- Overview
- Description
- Property Details
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- HOA Management
- Facts & Features
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$8,800,000
Monthly Est:$43,801
5 Beds
- 6 Baths
4 full baths + 2 half baths
7,157sqft
25 Oyster Wy, Osterville, MA 02655
$8,800,000
$43,801/moEst:
Get Pre-Approved
Single Family Residence
Built in 1999
$385/mo HOA
1.65 acres lot
$1,230/sq.ft
Description
Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds designed for both grand entertaining and quiet moments of retreat. Inspired by the timeless character of a European country estate, the residence encompasses 7,157 square feet of thoughtfully designed living space where sophisticated craftsmanship meets effortless comfort. A dramatic foyer introduces the home's remarkable interior, opening to an impressive great room with soaring vaulted ceilings, architectural columns, a custom fireplace, and expansive walls of glass that frame the ever-changing waterfront. Designed for both everyday living and elegant entertaining, the sun-filled dining room captures tranquil water views and flows seamlessly into a beautifully appointed chef's kitchen featuring a coffered ceiling, granite countertops, an oversized center island, and direct access to a spacious waterside terrace. The first-floor primary suite offers a luxurious private retreat, while four additional bedrooms--including a gracious guest suite above the attached three-car garage--provide exceptional accommodations for family and guests. Outdoor living is equally compelling. Expansive terraces and inviting gathering spaces overlook the pool, manicured gardens, and deep-water dock, creating an idyllic setting for waterfront entertaining or peaceful afternoons by the shore. Set within one of Cape Cod's most coveted private enclaves, where golf, boating, and an unmatched sense of privacy define the lifestyle, this exceptional estate represents a rare opportunity to own a legacy property in Oyster Harbors. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.
- Houzeo last checked: 11 minutes ago
- Listing updated: October 26, 2026 at 7:34 pm
- Listing Provided by: Robert B Kinlin (508) 420-1414204 | Berkshire Hathaway HomeServices Robert Paul Properties (508) 420-1414
- Source: Cape Cod And Islands MLS-MA | MLS#: 22603271

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
2
County
City
Neighborhood
--
Year Built
1999
HOA Fees
$385/mo
Finished Area
7,157 sqft
Lot Size
1.65 acres lot
Basement Area
- sqft
MLS Name
Cape Cod And Islands MLS
MLS Number
22603271
MLS Status
Active
Days on Market
118
Cumulative Days on Market
113

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Location
HOA Management
N/A
HOA Fees
$4,620/ Annually
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Security Guard
Road Maintenance
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 5
Bathrooms: 6
Interior
Heating
Propane, Forced Air, Oil
Appliances
Water Heater, Wine Cooler, Range Hood, Gas Range, Dishwasher, Microwave, Refrigerator, Washer
Interior Features
Eat In Kitchen, Walk In Closet(s), Hu Cable Tv, Linen Closet, Pantry, Wet Bar, Kitchen Island
Exterior Features
Private Yard
Cooling
Central Air
Flooring
Wood, Tile, Carpet
Construction
Year Built
Year Built: 1999
Home type
Single Family Residence
Architectural Style
Other
Foundation Details
Concrete Perimeter
Roof
Wood, Shingle
Construction Materials
Stucco
Utilities & Energy
Laundry Features
Washer Hookup, Electric Dryer Hookup, Electric Dryer, Laundry Room
Parking Features
Garage Door Opener, Direct Access, Gravel, Off Street
Water Source
Public
Basement
Cape Cod, Garage Access, Partial
Pool Features
Covered, Gunite, Heated, In Ground
Association Amenities
Road Maintenance, Security
Security Features
Security System
Other Features
Subdivision Name
Oyster Harbors
Patio And Porch Features
Screened Porch, Patio
Lot Features
Views, Cleared, Level
Price History
| Date | Event | Price |
|---|---|---|
08/24/2026 Source: | Price Decreased | $8,800,000 -7.37% $1,230/sqft |
07/21/2026 Source: | Price Decreased | $9,500,000 -9.52% $1,327/sqft |
07/05/2026 Source: | Listed for Sale | $10,500,000 $1,467/sqft |
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Based on information from the Cape Cod and Islands Multiple Listing Service, Inc. through Oct 31, 2026, 09:00PM. Information is provided exclusively for consumers’ personal, non-commercial use, it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and the data is deemed reliable but is not guaranteed accurate by the MLS. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
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