255 Bayberry Way Osterville, MA $ 7,900,000
255 Bayberry Way
$ 7,900,000
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255 Bayberry Way

Osterville, MA, 02655
$ 7,900,000
Bedrooms7 Baths6.0 Sq 4,896

Monthly Estimate*

$ 48,642

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Single Family Home for sale in Osterville, MA

for $7,900,000 with 7 bedrooms and 6 full baths. This 4,896 square foot home was built in 1988 on a lot size of 5.98.

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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Single Family Active

Price

$ 7,900,000

Bedrooms

7

Full Bath

6

Property Type

Single Family

Taxes

$ 78,869

Style

Contemporary

Lot Size

5.98

Year Built

1988

Town/City

Osterville

County/Region

Barnstable

MLS | Web ID

22601177

Features
General
Sewer Private Sewer
Cooling Central Air
Roof Shingle
Appliances Cooktop Wine Cooler Washer Wall/Oven Cook Top Range Hood Washer/Dryer Stacked Security System Refrigerator Gas Range Microwave Indoor Grill Freezer Electric Dryer Dishwasher
Zoning RF-1
Garage Spaces 2
Patio/Porch Features Deck Screened Porch Patio
Architectural Style Contemporary
Construction Materials Clapboard
Year Built 1988
Stories Count 2
Township Barnstable
Property Subtype Single Family Residence
Tax Year 2026
County Barnstable
New Construction false
Property Type Residential
HOA false
Attached Garage false
Garage Y/N true
Total Rooms 9
Full Baths 6
Status Active
Directions Sea View Avenue to Bayberry Lane to the end
City Osterville
Body of Water West Bay
High School District Barnstable
Lot Size Units Acres
Lot Size Square Feet 260489
Carport Y/N false
Spa Features Bath
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 78869
Showing Instructions Contact Robert Kinlin at 508.648.2739 rkinlin@robertpaul.com or Donna Aucoin 508.737.0465 daucoin@robertpaul.com.
Home Warranty Y/N false
Property Condition Actual
Building Area Units Square Feet
Primary Bedroom Level Second
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District Barnstable
Elementary School District Barnstable
Tax Assessed Value 9672500
Waterview Y/N Bay/Harbor
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Interior
Interior Amenities Wet Bar Recessed Lighting Pantry Linen Closet
Basement Interior Entry Full
Flooring Vinyl Carpet Tile Wood
Total Fireplaces 5
Kitchen Level First
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 0
Laundry Features Laundry Areas First Floor
Total Bedrooms 7
Living Room Level First
Below Grade Finished Area Unit Type Square Feet
Kitchen Features Pantry Kitchen Island
Total Baths 6
Primary Bathroom Features Private Full Bath
Living Room Features Cathedral Ceiling(s)
Bedroom 4 Features Closet Shared Full Bath
Bedroom 3 Features Closet Shared Full Bath View
Bedroom 2 Features Private Full Bath View Walk-In Closet(s)
Kitchen Description Flooring: Wood Door(s): French
Primary Bedroom Features Office/Sitting Area Walk-In Closet(s) View
Dining Room Level First
Bedroom 4 Level First
Bedroom 3 Level First
Second Bedroom Level Second
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Exterior
Exterior Amenities Outdoor Shower Garden
Lot Features Marina School House of Worship Near Golf Course Shopping Cleared
Total Parking 5
Lot Size Area 5.98
Foundation Details Poured
Spa true
Building Area Total 4896
Lot Size Acres 5.98
Road Surface Type Paved
Lot Size Source Assessor
Waterfront Y/N true
Door Features French
Road Frontage Type Dead End Street
Dock Deep Water
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* Excluded Features
List By
Robert B Kinlin

Listing Agent

Berkshire Hathaway Homeservices Robert Paul Properties

Broker

rkinlin@robertpaul.com

Email

Affordability Calculator

$55,214
Per Month
88%
12%
0%
Monthly Principal & Interest
$48,642
Monthly Property Taxes
$6,572
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4795841 Elementary School
4795840 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
4/8/2026$7,900,000 Listed Price

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255 Bayberry Way, Osterville, MA, 02655 is a Single Family Home for sale at $7,900,000 with 4,896 sqft and a lot size of 5.98. 255 Bayberry Way has 7 bedrooms, 6.0 baths, and was built in 1988. The property's zip code is 02655 which is in Osterville, MA