Raymond M. Hall, REALTOR® | (508) 221-2544 | ray@ricottarealestate.com | 1181 Main Street, Chatham, MA 02633
$9,500,000

25 Oyster Way, Osterville, MA 02655

5 Beds 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 07/30/26 at 3:09 pm)

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

Property Details

Property TypeResidential
(Single Family Residence)
StatusActive
MLS Number22603271
Year Built1999
Annual Taxes$64,017 (2026)
Total Assessment$7,851,100
Square Footage7,157
Price/Sq Ft$1327/sq ft
Lot Size1.65 acres
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 Market25
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
  • Cathedral Ceiling
  • Closet
  • Wood Flooring
  • Private Full Bath
  • French Door Access
  • View

Bedroom 2

  • Second Floor
  • Balcony
  • Carpet Flooring
  • Private Full Bath
  • French Door Access
  • View
  • Walk-in Closet

Bedroom 3

  • Second Floor
  • Balcony
  • Carpet Flooring
  • Private Full Bath
  • French Door Access
  • View
  • Walk-in Closet

Bedroom 4

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

Living Area Details

Living Room

  • Beamed Ceilings
  • Built-Ins
  • Cathedral Ceiling
  • Wood Flooring
  • HU Cable TV
  • View

Dining Room

  • First Floor
  • Beamed Ceilings
  • Wood Flooring
  • View

Kitchen

  • Pantry
  • First Floor
  • Wood Flooring
  • French Door Access
  • Upgraded Cabinets

Appliances

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

Family Room

  • First Floor

Sun Room

  • First Floor

Home Office

  • Second Floor

Laundry Room

  • First Floor
  • Built-Ins
  • Tile Flooring
  • Laundry Areas

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

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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 07/30/2026. 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.