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$1,950,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,459 Sq. Ft.
  • 0.23 Acres
  • Updated 34 minutes ago
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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!

Full Property Details for 25 Oak Ave

General

  • Price: $1,950,000
  • Taxes: $2,758 (2026)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73593599
  • Updated: Today (10/21/2026)
  • Added to Site: Today

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Bathroom 1: First
  • Bathroom 2: Second

Bedrooms

  • Total Bedrooms: 2
  • Primary Bedroom: First
  • Bedroom 2: Second

Other Rooms

  • Living Room: First
  • Kitchen: First
  • Dining Room: First

Parking

  • Parking Features: Off Street

Location

  • County: Dukes

Structural Information

  • Architectural Style: Contemporary, Farmhouse
  • Basement: Yes
  • Square Feet: 1,459
  • Year Built: 2026

Lot Features

  • Lot Size (Acres): 0.23

Financial Considerations

  • Tax Amount: $2,758.42
  • Tax Year: 2026

Disclosures and Reports

  • Property ID: 3875184

Listed by Sandpiper Realty, Inc., Lisa Stewart

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Listing agent

— 25 Oak Ave —

  • Lisa Stewart

    Sandpiper Realty, Inc.

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 25 Oak Ave

School Districts:Oak Bluffs School District, Martha's Vineyard School District
NameGradesDistance
Oak Bluffs Elementary School
50 Tradewinds Road, Oak Bluffs, MA 02557
PK-81 mi
Marthas Vineyard Regional High School
100 Edgartown-Vineyard Haven R, Oak Bluffs, MA 02557
9-123.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 25 Oak Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/21/2026
Listed
$1,950,000
200%
MLS
9/05/2025
Sold
$650,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 25 Oak Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,744
2%
$741,400
5%
2024
$3,681
-9%
$703,900
-9%
2023
$4,063
—
$769,600
29%
2022
$4,052
16%
$596,700
26%
2021
$3,487
5%
$473,200
6%
2020
$3,322
3%
$446,500
7%
2019
$3,214
15%
$417,900
17%
2018
$2,795
4%
$356,900
8%
2017
$2,696
3%
$330,800
3%
2016
$2,606
4%
$321,300
2%
2015
$2,500
8%
$314,100
6%
2014
$2,325
—
$297,700
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Sandpiper Realty, Inc., Lisa Stewart

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25 Oak Avenue, Oak Bluffs, MA 02557 (MLS# 73593599) is a Single Family property with 2 bedrooms and 2 full bathrooms. 25 Oak Avenue is currently listed for $1,950,000 and was received on October 21, 2026. Want to learn more about 25 Oak Avenue? Do you have questions about finding other Single Family real estate for sale in Oak Bluffs? You can browse all Oak Bluffs real estate or contact a Coldwell Banker agent to request more information.

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