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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 6/20/2025)

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  1. Photo of 65 Blake Rd, Lexington, MA 02420 (MLS # 73394050)
    $1,995,000
    Photo of 65 Blake Rd, Lexington, MA 02420 (MLS # 73394050)
    Photo of 65 Blake Rd, Lexington, MA 02420 (MLS # 73394050)
    42
     
    65 Blake Rd, Lexington, MA
    65 Blake Rd
    Lexington, MA
    • 4 Beds
    • 3 Baths
    • 3,650 Home (sqft)
    • 3 Baths
    • 18,296 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  2. Photo of 69 Dracut St, Boston, MA 02124 (MLS # 73394046)
    $825,000
    Photo of 69 Dracut St, Boston, MA 02124 (MLS # 73394046)
    Photo of 69 Dracut St, Boston, MA 02124 (MLS # 73394046)
    24
     
    69 Dracut St, Boston, MA
    69 Dracut St
    Boston, MA
    • 5 Beds
    • 1 Bath
    • 2,153 Home (sqft)
    • 1 Bath
    • 3,050 Lot (sqft)
    Listed with Compass
  3. Photo of 21 Central Ave #30, Everett, MA 02149 (MLS # 73394040)
    $320,000
    Photo of 21 Central Ave #30, Everett, MA 02149 (MLS # 73394040)
    Photo of 21 Central Ave #30, Everett, MA 02149 (MLS # 73394040)
    20
     
    21 Central Ave #30, Everett, MA
    21 Central Ave #30
    Everett, MA
    • 2 Beds
    • 1 Bath
    • 802 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Lillian Montalto Signature Properties
  4. Photo of 173 Oak St #208W, Newton, MA 02464 (MLS # 73394044)
    $709,000
    Photo of 173 Oak St #208W, Newton, MA 02464 (MLS # 73394044)
    Photo of 173 Oak St #208W, Newton, MA 02464 (MLS # 73394044)
    22
     
    173 Oak St #208W, Newton, MA
    173 Oak St #208W
    Newton, MA
    • 2 Beds
    • 2 Baths
    • 1,144 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Realty
  5. Photo of 111 School St #6, Dennis, MA 02670 (MLS # 73394047)
    $499,000
    Photo of 111 School St #6, Dennis, MA 02670 (MLS # 73394047)
    Photo of 111 School St #6, Dennis, MA 02670 (MLS # 73394047)
    39
     
    111 School St #6, Dennis, MA
    111 School St #6
    Dennis, MA
    • 2 Beds
    • 2 Baths
    • 1,044 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  6. Photo of 10 Whittier Rd, Natick, MA 01760 (MLS # 73394053)
    $1,745,000
    Photo of 10 Whittier Rd, Natick, MA 01760 (MLS # 73394053)
    Photo of 10 Whittier Rd, Natick, MA 01760 (MLS # 73394053)
    40
     
    10 Whittier Rd, Natick, MA
    10 Whittier Rd
    Natick, MA
    • 5 Beds
    • 4 Baths
    • 4,050 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
    Listed with Coppellotti Homes Realty LLC
  7. Photo of 7 Holmes St, Quincy, MA 02171 (MLS # 73394034)
    $4,000,000
    Photo of 7 Holmes St, Quincy, MA 02171 (MLS # 73394034)
    Photo of 7 Holmes St, Quincy, MA 02171 (MLS # 73394034)
    7 Holmes St, Quincy, MA
    7 Holmes St
    Quincy, MA
    • 12 Beds
    • 12 Baths
    • 7,530 Home (sqft)
    • 12 Baths
    • 8,277 Lot (sqft)
    Listed with United Multi Family Corporation
  8. Photo of 204 Princeton St, Boston, MA 02128 (MLS # 73394039)
    $989,000
    Photo of 204 Princeton St, Boston, MA 02128 (MLS # 73394039)
    Photo of 204 Princeton St, Boston, MA 02128 (MLS # 73394039)
    18
     
    204 Princeton St, Boston, MA
    204 Princeton St
    Boston, MA
    • 5 Beds
    • 3 Baths
    • 2,019 Home (sqft)
    • 3 Baths
    • 872 Lot (sqft)
    Listed with Compass
  9. Photo of 3 Penni Ln, Andover, MA 01810 (MLS # 73394036)
    $949,900
    Photo of 3 Penni Ln, Andover, MA 01810 (MLS # 73394036)
    Photo of 3 Penni Ln, Andover, MA 01810 (MLS # 73394036)
    35
     
    3 Penni Ln, Andover, MA
    3 Penni Ln
    Andover, MA
    • 4 Beds
    • 3 Baths
    • 2,312 Home (sqft)
    • 3 Baths
    • 1.13 Lot (ac)
    Listed with RE/MAX Partners
  10. Photo of 100 Overlook Ter, Dracut, MA 01826 (MLS # 73394028)
    $799,000
    Photo of 100 Overlook Ter, Dracut, MA 01826 (MLS # 73394028)
    Photo of 100 Overlook Ter, Dracut, MA 01826 (MLS # 73394028)
    39
     
    100 Overlook Ter, Dracut, MA
    100 Overlook Ter
    Dracut, MA
    • 4 Beds
    • 3 Baths
    • 2,528 Home (sqft)
    • 3 Baths
    • 1.20 Lot (ac)
    Listed with LAER Realty Partners
  11. Photo of 6 Woods Hill Circle, Woburn, MA 01801 (MLS # 73394024)
    $1,099,000
    Photo of 6 Woods Hill Circle, Woburn, MA 01801 (MLS # 73394024)
    Photo of 6 Woods Hill Circle, Woburn, MA 01801 (MLS # 73394024)
    41
     
    6 Woods Hill Circle, Woburn, MA
    6 Woods Hill Circle
    Woburn, MA
    • 4 Beds
    • 3 Baths
    • 3,010 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
    Listed with Better Homes and Gardens Real Estate - The Shanahan Group
  12. Photo of 423 Grove Street, Reading, MA 01867 (MLS # 73394025)
    $899,000
    Photo of 423 Grove Street, Reading, MA 01867 (MLS # 73394025)
    Photo of 423 Grove Street, Reading, MA 01867 (MLS # 73394025)
    35
     
    423 Grove Street, Reading, MA
    423 Grove Street
    Reading, MA
    • 3 Beds
    • 2 Baths
    • 1,659 Home (sqft)
    • 2 Baths
    • 1.50 Lot (ac)
    Listed with Coldwell Banker Realty - Lexington
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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.
  19. 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
  20. 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
  21. 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.
  22. 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
  23. 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®
  24. 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
  25. 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
  26. 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
  27. 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
  28. 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
  29. 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
  30. 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.
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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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