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143 Bayberry Way Osterville MA 02655 | MLS #22605034

143 Bayberry Way
Osterville, MA, 02655
$16,500,000
8 Beds
10 Baths
8,763 SqFt
3.02 Acres
MLS #22605034 image #0
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

Price:
$16,500,000
MLS #:
22605034
Status:
Active
Beds:
8
Baths:
10
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
barnstable
Listed Date:
Oct 2, 2026
Finished Sq Ft:
8,763
Total Sq Ft:
8,763
Lot Size:
131,551 sqft / 3.02 acres (approx)
Year Built:
1914
WaterfrontOceanviewBarnstableBarnstableBarnstableWest Bay,saltOcean

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Schools

School District:
Barnstable

Interior

Appliances
Natural Gas, Water Heater
Bathrooms
9 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Fireplaces Total
3
Flooring
Wood, Tile
Heating
Natural Gas
Interior Features
Recessed Lighting, Walk-In Closet(s)

Exterior

Architectural Style
Colonial, Shingle
Construction Materials
Shingle Siding
Exterior Features
Underground Sprinkler System
Garage Spaces
2
Parking Features
Detached, Garage Door Opener, Driveway, Gravel
Patio And Porch Features
Patio
Roof
Wood, Shingle
Stories
3
Waterfront Features
Waterview, Waterfront, Bay/Harbor

Financial

Tax Year
2026
Taxes
$78,578

Map

Community

Market Summary

Current real estate data for Single Family in Osterville as of Oct 10, 2026
47
Single Family Listed
125
Avg DOM
1,004
Avg $ / SqFt
$4,919,026
Avg List Price

Property Summary

    143 Bayberry Way Osterville MA is a Single Family for sale in Osterville, MA, 02655. It is listed for $16,500,000 and features 8 beds, 10 baths, and has approximately 8,763 square feet of living space, and was originally constructed in 1914. The current price per square foot is $1,883. The average price per square foot for Single Family listings in Osterville is $1,004. The average listing price for Single Family in Osterville is $4,919,026. To schedule a showing of MLS#22605034 at 143 Bayberry Way in Osterville, MA, contact your Gibson Sotheby’s Int’l Realty agent at 5084327856.

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143 Bayberry Way
Osterville, MA