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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 12/13/2024)

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  1. No property photo available
    $419,900
    No property photo available
    No property photo available
    10 Great Cedar Drive #10, Hanson, MA
    10 Great Cedar Drive #10
    Hanson, MA
    • 2 Beds
    • 2 Baths
    • 1,381 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Real Broker MA, LLC
  2. No property photo available
    $459,900
    No property photo available
    No property photo available
    12 Williams St, Auburn, MA
    12 Williams St
    Auburn, MA
    • 3 Beds
    • 2 Baths
    • 1,350 Home (sqft)
    • 2 Baths
    • 31,364 Lot (sqft)
    Listed with Cali Realty Group, Inc.
  3. No property photo available
    $299,987
    No property photo available
    No property photo available
    23 Leonard Ave, Westfield, MA
    23 Leonard Ave
    Westfield, MA
    • 4 Beds
    • 2 Baths
    • 1,769 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
    Listed with Hampden Realty Center, LLC
  4. No property photo available
    $849,900
    No property photo available
    No property photo available
    70 Sumac Lane, North Attleboro, MA
    70 Sumac Lane
    North Attleboro, MA
    • 5 Beds
    • 3 Baths
    • 2,816 Home (sqft)
    • 3 Baths
    • 21,780 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Evolution Properties
  5. No property photo available
    $309,000
    No property photo available
    No property photo available
    300 Main Rd, Westhampton, MA
    300 Main Rd
    Westhampton, MA
    • 4 Beds
    • 1 Bath
    • 1,308 Home (sqft)
    • 1 Bath
    • 21,780 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  6. No property photo available
    $379,900
    No property photo available
    No property photo available
    1 Treetop Lane #2, Kingston, MA
    1 Treetop Lane #2
    Kingston, MA
    • 2 Beds
    • 2 Baths
    • 1,080 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Conway - Plymouth
  7. No property photo available
    $549,000
    No property photo available
    No property photo available
    27/29 Pearl Street, Middleboro, MA
    27/29 Pearl Street
    Middleboro, MA
    • 4 Beds
    • 2 Baths
    • 2,174 Home (sqft)
    • 2 Baths
    • 8,277 Lot (sqft)
    Listed with Bold Real Estate, Inc.
  8. Photo of 9 Olive Ter, Brockton, MA 02301 (MLS # 73319612)
    $779,777
    Photo of 9 Olive Ter, Brockton, MA 02301 (MLS # 73319612)
    Photo of 9 Olive Ter, Brockton, MA 02301 (MLS # 73319612)
    27
     
    9 Olive Ter, Brockton, MA
    9 Olive Ter
    Brockton, MA
    • 7 Beds
    • 2 Baths
    • 2,197 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
    Listed with Vicente Realty, LLC
  9. Photo of 7 Shaw St, Norwood, MA 02062 (MLS # 73319613)
    $1,299,000
    Photo of 7 Shaw St, Norwood, MA 02062 (MLS # 73319613)
    Photo of 7 Shaw St, Norwood, MA 02062 (MLS # 73319613)
    32
     
    7 Shaw St, Norwood, MA
    7 Shaw St
    Norwood, MA
    • 4 Beds
    • 3 Baths
    • 3,776 Home (sqft)
    • 3 Baths
    • 10,019 Lot (sqft)
    Listed with Irene Tan
  10. Photo of 22 Main St, Marshfield, MA 02050 (MLS # 73319607)
    $1,285,000
    Photo of 22 Main St, Marshfield, MA 02050 (MLS # 73319607)
    Photo of 22 Main St, Marshfield, MA 02050 (MLS # 73319607)
    39
     
    22 Main St, Marshfield, MA
    22 Main St
    Marshfield, MA
    • 4 Beds
    • 3 Baths
    • 4,576 Home (sqft)
    • 3 Baths
    • 18,731 Lot (sqft)
    Listed with The Sobran Group
  11. Photo of 69 Bogastow Brook Road, Sherborn, MA 01770 (MLS # 73319605)
    $1,850,000
    Photo of 69 Bogastow Brook Road, Sherborn, MA 01770 (MLS # 73319605)
    Photo of 69 Bogastow Brook Road, Sherborn, MA 01770 (MLS # 73319605)
    42
     
    69 Bogastow Brook Road, Sherborn, MA
    69 Bogastow Brook Road
    Sherborn, MA
    • 3 Beds
    • 3 Baths
    • 4,252 Home (sqft)
    • 3 Baths
    • 5.32 Lot (ac)
    Listed with Advisors Living - Sherborn
  12. No property photo available
    $325,000
    No property photo available
    No property photo available
    1100 Governors Dr #24, Winthrop, MA
    1100 Governors Dr #24
    Winthrop, MA
    • 2 Beds
    • 1 Bath
    • 782 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Engel & Volkers Boston
  13. No property photo available
    $399,900
    No property photo available
    No property photo available
    64 Acrebrook Rd, Springfield, MA
    64 Acrebrook Rd
    Springfield, MA
    • 4 Beds
    • 3 Baths
    • 2,425 Home (sqft)
    • 3 Baths
    • 18,731 Lot (sqft)
    Listed with ERA M Connie Laplante Real Estate
  14. No property photo available
    $569,000
    No property photo available
    No property photo available
    39 Cook St, Boylston, MA
    39 Cook St
    Boylston, MA
    • 2 Beds
    • 3 Baths
    • 1,950 Home (sqft)
    • 3 Baths
    • 1.02 Lot (ac)
    Listed with LAER Realty Partners
  15. No property photo available
    $499,900
    No property photo available
    No property photo available
    95 Copeland Street, Brockton, MA
    95 Copeland Street
    Brockton, MA
    • 4 Beds
    • 2 Baths
    • 1,862 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
    Listed with Success! Real Estate
  16. No property photo available
    $274,777
    No property photo available
    No property photo available
    42 Riverside Ave, Swansea, MA
    42 Riverside Ave
    Swansea, MA
    • 3 Beds
    • 3 Baths
    • 980 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
    Listed with Prestige Realty Experts Inc.
  17. No property photo available
    $1,799,900
    No property photo available
    No property photo available
    545 Winthrop St #Lot 3, Medford, MA
    545 Winthrop St #Lot 3
    Medford, MA
    • 4 Beds
    • 5 Baths
    • 3,700 Home (sqft)
    • 5 Baths
    • 7,841 Lot (sqft)
    Listed with EVO Real Estate Group, LLC
  18. No property photo available
    $724,900
    No property photo available
    No property photo available
    40 Montgomery St, Lawrence, MA
    40 Montgomery St
    Lawrence, MA
    • 6 Beds
    • 3 Baths
    • 2,990 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
    Listed with Century 21 North East
  19. No property photo available
    $439,900
    No property photo available
    No property photo available
    25 Jessica Way, Fitchburg, MA
    25 Jessica Way
    Fitchburg, MA
    • 2 Beds
    • 2 Baths
    • 1,138 Home (sqft)
    • 2 Baths
    • 22,216 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  20. Photo of 857 Blue Hill Ave, Boston, MA 02124 (MLS # 73319593)
    $900,000
    Photo of 857 Blue Hill Ave, Boston, MA 02124 (MLS # 73319593)
    Photo of 857 Blue Hill Ave, Boston, MA 02124 (MLS # 73319593)
    857 Blue Hill Ave, Boston, MA
    857 Blue Hill Ave
    Boston, MA
    • 6 Beds
    • 3 Baths
    • 3,231 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
    Listed with Maron Realty
  21. No property photo available
    $379,900
    No property photo available
    No property photo available
    21 Warren St, North Brookfield, MA
    21 Warren St
    North Brookfield, MA
    • 3 Beds
    • 2 Baths
    • 1,758 Home (sqft)
    • 2 Baths
    • 34,848 Lot (sqft)
    Listed with Coldwell Banker Realty - Leominster
  22. Photo of 17 Sunny Hill Drive, Worcester, MA 01602 (MLS # 73319592)
    $438,500
    Photo of 17 Sunny Hill Drive, Worcester, MA 01602 (MLS # 73319592)
    Photo of 17 Sunny Hill Drive, Worcester, MA 01602 (MLS # 73319592)
    23
     
    17 Sunny Hill Drive, Worcester, MA
    17 Sunny Hill Drive
    Worcester, MA
    • 3 Beds
    • 1 Bath
    • 1,429 Home (sqft)
    • 1 Bath
    • 7,841 Lot (sqft)
    Listed with Property Investors & Advisors, LLC
  23. No property photo available
    $1,850,000
    No property photo available
    No property photo available
    8 Julia Lane, Mansfield, MA
    8 Julia Lane
    Mansfield, MA
    • 4 Beds
    • 4 Baths
    • 3,909 Home (sqft)
    • 4 Baths
    • 1.89 Lot (ac)
    Listed with Gerry Abbott REALTORS®
  24. Photo of 280 Martins Landing #108, North Reading, MA 01864 (MLS # 73319578)
    $595,000
    Photo of 280 Martins Landing #108, North Reading, MA 01864 (MLS # 73319578)
    Photo of 280 Martins Landing #108, North Reading, MA 01864 (MLS # 73319578)
    18
     
    280 Martins Landing #108, North Reading, MA
    280 Martins Landing #108
    North Reading, MA
    • 1 Bed
    • 1 Bath
    • 1,129 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with J. Barrett & Company
  25. Photo of 15 Cedar St #32, Amesbury, MA 01913 (MLS # 73319584)
    $449,900
    Photo of 15 Cedar St #32, Amesbury, MA 01913 (MLS # 73319584)
    Photo of 15 Cedar St #32, Amesbury, MA 01913 (MLS # 73319584)
    37
     
    15 Cedar St #32, Amesbury, MA
    15 Cedar St #32
    Amesbury, MA
    • 2 Beds
    • 1 Bath
    • 1,043 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Century 21 North East
  26. Photo of 33 Forest Ridge Ln, Agawam, MA 01001 (MLS # 73319579)
    $449,900
    Photo of 33 Forest Ridge Ln, Agawam, MA 01001 (MLS # 73319579)
    Photo of 33 Forest Ridge Ln, Agawam, MA 01001 (MLS # 73319579)
    36
     
    33 Forest Ridge Ln, Agawam, MA
    33 Forest Ridge Ln
    Agawam, MA
    • 3 Beds
    • 3 Baths
    • 2,003 Home (sqft)
    • 3 Baths
    • 20,909 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Realty Professionals
  27. No property photo available
    $244,900
    No property photo available
    No property photo available
    668 Robbins Ave #2, Dracut, MA
    668 Robbins Ave #2
    Dracut, MA
    • 2 Beds
    • 1 Bath
    • 700 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Allison James Estates & Homes of MA, LLC
  28. Photo of 6 Stevens Terrace, Arlington, MA 02476 (MLS # 73319585)
    $1,299,000
    Photo of 6 Stevens Terrace, Arlington, MA 02476 (MLS # 73319585)
    Photo of 6 Stevens Terrace, Arlington, MA 02476 (MLS # 73319585)
    40
     
    6 Stevens Terrace, Arlington, MA
    6 Stevens Terrace
    Arlington, MA
    • 3 Beds
    • 2 Baths
    • 1,820 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  29. No property photo available
    $649,000
    No property photo available
    No property photo available
    6 Weldon St, Boston, MA
    6 Weldon St
    Boston, MA
    • 4 Beds
    • 3 Baths
    • 2,422 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
    Listed with Olde Towne Real Estate Co.
  30. Photo of 6-8-12 Weldon St, Boston, MA 02121 (MLS # 73319574)
    $734,000
    Photo of 6-8-12 Weldon St, Boston, MA 02121 (MLS # 73319574)
    Photo of 6-8-12 Weldon St, Boston, MA 02121 (MLS # 73319574)
    6-8-12 Weldon St, Boston, MA
    6-8-12 Weldon St
    Boston, MA
    • 4 Beds
    • 3 Baths
    • 2,422 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
    Listed with Olde Towne Real Estate Co.
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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.

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

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