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255 Bayberry Way, Osterville, MA 02655

(Active)
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Listed by: Robert Kinlin - Berkshire Hathaway HomeServices Robert Paul Properties

255 Bayberry Way, Osterville, MA 02655

$
Active
est.$7,900,000/month.
7 beds. 6 baths. 260,489 Sqft.

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255 Bayberry Way, Osterville, MA 02655

$7,900,000
Active
est.$7,900,000/month.
7 beds 6 baths 260,489 Sq.ft.
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Property details for 255 Bayberry Way, Osterville, MA 02655
Welcome to ''Point House,'' an extraordinary 5.98-acre waterfront estate set on a private peninsula overlooking the shimmering waters of West Bay. Surrounded by breathtaking natural beauty, this rare offering pairs sweeping water views with exceptional privacy, highlighted by expansive lawns, curated gardens, a private sandy beach, and a substantial deep-water dock with direct access to Nantucket Sound. The nearly 5,000 square foot residence is thoughtfully designed to capture its remarkable setting, with six bedrooms, refined architectural detailing, custom millwork, and five fireplaces throughout. A gracious entry introduces uninterrupted water views and opens to an expansive deck spanning the length of the home--seamlessly blending indoor and outdoor living. At the heart of the home, a dramatic two-story great room with a floor-to-ceiling brick fireplace is bathed in natural light, while the well-appointed kitchen flows effortlessly into the dining area and inviting family room. Designed for both relaxed living and elegant entertaining, each space connects beautifully to the surrounding outdoor terraces. The first level also offers two bedrooms and a private sitting room, while the second floor is anchored by a serene primary suite with sweeping water views, a spacious bath, walk-in closet, and fireside sitting room. Three additional bedrooms and a secondary sitting area complete this level. A third-floor tower provides a stunning vantage point for panoramic sunsets over the bay. A detached two-car garage with guest accommodations above adds flexibility for extended family and visitors. Perfectly balancing seclusion and convenience, this exceptional coastal estate is just moments from Osterville Village's boutiques, dining, and charm. A truly rare opportunity to experience waterfront living at its finest.
Broker details: Berkshire Hathaway HomeServices Robert Paul Properties

Listed by: Robert Kinlin
Property Description

MLS Information

  • Listing: 22601177
  • Listing Last Modified: 2026-04-03

Property Details

  • Standard Status: Active
  • MLS Status: Active
  • Property style: Contemporary
  • Built in: 1988
  • Lot size area: 5.98 Acres

Geographic Data

  • County: Barnstable
  • Directions: Sea View Avenue to Bayberry Lane to the end
Features

Interior Features

  • Flooring: Vinyl, Carpet, Tile, Wood
  • Bedrooms: 7
  • Full baths: 6
  • Interior Features: Wet Bar, Recessed Lighting, Pantry, Walk-In Closet(s)
  • Fireplaces: 5

Exterior Features

  • Roof type: Shingle
  • Lot description: On Golf Course, Near Golf Course, Cleared, Waterfront
  • View: Water, Bay

Parking

  • Garage spaces: 2

Utilities

  • Sewer: Private Sewer
Property Information

Tax Information

  • Tax Annual Amount: $78,869

Disclaimer

The property listing data and information 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 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 set forth herein.

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Home Description

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