255 Bayberry Way
Barnstable, MA · $7,900,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

255 Bayberry Way

Barnstable, MA 02655
$7,900,000
104 days on market · Listed Apr 3, 2026
Data refreshed Jul 16, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
7
Baths
6
Sq Ft
4,896
Acres
5.98
Year Built
1988
$ / Sq Ft
$1,614
Days on Market
104

Investment Snapshot

Monthly Carrying
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Cash Flow / yr
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Cash-on-Cash
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Cash Required
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Projected Revenue / yr
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Avg Daily Rate
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Occupancy
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STR Range (P50)
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Location & Nearby

Map of 255 Bayberry Way, Barnstable MA with nearby beaches and points of interest
HThis property
  • A
    Wianno Yacht Club
    0.65 mi
  • B
    Oyster Harbor Marina
    0.77 mi
  • C
    Wianno Golf Club
    0.77 mi
  • D
    Nauticus Marina
    0.85 mi
  • E
    Crosby Yacht Yard Inc
    0.88 mi
  • F
    Osterville Town Marina
    1.03 mi
  • G
    🛝 Osterville Village Library Playground
    1.27 mi
  • H
    🍽️ Five Bays Bistro
    1.28 mi

About this property

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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📋 Barnstable Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Barnstable
Listed by Robert B Kinlin, Berkshire Hathaway HomeServices Robert Paul Properties