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For SaleWaterfrontMLS# 22603271

25 Oyster Way

Osterville, MA 02655
$8,800,000
5Beds
6Baths
7,157Sq Ft
3 carGarage
1.65 acres · Built 1999
Waterfront· Waterview, Waterfront, Bay/Harbor

Home For Sale in Osterville, MA

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.

Property Details

Property Type
Single Family Residence
Year Built
1999
Bedrooms
5
Bathrooms
4 full · 2 half
Sq Footage
7,157
Lot / Acres
1.65 acres
County
Barnstable
Rooms Total
10
Stories
2
Garage
3 car
Parking
5 spaces
Basement
Partial
Flooring
Wood, Tile, Carpet
Fireplace
1
Roof
Wood, Shingle
Construction
Stucco
Waterfront
Yes
HOA
yes
Annual Taxes
$64,017
Tax Year
2026
Assessed Value
$7,851,100

Features & Amenities

Dishwasher
Microwave
Gas Range
Refrigerator
Range Hood
Washer
Wine Cooler
Oil
Water Heater
HU Cable TV
Linen Closet
Pantry
Walk-In Closet(s)
Wet Bar
Cleared
Level
Views
Patio
Screened Porch
Electric Dryer
Electric Dryer Hookup
Washer Hookup

Interior Details

Appliances
Dishwasher, Microwave, Gas Range, Refrigerator, Range Hood, Washer, Wine Cooler, Oil, Water Heater
Interior Features
HU Cable TV, Linen Closet, Pantry, Walk-In Closet(s), Wet Bar
Laundry
Electric Dryer, Electric Dryer Hookup, Washer Hookup

Exterior & Location Details

Patio / Porch
Patio, Screened Porch
Directions
Bridge St to Oyster Harbors Gate House

Listed by: Robert B Kinlin from Berkshire Hathaway HomeServices Robert Paul Properties

© 2026 Cape Cod & Islands Multiple Listing Service. All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of CCIMLS. Information provided is deemed reliable but not guaranteed.

Location

25 Oyster Way

Osterville, MA 02655

Open in Google Maps
Alexander Malo
Alexander Malo
Wood Real Estate

Water Features

Waterfront

Yes

Waterfront Features

Waterview, Waterfront, Bay/Harbor

Water Body Name

West Bay,Salt

Listing Details

MLS #22603271
StatusActive
List Price$8,800,000
Lot Size1.65 acres
Year Built1999

About Osterville

Median Price
$1.45M
Avg Days on Market
38
Explore Osterville
CCIMLS Data Distribution

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Wood Real Estate, Inc. are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Wood Real Estate, Inc. shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.