NewOpen house Fri, Oct 30 · 12:00 PM42$1,699,000
4 bd · 3 ba · 2,736 sqft
3 Sunset Road, Winchester, MA
Kim Covino & Co. Team · Compass
Homes for Sale in Winchester, MA
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24 of 55 Listings
NewOpen house Fri, Oct 30 · 12:00 PM42$1,699,000
4 bd · 3 ba · 2,736 sqft
3 Sunset Road, Winchester, MA
Kim Covino & Co. Team · Compass
NewOpen house Sat, Oct 31 · 11:00 AM8$1,049,900
3 bd · 2 ba · 1,783 sqft
28 Olive St, Winchester, MA
Ethan Forrest · The Aland Realty Group LLC
10$2,999,000
5 bd · 5 ba · 4,900 sqft
5 Forest Cir, Winchester, MA
Pirani & Wile Group · Gibson Sotheby's International Realty
Open house Sat, Oct 31 · 11:00 AM32$2,650,000
4 bd · 5 ba · 5,233 sqft
18 Middlesex St, Winchester, MA
Jennifer Taves · Coldwell Banker Realty - Boston
40$3,799,000
8 bd · 6 ba · 7,081 sqft
15 Foxcroft Rd, Winchester, MA
Karen S. Garrett · Better Homes and Gardens Real Estate - The Shanahan Group
41$2,950,000
6 bd · 4 ba · 4,752 sqft
18 Surrey Road, Winchester, MA
Mary Kelly · Century 21 Property Central Inc.
Open house Sun, Nov 1 · 2:00 PM34$890,000
2 bd · 1 ba · 1,489 sqft
80 Nelson St, Winchester, MA
Kim Covino & Co. Team · Compass
Open house Sat, Oct 31 · 12:00 PM34$1,399,000
3 bd · 3 ba · 1,975 sqft
6 Aricia Ln, Winchester, MA
Pirani & Wile Group · Gibson Sotheby's International Realty
Price Reduced42$1,999,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
1$329,900
2 bd · 1 ba · 1,084 sqft
20 Arthur St #20, Winchester, MA
Dan O'Connell Sr · LAER Realty Partners
Price Reduced22$850,000
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
28$3,299,000
7 bd · 8 ba · 7,226 sqft
1 Plymouth Rd., Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
41$700,000
2 bd · 2 ba · 1,240 sqft
666 Main Street #217, Winchester, MA
Elizabeth Darby · Berkshire Hathaway HomeServices Commonwealth Real Estate
Price ReducedOpen house Sun, Nov 1 · 12:00 PM41$1,750,000
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
16$399,000
1 bd · 1 ba · 613 sqft
200 Swanton St #727, Winchester, MA
Alice Zheng · Shore Real Estate LLC
24$495,000
2 bd · 1 ba · 822 sqft
200 Swanton St #303, Winchester, MA
Joseph Pollack · Redfin Corp.
Price Reduced42$2,400,000
6 bd · 4 ba · 3,534 sqft
7 Lakeview Terrace, Winchester, MA
Elizabeth Darby · Berkshire Hathaway HomeServices Commonwealth Real Estate
Open house Sat, Oct 31 · 1:00 PM41$3,200,000
8 bd · 7 ba · 5,750 sqft
30 Willowdale Rd, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
Price Reduced28$1,250,000
4 bd · 3 ba · 2,666 sqft
465 Washington Street, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
Price Reduced28$1,250,000
4 bd · 3 ba · 2,666 sqft
465 Washington Street #465, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
34$974,900
3 bd · 3 ba · 1,719 sqft
258 Cross St, Winchester, MA
Justin Blankenship · Fiv Realty Co
Open house Sun, Nov 1 · 1:00 PM38$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 98.2% of asking price
Buyers here are paying below asking. MLS · 13 sales · as of Sep 30, 2026