Winchester Home Prices Hold Above $1M Floor as Three Sales Top $3 Million
WINCHESTER -- The local residential market recorded 17 deed transfers between May 28 and June 26, 2026, with 13 carrying disclosed prices and three transactions reaching or exceeding $3 million -- signaling sustained demand at the upper end of the market.
- MARKET OVERVIEW
- Thirteen of the 17 recorded transfers included a stated consideration, yielding a price range of $1,030,000 to $3,150,000 and a median sale price of $1,300,000. The four remaining transfers were price not disclosed, a standard occurrence in deed records. Seventeen total transactions over roughly a month represents a moderately active recording period for a single municipality. All disclosed sales cleared the $1 million mark, underscoring a price floor that has become characteristic of Winchester's market in recent years -- though this dataset alone does not support a trend comparison.
- TOP SALES
- The month's highest recorded price belonged to 257 High St., which sold May 28 for $3,150,000. Sellers Joseph A. Piantedosi Jr. and Julie A. Piantedosi conveyed the property to buyers Joseph P. Repp and Jennifer L. Repp, both acting as trustees. Two properties tied for second place at $3,100,000: 12 Salisbury St., which transferred June 1 from Mary W. Siciliano to John P. and Janet Riley, and 54 Johnson Rd., which sold May 29 with Carrie A. Boyd as seller and Subramanian Murugan and Subha Sellimuthu as buyers. Rounding out the top five, 6 Oakland Cir. sold June 1 for $1,607,000, transferring from the Ali Family Nominee Trust to Robert James Murphy and Kate Sherman Murphy, both acting as trustees; and 65 High St. changed hands the same day for $1,440,150, with Jon Paul Trudeau and Jeong Suk Lee selling to Di Liang and Chen Ji.
- NEIGHBORHOOD BREAKDOWN
- Two streets each accounted for more than one disclosed sale. High Street produced two transactions at opposite ends of the price spectrum -- 257 High St. at $3,150,000 and 65 High St. at $1,440,150 -- reflecting the variation that can exist within a single corridor. Salisbury Street similarly saw two sales: 12 Salisbury St. at $3,100,000 and 71 Salisbury St. at $1,270,000. East Street contributed two adjacent addresses: 15 East St. at $1,060,000 and 17 East St. at $1,030,000, the dataset's lowest disclosed prices. Wendell Street also recorded two sales -- 87 Wendell St. at $1,250,000 and 104 Wendell St. at $1,100,000 -- clustering in the lower-middle tier of the month's range. The remaining disclosed sales -- 368 S. Border Rd. ($1,300,000), 1 Orient St. ($1,330,000), and 31 Mystic Ave. Unit 2 ($1,200,000) -- were distributed across separate streets with no additional clustering.
- MARKET NOTES
- Of the 13 disclosed-price transfers, all fell between $1,030,000 and $3,150,000, with no sale below seven figures. The dataset includes at least one condominium unit (31 Mystic Ave. Unit 2, $1,200,000) and one other unit-style address (18 Graystone Cir. Unit 18, price not disclosed), suggesting a mix of property types, though deed records do not specify property classification. Four of the 17 transfers -- entries involving the Ain Family Living Trust, the Grimes Revocable Family trust, the Johnson Dawn M. revocable trust, and the Lillian Laffan Irrevocable Trust -- appear to be intra-family or estate-related conveyances based on shared surnames and trust language; no prices were disclosed for any of those four. Bed, bath, and square footage data are not available from deed records.