255 Bayberry Way

4,896 Sq. Ft.
$1,614 / Sq. Ft.
4,896
Sq. Ft.
$1,614
per Sq. Ft.

Description

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,...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
  1. Listed by Robert B Kinlin • Berkshire Hathaway HomeServices Robert Paul Properties • rkinlin@robertpaul.com

Property Details for 255 Bayberry Way

Village
Osterville
School District
Barnstable
Style
Garden, Contemporary
Waterfront Type
Bay/Harbor
Waterview Type
Bay/Harbor
Waterfront
Yes
Waterview
Yes
Num Parking Spaces
5.00
LISTING UPDATED: 04/25/2026 12:12 PM

Property Details for 255 Bayberry Way

StatusActive
MLS #22601177
Days on Market37
Taxes$78,869 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeSingle Family / Single Family Residence
Year Built1988
Lot Size5.98 AC / 260,489 SF
CountyBarnstable County

Location

Listing Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties, Robert B Kinlin
Add your commute

Building Information for 255 Bayberry Way

Stories2Year Built1988Building Size-Lot Size5.98 AC / 260,489 SF

Payment Calculator

$46,353 per month

30 year fixed, 6.46% Interest

Principal and Interest

$39,781

Property Taxes

$6,572

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 255 Bayberry Way

Summary
Location and General Information
  • Directions to Property: Sea View Avenue to Bayberry Lane to the end
  • Convenient To:Golf Course: Yes
  • Convenient To:House of Worship: Yes
  • Convenient To:Marina: Yes
  • Convenient To:School: Yes
  • Convenient To:Shopping: Yes
  • Convenient To:Convenient to Water Body 1: West Bay
  • Convenient To:Convenient to Water Body 2: Nantucket Sound
  • Region: Mid-Cape
  • County: Barnstable
  • City Postal ID: 02655
  • Street Number: 255
  • Water Body Name: West Bay
  • MLSAreaMajor: Barnstable
  • General Property Info:Water Body: West Bay
Parking
  • Garage: Yes
  • Garage Description:Detached: Yes
  • Garage Description:Door Opener: Yes
  • Parking Description:Off-Street: Yes
  • Parking Description:Stone/Gravel: Yes
  • Carport: No
  • Garage Spaces: 2.00
Taxes and HOA Information
  • Tax Year: 2026
  • Annual Assoc Fee: $0
  • Annual Taxes: $78,869
Virtual Tour
  • Virtual Tour YN: No
Property
Lot Information
  • Zoning: RF-1
  • Tax ID: OSTE M:092 L:001
  • Lot Size Source: Assessor
  • TopographyLot Desc:View: Yes
  • TopographyLot Desc:Cleared: Yes
  • Land Use: 101 - Residential, single family
  • Lot Size Square Feet: 260489
  • Sqft Total: 4896
  • Field Card SqFt: 4896
  • Lot Size Units: Acres
  • Living Area: 4896.0
  • General Property Info:Leased Land: No
Property and Assessments
  • Total Assessment: $9,672,500
  • Land Assessments: $7,181,900
  • Building Assessments: $2,490,600
  • Other Assessments: $0
  • Renovated: No
  • Flood Ins Required: Yes: verify w/insurance agent
  • Lead Base Paint: Unknown
  • Year Round: Yes
  • Landlord Pays:Sewer: Private Sewerage
  • Year Built Desc:Actual: Yes
  • Property Type: Residential, Single Family Residence
  • Property Subtypes: Single Family Residence
  • Year Built Numeric: 1988
  • Construction Materials: Clapboard
  • Property Type: Residential
  • Property Attached: No
  • Senior Community: No
Utilities
  • Cooling: Central Air
  • Fuel Type:Electric: Generator Connection
  • Fuel Type:Propane Gas: Yes
  • Hot Water:Tank: Yes
  • Hot Water Source:Propane Gas: Yes
  • Sewer:Private Sewer: Yes
  • Water:Town Water: Yes
  • Water Source: Public
  • Utilities: for Gas Range, for Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection
Interior and Exterior Features
Exterior Features
  • Exterior Features: Underground Sprinkler System, Private Yard, Outdoor Shower, Garden
  • Miles to Beach: 0 - .1
  • Private Dock: Yes
  • Appliances:Countertop Range: Yes
  • Appliances:Dishwasher: Yes
  • Appliances:Dryer - Electric: Yes
  • Appliances:Freezer: Yes
  • Appliances:Indoor Grill: Yes
  • Appliances:Microwave: Yes
  • Appliances:Range - Gas: Yes
  • Appliances:Refrigerator: Yes
  • Appliances:Security Alarm: Yes
  • Appliances:Stack Washer/Dryer: Yes
  • Appliances:Stove Hood: Yes
  • Appliances:Wall/Oven Cook Top: Yes
  • Appliances:Washer: Yes
  • Private Dock Description: Deep Water
  • Foundation: Poured
  • Roof Description: Shingle
  • Siding Description:Clapboard: Yes
  • Private Pool YN: No
  • Security Features: Security System
  • Patio And Porch Features: Deck - Exterior, Deck, Deck - Roof, Patio
  • General Property Info:Mi. to Beach Comments: Beachfront
Interior Features
  • Basement Description:Full: Yes
  • Basement Description:Interior Access: Yes
  • Basement Description:Walk Out: Yes
  • Floors: Carpet
  • Heating: Propane, Forced Air
  • Interior Features: Walk-In Closet(s), Linen Closet, Pantry, Recessed Lighting, Wet Bar, Kitchen Island
  • Basement: Yes
  • Separate Living Qtrs:Detached: Yes
  • Separate Living Qtrs:Second Floor: Yes
  • Fireplace: Yes
  • Sep Living Qtrs Info: Baths - Full: 1
  • Sep Living Qtrs Info: Baths - Total: 1
  • Sep Living Qtrs Info: Beds: 1
  • Total Rooms: 9
  • Baths Total: 6
  • Baths Full: 6
  • Baths Half: 0
  • Bedrooms Total: 7
  • Total Floor Plans Count: 0
  • RoomsTotal: 9
  • Bathrooms Total (Decimal): 6.00
  • Bathrooms Total (Notational): 6.00
  • Cooling: Yes
  • Fireplace Features: Family Room, Living Room, Master Bedroom
  • Fireplaces Total: 5
  • Heating: Yes
  • Stories: 2
  • Laundry Features: First Floor, Electric Dryer Hookup, Washer Hookup
  • Kitchen Appliances: Oven, Dishwasher, Microwave, Indoor Grill, Range, Refrigerator, Freezer, Washer, Dryer, Washer/Dryer, Vacuum System, Range Hood, Plumbed For Ice Maker
  • General Property Info:Stories: 2
Living Room
  • Living Room:Living Room Level: First Floor
  • Living Room:Flooring: Wood
  • Living Room:Special Door Access: French
Kitchen
  • Kitchen:Kitchen Level: First Floor
  • Kitchen:Flooring: Wood
  • Kitchen:Special Door Access: French
Dining Room
  • Dining Room:Dining Room Level: First Floor
  • Dining Room:Flooring: Wood
  • Dining Room:Special Door Access: French
Master Bedroom
  • Master Bedroom Level: Second Floor
Bedroom 2
  • Bedroom 2:Bedroom 2 Level: Second Floor
  • Bedroom 2:Flooring: Carpet
Bedroom 3
  • Bedroom 3:Bedroom 3 Level: First Floor
  • Bedroom 3:Flooring: Wood
  • Bedroom 3:Special Door Access: French
  • Bedroom 3: Closet: Yes
Bedroom 4
  • Bedroom 4:Bedroom 4 Level: First Floor
  • Bedroom 4:Flooring: Wood
  • Bedroom 4: Closet: Yes
Laundry Room
  • Laundry Room:Laundry Room Level: First Floor
Other Room 1
  • Other Room 1:Room Type: Sitting Room
  • Other Room 1:Level: First Floor
Other Room 2
  • Other Room 2:Room Type: Sitting Room
  • Other Room 2:Level: Second Floor
Other Room 3
  • Other Room 3:Room Type: Family Room
  • Other Room 3:Level: First Floor

Property History for 255 Bayberry Way

DateEvent & SourcePriceAppreciation
Apr 3, 2026

Listed (Active)

MLS PIN #73495629

$7,900,000—
Apr 3, 2026

Canceled

Cape Cod & Islands Multiple Listing Service #22203874

$8,950,000—
Apr 3, 2026

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22601177

$7,900,000—
DateEvent & SourcePrice
04/03/2026

Listed (Active)

MLS PIN #73495629

$7,900,000
04/03/2026

Canceled

Cape Cod & Islands Multiple Listing Service #22203874

$8,950,000
04/03/2026

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22601177

$7,900,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 255 Bayberry Way

Taxable ValueLand$7,947,300Additions$2,308,200Total$10,255,500
Tax Record2025$82,967 ($6,914 / month)
Home Facts
Beds6Baths4.5Total Finished SqFt4,896 SqFtAbove Grade Finished SqFt4,896 SqFtStories2Lot Size260,489 SqFtStyleSingle Family ResidenceYear Built1988CountyBARNSTABLEAPNOSTE M:092 L:001

Schools near 255 Bayberry Way

This home is within Barnstable School District.
Rating
School
Type
Grades
Distance
Public - K to 3
Public - 4 to 5
Public - 6 to 7
Public - 8 to 12
Rating
School
Distance
West Villages Elementary School
PublicK to 3

Barnstable United Elementary School
Public4 to 5

Barnstable Intermediate School
Public6 to 7

Barnstable High School
Public8 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

255 Bayberry Way is a single family home for sale in Osterville, MA 02655. This property was listed for sale on April 3, 2026 by Berkshire Hathaway HomeServices Robert Paul Properties, it's currently listed at $7,900,000. It has been on the market for a total of 37 days and was last sold on December 21, 2012. This listing's school district is Barnstable School District. Nearby schools include West Villages Elementary School, Barnstable United Elementary School and Barnstable Intermediate School. 255 Bayberry Way is a 7-bed, 6-bath, 4,896 sqft single family home built in 1988.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties, Robert B Kinlin

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Compass includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. Neither the listing firm nor Compass and its related brokerages shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.