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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 37 Pemberton Rd, Wayland, MA 01778 (MLS # 73394014)
    $1,150,000
    Photo of 37 Pemberton Rd, Wayland, MA 01778 (MLS # 73394014)
    Photo of 37 Pemberton Rd, Wayland, MA 01778 (MLS # 73394014)
    34
     
    37 Pemberton Rd, Wayland, MA
    37 Pemberton Rd
    Wayland, MA
    • 4 Beds
    • 4 Baths
    • 2,709 Home (sqft)
    • 4 Baths
    • 27,443 Lot (sqft)
    Listed with Compass
  2. Photo of 170 Atlantic Avenue, Swampscott, MA 01907 (MLS # 73394010)
    $1,429,000
    Photo of 170 Atlantic Avenue, Swampscott, MA 01907 (MLS # 73394010)
    Photo of 170 Atlantic Avenue, Swampscott, MA 01907 (MLS # 73394010)
    42
     
    170 Atlantic Avenue, Swampscott, MA
    170 Atlantic Avenue
    Swampscott, MA
    • 4 Beds
    • 6 Baths
    • 4,182 Home (sqft)
    • 6 Baths
    • 12,633 Lot (sqft)
    Listed with Sagan Harborside Sotheby's International Realty
  3. Photo of 100 Ashland Street, Lynn, MA 01905 (MLS # 73394004)
    $629,000
    Photo of 100 Ashland Street, Lynn, MA 01905 (MLS # 73394004)
    Photo of 100 Ashland Street, Lynn, MA 01905 (MLS # 73394004)
    35
     
    100 Ashland Street, Lynn, MA
    100 Ashland Street
    Lynn, MA
    • 3 Beds
    • 2 Baths
    • 1,087 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
    Listed with Perlera Real Estate
  4. Photo of 19 Greenwich Park #5, Boston, MA 02118 (MLS # 73394003)
    $1,349,000
    Photo of 19 Greenwich Park #5, Boston, MA 02118 (MLS # 73394003)
    Photo of 19 Greenwich Park #5, Boston, MA 02118 (MLS # 73394003)
    32
     
    19 Greenwich Park #5, Boston, MA
    19 Greenwich Park #5
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 887 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
    Listed with Keller Williams Realty Boston-Metro | Back Bay
  5. Photo of 43 Kendall Avenue #G03, Sherborn, MA 01770 (MLS # 73394005)
    $545,000
    Photo of 43 Kendall Avenue #G03, Sherborn, MA 01770 (MLS # 73394005)
    Photo of 43 Kendall Avenue #G03, Sherborn, MA 01770 (MLS # 73394005)
    24
     
    43 Kendall Avenue #G03, Sherborn, MA
    43 Kendall Avenue #G03
    Sherborn, MA
    • 2 Beds
    • 2 Baths
    • 1,150 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  6. Photo of 37 Phillips Passway, Fitchburg, MA 01420 (MLS # 73394006)
    $425,000
    Photo of 37 Phillips Passway, Fitchburg, MA 01420 (MLS # 73394006)
    Photo of 37 Phillips Passway, Fitchburg, MA 01420 (MLS # 73394006)
    30
     
    37 Phillips Passway, Fitchburg, MA
    37 Phillips Passway
    Fitchburg, MA
    • 3 Beds
    • 2 Baths
    • 1,642 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  7. Photo of 162 Willow Rd #11, Nahant, MA 01908 (MLS # 73394000)
    $519,900
    Photo of 162 Willow Rd #11, Nahant, MA 01908 (MLS # 73394000)
    Photo of 162 Willow Rd #11, Nahant, MA 01908 (MLS # 73394000)
    28
     
    162 Willow Rd #11, Nahant, MA
    162 Willow Rd #11
    Nahant, MA
    • 1 Bed
    • 1 Bath
    • 721 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Toner Real Estate, LLC
  8. Photo of 17 Deforest Rd, Newton, MA 02462 (MLS # 73393996)
    $1,440,000
    Photo of 17 Deforest Rd, Newton, MA 02462 (MLS # 73393996)
    Photo of 17 Deforest Rd, Newton, MA 02462 (MLS # 73393996)
    36
     
    17 Deforest Rd, Newton, MA
    17 Deforest Rd
    Newton, MA
    • 3 Beds
    • 3 Baths
    • 2,035 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
    Listed with Natasha Amitan
  9. Photo of 37 High Street, Bradford, NH 03221 (MLS # 73393989)
    $1,499,900
    Photo of 37 High Street, Bradford, NH 03221 (MLS # 73393989)
    Photo of 37 High Street, Bradford, NH 03221 (MLS # 73393989)
    42
     
    37 High Street, Bradford, NH
    37 High Street
    Bradford, NH
    • 4 Beds
    • 4 Baths
    • 4,653 Home (sqft)
    • 4 Baths
    • 1.20 Lot (ac)
    Listed with Realty One Group Next Level
  10. Photo of 4 Fiske Avenue, Chelmsford, MA 01863 (MLS # 73393990)
    $589,900
    Photo of 4 Fiske Avenue, Chelmsford, MA 01863 (MLS # 73393990)
    Photo of 4 Fiske Avenue, Chelmsford, MA 01863 (MLS # 73393990)
    35
     
    4 Fiske Avenue, Chelmsford, MA
    4 Fiske Avenue
    Chelmsford, MA
    • 3 Beds
    • 2 Baths
    • 1,683 Home (sqft)
    • 2 Baths
    • 6,099 Lot (sqft)
    Listed with ERA Key Realty Services
  11. Photo of 7A Floral Avenue Extension, Natick, MA 01760 (MLS # 73393998)
    $1,698,000
    Photo of 7A Floral Avenue Extension, Natick, MA 01760 (MLS # 73393998)
    Photo of 7A Floral Avenue Extension, Natick, MA 01760 (MLS # 73393998)
    39
     
    7A Floral Avenue Extension, Natick, MA
    7A Floral Avenue Extension
    Natick, MA
    • 5 Beds
    • 5 Baths
    • 4,431 Home (sqft)
    • 5 Baths
    • 19,602 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  12. Photo of 31 Chittenden Ln #31, Cohasset, MA 02025 (MLS # 73393991)
    $1,800,000
    Photo of 31 Chittenden Ln #31, Cohasset, MA 02025 (MLS # 73393991)
    Photo of 31 Chittenden Ln #31, Cohasset, MA 02025 (MLS # 73393991)
    36
     
    31 Chittenden Ln #31, Cohasset, MA
    31 Chittenden Ln #31
    Cohasset, MA
    • 3 Beds
    • 5 Baths
    • 4,823 Home (sqft)
    • 5 Baths
    • 0 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  24. 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
  25. 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
  26. 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
  27. 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
  28. 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
  29. 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
  30. 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
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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.

Contact Alexa

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