Winthrop Real Estate

Winthrop is a city located along the Massachusetts coast just to the north of Boston. Known as the gateway to the Northshore, Winthrop is a 1.6 square mile peninsula situated at the north entrance to Boston Harbor near Logan Airport. The community features seven miles of shoreline and stunning views of the Boston skyline are found in many vantage points throughout Winthrop. This densely populated city is home to approximately 18,000 residents.   Read more about Winthrop.

Winthrop Homes & Condos For Sale

17 Walden Street, Winthrop
  • Income/Multi Family
  • 0 Beds
  • 0 Baths
  • 19,100 SqFt

17 Walden Street, Winthrop

$3,000,000
585-586 Shirley Street, Winthrop
  • Income/Multi Family
  • 19 Beds
  • 11 Baths
  • 8,231 SqFt

585-586 Shirley Street, Winthrop

$2,600,000 ↓ $400,000
93 Crest Avenue, Winthrop
  • Income/Multi Family
  • 6 Beds
  • 3 Baths
  • 3,264 SqFt

93 Crest Avenue, Winthrop

$1,498,000
586 Shirley Street, Winthrop
  • Income/Multi Family
  • 8 Beds
  • 6 Baths
  • 3,937 SqFt

586 Shirley Street, Winthrop

$1,300,000 ↓ $200,000
585 Shirley Street, Winthrop
  • Income/Multi Family
  • 11 Beds
  • 5 Baths
  • 4,294 SqFt

585 Shirley Street, Winthrop

$1,300,000 ↓ $200,000
143 Court Road, Winthrop
  • Single Family
  • 5 Beds
  • 2 Baths
  • 2,400 SqFt

143 Court Road, Winthrop

$1,290,000
49 Siren Street, Winthrop
  • Income/Multi Family
  • 8 Beds
  • 4 Baths
  • 3,272 SqFt

49 Siren Street, Winthrop

$1,200,000
3 Seal Harbor Road #ph 33, Winthrop
  • Single Family
  • 3 Beds
  • 3 Baths
  • 1,913 SqFt

3 Seal Harbor Road #ph 33, Winthrop

$899,000
246 Winthrop Shore Drive, Winthrop
  • Income/Multi Family
  • 6 Beds
  • 3.5 Baths
  • 3,107 SqFt

246 Winthrop Shore Drive, Winthrop

$899,000 ↓ $50,900
114 Pleasant Street, Winthrop
  • Single Family
  • 6 Beds
  • 2.5 Baths
  • 2,666 SqFt

114 Pleasant Street, Winthrop

$849,000 ↓ $20,000
89-r Upland Rd., Winthrop
  • Single Family
  • 3 Beds
  • 1 Baths
  • 1,194 SqFt

89-r Upland Rd., Winthrop

$839,900 ↓ $50,000
93 Crest Avenue #2, Winthrop
  • Single Family
  • 4 Beds
  • 2 Baths
  • 2,277 SqFt

93 Crest Avenue #2, Winthrop

$819,000
69-r Undine Avenue, Winthrop
  • Income/Multi Family
  • 7 Beds
  • 3 Baths
  • 2,970 SqFt

69-r Undine Avenue, Winthrop

$800,000
50 Cliff Avenue, Winthrop
  • Income/Multi Family
  • 4 Beds
  • 2 Baths
  • 2,268 SqFt

50 Cliff Avenue, Winthrop

$799,900 ↓ $50,000
620 Shirley Street, Winthrop
  • Income/Multi Family
  • 6 Beds
  • 4 Baths
  • 2,321 SqFt

620 Shirley Street, Winthrop

$799,900
290 Bowdoin Street, Winthrop
  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,413 SqFt

290 Bowdoin Street, Winthrop

$779,000
40 Quincy Avenue, Winthrop
  • Income/Multi Family
  • 6 Beds
  • 2 Baths
  • 3,500 SqFt

40 Quincy Avenue, Winthrop

$777,000 ↓ $12,000
11 Bellevue Avenue, Winthrop
  • Income/Multi Family
  • 5 Beds
  • 2 Baths
  • 3,053 SqFt

11 Bellevue Avenue, Winthrop

$769,000 ↓ $30,500
38 Madison Avenue, Winthrop
  • Income/Multi Family
  • 4 Beds
  • 2 Baths
  • 1,980 SqFt

38 Madison Avenue, Winthrop

$750,000
53 Prospect Avenue, Winthrop
  • Single Family
  • 3 Beds
  • 3 Baths
  • 2,204 SqFt

53 Prospect Avenue, Winthrop

$749,900
New
175 Main Street, Winthrop
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,630 SqFt

175 Main Street, Winthrop

$749,000
45 Tileston Road #1, Winthrop
  • Single Family
  • 3 Beds
  • 2.5 Baths
  • 1,935 SqFt

45 Tileston Road #1, Winthrop

$745,000 ↓ $14,000
45 Tileston Road #3, Winthrop
  • Single Family
  • 3 Beds
  • 2.5 Baths
  • 1,935 SqFt

45 Tileston Road #3, Winthrop

$735,000 ↓ $14,000
79 Woodside Avenue, Winthrop
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,600 SqFt

79 Woodside Avenue, Winthrop

$724,900
25 Locust Street, Winthrop
  • Income/Multi Family
  • 6 Beds
  • 6 Baths
  • 4,400 SqFt

25 Locust Street, Winthrop

$700,000
10 Cottage Avenue, Winthrop
  • Single Family
  • 3 Beds
  • 1.5 Baths
  • 1,628 SqFt

10 Cottage Avenue, Winthrop

$699,000 ↓ $50,000
21 Hutchinson Street, Winthrop
  • Income/Multi Family
  • 5 Beds
  • 2 Baths
  • 2,243 SqFt

21 Hutchinson Street, Winthrop

$699,000 ↓ $36,000
93 Crest Avenue #1, Winthrop
  • Single Family
  • 2 Beds
  • 1 Baths
  • 1,251 SqFt

93 Crest Avenue #1, Winthrop

$679,000
106 Washington Avenue, Winthrop
  • Single Family
  • 4 Beds
  • 1.5 Baths
  • 1,950 SqFt

106 Washington Avenue, Winthrop

$650,000 ↓ $49,000
35 Girdlestone Road, Winthrop
  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,211 SqFt

35 Girdlestone Road, Winthrop

$649,000
35 Siren Street, Winthrop
  • Income/Multi Family
  • 6 Beds
  • 2 Baths
  • 2,280 SqFt

35 Siren Street, Winthrop

$649,000
New
45 Cross Street, Winthrop
  • Single Family
  • 2 Beds
  • 2 Baths
  • 2,586 SqFt

45 Cross Street, Winthrop

$599,900
550 Pleasant #504, Winthrop
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,657 SqFt

550 Pleasant #504, Winthrop

$599,900
3 Seal Harbor #242, Winthrop
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,353 SqFt

3 Seal Harbor #242, Winthrop

$581,000
51-53 Cutler Street #1, Winthrop
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,589 SqFt

51-53 Cutler Street #1, Winthrop

$565,000 ↓ $34,000
56 Otis Street, Winthrop
  • Single Family
  • 2 Beds
  • 1 Baths
  • 1,105 SqFt

56 Otis Street, Winthrop

$550,000
993 Shirley Street, Winthrop
  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,184 SqFt

993 Shirley Street, Winthrop

$550,000 ↓ $49,900
83 Lincoln Street, Winthrop
  • Single Family
  • 3 Beds
  • 2.5 Baths
  • 2,022 SqFt

83 Lincoln Street, Winthrop

$549,900 ↓ $50,000
22-24 Nevada Street #2, Winthrop
  • Single Family
  • 4 Beds
  • 3 Baths
  • 2,083 SqFt

22-24 Nevada Street #2, Winthrop

$540,000 ↓ $25,000
46 Jefferson Street #2, Winthrop
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,139 SqFt

46 Jefferson Street #2, Winthrop

$529,800 ↓ $9,200
15 Ocean Avenue #107, Winthrop
  • Single Family
  • 2 Beds
  • 2 Baths
  • 1,365 SqFt

15 Ocean Avenue #107, Winthrop

$529,000 ↓ $20,000
48 Crystal Cove Avenue #1, Winthrop
  • Single Family
  • 4 Beds
  • 2 Baths
  • 1,870 SqFt

48 Crystal Cove Avenue #1, Winthrop

$519,900 ↑ $4,900
New
29 Triton Avenue, Winthrop
  • Single Family
  • 3 Beds
  • 1 Baths
  • 1,500 SqFt

29 Triton Avenue, Winthrop

$519,000
39 Moore Street, Winthrop
  • Single Family
  • 3 Beds
  • 1.5 Baths
  • 1,464 SqFt

39 Moore Street, Winthrop

$519,000
286 Revere Street #2, Winthrop
  • Single Family
  • 3 Beds
  • 2 Baths
  • 1,378 SqFt

286 Revere Street #2, Winthrop

$499,900
56 Beach Road, Winthrop
  • Single Family
  • 2 Beds
  • 1 Baths
  • 1,484 SqFt

56 Beach Road, Winthrop

$499,900 ↓ $20,000
36 Coral Avenue, Winthrop
  • Single Family
  • 3 Beds
  • 1.5 Baths
  • 1,360 SqFt

36 Coral Avenue, Winthrop

$469,000 ↓ $20,000
38 Trident Avenue #1, Winthrop
  • Single Family
  • 2 Beds
  • 1 Baths
  • 1,160 SqFt

38 Trident Avenue #1, Winthrop

$449,999

More About Winthrop

Winthrop Location

With a location just to the North of Boston, the convenience of commuting from Winthrop is a major draw. Winthrop is connected to Revere via Winthrop Parkway and to East Boston via a bridge that runs along Saratoga Street over the Harbor Inlet. MBTA buses run throughout Winthrop and provide access to the Orient Heights Station on the Blue Line which is four stops away from Downtown Boston.

Winthrop Recreation

Winthrop is a popular community with boaters and is home to six marinas with over 600 slips and 300 moorings. The community has two beaches, Winthrop Beach and Yirrell Beach and about a third of the shoreline is open to the public. Residents enjoy walking and taking in natural beauty at Belle Isle Marsh Reservation and Deer Island Park.

Winthrop History

Winthrop was founded in 1630 and is one of the oldest communities in Massachusetts and the nation. It draws its name from John Winthrop, the second governor of Massachusetts Bay Colony. The home of John Winthrop's son Deane, which was built in 1637 is a historic site and museum.

 

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