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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 39 Bonner Ave #2, Medford, MA 02155 (MLS # 73229686)
    $1,250,000
    Photo of 39 Bonner Ave #2, Medford, MA 02155 (MLS # 73229686)
    Photo of 39 Bonner Ave #2, Medford, MA 02155 (MLS # 73229686)
    17
     
    39 Bonner Ave #2, Medford, MA
    39 Bonner Ave #2
    Medford, MA
    • 4 Beds
    • 2 Baths
    • 1,948 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with 360 Realty LLC
  2. Photo of 41 Bonner Ave #1, Medford, MA 02155 (MLS # 73229680)
    $1,050,000
    Photo of 41 Bonner Ave #1, Medford, MA 02155 (MLS # 73229680)
    Photo of 41 Bonner Ave #1, Medford, MA 02155 (MLS # 73229680)
    17
     
    41 Bonner Ave #1, Medford, MA
    41 Bonner Ave #1
    Medford, MA
    • 4 Beds
    • 3 Baths
    • 2,167 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with 360 Realty LLC
  3. Photo of 426 Alpine Dr, Southbridge, MA 01564 (MLS # 73229679)
    $499,500
    Photo of 426 Alpine Dr, Southbridge, MA 01564 (MLS # 73229679)
    Photo of 426 Alpine Dr, Southbridge, MA 01564 (MLS # 73229679)
    35
     
    426 Alpine Dr, Southbridge, MA
    426 Alpine Dr
    Southbridge, MA
    • 3 Beds
    • 3 Baths
    • 1,750 Home (sqft)
    • 3 Baths
    • 43,560 Lot (sqft)
    Listed with One Way Realty
  4. Photo of 3941 Bonner Ave, Medford, MA 02155 (MLS # 73229676)
    $2,300,000
    Photo of 3941 Bonner Ave, Medford, MA 02155 (MLS # 73229676)
    Photo of 3941 Bonner Ave, Medford, MA 02155 (MLS # 73229676)
    31
     
    3941 Bonner Ave, Medford, MA
    3941 Bonner Ave
    Medford, MA
    • 8 Beds
    • 5 Baths
    • 4,115 Home (sqft)
    • 5 Baths
    • 3,921 Lot (sqft)
    Listed with 360 Realty LLC
  5. Photo of 481 E Main St, Fall River, MA 02724 (MLS # 73229675)
    $675,000
    Photo of 481 E Main St, Fall River, MA 02724 (MLS # 73229675)
    Photo of 481 E Main St, Fall River, MA 02724 (MLS # 73229675)
    37
     
    481 E Main St, Fall River, MA
    481 E Main St
    Fall River, MA
    • 9 Beds
    • 3 Baths
    • 4,269 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
    Listed with RE/MAX Vantage
  6. Photo of 42 Lawson Road, Westford, MA 01886 (MLS # 73229670)
    $2,175,000
    Photo of 42 Lawson Road, Westford, MA 01886 (MLS # 73229670)
    Photo of 42 Lawson Road, Westford, MA 01886 (MLS # 73229670)
    42
     
    42 Lawson Road, Westford, MA
    42 Lawson Road
    Westford, MA
    • 4 Beds
    • 4 Baths
    • 4,041 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
    Listed with Keller Williams Realty-Merrimack
  7. Photo of 97 Alderman St, Springfield, MA 01108 (MLS # 73229661)
    $495,000
    Photo of 97 Alderman St, Springfield, MA 01108 (MLS # 73229661)
    Photo of 97 Alderman St, Springfield, MA 01108 (MLS # 73229661)
    10
     
    97 Alderman St, Springfield, MA
    97 Alderman St
    Springfield, MA
    • 6 Beds
    • 4 Baths
    • 5,000 Home (sqft)
    • 4 Baths
    • 4,792 Lot (sqft)
    Listed with Naples Realty Group
  8. Photo of 84 Lowther Road, Framingham, MA 01701 (MLS # 73229657)
    $499,000
    Photo of 84 Lowther Road, Framingham, MA 01701 (MLS # 73229657)
    Photo of 84 Lowther Road, Framingham, MA 01701 (MLS # 73229657)
    16
     
    84 Lowther Road, Framingham, MA
    84 Lowther Road
    Framingham, MA
    • 3 Beds
    • 1 Bath
    • 1,392 Home (sqft)
    • 1 Bath
    • 10,019 Lot (sqft)
    Listed with Realty Executives Boston West
  9. Photo of 11 Howard St, Westfield, MA 01085 (MLS # 73229654)
    $424,900
    Photo of 11 Howard St, Westfield, MA 01085 (MLS # 73229654)
    Photo of 11 Howard St, Westfield, MA 01085 (MLS # 73229654)
    36
     
    11 Howard St, Westfield, MA
    11 Howard St
    Westfield, MA
    • 9 Beds
    • 2 Baths
    • 2,799 Home (sqft)
    • 2 Baths
    • 9,148 Lot (sqft)
    Listed with Landmark, REALTORS®
  10. Photo of 4 Church St, Middleton, MA 01949 (MLS # 73229652)
    $1,175,000
    Photo of 4 Church St, Middleton, MA 01949 (MLS # 73229652)
    Photo of 4 Church St, Middleton, MA 01949 (MLS # 73229652)
    4 Church St, Middleton, MA
    4 Church St
    Middleton, MA
    • 4 Beds
    • 3 Baths
    • 3,300 Home (sqft)
    • 3 Baths
    • 20,038 Lot (sqft)
    Listed with Noble Realty Partners LLC
  11. Photo of 12 Lasell St, Boston, MA 02132 (MLS # 73229650)
    $775,700
    Photo of 12 Lasell St, Boston, MA 02132 (MLS # 73229650)
    Photo of 12 Lasell St, Boston, MA 02132 (MLS # 73229650)
    22
     
    12 Lasell St, Boston, MA
    12 Lasell St
    Boston, MA
    • 3 Beds
    • 2 Baths
    • 1,976 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  12. Photo of 13 Salli Cir, Ludlow, MA 01056 (MLS # 73229644)
    $380,000
    Photo of 13 Salli Cir, Ludlow, MA 01056 (MLS # 73229644)
    Photo of 13 Salli Cir, Ludlow, MA 01056 (MLS # 73229644)
    41
     
    13 Salli Cir, Ludlow, MA
    13 Salli Cir
    Ludlow, MA
    • 3 Beds
    • 1 Bath
    • 1,194 Home (sqft)
    • 1 Bath
    • 15,246 Lot (sqft)
    Listed with Lock and Key Realty Inc.
  13. Photo of 32 Rockwell Ave, Medford, MA 02155 (MLS # 73229646)
    $635,000
    Photo of 32 Rockwell Ave, Medford, MA 02155 (MLS # 73229646)
    Photo of 32 Rockwell Ave, Medford, MA 02155 (MLS # 73229646)
    32 Rockwell Ave, Medford, MA
    32 Rockwell Ave
    Medford, MA
    • 3 Beds
    • 1 Bath
    • 1,612 Home (sqft)
    • 1 Bath
    • 5,663 Lot (sqft)
    Listed with eXp Realty
  14. Photo of 121 Downer Ave, Hingham, MA 02043 (MLS # 73229630)
    $2,499,000
    Photo of 121 Downer Ave, Hingham, MA 02043 (MLS # 73229630)
    Photo of 121 Downer Ave, Hingham, MA 02043 (MLS # 73229630)
    28
     
    121 Downer Ave, Hingham, MA
    121 Downer Ave
    Hingham, MA
    • 3 Beds
    • 3 Baths
    • 2,642 Home (sqft)
    • 3 Baths
    • 22,652 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  15. Photo of 394396 W Main St, Avon, MA 02322 (MLS # 73229627)
    $899,000
    Photo of 394396 W Main St, Avon, MA 02322 (MLS # 73229627)
    Photo of 394396 W Main St, Avon, MA 02322 (MLS # 73229627)
    38
     
    394396 W Main St, Avon, MA
    394396 W Main St
    Avon, MA
    • 5 Beds
    • 3 Baths
    • 4,512 Home (sqft)
    • 3 Baths
    • 24,830 Lot (sqft)
    Listed with HomeSmart First Class Realty
  16. Photo of 5 Marc Dr #5 A 4, Plymouth, MA 02360 (MLS # 73229626)
    $320,000
    Photo of 5 Marc Dr #5 A 4, Plymouth, MA 02360 (MLS # 73229626)
    Photo of 5 Marc Dr #5 A 4, Plymouth, MA 02360 (MLS # 73229626)
    16
     
    5 Marc Dr #5 A 4, Plymouth, MA
    5 Marc Dr #5 A 4
    Plymouth, MA
    • 2 Beds
    • 2 Baths
    • 948 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Integrity First Real Estate
  17. Photo of 53 Richardson Drive #294, Millis, MA 02054 (MLS # 73229629)
    $974,995
    Photo of 53 Richardson Drive #294, Millis, MA 02054 (MLS # 73229629)
    Photo of 53 Richardson Drive #294, Millis, MA 02054 (MLS # 73229629)
    53 Richardson Drive #294, Millis, MA
    53 Richardson Drive #294
    Millis, MA
    • 2 Beds
    • 3 Baths
    • 2,465 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Toll Brothers Real Estate
  18. Photo of 10 Evergreen Way #97, Tyngsborough, MA 01879 (MLS # 73229624)
    $829,995
    Photo of 10 Evergreen Way #97, Tyngsborough, MA 01879 (MLS # 73229624)
    Photo of 10 Evergreen Way #97, Tyngsborough, MA 01879 (MLS # 73229624)
    10 Evergreen Way #97, Tyngsborough, MA
    10 Evergreen Way #97
    Tyngsborough, MA
    • 2 Beds
    • 2 Baths
    • 1,913 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Toll Brothers Real Estate
  19. Photo of 580 Washington St #PH2, Boston, MA 02111 (MLS # 73229623)
    $3,490,000
    Photo of 580 Washington St #PH2, Boston, MA 02111 (MLS # 73229623)
    Photo of 580 Washington St #PH2, Boston, MA 02111 (MLS # 73229623)
    38
     
    580 Washington St #PH2, Boston, MA
    580 Washington St #PH2
    Boston, MA
    • 3 Beds
    • 3 Baths
    • 2,348 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
    Listed with First Boston Realty International
  20. Photo of 55 Gay St, Stoughton, MA 02072 (MLS # 73229621)
    $1,098,990
    Photo of 55 Gay St, Stoughton, MA 02072 (MLS # 73229621)
    Photo of 55 Gay St, Stoughton, MA 02072 (MLS # 73229621)
    10
     
    55 Gay St, Stoughton, MA
    55 Gay St
    Stoughton, MA
    • 5 Beds
    • 3 Baths
    • 3,316 Home (sqft)
    • 3 Baths
    • 20,474 Lot (sqft)
    Listed with Get Listed Realty, LLC
  21. Photo of 23 Old Sunderland Rd, Montague, MA 01351 (MLS # 73229619)
    $215,000
    Photo of 23 Old Sunderland Rd, Montague, MA 01351 (MLS # 73229619)
    Photo of 23 Old Sunderland Rd, Montague, MA 01351 (MLS # 73229619)
    42
     
    23 Old Sunderland Rd, Montague, MA
    23 Old Sunderland Rd
    Montague, MA
    • 3 Beds
    • 2 Baths
    • 1,566 Home (sqft)
    • 2 Baths
    • 2.00 Lot (ac)
    Listed with Keller Williams Realty North Central
  22. Photo of 53 Myrtle Ave, Webster, MA 01570 (MLS # 73229617)
    $449,900
    Photo of 53 Myrtle Ave, Webster, MA 01570 (MLS # 73229617)
    Photo of 53 Myrtle Ave, Webster, MA 01570 (MLS # 73229617)
    10
     
    53 Myrtle Ave, Webster, MA
    53 Myrtle Ave
    Webster, MA
    • 3 Beds
    • 2 Baths
    • 1,300 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
    Listed with Get Listed Realty, LLC
  23. Photo of 181 Dyer St, Gardner, MA 01440 (MLS # 73229611)
    $350,000
    Photo of 181 Dyer St, Gardner, MA 01440 (MLS # 73229611)
    Photo of 181 Dyer St, Gardner, MA 01440 (MLS # 73229611)
    23
     
    181 Dyer St, Gardner, MA
    181 Dyer St
    Gardner, MA
    • 3 Beds
    • 1 Bath
    • 960 Home (sqft)
    • 1 Bath
    • 12,633 Lot (sqft)
    Listed with Keller Williams Realty North Central
  24. Photo of 30 Orono Street, Worcester, MA 01606 (MLS # 73229612)
    $299,900
    Photo of 30 Orono Street, Worcester, MA 01606 (MLS # 73229612)
    Photo of 30 Orono Street, Worcester, MA 01606 (MLS # 73229612)
    33
     
    30 Orono Street, Worcester, MA
    30 Orono Street
    Worcester, MA
    • 3 Beds
    • 2 Baths
    • 1,628 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
    Listed with RE/MAX Vision
  25. Photo of 209 Dunrobin Road, Mashpee, MA 02649 (MLS # 73229603)
    $1,150,000
    Photo of 209 Dunrobin Road, Mashpee, MA 02649 (MLS # 73229603)
    Photo of 209 Dunrobin Road, Mashpee, MA 02649 (MLS # 73229603)
    25
     
    209 Dunrobin Road, Mashpee, MA
    209 Dunrobin Road
    Mashpee, MA
    • 2 Beds
    • 3 Baths
    • 2,204 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Southworth Willowbend Real Estate, LLC
  26. Photo of 836 Cotuit Rd, Mashpee, MA 02649 (MLS # 73229598)
    $725,000
    Photo of 836 Cotuit Rd, Mashpee, MA 02649 (MLS # 73229598)
    Photo of 836 Cotuit Rd, Mashpee, MA 02649 (MLS # 73229598)
    42
     
    836 Cotuit Rd, Mashpee, MA
    836 Cotuit Rd
    Mashpee, MA
    • 3 Beds
    • 2 Baths
    • 1,937 Home (sqft)
    • 2 Baths
    • 2.07 Lot (ac)
    Listed with Kinlin Grover Compass
  27. Photo of 43 Stevenson Ln, Agawam, MA 01001 (MLS # 73229595)
    $890,000
    Photo of 43 Stevenson Ln, Agawam, MA 01001 (MLS # 73229595)
    Photo of 43 Stevenson Ln, Agawam, MA 01001 (MLS # 73229595)
    42
     
    43 Stevenson Ln, Agawam, MA
    43 Stevenson Ln
    Agawam, MA
    • 4 Beds
    • 4 Baths
    • 3,400 Home (sqft)
    • 4 Baths
    • 1.18 Lot (ac)
    Listed with RE/MAX Connections
  28. Photo of 173 East Main Street, Avon, MA 02322 (MLS # 73229591)
    $530,000
    Photo of 173 East Main Street, Avon, MA 02322 (MLS # 73229591)
    Photo of 173 East Main Street, Avon, MA 02322 (MLS # 73229591)
    13
     
    173 East Main Street, Avon, MA
    173 East Main Street
    Avon, MA
    • 4 Beds
    • 4 Baths
    • 2,926 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
    Listed with Better Living Real Estate, LLC
  29. Photo of 70 King Caesar Rd, Duxbury, MA 02332 (MLS # 73229590)
    $5,295,000
    Photo of 70 King Caesar Rd, Duxbury, MA 02332 (MLS # 73229590)
    Photo of 70 King Caesar Rd, Duxbury, MA 02332 (MLS # 73229590)
    28
     
    70 King Caesar Rd, Duxbury, MA
    70 King Caesar Rd
    Duxbury, MA
    • 4 Beds
    • 3 Baths
    • 3,186 Home (sqft)
    • 3 Baths
    • 1.02 Lot (ac)
    Listed with South Shore Sotheby's International Realty
  30. Photo of 9 Burnham Road, Wenham, MA 01984 (MLS # 73229588)
    $1,200,000
    Photo of 9 Burnham Road, Wenham, MA 01984 (MLS # 73229588)
    Photo of 9 Burnham Road, Wenham, MA 01984 (MLS # 73229588)
    9 Burnham Road, Wenham, MA
    9 Burnham Road
    Wenham, MA
    • 3 Beds
    • 3 Baths
    • 2,560 Home (sqft)
    • 3 Baths
    • 1.10 Lot (ac)
    Listed with J. Barrett & Company
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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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