25 Oyster Way Osterville, MA $ 10,500,000
25 Oyster Way
$ 10,500,000
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25 Oyster Way

Osterville, MA, 02655
$ 10,500,000
Bedrooms5 Baths4.2 Sq 7,157

Monthly Estimate*

$ 66,298

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View a Virtual Tour

Single Family Home for sale in Osterville, MA

for $10,500,000 with 5 bedrooms and 4 full baths, 2 half baths. This 7,157 square foot home was built in 1999 on a lot size of 1.65.

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.

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Single Family Active

Price

$ 10,500,000

Bedrooms

5

Full Bath

4

Half Bath

2

Property Type

Single Family

Taxes

$ 64,017

Style

Other

Lot Size

1.65

Year Built

1999

Town/City

Osterville

County/Region

Barnstable

MLS | Web ID

22603271

Features
General
Sewer Private Sewer
Cooling Central Air
Roof Wood Shingle
Appliances Dishwasher Wine Cooler Washer Range Hood Security System Refrigerator Gas Range Microwave Electric Dryer
Zoning RF-1
HOA Fee 4620
Garage Spaces 3
Patio/Porch Features Patio Screened Porch
Architectural Style Other
Pool Features Pool Cover In Ground Heated Gunite
Construction Materials Stucco
Year Built 1999
Stories Count 2
Township Barnstable
Property Subtype Single Family Residence
Tax Year 2026
Assoc Fee Paid Per Annually
County Barnstable
New Construction false
Property Type Residential
Association Amenities Road Maintenance Security
HOA true
Attached Garage true
Subdivision Name Oyster Harbors
Garage Y/N true
Total Rooms 10
Full Baths 4
Status Active
Directions Bridge St to Oyster Harbors Gate House
City Osterville
Body of Water West Bay
Entry Location First Floor
High School District Barnstable
Lot Size Units Acres
Lot Size Square Feet 71874
Carport Y/N false
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 64017
Showing Instructions Call Bob Kinlin 508.648.2739 or Donna Aucoin 508.737.0465 or email rkinlin@robertpaul.com / daucoin@robertpaul.com to schedule a showing.
Home Warranty Y/N false
Property Condition Updated/Remodeled Actual
Virtual Tour https://www.youtube.com/watch?v=CD3j_Qcu00Y https://www.youtube.com/watch?v=CD3j_Qcu00Y
Building Area Units Square Feet
Primary Bedroom Level First
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District Barnstable
Elementary School District Barnstable
Tax Assessed Value 7851100
Waterview Y/N Bay/Harbor
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Interior
Interior Amenities HU Cable TV Wet Bar Pantry Linen Closet
Basement Partial Cape Cod
Flooring Wood Carpet Tile
Total Fireplaces 1
Kitchen Level First
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 2
Laundry Features Laundry Room Built-Ins Laundry Areas First Floor
Total Bedrooms 5
Entry Level 1
Below Grade Finished Area Unit Type Square Feet
Kitchen Features Kitchen Upgraded Cabinets Kitchen Island Pantry
Total Baths 6
Primary Bathroom Features Private Full Bath
Living Room Features HU Cable TV Living Room View Beamed Ceilings Built-in Features Cathedral Ceiling(s)
Bedroom 4 Features Bedroom 4 Shared Full Bath Balcony View Closet
Bedroom 3 Features Bedroom 3 Balcony View Walk-In Closet(s) Private Full Bath
Bedroom 2 Features Bedroom 2 Balcony View Walk-In Closet(s) Private Full Bath
Dining Room Features View Dining Room Beamed Ceilings
Kitchen Description Countertop(s): Granite Flooring: Wood Door(s): French
Primary Bedroom Features View Closet Cathedral Ceiling(s)
Dining Room Level First
Bedroom 4 Level Second
Bedroom 3 Level Second
Second Bedroom Level Second
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Exterior
Fencing Fenced
Parking Features Basement
Lot Features Marina School House of Worship Near Golf Course Shopping Cleared Level
Total Parking 5
Lot Size Area 1.65
Foundation Details Concrete Perimeter
Building Area Total 7157
Lot Size Acres 1.65
Road Surface Type Paved
Lot Size Source Assessor
Waterfront Y/N true
Door Features French Doors French
Road Frontage Type Private Road
Dock Deep Water Ch. 91 License
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* Excluded Features
List By
Robert B Kinlin

Listing Agent

Berkshire Hathaway Homeservices Robert Paul Properties

Broker

rkinlin@robertpaul.com

Email

Affordability Calculator

$71,633
Per Month
93%
7%
0%
Monthly Principal & Interest
$66,298
Monthly Property Taxes
$5,335
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4795841 Elementary School
4795840 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
7/5/2026$10,500,000 Listed Price

Map


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25 Oyster Way, Osterville, MA, 02655 is a Single Family Home for sale at $10,500,000 with 7,157 sqft and a lot size of 1.65. 25 Oyster Way has 5 bedrooms, 4.2 baths, and was built in 1999. The property's zip code is 02655 which is in Osterville, MA