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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 4/21/2025)

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  1. Photo of 1024 S Main St #1, Attleboro, MA 02703 (MLS # 73361474)
    $410,000
    Photo of 1024 S Main St #1, Attleboro, MA 02703 (MLS # 73361474)
    Photo of 1024 S Main St #1, Attleboro, MA 02703 (MLS # 73361474)
    29
     
    1024 S Main St #1, Attleboro, MA
    1024 S Main St #1
    Attleboro, MA
    • 2 Beds
    • 2 Baths
    • 1,152 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Century 21 North East
  2. Photo of 51 Black Brook Crossing, West Tisbury, MA 02575 (MLS # 73361473)
    $2,085,000
    Photo of 51 Black Brook Crossing, West Tisbury, MA 02575 (MLS # 73361473)
    Photo of 51 Black Brook Crossing, West Tisbury, MA 02575 (MLS # 73361473)
    36
     
    51 Black Brook Crossing, West Tisbury, MA
    51 Black Brook Crossing
    West Tisbury, MA
    • 4 Beds
    • 3 Baths
    • 2,691 Home (sqft)
    • 3 Baths
    • 43,560 Lot (sqft)
    Listed with Karen M. Overtoom R.E.
  3. Photo of 750 Davol St #813, Fall River, MA 02720 (MLS # 73361472)
    $297,000
    Photo of 750 Davol St #813, Fall River, MA 02720 (MLS # 73361472)
    Photo of 750 Davol St #813, Fall River, MA 02720 (MLS # 73361472)
    37
     
    750 Davol St #813, Fall River, MA
    750 Davol St #813
    Fall River, MA
    • 2 Beds
    • 2 Baths
    • 915 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Beach Homes Realty, LLC
  4. Photo of 169 Gosnold Street, Barnstable, MA 02601 (MLS # 73361469)
    $899,000
    Photo of 169 Gosnold Street, Barnstable, MA 02601 (MLS # 73361469)
    Photo of 169 Gosnold Street, Barnstable, MA 02601 (MLS # 73361469)
    36
     
    169 Gosnold Street, Barnstable, MA
    169 Gosnold Street
    Barnstable, MA
    • 5 Beds
    • 3 Baths
    • 1,821 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
    Listed with Keller Williams Realty
  5. Photo of 183-185A Massachusetts Ave #602, Boston, MA 02115 (MLS # 73361471)
    $1,159,000
    Photo of 183-185A Massachusetts Ave #602, Boston, MA 02115 (MLS # 73361471)
    Photo of 183-185A Massachusetts Ave #602, Boston, MA 02115 (MLS # 73361471)
    27
     
    183-185A Massachusetts Ave #602, Boston, MA
    183-185A Massachusetts Ave #602
    Boston, MA
    • 1 Bed
    • 1 Bath
    • 891 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
    Listed with eXp Realty
  6. Photo of 2 Bertha St, Hudson, MA 01749 (MLS # 73361464)
    $499,900
    Photo of 2 Bertha St, Hudson, MA 01749 (MLS # 73361464)
    Photo of 2 Bertha St, Hudson, MA 01749 (MLS # 73361464)
    17
     
    2 Bertha St, Hudson, MA
    2 Bertha St
    Hudson, MA
    • 3 Beds
    • 1 Bath
    • 1,513 Home (sqft)
    • 1 Bath
    • 11,326 Lot (sqft)
    Listed with Susan Meola, Properties
  7. Photo of 183-185A Massachusetts Ave #803, Boston, MA 02115 (MLS # 73361468)
    $1,595,000
    Photo of 183-185A Massachusetts Ave #803, Boston, MA 02115 (MLS # 73361468)
    Photo of 183-185A Massachusetts Ave #803, Boston, MA 02115 (MLS # 73361468)
    29
     
    183-185A Massachusetts Ave #803, Boston, MA
    183-185A Massachusetts Ave #803
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,220 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
    Listed with eXp Realty
  8. Photo of 35 Windsor Lane #A, Hudson, NH 03051 (MLS # 73361467)
    $599,900
    Photo of 35 Windsor Lane #A, Hudson, NH 03051 (MLS # 73361467)
    Photo of 35 Windsor Lane #A, Hudson, NH 03051 (MLS # 73361467)
    35 Windsor Lane #A, Hudson, NH
    35 Windsor Lane #A
    Hudson, NH
    • 3 Beds
    • 2 Baths
    • 2,004 Home (sqft)
    • 2 Baths
    • 1.07 Lot (ac)
    Listed with Berkshire Hathaway HomeServices Verani Realty
  9. Photo of 150 Seaport Blvd #12B, Boston, MA 02210 (MLS # 73361461)
    $2,620,000
    Photo of 150 Seaport Blvd #12B, Boston, MA 02210 (MLS # 73361461)
    Photo of 150 Seaport Blvd #12B, Boston, MA 02210 (MLS # 73361461)
    23
     
    150 Seaport Blvd #12B, Boston, MA
    150 Seaport Blvd #12B
    Boston, MA
    • 2 Beds
    • 3 Baths
    • 1,498 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with TCC / St. Regis Residences
  10. Photo of 24 Ballard Street, Saugus, MA 01906 (MLS # 73361456)
    $899,000
    Photo of 24 Ballard Street, Saugus, MA 01906 (MLS # 73361456)
    Photo of 24 Ballard Street, Saugus, MA 01906 (MLS # 73361456)
    42
     
    24 Ballard Street, Saugus, MA
    24 Ballard Street
    Saugus, MA
    • 4 Beds
    • 3 Baths
    • 2,180 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
    Listed with StartPoint Realty & Associates
  11. Photo of 55 Mendon Rd, Sutton, MA 01590 (MLS # 73361458)
    $649,900
    Photo of 55 Mendon Rd, Sutton, MA 01590 (MLS # 73361458)
    Photo of 55 Mendon Rd, Sutton, MA 01590 (MLS # 73361458)
    24
     
    55 Mendon Rd, Sutton, MA
    55 Mendon Rd
    Sutton, MA
    • 4 Beds
    • 3 Baths
    • 2,240 Home (sqft)
    • 3 Baths
    • 1.85 Lot (ac)
    Listed with Coldwell Banker Realty - Northborough
  12. Photo of 2 Centerville Ave, Barnstable, MA 02632 (MLS # 73361453)
    $975,000
    Photo of 2 Centerville Ave, Barnstable, MA 02632 (MLS # 73361453)
    Photo of 2 Centerville Ave, Barnstable, MA 02632 (MLS # 73361453)
    42
     
    2 Centerville Ave, Barnstable, MA
    2 Centerville Ave
    Barnstable, MA
    • 4 Beds
    • 4 Baths
    • 3,456 Home (sqft)
    • 4 Baths
    • 15,246 Lot (sqft)
    Listed with Kinlin Grover Compass
  13. Photo of 228 Greenbrook Dr #228, Stoughton, MA 02072 (MLS # 73361449)
    $439,900
    Photo of 228 Greenbrook Dr #228, Stoughton, MA 02072 (MLS # 73361449)
    Photo of 228 Greenbrook Dr #228, Stoughton, MA 02072 (MLS # 73361449)
    16
     
    228 Greenbrook Dr #228, Stoughton, MA
    228 Greenbrook Dr #228
    Stoughton, MA
    • 2 Beds
    • 2 Baths
    • 1,230 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Cameron Real Estate Group
  14. Photo of 3 Longfellow Road, Worcester, MA 01602 (MLS # 73361445)
    $629,900
    Photo of 3 Longfellow Road, Worcester, MA 01602 (MLS # 73361445)
    Photo of 3 Longfellow Road, Worcester, MA 01602 (MLS # 73361445)
    33
     
    3 Longfellow Road, Worcester, MA
    3 Longfellow Road
    Worcester, MA
    • 6 Beds
    • 2 Baths
    • 3,224 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
    Listed with RE/MAX Vision
  15. Photo of 1 Franklin Street #PH4B, Boston, MA 02110 (MLS # 73361444)
    $9,450,000
    Photo of 1 Franklin Street #PH4B, Boston, MA 02110 (MLS # 73361444)
    Photo of 1 Franklin Street #PH4B, Boston, MA 02110 (MLS # 73361444)
    14
     
    1 Franklin Street #PH4B, Boston, MA
    1 Franklin Street #PH4B
    Boston, MA
    • 3 Beds
    • 5 Baths
    • 4,110 Home (sqft)
    • 5 Baths
    • 0 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  16. Photo of 81 Earle Street, Norwood, MA 02062 (MLS # 73361441)
    $658,000
    Photo of 81 Earle Street, Norwood, MA 02062 (MLS # 73361441)
    Photo of 81 Earle Street, Norwood, MA 02062 (MLS # 73361441)
    12
     
    81 Earle Street, Norwood, MA
    81 Earle Street
    Norwood, MA
    • 4 Beds
    • 3 Baths
    • 2,408 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
    Listed with Keller Williams Realty Boston South West
  17. Photo of 107 Market Street #A, Amesbury, MA 01913 (MLS # 73361443)
    $813,000
    Photo of 107 Market Street #A, Amesbury, MA 01913 (MLS # 73361443)
    Photo of 107 Market Street #A, Amesbury, MA 01913 (MLS # 73361443)
    107 Market Street #A, Amesbury, MA
    107 Market Street #A
    Amesbury, MA
    • 3 Beds
    • 4 Baths
    • 2,041 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with William Raveis Real Estate
  18. Photo of 5 Eagle Hill Rd, Ipswich, MA 01938 (MLS # 73361440)
    $899,000
    Photo of 5 Eagle Hill Rd, Ipswich, MA 01938 (MLS # 73361440)
    Photo of 5 Eagle Hill Rd, Ipswich, MA 01938 (MLS # 73361440)
    32
     
    5 Eagle Hill Rd, Ipswich, MA
    5 Eagle Hill Rd
    Ipswich, MA
    • 3 Beds
    • 1 Bath
    • 1,312 Home (sqft)
    • 1 Bath
    • 14,375 Lot (sqft)
    Listed with Compass
  19. Photo of 18 Buchanan Rd, Yarmouth, MA 02673 (MLS # 73361439)
    $760,000
    Photo of 18 Buchanan Rd, Yarmouth, MA 02673 (MLS # 73361439)
    Photo of 18 Buchanan Rd, Yarmouth, MA 02673 (MLS # 73361439)
    41
     
    18 Buchanan Rd, Yarmouth, MA
    18 Buchanan Rd
    Yarmouth, MA
    • 2 Beds
    • 2 Baths
    • 1,710 Home (sqft)
    • 2 Baths
    • 16,553 Lot (sqft)
    Listed with LAER Realty Partners
  20. Photo of 58 Beacon Hill Court, Lynn, MA 01902 (MLS # 73361433)
    $525,000
    Photo of 58 Beacon Hill Court, Lynn, MA 01902 (MLS # 73361433)
    Photo of 58 Beacon Hill Court, Lynn, MA 01902 (MLS # 73361433)
    14
     
    58 Beacon Hill Court, Lynn, MA
    58 Beacon Hill Court
    Lynn, MA
    • 3 Beds
    • 2 Baths
    • 1,300 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
    Listed with eXp Realty
  21. Photo of 177 Rogers, West Springfield, MA 01089 (MLS # 73361429)
    $760,000
    Photo of 177 Rogers, West Springfield, MA 01089 (MLS # 73361429)
    Photo of 177 Rogers, West Springfield, MA 01089 (MLS # 73361429)
    27
     
    177 Rogers, West Springfield, MA
    177 Rogers
    West Springfield, MA
    • 3 Beds
    • 3 Baths
    • 2,563 Home (sqft)
    • 3 Baths
    • 1.42 Lot (ac)
    Listed with Gallagher Real Estate
  22. Photo of 6 Peckham St, Attleboro, MA 02703 (MLS # 73361428)
    $770,000
    Photo of 6 Peckham St, Attleboro, MA 02703 (MLS # 73361428)
    Photo of 6 Peckham St, Attleboro, MA 02703 (MLS # 73361428)
    35
     
    6 Peckham St, Attleboro, MA
    6 Peckham St
    Attleboro, MA
    • 4 Beds
    • 3 Baths
    • 2,123 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with The Nest Real Estate Agency, LLC
  23. Photo of 26 1/2 Cherry Street, Spencer, MA 01562 (MLS # 73361424)
    $619,999
    Photo of 26 1/2 Cherry Street, Spencer, MA 01562 (MLS # 73361424)
    Photo of 26 1/2 Cherry Street, Spencer, MA 01562 (MLS # 73361424)
    18
     
    26 1/2 Cherry Street, Spencer, MA
    26 1/2 Cherry Street
    Spencer, MA
    • 3 Beds
    • 3 Baths
    • 2,128 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
    Listed with Buy Rite Home
  24. Photo of 44 Gatewood Rd, Springfield, MA 01119 (MLS # 73361426)
    $269,900
    Photo of 44 Gatewood Rd, Springfield, MA 01119 (MLS # 73361426)
    Photo of 44 Gatewood Rd, Springfield, MA 01119 (MLS # 73361426)
    25
     
    44 Gatewood Rd, Springfield, MA
    44 Gatewood Rd
    Springfield, MA
    • 3 Beds
    • 1 Bath
    • 1,056 Home (sqft)
    • 1 Bath
    • 7,406 Lot (sqft)
    Listed with Gallagher Real Estate
  25. Photo of 22 Ferdinand Street, Worcester, MA 01603 (MLS # 73361419)
    $809,000
    Photo of 22 Ferdinand Street, Worcester, MA 01603 (MLS # 73361419)
    Photo of 22 Ferdinand Street, Worcester, MA 01603 (MLS # 73361419)
    36
     
    22 Ferdinand Street, Worcester, MA
    22 Ferdinand Street
    Worcester, MA
    • 7 Beds
    • 3 Baths
    • 3,435 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
    Listed with Century 21 XSELL REALTY
  26. Photo of 190 Essex Street, Middleton, MA 01949 (MLS # 73361409)
    $749,888
    Photo of 190 Essex Street, Middleton, MA 01949 (MLS # 73361409)
    Photo of 190 Essex Street, Middleton, MA 01949 (MLS # 73361409)
    21
     
    190 Essex Street, Middleton, MA
    190 Essex Street
    Middleton, MA
    • 3 Beds
    • 2 Baths
    • 1,773 Home (sqft)
    • 2 Baths
    • 1.35 Lot (ac)
    Listed with Compass
  27. Photo of 68 Dory Lane #68, Eastham, MA 02642 (MLS # 73361412)
    $649,000
    Photo of 68 Dory Lane #68, Eastham, MA 02642 (MLS # 73361412)
    Photo of 68 Dory Lane #68, Eastham, MA 02642 (MLS # 73361412)
    42
     
    68 Dory Lane #68, Eastham, MA
    68 Dory Lane #68
    Eastham, MA
    • 2 Beds
    • 2 Baths
    • 1,558 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  28. Photo of 94 Warwick Ave, Athol, MA 01331 (MLS # 73361405)
    $400,000
    Photo of 94 Warwick Ave, Athol, MA 01331 (MLS # 73361405)
    Photo of 94 Warwick Ave, Athol, MA 01331 (MLS # 73361405)
    34
     
    94 Warwick Ave, Athol, MA
    94 Warwick Ave
    Athol, MA
    • 3 Beds
    • 2 Baths
    • 1,680 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
    Listed with A & E Realty Company, Inc.
  29. Photo of 766 Willard St #A7, Quincy, MA 02169 (MLS # 73361408)
    $420,000
    Photo of 766 Willard St #A7, Quincy, MA 02169 (MLS # 73361408)
    Photo of 766 Willard St #A7, Quincy, MA 02169 (MLS # 73361408)
    766 Willard St #A7, Quincy, MA
    766 Willard St #A7
    Quincy, MA
    • 2 Beds
    • 1 Bath
    • 807 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Canton
  30. Photo of 570 Merrimac St, Newburyport, MA 01950 (MLS # 73361401)
    $4,195,000
    Photo of 570 Merrimac St, Newburyport, MA 01950 (MLS # 73361401)
    Photo of 570 Merrimac St, Newburyport, MA 01950 (MLS # 73361401)
    570 Merrimac St, Newburyport, MA
    570 Merrimac St
    Newburyport, MA
    • 5 Beds
    • 6 Baths
    • 5,451 Home (sqft)
    • 6 Baths
    • 20,038 Lot (sqft)
    Listed with Realty One Group Nest
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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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