255 Bayberry Way, Osterville, MA, 02655

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$7,900,000
9 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
$1,614
/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.)

$36,043
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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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Listing Snapshot
Price 
$7,900,000
Days On Site 
9 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 
22601177
Status 
Active
Property Tax 
$78,869
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
4 days agoListing updated with changes from the MLS®
a week 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 2026, Cape Cod Islands Association of REALTORS MLS.
Last checked: 2026-04-12 02:08 PM 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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