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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 1/22/2025)

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  1. Photo of 36 Bonneville Ave, Chicopee, MA 01013 (MLS # 73328074)
    $279,900
    Photo of 36 Bonneville Ave, Chicopee, MA 01013 (MLS # 73328074)
    Photo of 36 Bonneville Ave, Chicopee, MA 01013 (MLS # 73328074)
    31
     
    36 Bonneville Ave, Chicopee, MA
    36 Bonneville Ave
    Chicopee, MA
    • 4 Beds
    • 1 Bath
    • 1,080 Home (sqft)
    • 1 Bath
    • 11,762 Lot (sqft)
    Listed with ERA M Connie Laplante Real Estate
  2. Photo of 104 5th St, Fall River, MA 02721 (MLS # 73328075)
    $599,000
    Photo of 104 5th St, Fall River, MA 02721 (MLS # 73328075)
    Photo of 104 5th St, Fall River, MA 02721 (MLS # 73328075)
    29
     
    104 5th St, Fall River, MA
    104 5th St
    Fall River, MA
    • 5 Beds
    • 4 Baths
    • 2,678 Home (sqft)
    • 4 Baths
    • 3,050 Lot (sqft)
    Listed with Re/Max Impact
  3. Photo of LOT 11 Angelina Way, Taunton, MA 02780 (MLS # 73328071)
    $749,900
    Photo of LOT 11 Angelina Way, Taunton, MA 02780 (MLS # 73328071)
    Photo of LOT 11 Angelina Way, Taunton, MA 02780 (MLS # 73328071)
    16
     
    LOT 11 Angelina Way, Taunton, MA
    LOT 11 Angelina Way
    Taunton, MA
    • 3 Beds
    • 3 Baths
    • 2,200 Home (sqft)
    • 3 Baths
    • 1.07 Lot (ac)
    Listed with Realty Executives Metro South
  4. Photo of 372 Athens St #3, Boston, MA 02127 (MLS # 73328070)
    $625,000
    Photo of 372 Athens St #3, Boston, MA 02127 (MLS # 73328070)
    Photo of 372 Athens St #3, Boston, MA 02127 (MLS # 73328070)
    372 Athens St #3, Boston, MA
    372 Athens St #3
    Boston, MA
    • 1 Bed
    • 2 Baths
    • 604 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  5. Photo of 33 Paige Hill Rd, Brimfield, MA 01010 (MLS # 73328047)
    $799,900
    Photo of 33 Paige Hill Rd, Brimfield, MA 01010 (MLS # 73328047)
    Photo of 33 Paige Hill Rd, Brimfield, MA 01010 (MLS # 73328047)
    42
     
    33 Paige Hill Rd, Brimfield, MA
    33 Paige Hill Rd
    Brimfield, MA
    • 2 Beds
    • 2 Baths
    • 3,137 Home (sqft)
    • 2 Baths
    • 5.20 Lot (ac)
    Listed with Executive Real Estate, Inc.
  6. Photo of 19 Harris Street #2, Cambridge, MA 02138 (MLS # 73328069)
    $799,000
    Photo of 19 Harris Street #2, Cambridge, MA 02138 (MLS # 73328069)
    Photo of 19 Harris Street #2, Cambridge, MA 02138 (MLS # 73328069)
    24
     
    19 Harris Street #2, Cambridge, MA
    19 Harris Street #2
    Cambridge, MA
    • 2 Beds
    • 2 Baths
    • 925 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  7. Photo of 2 Rita Cir, South Hadley, MA 01075 (MLS # 73328064)
    $460,000
    Photo of 2 Rita Cir, South Hadley, MA 01075 (MLS # 73328064)
    Photo of 2 Rita Cir, South Hadley, MA 01075 (MLS # 73328064)
    42
     
    2 Rita Cir, South Hadley, MA
    2 Rita Cir
    South Hadley, MA
    • 6 Beds
    • 2 Baths
    • 1,992 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
    Listed with MA Homes, LLC
  8. Photo of 40 Grand St, Fitchburg, MA 01420 (MLS # 73328065)
    $399,900
    Photo of 40 Grand St, Fitchburg, MA 01420 (MLS # 73328065)
    Photo of 40 Grand St, Fitchburg, MA 01420 (MLS # 73328065)
    36
     
    40 Grand St, Fitchburg, MA
    40 Grand St
    Fitchburg, MA
    • 5 Beds
    • 1 Bath
    • 1,602 Home (sqft)
    • 1 Bath
    • 15,246 Lot (sqft)
    Listed with Parkhill Realty Group
  9. Photo of 390 High St #6, Clinton, MA 01510 (MLS # 73328066)
    $279,900
    Photo of 390 High St #6, Clinton, MA 01510 (MLS # 73328066)
    Photo of 390 High St #6, Clinton, MA 01510 (MLS # 73328066)
    24
     
    390 High St #6, Clinton, MA
    390 High St #6
    Clinton, MA
    • 2 Beds
    • 1 Bath
    • 872 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with 1 Worcester Homes
  10. Photo of 21 Beechwood Ave, Pembroke, MA 02359 (MLS # 73328063)
    $699,900
    Photo of 21 Beechwood Ave, Pembroke, MA 02359 (MLS # 73328063)
    Photo of 21 Beechwood Ave, Pembroke, MA 02359 (MLS # 73328063)
    42
     
    21 Beechwood Ave, Pembroke, MA
    21 Beechwood Ave
    Pembroke, MA
    • 3 Beds
    • 2 Baths
    • 1,917 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
    Listed with Jones and Jones Realty, Inc.
  11. Photo of 17B Cork Circle #17B, Millville, MA 01529 (MLS # 73328056)
    $319,900
    Photo of 17B Cork Circle #17B, Millville, MA 01529 (MLS # 73328056)
    Photo of 17B Cork Circle #17B, Millville, MA 01529 (MLS # 73328056)
    35
     
    17B Cork Circle #17B, Millville, MA
    17B Cork Circle #17B
    Millville, MA
    • 2 Beds
    • 2 Baths
    • 1,289 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Hayden Rowe Properties
  12. Photo of 580 Quarry Street #7, Quincy, MA 02169 (MLS # 73328061)
    $625,000
    Photo of 580 Quarry Street #7, Quincy, MA 02169 (MLS # 73328061)
    Photo of 580 Quarry Street #7, Quincy, MA 02169 (MLS # 73328061)
    22
     
    580 Quarry Street #7, Quincy, MA
    580 Quarry Street #7
    Quincy, MA
    • 2 Beds
    • 2 Baths
    • 1,182 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  13. Photo of 1 Lanark Rd, Arlington, MA 02476 (MLS # 73328055)
    $720,000
    Photo of 1 Lanark Rd, Arlington, MA 02476 (MLS # 73328055)
    Photo of 1 Lanark Rd, Arlington, MA 02476 (MLS # 73328055)
    36
     
    1 Lanark Rd, Arlington, MA
    1 Lanark Rd
    Arlington, MA
    • 3 Beds
    • 1 Bath
    • 1,152 Home (sqft)
    • 1 Bath
    • 2,178 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  14. Photo of 288 E Main St, Orange, MA 01364 (MLS # 73328054)
    $279,900
    Photo of 288 E Main St, Orange, MA 01364 (MLS # 73328054)
    Photo of 288 E Main St, Orange, MA 01364 (MLS # 73328054)
    33
     
    288 E Main St, Orange, MA
    288 E Main St
    Orange, MA
    • 3 Beds
    • 1 Bath
    • 1,601 Home (sqft)
    • 1 Bath
    • 11,326 Lot (sqft)
    Listed with Compass Realty
  15. Photo of 8 Whittier Place #20A, Boston, MA 02114 (MLS # 73328050)
    $525,000
    Photo of 8 Whittier Place #20A, Boston, MA 02114 (MLS # 73328050)
    Photo of 8 Whittier Place #20A, Boston, MA 02114 (MLS # 73328050)
    20
     
    8 Whittier Place #20A, Boston, MA
    8 Whittier Place #20A
    Boston, MA
    • 1 Bed
    • 1 Bath
    • 935 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
    Listed with Dreamega International Realty LLC
  16. Photo of 9 Chauncy St #20, Cambridge, MA 02138 (MLS # 73328049)
    $779,000
    Photo of 9 Chauncy St #20, Cambridge, MA 02138 (MLS # 73328049)
    Photo of 9 Chauncy St #20, Cambridge, MA 02138 (MLS # 73328049)
    20
     
    9 Chauncy St #20, Cambridge, MA
    9 Chauncy St #20
    Cambridge, MA
    • 2 Beds
    • 1 Bath
    • 805 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Dreamega International Realty LLC
  17. Photo of 29 Emerald Ave, Hampton, NH 03842 (MLS # 73328044)
    $615,000
    Photo of 29 Emerald Ave, Hampton, NH 03842 (MLS # 73328044)
    Photo of 29 Emerald Ave, Hampton, NH 03842 (MLS # 73328044)
    29
     
    29 Emerald Ave, Hampton, NH
    29 Emerald Ave
    Hampton, NH
    • 2 Beds
    • 2 Baths
    • 1,240 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
    Listed with Compass
  18. Photo of 107 Center St, Raynham, MA 02767 (MLS # 73328042)
    $574,900
    Photo of 107 Center St, Raynham, MA 02767 (MLS # 73328042)
    Photo of 107 Center St, Raynham, MA 02767 (MLS # 73328042)
    23
     
    107 Center St, Raynham, MA
    107 Center St
    Raynham, MA
    • 3 Beds
    • 2 Baths
    • 1,200 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
    Listed with Nichole Sliney Realty Team
  19. Photo of 44 Robeson Street, Boston, MA 02130 (MLS # 73328040)
    $2,750,000
    Photo of 44 Robeson Street, Boston, MA 02130 (MLS # 73328040)
    Photo of 44 Robeson Street, Boston, MA 02130 (MLS # 73328040)
    32
     
    44 Robeson Street, Boston, MA
    44 Robeson Street
    Boston, MA
    • 5 Beds
    • 3 Baths
    • 3,319 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  20. Photo of 44 Robeson Street #B, Boston, MA 02130 (MLS # 73328041)
    $2,750,000
    Photo of 44 Robeson Street #B, Boston, MA 02130 (MLS # 73328041)
    Photo of 44 Robeson Street #B, Boston, MA 02130 (MLS # 73328041)
    32
     
    44 Robeson Street #B, Boston, MA
    44 Robeson Street #B
    Boston, MA
    • 5 Beds
    • 3 Baths
    • 3,319 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  21. Photo of 8 Sim Road, Saugus, MA 01906 (MLS # 73328035)
    $1,010,000
    Photo of 8 Sim Road, Saugus, MA 01906 (MLS # 73328035)
    Photo of 8 Sim Road, Saugus, MA 01906 (MLS # 73328035)
    37
     
    8 Sim Road, Saugus, MA
    8 Sim Road
    Saugus, MA
    • 4 Beds
    • 4 Baths
    • 3,469 Home (sqft)
    • 4 Baths
    • 11,762 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Verani Realty Bradford
  22. Photo of 43 Angleside Rd #2, Waltham, MA 02453 (MLS # 73328036)
    $519,000
    Photo of 43 Angleside Rd #2, Waltham, MA 02453 (MLS # 73328036)
    Photo of 43 Angleside Rd #2, Waltham, MA 02453 (MLS # 73328036)
    24
     
    43 Angleside Rd #2, Waltham, MA
    43 Angleside Rd #2
    Waltham, MA
    • 2 Beds
    • 2 Baths
    • 1,162 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Realty-Merrimack
  23. Photo of 23 Waltham Street #23, Watertown, MA 02472 (MLS # 73328037)
    $929,900
    Photo of 23 Waltham Street #23, Watertown, MA 02472 (MLS # 73328037)
    Photo of 23 Waltham Street #23, Watertown, MA 02472 (MLS # 73328037)
    25
     
    23 Waltham Street #23, Watertown, MA
    23 Waltham Street #23
    Watertown, MA
    • 3 Beds
    • 2 Baths
    • 1,395 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  24. Photo of 680 Broadway St #1, Chelsea, MA 02150 (MLS # 73328031)
    $479,000
    Photo of 680 Broadway St #1, Chelsea, MA 02150 (MLS # 73328031)
    Photo of 680 Broadway St #1, Chelsea, MA 02150 (MLS # 73328031)
    31
     
    680 Broadway St #1, Chelsea, MA
    680 Broadway St #1
    Chelsea, MA
    • 2 Beds
    • 1 Bath
    • 1,224 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Four Points Real Estate, LLC
  25. Photo of 5 Pleasant St, Lunenburg, MA 01462 (MLS # 73328030)
    $389,900
    Photo of 5 Pleasant St, Lunenburg, MA 01462 (MLS # 73328030)
    Photo of 5 Pleasant St, Lunenburg, MA 01462 (MLS # 73328030)
    11
     
    5 Pleasant St, Lunenburg, MA
    5 Pleasant St
    Lunenburg, MA
    • 3 Beds
    • 2 Baths
    • 1,523 Home (sqft)
    • 2 Baths
    • 18,296 Lot (sqft)
    Listed with Tammy Morrison Real Estate
  26. Photo of 121A Warren Avenue, Boston, MA 02116 (MLS # 73328027)
    $4,495,000
    Photo of 121A Warren Avenue, Boston, MA 02116 (MLS # 73328027)
    Photo of 121A Warren Avenue, Boston, MA 02116 (MLS # 73328027)
    19
     
    121A Warren Avenue, Boston, MA
    121A Warren Avenue
    Boston, MA
    • 4 Beds
    • 5 Baths
    • 3,450 Home (sqft)
    • 5 Baths
    • 872 Lot (sqft)
    Listed with Columbus and Over Group, LLC
  27. Photo of 18 Chandler Terrace #1, Lynn, MA 01902 (MLS # 73328026)
    $449,000
    Photo of 18 Chandler Terrace #1, Lynn, MA 01902 (MLS # 73328026)
    Photo of 18 Chandler Terrace #1, Lynn, MA 01902 (MLS # 73328026)
    41
     
    18 Chandler Terrace #1, Lynn, MA
    18 Chandler Terrace #1
    Lynn, MA
    • 4 Beds
    • 2 Baths
    • 1,380 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Windhill Realty, LLC
  28. Photo of 6 Sidney Ave, Lynn, MA 01902 (MLS # 73328028)
    $589,000
    Photo of 6 Sidney Ave, Lynn, MA 01902 (MLS # 73328028)
    Photo of 6 Sidney Ave, Lynn, MA 01902 (MLS # 73328028)
    18
     
    6 Sidney Ave, Lynn, MA
    6 Sidney Ave
    Lynn, MA
    • 4 Beds
    • 2 Baths
    • 1,550 Home (sqft)
    • 2 Baths
    • 3,485 Lot (sqft)
    Listed with Cameron Real Estate Group
  29. Photo of 118 Oak Hill, Seekonk, MA 02771 (MLS # 73328023)
    $750,000
    Photo of 118 Oak Hill, Seekonk, MA 02771 (MLS # 73328023)
    Photo of 118 Oak Hill, Seekonk, MA 02771 (MLS # 73328023)
    36
     
    118 Oak Hill, Seekonk, MA
    118 Oak Hill
    Seekonk, MA
    • 3 Beds
    • 3 Baths
    • 2,160 Home (sqft)
    • 3 Baths
    • 20,038 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  30. Photo of 123 West, Attleboro, MA 02703 (MLS # 73328020)
    $799,999
    Photo of 123 West, Attleboro, MA 02703 (MLS # 73328020)
    Photo of 123 West, Attleboro, MA 02703 (MLS # 73328020)
    38
     
    123 West, Attleboro, MA
    123 West
    Attleboro, MA
    • 4 Beds
    • 3 Baths
    • 2,350 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
    Listed with Century 21 The Seyboth Team
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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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