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255 Bayberry Way
Osterville MA 02655 US

$7,900,000

Active Listing ID 22601177
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7 bed
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6.00 Bath (6 Full)
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Lot: 5.98 Acres
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Single Family Residence

$7,900,000

Active Listing ID 22601177
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255 Bayberry Way 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.

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Property Features

  • Facts
  • Lot Size: 5.98 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 6
  • Cooling System: Central Air
  • Exterior Finish: Underground Sprinkler System, Private Yard, Outdoor Shower, Garden
  • Floor Covering: Tile, Carpet, Vinyl, Wood
  • Roof Type: Shingle
  • Heating Fuels: Propane (Heating), Forced Air
  • Additional Features
  • Basement
  • Fireplace
  • Patio
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 7900000
  • unparsedaddress: 255 Bayberry Way
  • postalcity: Osterville
  • stateorprovince: MA
  • country: US
  • postalcode: 02655
  • bathroomsfull: 6
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 5.98
  • lotsizeunits: Acres
  • lotsizearea: 5.98
  • livingarea: 4896
  • livingareaunits: Square Feet
  • latitude: 41.614899
  • longitude: -70.395513
  • listagentfullname: Robert B Kinlin
  • listagentemail: rkinlin@robertpaul.com
  • listagentkey: 3yd-CCIAORMA-U0Y3
  • listagentmlsid: U0Y3
  • listagentpreferredphone: 5084201414
  • listagentofficephone: 5084201414x204
  • listofficekey: 3yd-CCIAORMA-CENCOM2
  • listofficemlsid: CENCOM2
  • disclaimer: Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: CCIAORMA
  • yearbuilt: 1988
  • listingcontractdate: 2026-04-03
  • listagentfax: 5084207114
  • countyorparish: Barnstable
  • parcelnumber: OSTE M:092 L:001
  • elementaryschooldistrict: Barnstable
  • middleorjuniorschooldistrict: Barnstable
  • highschooldistrict: Barnstable
  • appliances: Water Heater, Wine Cooler, Washer/Dryer Stacked, Range Hood, Gas Range, Countertop Range, Dishwasher, Freezer, Indoor Grill, Microwave, Refrigerator, Wall/Oven Cook Top, Washer
  • cooling: Central Air
  • constructionmaterials: Clapboard
  • flooring: Tile, Carpet, Vinyl, Wood
  • heating: Propane (Heating), Forced Air
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 5
  • parkingfeatures: Open, Off Street
  • roof: Shingle
  • view: Harbor
  • waterfrontyn: True
  • franchiseaffiliation: None
  • interiorfeatures: Walk-In Closet(s), Linen Closet, Pantry, Recessed Lighting, Wet Bar, Kitchen Island
  • exteriorfeatures: Underground Sprinkler System, Private Yard, Outdoor Shower, Garden
  • rooms: Bedroom 7, Bathroom 6, Bedroom 2, Bedroom 3, Bathroom 3, Dining Room, Bathroom 5, Bathroom 1, Bathroom 2, Bedroom 4, Bedroom 5, Basement, Bathroom 4, Bedroom 1, Bedroom 6
  • securityfeatures: Security System
  • otherstructures: Guest House
  • patioandporchfeatures: Patio, Porch, Deck
  • basement: Walk-Out Access, Full
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -70.395515, 41.6149
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Robert Paul Properties, Inc.", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"rkinlin@robertpaul.com", "ListBrokerageCity":"Sandwich", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"Robert Paul Properties, Inc.", "ListBrokeragePhone":"(508) 863-4663", "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"MA", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"68 Tupper Road, Unit 7", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"867 Main Street ", "ListOfficeAddress2":"", "ListOfficeBrokerMlsId":"CENCOM2", "ListOfficeCity":"Osterville", "ListOfficeCountry":"USA", "ListOfficeEmail":"jsullivan@robertpaul.com", "ListOfficePostalCode":"02655", "ListOfficeStateOrProvince":"MA", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Osterville, MA", "ListingURL":null, "MLSModificationTimestamp":"2026-04-03 13:41:33", "Neighborhoods":[{"Description":null, "Name":"Barnstable"}], "PostalCode":null, "RoomCount":9, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":78869, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 4/3/2026 1:45:42 PM GMT
Source Updated Date: 4/8/2026 12:58:13 PM GMT

Courtesy of: Robert B Kinlin, Berkshire Hathaway HomeServices Robert Paul Properties, rkinlin@robertpaul.com

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.