NewOpen house Thu, Oct 29 · 5:30 PM8$1,049,900
3 bd · 2 ba · 1,783 sqft
28 Olive St, Winchester, MA
Ethan Forrest · The Aland Realty Group LLC
Luxury Homes in Winchester, MA
Hide MapLuxury Homes in Winchester, MA
24 of 38 Listings
NewOpen house Thu, Oct 29 · 5:30 PM8$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
32$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.
42$1,985,000
4 bd · 4 ba · 4,241 sqft
30 Surrey Rd, Winchester, MA
Anne Spry · Barrett Sotheby's International Realty
34$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
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
Price Reduced40$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
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
41$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
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
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
40$2,199,000
4 bd · 4 ba · 3,570 sqft
19 Hancock Street, Winchester, MA
Vita Realty Group · Compass
Price Reduced42$1,599,000
4 bd · 2 ba · 2,421 sqft
4 Churchill Road, Winchester, MA
Kim Covino & Co. Team · Compass
Price Reduced40$1,049,000
4 bd · 3 ba · 2,411 sqft
24 Richardson St, Winchester, MA
Andersen Group Realty · Keller Williams Realty Boston Northwest
40$1,050,000
5 bd · 3 ba · 2,801 sqft
257 Cross Street, Winchester, MA
Kim Covino & Co. Team · Compass
Luxury Homes in Winchester, MA: 38 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