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5 Beds
6 Baths
7,157 sqft

$8,800,000

25 Oyster Way, Osterville MA, 02655

Price per sqft$1,229.57
Built in1999
Property size7,157 sqft
Property typeResidential

Overview

Active

Listed Jul 5, 2026

Updated 10h ago

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.

$58,547/mo

Est. mortgage payment based on a $8,800,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
22603271

Interior Features

Bedrooms
5
Bathrooms
6
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.65 Acres

Other Property Details

Taxes
$64,017
Tax Frequency
Annually
Association Fee Frequency
Yearly
Garage
Yes
Waterfront
Yes

Also listed on MLSPIN

Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties, Robert B Kinlin

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. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Paul Grover are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 9/17/2026. Neither the listing broker nor Paul Grover 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.

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