143 Bayberry Way, Barnstable MA 02655
Barnstable, MA 02655 • Osterville
$16,500,000
Est. $90,181/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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About this home
Set along the soothing waters of West Bay, this exceptional waterfront estate, with approx. 400' of waterfront, captures magnificent western exposure, offering ever-changing views of boats navigating to and from the harbor and spectacular evening sunsets dancing across the water. This 'Wianno Head' area is one of the most coveted areas of Osterville with large, private estate settings. This property also benefits from protected conservation 'Land Trust' land directly across from its gated entrance to the property. The main residence encompasses warm, luxurious living spaces, distinguished by extensive custom millwork, custom stone, tile and brick work, and refined architectural details throughout. The gourmet kitchen and butler's pantry are designed to delight, while the grand living room and adjoining dining room provide an elegant setting for entertaining. A sunroom overlooks the water, while the inviting family room and adjacent dining area create comfortable spaces for everyday living. The residence offers a 1st floor bedroom suite, and the 2nd floor provides three bedroom suites and a glorious master suite with his-and-her bathrooms and dressing rooms, a private sitting room, and a deck with exceptional water views. The third floor features an additional bedroom and bath, a family room, and a charming widow's walk overlooking the surrounding landscape and bay. A finished lower level provides additional flexible living and recreational space. A separate two-bedroom, two-bath carriage house offers a full kitchen and living room, providing an ideal private retreat for guests and extended family. Encompassing three acres of beautifully landscaped, park-like grounds, that are irrigated by a private well, the property offers an extraordinary sense of privacy. Manicured lawns and gracious mature trees frame an inviting PebbleTech-finish pool, an expansive terrace, perfectly suited for outdoor entertaining and enjoying unforgettable sunsets. Steps lead down to the water's edge, where a private sitting area provides a peaceful place to take in the views. A permanent deep-water dock on West Bay complete this remarkable waterfront setting. The prestigious Wianno Club and Oyster Harbors Club, as well as Nauticus Yacht Club, Crosby Boatyard, and the numerous shops and restaurants in the village, are only minutes away. All information stated here in or verbally stated, should be verified by the Buyer(s) and their representatives.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Oct 3, 2026
$16,500,000
Original listing
Agent: John Hopkins
Office: Frank Sullivan Real Estate, LLC
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 10/03/2026 | 🏠 Listed for Sale | $16,500,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $78,577 | $9,636,700 |
Financial Details
Annual Property Tax
$78,577
Tax Year 2026
Assessed Value
$9,636,700
Facts & Features
2 Car Garage
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1914
Living Area
8,763 sq ft
Lot Size
3.02 acres
Bedrooms
8
Full Baths
9
Half Baths
2
Total Rooms
20
Interior
Heating
Forced Air, Natural Gas
Cooling
Central Air
Flooring
Wood
Appliances
Water Heater
Fireplace
None
Fireplaces
3
Basement
Full, Partially Finished, Walk-out Access
Laundry
None
Features
None
Exterior
Construction
Frame
Architecture
Colonial
Roof
Wood
Features
Patio, Pool - Inground Heated, Sprinkler System, Guest House
Pool
Pool - Inground Heated
Spa
None
Fencing
None
Patio/Porch
Patio
Parking
Garage Spaces
2
Has Garage
Yes
Features
Detached, Garage Door Opener
Total Spaces
12
Utilities
Electric
None
Water
Public, Private
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$78,577
Assessed Value
$9,636,700
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Measured
Sq Ft Disclosures
Total living area, bedrooms, and baths include main house, fin. basement, and the carriage house.
Documents
None
County
Barnstable
Total market time (incl. prior listings)
1 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1914
Bedrooms
8
Full Bathrooms
9
Half Bathrooms
2
Living Area
8,763 sq ft
Total Rooms
20
Floor Layout
Interactive room guide
Floor Layout
Finished Area
8,178 sq ft above grade
585 sq ft below grade
Display Options
Outdoor Areas
PoolPool - Inground Heated
Patio & porchPatio
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood
Appliances:
Water Heater
Interior Features:
Windows:
Basement:
Full, Partially Finished, Walk-Out Access
Laundry:
Security:
Security System
Construction & Materials
Style:
Colonial
Year Built:
1914
Structure Type:
Exterior Materials:
Frame
Roof:
Wood
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Forced Air, Natural Gas
Cooling:
Central Air
Hot Water:
Water Source:
Public, Private
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio, Pool - Inground Heated, Sprinkler System, Guest House
Patio & Porch:
Patio
Fencing:
Other Structures:
Guest House
Lot Features:
Road Surface:
Parking & Garage
Garage Spaces:
2
Total Parking Spaces:
12
Parking Features:
Detached, Garage Door Opener
Special Features
Fireplaces:
3
Fireplace Type:
Pool:
Private Pool
Pool Features:
Pool - Inground Heated
Waterfront:
Yes
Waterfront Type:
Waterfront, Bay, Dock/Mooring, Deep Water Access, Private, Bay, Beach Ownership(Private)
View:
Yes
View Type:
Scenic View(s)
Community Amenities:
Shopping, Golf, Conservation Area, Marina
Nearby Schools
School District
Barnstable School District local
B
School Safety
2024-25
2.9%
Above Average
2.1%
Suspensions
2.2%
In-School
0.8%
Emergency
2.6% below state avg
Elementary Schools
10 schools
Cape Cod Academy
2.0 mi
Strong Athletics
Grades K-12
St. John Paul II School
6.2 mi
Grades 05-12
Trinity Christian Academy of Cape Cod
7.7 mi
Grades PK-12
B
Centerville Elementary School
3.2 mi
|
#365 of 825
|
Score: 48.5
Dropped 130 spots from last year
-9.7 below state avg
248 students
Diverse
Strong Attendance
Grades K-03
B-
Barnstable United Elementary School
3.4 mi
|
#444 of 825
|
Score: 46.2
Improved 164 spots from last year
-12 below state avg
723 students
Diverse
Rising School
Diverse Student Body
Grades 04-05
A
West Villages Elementary School
3.5 mi
|
#135 of 825
|
Score: 57.4
Improved 196 spots from last year
-0.8 below state avg
397 students
Diverse
Rising School
Grades K-03
Fair Acres Country Day School
3.9 mi
Grades PK-K
C
Hyannis West Elementary School
4.8 mi
|
#664 of 825
|
Score: 37.7
Improved 2 spots from last year
-20.5 below state avg
293 students
Diverse
Diverse Student Body
Grades K-03
Enoch Cobb Early Learning Center
4.8 mi
162 students
Very Diverse
Diverse Student Body
Grades PK
B-
Barnstable Community Innovation School
6.0 mi
|
#460 of 825
|
Score: 45.8
Dropped 161 spots from last year
-12.4 below state avg
299 students
Diverse
Grades K-03
Middle Schools
2 schools
Bayberry Christian School
2.9 mi
Grades 01-08
C
Barnstable Intermediate School
5.0 mi
|
#269 of 352
|
Score: 34.8
Improved 19 spots from last year
-23.4 below state avg
581 students
Diverse
Diverse Student Body
Grades 05-07
High Schools
3 schools
C+
Barnstable High School
5.0 mi
|
#236 of 346
|
Score: 48.6
Improved 31 spots from last year
-9.6 below state avg
1,581 students
Diverse
18 sports
• 1,820 athletes
Rising School
Career Tech Programs
College Ready Curriculum
Strong Athletics
Grades 08-12
Living Independently Forever, Inc.
5.8 mi
Grades 09-12
A
Sturgis Charter Public School
6.3 mi
|
#45 of 346
|
Score: 68.4
Improved 31 spots from last year
+10.2 above state avg
833 students
Moderate
High Graduation Rate
Rising School
College Ready Curriculum
Grades 09-12
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Monthly Payment Breakdown
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Property Tax
$6,548
Homeowners Insurance
$200
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
Osterville
143 Bayberry Way, Barnstable MA 02655
Barnstable, MA 02655
Listing Information
Listing Agent
John Hopkins
Listing Office
Frank Sullivan Real Estate, LLC
Office Phone
508-428-4400
Agent MLS ID
CN234272
Office MLS ID
AN5407
Listing Data Updated
Oct 3, 2026 3:06 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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