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Monday, November 2, 2026 Dukes County, Massachusetts · Change town
Real Estate

Chilmark Sales Post $5 Million Median Price Amid September Property Transfers

Six Chilmark properties sold between Sept. 11 and Oct. 10, with recorded prices on three of them ranging from $2.7 million to $6.5 million and a median of $5 million. The top sale was 308 South Rd Beach Lot at $6.5 million on Sept. 18, the same day the adjoining 308 South Rd parcel sold…

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CHILMARK -- Six properties changed hands in Chilmark between Sept. 11 and Oct. 10, with recorded prices ranging from $2.7 million to $6.5 million and a median sale price of $5 million among the three transactions with prices on file so far.

MARKET OVERVIEW The Dukes County Registry of Deeds recorded six property transfers in Chilmark during the period. Of those, three carried a recorded sale price, ranging from $2.7 million to $6.5 million, with a median of $5 million. The other three sales have no price yet; that is typical of registry data and usually means the figure has not been entered yet, not that it was withheld. Six recorded transfers is a modest count for a single month, suggesting limited turnover rather than a broad wave of activity.

TOP SALES The largest transaction was 308 South Rd Beach Lot, which sold for $6.5 million on Sept. 18. The seller was listed as South Rd Beach Lot and Mitchell Kapor, as trustee; the buyer was Menemsha Meadow LLC. The same day, 308 South Rd sold for $5 million, with Menemsha Meadow LLC as seller and JPMorgan Chase Bank NA as buyer. The third priced sale, 6 Trails End, sold for $2.7 million on Sept. 16; the seller was New Red Hat LLC and the buyer was Peter Goldberg.

NEIGHBORHOOD BREAKDOWN South Road accounted for two of the six sales, both recorded Sept. 18: the Beach Lot parcel at $6.5 million and the adjoining 308 South Rd parcel at $5 million. The remaining four sales were each on a different street: 12 Welles Way, 6 Trails End, 33 Cove Rd, and an unspecified Chilmark address. By price tier, all three sales with recorded prices fell above $1 million, with two exceeding $5 million. The three sales without a price yet cannot be placed into a tier until the registry data updates.

MARKET NOTES Three of the six transfers in this period involved a trust or an entity tied to the same family or ownership group rather than a straightforward sale between unrelated parties. The Sept. 11 transfer of 33 Cove Rd moved the property between trustees sharing the Flanders name. The Sept. 25 transfer listed the Julie Jaffe Revocable Trust as seller. The Sept. 22 transfer of 12 Welles Way listed Dinah Andrews as both a seller and part of the buyer group. Separately, the two South Road sales on Sept. 18 involved Menemsha Meadow LLC as buyer in one transaction and seller in the other, recorded the same day. No bed, bath or square-footage data was available in the registry records for any of the six properties.


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 1133 Cove RdFlanders Noreen M Trs; Pond Shore TrustFlanders H Brian TrsNot yet available
Sep 14 - Sep 20
DateAddressGrantorGranteeSale Amount
Sep 166 Trails EndNew Red Hat LLCGoldberg Peter$2,700,000
Sep 18308 South Rd Beach LotSouth Rd Beach Lot; Kapor Mitchell TrsMenemsha Meadow LLC$6,500,000
Sep 18308 South RdMenemsha Meadow LLCJpmorgan Chase Bank Na$5,000,000
Sep 21 - Sep 27
DateAddressGrantorGranteeSale Amount
Sep 2212 Welles WayAndrews DinahSimoes Gustavo Silva; Andrews DinahNot yet available
Sep 25(no address)Jaffe Julie Trs Et Als; Julie Jaffe Revocable TrustBrandhorst Elizabeth TNot yet available

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

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