Single Family Residence at 26 Winthrop Ave, Oak Bluffs MA 02557
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28 photos

$839,000

26 Winthrop Ave, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
Listed by Alisan Lohan - Conway
Bedrooms
1
Bathrooms
1
Living area
804 sqft
Year built
1950

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.

Property details

MLS
MLS Property Information Network
MLS #
73548644
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
105
On market date
July 8, 2026
Stories
N/A
Total bathrooms
1
Garage spaces
N/A
Parking spaces
4
Lot size
0.34 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Oak Bluffs Elementary
0.31 mi away · Grades -1-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
427
Student:teacher ratio
8.7:1
District
Oak Bluffs
Middle
Lawrence
7.74 mi away · Grades 7-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
498
Student:teacher ratio
9.8:1
District
Falmouth
High
Martha's Vineyard Regional High
2.74 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
706
Student:teacher ratio
9.3:1
District
Martha's Vineyard

Walkability

Blended score for Oak Bluffs's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

82
Highly walkable
out of 100
EPA National Walkability Index
15.3 / 20 -- Most walkable
Google Places amenity density
90 / 100
Restaurants & cafes20
Grocery stores4
Parks16
Schools3
Transit stops16
Pharmacies0

Market position

How this listing compares to current activity in Oak Bluffs, from live MLS data.

On the market 105 days -- 326 fewer days than Oak Bluffs's current average of 431 days.
For reference, the median list price across 41 active listings in Oak Bluffs right now is $1,399,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$5,203/mo
$167,800 down
$671,200 loan
Principal & interest$4,353
Property tax (est.)$699
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated July 17, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.