For Sale
3D Tour3D Tour
Single family home for sale at 25 Oyster Wy, Osterville, MA 02655 | MLS# 22603271 | Listing updated on 2026-10-26
Photo 1 of Single family home for sale at 25 Oyster Wy, Osterville, MA 02655 | MLS# 22603271 | Listing updated on 2026-10-26
Photo 2 of Single family home for sale at 25 Oyster Wy, Osterville, MA 02655 | MLS# 22603271 | Listing updated on 2026-10-26
Photo 3 of Single family home for sale at 25 Oyster Wy, Osterville, MA 02655 | MLS# 22603271 | Listing updated on 2026-10-26
Photo 4 of Single family home for sale at 25 Oyster Wy, Osterville, MA 02655 | MLS# 22603271 | Listing updated on 2026-10-26
52+
Beds Icon

Virtual Tour

Beds Icon

Street View

$8,800,000

Monthly Est:$43,801

  • Beds Icon5 Beds
  • Beds Icon
    6 Baths
  • Beds Icon7,157sqft

25 Oyster Wy, Osterville, MA 02655

$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 Cape Cod And Islands MLS-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    2

  • County

    Barnstable County

  • City

    Osterville

  • 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

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

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 Security Guard

Road Maintenance 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

DateEventPrice

08/24/2026

Source: mls_logoCape Cod And Islands MLS-MA #22603271

Price Decreased

$8,800,000 -7.37%

$1,230/sqft

07/21/2026

Source: mls_logoCape Cod And Islands MLS-MA #22603271

Price Decreased

$9,500,000 -9.52%

$1,327/sqft

07/05/2026

Source: mls_logoCape Cod And Islands MLS-MA #22603271

Listed for Sale

$10,500,000

$1,467/sqft

Nearby Homes

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.

Advertising Broker: Derek Greene | The Greene Realty Group

Skip to Main Content