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Winthrop is a medium-sized coastal city (i.e. on the ocean, a bay, or inlet) located in the state of Massachusetts. With a population of 18,544 people and five constituent neighborhoods, Winthrop is the 107th largest community in Massachusetts. Much of the housing stock in Winthrop was built prior to World War II, making it one of the older and more historic cities in the country.

Housing costs in Winthrop are among some of the highest in the nation, although real estate prices here don't compare to real estate prices in the most expensive communities in Massachusetts.

Winthrop is a decidedly white-collar city, with fully 87.18% of the workforce employed in white-collar jobs, well above the national average. Overall, Winthrop is a city of sales and office workers, professionals, and managers. There are especially a lot of people living in Winthrop who work in office and administrative support (16.24%), sales jobs (12.57%), and management occupations (11.63%).

Also of interest is that Winthrop has more people living here who work in computers and math than 95% of the places in the US.

Winthrop is also nautical, which means that parts of it are somewhat historic and touch the ocean or tidal bodies of water, such as inlets and bays. Quite often, nautical areas such as these attract visitors and locals who come to enjoy the scenery and various waterfront activities.

In Winthrop, however, the average commute to work is quite long. On average, people spend 34.28 minutes each day getting to work, which is significantly higher than the national average. One bright side is that local public transit is widely used, so it may be an option to avoid the headache of driving in the heavy traffic by leaving the car at home and taking transit. In addition, the city is also quite pedestrian-friendly, because many neighborhoods are very dense and have amenities close enough together that people find it feasible to get around on foot.

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(all data current as of 4/22/2025)

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  1. Photo of 485 Blue Hills Parkway #5, Milton, MA 02186 (MLS # 73361656)
    $549,999
    Photo of 485 Blue Hills Parkway #5, Milton, MA 02186 (MLS # 73361656)
    Photo of 485 Blue Hills Parkway #5, Milton, MA 02186 (MLS # 73361656)
    15
     
    485 Blue Hills Parkway #5, Milton, MA
    485 Blue Hills Parkway #5
    Milton, MA
    • 1 Bed
    • 1 Bath
    • 916 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Duxbury
  2. Photo of 1395 Washington Street #505, Boston, MA 02118 (MLS # 73361653)
    $1,285,000
    Photo of 1395 Washington Street #505, Boston, MA 02118 (MLS # 73361653)
    Photo of 1395 Washington Street #505, Boston, MA 02118 (MLS # 73361653)
    21
     
    1395 Washington Street #505, Boston, MA
    1395 Washington Street #505
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 871 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  3. Photo of 149 Prospect St, Leominster, MA 01453 (MLS # 73359089)
    $549,900
    Photo of 149 Prospect St, Leominster, MA 01453 (MLS # 73359089)
    Photo of 149 Prospect St, Leominster, MA 01453 (MLS # 73359089)
    36
     
    149 Prospect St, Leominster, MA
    149 Prospect St
    Leominster, MA
    • 4 Beds
    • 2 Baths
    • 2,168 Home (sqft)
    • 2 Baths
    • 22,652 Lot (sqft)
    Listed with LAER Realty Partners
  4. Photo of 139 Selden St, Boston, MA 02124 (MLS # 73361649)
    $975,000
    Photo of 139 Selden St, Boston, MA 02124 (MLS # 73361649)
    Photo of 139 Selden St, Boston, MA 02124 (MLS # 73361649)
    139 Selden St, Boston, MA
    139 Selden St
    Boston, MA
    • 6 Beds
    • 3 Baths
    • 3,082 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
    Listed with The Firm
  5. Photo of 8 Treetop Ln #5, Kingston, MA 02364 (MLS # 73361650)
    $390,000
    Photo of 8 Treetop Ln #5, Kingston, MA 02364 (MLS # 73361650)
    Photo of 8 Treetop Ln #5, Kingston, MA 02364 (MLS # 73361650)
    34
     
    8 Treetop Ln #5, Kingston, MA
    8 Treetop Ln #5
    Kingston, MA
    • 2 Beds
    • 2 Baths
    • 1,271 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with KKeegan Realty
  6. Photo of Lot 332 Chief Justice Cushing Highway, Scituate, MA 02066 (MLS # 73361646)
    $1,350,000
    Photo of Lot 332 Chief Justice Cushing Highway, Scituate, MA 02066 (MLS # 73361646)
    Photo of Lot 332 Chief Justice Cushing Highway, Scituate, MA 02066 (MLS # 73361646)
    18
     
    Lot 332 Chief Justice Cushing Highway, Scituate, MA
    Lot 332 Chief Justice Cushing Highway
    Scituate, MA
    • 4 Beds
    • 3 Baths
    • 2,600 Home (sqft)
    • 3 Baths
    • 1.22 Lot (ac)
    Listed with Real Broker MA, LLC
  7. Photo of 144 Thurber Ave, Attleboro, MA 02703 (MLS # 73361643)
    $450,000
    Photo of 144 Thurber Ave, Attleboro, MA 02703 (MLS # 73361643)
    Photo of 144 Thurber Ave, Attleboro, MA 02703 (MLS # 73361643)
    35
     
    144 Thurber Ave, Attleboro, MA
    144 Thurber Ave
    Attleboro, MA
    • 3 Beds
    • 1 Bath
    • 1,040 Home (sqft)
    • 1 Bath
    • 12,197 Lot (sqft)
    Listed with JH Realty Group LLC
  8. Photo of 57a Mount, Worcester, MA 01606 (MLS # 73361642)
    $600,000
    Photo of 57a Mount, Worcester, MA 01606 (MLS # 73361642)
    Photo of 57a Mount, Worcester, MA 01606 (MLS # 73361642)
    32
     
    57a Mount, Worcester, MA
    57a Mount
    Worcester, MA
    • 3 Beds
    • 3 Baths
    • 2,346 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
    Listed with Harrington Real Estate Advisors
  9. Photo of 19 Beach Plum Path, Falmouth, MA 02536 (MLS # 73361344)
    $770,000
    Photo of 19 Beach Plum Path, Falmouth, MA 02536 (MLS # 73361344)
    Photo of 19 Beach Plum Path, Falmouth, MA 02536 (MLS # 73361344)
    19 Beach Plum Path, Falmouth, MA
    19 Beach Plum Path
    Falmouth, MA
    • 3 Beds
    • 3 Baths
    • 1,547 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Robert Paul Properties
  10. Photo of 24 Grey Hawk Dr #646, Mashpee, MA 02649 (MLS # 73361833)
    $699,000
    Photo of 24 Grey Hawk Dr #646, Mashpee, MA 02649 (MLS # 73361833)
    Photo of 24 Grey Hawk Dr #646, Mashpee, MA 02649 (MLS # 73361833)
    24
     
    24 Grey Hawk Dr #646, Mashpee, MA
    24 Grey Hawk Dr #646
    Mashpee, MA
    • 2 Beds
    • 2 Baths
    • 1,952 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Kinlin Grover Compass
  11. Photo of 153 Union Rd, Wales, MA 01081 (MLS # 73361699)
    $375,000
    Photo of 153 Union Rd, Wales, MA 01081 (MLS # 73361699)
    Photo of 153 Union Rd, Wales, MA 01081 (MLS # 73361699)
    31
     
    153 Union Rd, Wales, MA
    153 Union Rd
    Wales, MA
    • 3 Beds
    • 1 Bath
    • 1,170 Home (sqft)
    • 1 Bath
    • 1.10 Lot (ac)
    Listed with Berkshire Hathaway HomeServices Realty Professionals
  12. Photo of 1595 Washington St, East Bridgewater, MA 02333 (MLS # 73361636)
    $579,900
    Photo of 1595 Washington St, East Bridgewater, MA 02333 (MLS # 73361636)
    Photo of 1595 Washington St, East Bridgewater, MA 02333 (MLS # 73361636)
    17
     
    1595 Washington St, East Bridgewater, MA
    1595 Washington St
    East Bridgewater, MA
    • 3 Beds
    • 2 Baths
    • 1,700 Home (sqft)
    • 2 Baths
    • 22,216 Lot (sqft)
    Listed with Trust Realty Solutions, LLC
  13. Photo of 9 Landmark Ln, Rockport, MA 01966 (MLS # 73361633)
    $1,575,000
    Photo of 9 Landmark Ln, Rockport, MA 01966 (MLS # 73361633)
    Photo of 9 Landmark Ln, Rockport, MA 01966 (MLS # 73361633)
    41
     
    9 Landmark Ln, Rockport, MA
    9 Landmark Ln
    Rockport, MA
    • 4 Beds
    • 3 Baths
    • 2,700 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
    Listed with Holly C & Co. Fine Homes
  14. Photo of 20 Northwood Dr #203, Sudbury, MA 01776 (MLS # 73361632)
    $669,000
    Photo of 20 Northwood Dr #203, Sudbury, MA 01776 (MLS # 73361632)
    Photo of 20 Northwood Dr #203, Sudbury, MA 01776 (MLS # 73361632)
    20 Northwood Dr #203, Sudbury, MA
    20 Northwood Dr #203
    Sudbury, MA
    • 1 Bed
    • 2 Baths
    • 1,616 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  15. Photo of 1563 Andover St #16, Tewksbury, MA 01876 (MLS # 73361631)
    $565,000
    Photo of 1563 Andover St #16, Tewksbury, MA 01876 (MLS # 73361631)
    Photo of 1563 Andover St #16, Tewksbury, MA 01876 (MLS # 73361631)
    29
     
    1563 Andover St #16, Tewksbury, MA
    1563 Andover St #16
    Tewksbury, MA
    • 3 Beds
    • 3 Baths
    • 1,320 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Deborah Gallagher Realty
  16. Photo of 151-153 Gershom Ave, Lowell, MA 01854 (MLS # 73361630)
    $709,900
    Photo of 151-153 Gershom Ave, Lowell, MA 01854 (MLS # 73361630)
    Photo of 151-153 Gershom Ave, Lowell, MA 01854 (MLS # 73361630)
    37
     
    151-153 Gershom Ave, Lowell, MA
    151-153 Gershom Ave
    Lowell, MA
    • 6 Beds
    • 2 Baths
    • 3,325 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
    Listed with WTymula Real Estate Powered by LAER
  17. Photo of 73 Main Street, Wales, MA 01081 (MLS # 73361628)
    $419,000
    Photo of 73 Main Street, Wales, MA 01081 (MLS # 73361628)
    Photo of 73 Main Street, Wales, MA 01081 (MLS # 73361628)
    41
     
    73 Main Street, Wales, MA
    73 Main Street
    Wales, MA
    • 4 Beds
    • 2 Baths
    • 1,508 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with 1 Worcester Homes
  18. Photo of 1 Franklin St #PH1F, Boston, MA 02110 (MLS # 73361627)
    $3,750,000
    Photo of 1 Franklin St #PH1F, Boston, MA 02110 (MLS # 73361627)
    Photo of 1 Franklin St #PH1F, Boston, MA 02110 (MLS # 73361627)
    42
     
    1 Franklin St #PH1F, Boston, MA
    1 Franklin St #PH1F
    Boston, MA
    • 2 Beds
    • 3 Baths
    • 1,781 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with MP Boston Marketing LLC
  19. Photo of 48 Santa Barbara St, Springfield, MA 01104 (MLS # 73361625)
    $299,900
    Photo of 48 Santa Barbara St, Springfield, MA 01104 (MLS # 73361625)
    Photo of 48 Santa Barbara St, Springfield, MA 01104 (MLS # 73361625)
    33
     
    48 Santa Barbara St, Springfield, MA
    48 Santa Barbara St
    Springfield, MA
    • 4 Beds
    • 2 Baths
    • 1,755 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
    Listed with Signature Realty
  20. Photo of 41 Collins St, Lynn, MA 01902 (MLS # 73361623)
    $779,000
    Photo of 41 Collins St, Lynn, MA 01902 (MLS # 73361623)
    Photo of 41 Collins St, Lynn, MA 01902 (MLS # 73361623)
    38
     
    41 Collins St, Lynn, MA
    41 Collins St
    Lynn, MA
    • 6 Beds
    • 2 Baths
    • 2,799 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
    Listed with Metropolitan Boston Real Estate, LLC
  21. Photo of 38 Village Green Drive #77, North Andover, MA 01845 (MLS # 73361619)
    $419,000
    Photo of 38 Village Green Drive #77, North Andover, MA 01845 (MLS # 73361619)
    Photo of 38 Village Green Drive #77, North Andover, MA 01845 (MLS # 73361619)
    24
     
    38 Village Green Drive #77, North Andover, MA
    38 Village Green Drive #77
    North Andover, MA
    • 2 Beds
    • 1 Bath
    • 1,322 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Stephanie Jo Homes
  22. Photo of 474 Salisbury St, Worcester, MA 01609 (MLS # 73361615)
    $1,000,000
    Photo of 474 Salisbury St, Worcester, MA 01609 (MLS # 73361615)
    Photo of 474 Salisbury St, Worcester, MA 01609 (MLS # 73361615)
    40
     
    474 Salisbury St, Worcester, MA
    474 Salisbury St
    Worcester, MA
    • 4 Beds
    • 4 Baths
    • 4,797 Home (sqft)
    • 4 Baths
    • 1.03 Lot (ac)
    Listed with Coldwell Banker Realty - Worcester
  23. Photo of 68 Mid Iron Way, Mashpee, MA 02649 (MLS # 73361614)
    $529,000
    Photo of 68 Mid Iron Way, Mashpee, MA 02649 (MLS # 73361614)
    Photo of 68 Mid Iron Way, Mashpee, MA 02649 (MLS # 73361614)
    35
     
    68 Mid Iron Way, Mashpee, MA
    68 Mid Iron Way
    Mashpee, MA
    • 2 Beds
    • 2 Baths
    • 1,056 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with New Seabury Sotheby's International Realty
  24. Photo of 131 Ridgeway Dr, Agawam, MA 01030 (MLS # 73361607)
    $985,900
    Photo of 131 Ridgeway Dr, Agawam, MA 01030 (MLS # 73361607)
    Photo of 131 Ridgeway Dr, Agawam, MA 01030 (MLS # 73361607)
    33
     
    131 Ridgeway Dr, Agawam, MA
    131 Ridgeway Dr
    Agawam, MA
    • 7 Beds
    • 5 Baths
    • 6,025 Home (sqft)
    • 5 Baths
    • 43,560 Lot (sqft)
    Listed with Gallagher Real Estate
  25. Photo of 64-74 Belmont St, West Bridgewater, MA 02379 (MLS # 73361601)
    $550,000
    Photo of 64-74 Belmont St, West Bridgewater, MA 02379 (MLS # 73361601)
    Photo of 64-74 Belmont St, West Bridgewater, MA 02379 (MLS # 73361601)
    11
     
    64-74 Belmont St, West Bridgewater, MA
    64-74 Belmont St
    West Bridgewater, MA
    • 3 Beds
    • 1 Bath
    • 864 Home (sqft)
    • 1 Bath
    • 2.00 Lot (ac)
    Listed with Needham Realty
  26. Photo of 9 Maclarnon Rd, Salem, NH 03079 (MLS # 73361596)
    $649,900
    Photo of 9 Maclarnon Rd, Salem, NH 03079 (MLS # 73361596)
    Photo of 9 Maclarnon Rd, Salem, NH 03079 (MLS # 73361596)
    42
     
    9 Maclarnon Rd, Salem, NH
    9 Maclarnon Rd
    Salem, NH
    • 3 Beds
    • 1 Bath
    • 1,709 Home (sqft)
    • 1 Bath
    • 12,197 Lot (sqft)
    Listed with Realty One Group Nest
  27. Photo of 73 Wareham St, Middleboro, MA 02346 (MLS # 73361581)
    $739,999
    Photo of 73 Wareham St, Middleboro, MA 02346 (MLS # 73361581)
    Photo of 73 Wareham St, Middleboro, MA 02346 (MLS # 73361581)
    31
     
    73 Wareham St, Middleboro, MA
    73 Wareham St
    Middleboro, MA
    • 4 Beds
    • 3 Baths
    • 2,693 Home (sqft)
    • 3 Baths
    • 14,375 Lot (sqft)
    Listed with GMH Realty
  28. Photo of 68 Normandy Road, Longmeadow, MA 01106 (MLS # 73361580)
    $949,900
    Photo of 68 Normandy Road, Longmeadow, MA 01106 (MLS # 73361580)
    Photo of 68 Normandy Road, Longmeadow, MA 01106 (MLS # 73361580)
    42
     
    68 Normandy Road, Longmeadow, MA
    68 Normandy Road
    Longmeadow, MA
    • 5 Beds
    • 4 Baths
    • 4,217 Home (sqft)
    • 4 Baths
    • 19,167 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  29. Photo of 169-171 North Ave, Rockland, MA 02370 (MLS # 73361576)
    $849,900
    Photo of 169-171 North Ave, Rockland, MA 02370 (MLS # 73361576)
    Photo of 169-171 North Ave, Rockland, MA 02370 (MLS # 73361576)
    169-171 North Ave, Rockland, MA
    169-171 North Ave
    Rockland, MA
    • 9 Beds
    • 3 Baths
    • 3,611 Home (sqft)
    • 3 Baths
    • 15,682 Lot (sqft)
    Listed with John M. Murtagh Real Estate
  30. Photo of 82 Bond Street, Norwood, MA 02062 (MLS # 73361573)
    $750,000
    Photo of 82 Bond Street, Norwood, MA 02062 (MLS # 73361573)
    Photo of 82 Bond Street, Norwood, MA 02062 (MLS # 73361573)
    38
     
    82 Bond Street, Norwood, MA
    82 Bond Street
    Norwood, MA
    • 2 Beds
    • 2 Baths
    • 1,476 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
    Listed with Keller Williams Realty
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About Alexa

Alexa Dealy is a seven-year residential real estate veteran, having successfully represented hundreds of clients through a wide array of real estate transactions. Born and raised in the Boston area, Alexa has an intrinsic and unteachable understanding of the local real estate market. She comes from a family of real estate investors; it’s no surprise that Alexa began her career in the real estate industry at age 20 – after buying and selling her first investment property for a profit.

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