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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 6/21/2025)

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  1. Photo of 4 Grove St, Medford, MA 02155 (MLS # 73393987)
    $1,995,000
    Photo of 4 Grove St, Medford, MA 02155 (MLS # 73393987)
    Photo of 4 Grove St, Medford, MA 02155 (MLS # 73393987)
    42
     
    4 Grove St, Medford, MA
    4 Grove St
    Medford, MA
    • 5 Beds
    • 5 Baths
    • 4,092 Home (sqft)
    • 5 Baths
    • 7,841 Lot (sqft)
    Listed with Advisors Living - Arlington
  2. Photo of 30 Cutter St #B, Melrose, MA 02176 (MLS # 73393993)
    $630,000
    Photo of 30 Cutter St #B, Melrose, MA 02176 (MLS # 73393993)
    Photo of 30 Cutter St #B, Melrose, MA 02176 (MLS # 73393993)
    24
     
    30 Cutter St #B, Melrose, MA
    30 Cutter St #B
    Melrose, MA
    • 3 Beds
    • 1 Bath
    • 1,242 Home (sqft)
    • 1 Bath
    • 9,148 Lot (sqft)
    Listed with Advisors Living - Arlington
  3. Photo of 6 Blackwell Dr, Charlton, MA 01507 (MLS # 73393988)
    $799,000
    Photo of 6 Blackwell Dr, Charlton, MA 01507 (MLS # 73393988)
    Photo of 6 Blackwell Dr, Charlton, MA 01507 (MLS # 73393988)
    42
     
    6 Blackwell Dr, Charlton, MA
    6 Blackwell Dr
    Charlton, MA
    • 4 Beds
    • 4 Baths
    • 4,248 Home (sqft)
    • 4 Baths
    • 2.10 Lot (ac)
    Listed with MA Homes, LLC
  4. Photo of 288 Fletcher Ln #288, Brewster, MA 02631 (MLS # 73393982)
    $499,000
    Photo of 288 Fletcher Ln #288, Brewster, MA 02631 (MLS # 73393982)
    Photo of 288 Fletcher Ln #288, Brewster, MA 02631 (MLS # 73393982)
    38
     
    288 Fletcher Ln #288, Brewster, MA
    288 Fletcher Ln #288
    Brewster, MA
    • 2 Beds
    • 2 Baths
    • 1,032 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Kinlin Grover Compass
  5. Photo of 719 S. Franklin Street #H Block 2, Holbrook, MA 02343 (MLS # 73393983)
    $499,900
    Photo of 719 S. Franklin Street #H Block 2, Holbrook, MA 02343 (MLS # 73393983)
    Photo of 719 S. Franklin Street #H Block 2, Holbrook, MA 02343 (MLS # 73393983)
    719 S. Franklin Street #H Block 2, Holbrook, MA
    719 S. Franklin Street #H Block 2
    Holbrook, MA
    • 2 Beds
    • 2 Baths
    • 1,240 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Realty
  6. Photo of 1 Ingalls Terrace, Lynnfield, MA 01940 (MLS # 73393981)
    $899,900
    Photo of 1 Ingalls Terrace, Lynnfield, MA 01940 (MLS # 73393981)
    Photo of 1 Ingalls Terrace, Lynnfield, MA 01940 (MLS # 73393981)
    1 Ingalls Terrace, Lynnfield, MA
    1 Ingalls Terrace
    Lynnfield, MA
    • 5 Beds
    • 3 Baths
    • 4,271 Home (sqft)
    • 3 Baths
    • 27,443 Lot (sqft)
    Listed with Real Broker MA, LLC
  7. Photo of 14 West Broadway #707, Boston, MA 02127 (MLS # 73393986)
    $1,649,000
    Photo of 14 West Broadway #707, Boston, MA 02127 (MLS # 73393986)
    Photo of 14 West Broadway #707, Boston, MA 02127 (MLS # 73393986)
    25
     
    14 West Broadway #707, Boston, MA
    14 West Broadway #707
    Boston, MA
    • 3 Beds
    • 3 Baths
    • 1,653 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  8. Photo of 166 Prides Crossing, Sudbury, MA 01776 (MLS # 73393979)
    $1,279,000
    Photo of 166 Prides Crossing, Sudbury, MA 01776 (MLS # 73393979)
    Photo of 166 Prides Crossing, Sudbury, MA 01776 (MLS # 73393979)
    36
     
    166 Prides Crossing, Sudbury, MA
    166 Prides Crossing
    Sudbury, MA
    • 4 Beds
    • 4 Baths
    • 4,954 Home (sqft)
    • 4 Baths
    • 5.00 Lot (ac)
    Listed with William Raveis R.E. & Home Services
  9. Photo of 7 Evergreen Cir, Sterling, MA 01564 (MLS # 73393984)
    $699,999
    Photo of 7 Evergreen Cir, Sterling, MA 01564 (MLS # 73393984)
    Photo of 7 Evergreen Cir, Sterling, MA 01564 (MLS # 73393984)
    41
     
    7 Evergreen Cir, Sterling, MA
    7 Evergreen Cir
    Sterling, MA
    • 4 Beds
    • 3 Baths
    • 2,669 Home (sqft)
    • 3 Baths
    • 3.00 Lot (ac)
    Listed with Keller Williams Realty North Central
  10. Photo of 7A Floral Ave. Ext #A, Natick, MA 01760 (MLS # 73393978)
    $1,698,000
    Photo of 7A Floral Ave. Ext #A, Natick, MA 01760 (MLS # 73393978)
    Photo of 7A Floral Ave. Ext #A, Natick, MA 01760 (MLS # 73393978)
    36
     
    7A Floral Ave. Ext #A, Natick, MA
    7A Floral Ave. Ext #A
    Natick, MA
    • 5 Beds
    • 5 Baths
    • 4,431 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  11. Photo of 72 Marlboro St, Dedham, MA 02026 (MLS # 73393972)
    $729,000
    Photo of 72 Marlboro St, Dedham, MA 02026 (MLS # 73393972)
    Photo of 72 Marlboro St, Dedham, MA 02026 (MLS # 73393972)
    22
     
    72 Marlboro St, Dedham, MA
    72 Marlboro St
    Dedham, MA
    • 3 Beds
    • 2 Baths
    • 1,656 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
    Listed with Keller Williams Realty
  12. Photo of 6 Magnolia Circle, Norfolk, MA 02056 (MLS # 73393976)
    $949,900
    Photo of 6 Magnolia Circle, Norfolk, MA 02056 (MLS # 73393976)
    Photo of 6 Magnolia Circle, Norfolk, MA 02056 (MLS # 73393976)
    42
     
    6 Magnolia Circle, Norfolk, MA
    6 Magnolia Circle
    Norfolk, MA
    • 4 Beds
    • 3 Baths
    • 3,161 Home (sqft)
    • 3 Baths
    • 1.49 Lot (ac)
    Listed with Berkshire Hathaway HomeServices Page Realty
  13. Photo of 2 Heron Way #B, Salisbury, MA 01952 (MLS # 73393975)
    $565,000
    Photo of 2 Heron Way #B, Salisbury, MA 01952 (MLS # 73393975)
    Photo of 2 Heron Way #B, Salisbury, MA 01952 (MLS # 73393975)
    27
     
    2 Heron Way #B, Salisbury, MA
    2 Heron Way #B
    Salisbury, MA
    • 2 Beds
    • 2 Baths
    • 1,567 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  14. Photo of 31 Fox Hollow, Plymouth, MA 02360 (MLS # 73393973)
    $743,000
    Photo of 31 Fox Hollow, Plymouth, MA 02360 (MLS # 73393973)
    Photo of 31 Fox Hollow, Plymouth, MA 02360 (MLS # 73393973)
    39
     
    31 Fox Hollow, Plymouth, MA
    31 Fox Hollow
    Plymouth, MA
    • 3 Beds
    • 3 Baths
    • 2,074 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
    Listed with Compass
  15. Photo of 54 Arlington St, Amesbury, MA 01913 (MLS # 73393974)
    $579,000
    Photo of 54 Arlington St, Amesbury, MA 01913 (MLS # 73393974)
    Photo of 54 Arlington St, Amesbury, MA 01913 (MLS # 73393974)
    38
     
    54 Arlington St, Amesbury, MA
    54 Arlington St
    Amesbury, MA
    • 3 Beds
    • 2 Baths
    • 1,444 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
    Listed with Aluxety
  16. Photo of 5 Cutler Rd, Paxton, MA 01612 (MLS # 73393964)
    $599,900
    Photo of 5 Cutler Rd, Paxton, MA 01612 (MLS # 73393964)
    Photo of 5 Cutler Rd, Paxton, MA 01612 (MLS # 73393964)
    34
     
    5 Cutler Rd, Paxton, MA
    5 Cutler Rd
    Paxton, MA
    • 3 Beds
    • 4 Baths
    • 2,489 Home (sqft)
    • 4 Baths
    • 19,602 Lot (sqft)
    Listed with Coldwell Banker Realty - Worcester
  17. Photo of 6 Windsor St, Andover, MA 01810 (MLS # 73393970)
    $1,300,000
    Photo of 6 Windsor St, Andover, MA 01810 (MLS # 73393970)
    Photo of 6 Windsor St, Andover, MA 01810 (MLS # 73393970)
    34
     
    6 Windsor St, Andover, MA
    6 Windsor St
    Andover, MA
    • 11 Beds
    • 4 Baths
    • 4,367 Home (sqft)
    • 4 Baths
    • 10,890 Lot (sqft)
    Listed with Keller Williams Realty Metropolitan
  18. Photo of 9-11 Kent #B, Newburyport, MA 01950 (MLS # 73393971)
    $379,000
    Photo of 9-11 Kent #B, Newburyport, MA 01950 (MLS # 73393971)
    Photo of 9-11 Kent #B, Newburyport, MA 01950 (MLS # 73393971)
    32
     
    9-11 Kent #B, Newburyport, MA
    9-11 Kent #B
    Newburyport, MA
    • 1 Bed
    • 1 Bath
    • 536 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Advisors Living - Merrimac
  19. Photo of Lot 4 Granite Street, Worcester, MA 01604 (MLS # 73393966)
    $625,000
    Photo of Lot 4 Granite Street, Worcester, MA 01604 (MLS # 73393966)
    Photo of Lot 4 Granite Street, Worcester, MA 01604 (MLS # 73393966)
    32
     
    Lot 4 Granite Street, Worcester, MA
    Lot 4 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
  20. Photo of 99 Elizabeth St, Agawam, MA 01030 (MLS # 73393968)
    $949,900
    Photo of 99 Elizabeth St, Agawam, MA 01030 (MLS # 73393968)
    Photo of 99 Elizabeth St, Agawam, MA 01030 (MLS # 73393968)
    33
     
    99 Elizabeth St, Agawam, MA
    99 Elizabeth St
    Agawam, MA
    • 3 Beds
    • 5 Baths
    • 2,947 Home (sqft)
    • 5 Baths
    • 40,076 Lot (sqft)
    Listed with Keller Williams Realty
  21. 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
  22. 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
  23. 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
  24. 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
  25. 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
  26. 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.
  27. 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
  28. 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
  29. 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
  30. 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
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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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