255 Bayberry Way Osterville
Barnstable, MA, 02655
$7,900,000
7 Beds
6 Baths
4,896 SqFt
5.98 Acres
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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.

Property Details

Price:
$7,900,000
MLS #:
22601177
Status:
Active
Beds:
7
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Apr 3, 2026
Finished Sq Ft:
4,896
Total Sq Ft:
4,896
Lot Size:
260,489 sqft / 5.98 acres (approx)
Year Built:
1988
ContemporaryWaterfrontBarnstableWest Bay

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Schools

School District:
Barnstable

Interior

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
Bathrooms
6 Full Bathrooms
Cooling
Central Air
Fireplaces Total
5
Flooring
Vinyl, Carpet, Tile, Wood
Interior Features
Wet Bar, Recessed Lighting, Pantry, Linen Closet
Laundry Features
Laundry Areas, First Floor

Exterior

Architectural Style
Contemporary
Construction Materials
Clapboard
Exterior Features
Outdoor Shower, Garden
Garage Spaces
2
Lot Features
Marina, School, House of Worship, Near Golf Course, Shopping, Cleared
Parking Spots
5
Parking Total
5
Patio And Porch Features
Deck, Screened Porch, Patio
Roof
Shingle
Spa Features
Bath
Stories
2

Financial

Tax Year
2026
Taxes
$78,869

Map

Community

Market Summary

Current real estate data for Single Family in Barnstable as of May 13, 2026
211
Single Family Listed
82
Avg DOM
630
Avg $ / SqFt
$1,929,638
Avg List Price

Property Summary

    255 Bayberry Way Osterville Barnstable MA is a Single Family for sale in Barnstable, MA, 02655. It is listed for $7,900,000 and features 7 beds, 6 baths, and has approximately 4,896 square feet of living space, and was originally constructed in 1988. The current price per square foot is $1,614. The average price per square foot for Single Family listings in Barnstable is $630. The average listing price for Single Family in Barnstable is $1,929,638. To schedule a showing of MLS#22601177 at 255 Bayberry Way Osterville in Barnstable, MA, contact your Pleasant Bay Realty agent at (774) 209-1428.

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255 Bayberry Way Osterville
Barnstable, MA