53 Circuit Avenue, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
$5,500,000
Est. $29,030/month
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About this home
Exceptional mixed-use property in the heart of Oak Bluffs thriving high-foot-traffic Circuit Avenue business district. Meticulously renovated and designed by architect Chuck Sullivan, this distinctive building combines sophisticated commercial and residential spaces with outstanding craftsmanship and state-of-the-art systems. The street level is 2,320 sf and offers exceptional flexibility for restaurant-bar and/or retail operators (a commercial kitchen and bar remain intact) and includes three handicapped accessible half baths and a covered rear exterior loading area. A very large newly excavated 1,717 sf basement provides rare clean, dry storage and auxiliary operational space. The second-floor with 1,669 sf, features two residential apartments, totaling six bedrooms and three full baths for income potential or owner flexibility. Formerly housing an A&P grocery store (The Great Atlantic & Pacific Tea Company) and 99-occupancy restaurants, the property presently houses an upscale retailer while retaining its restaurant-bar infrastructure for future use.
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Property History
Property Timeline
Listed for Sale
Aug 21, 2026
$5,500,000
Original listing
Agent: Stephanie Roache
Office: Donnelly + Co.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/21/2026 | 🏠 Listed for Sale | $5,500,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $12,233 | — |
Financial Details
Annual Property Tax
$12,233
Tax Year 2026
Facts & Features
Home Facts
Type
Commercial Sale
Year Built
1900
Lot Size
0.06 acres
Interior
Heating
None
Cooling
None
Flooring
None
Appliances
None
Fireplace
None
Basement
None
Laundry
None
Features
None
Exterior
Construction
None
Architecture
None
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Features
None
Utilities
Electric
None
Water
None
Sewer
None
Gas
None
Other
Public Water, Public Sewer
Financial
Annual Tax
$12,233
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Documents
None
County
Dukes
Property Overview
Listing Type
For Sale
Year Built
1900
Floor Layout
Interactive room guide
Floor Layout
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
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:
Appliances:
Interior Features:
Windows:
Basement:
Laundry:
Security:
Construction & Materials
Year Built:
1900
Structure Type:
Exterior Materials:
Roof:
Foundation:
Heating, Cooling & Utilities
Heating:
Cooling:
Hot Water:
Water Source:
Sewer:
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
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Lot Features:
Road Surface:
Parking & Garage
Parking Features:
Nearby Schools
School District
Martha's Vineyard School District local
School Safety
2024-25
5.0%
Above Average
5.0%
Suspensions
1.3%
In-School
0.5% below state avg
Elementary Schools
3 schools
A-
Oak Bluffs Elementary School
0.8 mi
|
#105 of 352
|
Score: 49.0
Improved 16 spots from last year
-9.2 below state avg
402 students
Diverse
Grades PK-08
Vineyard Montessori School
2.4 mi
Grades PK-08
C+
Tisbury Elementary School
2.7 mi
|
#239 of 352
|
Score: 37.3
Dropped 104 spots from last year
-20.9 below state avg
312 students
Diverse
Diverse Student Body
Grades PK-08
High Schools
1 school
A-
Martha's Vineyard Regional High School
3.2 mi
|
#95 of 346
|
Score: 60.5
Improved 49 spots from last year
+2.3 above state avg
744 students
Diverse
19 sports
• 1,209 athletes
Strong AP Program
Rising School
Career Tech Programs
College Ready Curriculum
Grades 09-12
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Including down payment
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Down: $0
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Monthly Payment Breakdown
Principal & Interest
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Property Tax
$1,019
Homeowners Insurance
$200
PMI (if <20% down)
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Loan Summary
Total of 360 payments
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
53 Circuit Avenue, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
Listing Information
Listing Agent
Stephanie Roache
Listing Office
Donnelly + Co.
Office Phone
508-627-1022
Agent MLS ID
CN242113
Office MLS ID
AN6036
Listing Data Updated
Aug 21, 2026 6:53 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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