Winchester home sales top out above $3.4 million in latest deed filings
WINCHESTER -- Nineteen property transfers recorded at the South Middlesex Registry of Deeds between June 26 and July 25 show a top sale of $3.8 million at 1 Central Green, while eight of the 19 transactions -- all involving family members or family trusts -- carried no disclosed sale price.
MARKET OVERVIEW The registry recorded 19 sales during the period. Of those, 11 included a disclosed sale price, ranging from $1,015,000 to $3,800,000. The median sale price among the 11 disclosed transactions was $2,400,000. By raw count, 19 recorded transfers in a single month is a notable volume for Winchester, though the high share of undisclosed prices -- eight of 19, or 42% -- limits how much can be concluded about overall price levels from this period alone.
TOP SALES The highest-priced transaction was 1 Central Green, which sold for $3,800,000 on July 1; sellers Liza M. and Peter L. Kugeler transferred the property to Jacob and Liza Thibeault. At 50 Oxford St, the sale price was $3,500,000, recorded June 26, with Timothy J. and Nancy L. Clift, as trustees, selling to Joshua Geary and Katherine Johnston. The property at 40 Foxcroft Rd sold for $3,450,000 on June 26, transferred by Foxcroft Realty Trust, with Stefanos Bouboulis as trustee, to Rakshit Kumar and Neha Anand. At 7 Cliff St, Thomas H. and Elizabeth S. Fries sold to the Angevine Family Living Trust, with Christopher Angevine as trustee, for $2,800,000 on July 7. Rounding out the top five, 10 Viking Rd sold for $2,549,000 on June 29, with Mark and Anita Sassi selling to Pia M. Perrone and Brian T. Estaphan.
NEIGHBORHOOD BREAKDOWN Robinhood Road saw two recorded transfers during the period -- 34 Robinhood Rd and 2 Robinhood Rd, both on July 1 and July 2, respectively -- though neither disclosed a sale price and both were transfers between family members into trusts. No other street recorded more than one sale. By price tier among the 11 disclosed sales: two sold under $1.5 million (60 Holland St at $1,015,000 and 12 Hancock St at $1,310,000); two sold between $1.5 million and $2 million (10 Bonad Rd at $1,620,000 and 29 Pilgrim Dr at $1,700,000); four sold between $2 million and $3 million (36 Cambridge St, 216 Highland Ave, 10 Viking Rd and 7 Cliff St); and three sold above $3 million (40 Foxcroft Rd, 50 Oxford St and 1 Central Green).
MARKET NOTES Every one of the eight sales without a disclosed price was a transfer between family members or into a family trust, based on matching or related grantor and grantee names -- including moves at 7 Conant Rd Unit 54, 30 White St, 8 Tania Cir, 34 Robinhood Rd, 171 Swanton St Unit 64, 2 Robinhood Rd, 35 Brooks St and 4 York Rd. By contrast, none of the 11 sales with a disclosed price appear to involve matching grantor and grantee family names. The dataset includes two condominium unit sales -- 7 Conant Rd Unit 54 and 171 Swanton St Unit 64 -- both among the undisclosed-price, family-trust transfers; the remaining 17 records are single-family addresses. Bedroom, bathroom and square-footage figures are not available from deed records for any of the 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 |
|---|---|---|---|---|
| 2026-06-26 | 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 | 1 CENTRAL GREEN, Winchester | KUGELER LIZA M; KUGELER PETER L | THIBEAULT JACOB; THIBEAULT LIZA | $3,800,000 |
| 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 |
| 2026-07-02 | 8 TANIA CIR, Winchester | GIAMBRO MICHAEL | MONAHAN TANIA GIAMBRO | Not disclosed |
| 2026-07-02 | 34 ROBINHOOD RD, Winchester | MCCABE JOSEPH SR; MCCABE KATE | MCCABE JOSEPH PAUL SR; MCCABE KATE NOLAN TR | Not disclosed |
| 2026-07-02 | 171 SWANTON ST UNIT 64, Winchester | CRAIG WILLIAM; CRAIG WILLIAM S | CRAIG WILLIAM STEPHEN TR; CRAIG ANNA JOY TR | Not disclosed |
| 2026-07-03 | 30 WHITE ST, Winchester | FOGEL ERIN DAWN; KAUSHANSKY DAVID R | FOGEL ERIN TR; KAUSHANSKY DAVID TR | Not disclosed |
Jul 6 - Jul 12
| Date | Address | Grantor | Grantee | Sale Amount |
|---|---|---|---|---|
| 2026-07-06 | 10 BONAD RD, Winchester | AURIELLE H KALLMERTEN TRUST; SAMUEL H KALLMERTEN TRUST | WEBB ARTHUR; WEBB CAROLINE | $1,620,000 |
| 2026-07-07 | 7 CLIFF ST, Winchester | FRIES THOMAS H; FRIES ELIZABETH S | ANGEVINE FAMILY LIVING TRUST; ANGEVINE CHRISTOPHER TR | $2,800,000 |
| 2026-07-07 | 7 CONANT RD UNIT 54, Winchester | ZARRINEGHBAL HOSSEIN | ZARRINEGHBAL HOSSEIN TR; HEARD LISA ANN TR | Not disclosed |
Compiled from official town feeds, community organizations, and local press. Outside reporting is attributed inline.