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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 6/22/2025)

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  1. Photo of 9 Sydney St #2, Boston, MA 02125 (MLS # 73393967)
    $749,000
    Photo of 9 Sydney St #2, Boston, MA 02125 (MLS # 73393967)
    Photo of 9 Sydney St #2, Boston, MA 02125 (MLS # 73393967)
    9 Sydney St #2, Boston, MA
    9 Sydney St #2
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 879 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  2. Photo of 438 Granite Street, Worcester, MA 01604 (MLS # 73393965)
    $625,000
    Photo of 438 Granite Street, Worcester, MA 01604 (MLS # 73393965)
    Photo of 438 Granite Street, Worcester, MA 01604 (MLS # 73393965)
    33
     
    438 Granite Street, Worcester, MA
    438 Granite Street
    Worcester, MA
    • 3 Beds
    • 4 Baths
    • 2,548 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
    Listed with Keller Williams Realty Boston Northwest
  3. Photo of 14 Farrell Street, Newburyport, MA 01950 (MLS # 73393955)
    $715,000
    Photo of 14 Farrell Street, Newburyport, MA 01950 (MLS # 73393955)
    Photo of 14 Farrell Street, Newburyport, MA 01950 (MLS # 73393955)
    31
     
    14 Farrell Street, Newburyport, MA
    14 Farrell Street
    Newburyport, MA
    • 3 Beds
    • 1 Bath
    • 1,224 Home (sqft)
    • 1 Bath
    • 5,228 Lot (sqft)
    Listed with Churchill Properties
  4. Photo of 93 East Street, Upton, MA 01568 (MLS # 73393959)
    $1,100,000
    Photo of 93 East Street, Upton, MA 01568 (MLS # 73393959)
    Photo of 93 East Street, Upton, MA 01568 (MLS # 73393959)
    32
     
    93 East Street, Upton, MA
    93 East Street
    Upton, MA
    • 4 Beds
    • 3 Baths
    • 3,137 Home (sqft)
    • 3 Baths
    • 2.03 Lot (ac)
    Listed with Afonso Real Estate
  5. Photo of 48 Summer St, Adams, MA 01220 (MLS # 73393958)
    $174,500
    Photo of 48 Summer St, Adams, MA 01220 (MLS # 73393958)
    Photo of 48 Summer St, Adams, MA 01220 (MLS # 73393958)
    38
     
    48 Summer St, Adams, MA
    48 Summer St
    Adams, MA
    • 3 Beds
    • 1 Bath
    • 1,332 Home (sqft)
    • 1 Bath
    • 1,743 Lot (sqft)
    Listed with RE/MAX Diverse
  6. Photo of 12 Stratford Village Drive #12, Millbury, MA 01527 (MLS # 73393956)
    $539,900
    Photo of 12 Stratford Village Drive #12, Millbury, MA 01527 (MLS # 73393956)
    Photo of 12 Stratford Village Drive #12, Millbury, MA 01527 (MLS # 73393956)
    28
     
    12 Stratford Village Drive #12, Millbury, MA
    12 Stratford Village Drive #12
    Millbury, MA
    • 2 Beds
    • 3 Baths
    • 1,833 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Gibbs Realty Inc.
  7. Photo of 123 Sewall Ave #3C, Brookline, MA 02446 (MLS # 73393961)
    $499,900
    Photo of 123 Sewall Ave #3C, Brookline, MA 02446 (MLS # 73393961)
    Photo of 123 Sewall Ave #3C, Brookline, MA 02446 (MLS # 73393961)
    17
     
    123 Sewall Ave #3C, Brookline, MA
    123 Sewall Ave #3C
    Brookline, MA
    • 1 Bed
    • 1 Bath
    • 375 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with RE/MAX Real Estate Center
  8. Photo of 61 School Street Ext #B, Natick, MA 01760 (MLS # 73393960)
    $1,099,000
    Photo of 61 School Street Ext #B, Natick, MA 01760 (MLS # 73393960)
    Photo of 61 School Street Ext #B, Natick, MA 01760 (MLS # 73393960)
    41
     
    61 School Street Ext #B, Natick, MA
    61 School Street Ext #B
    Natick, MA
    • 3 Beds
    • 4 Baths
    • 3,000 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with Rufo Realty
  9. Photo of 4 Charlesgate E #106, Boston, MA 02215 (MLS # 73393962)
    $699,000
    Photo of 4 Charlesgate E #106, Boston, MA 02215 (MLS # 73393962)
    Photo of 4 Charlesgate E #106, Boston, MA 02215 (MLS # 73393962)
    12
     
    4 Charlesgate E #106, Boston, MA
    4 Charlesgate E #106
    Boston, MA
    • 1 Bed
    • 1 Bath
    • 637 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
    Listed with Compass
  10. Photo of 0 Oxbow Road #40-1, Raynham, MA 02767 (MLS # 73393948)
    $584,000
    Photo of 0 Oxbow Road #40-1, Raynham, MA 02767 (MLS # 73393948)
    Photo of 0 Oxbow Road #40-1, Raynham, MA 02767 (MLS # 73393948)
    23
     
    0 Oxbow Road #40-1, Raynham, MA
    0 Oxbow Road #40-1
    Raynham, MA
    • 2 Beds
    • 2 Baths
    • 1,671 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Thorndike Development
  11. Photo of 51 Carrie Ann Ln, Fitchburg, MA 01420 (MLS # 73393942)
    $515,000
    Photo of 51 Carrie Ann Ln, Fitchburg, MA 01420 (MLS # 73393942)
    Photo of 51 Carrie Ann Ln, Fitchburg, MA 01420 (MLS # 73393942)
    41
     
    51 Carrie Ann Ln, Fitchburg, MA
    51 Carrie Ann Ln
    Fitchburg, MA
    • 3 Beds
    • 3 Baths
    • 1,556 Home (sqft)
    • 3 Baths
    • 16,118 Lot (sqft)
    Listed with OPEN DOOR Real Estate
  12. Photo of 18 Myrick St, Ayer, MA 01432 (MLS # 73393951)
    $499,000
    Photo of 18 Myrick St, Ayer, MA 01432 (MLS # 73393951)
    Photo of 18 Myrick St, Ayer, MA 01432 (MLS # 73393951)
    18 Myrick St, Ayer, MA
    18 Myrick St
    Ayer, MA
    • 4 Beds
    • 1 Bath
    • 1,345 Home (sqft)
    • 1 Bath
    • 9,148 Lot (sqft)
    Listed with www.HomeZu.com
  13. Photo of 14 Mitchell St #1, Boston, MA 02127 (MLS # 73393945)
    $435,000
    Photo of 14 Mitchell St #1, Boston, MA 02127 (MLS # 73393945)
    Photo of 14 Mitchell St #1, Boston, MA 02127 (MLS # 73393945)
    12
     
    14 Mitchell St #1, Boston, MA
    14 Mitchell St #1
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 470 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Corcoran Property Advisors
  14. Photo of 205 Saint James Ave, Springfield, MA 01109 (MLS # 73393949)
    $140,000
    Photo of 205 Saint James Ave, Springfield, MA 01109 (MLS # 73393949)
    Photo of 205 Saint James Ave, Springfield, MA 01109 (MLS # 73393949)
    10
     
    205 Saint James Ave, Springfield, MA
    205 Saint James Ave
    Springfield, MA
    • 7 Beds
    • 2 Baths
    • 2,931 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
    Listed with United Brokers
  15. Photo of 3 Mark Rd, Beverly, MA 01915 (MLS # 73393947)
    $599,900
    Photo of 3 Mark Rd, Beverly, MA 01915 (MLS # 73393947)
    Photo of 3 Mark Rd, Beverly, MA 01915 (MLS # 73393947)
    17
     
    3 Mark Rd, Beverly, MA
    3 Mark Rd
    Beverly, MA
    • 3 Beds
    • 2 Baths
    • 1,018 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
    Listed with Keller Williams Realty Evolution
  16. Photo of 16 Foley Beach Rd, Hingham, MA 02043 (MLS # 73393943)
    $3,995,000
    Photo of 16 Foley Beach Rd, Hingham, MA 02043 (MLS # 73393943)
    Photo of 16 Foley Beach Rd, Hingham, MA 02043 (MLS # 73393943)
    30
     
    16 Foley Beach Rd, Hingham, MA
    16 Foley Beach Rd
    Hingham, MA
    • 4 Beds
    • 6 Baths
    • 5,529 Home (sqft)
    • 6 Baths
    • 13,504 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  17. Photo of 58 Berkeley Rd, North Andover, MA 01845 (MLS # 73393946)
    $1,080,000
    Photo of 58 Berkeley Rd, North Andover, MA 01845 (MLS # 73393946)
    Photo of 58 Berkeley Rd, North Andover, MA 01845 (MLS # 73393946)
    23
     
    58 Berkeley Rd, North Andover, MA
    58 Berkeley Rd
    North Andover, MA
    • 4 Beds
    • 3 Baths
    • 3,311 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
    Listed with Redfin Corp.
  18. Photo of 8 Auburn Rd, Beverly, MA 01915 (MLS # 73393950)
    $679,000
    Photo of 8 Auburn Rd, Beverly, MA 01915 (MLS # 73393950)
    Photo of 8 Auburn Rd, Beverly, MA 01915 (MLS # 73393950)
    35
     
    8 Auburn Rd, Beverly, MA
    8 Auburn Rd
    Beverly, MA
    • 3 Beds
    • 2 Baths
    • 1,794 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  19. Photo of 57 Summer Street, Medford, MA 02155 (MLS # 73393939)
    $949,900
    Photo of 57 Summer Street, Medford, MA 02155 (MLS # 73393939)
    Photo of 57 Summer Street, Medford, MA 02155 (MLS # 73393939)
    41
     
    57 Summer Street, Medford, MA
    57 Summer Street
    Medford, MA
    • 3 Beds
    • 2 Baths
    • 1,614 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
    Listed with Century 21 North East
  20. Photo of 21 Marsh St, Dedham, MA 02026 (MLS # 73393940)
    $1,195,000
    Photo of 21 Marsh St, Dedham, MA 02026 (MLS # 73393940)
    Photo of 21 Marsh St, Dedham, MA 02026 (MLS # 73393940)
    42
     
    21 Marsh St, Dedham, MA
    21 Marsh St
    Dedham, MA
    • 3 Beds
    • 3 Baths
    • 1,952 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
    Listed with Hope McDermott Real Estate
  21. Photo of 361 Walden St #361, Cambridge, MA 02138 (MLS # 73393936)
    $2,100,000
    Photo of 361 Walden St #361, Cambridge, MA 02138 (MLS # 73393936)
    Photo of 361 Walden St #361, Cambridge, MA 02138 (MLS # 73393936)
    37
     
    361 Walden St #361, Cambridge, MA
    361 Walden St #361
    Cambridge, MA
    • 3 Beds
    • 4 Baths
    • 2,400 Home (sqft)
    • 4 Baths
    • 2,614 Lot (sqft)
    Listed with Compass
  22. Photo of 112 Hunters Run Pl #112, Haverhill, MA 01832 (MLS # 73393935)
    $384,725
    Photo of 112 Hunters Run Pl #112, Haverhill, MA 01832 (MLS # 73393935)
    Photo of 112 Hunters Run Pl #112, Haverhill, MA 01832 (MLS # 73393935)
    22
     
    112 Hunters Run Pl #112, Haverhill, MA
    112 Hunters Run Pl #112
    Haverhill, MA
    • 2 Beds
    • 2 Baths
    • 1,110 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  23. Photo of 80 East St, Pepperell, MA 01463 (MLS # 73393934)
    $639,900
    Photo of 80 East St, Pepperell, MA 01463 (MLS # 73393934)
    Photo of 80 East St, Pepperell, MA 01463 (MLS # 73393934)
    39
     
    80 East St, Pepperell, MA
    80 East St
    Pepperell, MA
    • 4 Beds
    • 2 Baths
    • 2,566 Home (sqft)
    • 2 Baths
    • 2.12 Lot (ac)
    Listed with Keller Williams Gateway Realty
  24. Photo of 152 Stratford St, Boston, MA 02132 (MLS # 73393929)
    $899,000
    Photo of 152 Stratford St, Boston, MA 02132 (MLS # 73393929)
    Photo of 152 Stratford St, Boston, MA 02132 (MLS # 73393929)
    30
     
    152 Stratford St, Boston, MA
    152 Stratford St
    Boston, MA
    • 3 Beds
    • 2 Baths
    • 1,700 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
    Listed with Insight Realty Group, Inc.
  25. Photo of 2 Azalea Way, Boxford, MA 01921 (MLS # 73393926)
    $1,850,000
    Photo of 2 Azalea Way, Boxford, MA 01921 (MLS # 73393926)
    Photo of 2 Azalea Way, Boxford, MA 01921 (MLS # 73393926)
    42
     
    2 Azalea Way, Boxford, MA
    2 Azalea Way
    Boxford, MA
    • 5 Beds
    • 6 Baths
    • 4,490 Home (sqft)
    • 6 Baths
    • 2.01 Lot (ac)
    Listed with Lamacchia Realty, Inc.
  26. Photo of 110 Stuart Street #19D, Boston, MA 02116 (MLS # 73393932)
    $689,000
    Photo of 110 Stuart Street #19D, Boston, MA 02116 (MLS # 73393932)
    Photo of 110 Stuart Street #19D, Boston, MA 02116 (MLS # 73393932)
    20
     
    110 Stuart Street #19D, Boston, MA
    110 Stuart Street #19D
    Boston, MA
    • 0 Beds
    • 1 Bath
    • 427 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Back Bay Residential
  27. Photo of 251 Boylston St #251, Watertown, MA 02472 (MLS # 73393928)
    $1,235,000
    Photo of 251 Boylston St #251, Watertown, MA 02472 (MLS # 73393928)
    Photo of 251 Boylston St #251, Watertown, MA 02472 (MLS # 73393928)
    29
     
    251 Boylston St #251, Watertown, MA
    251 Boylston St #251
    Watertown, MA
    • 4 Beds
    • 3 Baths
    • 2,231 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Belmont
  28. Photo of 330 Thurston Street #330, Wrentham, MA 02093 (MLS # 73393930)
    $365,900
    Photo of 330 Thurston Street #330, Wrentham, MA 02093 (MLS # 73393930)
    Photo of 330 Thurston Street #330, Wrentham, MA 02093 (MLS # 73393930)
    41
     
    330 Thurston Street #330, Wrentham, MA
    330 Thurston Street #330
    Wrentham, MA
    • 2 Beds
    • 2 Baths
    • 1,080 Home (sqft)
    • 2 Baths
    • 1.60 Lot (ac)
    Listed with Berkshire Hathaway HomeServices Evolution Properties
  29. Photo of 38 Maplewood Ave, Holbrook, MA 02343 (MLS # 73393925)
    $599,900
    Photo of 38 Maplewood Ave, Holbrook, MA 02343 (MLS # 73393925)
    Photo of 38 Maplewood Ave, Holbrook, MA 02343 (MLS # 73393925)
    24
     
    38 Maplewood Ave, Holbrook, MA
    38 Maplewood Ave
    Holbrook, MA
    • 3 Beds
    • 2 Baths
    • 1,400 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  30. Photo of 24 Lantern Ln, Plymouth, MA 02360 (MLS # 73393917)
    $529,900
    Photo of 24 Lantern Ln, Plymouth, MA 02360 (MLS # 73393917)
    Photo of 24 Lantern Ln, Plymouth, MA 02360 (MLS # 73393917)
    28
     
    24 Lantern Ln, Plymouth, MA
    24 Lantern Ln
    Plymouth, MA
    • 3 Beds
    • 1 Bath
    • 1,509 Home (sqft)
    • 1 Bath
    • 13,940 Lot (sqft)
    Listed with ListWell
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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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