New23$498,500
2 bd · 2 ba · 1,002 sqft
1020 Shirley St #1020, Winthrop, MA
Lisa Berry · Simply Sell Realty
Homes for Sale in Winthrop, MA
Hide MapHomes for Sale in Winthrop, MA
24 of 69 Listings
New23$498,500
2 bd · 2 ba · 1,002 sqft
1020 Shirley St #1020, Winthrop, MA
Lisa Berry · Simply Sell Realty
NewOpen house Sun, Oct 18 · 11:00 AM21$425,000
2 bd · 1 ba · 861 sqft
29 Seafoam Ave #1, Winthrop, MA
Tom Sheehan · Compass
New26$519,000
3 bd · 1 ba · 1,374 sqft
23 Trident #1, Winthrop, MA
Devon Previte · Blue Sky Realty
Open house Sun, Oct 18 · 11:30 AM26$665,000
3 bd · 2 ba · 1,413 sqft
14 Irwin St, Winthrop, MA
Brian Perrin · Brian J. Perrin Real Estate
Open house Sat, Oct 17 · 11:30 AM26$599,900
1 bd · 1 ba · 1,005 sqft
1 Seal Harbor Rd #601, Winthrop, MA
Colleen Eddy · Return Realty Group, Inc.
Open house Sat, Oct 17 · 11:30 AM17$449,900
1 bd · 1 ba · 623 sqft
130 Shirley Street #8, Winthrop, MA
Kovacs Team · Compass
39$799,900
5 bd · 3 ba · 2,437 sqft
43 Dolphin Ave, Winthrop, MA
Patricia Nunez · Redfin Corp.
Open house Sat, Oct 17 · 11:30 AM32$491,900
1 bd · 1 ba · 691 sqft
10 Somerset #205, Winthrop, MA
Charlesgate New Development Team · Charlesgate Realty Group, llc
Open house Sat, Oct 17 · 12:00 PM28$540,000
2 bd · 2 ba · 1,295 sqft
15 Ocean #206, Winthrop, MA
Renee Spaulding · Better Homes and Gardens Real Estate - The Shanahan Group
34$1,275,000
4 bd · 3 ba · 2,599 sqft
129 Strandway, Winthrop, MA
Kyle MacNichol · Redfin Corp.
Open house Sat, Oct 17 · 10:00 AM10$569,000
2 bd · 1 ba · 1,692 sqft
16 Loring Rd., Winthrop, MA
Martin Tokos · Coldwell Banker First Quality Realty
30$349,900
2 bd · 1 ba · 811 sqft
900 Governors Dr #37, Winthrop, MA
Brandon Dervishian · Lyv Realty
Price ReducedOpen house Sun, Oct 18 · 1:30 PM37$565,995
2 bd · 1 ba · 1,614 sqft
54 Trident Ave #54, Winthrop, MA
Candice Pagliarulo Hodgson · Lyv Realty
Open house Sat, Oct 17 · 11:30 AM29$637,900
2 bd · 2 ba · 1,233 sqft
10 Somerset #307, Winthrop, MA
Charlesgate New Development Team · Charlesgate Realty Group, llc
Price ReducedOpen house Sun, Oct 18 · 11:00 AM40$839,900
4 bd · 2 ba · 1,942 sqft
32 Elmwood Avenue, Winthrop, MA
Edward Deveau · Century 21 Mario Real Estate
Price ReducedOpen house Sun, Oct 18 · 11:00 AM15$249,000
1 bd · 1 ba · 664 sqft
100 Governors Drive #2, Winthrop, MA
Pat Sullivan · Century 21 Seaport
30$679,900
2 bd · 1 ba · 1,144 sqft
7 Enfield Road, Winthrop, MA
Nicholas Martino · Noddle Island Real Estate
Open house Sat, Oct 17 · 11:30 AM32$555,900
1 bd · 1 ba · 848 sqft
10 Somerset #210, Winthrop, MA
Charlesgate New Development Team · Charlesgate Realty Group, llc
Price ReducedOpen house Sat, Oct 17 · 11:00 AM25$449,900
2 bd · 1 ba · 805 sqft
43 Sagamore Ave #1, Winthrop, MA
Katelyn E. Sullivan · Coldwell Banker Realty - Boston
Open house Sat, Oct 17 · 11:30 AM24$699,900
2 bd · 2 ba · 1,113 sqft
130 Shirley Street #250, Winthrop, MA
Kovacs Team · Compass
Open house Sun, Oct 18 · 1:00 PM14$815,000
2 bd · 3 ba · 1,665 sqft
1001 Shirley St #4, Winthrop, MA
Vincenzo Caraglia · Sciaraffa Real Estate, LLC
Open house Sat, Oct 17 · 11:30 AM18$549,900
2 bd · 1 ba · 782 sqft
130 Shirley Street #220, Winthrop, MA
Kovacs Team · Compass
Open house Sun, Oct 18 · 1:00 PM16$965,000
2 bd · 3 ba · 1,978 sqft
1001 Shirley St #1, Winthrop, MA
Vincenzo Caraglia · Sciaraffa Real Estate, LLC
Price Reduced12$299,900
1 bd · 1 ba · 720 sqft
483 Shirley St. #6a, Winthrop, MA
Sharon Tallent · Compass
MLS Property Information Network (MLS PIN)Source: HJN community data
September 2026 · This period is still settling
Selling at 98.3% of asking price
Buyers here are paying below asking. MLS · 17 sales · as of Sep 30, 2026