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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 136 Munn Rd, Monson, MA 01057 (MLS # 73361886)
    $579,000
    Photo of 136 Munn Rd, Monson, MA 01057 (MLS # 73361886)
    Photo of 136 Munn Rd, Monson, MA 01057 (MLS # 73361886)
    11
     
    136 Munn Rd, Monson, MA
    136 Munn Rd
    Monson, MA
    • 3 Beds
    • 2 Baths
    • 2,000 Home (sqft)
    • 2 Baths
    • 2.19 Lot (ac)
    Listed with Stuart St James, Inc.
  2. Photo of 54 Bromfield St, Watertown, MA 02472 (MLS # 73361888)
    $719,000
    Photo of 54 Bromfield St, Watertown, MA 02472 (MLS # 73361888)
    Photo of 54 Bromfield St, Watertown, MA 02472 (MLS # 73361888)
    17
     
    54 Bromfield St, Watertown, MA
    54 Bromfield St
    Watertown, MA
    • 2 Beds
    • 1 Bath
    • 1,603 Home (sqft)
    • 1 Bath
    • 3,921 Lot (sqft)
    Listed with Coldwell Banker Realty - Belmont
  3. Photo of 30 Susan Lane, Middleboro, MA 02346 (MLS # 73361887)
    $559,900
    Photo of 30 Susan Lane, Middleboro, MA 02346 (MLS # 73361887)
    Photo of 30 Susan Lane, Middleboro, MA 02346 (MLS # 73361887)
    30
     
    30 Susan Lane, Middleboro, MA
    30 Susan Lane
    Middleboro, MA
    • 3 Beds
    • 2 Baths
    • 1,583 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
    Listed with Realty One Group, LLC
  4. Photo of 3 Estrella Lane, Falmouth, MA 02536 (MLS # 73361885)
    $950,000
    Photo of 3 Estrella Lane, Falmouth, MA 02536 (MLS # 73361885)
    Photo of 3 Estrella Lane, Falmouth, MA 02536 (MLS # 73361885)
    40
     
    3 Estrella Lane, Falmouth, MA
    3 Estrella Lane
    Falmouth, MA
    • 4 Beds
    • 3 Baths
    • 2,396 Home (sqft)
    • 3 Baths
    • 20,038 Lot (sqft)
    Listed with Salt Pond Realty, LLP
  5. Photo of 232 W Newton St #D, Boston, MA 02116 (MLS # 73361880)
    $759,000
    Photo of 232 W Newton St #D, Boston, MA 02116 (MLS # 73361880)
    Photo of 232 W Newton St #D, Boston, MA 02116 (MLS # 73361880)
    27
     
    232 W Newton St #D, Boston, MA
    232 W Newton St #D
    Boston, MA
    • 1 Bed
    • 1 Bath
    • 635 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Compass
  6. Photo of 5 Oakridge Ave, Natick, MA 01760 (MLS # 73361879)
    $1,899,999
    Photo of 5 Oakridge Ave, Natick, MA 01760 (MLS # 73361879)
    Photo of 5 Oakridge Ave, Natick, MA 01760 (MLS # 73361879)
    5 Oakridge Ave, Natick, MA
    5 Oakridge Ave
    Natick, MA
    • 5 Beds
    • 4 Baths
    • 4,133 Home (sqft)
    • 4 Baths
    • 10,455 Lot (sqft)
    Listed with Barber Real Estate
  7. Photo of 76 Thelma Way #76, Scituate, MA 02066 (MLS # 73361875)
    $1,480,000
    Photo of 76 Thelma Way #76, Scituate, MA 02066 (MLS # 73361875)
    Photo of 76 Thelma Way #76, Scituate, MA 02066 (MLS # 73361875)
    40
     
    76 Thelma Way #76, Scituate, MA
    76 Thelma Way #76
    Scituate, MA
    • 2 Beds
    • 3 Baths
    • 2,389 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Conway - Hull
  8. Photo of 111 & 112 Maple Way, East Brookfield, MA 01515 (MLS # 73361878)
    $874,900
    Photo of 111 & 112 Maple Way, East Brookfield, MA 01515 (MLS # 73361878)
    Photo of 111 & 112 Maple Way, East Brookfield, MA 01515 (MLS # 73361878)
    42
     
    111 & 112 Maple Way, East Brookfield, MA
    111 & 112 Maple Way
    East Brookfield, MA
    • 3 Beds
    • 3 Baths
    • 1,780 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
    Listed with ERA Key Realty Services- Spenc
  9. Photo of 11 Fox Hill Rd, Nahant, MA 01908 (MLS # 73361877)
    $995,000
    Photo of 11 Fox Hill Rd, Nahant, MA 01908 (MLS # 73361877)
    Photo of 11 Fox Hill Rd, Nahant, MA 01908 (MLS # 73361877)
    31
     
    11 Fox Hill Rd, Nahant, MA
    11 Fox Hill Rd
    Nahant, MA
    • 4 Beds
    • 2 Baths
    • 2,364 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Marblehead
  10. Photo of 19 Till Rock Ln, Norwell, MA 02061 (MLS # 73361873)
    $1,250,000
    Photo of 19 Till Rock Ln, Norwell, MA 02061 (MLS # 73361873)
    Photo of 19 Till Rock Ln, Norwell, MA 02061 (MLS # 73361873)
    40
     
    19 Till Rock Ln, Norwell, MA
    19 Till Rock Ln
    Norwell, MA
    • 4 Beds
    • 4 Baths
    • 3,285 Home (sqft)
    • 4 Baths
    • 43,560 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  11. Photo of 46 Sandwich Road #11, Plymouth, MA 02360 (MLS # 73361869)
    $1,054,000
    Photo of 46 Sandwich Road #11, Plymouth, MA 02360 (MLS # 73361869)
    Photo of 46 Sandwich Road #11, Plymouth, MA 02360 (MLS # 73361869)
    40
     
    46 Sandwich Road #11, Plymouth, MA
    46 Sandwich Road #11
    Plymouth, MA
    • 2 Beds
    • 3 Baths
    • 2,667 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Plymouth
  12. Photo of 178 Brook St, New Bedford, MA 02746 (MLS # 73361868)
    $480,000
    Photo of 178 Brook St, New Bedford, MA 02746 (MLS # 73361868)
    Photo of 178 Brook St, New Bedford, MA 02746 (MLS # 73361868)
    18
     
    178 Brook St, New Bedford, MA
    178 Brook St
    New Bedford, MA
    • 4 Beds
    • 2 Baths
    • 1,680 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
    Listed with RE/MAX Vantage
  13. Photo of 29 River St, Brookfield, MA 01506 (MLS # 73361865)
    $344,777
    Photo of 29 River St, Brookfield, MA 01506 (MLS # 73361865)
    Photo of 29 River St, Brookfield, MA 01506 (MLS # 73361865)
    18
     
    29 River St, Brookfield, MA
    29 River St
    Brookfield, MA
    • 4 Beds
    • 2 Baths
    • 1,616 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
    Listed with Property Partners Real Estate LLC
  14. Photo of 22 Harborwood Drive, Franklin, MA 02038 (MLS # 73361861)
    $875,000
    Photo of 22 Harborwood Drive, Franklin, MA 02038 (MLS # 73361861)
    Photo of 22 Harborwood Drive, Franklin, MA 02038 (MLS # 73361861)
    42
     
    22 Harborwood Drive, Franklin, MA
    22 Harborwood Drive
    Franklin, MA
    • 4 Beds
    • 3 Baths
    • 2,757 Home (sqft)
    • 3 Baths
    • 31,799 Lot (sqft)
    Listed with RE/MAX Real Estate Center
  15. Photo of 315 Front St, Chicopee, MA 01013 (MLS # 73361862)
    $395,000
    Photo of 315 Front St, Chicopee, MA 01013 (MLS # 73361862)
    Photo of 315 Front St, Chicopee, MA 01013 (MLS # 73361862)
    24
     
    315 Front St, Chicopee, MA
    315 Front St
    Chicopee, MA
    • 5 Beds
    • 3 Baths
    • 2,656 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
    Listed with Coldwell Banker Realty - Western MA
  16. Photo of 63 High St, Shrewsbury, MA 01545 (MLS # 73361859)
    $1,395,000
    Photo of 63 High St, Shrewsbury, MA 01545 (MLS # 73361859)
    Photo of 63 High St, Shrewsbury, MA 01545 (MLS # 73361859)
    40
     
    63 High St, Shrewsbury, MA
    63 High St
    Shrewsbury, MA
    • 4 Beds
    • 4 Baths
    • 4,566 Home (sqft)
    • 4 Baths
    • 36,591 Lot (sqft)
    Listed with Coldwell Banker Realty - Sudbury
  17. Photo of 145 N Washington St #10, Norton, MA 02766 (MLS # 73361860)
    $439,900
    Photo of 145 N Washington St #10, Norton, MA 02766 (MLS # 73361860)
    Photo of 145 N Washington St #10, Norton, MA 02766 (MLS # 73361860)
    35
     
    145 N Washington St #10, Norton, MA
    145 N Washington St #10
    Norton, MA
    • 2 Beds
    • 2 Baths
    • 1,485 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with RE/MAX Vantage
  18. Photo of 35 Oreo Lane, Barnstable, MA 02632 (MLS # 73361856)
    $719,000
    Photo of 35 Oreo Lane, Barnstable, MA 02632 (MLS # 73361856)
    Photo of 35 Oreo Lane, Barnstable, MA 02632 (MLS # 73361856)
    40
     
    35 Oreo Lane, Barnstable, MA
    35 Oreo Lane
    Barnstable, MA
    • 3 Beds
    • 2 Baths
    • 1,400 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
    Listed with Property Cape Cod
  19. Photo of 16 Pinewood Dr, Stratham, NH 03885 (MLS # 73361855)
    $824,900
    Photo of 16 Pinewood Dr, Stratham, NH 03885 (MLS # 73361855)
    Photo of 16 Pinewood Dr, Stratham, NH 03885 (MLS # 73361855)
    42
     
    16 Pinewood Dr, Stratham, NH
    16 Pinewood Dr
    Stratham, NH
    • 4 Beds
    • 4 Baths
    • 3,277 Home (sqft)
    • 4 Baths
    • 1.72 Lot (ac)
    Listed with Heather Klosowski Real Estate
  20. Photo of 129 Marshall St, Tewksbury, MA 01876 (MLS # 73361854)
    $899,000
    Photo of 129 Marshall St, Tewksbury, MA 01876 (MLS # 73361854)
    Photo of 129 Marshall St, Tewksbury, MA 01876 (MLS # 73361854)
    31
     
    129 Marshall St, Tewksbury, MA
    129 Marshall St
    Tewksbury, MA
    • 3 Beds
    • 4 Baths
    • 2,280 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
    Listed with Highlandview Realty
  21. Photo of 10 Shipyard Drive #402, Hingham, MA 02043 (MLS # 73361852)
    $1,249,000
    Photo of 10 Shipyard Drive #402, Hingham, MA 02043 (MLS # 73361852)
    Photo of 10 Shipyard Drive #402, Hingham, MA 02043 (MLS # 73361852)
    25
     
    10 Shipyard Drive #402, Hingham, MA
    10 Shipyard Drive #402
    Hingham, MA
    • 2 Beds
    • 3 Baths
    • 1,645 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Compass
  22. Photo of 713 Ocean Blvd, Hampton, NH 03842 (MLS # 73361853)
    $1,200,000
    Photo of 713 Ocean Blvd, Hampton, NH 03842 (MLS # 73361853)
    Photo of 713 Ocean Blvd, Hampton, NH 03842 (MLS # 73361853)
    713 Ocean Blvd, Hampton, NH
    713 Ocean Blvd
    Hampton, NH
    • 3 Beds
    • 2 Baths
    • 1,296 Home (sqft)
    • 2 Baths
    • 2,614 Lot (sqft)
    Listed with Keller Williams Coastal and Lakes & Mountains Realty
  23. Photo of 287 Taunton St, Wrentham, MA 02093 (MLS # 73361848)
    $695,000
    Photo of 287 Taunton St, Wrentham, MA 02093 (MLS # 73361848)
    Photo of 287 Taunton St, Wrentham, MA 02093 (MLS # 73361848)
    42
     
    287 Taunton St, Wrentham, MA
    287 Taunton St
    Wrentham, MA
    • 2 Beds
    • 2 Baths
    • 1,431 Home (sqft)
    • 2 Baths
    • 43,560 Lot (sqft)
    Listed with eXp Realty
  24. Photo of 2 Amvet Dr #B, Plainville, MA 02762 (MLS # 73361849)
    $419,000
    Photo of 2 Amvet Dr #B, Plainville, MA 02762 (MLS # 73361849)
    Photo of 2 Amvet Dr #B, Plainville, MA 02762 (MLS # 73361849)
    36
     
    2 Amvet Dr #B, Plainville, MA
    2 Amvet Dr #B
    Plainville, MA
    • 2 Beds
    • 2 Baths
    • 1,431 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with RE/MAX Host of Homes
  25. Photo of 105 - 107 Pine Grove Street, New Bedford, MA 02745 (MLS # 73361850)
    $575,000
    Photo of 105 - 107 Pine Grove Street, New Bedford, MA 02745 (MLS # 73361850)
    Photo of 105 - 107 Pine Grove Street, New Bedford, MA 02745 (MLS # 73361850)
    42
     
    105 - 107 Pine Grove Street, New Bedford, MA
    105 - 107 Pine Grove Street
    New Bedford, MA
    • 5 Beds
    • 2 Baths
    • 2,126 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
    Listed with Keller Williams South Watuppa
  26. Photo of 10 Keeney Pond Rd, Norfolk, MA 02056 (MLS # 73361847)
    $3,200,000
    Photo of 10 Keeney Pond Rd, Norfolk, MA 02056 (MLS # 73361847)
    Photo of 10 Keeney Pond Rd, Norfolk, MA 02056 (MLS # 73361847)
    10 Keeney Pond Rd, Norfolk, MA
    10 Keeney Pond Rd
    Norfolk, MA
    • 5 Beds
    • 5 Baths
    • 5,400 Home (sqft)
    • 5 Baths
    • 1.15 Lot (ac)
    Listed with Professional Properties
  27. Photo of 120 Mosier St, South Hadley, MA 01075 (MLS # 73361846)
    $400,000
    Photo of 120 Mosier St, South Hadley, MA 01075 (MLS # 73361846)
    Photo of 120 Mosier St, South Hadley, MA 01075 (MLS # 73361846)
    42
     
    120 Mosier St, South Hadley, MA
    120 Mosier St
    South Hadley, MA
    • 3 Beds
    • 1 Bath
    • 1,824 Home (sqft)
    • 1 Bath
    • 41,818 Lot (sqft)
    Listed with eXp Realty
  28. Photo of 11 Patriots Way, Southwick, MA 01077 (MLS # 73361845)
    $535,000
    Photo of 11 Patriots Way, Southwick, MA 01077 (MLS # 73361845)
    Photo of 11 Patriots Way, Southwick, MA 01077 (MLS # 73361845)
    40
     
    11 Patriots Way, Southwick, MA
    11 Patriots Way
    Southwick, MA
    • 4 Beds
    • 3 Baths
    • 2,291 Home (sqft)
    • 3 Baths
    • 30,928 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Realty Professionals
  29. Photo of 24-26 Oak St #24-1, Cambridge, MA 02139 (MLS # 73361844)
    $975,000
    Photo of 24-26 Oak St #24-1, Cambridge, MA 02139 (MLS # 73361844)
    Photo of 24-26 Oak St #24-1, Cambridge, MA 02139 (MLS # 73361844)
    25
     
    24-26 Oak St #24-1, Cambridge, MA
    24-26 Oak St #24-1
    Cambridge, MA
    • 3 Beds
    • 1 Bath
    • 1,136 Home (sqft)
    • 1 Bath
    • 7,841 Lot (sqft)
    Listed with Coldwell Banker Realty - Cambridge
  30. Photo of 32 Country Side Rd #32, Bellingham, MA 02019 (MLS # 73358095)
    $489,000
    Photo of 32 Country Side Rd #32, Bellingham, MA 02019 (MLS # 73358095)
    Photo of 32 Country Side Rd #32, Bellingham, MA 02019 (MLS # 73358095)
    29
     
    32 Country Side Rd #32, Bellingham, MA
    32 Country Side Rd #32
    Bellingham, MA
    • 2 Beds
    • 2 Baths
    • 2,234 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Costello 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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