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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 6/22/2025)

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  1. Photo of 5 Diane Terrace #5, Scituate, MA 02066 (MLS # 73393918)
    $1,350,000
    Photo of 5 Diane Terrace #5, Scituate, MA 02066 (MLS # 73393918)
    Photo of 5 Diane Terrace #5, Scituate, MA 02066 (MLS # 73393918)
    34
     
    5 Diane Terrace #5, Scituate, MA
    5 Diane Terrace #5
    Scituate, MA
    • 2 Beds
    • 3 Baths
    • 2,601 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  2. Photo of 67 Amherst Rd #67, South Hadley, MA 01075 (MLS # 73393908)
    $625,000
    Photo of 67 Amherst Rd #67, South Hadley, MA 01075 (MLS # 73393908)
    Photo of 67 Amherst Rd #67, South Hadley, MA 01075 (MLS # 73393908)
    42
     
    67 Amherst Rd #67, South Hadley, MA
    67 Amherst Rd #67
    South Hadley, MA
    • 5 Beds
    • 3 Baths
    • 3,388 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Premier Realty Group-Hadley
  3. Photo of 1 Hunting Ln, Lynnfield, MA 01940 (MLS # 73393915)
    $839,000
    Photo of 1 Hunting Ln, Lynnfield, MA 01940 (MLS # 73393915)
    Photo of 1 Hunting Ln, Lynnfield, MA 01940 (MLS # 73393915)
    42
     
    1 Hunting Ln, Lynnfield, MA
    1 Hunting Ln
    Lynnfield, MA
    • 3 Beds
    • 3 Baths
    • 3,534 Home (sqft)
    • 3 Baths
    • 16,989 Lot (sqft)
    Listed with Coldwell Banker Realty - Lynnfield
  4. Photo of 5 Saint John Ln #5, Milford, MA 01757 (MLS # 73393906)
    $399,000
    Photo of 5 Saint John Ln #5, Milford, MA 01757 (MLS # 73393906)
    Photo of 5 Saint John Ln #5, Milford, MA 01757 (MLS # 73393906)
    29
     
    5 Saint John Ln #5, Milford, MA
    5 Saint John Ln #5
    Milford, MA
    • 2 Beds
    • 2 Baths
    • 1,101 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Mendon Local Realty
  5. Photo of 51 Lackey Street, Westborough, MA 01581 (MLS # 73393910)
    $1,195,000
    Photo of 51 Lackey Street, Westborough, MA 01581 (MLS # 73393910)
    Photo of 51 Lackey Street, Westborough, MA 01581 (MLS # 73393910)
    42
     
    51 Lackey Street, Westborough, MA
    51 Lackey Street
    Westborough, MA
    • 4 Beds
    • 5 Baths
    • 4,776 Home (sqft)
    • 5 Baths
    • 24,830 Lot (sqft)
    Listed with Mathieu Newton Sotheby's International Realty
  6. Photo of 1 Angel Way, Peabody, MA 01960 (MLS # 73393912)
    $875,000
    Photo of 1 Angel Way, Peabody, MA 01960 (MLS # 73393912)
    Photo of 1 Angel Way, Peabody, MA 01960 (MLS # 73393912)
    41
     
    1 Angel Way, Peabody, MA
    1 Angel Way
    Peabody, MA
    • 3 Beds
    • 3 Baths
    • 2,724 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
    Listed with C. Brendan Noonan & Co.
  7. Photo of 376 N Underwood St, Fall River, MA 02720 (MLS # 73393911)
    $400,000
    Photo of 376 N Underwood St, Fall River, MA 02720 (MLS # 73393911)
    Photo of 376 N Underwood St, Fall River, MA 02720 (MLS # 73393911)
    38
     
    376 N Underwood St, Fall River, MA
    376 N Underwood St
    Fall River, MA
    • 6 Beds
    • 2 Baths
    • 2,196 Home (sqft)
    • 2 Baths
    • 10,455 Lot (sqft)
    Listed with Mott & Chace Sotheby's International Realty
  8. Photo of 22 Chestnut Pl #111, Brookline, MA 02445 (MLS # 73393907)
    $579,000
    Photo of 22 Chestnut Pl #111, Brookline, MA 02445 (MLS # 73393907)
    Photo of 22 Chestnut Pl #111, Brookline, MA 02445 (MLS # 73393907)
    20
     
    22 Chestnut Pl #111, Brookline, MA
    22 Chestnut Pl #111
    Brookline, MA
    • 1 Bed
    • 2 Baths
    • 901 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Hammond Residential Real Estate
  9. Photo of 146 Chief Justic Cushing Hwy, Scituate, MA 02066 (MLS # 73393898)
    $799,000
    Photo of 146 Chief Justic Cushing Hwy, Scituate, MA 02066 (MLS # 73393898)
    Photo of 146 Chief Justic Cushing Hwy, Scituate, MA 02066 (MLS # 73393898)
    38
     
    146 Chief Justic Cushing Hwy, Scituate, MA
    146 Chief Justic Cushing Hwy
    Scituate, MA
    • 3 Beds
    • 2 Baths
    • 1,948 Home (sqft)
    • 2 Baths
    • 40,076 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  10. Photo of 50 York Ave #50, Watertown, MA 02472 (MLS # 73393901)
    $1,289,900
    Photo of 50 York Ave #50, Watertown, MA 02472 (MLS # 73393901)
    Photo of 50 York Ave #50, Watertown, MA 02472 (MLS # 73393901)
    21
     
    50 York Ave #50, Watertown, MA
    50 York Ave #50
    Watertown, MA
    • 4 Beds
    • 4 Baths
    • 2,100 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with Autograph Properties
  11. Photo of 334 Centre St #2A, Boston, MA 02122 (MLS # 73393896)
    $639,900
    Photo of 334 Centre St #2A, Boston, MA 02122 (MLS # 73393896)
    Photo of 334 Centre St #2A, Boston, MA 02122 (MLS # 73393896)
    334 Centre St #2A, Boston, MA
    334 Centre St #2A
    Boston, MA
    • 3 Beds
    • 2 Baths
    • 1,300 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Elevated Realty, LLC
  12. Photo of 27 Mystic St #2, Boston, MA 02129 (MLS # 73393897)
    $865,000
    Photo of 27 Mystic St #2, Boston, MA 02129 (MLS # 73393897)
    Photo of 27 Mystic St #2, Boston, MA 02129 (MLS # 73393897)
    14
     
    27 Mystic St #2, Boston, MA
    27 Mystic St #2
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 902 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Marblehead
  13. Photo of 26 W Park St, Franklin, MA 02038 (MLS # 73393894)
    $619,000
    Photo of 26 W Park St, Franklin, MA 02038 (MLS # 73393894)
    Photo of 26 W Park St, Franklin, MA 02038 (MLS # 73393894)
    18
     
    26 W Park St, Franklin, MA
    26 W Park St
    Franklin, MA
    • 3 Beds
    • 2 Baths
    • 2,088 Home (sqft)
    • 2 Baths
    • 16,553 Lot (sqft)
    Listed with Mass Properties Real Estate, Inc.
  14. Photo of 8 Lafayette Park #9, Lynn, MA 01902 (MLS # 73393891)
    $239,900
    Photo of 8 Lafayette Park #9, Lynn, MA 01902 (MLS # 73393891)
    Photo of 8 Lafayette Park #9, Lynn, MA 01902 (MLS # 73393891)
    20
     
    8 Lafayette Park #9, Lynn, MA
    8 Lafayette Park #9
    Lynn, MA
    • 1 Bed
    • 1 Bath
    • 588 Home (sqft)
    • 1 Bath
    • 22,216 Lot (sqft)
    Listed with Cameron Real Estate Group
  15. Photo of 12 9th St #105, Medford, MA 02155 (MLS # 73393890)
    $485,000
    Photo of 12 9th St #105, Medford, MA 02155 (MLS # 73393890)
    Photo of 12 9th St #105, Medford, MA 02155 (MLS # 73393890)
    36
     
    12 9th St #105, Medford, MA
    12 9th St #105
    Medford, MA
    • 2 Beds
    • 1 Bath
    • 860 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Century 21 North East
  16. Photo of 160 Commandants Way #401, Chelsea, MA 02150 (MLS # 73393883)
    $550,000
    Photo of 160 Commandants Way #401, Chelsea, MA 02150 (MLS # 73393883)
    Photo of 160 Commandants Way #401, Chelsea, MA 02150 (MLS # 73393883)
    15
     
    160 Commandants Way #401, Chelsea, MA
    160 Commandants Way #401
    Chelsea, MA
    • 2 Beds
    • 2 Baths
    • 1,023 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Cambridge
  17. Photo of 48 Sofia Rd, Stoughton, MA 02072 (MLS # 73393882)
    $550,000
    Photo of 48 Sofia Rd, Stoughton, MA 02072 (MLS # 73393882)
    Photo of 48 Sofia Rd, Stoughton, MA 02072 (MLS # 73393882)
    32
     
    48 Sofia Rd, Stoughton, MA
    48 Sofia Rd
    Stoughton, MA
    • 2 Beds
    • 1 Bath
    • 1,092 Home (sqft)
    • 1 Bath
    • 19,602 Lot (sqft)
    Listed with New England Asset Realty
  18. Photo of 677 Quincy Shore Drive #207, Quincy, MA 02170 (MLS # 73393880)
    $389,000
    Photo of 677 Quincy Shore Drive #207, Quincy, MA 02170 (MLS # 73393880)
    Photo of 677 Quincy Shore Drive #207, Quincy, MA 02170 (MLS # 73393880)
    14
     
    677 Quincy Shore Drive #207, Quincy, MA
    677 Quincy Shore Drive #207
    Quincy, MA
    • 1 Bed
    • 1 Bath
    • 783 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  19. Photo of 12 Stoneholm St #621, Boston, MA 02115 (MLS # 73393874)
    $699,000
    Photo of 12 Stoneholm St #621, Boston, MA 02115 (MLS # 73393874)
    Photo of 12 Stoneholm St #621, Boston, MA 02115 (MLS # 73393874)
    20
     
    12 Stoneholm St #621, Boston, MA
    12 Stoneholm St #621
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 639 Home (sqft)
    • 2 Baths
    • 436 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  20. Photo of 11 Williams St, Arlington, MA 02476 (MLS # 73393872)
    $1,345,000
    Photo of 11 Williams St, Arlington, MA 02476 (MLS # 73393872)
    Photo of 11 Williams St, Arlington, MA 02476 (MLS # 73393872)
    39
     
    11 Williams St, Arlington, MA
    11 Williams St
    Arlington, MA
    • 4 Beds
    • 3 Baths
    • 2,480 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
    Listed with Leading Edge Real Estate
  21. Photo of 338 Forest St, Arlington, MA 02474 (MLS # 73393867)
    $895,000
    Photo of 338 Forest St, Arlington, MA 02474 (MLS # 73393867)
    Photo of 338 Forest St, Arlington, MA 02474 (MLS # 73393867)
    42
     
    338 Forest St, Arlington, MA
    338 Forest St
    Arlington, MA
    • 3 Beds
    • 2 Baths
    • 1,691 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  22. Photo of 664 Washington St, Boston, MA 02135 (MLS # 73393873)
    $3,930,000
    Photo of 664 Washington St, Boston, MA 02135 (MLS # 73393873)
    Photo of 664 Washington St, Boston, MA 02135 (MLS # 73393873)
    40
     
    664 Washington St, Boston, MA
    664 Washington St
    Boston, MA
    • 14 Beds
    • 6 Baths
    • 0 Home (sqft)
    • 6 Baths
    • 33,106 Lot (sqft)
    Listed with Sunrise Realty & Investment LLC
  23. Photo of 11 Harris St, Wilmington, MA 01887 (MLS # 73393871)
    $620,000
    Photo of 11 Harris St, Wilmington, MA 01887 (MLS # 73393871)
    Photo of 11 Harris St, Wilmington, MA 01887 (MLS # 73393871)
    34
     
    11 Harris St, Wilmington, MA
    11 Harris St
    Wilmington, MA
    • 3 Beds
    • 2 Baths
    • 2,024 Home (sqft)
    • 2 Baths
    • 16,989 Lot (sqft)
    Listed with StartPoint Realty
  24. Photo of 43 Shirley Ave, Methuen, MA 01844 (MLS # 73393869)
    $549,900
    Photo of 43 Shirley Ave, Methuen, MA 01844 (MLS # 73393869)
    Photo of 43 Shirley Ave, Methuen, MA 01844 (MLS # 73393869)
    18
     
    43 Shirley Ave, Methuen, MA
    43 Shirley Ave
    Methuen, MA
    • 3 Beds
    • 2 Baths
    • 1,752 Home (sqft)
    • 2 Baths
    • 12,197 Lot (sqft)
    Listed with Ciccarelli Homes
  25. Photo of 110 Essex Street, Beverly, MA 01915 (MLS # 73393864)
    $789,000
    Photo of 110 Essex Street, Beverly, MA 01915 (MLS # 73393864)
    Photo of 110 Essex Street, Beverly, MA 01915 (MLS # 73393864)
    39
     
    110 Essex Street, Beverly, MA
    110 Essex Street
    Beverly, MA
    • 4 Beds
    • 2 Baths
    • 2,028 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
    Listed with Compass
  26. Photo of 58 Gleason Street, Medford, MA 02155 (MLS # 73393866)
    $875,000
    Photo of 58 Gleason Street, Medford, MA 02155 (MLS # 73393866)
    Photo of 58 Gleason Street, Medford, MA 02155 (MLS # 73393866)
    36
     
    58 Gleason Street, Medford, MA
    58 Gleason Street
    Medford, MA
    • 3 Beds
    • 2 Baths
    • 1,585 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
    Listed with Compass
  27. Photo of 37 Green Hill Pkwy, Worcester, MA 01605 (MLS # 73393868)
    $775,000
    Photo of 37 Green Hill Pkwy, Worcester, MA 01605 (MLS # 73393868)
    Photo of 37 Green Hill Pkwy, Worcester, MA 01605 (MLS # 73393868)
    20
     
    37 Green Hill Pkwy, Worcester, MA
    37 Green Hill Pkwy
    Worcester, MA
    • 9 Beds
    • 3 Baths
    • 3,675 Home (sqft)
    • 3 Baths
    • 2,178 Lot (sqft)
    Listed with www.HomeZu.com
  28. Photo of 14 Adams Rd, Ashland, MA 01721 (MLS # 73393876)
    $619,900
    Photo of 14 Adams Rd, Ashland, MA 01721 (MLS # 73393876)
    Photo of 14 Adams Rd, Ashland, MA 01721 (MLS # 73393876)
    26
     
    14 Adams Rd, Ashland, MA
    14 Adams Rd
    Ashland, MA
    • 4 Beds
    • 4 Baths
    • 2,017 Home (sqft)
    • 4 Baths
    • 9,584 Lot (sqft)
    Listed with Mega Realty Services
  29. Photo of 11 Olde Stable Lane, Easton, MA 02356 (MLS # 73393870)
    $1,800,000
    Photo of 11 Olde Stable Lane, Easton, MA 02356 (MLS # 73393870)
    Photo of 11 Olde Stable Lane, Easton, MA 02356 (MLS # 73393870)
    42
     
    11 Olde Stable Lane, Easton, MA
    11 Olde Stable Lane
    Easton, MA
    • 5 Beds
    • 4 Baths
    • 3,200 Home (sqft)
    • 4 Baths
    • 1.69 Lot (ac)
    Listed with North East Realty Group
  30. Photo of 3 Sears Ave, Webster, MA 01570 (MLS # 73393878)
    $339,900
    Photo of 3 Sears Ave, Webster, MA 01570 (MLS # 73393878)
    Photo of 3 Sears Ave, Webster, MA 01570 (MLS # 73393878)
    27
     
    3 Sears Ave, Webster, MA
    3 Sears Ave
    Webster, MA
    • 3 Beds
    • 1 Bath
    • 1,008 Home (sqft)
    • 1 Bath
    • 10,019 Lot (sqft)
    Listed with 1 Worcester Homes
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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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