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Winchester is a medium-sized town located in the state of Massachusetts. With a population of 22,799 people and five constituent neighborhoods, Winchester is the 90th largest community in Massachusetts.

Winchester home prices are not only among the most expensive in Massachusetts, but Winchester real estate also consistently ranks among the most expensive in America.

Winchester is a decidedly white-collar town, with fully 94.66% of the workforce employed in white-collar jobs, well above the national average. Overall, Winchester is a town of professionals, managers, and sales and office workers. There are especially a lot of people living in Winchester who work in management occupations (19.85%), business and financial occupations (11.83%), and sales jobs (10.72%).

Also of interest is that Winchester has more people living here who work in computers and math than 95% of the places in the US.

And if you like science, one thing you'll find is that Winchester has lots of scientists living in town - whether they be life scientists, physical scientists (like astronomers), or social scientists (like geographers!). So, if you're scientific-minded, you might like it here too.

In addition, Winchester is home to many people who could be described as "urban sophisticates". Urban sophisticates are educated, wealthy, executives and professionals, who have urbane tastes in books, food, and travel, whether they actually live in a big city, or choose to reside in a small town. In big or medium-sized cities, urban sophisticates tend to frequent art institutions such as opera, symphonies, ballet, live theatre, and museums.

Because of many things, Winchester is a great place for families with children to consider. First of all, many other families with children live here, making Winchester a place where both parents and children are more likely to develop social ties with other families, as well as find family-oriented services and community. The town’s good public school district and large population of college-educated adults provide an environment conducive to academic values. With regard to real estate, Winchester has a high rate of owner-occupied single family homes, which tends to reflect stability in the local community. Finally, Winchester’s overall crime rate ranks among the lowest in the country, making it one of the safest places to raise a family.

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(all data current as of 4/28/2024)

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  1. Photo of 118 Lingan St, Halifax, MA 02338 (MLS # 73225997)
    $400,000
    Photo of 118 Lingan St, Halifax, MA 02338 (MLS # 73225997)
    Photo of 118 Lingan St, Halifax, MA 02338 (MLS # 73225997)
    11
     
    118 Lingan St, Halifax, MA
    118 Lingan St
    Halifax, MA
    • 2 Beds
    • 1 Bath
    • 778 Home (sqft)
    • 1 Bath
    • 5,663 Lot (sqft)
    Listed with eXp Realty
  2. Photo of 65 Crystal St, Southbridge, MA 01550 (MLS # 73229698)
    $475,000
    Photo of 65 Crystal St, Southbridge, MA 01550 (MLS # 73229698)
    Photo of 65 Crystal St, Southbridge, MA 01550 (MLS # 73229698)
    65 Crystal St, Southbridge, MA
    65 Crystal St
    Southbridge, MA
    • 8 Beds
    • 4 Baths
    • 2,672 Home (sqft)
    • 4 Baths
    • 3,921 Lot (sqft)
    Listed with Coldwell Banker Realty - Brookline
  3. Photo of 29 Nome St, Worcester, MA 01605 (MLS # 73229696)
    $208,000
    Photo of 29 Nome St, Worcester, MA 01605 (MLS # 73229696)
    Photo of 29 Nome St, Worcester, MA 01605 (MLS # 73229696)
    12
     
    29 Nome St, Worcester, MA
    29 Nome St
    Worcester, MA
    • 4 Beds
    • 1 Bath
    • 960 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
    Listed with ERA Key Realty Services- Auburn
  4. Photo of 602 Durfee St, Fall River, MA 02720 (MLS # 73229690)
    $549,900
    Photo of 602 Durfee St, Fall River, MA 02720 (MLS # 73229690)
    Photo of 602 Durfee St, Fall River, MA 02720 (MLS # 73229690)
    602 Durfee St, Fall River, MA
    602 Durfee St
    Fall River, MA
    • 6 Beds
    • 3 Baths
    • 2,314 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
    Listed with Keller Williams South Watuppa
  5. Photo of 3 Centre Street, Natick, MA 01760 (MLS # 73229688)
    $899,000
    Photo of 3 Centre Street, Natick, MA 01760 (MLS # 73229688)
    Photo of 3 Centre Street, Natick, MA 01760 (MLS # 73229688)
    32
     
    3 Centre Street, Natick, MA
    3 Centre Street
    Natick, MA
    • 4 Beds
    • 2 Baths
    • 1,298 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  6. Photo of 236 Blossom Street, Fitchburg, MA 01420 (MLS # 73229687)
    $499,900
    Photo of 236 Blossom Street, Fitchburg, MA 01420 (MLS # 73229687)
    Photo of 236 Blossom Street, Fitchburg, MA 01420 (MLS # 73229687)
    35
     
    236 Blossom Street, Fitchburg, MA
    236 Blossom Street
    Fitchburg, MA
    • 4 Beds
    • 2 Baths
    • 2,334 Home (sqft)
    • 2 Baths
    • 18,731 Lot (sqft)
    Listed with April Dunn
  7. Photo of 27 Althea Road, Falmouth, MA 02556 (MLS # 73229684)
    $699,000
    Photo of 27 Althea Road, Falmouth, MA 02556 (MLS # 73229684)
    Photo of 27 Althea Road, Falmouth, MA 02556 (MLS # 73229684)
    30
     
    27 Althea Road, Falmouth, MA
    27 Althea Road
    Falmouth, MA
    • 4 Beds
    • 2 Baths
    • 1,704 Home (sqft)
    • 2 Baths
    • 20,038 Lot (sqft)
    Listed with Salt Pond Realty, LLP
  8. Photo of 222 Chippingstone Rd, Chatham, MA 02633 (MLS # 73229685)
    $999,950
    Photo of 222 Chippingstone Rd, Chatham, MA 02633 (MLS # 73229685)
    Photo of 222 Chippingstone Rd, Chatham, MA 02633 (MLS # 73229685)
    35
     
    222 Chippingstone Rd, Chatham, MA
    222 Chippingstone Rd
    Chatham, MA
    • 3 Beds
    • 3 Baths
    • 2,400 Home (sqft)
    • 3 Baths
    • 28,314 Lot (sqft)
    Listed with William Raveis Chatham
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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®
  18. 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
  19. 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
  20. 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.
  21. 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
  22. 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
    • 4 Beds
    • 3 Baths
    • 2,642 Home (sqft)
    • 3 Baths
    • 22,652 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  23. 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
  24. 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
  25. 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
  26. 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
  27. 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
  28. 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
  29. 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
  30. 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
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