255 Bayberry Way, Osterville, MA, 02655

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$8,950,000
1223 Days On Site

255 Bayberry Way
Osterville, MA 02655

For Sale|Single Family Residence|Active
7
Beds
6
Total Baths
6
Full Baths
4,896
SqFt
$1,828
/SqFt
1988
Built
County:
Barnstable
Listing courtesy of Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties
255 Bayberry Way255 Bayberry Way255 Bayberry Way255 Bayberry Way
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Mortgage Calculator

Monthly Payment (Est.)

$40,834
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2025 Information is deemed reliable but not guaranteed.

Welcome to ''Point House'' a spectacular 5.98-acre waterfront estate on a peninsula overlooking the glistening waters of West Bay. In a setting of unsurpassed beauty, the 4,896 square foot residence offers truly exceptional water vistas, beautiful gardens, an expansive private sandy beach, and a substantial deep-water dock from which you can sail into the waters of Nantucket Sound. The 6-bedroom home features generous yet comfortable living spaces, beautiful architectural detailing, custom wood flooring and 5 fireplaces. The entry foyer welcomes you to the beautiful views and impressive deck that runs the length of the home and beckons you to step outside to take in the panoramic views. Highlights include a light filled, two story great room with a beautiful floor-to-ceiling brick fireplace, a well-equipped kitchen opening into the dining area and a family room accented by a fireplace all opening to the outside living spaces making this flow ideal for quiet family enjoyment or larger scale entertaining. Two bedrooms and a sitting room with fireplace can also be found on the 1st level. The primary bedroom features beautiful water views, a spacious bath, walk in closet and a large sitting room with fireplace, and three additional bedrooms and a sitting room finish the 2nd level. A third-floor walkup to a tower provides the perfect vantage point to watch the incredible sunsets you'll experience from this property. Also offered is a detached two car garage which includes living space above for extended family and guests. This seaside estate affords the utmost privacy yet offers proximity to the village of Osterville with its boutique shops and fine dining. Experience an exceptional lifestyle from this one-of-a kind waterfront estate!

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Listing Snapshot
Price 
$8,950,000
Days On Site 
1223 Days
Bedrooms 
7
Inside Area (SqFt) 
4,896 sqft
Total Baths 
6
Full Baths 
6
Partial Baths 
N/A
Lot Size 
5.98 Acres
Year Built 
1988
MLS® Number 
22203874
Status 
Active
Property Tax 
$82,058
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
a month agoListing updated with changes from the MLS®
8 months agoPrice changed to $8,950,000
3 years agoListing first seen on site
General Features
Acres 
5.98
Garage 
Yes
Garage Spaces 
2
Land Lease 
No
Parking Spaces 
5
Property Sub Type 
Single Family Residence
Sewer 
Private Sewer
SqFt Total 
4896
Style 
Contemporary
Zoning 
RF-1
Interior Features
Appliances 
DryerCooktopWine CoolerWasherRange HoodWasher/Dryer StackedRefrigeratorGas RangeMicrowaveIndoor GrillFreezerDishwasher
Basement 
Interior EntryFull
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
5
Flooring 
VinylCarpetTileWood
Heating 
Interior 
Wet BarRecessed LightingPantryWalk-In Closet(s)
Spa 
Yes
Bedroom 2 
Level - SecondDescription - Flooring: Carpet
Bedroom 3 
Level - FirstDescription - Flooring: Wood,Door(s): French
Bedroom 4 
Level - FirstDescription - Flooring: Wood
Dining Room 
Level - FirstDescription - Flooring: Wood,Door(s): French
Kitchen 
Level - FirstDescription - Flooring: Wood,Door(s): French
Living Room 
Level - FirstDescription - Flooring: Wood,Door(s): French
Master Bedroom 
Level - SecondDescription - Flooring: Carpet
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Exterior Features
Construction Details 
Clapboard
Exterior 
Outdoor ShowerGarden
Lot Features 
On Golf CourseNear Golf CourseClearedWaterfront
Patio And Porch 
DeckPatio
Roof 
Shingle
Spa 
Yes
Spa Features 
Bath
View 
WaterBay
Waterfront 
Yes
Waterfront Features 
West Bay
Waterview 
WaterBay
Windows/Doors 
French Doors
Community Features
MLS Area 
Mid-Cape
Roads 
Paved
School District 
Barnstable
Township 
Barnstable
Schools
School District
Barnstable
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties



Listing information is provided by Participants of the Cape Cod Islands Association of REALTORS MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Copyright 2025, Cape Cod Islands Association of REALTORS MLS.
Last checked: 2025-11-27 04:36 AM UTC

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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