23$498,500
2 bd · 2 ba · 1,002 sqft
1020 Shirley St #1020, Winthrop, MA
Lisa Berry · Simply Sell Realty
2 Bedroom Homes in Winthrop, MA
Hide Map2 Bedroom Homes in Winthrop, MA
24 of 31 Listings
23$498,500
2 bd · 2 ba · 1,002 sqft
1020 Shirley St #1020, Winthrop, MA
Lisa Berry · Simply Sell Realty
21$425,000
2 bd · 1 ba · 861 sqft
29 Seafoam Ave #1, Winthrop, MA
Tom Sheehan · Compass
28$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
10$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 Reduced37$565,995
2 bd · 1 ba · 1,614 sqft
54 Trident Ave #54, Winthrop, MA
Candice Pagliarulo Hodgson · Lyv Realty
29$637,900
2 bd · 2 ba · 1,233 sqft
10 Somerset #307, Winthrop, MA
Charlesgate New Development Team · Charlesgate Realty Group, llc
30$679,900
2 bd · 1 ba · 1,144 sqft
7 Enfield Road, Winthrop, MA
Nicholas Martino · Noddle Island Real Estate
Price Reduced25$449,900
2 bd · 1 ba · 805 sqft
43 Sagamore Ave #1, Winthrop, MA
Katelyn E. Sullivan · Coldwell Banker Realty - Boston
24$699,900
2 bd · 2 ba · 1,113 sqft
130 Shirley Street #250, Winthrop, MA
Kovacs Team · Compass
14$815,000
2 bd · 3 ba · 1,665 sqft
1001 Shirley St #4, Winthrop, MA
Vincenzo Caraglia · Sciaraffa Real Estate, LLC
18$549,900
2 bd · 1 ba · 782 sqft
130 Shirley Street #220, Winthrop, MA
Kovacs Team · Compass
16$965,000
2 bd · 3 ba · 1,978 sqft
1001 Shirley St #1, Winthrop, MA
Vincenzo Caraglia · Sciaraffa Real Estate, LLC
Price Reduced17$465,000
2 bd · 2 ba · 903 sqft
34 Underhill Street #4, Winthrop, MA
Reserve Team · Reference Real Estate
42$1,095,000
2 bd · 3 ba · 2,649 sqft
94 Winthrop Shore Dr, Winthrop, MA
The Movement Group · Compass
28$699,999
2 bd · 2 ba · 1,417 sqft
1 Seal Harbor #916, Winthrop, MA
Meg Grady · The Persac Group, LLC
Price Reduced21$575,000
2 bd · 2 ba · 912 sqft
194 Washington Ave #2, Winthrop, MA
Ella Goren · Sunrise Realty & Investment LLC
Price Reduced18$540,000
2 bd · 2 ba · 756 sqft
194 Washington Ave #4, Winthrop, MA
Ella Goren · Sunrise Realty & Investment LLC
Price Reduced29$660,000
2 bd · 2 ba · 1,192 sqft
550 Pleasant St #201, Winthrop, MA
John Young · Ledge & Young Real Estate
Price Reduced32$499,900
2 bd · 3 ba · 1,210 sqft
15 Ocean Ave #203, Winthrop, MA
Kenneth Celano · Turn Key Realty
Price ReducedOpen house Sat, Oct 24 · 11:00 AM18$529,900
2 bd · 2 ba · 969 sqft
35 Somerset Ave #3a, Winthrop, MA
Mark Savage · Byrnes Real Estate Group LLC
22$865,000
2 bd · 3 ba · 1,806 sqft
1001 Shirley St #2, Winthrop, MA
Vincenzo Caraglia · Sciaraffa Real Estate, LLC
Price Reduced40$549,999
2 bd · 2 ba · 1,205 sqft
1 Seal Harbor Rd #413, Winthrop, MA
Tammy Merk · Real Broker MA, LLC
14$350,000
2 bd · 1 ba · 649 sqft
175 Shirley Street #5, Winthrop, MA
Tammy Merk · Real Broker MA, LLC
2 Bedroom Homes in Winthrop, MA: 31 active listings as of .
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