Winchester single-family homes

62 closed sales in 2026 or later. Newest sale September 28, 2026. Median price $1,962,500.

This page is published because the count is at least 8. Sales dated 2022 through 2025 are excluded. Street pages are not generated.

Closed-sale files skip August 2026. Those months are missing from the merge, not a count of zero sales.

• 15 Fieldstone Dr, Winchester, MA 01890

  Winchester 01890 · $1,900,000 · 4 bd / 4 ba · sold September 28, 2026

• 42 Wildwood St, Winchester, MA 01890

  Winchester 01890 · $2,142,000 · 7 bd / 5 ba · sold September 22, 2026

• 53 Winford Way, Winchester, MA 01890

  Winchester 01890 · $2,300,000 · 5 bd / 4 ba · sold September 18, 2026

• 2 Olde Lyme Rd, Winchester, MA 01890

  Winchester 01890 · $1,857,000 · 3 bd / 4 ba · sold September 15, 2026

• 94 Johnson Rd, Winchester, MA 01890

  Winchester 01890 · $1,715,000 · 4 bd / 3 ba · sold September 3, 2026

• 74 Wedgemere Ave, Winchester, MA 01890

  Winchester 01890 · $2,793,000 · 5 bd / 5 ba · sold July 21, 2026

• 2 Eaton Ct, Winchester, MA 01890

  Winchester 01890 · $1,280,000 · 3 bd / 2 ba · sold July 16, 2026

• 27 Everett Ave, Winchester, MA 01890

  Winchester 01890 · $3,100,000 · 6 bd / 6 ba · sold July 15, 2026

• 47 Yale St, Winchester, MA 01890

  Winchester 01890 · $2,600,000 · 6 bd / 5 ba · sold July 15, 2026

• 22 Hollywood Rd, Winchester, MA 01890

  Winchester 01890 · $2,150,000 · 5 bd / 4 ba · sold July 13, 2026

• 49 Sheridan Cir, Winchester, MA 01890

  Winchester 01890 · $2,409,000 · 5 bd / 5 ba · sold July 10, 2026

• 15 Yale St, Winchester, MA 01890

  Winchester 01890 · $2,700,000 · 7 bd / 4 ba · sold July 10, 2026

• 24 Hinds Rd, Winchester, MA 01890

  Winchester 01890 · $1,750,000 · 4 bd / 3 ba · sold July 9, 2026

• 115 Church St, Winchester, MA 01890

  Winchester 01890 · $2,975,000 · 7 bd / 6 ba · sold July 9, 2026

• 36 Cambridge St, Winchester, MA 01890

  Winchester 01890 · $2,025,000 · 5 bd / 5 ba · sold July 9, 2026

• 105 Thornberry Rd, Winchester, MA 01890

  Winchester 01890 · $1,899,000 · 5 bd / 3 ba · sold July 9, 2026

• 4 Lawrence St, Winchester, MA 01890

  Winchester 01890 · $3,070,000 · 6 bd / 8 ba · sold July 7, 2026

• 7 Cliff St, Winchester, MA 01890

  Winchester 01890 · $2,800,000 · 6 bd / 4 ba · sold July 7, 2026

• 10 Bonad Rd, Winchester, MA 01890

  Winchester 01890 · $1,620,000 · 4 bd / 3 ba · sold July 6, 2026

• 12 Hancock St, Winchester, MA 01890

  Winchester 01890 · $1,310,000 · 3 bd / 2 ba · sold June 30, 2026

• 216 Highland Ave, Winchester, MA 01890

  Winchester 01890 · $2,400,000 · 5 bd / 4 ba · sold June 30, 2026

• 71 Sargent Rd, Winchester, MA 01890

  Winchester 01890 · $1,399,000 · 3 bd / 4 ba · sold June 30, 2026

• 29 Pilgrim Dr, Winchester, MA 01890

  Winchester 01890 · $1,700,000 · 5 bd / 3 ba · sold June 29, 2026

• 10 Viking Rd, Winchester, MA 01890

  Winchester 01890 · $2,549,000 · 4 bd / 4 ba · sold June 29, 2026

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