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Single family home for sale at 143 Bayberry Way, Osterville, MA 02655 | MLS# 73586293 | Listing updated on 2026-10-03
Photo 1 of Single family home for sale at 143 Bayberry Way, Osterville, MA 02655 | MLS# 73586293 | Listing updated on 2026-10-03
Photo 2 of Single family home for sale at 143 Bayberry Way, Osterville, MA 02655 | MLS# 73586293 | Listing updated on 2026-10-03
Photo 3 of Single family home for sale at 143 Bayberry Way, Osterville, MA 02655 | MLS# 73586293 | Listing updated on 2026-10-03
Photo 4 of Single family home for sale at 143 Bayberry Way, Osterville, MA 02655 | MLS# 73586293 | Listing updated on 2026-10-03
38+
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Street View

$16,500,000

Monthly Est:$82,126

  • Beds Icon8 Beds
  • Beds Icon
    11 Baths
  • Beds Icon8,763sqft

143 Bayberry Way, Osterville, MA 02655

$82,126/moEst:

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  • Single Family Residence

  • Built in 1914

  • $-- HOA

  • 3.02 acres lot

  • $1,883/sq.ft

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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: October 3, 2026 at 7:06 pm
  • Listing Provided by: John Hopkins (508) 320-9461 | Frank Sullivan Real Estate, LLC (508) 428-4400
  • Source: MLS Property Information Network-MA | MLS#: 73586293 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Barnstable County

  • City

    Osterville

  • Neighborhood

    --

  • Year Built

    1914

  • HOA Fees

    -

  • Finished Area

    8,763 sqft

  • Lot Size

    3.02 acres lot

  • Basement Area

    - sqft

  • MLS Name

    MLS Property Information Network

  • MLS Number

    73586293

  • MLS Status

    New

  • Days on Market

    1

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 8

    Bathrooms: 11

Interior

  • Heating

    Forced Air, Natural Gas

  • Flooring

    Wood

  • Sewer

    Private Sewer

  • Exterior Features

    Patio, Pool Inground Heated, Sprinkler System, Guest House

  • Cooling

    Central Air

  • Appliances

    Water Heater

Construction

  • Year Built

    Year Built: 1914

  • Home type

    Single Family Residence

  • Roof

    Wood

  • Architectural Style

    Colonial

  • Construction Materials

    Frame

  • Foundation Details

    Concrete Perimeter

Utilities & Energy

  • Pool Features

    Pool Inground Heated

  • Security Features

    Security System

  • Basement

    Full, Partially Finished, Walk Out Access

  • Parking Features

    Detached, Garage Door Opener

  • Water Source

    Public, Private

Other Features

  • Community Features

    Shopping, Golf, Conservation Area, Marina

  • Patio And Porch Features

    Patio

Price History

DateEventPrice

10/02/2026

Source: mls_logoCape Cod And Islands MLS-MA #22605034

Listed for Sale

$16,500,000

$1,883/sqft

Nearby Homes

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 02, 2026, 09:00AM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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