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255 Bayberry Way

Osterville, MA 02655
  • $7,900,000
  • STATUS: Active
  • ON SITE: 13 Days
  • MLS #: 22601177
$7,900,000
  • 7
    BEDS
  • 5.98
    ACRES
  • 6
    BATHS
  • 0
    1/2 BATHS
  • 4,896
    SQFT
  • $1,614
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1988
County:
Area:

School Ratings & Info

School District:

Description

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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Cape Cod & Islands MLS logo © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' 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 is not guaranteed accurate by the MLS or Rand Atlantic Cape Cod Realty. Data last updated: 2026-04-17T00:25:23.913.
www.randatlantic.com/homes/174807317
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255 Bayberry Way Osterville, MA 02655

  • Price: $7,900,000
  • Status: Active
  • On Site: 13 Days
  • MLS #: 22601177
7
Beds
6
Baths
0
½ Baths
5.98
Acres
4,896
SQFT
$1,614
$/SQFT
1988
Built
Neighborhood:
Barnstable
County:
Barnstable
Area:
Barnstable
School District:
Barnstable
Property Description
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.
Exterior Features

Architectural Style Contemporary Carport No Construction Materials Clapboard Dock Yes Exterior Features Outdoor ShowerGarden Foundation Details Poured Lot Features MarinaSchoolHouse of WorshipNear Golf CourseShoppingCleared Open Parking No Parking Total 5 Patio And Porch Features DeckScreened PorchPatio Pool Private No Road Frontage Type Dead End Street Roof Shingle Separate Living Quarters Description DetachedSecond Floor Water Access Type Private Water Body Type Salt Water Front Yes Water View Yes

Interior Features

Appliances CooktopWine CoolerWasherWall/Oven Cook TopRange HoodWasher/Dryer StackedSecurity SystemRefrigeratorGas RangeMicrowaveIndoor GrillFreezerElectric DryerDishwasher Attached Garage No Basement Yes Basement1 Interior EntryFull Cooling True Cooling Features Central Air Door Features French Fireplace YN Yes Fireplaces Total 5 Flooring VinylCarpetTileWood Garage Yes Heating Yes Interior Features Wet BarRecessed LightingPantryLinen Closet Laundry Features Laundry AreasFirst Floor Master Bedroom Level Second Rooms Total 9 Spa Features Bath Spa YN Yes

Property Features

Association No Flood Insurance Required Yes: verify w/insurance agent Flood Zone AE Improvement Assessments 2490600 Land Assessments 7181900 Land Lease No Lead Paint Unknown Miles From Beach 0 - .1 New Construction No Nitrogen Sensitive Area Yes Other Assessments 0 Property Attached No Property Sub Type Single Family Residence Road Surface Type Paved Sewer Private Sewer Special List Conditions None Tax Annual Amount 78869 Tax Assessed Value 9672500 Tax Year 2026 Warranty Available False Water Body Name West Bay Waterview Type Bay/Harbor Year Built Description Actual Year Round Yes Zoning RF-1

Cape Cod & Islands MLS logo Listing information © 2026 Cape Cod & Islands Multiple Listing Service, Inc.
Listing provided courtesy of Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties: rkinlin@robertpaul.com


Cape Cod & Islands MLS logo © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved. IDX information is provided exclusively for consumers' 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 is not guaranteed accurate by the MLS or Rand Atlantic Cape Cod Realty. Data last updated: 2026-04-17T00:25:23.913.
 
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North Falmouth MA, 02556