26 Winthrop Ave, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
$839,000
Est. $4,742/month
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About this home
This little gem is waiting to be polished. Hidden behind a wall of vegetation on Winthrop Avenue, an 'oasis', with lots of potential. Existing one bedroom, two story house situated on a 1/3 Acre of land, a 14,810 sq.ft. level lot. Land is large enough for a house and guest house when meeting ZBA requirements, or build a new house and leave existing structure as an Accessory Dwelling Unit when in compliance Massachusetts ADU regulation - 760 CMR 71.00. Only .6 of a mile to Oak Bluffs Harbor and .5 mile to the top of Circuit Avenue! Title 5 Certification in place. Lot is in Zone II and will allow a total of two bedrooms with upgrade to an advanced treatment system. Just one house from Wesleyan Park or stroll to Harbor and Town. Empty and easy to show.
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Property History
Property Timeline
Listed for Sale
Jul 13, 2026
$839,000
Original listing
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/13/2026 | 🏠 Listed for Sale | $839,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $3,598 | $712,500 |
Financial Details
Annual Property Tax
$3,598
Tax Year 2025
Assessed Value
$712,500
Facts & Features
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1950
Living Area
804 sq ft
Lot Size
0.34 acres
Bedrooms
1
Full Baths
1
Total Rooms
4
Interior
Heating
Forced Air, Oil
Cooling
None
Flooring
None
Appliances
Electric Water Heater
Fireplace
None
Basement
Partial, Bulkhead
Laundry
None
Features
None
Exterior
Construction
Frame
Architecture
Cape
Roof
Shingle
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Features
Off Street
Total Spaces
4
Utilities
Electric
None
Water
Public
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$3,598
Assessed Value
$712,500
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
Down Payment Resource
Eligible
MA Disclosures
Seller Disclosures
Property Is Being Sold As Is.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Dukes
Total market time (incl. prior listings)
9 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1950
Bedrooms
1
Full Bathrooms
1
Living Area
804 sq ft
Total Rooms
4
Floor Layout
Interactive room guide
Floor Layout
Finished Area
803 sq ft above grade
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:
Electric Water Heater
Interior Features:
Windows:
Basement:
Partial, Bulkhead
Laundry:
Security:
Construction & Materials
Style:
Cape
Year Built:
1950
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Stone, Irregular, Other
Heating, Cooling & Utilities
Heating:
Forced Air, Oil
Cooling:
None
Hot Water:
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Wooded, Cleared
Road Surface:
Parking & Garage
Total Parking Spaces:
4
Parking Features:
Off Street
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
0.3 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
2.2 mi
Grades PK-08
C+
Tisbury Elementary School
2.4 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
2.8 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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Monthly Payment Calculator
Monthly Payment
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Principal, interest, taxes & insurance
Loan Amount
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After down payment
Total Interest
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Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$300
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
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Current Rate
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+0.5% Rate
$0/mo
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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
26 Winthrop Ave, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
Listing Information
Agent MLS ID
CT008356
Office MLS ID
AC2193
Listing Data Updated
Jul 17, 2026 3:05 AM 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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