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
| Date | Address | Grantor | Grantee | Sale Amount |
|---|---|---|---|---|
| 2026-06-22 | 18 MYSTIC AVE, Winchester | SALIBA ESTEPHEN; SALIBA EMMA | SPINALE STEVEN C; BEAL PERRY E | $2,229,000 |
| 2026-06-22 | 7 WAINWRIGHT RD UNIT 30, Winchester | REVOCABLE TRUST; SHANAHAN NANNETTE J TR | BALANON CHRISTINA; SWOBODZINSKI KAMIL | $1,350,000 |
| 2026-06-22 | 200 SWANTON ST UNIT 538, Winchester | FIRST BAY REALTY LLC | XIANG LIPING | $250,000 |
| 2026-06-22 | 42 EVERETT AVE, Winchester | CURTIS GEOFFREY A TR; ODONNELL LEAH K TR | ODONNELL LOUISE J TR; ODONNELL MARTIN J TR | Not disclosed |
| 2026-06-23 | 56 YALE ST, Winchester | ROBINSON MARK; ROBINSON GAEL D | VINEBURGH PHILIP L T; VINEBURGH MOLLY C | $2,830,000 |
| 2026-06-23 | 16 PLATO TER, Winchester | ALTARAS NEDIM EMIL; ALTARAS GINA M | BIEL STACIA; BIEL WYATT | $2,300,000 |
| 2026-06-24 | 8 POCAHONTAS DR, Winchester | SCHWARTZMAN THOMAS N; SCHWARTZMAN TOBY J | SCHWARTZMAN THOMAS N TR; SCHWARTZMAN TOBY J TR | Not disclosed |
| 2026-06-25 | Winchester | AFT LTD LP; ANNINO DONALD J JR TR | PEDIATRICIANS REALTY LLC | $1,460,000 |
| 2026-06-25 | 5 EMERSON CT, Winchester | YAO YING | YAO YING TR; YE CHANG TR | Not disclosed |
| 2026-06-26 | 50 OXFORD ST, Winchester | CLIFT TIMOTHY J TR; CLIFT NANCY L TR | GEARY JOSHUA; JOHNSTON KATHERINE | $3,500,000 |
| 2026-06-26 | 40 FOXCROFT RD, Winchester | FOXCROFT REALTY TRUST; BOUBOULIS STEFANOS TR | KUMAR RAKSHIT; ANAND NEHA | $3,450,000 |
| 2026-06-26 | 4 YORK RD, Winchester | TULLY KEVIN R; TULLY KATHERINE E | TULLY KATHERINE E | Not disclosed |
Jun 29 - Jul 5
| Date | Address | Grantor | Grantee | Sale Amount |
|---|---|---|---|---|
| 2026-06-29 | 10 VIKING RD, Winchester | SASSI MARK; SASSI ANITA | PERRONE PIA M; ESTAPHAN BRIAN T | $2,549,000 |
| 2026-06-29 | 29 PILGRIM DR, Winchester | GENTUSO JOHN L; GENTUSO KAREN | MARTIN JOHN JR; DEPAOLO KRISTEN | $1,700,000 |
| 2026-06-29 | 35 BROOKS ST, Winchester | BUDRESKI MARK FREDERICK; BUDRESKI MARK F | BUDRESKI MARK F TR; BUDRESKI HANNAH E TR | Not disclosed |
| 2026-06-30 | 216 HIGHLAND AVE, Winchester | TOELKE RICHARD A TR; RICHARD A TOELKE TRUST | MEDLINSKY NOAH; MEDLINSKY ELIZABETH | $2,400,000 |
| 2026-06-30 | 36 CAMBRIDGE ST, Winchester | MCDONALD CONTRACTING LLC | HOFFMAN BRADFORD S; HOFFMAN KRISTEN R | $2,025,000 |
| 2026-06-30 | 12 HANCOCK ST, Winchester | LADOW MARY BETH; PONTRELLI MICHAEL | PRESLIER HEATHER; KONCZYK DENNIS | $1,310,000 |
| 2026-07-01 | 60 HOLLAND ST, Winchester | KELLY THOMAS J; KELLY MARGARET S | MURRAY ROBERT W TR; HOLLAND STREET NOMINEE TRUST | $1,015,000 |
| 2026-07-01 | 2 ROBINHOOD RD, Winchester | MATTESON PATRICK; MATTESON BARBARA | MATTESON PATRICK WILLIAM TR; MATTESON BARBARA ALEKSANDRA TR | Not disclosed |
Compiled from official town feeds, community organizations, and local press. Outside reporting is attributed inline.