143 Bayberry Way Osterville, MA $ 16,500,000
143 Bayberry Way
$ 16,500,000
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143 Bayberry Way

Osterville, MA, 02655
$ 16,500,000
Bedrooms8 Baths9.2 Sq 8,763

Monthly Estimate*

$ 104,183

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Single Family Home for sale in Osterville, MA

for $16,500,000 with 8 bedrooms and 9 full baths, 2 half baths. This 8,763 square foot home was built in 1914 on a lot size of 3.02.

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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Single Family Active

Price

$ 16,500,000

Bedrooms

8

Full Bath

9

Half Bath

2

Property Type

Single Family

Taxes

$ 78,577

Style

Colonial, Shingle

Lot Size

3.02

Year Built

1914

Town/City

Osterville

County/Region

Barnstable

MLS | Web ID

22605034

Features
General
Heating Natural Gas
Cooling Central Air
Roof Wood Shingle
Appliances Natural Gas Water Heater
Garage Spaces 2
Patio/Porch Features Patio
Architectural Style Colonial Shingle
Construction Materials Shingle Siding
Year Built 1914
Stories Count 3
Property Subtype Single Family Residence
Tax Year 2026
Waterfront Features Waterview Waterfront Bay/Harbor
County Barnstable
Property Type Residential
Attached Garage false
Garage Y/N true
Total Rooms 20
Full Baths 9
Status Active
Directions Wianno Avenue to Sea View Avenue to Bayberry Way.
City Osterville
Body of Water West Bay Salt
MLS Area Barnstable
Lot Size Units Acres
Lot Size Square Feet 131551
Tax Annual Amount 78577.66
Showing Instructions To schedule an appt. please call/text John Hopkins at 508-320-9461. 24-hour notice appreciated. No showings Friday Oct. 9th - Monday Oct. 12th.
Building Area Units Square Feet
Standard Status Active
Tax Assessed Value 9636700
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Interior
Interior Amenities Recessed Lighting Walk-In Closet(s)
Basement Finished Full
Flooring Wood Tile
Total Fireplaces 3
Air Conditioning Y/N true
Heating Y/N true
Half Baths 2
Total Bedrooms 8
Total Baths 11
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Exterior
Exterior Amenities Underground Sprinkler System
Parking Features Detached Garage Door Opener Driveway Gravel
Water Source Well Public
Lot Size Area 3.02
Building Area Total 8763
Lot Size Acres 3.02
Waterfront Y/N true
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* Excluded Features
List By
John J Hopkins

Listing Agent

Frank A Sullivan Real Estate

Broker

hop5jh@msn.com

Email

Affordability Calculator

$110,731
Per Month
94%
6%
0%
Monthly Principal & Interest
$104,183
Monthly Property Taxes
$6,548
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Pricing History
DatePricePrice ChangeDescription
10/2/2026$16,500,000 Listed Price

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143 Bayberry Way, Osterville, MA, 02655 is a Single Family Home for sale at $16,500,000 with 8,763 sqft and a lot size of 3.02. 143 Bayberry Way has 8 bedrooms, 9.2 baths, and was built in 1914. The property's zip code is 02655 which is in Osterville, MA