41$1,399,000
5 bd · 2 ba · 2,071 sqft
15 Lloyd Street, Winchester, MA
Kim Covino & Co. Team · Compass
Luxury Homes in Winchester, MA
Hide MapLuxury Homes in Winchester, MA
24 of 43 Listings
41$1,399,000
5 bd · 2 ba · 2,071 sqft
15 Lloyd Street, Winchester, MA
Kim Covino & Co. Team · Compass
38$1,299,000
3 bd · 2 ba · 2,350 sqft
39 Forest St, Winchester, MA
Danielle Storella · Berkshire Hathaway HomeServices Commonwealth Real Estate
40$2,199,000
6 bd · 5 ba · 4,947 sqft
42 Everett Ave, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
42$2,049,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
39$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
42$18,000,000
6 bd · 7 ba · 10,000 sqft
15 Vinson Circle, Winchester, MA
Anthony Marino · The Marino Group Collection
28$3,299,000
7 bd · 8 ba · 7,226 sqft
1 Plymouth Rd., Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
32$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
40$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
31$1,325,000
4 bd · 2 ba · 1,922 sqft
9 Priscilla Ln, Winchester, MA
Robert Del Greco · Compass
2$1,080,000
3 bd · 1 ba · 1,382 sqft
6 Reservoir Street, Winchester, MA
Dongjun Lou · HMW Real Estate, LLC
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
The Pallotta Group · Gibson Sotheby's International Realty
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
The Pallotta Group · Gibson Sotheby's International Realty
38$4,299,000
5 bd · 6 ba · 6,526 sqft
4 Dartmouth, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
42$1,650,000
5 bd · 4 ba · 3,722 sqft
117 Highland, Winchester, MA
Dara Singleton · Better Homes and Gardens Real Estate - The Shanahan Group
40$2,199,000
4 bd · 4 ba · 3,570 sqft
19 Hancock Street, Winchester, MA
Vita Realty Group · Compass
42$3,149,000
7 bd · 8 ba · 8,540 sqft
37 Mayflower Road, Winchester, MA
Kim Covino & Co. Team · Compass
37$1,749,000
5 bd · 4 ba · 3,508 sqft
17 Churchill Rd, Winchester, MA
Domingo Medina · Coldwell Banker Realty - Lexington
Price Reduced42$1,649,000
3 bd · 2 ba · 2,421 sqft
4 Churchill Road, Winchester, MA
Kim Covino & Co. Team · Compass
Price Reduced40$1,069,000
4 bd · 3 ba · 2,411 sqft
24 Richardson St, Winchester, MA
Andersen Group Realty · Keller Williams Realty Boston Northwest
Luxury Homes in Winchester, MA: 43 active listings as of .
MLS Property Information Network (MLS PIN)Source: HJN community data
September 2026 · This period is still settling
Selling at 98.2% of asking price
Buyers here are paying below asking. MLS · 13 sales · as of Sep 30, 2026