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Friday, October 30, 2026 Dukes County, Massachusetts · Change town
Real Estate

Windemere Road Sale at $1.7 Million Tops Quiet Month for Oak Bluffs Sales

Oak Bluffs recorded six property deeds between Sept. 11 and Oct. 10. Five of the six listed a sale price, ranging from $75,000 to $1.7 million, with a median of $831,600. The month's top sale was 33 Windemere Rd., which sold for $1.7 million to Martha's Vineyard Hospital Inc. Five of th…

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OAK BLUFFS -- Six property transfers were recorded at the Dukes County Registry of Deeds for Oak Bluffs between Sept. 11 and Oct. 10, led by a $1.7 million sale on Windemere Road that was the period's largest transaction by a wide margin.

MARKET OVERVIEW

Six deeds were recorded in the period. Five of the six included a sale price, ranging from $75,000 to $1,700,000. The median sale price among the five priced transactions was $831,600. Six recorded transfers is a modest count on its own, and the data available does not include a prior-month or prior-year total for Oak Bluffs to measure it against.

TOP SALES

The highest-priced transaction was 33 Windemere Rd., which sold for $1,700,000 on Sept. 14. The sellers, listed as trustees Gregory Linn and Jason Linn, conveyed the property to Martha's Vineyard Hospital Inc.

The second-highest sale was 61 D Ocean Ave., which sold for $1,185,000 on Sept. 11. Sellers Thomas Hjerpe and Mary Jo Hjerpe conveyed the property to buyer Renee Gosline.

The third-highest sale was 3 Kims Way, which sold for $831,600 on Sept. 15. Seller Diane F. Smith conveyed the property to Success Mortgage Partners Inc. and Mortgage Electronic Registration Systems Inc.

Rounding out the priced sales were 55 Tiffany Dr., which sold for $110,000 on Sept. 14, with sellers listed as trustees Laurence H. Schaeffer and Helene F. Schaeffer conveying to Rockland Trust Co.; and 35 Clinton Ave., which sold for $75,000 on Sept. 14, with seller Marilyn S. Freeman conveying to Rockland Trust Co.

A sixth deed, recorded Sept. 15 between seller Staffarita LLC and a grantee listed as Certificate of Municipal Liens, did not include a street address or sale price in the available data.

NEIGHBORHOOD BREAKDOWN

No street name repeated among the six deeds, so sales are grouped here by price tier. Two sales fell under $500,000: 55 Tiffany Dr. ($110,000) and 35 Clinton Ave. ($75,000). One sale fell in the $500,000-to-$1 million range: 3 Kims Way ($831,600). Two sales topped $1 million: 61 D Ocean Ave. ($1,185,000) and 33 Windemere Rd. ($1,700,000). The sixth deed, with no address or price yet available, is not assigned to a tier.

MARKET NOTES

Of the six deeds, only the 61 D Ocean Ave. sale, from Thomas and Mary Jo Hjerpe to Renee Gosline, was a straightforward transfer between individual sellers and an individual buyer at a disclosed price. The other five each involved at least one corporate, institutional or trust party. Trustees were listed as sellers in two transactions, 33 Windemere Rd. and 55 Tiffany Dr. Rockland Trust Co. was the listed buyer in two transactions, 55 Tiffany Dr. and 35 Clinton Ave. The Windemere Road sale went to Martha's Vineyard Hospital Inc., and the Kims Way sale went to a mortgage company and a mortgage registration entity. No bedroom, bathroom or square-footage data was available for any of the six properties, so no price-per-square-foot comparison could be made this period.

The price for the Staffarita LLC-to-Certificate of Municipal Liens transfer had not reached the registry's data as of this report. Deed records typically post a sale price within about a week of recording, so that figure, along with the property's address, may become available in next month's roundup.


Recorded Deeds

Source: Registry of Deeds. Sale amounts shown as recorded; transfers without a disclosed consideration are noted as such.

Sep 7 - Sep 13
DateAddressGrantorGranteeSale Amount
Sep 1161 D Ocean AveHjerpe Thomas; Hjerpe Mary JoGosline Renee$1,185,000
Sep 14 - Sep 20
DateAddressGrantorGranteeSale Amount
Sep 1433 Windemere RdLinn Gregory Trs; Linn Jason TrsMarthas Vineyard Hospital Inc$1,700,000
Sep 1455 Tiffany DrSchaeffer Laurence H Trs; Schaeffer Helene F TrsRockland Trust Co$110,000
Sep 1435 Clinton AveFreeman Marilyn SRockland Trust Co$75,000
Sep 153 Kims WaySmith Diane FSuccess Mortgage Partners Inc; Mortgage Electronic Registration Systems Inc$831,600
Sep 15(no address)Staffarita LLCCertificate Of Municipal LiensNot yet available

Compiled from official town feeds, community organizations, and local press. Outside reporting is attributed inline.

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