High-end sales push Winchester's June-July median past $2 million

WINCHESTER -- Twenty property transfers were recorded in Winchester between June 19 and July 18, with disclosed sale prices ranging from $250,000 to $3,500,000 and a median of $2,127,000 among the 14 sales that included a price.

MARKET OVERVIEW The South Middlesex Registry of Deeds recorded 20 Winchester property transfers during the period, of which 14 included a disclosed consideration amount. Prices among those 14 ranged from $250,000, for a unit at 200 Swanton St., to $3,500,000, for a home on Oxford Street. The median sale price was $2,127,000. The remaining six transfers did not include a sale price in the deed record, which is common for certain transaction types. Twenty recorded transfers in a single month is a notable volume of activity for the town, though the data does not indicate how this compares with other periods.

TOP SALES The month's highest-priced transaction was 50 Oxford St., which sold for $3,500,000 on June 26. The sellers were Timothy J. Clift and Nancy L. Clift, as trustees; the buyers were Joshua Geary and Katherine Johnston.

40 Foxcroft Rd. sold for $3,450,000 on June 26. The seller was Foxcroft Realty Trust, with Stefanos Bouboulis as trustee; the buyers were Rakshit Kumar and Neha Anand.

56 Yale St. sold for $2,830,000 on June 23. Mark Robinson and Gael D. Robinson were the sellers; Philip L. Vineburgh and Molly C. Vineburgh were the buyers.

10 Viking Rd. sold for $2,549,000 on June 29. Mark Sassi and Anita Sassi were the sellers; Pia M. Perrone and Brian T. Estaphan were the buyers.

216 Highland Ave. sold for $2,400,000 on June 30. The seller was Richard A. Toelke, individually and as trustee of the Richard A. Toelke Trust; the buyers were Noah Medlinsky and Elizabeth Medlinsky.

NEIGHBORHOOD BREAKDOWN No street recorded more than one sale during the period, so transactions are grouped here by price tier. One sale, the $250,000 unit at 200 Swanton St., fell below $1 million. Five sales priced between $1 million and $2 million, including 60 Holland St. ($1,015,000), 12 Hancock St. ($1,310,000), a unit at 7 Wainwright Rd. ($1,350,000), a Winchester property purchased by Pediatricians Realty LLC ($1,460,000), and 29 Pilgrim Dr. ($1,700,000). Six sales fell between $2 million and $3 million: 36 Cambridge St. ($2,025,000), 18 Mystic Ave. ($2,229,000), 16 Plato Ter. ($2,300,000), 216 Highland Ave. ($2,400,000), 10 Viking Rd. ($2,549,000) and 56 Yale St. ($2,830,000). Two sales, 50 Oxford St. and 40 Foxcroft Rd., exceeded $3 million.

MARKET NOTES Six of the 20 recorded transfers -- at 2 Robinhood Rd., 35 Brooks St., 4 York Rd., 5 Emerson Ct., 8 Pocahontas Dr. and 42 Everett Ave. -- listed grantors and grantees sharing the same last name, with several deeds naming the same individual as both an individual seller and a trustee buyer. These appear to be transfers within the same family or into a trust; the deed data does not indicate the reason for these transfers. None of the six included a disclosed sale price. Of the 14 sales with disclosed prices, most were single-family homes; two involved condominium units (7 Wainwright Rd. Unit 30 and 200 Swanton St. Unit 538). One purchase was made by a limited liability company, Pediatricians Realty LLC, which acquired a Winchester property for $1,460,000 from AFT LTD LP and Donald J. Annino Jr., as trustee; the deed record does not specify the property's use. Bedroom, bathroom and square-footage figures were not available from the deed records for any of the 20 transactions.


Recorded Deeds

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

Jun 22 - Jun 28

DateAddressGrantorGranteeSale Amount
2026-06-2218 MYSTIC AVE, WinchesterSALIBA ESTEPHEN; SALIBA EMMASPINALE STEVEN C; BEAL PERRY E$2,229,000
2026-06-227 WAINWRIGHT RD UNIT 30, WinchesterREVOCABLE TRUST; SHANAHAN NANNETTE J TRBALANON CHRISTINA; SWOBODZINSKI KAMIL$1,350,000
2026-06-22200 SWANTON ST UNIT 538, WinchesterFIRST BAY REALTY LLCXIANG LIPING$250,000
2026-06-2242 EVERETT AVE, WinchesterCURTIS GEOFFREY A TR; ODONNELL LEAH K TRODONNELL LOUISE J TR; ODONNELL MARTIN J TRNot disclosed
2026-06-2356 YALE ST, WinchesterROBINSON MARK; ROBINSON GAEL DVINEBURGH PHILIP L T; VINEBURGH MOLLY C$2,830,000
2026-06-2316 PLATO TER, WinchesterALTARAS NEDIM EMIL; ALTARAS GINA MBIEL STACIA; BIEL WYATT$2,300,000
2026-06-248 POCAHONTAS DR, WinchesterSCHWARTZMAN THOMAS N; SCHWARTZMAN TOBY JSCHWARTZMAN THOMAS N TR; SCHWARTZMAN TOBY J TRNot disclosed
2026-06-25WinchesterAFT LTD LP; ANNINO DONALD J JR TRPEDIATRICIANS REALTY LLC$1,460,000
2026-06-255 EMERSON CT, WinchesterYAO YINGYAO YING TR; YE CHANG TRNot disclosed
2026-06-2650 OXFORD ST, WinchesterCLIFT TIMOTHY J TR; CLIFT NANCY L TRGEARY JOSHUA; JOHNSTON KATHERINE$3,500,000
2026-06-2640 FOXCROFT RD, WinchesterFOXCROFT REALTY TRUST; BOUBOULIS STEFANOS TRKUMAR RAKSHIT; ANAND NEHA$3,450,000
2026-06-264 YORK RD, WinchesterTULLY KEVIN R; TULLY KATHERINE ETULLY KATHERINE ENot disclosed

Jun 29 - Jul 5

DateAddressGrantorGranteeSale Amount
2026-06-2910 VIKING RD, WinchesterSASSI MARK; SASSI ANITAPERRONE PIA M; ESTAPHAN BRIAN T$2,549,000
2026-06-2929 PILGRIM DR, WinchesterGENTUSO JOHN L; GENTUSO KARENMARTIN JOHN JR; DEPAOLO KRISTEN$1,700,000
2026-06-2935 BROOKS ST, WinchesterBUDRESKI MARK FREDERICK; BUDRESKI MARK FBUDRESKI MARK F TR; BUDRESKI HANNAH E TRNot disclosed
2026-06-30216 HIGHLAND AVE, WinchesterTOELKE RICHARD A TR; RICHARD A TOELKE TRUSTMEDLINSKY NOAH; MEDLINSKY ELIZABETH$2,400,000
2026-06-3036 CAMBRIDGE ST, WinchesterMCDONALD CONTRACTING LLCHOFFMAN BRADFORD S; HOFFMAN KRISTEN R$2,025,000
2026-06-3012 HANCOCK ST, WinchesterLADOW MARY BETH; PONTRELLI MICHAELPRESLIER HEATHER; KONCZYK DENNIS$1,310,000
2026-07-0160 HOLLAND ST, WinchesterKELLY THOMAS J; KELLY MARGARET SMURRAY ROBERT W TR; HOLLAND STREET NOMINEE TRUST$1,015,000
2026-07-012 ROBINHOOD RD, WinchesterMATTESON PATRICK; MATTESON BARBARAMATTESON PATRICK WILLIAM TR; MATTESON BARBARA ALEKSANDRA TRNot disclosed

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

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