26 Winthrop Ave Oak Bluffs, MA ^$ 839,000

26 Winthrop Ave

^$ 839,000

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Recently Listed

26 Winthrop Ave

Oak Bluffs, MA, 02557

^$ 839,000

Bedrooms1 Baths1.0 Sq 804

Monthly Estimate*

^$ 5,298

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Single Family Home for sale in Oak Bluffs, MA

for $839,000 with 1 bedroom and 1 full bath. This 804 square foot home was built in 1950 on a lot size of 0.34.

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.

Single Family Active

Price

^$ 839,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 3,598

Style

Cape

Lot Size

0.34

Year Built

1950

Town/City

Oak Bluffs

County/Region

Dukes

MLS | Web ID

73548644

List By

Alisan Lohan - Conway

Listing Agent

Alisan Lohan - Conway Properties

Broker

Affordability Calculator

$5,597

Per Month

Monthly Principal & Interest: $5,298
Monthly Property Taxes: $300
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Trends

Single family listings in Oak Bluffs, MA

Average List Price ^$2,040,290

Percent of Sale Price 143%

About Oak Bluffs, MA

4,795 Population

29% Since 2002

^$64,471 Median Income

46.88 Median Age

19% Households with Children

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Trends Information provided by ATTOM Data Solutions.

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Pricing History

Date	Price	Price Change	Description
7/13/2026	$839,000		Listed Price

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26 Winthrop Ave, Oak Bluffs, MA, 02557 is a Single Family Home for sale at $839,000 with 804 sqft and a lot size of 0.34. 26 Winthrop Ave has 1 bedrooms, 1.0 baths, and was built in 1950. The property's zip code is 02557 which is in Oak Bluffs, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 7/14/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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26 Winthrop Ave

Single Family Home for sale in Oak Bluffs, MA

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