Raymond M. Hall, REALTOR® | Call | Text | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$8,800,000
-16.2% from original list of $10,500,000 · August 24, 2026

25 Oyster Way, Osterville, MA 02655

5 bedrooms 4 Full Baths 2 Half Baths 7,157 Sq Ft 1.65 acres 3 Car Garage
MLS# 22603271 · Residential / (Single Family Residence) · Osterville Waterfront
Listed: 07/05/26 (listing data as of 09/8/26 at 11:30 am)
  • Primary Suite
  • Chef's Kitchen
  • 1st Floor Primary Bedroom
  • Waterfront
  • Private Dock
  • Ch. 91 License
  • Water Views
  • Private Pool
  • Central A/C

About This Property

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 TypeResidential
(Single Family Residence)
StatusFor Sale
MLS Number22603271
Year Built1999
Annual Taxes$64,017 (2026)
Total Assessment$7,851,100
Square Footage7,157
Price/Sq Ft$1230/sq ft
Lot Size1.65 acres
Total Rooms10
Bedrooms5
Full Baths4
Half Baths2
RenovatedYes
Year Renovated2026
Heat Source Forced Air, Oil, Propane
Add'l Heating Forced Air
Cooling A/C Central Air
Association Fee $4,620.00 (Annually)
Association Fee Includes Road Maintenance, Security
Garage Spaces3
Days on Market65
WaterfrontYes
Private Dock Yes, Ch. 91 License, Deep Water
Private PoolYes
Private Pool Description Covered, Gunite, Heated, In Ground
Water Body ViewWest Bay
Miles to Beach0 - .1
Fireplaces1
Lot Features Cleared, Level, Views

Bedroom Details

Primary Bedroom

  • First Floor
  • View
  • French Door
  • Private Full Bath
  • Wood Flooring
  • Cathedral Ceiling(s)

Bedroom 2

  • Second Floor
  • Walk-In Closet(s)
  • View
  • French Door
  • Private Full Bath
  • Carpet Flooring
  • Balcony

Bedroom 3

  • Second Floor
  • Walk-In Closet(s)
  • View
  • French Door
  • Private Full Bath
  • Carpet Flooring
  • Balcony

Bedroom 4

  • Second Floor
  • View
  • French Door
  • Shared Full Bath
  • Wood Flooring
  • Balcony

Living Area Details

Living Room

  • View
  • Wood Flooring
  • Cathedral Ceiling(s)
  • Built-in Features
  • Beamed Ceilings

Dining Room

  • First Floor
  • View
  • Wood Flooring
  • Beamed Ceilings

Kitchen

  • First Floor
  • French Door
  • Pantry
  • Kitchen Island
  • Wood Flooring
  • Eat-in Kitchen
  • Granite Counters

Appliances

  • Dishwasher
  • Electric Dryer
  • Gas Range
  • Microwave
  • Range Hood
  • Refrigerator
  • Security System
  • Washer
  • Wine Cooler

Foyer

  • First Floor
  • Tile Flooring

Sunroom

  • First Floor

Office

  • Second Floor

Laundry

  • First Floor
  • Laundry Areas
  • Tile Flooring
  • Built-in Features

Family Room

  • First Floor

Convenient To

  • Golf Course
  • House of Worship
  • Marina
  • School
  • Shopping
  • Convenient to West Bay
  • Convenient to Nantucket Sound

Exterior Features

  • Private Yard

Interior Features

  • Electric Dryer Hookup
  • HU Cable TV
  • Linen Closet
  • Pantry
  • Walk-In Closet(s)
  • Washer Hookup
  • Wet Bar

Location

Nearby Listings

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Listing Courtesy of: Robert B Kinlin / Berkshire Hathaway HomeServices Robert Paul Properties

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 John C. Ricotta & Associates 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 09/08/2026. Neither the listing broker nor John C. Ricotta & Associates 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.