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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 4/29/2024)

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  1. Photo of 110 Dean St #100, Taunton, MA 02780 (MLS # 73229602)
    $324,900
    Photo of 110 Dean St #100, Taunton, MA 02780 (MLS # 73229602)
    Photo of 110 Dean St #100, Taunton, MA 02780 (MLS # 73229602)
    34
     
    110 Dean St #100, Taunton, MA
    110 Dean St #100
    Taunton, MA
    • 2 Beds
    • 2 Baths
    • 1,350 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Milestone Realty, Inc.
  2. Photo of 19 Longbow Rd, Danvers, MA 01923 (MLS # 73229616)
    $749,999
    Photo of 19 Longbow Rd, Danvers, MA 01923 (MLS # 73229616)
    Photo of 19 Longbow Rd, Danvers, MA 01923 (MLS # 73229616)
    39
     
    19 Longbow Rd, Danvers, MA
    19 Longbow Rd
    Danvers, MA
    • 4 Beds
    • 2 Baths
    • 2,233 Home (sqft)
    • 2 Baths
    • 20,038 Lot (sqft)
    Listed with J. Barrett & Company
  3. Photo of 61 Warren Ave, Milton, MA 02186 (MLS # 73227935)
    $1,250,000
    Photo of 61 Warren Ave, Milton, MA 02186 (MLS # 73227935)
    Photo of 61 Warren Ave, Milton, MA 02186 (MLS # 73227935)
    29
     
    61 Warren Ave, Milton, MA
    61 Warren Ave
    Milton, MA
    • 5 Beds
    • 2 Baths
    • 2,564 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  4. Photo of 24 Chesley Rd, Barnstable, MA 02648 (MLS # 73225861)
    $1,049,900
    Photo of 24 Chesley Rd, Barnstable, MA 02648 (MLS # 73225861)
    Photo of 24 Chesley Rd, Barnstable, MA 02648 (MLS # 73225861)
    41
     
    24 Chesley Rd, Barnstable, MA
    24 Chesley Rd
    Barnstable, MA
    • 3 Beds
    • 4 Baths
    • 2,452 Home (sqft)
    • 4 Baths
    • 1.13 Lot (ac)
    Listed with Sotheby's International Realty
  5. Photo of 99 Talbot Rd, Springfield, MA 01119 (MLS # 73229642)
    $279,900
    Photo of 99 Talbot Rd, Springfield, MA 01119 (MLS # 73229642)
    Photo of 99 Talbot Rd, Springfield, MA 01119 (MLS # 73229642)
    21
     
    99 Talbot Rd, Springfield, MA
    99 Talbot Rd
    Springfield, MA
    • 2 Beds
    • 1 Bath
    • 1,092 Home (sqft)
    • 1 Bath
    • 10,455 Lot (sqft)
    Listed with Coldwell Banker Realty - Western MA
  6. Photo of 380 Wilson Rd, Fall River, MA 02720 (MLS # 73228520)
    $765,000
    Photo of 380 Wilson Rd, Fall River, MA 02720 (MLS # 73228520)
    Photo of 380 Wilson Rd, Fall River, MA 02720 (MLS # 73228520)
    31
     
    380 Wilson Rd, Fall River, MA
    380 Wilson Rd
    Fall River, MA
    • 9 Beds
    • 3 Baths
    • 3,863 Home (sqft)
    • 3 Baths
    • 20,474 Lot (sqft)
    Listed with Circle 100 Real Estate Brokerage LLC
  7. Photo of 106 Webster St #101, Boston, MA 02128 (MLS # 73222121)
    $399,000
    Photo of 106 Webster St #101, Boston, MA 02128 (MLS # 73222121)
    Photo of 106 Webster St #101, Boston, MA 02128 (MLS # 73222121)
    106 Webster St #101, Boston, MA
    106 Webster St #101
    Boston, MA
    • 0 Beds
    • 1 Bath
    • 358 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Efron Property Group, LLC
  8. Photo of 103 Ames Rd, Hampden, MA 01036 (MLS # 73227892)
    $589,900
    Photo of 103 Ames Rd, Hampden, MA 01036 (MLS # 73227892)
    Photo of 103 Ames Rd, Hampden, MA 01036 (MLS # 73227892)
    42
     
    103 Ames Rd, Hampden, MA
    103 Ames Rd
    Hampden, MA
    • 3 Beds
    • 3 Baths
    • 3,238 Home (sqft)
    • 3 Baths
    • 5.33 Lot (ac)
    Listed with William Raveis R.E. & Home Services
  9. Photo of 3034 E Concord St #20, Boston, MA 02118 (MLS # 73228091)
    $799,900
    Photo of 3034 E Concord St #20, Boston, MA 02118 (MLS # 73228091)
    Photo of 3034 E Concord St #20, Boston, MA 02118 (MLS # 73228091)
    24
     
    3034 E Concord St #20, Boston, MA
    3034 E Concord St #20
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 886 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
    Listed with Compass
  10. Photo of 57 Kirkland Street, Cambridge, MA 02138 (MLS # 73229817)
    $1,930,000
    Photo of 57 Kirkland Street, Cambridge, MA 02138 (MLS # 73229817)
    Photo of 57 Kirkland Street, Cambridge, MA 02138 (MLS # 73229817)
    33
     
    57 Kirkland Street, Cambridge, MA
    57 Kirkland Street
    Cambridge, MA
    • 4 Beds
    • 3 Baths
    • 2,900 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
    Listed with Benoit Real Estate Group ,LLC
  11. Photo of 312320 W 3rd St #204, Boston, MA 02127 (MLS # 73229813)
    $899,000
    Photo of 312320 W 3rd St #204, Boston, MA 02127 (MLS # 73229813)
    Photo of 312320 W 3rd St #204, Boston, MA 02127 (MLS # 73229813)
    17
     
    312320 W 3rd St #204, Boston, MA
    312320 W 3rd St #204
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,230 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
    Listed with 360 Realty LLC
  12. Photo of 10 Boardman Ave, Manchester, MA 01944 (MLS # 73229809)
    $15,775,000
    Photo of 10 Boardman Ave, Manchester, MA 01944 (MLS # 73229809)
    Photo of 10 Boardman Ave, Manchester, MA 01944 (MLS # 73229809)
    42
     
    10 Boardman Ave, Manchester, MA
    10 Boardman Ave
    Manchester, MA
    • 6 Beds
    • 11 Baths
    • 12,893 Home (sqft)
    • 11 Baths
    • 1.59 Lot (ac)
    Listed with J. Barrett & Company
  13. Photo of 37 Montvale Avenue #11, Woburn, MA 01801 (MLS # 73229807)
    $337,770
    Photo of 37 Montvale Avenue #11, Woburn, MA 01801 (MLS # 73229807)
    Photo of 37 Montvale Avenue #11, Woburn, MA 01801 (MLS # 73229807)
    18
     
    37 Montvale Avenue #11, Woburn, MA
    37 Montvale Avenue #11
    Woburn, MA
    • 1 Bed
    • 1 Bath
    • 715 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with John Daniel Shipman and Associates, LLC
  14. Photo of 233235 London St, Boston, MA 02128 (MLS # 73229797)
    $1,050,000
    Photo of 233235 London St, Boston, MA 02128 (MLS # 73229797)
    Photo of 233235 London St, Boston, MA 02128 (MLS # 73229797)
    22
     
    233235 London St, Boston, MA
    233235 London St
    Boston, MA
    • 4 Beds
    • 3 Baths
    • 2,336 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
    Listed with Prestige Property Solutions, Inc.
  15. Photo of 3 Spring Hill Farm Road, Wenham, MA 01984 (MLS # 73229795)
    $1,949,900
    Photo of 3 Spring Hill Farm Road, Wenham, MA 01984 (MLS # 73229795)
    Photo of 3 Spring Hill Farm Road, Wenham, MA 01984 (MLS # 73229795)
    42
     
    3 Spring Hill Farm Road, Wenham, MA
    3 Spring Hill Farm Road
    Wenham, MA
    • 5 Beds
    • 4 Baths
    • 3,695 Home (sqft)
    • 4 Baths
    • 40,076 Lot (sqft)
    Listed with Coldwell Banker Realty - Beverly
  16. Photo of 55 Woodland Rd, Wayland, MA 01778 (MLS # 73229798)
    $999,000
    Photo of 55 Woodland Rd, Wayland, MA 01778 (MLS # 73229798)
    Photo of 55 Woodland Rd, Wayland, MA 01778 (MLS # 73229798)
    39
     
    55 Woodland Rd, Wayland, MA
    55 Woodland Rd
    Wayland, MA
    • 3 Beds
    • 3 Baths
    • 1,947 Home (sqft)
    • 3 Baths
    • 11,326 Lot (sqft)
    Listed with eRealty Advisors, Inc.
  17. Photo of 5205 Washington St #402, Boston, MA 02132 (MLS # 73229792)
    $775,000
    Photo of 5205 Washington St #402, Boston, MA 02132 (MLS # 73229792)
    Photo of 5205 Washington St #402, Boston, MA 02132 (MLS # 73229792)
    21
     
    5205 Washington St #402, Boston, MA
    5205 Washington St #402
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 1,117 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Citylife Real Estate
  18. Photo of 8 Hardy Ln, Essex, MA 01929 (MLS # 73229788)
    $1,425,000
    Photo of 8 Hardy Ln, Essex, MA 01929 (MLS # 73229788)
    Photo of 8 Hardy Ln, Essex, MA 01929 (MLS # 73229788)
    42
     
    8 Hardy Ln, Essex, MA
    8 Hardy Ln
    Essex, MA
    • 3 Beds
    • 3 Baths
    • 2,155 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
    Listed with LandVest, Inc., Ipswich
  19. Photo of 80 South St #9, Fitchburg, MA 01420 (MLS # 73229785)
    $289,900
    Photo of 80 South St #9, Fitchburg, MA 01420 (MLS # 73229785)
    Photo of 80 South St #9, Fitchburg, MA 01420 (MLS # 73229785)
    35
     
    80 South St #9, Fitchburg, MA
    80 South St #9
    Fitchburg, MA
    • 1 Bed
    • 1 Bath
    • 844 Home (sqft)
    • 1 Bath
    • 31,799 Lot (sqft)
    Listed with Coldwell Banker Realty - Leominster
  20. Photo of 287 Captain Eames Cir #287, Ashland, MA 01721 (MLS # 73229784)
    $589,900
    Photo of 287 Captain Eames Cir #287, Ashland, MA 01721 (MLS # 73229784)
    Photo of 287 Captain Eames Cir #287, Ashland, MA 01721 (MLS # 73229784)
    32
     
    287 Captain Eames Cir #287, Ashland, MA
    287 Captain Eames Cir #287
    Ashland, MA
    • 2 Beds
    • 3 Baths
    • 2,159 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Apex Realty Group, LLC
  21. Photo of 2 Canfield St, Westborough, MA 01581 (MLS # 73229782)
    $499,900
    Photo of 2 Canfield St, Westborough, MA 01581 (MLS # 73229782)
    Photo of 2 Canfield St, Westborough, MA 01581 (MLS # 73229782)
    28
     
    2 Canfield St, Westborough, MA
    2 Canfield St
    Westborough, MA
    • 3 Beds
    • 2 Baths
    • 1,104 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
    Listed with Walter Aldrich Realty
  22. Photo of 20 Murray St, Plymouth, MA 02360 (MLS # 73229780)
    $689,500
    Photo of 20 Murray St, Plymouth, MA 02360 (MLS # 73229780)
    Photo of 20 Murray St, Plymouth, MA 02360 (MLS # 73229780)
    19
     
    20 Murray St, Plymouth, MA
    20 Murray St
    Plymouth, MA
    • 2 Beds
    • 2 Baths
    • 1,735 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
    Listed with Conway - Plymouth
  23. Photo of 272 Amity St, Amherst, MA 01002 (MLS # 73229775)
    $895,000
    Photo of 272 Amity St, Amherst, MA 01002 (MLS # 73229775)
    Photo of 272 Amity St, Amherst, MA 01002 (MLS # 73229775)
    35
     
    272 Amity St, Amherst, MA
    272 Amity St
    Amherst, MA
    • 3 Beds
    • 3 Baths
    • 1,915 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
    Listed with The Virtual Realty Group
  24. Photo of 4 Sabatinelli Road, Milford, MA 01757 (MLS # 73229773)
    $399,000
    Photo of 4 Sabatinelli Road, Milford, MA 01757 (MLS # 73229773)
    Photo of 4 Sabatinelli Road, Milford, MA 01757 (MLS # 73229773)
    4 Sabatinelli Road, Milford, MA
    4 Sabatinelli Road
    Milford, MA
    • 2 Beds
    • 2 Baths
    • 1,470 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
    Listed with Hammond Residential Real Estate
  25. Photo of 7 Oxford St, Chicopee, MA 01020 (MLS # 73229772)
    $289,900
    Photo of 7 Oxford St, Chicopee, MA 01020 (MLS # 73229772)
    Photo of 7 Oxford St, Chicopee, MA 01020 (MLS # 73229772)
    21
     
    7 Oxford St, Chicopee, MA
    7 Oxford St
    Chicopee, MA
    • 2 Beds
    • 1 Bath
    • 984 Home (sqft)
    • 1 Bath
    • 8,712 Lot (sqft)
    Listed with Naples Realty Group
  26. Photo of 3 Ruth Dr, Framingham, MA 01701 (MLS # 73229771)
    $615,000
    Photo of 3 Ruth Dr, Framingham, MA 01701 (MLS # 73229771)
    Photo of 3 Ruth Dr, Framingham, MA 01701 (MLS # 73229771)
    35
     
    3 Ruth Dr, Framingham, MA
    3 Ruth Dr
    Framingham, MA
    • 3 Beds
    • 2 Baths
    • 1,716 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
    Listed with RE/MAX Executive Realty
  27. Photo of 95 W Shore Road, Windham, NH 03087 (MLS # 73229767)
    $1,999,999
    Photo of 95 W Shore Road, Windham, NH 03087 (MLS # 73229767)
    Photo of 95 W Shore Road, Windham, NH 03087 (MLS # 73229767)
    30
     
    95 W Shore Road, Windham, NH
    95 W Shore Road
    Windham, NH
    • 2 Beds
    • 2 Baths
    • 3,350 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Verani Realty
  28. Photo of 91 Phoebe St #91, Methuen, MA 01844 (MLS # 73229768)
    $899,900
    Photo of 91 Phoebe St #91, Methuen, MA 01844 (MLS # 73229768)
    Photo of 91 Phoebe St #91, Methuen, MA 01844 (MLS # 73229768)
    41
     
    91 Phoebe St #91, Methuen, MA
    91 Phoebe St #91
    Methuen, MA
    • 2 Beds
    • 4 Baths
    • 3,262 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with JD Advisors, Inc
  29. Photo of 35 Richard St, Worcester, MA 01603 (MLS # 73229765)
    $279,900
    Photo of 35 Richard St, Worcester, MA 01603 (MLS # 73229765)
    Photo of 35 Richard St, Worcester, MA 01603 (MLS # 73229765)
    19
     
    35 Richard St, Worcester, MA
    35 Richard St
    Worcester, MA
    • 3 Beds
    • 0 Baths
    • 4,037 Home (sqft)
    • 0 Baths
    • 11,762 Lot (sqft)
    Listed with Media Realty Group Inc.
  30. Photo of 24 Faxon St #6, Stoughton, MA 02072 (MLS # 73229758)
    $249,900
    Photo of 24 Faxon St #6, Stoughton, MA 02072 (MLS # 73229758)
    Photo of 24 Faxon St #6, Stoughton, MA 02072 (MLS # 73229758)
    15
     
    24 Faxon St #6, Stoughton, MA
    24 Faxon St #6
    Stoughton, MA
    • 2 Beds
    • 1 Bath
    • 970 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with CUE 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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Alexa Dealy, Realtor® RE/MAX Andrew Realty Services Hours: 9:00 am – 7:00 pm

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