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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 796 Foundry St, Easton, MA 02375 (MLS # 73394027)
    $785,000
    Photo of 796 Foundry St, Easton, MA 02375 (MLS # 73394027)
    Photo of 796 Foundry St, Easton, MA 02375 (MLS # 73394027)
    41
     
    796 Foundry St, Easton, MA
    796 Foundry St
    Easton, MA
    • 3 Beds
    • 3 Baths
    • 1,980 Home (sqft)
    • 3 Baths
    • 1.05 Lot (ac)
    Listed with RE/MAX Executive Realty
  2. Photo of 30 Ridgewood Ln, Quincy, MA 02169 (MLS # 73394026)
    $1,250,000
    Photo of 30 Ridgewood Ln, Quincy, MA 02169 (MLS # 73394026)
    Photo of 30 Ridgewood Ln, Quincy, MA 02169 (MLS # 73394026)
    29
     
    30 Ridgewood Ln, Quincy, MA
    30 Ridgewood Ln
    Quincy, MA
    • 4 Beds
    • 4 Baths
    • 2,335 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
    Listed with The Greene Realty Group
  3. Photo of 7 Sequoia Dr, Wilmington, MA 01887 (MLS # 73394033)
    $1,080,000
    Photo of 7 Sequoia Dr, Wilmington, MA 01887 (MLS # 73394033)
    Photo of 7 Sequoia Dr, Wilmington, MA 01887 (MLS # 73394033)
    42
     
    7 Sequoia Dr, Wilmington, MA
    7 Sequoia Dr
    Wilmington, MA
    • 4 Beds
    • 3 Baths
    • 2,669 Home (sqft)
    • 3 Baths
    • 24,830 Lot (sqft)
    Listed with NextHome Luxury Realty
  4. Photo of 36 Knowlton Cir #36, Upton, MA 01568 (MLS # 73394021)
    $575,000
    Photo of 36 Knowlton Cir #36, Upton, MA 01568 (MLS # 73394021)
    Photo of 36 Knowlton Cir #36, Upton, MA 01568 (MLS # 73394021)
    42
     
    36 Knowlton Cir #36, Upton, MA
    36 Knowlton Cir #36
    Upton, MA
    • 3 Beds
    • 3 Baths
    • 2,231 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with LAER Realty Partners
  5. Photo of 12 Rural Avenue, Medford, MA 02155 (MLS # 73394023)
    $889,000
    Photo of 12 Rural Avenue, Medford, MA 02155 (MLS # 73394023)
    Photo of 12 Rural Avenue, Medford, MA 02155 (MLS # 73394023)
    27
     
    12 Rural Avenue, Medford, MA
    12 Rural Avenue
    Medford, MA
    • 3 Beds
    • 2 Baths
    • 2,215 Home (sqft)
    • 2 Baths
    • 5,228 Lot (sqft)
    Listed with Meridian Realty Group LLC
  6. Photo of 37 Prospect St, Webster, MA 01570 (MLS # 73394022)
    $449,900
    Photo of 37 Prospect St, Webster, MA 01570 (MLS # 73394022)
    Photo of 37 Prospect St, Webster, MA 01570 (MLS # 73394022)
    17
     
    37 Prospect St, Webster, MA
    37 Prospect St
    Webster, MA
    • 8 Beds
    • 3 Baths
    • 2,904 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  7. Photo of 4 Deer Path #2, Maynard, MA 01754 (MLS # 73394017)
    $489,900
    Photo of 4 Deer Path #2, Maynard, MA 01754 (MLS # 73394017)
    Photo of 4 Deer Path #2, Maynard, MA 01754 (MLS # 73394017)
    34
     
    4 Deer Path #2, Maynard, MA
    4 Deer Path #2
    Maynard, MA
    • 2 Beds
    • 2 Baths
    • 1,586 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with LAER Realty Partners
  8. Photo of 61 Lindsay Pond Road, Concord, MA 01742 (MLS # 73394019)
    $4,450,000
    Photo of 61 Lindsay Pond Road, Concord, MA 01742 (MLS # 73394019)
    Photo of 61 Lindsay Pond Road, Concord, MA 01742 (MLS # 73394019)
    39
     
    61 Lindsay Pond Road, Concord, MA
    61 Lindsay Pond Road
    Concord, MA
    • 5 Beds
    • 6 Baths
    • 6,700 Home (sqft)
    • 6 Baths
    • 3.00 Lot (ac)
    Listed with Barrett Sotheby's International Realty
  9. Photo of 350 Gallivan Boulevard #1, Boston, MA 02124 (MLS # 73394012)
    $524,900
    Photo of 350 Gallivan Boulevard #1, Boston, MA 02124 (MLS # 73394012)
    Photo of 350 Gallivan Boulevard #1, Boston, MA 02124 (MLS # 73394012)
    31
     
    350 Gallivan Boulevard #1, Boston, MA
    350 Gallivan Boulevard #1
    Boston, MA
    • 3 Beds
    • 1 Bath
    • 1,213 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  10. Photo of 651 Main St, Hingham, MA 02043 (MLS # 73394009)
    $1,595,000
    Photo of 651 Main St, Hingham, MA 02043 (MLS # 73394009)
    Photo of 651 Main St, Hingham, MA 02043 (MLS # 73394009)
    42
     
    651 Main St, Hingham, MA
    651 Main St
    Hingham, MA
    • 5 Beds
    • 3 Baths
    • 3,647 Home (sqft)
    • 3 Baths
    • 20,909 Lot (sqft)
    Listed with Compass
  11. Photo of 2 Nikkis Way, Hadley, MA 01035 (MLS # 73394016)
    $1,048,000
    Photo of 2 Nikkis Way, Hadley, MA 01035 (MLS # 73394016)
    Photo of 2 Nikkis Way, Hadley, MA 01035 (MLS # 73394016)
    40
     
    2 Nikkis Way, Hadley, MA
    2 Nikkis Way
    Hadley, MA
    • 4 Beds
    • 4 Baths
    • 3,635 Home (sqft)
    • 4 Baths
    • 42,254 Lot (sqft)
    Listed with 5 College REALTORS®
  12. Photo of 39 Rogers Ave, Somerville, MA 02144 (MLS # 73394011)
    $2,700,000
    Photo of 39 Rogers Ave, Somerville, MA 02144 (MLS # 73394011)
    Photo of 39 Rogers Ave, Somerville, MA 02144 (MLS # 73394011)
    39 Rogers Ave, Somerville, MA
    39 Rogers Ave
    Somerville, MA
    • 4 Beds
    • 4 Baths
    • 3,100 Home (sqft)
    • 4 Baths
    • 3,485 Lot (sqft)
    Listed with Douglas Elliman Real Estate - The Sarkis Team
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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.
  19. 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
  20. 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
  21. 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
  22. 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
  23. 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
  24. 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
  25. 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
  26. 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
  27. 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
  28. 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
  29. 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
  30. 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
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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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