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Wednesday, November 4, 2026 Winchester, Massachusetts · Change town
Real Estate

Winchester home sales top out above $3.4 million in latest deed filings

Winchester recorded 19 property transfers at the South Middlesex Registry of Deeds between June 26 and July 25. Of the 11 sales with a disclosed price, figures ranged from $1,015,000 to $3,800,000, with a median of $2,400,000. The month's top sale was 1 Central Green at $3,800,000, foll…

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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

DateAddressGrantorGranteeSale Amount
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
2026-07-011 CENTRAL GREEN, WinchesterKUGELER LIZA M; KUGELER PETER LTHIBEAULT JACOB; THIBEAULT LIZA$3,800,000
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
2026-07-028 TANIA CIR, WinchesterGIAMBRO MICHAELMONAHAN TANIA GIAMBRONot disclosed
2026-07-0234 ROBINHOOD RD, WinchesterMCCABE JOSEPH SR; MCCABE KATEMCCABE JOSEPH PAUL SR; MCCABE KATE NOLAN TRNot disclosed
2026-07-02171 SWANTON ST UNIT 64, WinchesterCRAIG WILLIAM; CRAIG WILLIAM SCRAIG WILLIAM STEPHEN TR; CRAIG ANNA JOY TRNot disclosed
2026-07-0330 WHITE ST, WinchesterFOGEL ERIN DAWN; KAUSHANSKY DAVID RFOGEL ERIN TR; KAUSHANSKY DAVID TRNot disclosed

Jul 6 - Jul 12

DateAddressGrantorGranteeSale Amount
2026-07-0610 BONAD RD, WinchesterAURIELLE H KALLMERTEN TRUST; SAMUEL H KALLMERTEN TRUSTWEBB ARTHUR; WEBB CAROLINE$1,620,000
2026-07-077 CLIFF ST, WinchesterFRIES THOMAS H; FRIES ELIZABETH SANGEVINE FAMILY LIVING TRUST; ANGEVINE CHRISTOPHER TR$2,800,000
2026-07-077 CONANT RD UNIT 54, WinchesterZARRINEGHBAL HOSSEINZARRINEGHBAL HOSSEIN TR; HEARD LISA ANN TRNot disclosed

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

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