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143 Bayberry Way

Osterville, MA 02655
  • $16,500,000
  • STATUS: Active
  • ON SITE: 12 Days
  • MLS #: 22605034
UPDATED: 33 min ago
$16,500,000
  • 8
    BEDS
  • 3.02
    ACRES
  • 9
    BATHS
  • 2
    1/2 BATHS
  • 8,763
    SQFT
  • $1,883
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1914
County:
Area:

School Ratings & Info

Description

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.

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Cape Cod & Islands MLS logo © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Rand Atlantic Cape Cod Realty. Data last updated: 2026-10-15T19:25:31.907.
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143 Bayberry Way Osterville, MA 02655

  • Price: $16,500,000
  • Status: Active
  • On Site: 12 Days
  • Updated: 33 min ago
  • MLS #: 22605034
8
Beds
9
Baths
2
½ Baths
3.02
Acres
8,763
SQFT
$1,883
$/SQFT
1914
Built
Neighborhood:
Barnstable
County:
Barnstable
Area:
Barnstable
Property Description
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.
Exterior Features

Architectural Style ColonialShingle Attached Garage YN No Construction Materials Shingle Siding Exterior Features Underground Sprinkler System Foundation Details Poured Garage YN Yes Parking Features DetachedGarage Door OpenerDrivewayGravel Patio And Porch Features Patio Private Dock Description Deep WaterCh. 91 LicenseFixed Private Pool Yes Private Pool Description HeatedIn Ground Roof WoodShingle Water Body View West Bay Waterview Description West Waterview Type Bay/Harbor

Interior Features

Appliances Natural GasWater Heater Basement FinishedFull Basement Description FinishedWalk-Out AccessFullInterior Access Cooling Central Air Cooling YN Yes Fireplaces Total 3 Flooring WoodTile Heat Forced Air Heating Natural Gas Heating YN Yes Interior Features Recessed LightingWalk-In Closet(s) Rooms Total 20

Property Features

Convenient To Conservation AreaIn Town LocationMarinaShoppingGolf Course FEMAFlood Zone X Golf Course Front No Golf Course View No Property Sub Type Single Family Residence Region Mid-Cape Renovated Yes Special Listing Conditions None Tax Annual Amount 78577.66 Tax Assessed Value 9636700 Tax Year 2026 Water Access Type Private Water Body Name West BaySalt Water Source WellPublic Waterfront Features WaterviewWaterfrontBay/Harbor Waterfront YN Yes Year Round Yes

Cape Cod & Islands MLS logo Listing information © 2026 Cape Cod & Islands Multiple Listing Service, Inc.
Listing provided courtesy of John J Hopkins of Frank A Sullivan Real Estate:


Cape Cod & Islands MLS logo © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Rand Atlantic Cape Cod Realty. Data last updated: 2026-10-15T19:25:31.907.
 
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