Call Alexa: (781) 630-1704

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.

  • List View
  • Map View
  • Grid View

See all Real estate matching your search.
(all data current as of 6/18/2025)

Listing information deemed reliable but not guaranteed. Read full disclaimer.

 
 


Show Map
  • List View
  • Grid View
Sorted by
1 - 30 of 500+ | Previous Page 1 of 17 Next
  1. Photo of 34 Westminster Road, Newton, MA 02459 (MLS # 73392798)
    $1,549,000
    Photo of 34 Westminster Road, Newton, MA 02459 (MLS # 73392798)
    Photo of 34 Westminster Road, Newton, MA 02459 (MLS # 73392798)
    40
     
    34 Westminster Road, Newton, MA
    34 Westminster Road
    Newton, MA
    • 5 Beds
    • 3 Baths
    • 2,345 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  2. Photo of 13 Long Ridge Rd, Acton, MA 01720 (MLS # 73392801)
    $750,000
    Photo of 13 Long Ridge Rd, Acton, MA 01720 (MLS # 73392801)
    Photo of 13 Long Ridge Rd, Acton, MA 01720 (MLS # 73392801)
    41
     
    13 Long Ridge Rd, Acton, MA
    13 Long Ridge Rd
    Acton, MA
    • 3 Beds
    • 2 Baths
    • 2,144 Home (sqft)
    • 2 Baths
    • 1.83 Lot (ac)
    Listed with Keller Williams Realty Boston Northwest
  3. Photo of 439 South St #A, Plainville, MA 02762 (MLS # 73392796)
    $389,900
    Photo of 439 South St #A, Plainville, MA 02762 (MLS # 73392796)
    Photo of 439 South St #A, Plainville, MA 02762 (MLS # 73392796)
    35
     
    439 South St #A, Plainville, MA
    439 South St #A
    Plainville, MA
    • 2 Beds
    • 2 Baths
    • 1,350 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Evolution Properties
  4. Photo of 123 Walnut St, Saugus, MA 01906 (MLS # 73392799)
    $795,000
    Photo of 123 Walnut St, Saugus, MA 01906 (MLS # 73392799)
    Photo of 123 Walnut St, Saugus, MA 01906 (MLS # 73392799)
    42
     
    123 Walnut St, Saugus, MA
    123 Walnut St
    Saugus, MA
    • 3 Beds
    • 2 Baths
    • 2,234 Home (sqft)
    • 2 Baths
    • 15,682 Lot (sqft)
    Listed with Invest Realty Group
  5. Photo of 216 Cedar St #3, Somerville, MA 02144 (MLS # 73392792)
    $699,900
    Photo of 216 Cedar St #3, Somerville, MA 02144 (MLS # 73392792)
    Photo of 216 Cedar St #3, Somerville, MA 02144 (MLS # 73392792)
    38
     
    216 Cedar St #3, Somerville, MA
    216 Cedar St #3
    Somerville, MA
    • 2 Beds
    • 1 Bath
    • 1,008 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  6. Photo of 80 Vassar Road, Agawam, MA 01030 (MLS # 73392793)
    $425,000
    Photo of 80 Vassar Road, Agawam, MA 01030 (MLS # 73392793)
    Photo of 80 Vassar Road, Agawam, MA 01030 (MLS # 73392793)
    26
     
    80 Vassar Road, Agawam, MA
    80 Vassar Road
    Agawam, MA
    • 3 Beds
    • 2 Baths
    • 1,660 Home (sqft)
    • 2 Baths
    • 21,345 Lot (sqft)
    Listed with LPT Realty, LLC
  7. Photo of 17 Landers Rd, Quincy, MA 02170 (MLS # 73392795)
    $450,000
    Photo of 17 Landers Rd, Quincy, MA 02170 (MLS # 73392795)
    Photo of 17 Landers Rd, Quincy, MA 02170 (MLS # 73392795)
    34
     
    17 Landers Rd, Quincy, MA
    17 Landers Rd
    Quincy, MA
    • 2 Beds
    • 1 Bath
    • 660 Home (sqft)
    • 1 Bath
    • 2,178 Lot (sqft)
    Listed with East West Real Estate, LLC
  8. Photo of 61 Fiske Ave, Waltham, MA 02453 (MLS # 73392794)
    $899,000
    Photo of 61 Fiske Ave, Waltham, MA 02453 (MLS # 73392794)
    Photo of 61 Fiske Ave, Waltham, MA 02453 (MLS # 73392794)
    37
     
    61 Fiske Ave, Waltham, MA
    61 Fiske Ave
    Waltham, MA
    • 3 Beds
    • 2 Baths
    • 1,929 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
    Listed with EDGE Realty Advisors
  9. Photo of 43 Caddyshack Dr, Chicopee, MA 01020 (MLS # 73392790)
    $589,900
    Photo of 43 Caddyshack Dr, Chicopee, MA 01020 (MLS # 73392790)
    Photo of 43 Caddyshack Dr, Chicopee, MA 01020 (MLS # 73392790)
    30
     
    43 Caddyshack Dr, Chicopee, MA
    43 Caddyshack Dr
    Chicopee, MA
    • 3 Beds
    • 2 Baths
    • 2,735 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
    Listed with The Greene Realty Group
  10. Photo of 6 Mclean Parkway, Ludlow, MA 01056 (MLS # 73392788)
    $569,900
    Photo of 6 Mclean Parkway, Ludlow, MA 01056 (MLS # 73392788)
    Photo of 6 Mclean Parkway, Ludlow, MA 01056 (MLS # 73392788)
    37
     
    6 Mclean Parkway, Ludlow, MA
    6 Mclean Parkway
    Ludlow, MA
    • 5 Beds
    • 4 Baths
    • 2,550 Home (sqft)
    • 4 Baths
    • 22,652 Lot (sqft)
    Listed with The Real Estate Market Center
  11. Photo of 1056 Alger St, Winchendon, MA 01475 (MLS # 73392787)
    $414,900
    Photo of 1056 Alger St, Winchendon, MA 01475 (MLS # 73392787)
    Photo of 1056 Alger St, Winchendon, MA 01475 (MLS # 73392787)
    42
     
    1056 Alger St, Winchendon, MA
    1056 Alger St
    Winchendon, MA
    • 3 Beds
    • 2 Baths
    • 2,036 Home (sqft)
    • 2 Baths
    • 1.20 Lot (ac)
    Listed with RE/MAX American Dream
  12. Photo of 38 Kenmore Rd, Stoughton, MA 02072 (MLS # 73392775)
    $539,999
    Photo of 38 Kenmore Rd, Stoughton, MA 02072 (MLS # 73392775)
    Photo of 38 Kenmore Rd, Stoughton, MA 02072 (MLS # 73392775)
    42
     
    38 Kenmore Rd, Stoughton, MA
    38 Kenmore Rd
    Stoughton, MA
    • 3 Beds
    • 2 Baths
    • 1,854 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
    Listed with RE/MAX Platinum
  13. Photo of 37 Nachaomet Rd, Lakeville, MA 02347 (MLS # 73392777)
    $889,900
    Photo of 37 Nachaomet Rd, Lakeville, MA 02347 (MLS # 73392777)
    Photo of 37 Nachaomet Rd, Lakeville, MA 02347 (MLS # 73392777)
    42
     
    37 Nachaomet Rd, Lakeville, MA
    37 Nachaomet Rd
    Lakeville, MA
    • 4 Beds
    • 4 Baths
    • 3,826 Home (sqft)
    • 4 Baths
    • 2.03 Lot (ac)
    Listed with Century 21 North East
  14. Photo of 641 Pleasant St #1, Milton, MA 02186 (MLS # 73392783)
    $799,000
    Photo of 641 Pleasant St #1, Milton, MA 02186 (MLS # 73392783)
    Photo of 641 Pleasant St #1, Milton, MA 02186 (MLS # 73392783)
    641 Pleasant St #1, Milton, MA
    641 Pleasant St #1
    Milton, MA
    • 4 Beds
    • 2 Baths
    • 1,875 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  15. Photo of 117 Metropolitan Ave #117, Ashland, MA 01721 (MLS # 73392784)
    $400,000
    Photo of 117 Metropolitan Ave #117, Ashland, MA 01721 (MLS # 73392784)
    Photo of 117 Metropolitan Ave #117, Ashland, MA 01721 (MLS # 73392784)
    27
     
    117 Metropolitan Ave #117, Ashland, MA
    117 Metropolitan Ave #117
    Ashland, MA
    • 3 Beds
    • 3 Baths
    • 1,528 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Charney Real Estate
  16. Photo of 74 Parsons St, Easthampton, MA 01027 (MLS # 73392779)
    $279,000
    Photo of 74 Parsons St, Easthampton, MA 01027 (MLS # 73392779)
    Photo of 74 Parsons St, Easthampton, MA 01027 (MLS # 73392779)
    20
     
    74 Parsons St, Easthampton, MA
    74 Parsons St
    Easthampton, MA
    • 2 Beds
    • 1 Bath
    • 847 Home (sqft)
    • 1 Bath
    • 5,663 Lot (sqft)
    Listed with The Murphys REALTORS® , Inc.
  17. Photo of 27 N Brigham Hill Rd, Grafton, MA 01536 (MLS # 73392776)
    $795,000
    Photo of 27 N Brigham Hill Rd, Grafton, MA 01536 (MLS # 73392776)
    Photo of 27 N Brigham Hill Rd, Grafton, MA 01536 (MLS # 73392776)
    40
     
    27 N Brigham Hill Rd, Grafton, MA
    27 N Brigham Hill Rd
    Grafton, MA
    • 4 Beds
    • 4 Baths
    • 2,785 Home (sqft)
    • 4 Baths
    • 1.50 Lot (ac)
    Listed with Mathieu Newton Sotheby's International Realty
  18. Photo of 2 Maple Crest Cir #F, Holyoke, MA 01040 (MLS # 73392774)
    $194,900
    Photo of 2 Maple Crest Cir #F, Holyoke, MA 01040 (MLS # 73392774)
    Photo of 2 Maple Crest Cir #F, Holyoke, MA 01040 (MLS # 73392774)
    18
     
    2 Maple Crest Cir #F, Holyoke, MA
    2 Maple Crest Cir #F
    Holyoke, MA
    • 2 Beds
    • 1 Bath
    • 723 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Gallagher Real Estate
  19. Photo of 104 Bell Rock St, Malden, MA 02148 (MLS # 73392782)
    $499,900
    Photo of 104 Bell Rock St, Malden, MA 02148 (MLS # 73392782)
    Photo of 104 Bell Rock St, Malden, MA 02148 (MLS # 73392782)
    16
     
    104 Bell Rock St, Malden, MA
    104 Bell Rock St
    Malden, MA
    • 2 Beds
    • 1 Bath
    • 792 Home (sqft)
    • 1 Bath
    • 2,178 Lot (sqft)
    Listed with Duhallow Real Estate
  20. Photo of 28 Windsor St, Brockton, MA 02301 (MLS # 73392773)
    $444,900
    Photo of 28 Windsor St, Brockton, MA 02301 (MLS # 73392773)
    Photo of 28 Windsor St, Brockton, MA 02301 (MLS # 73392773)
    40
     
    28 Windsor St, Brockton, MA
    28 Windsor St
    Brockton, MA
    • 3 Beds
    • 1 Bath
    • 1,334 Home (sqft)
    • 1 Bath
    • 10,455 Lot (sqft)
    Listed with RE/MAX Platinum
  21. Photo of 34 Sumner St #34, Norfolk, MA 02056 (MLS # 73392771)
    $825,000
    Photo of 34 Sumner St #34, Norfolk, MA 02056 (MLS # 73392771)
    Photo of 34 Sumner St #34, Norfolk, MA 02056 (MLS # 73392771)
    31
     
    34 Sumner St #34, Norfolk, MA
    34 Sumner St #34
    Norfolk, MA
    • 3 Beds
    • 3 Baths
    • 1,860 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Westwood
  22. Photo of 10 Captain Eager Dr, Northborough, MA 01532 (MLS # 73392778)
    $649,000
    Photo of 10 Captain Eager Dr, Northborough, MA 01532 (MLS # 73392778)
    Photo of 10 Captain Eager Dr, Northborough, MA 01532 (MLS # 73392778)
    42
     
    10 Captain Eager Dr, Northborough, MA
    10 Captain Eager Dr
    Northborough, MA
    • 4 Beds
    • 2 Baths
    • 1,554 Home (sqft)
    • 2 Baths
    • 20,474 Lot (sqft)
    Listed with Keller Williams Pinnacle MetroWest
  23. Photo of 28 Farrwood Pl #28, Haverhill, MA 01835 (MLS # 73392780)
    $519,900
    Photo of 28 Farrwood Pl #28, Haverhill, MA 01835 (MLS # 73392780)
    Photo of 28 Farrwood Pl #28, Haverhill, MA 01835 (MLS # 73392780)
    28
     
    28 Farrwood Pl #28, Haverhill, MA
    28 Farrwood Pl #28
    Haverhill, MA
    • 3 Beds
    • 3 Baths
    • 2,184 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Lillian Montalto Signature Properties
  24. Photo of 240 Martins Lndg #207, North Reading, MA 01864 (MLS # 73392762)
    $714,900
    Photo of 240 Martins Lndg #207, North Reading, MA 01864 (MLS # 73392762)
    Photo of 240 Martins Lndg #207, North Reading, MA 01864 (MLS # 73392762)
    42
     
    240 Martins Lndg #207, North Reading, MA
    240 Martins Lndg #207
    North Reading, MA
    • 2 Beds
    • 2 Baths
    • 1,490 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Classified Realty Group
  25. Photo of 69 Kingman Ave, Revere, MA 02151 (MLS # 73392765)
    $779,999
    Photo of 69 Kingman Ave, Revere, MA 02151 (MLS # 73392765)
    Photo of 69 Kingman Ave, Revere, MA 02151 (MLS # 73392765)
    31
     
    69 Kingman Ave, Revere, MA
    69 Kingman Ave
    Revere, MA
    • 3 Beds
    • 2 Baths
    • 2,420 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
    Listed with Redfin Corp.
  26. Photo of 1856 Beacon St #2D, Brookline, MA 02445 (MLS # 73392763)
    $775,000
    Photo of 1856 Beacon St #2D, Brookline, MA 02445 (MLS # 73392763)
    Photo of 1856 Beacon St #2D, Brookline, MA 02445 (MLS # 73392763)
    16
     
    1856 Beacon St #2D, Brookline, MA
    1856 Beacon St #2D
    Brookline, MA
    • 2 Beds
    • 2 Baths
    • 913 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  27. Photo of 82 South Maple Street #44, Westfield, MA 01085 (MLS # 73392760)
    $189,900
    Photo of 82 South Maple Street #44, Westfield, MA 01085 (MLS # 73392760)
    Photo of 82 South Maple Street #44, Westfield, MA 01085 (MLS # 73392760)
    14
     
    82 South Maple Street #44, Westfield, MA
    82 South Maple Street #44
    Westfield, MA
    • 2 Beds
    • 1 Bath
    • 774 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Class Realty, Inc.
  28. Photo of 58 Gates St #One, Boston, MA 02127 (MLS # 73392752)
    $749,000
    Photo of 58 Gates St #One, Boston, MA 02127 (MLS # 73392752)
    Photo of 58 Gates St #One, Boston, MA 02127 (MLS # 73392752)
    15
     
    58 Gates St #One, Boston, MA
    58 Gates St #One
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,111 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  29. Photo of 6 Paddock Drive, Harwich, MA 02645 (MLS # 73392761)
    $690,000
    Photo of 6 Paddock Drive, Harwich, MA 02645 (MLS # 73392761)
    Photo of 6 Paddock Drive, Harwich, MA 02645 (MLS # 73392761)
    40
     
    6 Paddock Drive, Harwich, MA
    6 Paddock Drive
    Harwich, MA
    • 2 Beds
    • 2 Baths
    • 1,556 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
    Listed with Keller Williams Realty
  30. Photo of 11 Quincy Ave, Norwood, MA 02062 (MLS # 73392769)
    $630,000
    Photo of 11 Quincy Ave, Norwood, MA 02062 (MLS # 73392769)
    Photo of 11 Quincy Ave, Norwood, MA 02062 (MLS # 73392769)
    13
     
    11 Quincy Ave, Norwood, MA
    11 Quincy Ave
    Norwood, MA
    • 5 Beds
    • 2 Baths
    • 1,893 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
    Listed with Realty Executives Boston West
Previous Page 1 of 17 Next

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

This IDX Software is (c) Diverse Solutions 2025. Privacy | Terms & Conditions

 
 

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.

Contact Alexa

Alexa Dealy, Realtor® RE/MAX Andrew Realty Services Hours: 9:00 am – 7:00 pm

Compare listings

Compare
Call Now Button