NewOpen house Fri, Oct 9 · 11:00 AM40$2,199,000
6 bd · 5 ba · 4,947 sqft
42 Everett Ave, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
Homes for Sale in Winchester, MA
Hide MapHomes for Sale in Winchester, MA
24 of 62 Listings
NewOpen house Fri, Oct 9 · 11:00 AM40$2,199,000
6 bd · 5 ba · 4,947 sqft
42 Everett Ave, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
NewOpen house Fri, Oct 9 · 11:00 AM42$2,049,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
New1$329,900
2 bd · 1 ba · 1,084 sqft
20 Arthur St #20, Winchester, MA
Dan O'Connell Sr · LAER Realty Partners
NewOpen house Thu, Oct 8 · 4:30 PM39$2,399,000
4 bd · 4 ba · 3,550 sqft
63 Wedgemere Avenue, Winchester, MA
Paula R. Sughrue · Better Homes and Gardens Real Estate - The Shanahan Group
Open house Sat, Oct 10 · 12:00 PM23$899,000
3 bd · 1 ba · 1,313 sqft
39 Henry Street, Winchester, MA
Kelly Batti · Coldwell Banker Realty - Belmont
42$18,000,000
6 bd · 7 ba · 10,000 sqft
15 Vinson Circle, Winchester, MA
Anthony Marino · The Marino Group Collection
Open house Sat, Oct 10 · 1:00 PM28$3,299,000
7 bd · 8 ba · 7,226 sqft
1 Plymouth Rd., Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
Open house Sat, Oct 10 · 12:00 PM32$1,529,000
4 bd · 4 ba · 2,709 sqft
25 Arlington St, Winchester, MA
Domingo Medina · Coldwell Banker Realty - Lexington
38$1,195,000
3 bd · 2 ba · 2,239 sqft
4 Stone Ave, Winchester, MA
The Synergy Group · The Synergy Group
41$700,000
2 bd · 2 ba · 1,240 sqft
666 Main Street #217, Winchester, MA
Elizabeth Darby · Berkshire Hathaway HomeServices Commonwealth Real Estate
Open house Thu, Oct 8 · 4:30 PM41$1,850,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group
Price Reduced26$319,000
1 bd · 1 ba · 602 sqft
200 Swanton St #T14, Winchester, MA
The Synergy Group · The Synergy Group
Open house Sat, Oct 10 · 11:30 AM31$1,325,000
4 bd · 2 ba · 1,922 sqft
9 Priscilla Ln, Winchester, MA
Robert Del Greco · Compass
16$399,000
1 bd · 1 ba · 613 sqft
200 Swanton St #727, Winchester, MA
Alice Zheng · Shore Real Estate LLC
2$1,080,000
3 bd · 1 ba · 1,382 sqft
6 Reservoir Street, Winchester, MA
24$495,000
2 bd · 1 ba · 822 sqft
200 Swanton St #303, Winchester, MA
42$2,600,000
6 bd · 4 ba · 3,534 sqft
7 Lakeview Terrace, Winchester, MA
Elizabeth Darby · Berkshire Hathaway HomeServices Commonwealth Real Estate
42$1,495,000
4 bd · 3 ba · 2,973 sqft
7 Sherman Place #7, Winchester, MA
John Dean · Engel & Volkers Boston
41$3,200,000
8 bd · 7 ba · 5,750 sqft
30 Willowdale Rd, Winchester, MA
42$1,599,000
5 bd · 3 ba · 2,944 sqft
143 Arlington Street, Winchester, MA
Kim Covino & Co. Team · Compass
28$1,300,000
4 bd · 3 ba · 2,666 sqft
465 Washington Street, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
28$1,300,000
4 bd · 3 ba · 2,666 sqft
465 Washington Street #465, Winchester, MA
34$974,900
3 bd · 3 ba · 1,719 sqft
258 Cross St, Winchester, MA
38$4,299,000
5 bd · 6 ba · 6,526 sqft
4 Dartmouth, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
MLS Property Information Network (MLS PIN)Source: HJN community data
September 2026 · This period is still settling
Selling at 98.4% of asking price
Buyers here are paying below asking. MLS · 12 sales · as of Sep 28, 2026