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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 301 May Street, Worcester, MA 01602 (MLS # 73362377)
    $650,000
    Photo of 301 May Street, Worcester, MA 01602 (MLS # 73362377)
    Photo of 301 May Street, Worcester, MA 01602 (MLS # 73362377)
    18
     
    301 May Street, Worcester, MA
    301 May Street
    Worcester, MA
    • 4 Beds
    • 3 Baths
    • 1,719 Home (sqft)
    • 3 Baths
    • 19,602 Lot (sqft)
    Listed with ERA Key Realty Services- Spenc
  2. Photo of 37 Village Way #37, Holden, MA 01522 (MLS # 73362302)
    $399,900
    Photo of 37 Village Way #37, Holden, MA 01522 (MLS # 73362302)
    Photo of 37 Village Way #37, Holden, MA 01522 (MLS # 73362302)
    38
     
    37 Village Way #37, Holden, MA
    37 Village Way #37
    Holden, MA
    • 2 Beds
    • 3 Baths
    • 1,885 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Holden Realty Inc.
  3. Photo of 1 Joanne Dr, Marion, MA 02738 (MLS # 73362272)
    $649,900
    Photo of 1 Joanne Dr, Marion, MA 02738 (MLS # 73362272)
    Photo of 1 Joanne Dr, Marion, MA 02738 (MLS # 73362272)
    23
     
    1 Joanne Dr, Marion, MA
    1 Joanne Dr
    Marion, MA
    • 4 Beds
    • 2 Baths
    • 1,618 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
    Listed with Dawson Real Estate
  4. Photo of 242 Oak Street, Natick, MA 01760 (MLS # 73362252)
    $1,778,000
    Photo of 242 Oak Street, Natick, MA 01760 (MLS # 73362252)
    Photo of 242 Oak Street, Natick, MA 01760 (MLS # 73362252)
    42
     
    242 Oak Street, Natick, MA
    242 Oak Street
    Natick, MA
    • 5 Beds
    • 5 Baths
    • 4,546 Home (sqft)
    • 5 Baths
    • 12,633 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  5. Photo of 61 Meadow View Dr, Falmouth, MA 02536 (MLS # 73362251)
    $715,000
    Photo of 61 Meadow View Dr, Falmouth, MA 02536 (MLS # 73362251)
    Photo of 61 Meadow View Dr, Falmouth, MA 02536 (MLS # 73362251)
    42
     
    61 Meadow View Dr, Falmouth, MA
    61 Meadow View Dr
    Falmouth, MA
    • 3 Beds
    • 2 Baths
    • 1,676 Home (sqft)
    • 2 Baths
    • 15,246 Lot (sqft)
    Listed with Keller Williams Realty
  6. Photo of 22 Fitch Ter, Randolph, MA 02368 (MLS # 73362250)
    $750,000
    Photo of 22 Fitch Ter, Randolph, MA 02368 (MLS # 73362250)
    Photo of 22 Fitch Ter, Randolph, MA 02368 (MLS # 73362250)
    39
     
    22 Fitch Ter, Randolph, MA
    22 Fitch Ter
    Randolph, MA
    • 4 Beds
    • 3 Baths
    • 2,673 Home (sqft)
    • 3 Baths
    • 19,167 Lot (sqft)
    Listed with Keller Williams Realty
  7. Photo of 30 Highview Road, Rockport, MA 01966 (MLS # 73362249)
    $1,000,000
    Photo of 30 Highview Road, Rockport, MA 01966 (MLS # 73362249)
    Photo of 30 Highview Road, Rockport, MA 01966 (MLS # 73362249)
    33
     
    30 Highview Road, Rockport, MA
    30 Highview Road
    Rockport, MA
    • 3 Beds
    • 3 Baths
    • 2,128 Home (sqft)
    • 3 Baths
    • 37,462 Lot (sqft)
    Listed with Compass
  8. Photo of 183 Bass Point Rd, Nahant, MA 01908 (MLS # 73362247)
    $2,950,000
    Photo of 183 Bass Point Rd, Nahant, MA 01908 (MLS # 73362247)
    Photo of 183 Bass Point Rd, Nahant, MA 01908 (MLS # 73362247)
    33
     
    183 Bass Point Rd, Nahant, MA
    183 Bass Point Rd
    Nahant, MA
    • 4 Beds
    • 4 Baths
    • 3,295 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
    Listed with REAL ESTATE and Company
  9. Photo of 35 Tuckernuck Ave, Oak Bluffs, MA 02557 (MLS # 73362245)
    $1,895,000
    Photo of 35 Tuckernuck Ave, Oak Bluffs, MA 02557 (MLS # 73362245)
    Photo of 35 Tuckernuck Ave, Oak Bluffs, MA 02557 (MLS # 73362245)
    34
     
    35 Tuckernuck Ave, Oak Bluffs, MA
    35 Tuckernuck Ave
    Oak Bluffs, MA
    • 5 Beds
    • 2 Baths
    • 1,918 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
    Listed with Compass
  10. Photo of 21 John St, Worcester, MA 01609 (MLS # 73362242)
    $639,000
    Photo of 21 John St, Worcester, MA 01609 (MLS # 73362242)
    Photo of 21 John St, Worcester, MA 01609 (MLS # 73362242)
    20
     
    21 John St, Worcester, MA
    21 John St
    Worcester, MA
    • 6 Beds
    • 4 Baths
    • 2,663 Home (sqft)
    • 4 Baths
    • 4,792 Lot (sqft)
    Listed with Pondside Realty
  11. Photo of 3-5 Dean St, Stoneham, MA 02180 (MLS # 73362241)
    $870,000
    Photo of 3-5 Dean St, Stoneham, MA 02180 (MLS # 73362241)
    Photo of 3-5 Dean St, Stoneham, MA 02180 (MLS # 73362241)
    28
     
    3-5 Dean St, Stoneham, MA
    3-5 Dean St
    Stoneham, MA
    • 6 Beds
    • 3 Baths
    • 2,692 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
    Listed with Compass
  12. Photo of 40 Bonney Briar Dr, Plymouth, MA 02360 (MLS # 73362238)
    $550,000
    Photo of 40 Bonney Briar Dr, Plymouth, MA 02360 (MLS # 73362238)
    Photo of 40 Bonney Briar Dr, Plymouth, MA 02360 (MLS # 73362238)
    38
     
    40 Bonney Briar Dr, Plymouth, MA
    40 Bonney Briar Dr
    Plymouth, MA
    • 3 Beds
    • 2 Baths
    • 1,664 Home (sqft)
    • 2 Baths
    • 20,038 Lot (sqft)
    Listed with Conway - Mattapoisett
  13. Photo of 8 Mercer St #3, Boston, MA 02127 (MLS # 73362233)
    $1,280,000
    Photo of 8 Mercer St #3, Boston, MA 02127 (MLS # 73362233)
    Photo of 8 Mercer St #3, Boston, MA 02127 (MLS # 73362233)
    19
     
    8 Mercer St #3, Boston, MA
    8 Mercer St #3
    Boston, MA
    • 3 Beds
    • 2 Baths
    • 1,470 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Downtown Boston Realty
  14. Photo of 128 Franklin St, Haverhill, MA 01830 (MLS # 73362230)
    $689,000
    Photo of 128 Franklin St, Haverhill, MA 01830 (MLS # 73362230)
    Photo of 128 Franklin St, Haverhill, MA 01830 (MLS # 73362230)
    34
     
    128 Franklin St, Haverhill, MA
    128 Franklin St
    Haverhill, MA
    • 5 Beds
    • 2 Baths
    • 2,354 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
    Listed with Coldwell Banker Realty - Marblehead
  15. Photo of 5 Powissett St, Dover, MA 02030 (MLS # 73362220)
    $2,350,000
    Photo of 5 Powissett St, Dover, MA 02030 (MLS # 73362220)
    Photo of 5 Powissett St, Dover, MA 02030 (MLS # 73362220)
    40
     
    5 Powissett St, Dover, MA
    5 Powissett St
    Dover, MA
    • 4 Beds
    • 4 Baths
    • 4,848 Home (sqft)
    • 4 Baths
    • 2.00 Lot (ac)
    Listed with Compass
  16. Photo of 70 Upsala St, Worcester, MA 01610 (MLS # 73362199)
    $850,000
    Photo of 70 Upsala St, Worcester, MA 01610 (MLS # 73362199)
    Photo of 70 Upsala St, Worcester, MA 01610 (MLS # 73362199)
    40
     
    70 Upsala St, Worcester, MA
    70 Upsala St
    Worcester, MA
    • 8 Beds
    • 4 Baths
    • 2,672 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
    Listed with Murilo Silva
  17. Photo of 263 Woodbine Avenue, Hanson, MA 02341 (MLS # 73362226)
    $529,900
    Photo of 263 Woodbine Avenue, Hanson, MA 02341 (MLS # 73362226)
    Photo of 263 Woodbine Avenue, Hanson, MA 02341 (MLS # 73362226)
    34
     
    263 Woodbine Avenue, Hanson, MA
    263 Woodbine Avenue
    Hanson, MA
    • 3 Beds
    • 2 Baths
    • 1,794 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
    Listed with Keller Williams Realty
  18. Photo of 2 Wharf Road, Rockport, MA 01966 (MLS # 73362221)
    $1,395,000
    Photo of 2 Wharf Road, Rockport, MA 01966 (MLS # 73362221)
    Photo of 2 Wharf Road, Rockport, MA 01966 (MLS # 73362221)
    24
     
    2 Wharf Road, Rockport, MA
    2 Wharf Road
    Rockport, MA
    • 2 Beds
    • 2 Baths
    • 1,296 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
    Listed with Compass
  19. Photo of 324 Colonel Hunt Dr, Abington, MA 02351 (MLS # 73362204)
    $589,900
    Photo of 324 Colonel Hunt Dr, Abington, MA 02351 (MLS # 73362204)
    Photo of 324 Colonel Hunt Dr, Abington, MA 02351 (MLS # 73362204)
    39
     
    324 Colonel Hunt Dr, Abington, MA
    324 Colonel Hunt Dr
    Abington, MA
    • 3 Beds
    • 2 Baths
    • 1,492 Home (sqft)
    • 2 Baths
    • 21,345 Lot (sqft)
    Listed with HomeSmart First Class Realty
  20. Photo of 111 Daniel Shays Hwy #30, Belchertown, MA 01007 (MLS # 73362202)
    $450,000
    Photo of 111 Daniel Shays Hwy #30, Belchertown, MA 01007 (MLS # 73362202)
    Photo of 111 Daniel Shays Hwy #30, Belchertown, MA 01007 (MLS # 73362202)
    26
     
    111 Daniel Shays Hwy #30, Belchertown, MA
    111 Daniel Shays Hwy #30
    Belchertown, MA
    • 2 Beds
    • 2 Baths
    • 1,500 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with RE/MAX Compass
  21. Photo of 35 Waverly St #35, Brookline, MA 02445 (MLS # 73362190)
    $2,349,680
    Photo of 35 Waverly St #35, Brookline, MA 02445 (MLS # 73362190)
    Photo of 35 Waverly St #35, Brookline, MA 02445 (MLS # 73362190)
    32
     
    35 Waverly St #35, Brookline, MA
    35 Waverly St #35
    Brookline, MA
    • 4 Beds
    • 3 Baths
    • 2,782 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Dreamega International Realty LLC
  22. Photo of 34 Blake St, Revere, MA 02151 (MLS # 73362198)
    $425,000
    Photo of 34 Blake St, Revere, MA 02151 (MLS # 73362198)
    Photo of 34 Blake St, Revere, MA 02151 (MLS # 73362198)
    16
     
    34 Blake St, Revere, MA
    34 Blake St
    Revere, MA
    • 3 Beds
    • 1 Bath
    • 1,341 Home (sqft)
    • 1 Bath
    • 3,050 Lot (sqft)
    Listed with Harmony Hill Realty LLC
  23. Photo of 281 South St, Medfield, MA 02052 (MLS # 73362189)
    $999,000
    Photo of 281 South St, Medfield, MA 02052 (MLS # 73362189)
    Photo of 281 South St, Medfield, MA 02052 (MLS # 73362189)
    25
     
    281 South St, Medfield, MA
    281 South St
    Medfield, MA
    • 3 Beds
    • 3 Baths
    • 2,527 Home (sqft)
    • 3 Baths
    • 4.00 Lot (ac)
    Listed with William Raveis R.E. & Home Services
  24. Photo of 27 Willis St, Boston, MA 02125 (MLS # 73362187)
    $1,299,000
    Photo of 27 Willis St, Boston, MA 02125 (MLS # 73362187)
    Photo of 27 Willis St, Boston, MA 02125 (MLS # 73362187)
    24
     
    27 Willis St, Boston, MA
    27 Willis St
    Boston, MA
    • 6 Beds
    • 3 Baths
    • 3,960 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
    Listed with Compass
  25. Photo of 199 Winchester St #199, Brookline, MA 02446 (MLS # 73362227)
    $3,095,000
    Photo of 199 Winchester St #199, Brookline, MA 02446 (MLS # 73362227)
    Photo of 199 Winchester St #199, Brookline, MA 02446 (MLS # 73362227)
    26
     
    199 Winchester St #199, Brookline, MA
    199 Winchester St #199
    Brookline, MA
    • 4 Beds
    • 4 Baths
    • 2,696 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with RE/MAX On the Charles
  26. Photo of 50 Castle View Drive, Gloucester, MA 01930 (MLS # 73362222)
    $1,850,000
    Photo of 50 Castle View Drive, Gloucester, MA 01930 (MLS # 73362222)
    Photo of 50 Castle View Drive, Gloucester, MA 01930 (MLS # 73362222)
    39
     
    50 Castle View Drive, Gloucester, MA
    50 Castle View Drive
    Gloucester, MA
    • 4 Beds
    • 5 Baths
    • 4,292 Home (sqft)
    • 5 Baths
    • 20,038 Lot (sqft)
    Listed with Compass
  27. Photo of 50 Malibu Drive, Taunton, MA 02780 (MLS # 73362186)
    $765,000
    Photo of 50 Malibu Drive, Taunton, MA 02780 (MLS # 73362186)
    Photo of 50 Malibu Drive, Taunton, MA 02780 (MLS # 73362186)
    34
     
    50 Malibu Drive, Taunton, MA
    50 Malibu Drive
    Taunton, MA
    • 5 Beds
    • 3 Baths
    • 3,612 Home (sqft)
    • 3 Baths
    • 1.91 Lot (ac)
    Listed with F. J. Torres Insurance Agency
  28. Photo of 240 Devonshire Street #5006, Boston, MA 02110 (MLS # 73362225)
    $4,640,000
    Photo of 240 Devonshire Street #5006, Boston, MA 02110 (MLS # 73362225)
    Photo of 240 Devonshire Street #5006, Boston, MA 02110 (MLS # 73362225)
    40
     
    240 Devonshire Street #5006, Boston, MA
    240 Devonshire Street #5006
    Boston, MA
    • 2 Beds
    • 3 Baths
    • 1,755 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with MP Boston Marketing LLC
  29. Photo of 50 Thompson St, New Bedford, MA 02740 (MLS # 73362182)
    $569,900
    Photo of 50 Thompson St, New Bedford, MA 02740 (MLS # 73362182)
    Photo of 50 Thompson St, New Bedford, MA 02740 (MLS # 73362182)
    23
     
    50 Thompson St, New Bedford, MA
    50 Thompson St
    New Bedford, MA
    • 8 Beds
    • 3 Baths
    • 3,649 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
    Listed with ERA The Castelo Group
  30. Photo of 85 Cedar Street, Wellesley, MA 02481 (MLS # 73362180)
    $2,150,000
    Photo of 85 Cedar Street, Wellesley, MA 02481 (MLS # 73362180)
    Photo of 85 Cedar Street, Wellesley, MA 02481 (MLS # 73362180)
    85 Cedar Street, Wellesley, MA
    85 Cedar Street
    Wellesley, MA
    • 5 Beds
    • 5 Baths
    • 4,000 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
    Listed with Century 21 Shawmut Properties
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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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