
Bridget Houlihan
Bridget Houlihan
Wood Real Estate

Water Features

Waterfront

Yes

Waterfront Features

Waterview, Waterfront, Bay/Harbor

Water Body Name

West Bay,Salt

Listing Details

MLS #22605034
StatusActive
List Price$16,500,000
Lot Size3.02 acres
Year Built1914

About Osterville

Median Price
$1.45M
Avg Days on Market
38
Explore Osterville
CCIMLS Data Distribution

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. Summary or thumbnail real estate listings held by brokerage firms other than Wood Real Estate, Inc. are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Wood Real Estate, Inc. 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.