For Sale
Single family home for sale at 25 Oyster Way, Osterville, MA 02655 | MLS# 73544944 | Listing updated on 2026-08-28
Photo 1 of Single family home for sale at 25 Oyster Way, Osterville, MA 02655 | MLS# 73544944 | Listing updated on 2026-08-28
Photo 2 of Single family home for sale at 25 Oyster Way, Osterville, MA 02655 | MLS# 73544944 | Listing updated on 2026-08-28
Photo 3 of Single family home for sale at 25 Oyster Way, Osterville, MA 02655 | MLS# 73544944 | Listing updated on 2026-08-28
Photo 4 of Single family home for sale at 25 Oyster Way, Osterville, MA 02655 | MLS# 73544944 | Listing updated on 2026-08-28
36+
Beds Icon

Street View

$8,800,000

Monthly Est:$43,801

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

25 Oyster Way, 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: 5 minutes ago
  • Listing updated: August 28, 2026 at 7:05 am
  • Listing Provided by: Robert Kinlin (508) 648-2739 | Berkshire Hathaway HomeServices Robert Paul Properties (508) 420-1414
  • Source: MLS Property Information Network-MA | MLS#: 73544944 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • 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

    MLS Property Information Network

  • MLS Number

    73544944

  • MLS Status

    Active

  • Days on Market

    116

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Location

HOA Management

N/A

HOA Fees

$4,620/ Annually

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

  • Interior Features

    Closet, Home Office, Wet Bar

  • Flooring

    Wood, Tile, Carpet, Flooring Wood

  • Cooling

    Central Air

  • Heating

    Forced Air, Oil

  • Sewer

    Private Sewer

  • Exterior Features

    Porch Screened, Balcony, Pool Above Ground Heated, Professional Landscaping

Construction

  • Year Built

    Year Built: 1999

  • Home type

    Single Family Residence

  • Architectural Style

    Contemporary

  • Foundation Details

    Concrete Perimeter

  • Roof

    Wood

Utilities & Energy

  • Basement

    Crawl Space

  • Utilities

    For Gas Range, For Electric Dryer, Washer Hookup

  • Pool Features

    Heated

  • Water Source

    Public

  • Laundry Features

    Electric Dryer Hookup, Washer Hookup

  • Parking Features

    Attached, Garage Door Opener, Off Street, Stone/gravel

  • Security Features

    Security System

Other Features

  • Lot Features

    Cleared

  • Community Features

    Shopping, Tennis Court(s), Golf, House Of Worship, Marina, Private School

  • Patio And Porch Features

    Screened

  • Disclosures

    Assessors Has As 3 Bedroom. Septic System In Place Is A 5 Bedroom Design.

Price History

DateEventPrice

08/24/2026

Source: mls_logoMLS Property Information Network-MA #73544944

Price Decreased

$8,800,000 -7.37%

$1,230/sqft

07/25/2026

Source: mls_logoMLS Property Information Network-MA #73544944

Price Decreased

$9,500,000 -9.52%

$1,327/sqft

07/06/2026

Source: mls_logoMLS Property Information Network-MA #73544944

Listed for Sale

$10,500,000 +0.48%

$1,467/sqft

03/23/2026

Source: mls_logoCape Cod And Islands MLS-MA #22304800

Listing Removed

$10,450,000

$1,460/sqft

10/30/2023

Source: mls_logoCape Cod And Islands MLS-MA #22304800

Listed for Sale

$10,450,000 +74.31%

$1,460/sqft

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Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 31, 2026, 06:00PM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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