40 total properties
View 960 Shirley St Winthrop, MA MLS# 73453149
$705,000
3

Beds

1.1

Baths

1,764

Sq.Ft.

960 Shirley St

Winthrop, MA

Listed By: Bridget Conroy Courtesy of COLDWELL BANKER REALTY - MILTON
View 140 Shirley Street # 310 Winthrop, MA MLS# 73478497
  • Recently Listed
1 of 23
$749,900
2

Beds

2.0

Baths

1,113

Sq.Ft.

140 Shirley Street # 310

Winthrop, MA

Listed By: Kovacs Savage Team Courtesy of BYRNES REAL ESTATE GROUP LLC
View 62 Cottage Ave Winthrop, MA MLS# 73466507
$799,000
5

Beds

2.0

Baths

1,655

Sq.Ft.

62 Cottage Ave

Winthrop, MA

Listed By: Michelle Pena Courtesy of PENA REALTY CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
View 56 Main Street Winthrop, MA MLS# 73460239
$799,900
4

Beds

2.0

Baths

2,103

Sq.Ft.

56 Main Street

Winthrop, MA

Listed By: Sharon Tallent Courtesy of COMPASS
View 876 Shirley # 1 Winthrop, MA MLS# 73470875
$849,999
4

Beds

2.0

Baths

2,000

Sq.Ft.

876 Shirley # 1

Winthrop, MA

Listed By: James Iannuzzi Courtesy of AMO REALTY - BOSTON CITY PROPERTIES
View 1001 Shirley # 3 Winthrop, MA MLS# 73441432
$939,900
2

Beds

2.1

Baths

1,551

Sq.Ft.

1001 Shirley # 3

Winthrop, MA

Listed By: Reserve Team Courtesy of REFERENCE REAL ESTATE
View 550 Pleasant St # 506 Winthrop, MA MLS# 73456380
$1,030,000
2

Beds

2.0

Baths

1,975

Sq.Ft.

550 Pleasant St # 506

Winthrop, MA

Listed By: Jessica Pumphret Courtesy of BLUE SKY REALTY
View 1001 Shirley # 5 Winthrop, MA MLS# 73466792
$1,050,000
2

Beds

2.1

Baths

1,785

Sq.Ft.

1001 Shirley # 5

Winthrop, MA

Listed By: Reserve Team Courtesy of REFERENCE REAL ESTATE
View 1001 Shirley # 1 Winthrop, MA MLS# 73441435
$1,125,000
2

Beds

2.1

Baths

1,978

Sq.Ft.

1001 Shirley # 1

Winthrop, MA

Listed By: Reserve Team Courtesy of REFERENCE REAL ESTATE
View 22 Upland Road Winthrop, MA MLS# 73473241
  • Recently Listed
1 of 14
$1,250,000
6

Beds

3.1

Baths

4,062

Sq.Ft.

22 Upland Road

Winthrop, MA

Listed By: Mary Ann Cash Courtesy of CHARLESGATE REALTY GROUP, LLC
View 47 Bellevue Ave Winthrop, MA MLS# 73460507
$1,280,000
6

Beds

3.1

Baths

3,093

Sq.Ft.

47 Bellevue Ave

Winthrop, MA

Listed By: Jessica Pumphret Courtesy of BLUE SKY REALTY
View 37 Trident Ave Winthrop, MA MLS# 73457896
$1,300,000
8

Beds

3.0

Baths

3,708

Sq.Ft.

37 Trident Ave

Winthrop, MA

Listed By: David Parish Courtesy of CONNOR REAL ESTATE
View 10-12 Charles St Winthrop, MA MLS# 73475129
  • Recently Listed
1 of 15
$1,300,000
7

Beds

4.0

Baths

3,688

Sq.Ft.

10-12 Charles St

Winthrop, MA

Listed By: Reserve Team Courtesy of REFERENCE REAL ESTATE
View 129 Strandway Winthrop, MA MLS# 73452093
$1,324,900
4

Beds

3.0

Baths

2,640

Sq.Ft.

129 Strandway

Winthrop, MA

Listed By: Kovacs Savage Team Courtesy of BYRNES REAL ESTATE GROUP LLC
View 86N Undine Ave Winthrop, MA MLS# 73462992
$1,350,000
3

Beds

2.1

Baths

2,250

Sq.Ft.

86N Undine Ave

Winthrop, MA

Listed By: Reserve Team Courtesy of REFERENCE REAL ESTATE
View 144 Quincy Ave Winthrop, MA MLS# 73458915
  • Virtual Tour
1 of 39
$1,699,900
5

Beds

4.0

Baths

3,866

Sq.Ft.

144 Quincy Ave

Winthrop, MA

Listed By: Leighann Eruzione Courtesy of LANTERN RESIDENTIAL
View 144 Quincy Ave Winthrop, MA MLS# 73458947
  • Virtual Tour
1 of 41
$1,699,900
5

Beds

4.0

Baths

3,866

Sq.Ft.

144 Quincy Ave

Winthrop, MA

Listed By: Leighann Eruzione Courtesy of LANTERN RESIDENTIAL
View 201 Cliff Avenue Winthrop, MA MLS# 73465296
$1,785,000
8

Beds

6.1

Baths

5,362

Sq.Ft.

201 Cliff Avenue

Winthrop, MA

Listed By: Constance Doto Courtesy of CONNIE DOTO REALTY GROUP
View 191 Cottage Park Road Winthrop, MA MLS# 73424484
$1,799,000
6

Beds

3.1

Baths

4,455

Sq.Ft.

191 Cottage Park Road

Winthrop, MA

Listed By: Anthony Giacalone Jr. Courtesy of TONY'S REALTY
View 155-165 Shirley St Winthrop, MA MLS# 73473145
$4,000,000
10,386

Sq.Ft.

155-165 Shirley St

Winthrop, MA

Listed By: Joshua Seadia Courtesy of JMJ COMMERCIAL REALTY, INC.

Information deemed reliable but not guaranteed.

Content © 2026 MLS Property Information Network, Inc. All Rights Reserved.

Data is updated as of 2/20/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.