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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 3/29/2024)

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  1. Photo of 189 Old Worcester Rd, Charlton, MA 01507 (MLS # 73215473)
    $375,000
    Photo of 189 Old Worcester Rd, Charlton, MA 01507 (MLS # 73215473)
    Photo of 189 Old Worcester Rd, Charlton, MA 01507 (MLS # 73215473)
    38
     
    189 Old Worcester Rd, Charlton, MA
    189 Old Worcester Rd
    Charlton, MA
    • 2 Beds
    • 1 Bath
    • 1,500 Home (sqft)
    • 1 Bath
    • 29,186 Lot (sqft)
    Listed with ERA Key Realty Services - Alliance Realty, Inc.
  2. Photo of 1 Plant Avenue, Hudson, MA 01749 (MLS # 73217402)
    $524,900
    Photo of 1 Plant Avenue, Hudson, MA 01749 (MLS # 73217402)
    Photo of 1 Plant Avenue, Hudson, MA 01749 (MLS # 73217402)
    29
     
    1 Plant Avenue, Hudson, MA
    1 Plant Avenue
    Hudson, MA
    • 3 Beds
    • 2 Baths
    • 1,451 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
    Listed with ERA Key Realty Services - Distinctive Group
  3. Photo of 156 Brooks Village Rd, Templeton, MA 01468 (MLS # 73217401)
    $165,000
    Photo of 156 Brooks Village Rd, Templeton, MA 01468 (MLS # 73217401)
    Photo of 156 Brooks Village Rd, Templeton, MA 01468 (MLS # 73217401)
    12
     
    156 Brooks Village Rd, Templeton, MA
    156 Brooks Village Rd
    Templeton, MA
    • 4 Beds
    • 1 Bath
    • 1,075 Home (sqft)
    • 1 Bath
    • 15,682 Lot (sqft)
    Listed with ERA Key Realty Services - Worcester
  4. Photo of 93 Sedgwick Street, Boston, MA 02130 (MLS # 73217400)
    $2,225,000
    Photo of 93 Sedgwick Street, Boston, MA 02130 (MLS # 73217400)
    Photo of 93 Sedgwick Street, Boston, MA 02130 (MLS # 73217400)
    10
     
    93 Sedgwick Street, Boston, MA
    93 Sedgwick Street
    Boston, MA
    • 0 Beds
    • 6 Baths
    • 8,329 Home (sqft)
    • 6 Baths
    • 10,890 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  5. Photo of 105 Warren Ave, Marlborough, MA 01752 (MLS # 73217397)
    $564,900
    Photo of 105 Warren Ave, Marlborough, MA 01752 (MLS # 73217397)
    Photo of 105 Warren Ave, Marlborough, MA 01752 (MLS # 73217397)
    36
     
    105 Warren Ave, Marlborough, MA
    105 Warren Ave
    Marlborough, MA
    • 3 Beds
    • 2 Baths
    • 1,554 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
    Listed with 29 Realty Group, Inc.
  6. Photo of 82 Circuit Rd, Medford, MA 02155 (MLS # 73217393)
    $849,900
    Photo of 82 Circuit Rd, Medford, MA 02155 (MLS # 73217393)
    Photo of 82 Circuit Rd, Medford, MA 02155 (MLS # 73217393)
    25
     
    82 Circuit Rd, Medford, MA
    82 Circuit Rd
    Medford, MA
    • 3 Beds
    • 2 Baths
    • 1,610 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
    Listed with Vicente Realty, LLC
  7. Photo of 16 Old Coach Rd, Braintree, MA 02184 (MLS # 73217394)
    $839,000
    Photo of 16 Old Coach Rd, Braintree, MA 02184 (MLS # 73217394)
    Photo of 16 Old Coach Rd, Braintree, MA 02184 (MLS # 73217394)
    42
     
    16 Old Coach Rd, Braintree, MA
    16 Old Coach Rd
    Braintree, MA
    • 4 Beds
    • 3 Baths
    • 2,108 Home (sqft)
    • 3 Baths
    • 23,958 Lot (sqft)
    Listed with Keller Williams Realty
  8. Photo of 239 New Braintree Rd, West Brookfield, MA 01585 (MLS # 73217383)
    $849,900
    Photo of 239 New Braintree Rd, West Brookfield, MA 01585 (MLS # 73217383)
    Photo of 239 New Braintree Rd, West Brookfield, MA 01585 (MLS # 73217383)
    42
     
    239 New Braintree Rd, West Brookfield, MA
    239 New Braintree Rd
    West Brookfield, MA
    • 4 Beds
    • 3 Baths
    • 2,456 Home (sqft)
    • 3 Baths
    • 5.40 Lot (ac)
    Listed with William Neylon Real Est.
  9. Photo of 196 Shawsheen Ave, Wilmington, MA 01887 (MLS # 73217387)
    $874,900
    Photo of 196 Shawsheen Ave, Wilmington, MA 01887 (MLS # 73217387)
    Photo of 196 Shawsheen Ave, Wilmington, MA 01887 (MLS # 73217387)
    28
     
    196 Shawsheen Ave, Wilmington, MA
    196 Shawsheen Ave
    Wilmington, MA
    • 3 Beds
    • 2 Baths
    • 2,362 Home (sqft)
    • 2 Baths
    • 28,314 Lot (sqft)
    Listed with LAER Realty Partners
  10. Photo of 98 Willow Street, Quincy, MA 02170 (MLS # 73217379)
    $900,000
    Photo of 98 Willow Street, Quincy, MA 02170 (MLS # 73217379)
    Photo of 98 Willow Street, Quincy, MA 02170 (MLS # 73217379)
    16
     
    98 Willow Street, Quincy, MA
    98 Willow Street
    Quincy, MA
    • 5 Beds
    • 3 Baths
    • 2,350 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
    Listed with Classic Homes Real Estate
  11. Photo of 24 Baxter Ave, Quincy, MA 02169 (MLS # 73217385)
    $499,900
    Photo of 24 Baxter Ave, Quincy, MA 02169 (MLS # 73217385)
    Photo of 24 Baxter Ave, Quincy, MA 02169 (MLS # 73217385)
    10
     
    24 Baxter Ave, Quincy, MA
    24 Baxter Ave
    Quincy, MA
    • 2 Beds
    • 1 Bath
    • 874 Home (sqft)
    • 1 Bath
    • 5,663 Lot (sqft)
    Listed with Success! Real Estate
  12. Photo of 4 Quinns Way #4, Mashpee, MA 02649 (MLS # 73217389)
    $975,000
    Photo of 4 Quinns Way #4, Mashpee, MA 02649 (MLS # 73217389)
    Photo of 4 Quinns Way #4, Mashpee, MA 02649 (MLS # 73217389)
    29
     
    4 Quinns Way #4, Mashpee, MA
    4 Quinns Way #4
    Mashpee, MA
    • 2 Beds
    • 4 Baths
    • 2,800 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Realty
  13. Photo of 57 Almont St, Malden, MA 02148 (MLS # 73217373)
    $559,000
    Photo of 57 Almont St, Malden, MA 02148 (MLS # 73217373)
    Photo of 57 Almont St, Malden, MA 02148 (MLS # 73217373)
    16
     
    57 Almont St, Malden, MA
    57 Almont St
    Malden, MA
    • 5 Beds
    • 2 Baths
    • 2,387 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
    Listed with Century 21 North East
  14. Photo of 9 Juneau Ave #9, Haverhill, MA 01832 (MLS # 73217375)
    $265,000
    Photo of 9 Juneau Ave #9, Haverhill, MA 01832 (MLS # 73217375)
    Photo of 9 Juneau Ave #9, Haverhill, MA 01832 (MLS # 73217375)
    20
     
    9 Juneau Ave #9, Haverhill, MA
    9 Juneau Ave #9
    Haverhill, MA
    • 3 Beds
    • 4 Baths
    • 1,875 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with LAER Realty Partners
  15. Photo of 1 Hatch Rd, Acton, MA 01720 (MLS # 73217372)
    $899,000
    Photo of 1 Hatch Rd, Acton, MA 01720 (MLS # 73217372)
    Photo of 1 Hatch Rd, Acton, MA 01720 (MLS # 73217372)
    30
     
    1 Hatch Rd, Acton, MA
    1 Hatch Rd
    Acton, MA
    • 4 Beds
    • 3 Baths
    • 2,307 Home (sqft)
    • 3 Baths
    • 1.76 Lot (ac)
    Listed with Keller Williams Realty Boston Northwest
  16. Photo of 769 Allen St, Springfield, MA 01118 (MLS # 73217377)
    $335,000
    Photo of 769 Allen St, Springfield, MA 01118 (MLS # 73217377)
    Photo of 769 Allen St, Springfield, MA 01118 (MLS # 73217377)
    35
     
    769 Allen St, Springfield, MA
    769 Allen St
    Springfield, MA
    • 3 Beds
    • 2 Baths
    • 1,662 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
    Listed with Coldwell Banker Realty - Western MA
  17. Photo of 15 Greystone Ave, Webster, MA 01570 (MLS # 73217371)
    $514,900
    Photo of 15 Greystone Ave, Webster, MA 01570 (MLS # 73217371)
    Photo of 15 Greystone Ave, Webster, MA 01570 (MLS # 73217371)
    32
     
    15 Greystone Ave, Webster, MA
    15 Greystone Ave
    Webster, MA
    • 8 Beds
    • 3 Baths
    • 2,695 Home (sqft)
    • 3 Baths
    • 11,762 Lot (sqft)
    Listed with 1 Worcester Homes
  18. Photo of 33 Hancock Street, Cambridge, MA 02139 (MLS # 73217369)
    $1,400,000
    Photo of 33 Hancock Street, Cambridge, MA 02139 (MLS # 73217369)
    Photo of 33 Hancock Street, Cambridge, MA 02139 (MLS # 73217369)
    12
     
    33 Hancock Street, Cambridge, MA
    33 Hancock Street
    Cambridge, MA
    • 6 Beds
    • 3 Baths
    • 2,979 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
    Listed with Alan Fincke
  19. Photo of 25 Barry Street, Boston, MA 02125 (MLS # 73217363)
    $1,249,950
    Photo of 25 Barry Street, Boston, MA 02125 (MLS # 73217363)
    Photo of 25 Barry Street, Boston, MA 02125 (MLS # 73217363)
    11
     
    25 Barry Street, Boston, MA
    25 Barry Street
    Boston, MA
    • 11 Beds
    • 3 Baths
    • 3,583 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
    Listed with The Agency
  20. Photo of 558 Fox Hill Rd, Chatham, MA 02633 (MLS # 73217365)
    $1,569,000
    Photo of 558 Fox Hill Rd, Chatham, MA 02633 (MLS # 73217365)
    Photo of 558 Fox Hill Rd, Chatham, MA 02633 (MLS # 73217365)
    32
     
    558 Fox Hill Rd, Chatham, MA
    558 Fox Hill Rd
    Chatham, MA
    • 5 Beds
    • 10 Baths
    • 11,000 Home (sqft)
    • 10 Baths
    • 2.74 Lot (ac)
    Listed with Corcoran Property Advisors
  21. Photo of 50 Helena Street, Leominster, MA 01453 (MLS # 73217366)
    $599,900
    Photo of 50 Helena Street, Leominster, MA 01453 (MLS # 73217366)
    Photo of 50 Helena Street, Leominster, MA 01453 (MLS # 73217366)
    39
     
    50 Helena Street, Leominster, MA
    50 Helena Street
    Leominster, MA
    • 4 Beds
    • 2 Baths
    • 2,548 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  22. Photo of 140 Greenwich Plains Rd, Ware, MA 01082 (MLS # 73217361)
    $389,000
    Photo of 140 Greenwich Plains Rd, Ware, MA 01082 (MLS # 73217361)
    Photo of 140 Greenwich Plains Rd, Ware, MA 01082 (MLS # 73217361)
    42
     
    140 Greenwich Plains Rd, Ware, MA
    140 Greenwich Plains Rd
    Ware, MA
    • 5 Beds
    • 2 Baths
    • 2,284 Home (sqft)
    • 2 Baths
    • 2.21 Lot (ac)
    Listed with ROVI Homes
  23. Photo of 5 Northside Rd, Charlton, MA 01507 (MLS # 73217358)
    $749,900
    Photo of 5 Northside Rd, Charlton, MA 01507 (MLS # 73217358)
    Photo of 5 Northside Rd, Charlton, MA 01507 (MLS # 73217358)
    5 Northside Rd, Charlton, MA
    5 Northside Rd
    Charlton, MA
    • 4 Beds
    • 3 Baths
    • 2,300 Home (sqft)
    • 3 Baths
    • 19.99 Lot (ac)
    Listed with RE/MAX Prof Associates
  24. Photo of 29 Eugene Drive, Belchertown, MA 01007 (MLS # 73217351)
    $599,900
    Photo of 29 Eugene Drive, Belchertown, MA 01007 (MLS # 73217351)
    Photo of 29 Eugene Drive, Belchertown, MA 01007 (MLS # 73217351)
    42
     
    29 Eugene Drive, Belchertown, MA
    29 Eugene Drive
    Belchertown, MA
    • 3 Beds
    • 3 Baths
    • 2,916 Home (sqft)
    • 3 Baths
    • 1.14 Lot (ac)
    Listed with Kelley & Katzer Real Estate, LLC
  25. Photo of 96 King St #2, Boston, MA 02122 (MLS # 73217353)
    $639,900
    Photo of 96 King St #2, Boston, MA 02122 (MLS # 73217353)
    Photo of 96 King St #2, Boston, MA 02122 (MLS # 73217353)
    25
     
    96 King St #2, Boston, MA
    96 King St #2
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 950 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  26. Photo of 7 Main Street #104, Brockton, MA 02031 (MLS # 73217352)
    $199,000
    Photo of 7 Main Street #104, Brockton, MA 02031 (MLS # 73217352)
    Photo of 7 Main Street #104, Brockton, MA 02031 (MLS # 73217352)
    19
     
    7 Main Street #104, Brockton, MA
    7 Main Street #104
    Brockton, MA
    • 1 Bed
    • 1 Bath
    • 643 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  27. Photo of 32 Ingram Rd, Leicester, MA 01611 (MLS # 73217354)
    $399,000
    Photo of 32 Ingram Rd, Leicester, MA 01611 (MLS # 73217354)
    Photo of 32 Ingram Rd, Leicester, MA 01611 (MLS # 73217354)
    29
     
    32 Ingram Rd, Leicester, MA
    32 Ingram Rd
    Leicester, MA
    • 3 Beds
    • 1 Bath
    • 1,613 Home (sqft)
    • 1 Bath
    • 20,474 Lot (sqft)
    Listed with Coldwell Banker Realty - Worcester
  28. Photo of 14 Arbor Lane, Dedham, MA 02026 (MLS # 73217347)
    $325,000
    Photo of 14 Arbor Lane, Dedham, MA 02026 (MLS # 73217347)
    Photo of 14 Arbor Lane, Dedham, MA 02026 (MLS # 73217347)
    14 Arbor Lane, Dedham, MA
    14 Arbor Lane
    Dedham, MA
    • 2 Beds
    • 2 Baths
    • 924 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
    Listed with Better Living Real Estate, LLC
  29. Photo of 355 Pond St, Uxbridge, MA 01569 (MLS # 73217346)
    $1,699,000
    Photo of 355 Pond St, Uxbridge, MA 01569 (MLS # 73217346)
    Photo of 355 Pond St, Uxbridge, MA 01569 (MLS # 73217346)
    42
     
    355 Pond St, Uxbridge, MA
    355 Pond St
    Uxbridge, MA
    • 4 Beds
    • 4 Baths
    • 5,619 Home (sqft)
    • 4 Baths
    • 16.54 Lot (ac)
    Listed with RE/MAX Executive Realty
  30. Photo of 194 Franklin St #2, Cambridge, MA 02139 (MLS # 73217348)
    $1,598,000
    Photo of 194 Franklin St #2, Cambridge, MA 02139 (MLS # 73217348)
    Photo of 194 Franklin St #2, Cambridge, MA 02139 (MLS # 73217348)
    21
     
    194 Franklin St #2, Cambridge, MA
    194 Franklin St #2
    Cambridge, MA
    • 3 Beds
    • 4 Baths
    • 1,662 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with HMW Real Estate, LLC
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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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