141 Homes for Sale in Winthrop
$2,380,000
5
Beds
5/1
Baths
6,224
Sqft
174 Bartlett Road
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$1,450,000
6
Beds
5/1
Baths
5,278
Sqft
100 Sargent Street
Winthrop, MA 02152
Year Built:
1910
HOA:
None
$1,399,000
4
Beds
2/1
Baths
2,475
Sqft
89r Upland Rd
Winthrop, MA 02152
Year Built:
1930
HOA:
None
$1,324,900
4
Beds
3
Baths
2,640
Sqft
129 Strandway Way
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$1,230,000
3
Beds
3
Baths
1,913
Sqft
3 Seal Harbor Rd #PH33
Winthrop, MA 02152
Year Built:
1987
HOA:
None
$1,199,999
4
Beds
3/1
Baths
1,904
Sqft
70 Edgehill Rd
Winthrop, MA 02152
Year Built:
1930
HOA:
None
$999,000
6
Beds
2/1
Baths
3,263
Sqft
217 Pleasant Street
Winthrop, MA 02152
Year Built:
1896
HOA:
None
$998,900
6
Beds
2/1
Baths
3,263
Sqft
217 Pleasant Street
Winthrop, MA 02152
Year Built:
1896
HOA:
None
$975,000
3
Beds
2/1
Baths
2,100
Sqft
200 Main St #1
Winthrop, MA 02152
Year Built:
2026
HOA:
None
$939,900
3
Beds
1/1
Bath
2,371
Sqft
43 Loring Rd
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$899,900
2
Beds
2/1
Baths
1,806
Sqft
1001 Shirley St #2
Winthrop, MA 02152
Year Built:
1955
HOA:
None
$895,000
4
Beds
2
Baths
1,755
Sqft
118 Sunnyside Ave
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$895,000
4
Beds
3
Baths
2,204
Sqft
23 Sagamore Ave
Winthrop, MA 02152
Year Built:
1895
HOA:
None
$869,900
3
Beds
2/1
Baths
2,125
Sqft
37 Loring Rd
Winthrop, MA 02152
Year Built:
1910
HOA:
None
$865,000
2
Beds
2/1
Baths
1,806
Sqft
1001 Shirley St #2
Winthrop, MA 02152
Year Built:
1955
HOA:
None
$859,900
2
Beds
1/1
Bath
1,674
Sqft
3 Seal Harbor #336
Winthrop, MA 02152
Year Built:
1987
HOA:
None
$849,900
2
Beds
2/1
Baths
1,551
Sqft
1001 Shirley #3
Winthrop, MA 02152
Year Built:
1955
HOA:
None
$840,000
3
Beds
2/1
Baths
1,837
Sqft
27 Billows St
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$829,900
5
Beds
2/1
Baths
2,437
Sqft
43 Dolphin Ave
Winthrop, MA 02152
Year Built:
1946
HOA:
None
$799,999
4
Beds
1/1
Bath
2,000
Sqft
876 Shirley Street #1
Winthrop, MA 02152
Year Built:
1910
HOA:
None
$799,000
4
Beds
4
Baths
2,910
Sqft
26 George St
Winthrop, MA 02152
Year Built:
1930
HOA:
None
$779,000
3
Beds
3
Baths
1,996
Sqft
55 Banks St #2
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$775,000
2
Beds
2
Baths
1,417
Sqft
1 Seal Harbor #PH16
Winthrop, MA 02152
Year Built:
1983
HOA:
None
$765,000
4
Beds
2/1
Baths
1,933
Sqft
546 Shirley St
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$764,000
3
Beds
2/1
Baths
1,800
Sqft
189 Shirley St #1
Winthrop, MA 02152
Year Built:
1890
HOA:
None
$758,000
3
Beds
2/1
Baths
1,800
Sqft
189 Shirley St #1
Winthrop, MA 02152
Year Built:
1890
HOA:
None
$750,000
4
Beds
2/1
Baths
2,700
Sqft
546 Shirley St
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$739,000
3
Beds
2
Baths
1,428
Sqft
8 Siren St
Winthrop, MA 02152
Year Built:
1950
HOA:
None
$725,000
2
Beds
2
Baths
1,113
Sqft
140 Shirley Street #250
Winthrop, MA 02152
Year Built:
2026
HOA:
None
$715,000
4
Beds
1/1
Bath
1,586
Sqft
52 Pebble Ave
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$710,000
4
Beds
2
Baths
1,193
Sqft
542 Shirley St
Winthrop, MA 02152
Year Built:
1890
HOA:
None
$675,000
3
Beds
2/1
Baths
1,510
Sqft
189 Shirley St #2
Winthrop, MA 02152
Year Built:
1890
HOA:
None
$669,999
3
Beds
1
Bath
1,250
Sqft
51 Undine Ave
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$659,000
2
Beds
2/1
Baths
1,800
Sqft
21 Hutchinson St #1
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$650,000
1
Bed
2
Baths
1,263
Sqft
3 Seal Harbor Rd #632
Winthrop, MA 02152
Year Built:
1987
HOA:
None
$650,000
3
Beds
1
Bath
931
Sqft
33 Bay View Ave
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$650,000
3
Beds
2
Baths
800
Sqft
496 Winthrop St
Winthrop, MA 02152
Year Built:
1960
HOA:
None
$649,000
2
Beds
2
Baths
1,024
Sqft
10 Somerset Ave #402
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$649,000
3
Beds
1/1
Bath
1,200
Sqft
84 Tafts Ave
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$639,000
2
Beds
2
Baths
1,302
Sqft
3 Seal Harbor Road #342
Winthrop, MA 02152
Year Built:
1987
HOA:
None
$629,000
2
Beds
2/1
Baths
1,463
Sqft
21 Hutchinson St #2
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$629,000
2
Beds
2
Baths
985
Sqft
10 Somerset Ave #406
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$629,000
2
Beds
2/1
Baths
1,360
Sqft
21 Hutchinson Street #B
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$615,000
2
Beds
2
Baths
1,203
Sqft
1 Seal Harbor Rd #815
Winthrop, MA 02152
Year Built:
1983
HOA:
None
$599,999
2
Beds
2
Baths
1,203
Sqft
1 Seal Harbor Rd #615
Winthrop, MA 02152
Year Built:
1983
HOA:
None
$599,000
3
Beds
1/1
Bath
1,728
Sqft
47 Highland Ave
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$595,000
2
Beds
1/1
Bath
1,141
Sqft
142 Pleasant Street #12
Winthrop, MA 02152
Year Built:
2017
HOA:
None
$589,900
2
Beds
1
Bath
782
Sqft
140 Shirley Street #220
Winthrop, MA 02152
Year Built:
2025
HOA:
None
$579,000
2
Beds
2
Baths
1,205
Sqft
1 Seal Harbor Rd #413
Winthrop, MA 02152
Year Built:
1983
HOA:
None
$569,000
3
Beds
1
Bath
1,377
Sqft
10 Beach Rd #1
Winthrop, MA 02152
Year Built:
1881
HOA:
None
$565,000
2
Beds
1
Bath
928
Sqft
16 Billows St #2
Winthrop, MA 02152
Year Built:
1890
HOA:
None
$555,000
2
Beds
2
Baths
874
Sqft
12 Sewall Ave #2B
Winthrop, MA 02152
Year Built:
1925
HOA:
None
$549,999
2
Beds
2
Baths
1,205
Sqft
1 Seal Harbor Rd #413
Winthrop, MA 02152
Year Built:
1983
HOA:
None
$549,000
2
Beds
1
Bath
869
Sqft
10 Somerset Ave #203
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$549,000
3
Beds
1
Bath
1,788
Sqft
283 Revere St #2
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$549,000
2
Beds
1
Bath
928
Sqft
16 Billows Street #B
Winthrop, MA 02152
Year Built:
1890
HOA:
None
$545,000
2
Beds
2
Baths
969
Sqft
35 Somerset Ave #3
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$539,000
1
Bed
1
Bath
1,368
Sqft
60 Hermon St #3
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$519,000
1
Bed
1
Bath
974
Sqft
1 Seal Harbor Rd #812
Winthrop, MA 02152
Year Built:
1983
HOA:
None
$509,000
1
Bed
1
Bath
729
Sqft
10 Somerset Ave #309
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$505,000
1
Bed
1
Bath
693
Sqft
10 Somerset Ave #305
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$499,900
1
Bed
1
Bath
623
Sqft
140 Shirley Street #330
Winthrop, MA 02152
Year Built:
2026
HOA:
None
$499,900
1
Bed
1
Bath
947
Sqft
1 Seal Harbor #210
Winthrop, MA 02152
Year Built:
1983
HOA:
None
$499,000
2
Beds
1
Bath
1,006
Sqft
52 Trident Ave #52
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$499,000
1
Bed
1
Bath
683
Sqft
10 Somerset Ave #U405
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$489,900
1
Bed
1
Bath
947
Sqft
1 Seal Harbor #210
Winthrop, MA 02152
Year Built:
1983
HOA:
None
$485,000
1
Bed
1/1
Bath
591
Sqft
600 Shirley St #7
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$485,000
2
Beds
1
Bath
913
Sqft
43 Sagamore Ave #1A
Winthrop, MA 02152
Year Built:
1950
HOA:
None
$479,900
2
Beds
1
Bath
1,056
Sqft
2 Edgar Terrace #3
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$459,900
2
Beds
1
Bath
1,153
Sqft
92 Lincoln Street #2
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$449,900
2
Beds
2
Baths
879
Sqft
34r Underhill St #3
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$419,900
1
Bed
1
Bath
525
Sqft
22 Pauline St #5
Winthrop, MA 02152
Year Built:
2026
HOA:
None
$399,900
1
Bed
1
Bath
500
Sqft
22 Pauline St #3
Winthrop, MA 02152
Year Built:
2026
HOA:
None
$399,900
2
Beds
1
Bath
664
Sqft
53 Trident Ave #303
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$399,000
1
Bed
1
Bath
546
Sqft
10 Somerset Ave #304
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$399,000
1
Bed
1
Bath
546
Sqft
10 Somerset Ave #U304
Winthrop, MA 02152
Year Built:
2022
HOA:
None
$388,888
1
Bed
2
Baths
585
Sqft
600 Shirley St #4
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$385,000
2
Beds
1
Bath
677
Sqft
53 Trident Ave #301
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$380,000
2
Beds
1
Bath
782
Sqft
1000 Governor's Drive #15
Winthrop, MA 02152
Year Built:
1972
HOA:
None
$369,000
1
Bed
1
Bath
1,000
Sqft
69 Summit Ave #1
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$350,000
2
Beds
1
Bath
649
Sqft
175 Shirley Street #5
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$340,000
2
Beds
1
Bath
772
Sqft
800 Governors Dr #6
Winthrop, MA 02152
Year Built:
1971
HOA:
None
$299,999
1
Bed
1
Bath
351
Sqft
600 Shirley St #11
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$219,999
1
Bed
1
Bath
350
Sqft
229 Washington Ave #3A
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$219,999
1
Bed
1
Bath
350
Sqft
229 Washington Ave #3A
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$6,500/mo
4
Beds
3/1
Baths
2,780
Sqft
170 Cliff Ave #170
Winthrop, MA 02152
Year Built:
2008
HOA:
None
$6,000/mo
3
Beds
3/1
Baths
2,780
Sqft
170 Cliff Ave #170
Winthrop, MA 02152
Year Built:
2008
HOA:
None
$5,000/mo
3
Beds
2
Baths
2,100
Sqft
876 Shirley St #2
Winthrop, MA 02152
Year Built:
1910
HOA:
None
$4,000/mo
3
Beds
1/1
Bath
1,300
Sqft
393 Main St #house
Winthrop, MA 02152
Year Built:
1930
HOA:
None
$4,000/mo
3
Beds
2/1
Baths
2,100
Sqft
111 Winthrop Shore Drive
Winthrop, MA 02152
Year Built:
--
HOA:
None
$3,500/mo
3
Beds
1
Bath
1,100
Sqft
78 Read Street #1
Winthrop, MA 02152
Year Built:
--
HOA:
None
$3,500/mo
3
Beds
1/1
Bath
110
Sqft
70 Reed Street #1
Winthrop, MA 02152
Year Built:
1920
HOA:
None
$3,500/mo
2
Beds
2
Baths
1,286
Sqft
3 Seal Harbor Rd #533
Winthrop, MA 02152
Year Built:
--
HOA:
None
$3,400/mo
2
Beds
2
Baths
1,657
Sqft
550 Pleassant Street #404
Winthrop, MA 02152
Year Built:
--
HOA:
None
$3,400/mo
3
Beds
1
Bath
1,500
Sqft
274 Bowdoin Street #3
Winthrop, MA 02152
Year Built:
--
HOA:
None
$3,400/mo
3
Beds
2
Baths
1,100
Sqft
585 Shirley St #1
Winthrop, MA 02152
Year Built:
--
HOA:
None
$3,400/mo
2
Beds
2
Baths
1,120
Sqft
1 Pond St #4N
Winthrop, MA 02162
Year Built:
1960
HOA:
None
$3,300/mo
3
Beds
1
Bath
1,400
Sqft
50 Trident Ave #3
Winthrop, MA 02152
Year Built:
1900
HOA:
None
$3,200/mo
3
Beds
1
Bath
1,113
Sqft
180 Shirley St #3
Winthrop, MA 02152
Year Built:
--
HOA:
None
$3,200/mo
3
Beds
1
Bath
1,400
Sqft
50 Trident Ave #C
Winthrop, MA 02152
Year Built:
1900
HOA:
None
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