Single Family Residence at 25 Oak Avenue, Oak Bluffs MA 02557
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31 photos

$1,950,000

25 Oak Avenue, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
Listed by Lisa Stewart
Bedrooms
2
Bathrooms
2
Living area
1,459 sqft
Year built
2026

About this home

Thought to have been moved from the Campgrounds to the Highlands in the early 1900's, the Mary E. Gilkes house has been transformed into a sophisticated and easy-living Island abode. The thoughtful, intentional design and execution of this renovation/addition pays homage to its Victorian roots while adding every modern amenity for year-round or summer use. Every detail has been carefully considered from the mahogany front porch with Vineyard-blue ceilings that typifies the Oak Bluffs cottage history, to the "bonus" room/loft, to infrastructure which meets HERS requirements for energy efficiency. There isn't an inch of wasted space in this little powerhouse and the property offers a wealth of possibilities for expansion. The location is quiet and bucolic, and just up the hill from Circuit Ave., with easy access to East Chop and Eastville Beach. Roll right off the ferry and bring your Vineyard vision to life in this enchanting home where history, style and modern comfort come together!

Property details

MLS
MLS Property Information Network
MLS #
73593599
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
4
On market date
October 21, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
N/A
Parking spaces
2
Lot size
0.23 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
0.87 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
7.05 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
3.13 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 4 days -- 435 fewer days than Oak Bluffs's current average of 439 days.
For reference, the median list price across 40 active listings in Oak Bluffs right now is $1,387,000.

Mortgage calculator

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

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Est. monthly payment
$11,893/mo
$390,000 down
$1,560,000 loan
Principal & interest$10,118
Property tax (est.)$1,625
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 1 days ago.

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.