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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 2/27/2024)

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  1. Photo of 144 Pleasant Street, Marlborough, MA 01752 (MLS # 73205134)
    $700,000
    Photo of 144 Pleasant Street, Marlborough, MA 01752 (MLS # 73205134)
    Photo of 144 Pleasant Street, Marlborough, MA 01752 (MLS # 73205134)
    42
     
    144 Pleasant Street, Marlborough, MA
    144 Pleasant Street
    Marlborough, MA
    • 6 Beds
    • 3 Baths
    • 2,852 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  2. Photo of 80 Archer St, Wrentham, MA 02093 (MLS # 73203777)
    $700,000
    Photo of 80 Archer St, Wrentham, MA 02093 (MLS # 73203777)
    Photo of 80 Archer St, Wrentham, MA 02093 (MLS # 73203777)
    32
     
    80 Archer St, Wrentham, MA
    80 Archer St
    Wrentham, MA
    • 3 Beds
    • 3 Baths
    • 2,100 Home (sqft)
    • 3 Baths
    • 14,811 Lot (sqft)
    Listed with Century 21 North East
  3. Photo of 16 Evergreen Way, Medfield, MA 02052 (MLS # 73204503)
    $1,190,000
    Photo of 16 Evergreen Way, Medfield, MA 02052 (MLS # 73204503)
    Photo of 16 Evergreen Way, Medfield, MA 02052 (MLS # 73204503)
    42
     
    16 Evergreen Way, Medfield, MA
    16 Evergreen Way
    Medfield, MA
    • 4 Beds
    • 3 Baths
    • 4,132 Home (sqft)
    • 3 Baths
    • 24,830 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Evolution Properties
  4. Photo of 176 Legros Street, Fitchburg, MA 01420 (MLS # 73205052)
    $525,000
    Photo of 176 Legros Street, Fitchburg, MA 01420 (MLS # 73205052)
    Photo of 176 Legros Street, Fitchburg, MA 01420 (MLS # 73205052)
    42
     
    176 Legros Street, Fitchburg, MA
    176 Legros Street
    Fitchburg, MA
    • 4 Beds
    • 3 Baths
    • 2,187 Home (sqft)
    • 3 Baths
    • 31,799 Lot (sqft)
    Listed with Keller Williams Realty North Central
  5. Photo of 148 Summer St, Somerville, MA 02143 (MLS # 73203749)
    $1,100,000
    Photo of 148 Summer St, Somerville, MA 02143 (MLS # 73203749)
    Photo of 148 Summer St, Somerville, MA 02143 (MLS # 73203749)
    24
     
    148 Summer St, Somerville, MA
    148 Summer St
    Somerville, MA
    • 5 Beds
    • 2 Baths
    • 2,341 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
    Listed with Coldwell Banker Realty - Brookline
  6. Photo of 1774 Beacon St #4, Brookline, MA 02445 (MLS # 73205232)
    $825,000
    Photo of 1774 Beacon St #4, Brookline, MA 02445 (MLS # 73205232)
    Photo of 1774 Beacon St #4, Brookline, MA 02445 (MLS # 73205232)
    14
     
    1774 Beacon St #4, Brookline, MA
    1774 Beacon St #4
    Brookline, MA
    • 2 Beds
    • 1 Bath
    • 1,000 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Hammond Residential Real Estate
  7. Photo of 55 Cottage Lane, Mashpee, MA 02649 (MLS # 73205064)
    $1,825,000
    Photo of 55 Cottage Lane, Mashpee, MA 02649 (MLS # 73205064)
    Photo of 55 Cottage Lane, Mashpee, MA 02649 (MLS # 73205064)
    42
     
    55 Cottage Lane, Mashpee, MA
    55 Cottage Lane
    Mashpee, MA
    • 5 Beds
    • 4 Baths
    • 2,216 Home (sqft)
    • 4 Baths
    • 4,792 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  8. Photo of 697 Broadway, Fall River, MA 02724 (MLS # 73205752)
    $689,000
    Photo of 697 Broadway, Fall River, MA 02724 (MLS # 73205752)
    Photo of 697 Broadway, Fall River, MA 02724 (MLS # 73205752)
    22
     
    697 Broadway, Fall River, MA
    697 Broadway
    Fall River, MA
    • 8 Beds
    • 3 Baths
    • 3,804 Home (sqft)
    • 3 Baths
    • 5,228 Lot (sqft)
    Listed with eXp Realty
  9. Photo of 13 Dresser Hill Rd, Charlton, MA 01507 (MLS # 73205751)
    $649,900
    Photo of 13 Dresser Hill Rd, Charlton, MA 01507 (MLS # 73205751)
    Photo of 13 Dresser Hill Rd, Charlton, MA 01507 (MLS # 73205751)
    30
     
    13 Dresser Hill Rd, Charlton, MA
    13 Dresser Hill Rd
    Charlton, MA
    • 4 Beds
    • 3 Baths
    • 2,500 Home (sqft)
    • 3 Baths
    • 1.38 Lot (ac)
    Listed with RE/MAX Diverse
  10. Photo of 117 Church St #4, Watertown, MA 02472 (MLS # 73205750)
    $675,000
    Photo of 117 Church St #4, Watertown, MA 02472 (MLS # 73205750)
    Photo of 117 Church St #4, Watertown, MA 02472 (MLS # 73205750)
    36
     
    117 Church St #4, Watertown, MA
    117 Church St #4
    Watertown, MA
    • 2 Beds
    • 1 Bath
    • 1,254 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  11. Photo of 79 Elmcrest Dr #79, Chicopee, MA 01013 (MLS # 73205748)
    $448,000
    Photo of 79 Elmcrest Dr #79, Chicopee, MA 01013 (MLS # 73205748)
    Photo of 79 Elmcrest Dr #79, Chicopee, MA 01013 (MLS # 73205748)
    79 Elmcrest Dr #79, Chicopee, MA
    79 Elmcrest Dr #79
    Chicopee, MA
    • 3 Beds
    • 3 Baths
    • 1,287 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with HB Real Estate, LLC
  12. Photo of 19 Astor St, Lynn, MA 01905 (MLS # 73205746)
    $525,000
    Photo of 19 Astor St, Lynn, MA 01905 (MLS # 73205746)
    Photo of 19 Astor St, Lynn, MA 01905 (MLS # 73205746)
    37
     
    19 Astor St, Lynn, MA
    19 Astor St
    Lynn, MA
    • 3 Beds
    • 3 Baths
    • 1,408 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
    Listed with Citipoint Realty Services, LLC
  13. Photo of 212 Beacon St #1, Boston, MA 02116 (MLS # 73205597)
    $3,400,000
    Photo of 212 Beacon St #1, Boston, MA 02116 (MLS # 73205597)
    Photo of 212 Beacon St #1, Boston, MA 02116 (MLS # 73205597)
    16
     
    212 Beacon St #1, Boston, MA
    212 Beacon St #1
    Boston, MA
    • 2 Beds
    • 3 Baths
    • 1,740 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
    Listed with MGS Group Real Estate LTD
  14. Photo of 1089 Westhampton Rd, Northampton, MA 01062 (MLS # 73205657)
    $1,850,000
    Photo of 1089 Westhampton Rd, Northampton, MA 01062 (MLS # 73205657)
    Photo of 1089 Westhampton Rd, Northampton, MA 01062 (MLS # 73205657)
    42
     
    1089 Westhampton Rd, Northampton, MA
    1089 Westhampton Rd
    Northampton, MA
    • 4 Beds
    • 5 Baths
    • 6,301 Home (sqft)
    • 5 Baths
    • 6.28 Lot (ac)
    Listed with Maple and Main Realty, LLC
  15. Photo of 477 Oakhill Ave, Attleboro, MA 02703 (MLS # 73205745)
    $514,900
    Photo of 477 Oakhill Ave, Attleboro, MA 02703 (MLS # 73205745)
    Photo of 477 Oakhill Ave, Attleboro, MA 02703 (MLS # 73205745)
    18
     
    477 Oakhill Ave, Attleboro, MA
    477 Oakhill Ave
    Attleboro, MA
    • 3 Beds
    • 2 Baths
    • 1,718 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  16. Photo of 53 Montgomery St, North Adams, MA 01247 (MLS # 73205744)
    $209,000
    Photo of 53 Montgomery St, North Adams, MA 01247 (MLS # 73205744)
    Photo of 53 Montgomery St, North Adams, MA 01247 (MLS # 73205744)
    15
     
    53 Montgomery St, North Adams, MA
    53 Montgomery St
    North Adams, MA
    • 7 Beds
    • 1 Bath
    • 1,632 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
    Listed with eRealty Advisors, Inc.
  17. Photo of 25 Pine St, Danvers, MA 01923 (MLS # 73205743)
    $525,000
    Photo of 25 Pine St, Danvers, MA 01923 (MLS # 73205743)
    Photo of 25 Pine St, Danvers, MA 01923 (MLS # 73205743)
    28
     
    25 Pine St, Danvers, MA
    25 Pine St
    Danvers, MA
    • 3 Beds
    • 2 Baths
    • 1,479 Home (sqft)
    • 2 Baths
    • 25,265 Lot (sqft)
    Listed with Cameron Real Estate Group
  18. Photo of 221 Columbia St, Cambridge, MA 02139 (MLS # 73205742)
    $3,995,000
    Photo of 221 Columbia St, Cambridge, MA 02139 (MLS # 73205742)
    Photo of 221 Columbia St, Cambridge, MA 02139 (MLS # 73205742)
    42
     
    221 Columbia St, Cambridge, MA
    221 Columbia St
    Cambridge, MA
    • 6 Beds
    • 5 Baths
    • 4,646 Home (sqft)
    • 5 Baths
    • 4,792 Lot (sqft)
    Listed with Marshall Kozak, LLC.
  19. Photo of 47 W Main St, Merrimac, MA 01860 (MLS # 73205735)
    $699,000
    Photo of 47 W Main St, Merrimac, MA 01860 (MLS # 73205735)
    Photo of 47 W Main St, Merrimac, MA 01860 (MLS # 73205735)
    47 W Main St, Merrimac, MA
    47 W Main St
    Merrimac, MA
    • 5 Beds
    • 3 Baths
    • 2,637 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
    Listed with Cameron Real Estate Group
  20. Photo of 211 N. Main Street, Sharon, MA 02067 (MLS # 73205733)
    $624,900
    Photo of 211 N. Main Street, Sharon, MA 02067 (MLS # 73205733)
    Photo of 211 N. Main Street, Sharon, MA 02067 (MLS # 73205733)
    211 N. Main Street, Sharon, MA
    211 N. Main Street
    Sharon, MA
    • 3 Beds
    • 1 Bath
    • 1,312 Home (sqft)
    • 1 Bath
    • 28,750 Lot (sqft)
    Listed with Keller Williams Elite
  21. Photo of 312 Water St #34, Lawrence, MA 01841 (MLS # 73205729)
    $249,900
    Photo of 312 Water St #34, Lawrence, MA 01841 (MLS # 73205729)
    Photo of 312 Water St #34, Lawrence, MA 01841 (MLS # 73205729)
    312 Water St #34, Lawrence, MA
    312 Water St #34
    Lawrence, MA
    • 2 Beds
    • 1 Bath
    • 932 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Beni Maison Realty, Inc.
  22. Photo of 401 Cedar Avenue, Swansea, MA 02777 (MLS # 73205727)
    $1,545,000
    Photo of 401 Cedar Avenue, Swansea, MA 02777 (MLS # 73205727)
    Photo of 401 Cedar Avenue, Swansea, MA 02777 (MLS # 73205727)
    42
     
    401 Cedar Avenue, Swansea, MA
    401 Cedar Avenue
    Swansea, MA
    • 4 Beds
    • 6 Baths
    • 6,183 Home (sqft)
    • 6 Baths
    • 6.39 Lot (ac)
    Listed with Mott & Chace Sotheby's International Realty
  23. Photo of 20 Meetinghouse Hill Rd, Sterling, MA 01564 (MLS # 73205716)
    $450,000
    Photo of 20 Meetinghouse Hill Rd, Sterling, MA 01564 (MLS # 73205716)
    Photo of 20 Meetinghouse Hill Rd, Sterling, MA 01564 (MLS # 73205716)
    16
     
    20 Meetinghouse Hill Rd, Sterling, MA
    20 Meetinghouse Hill Rd
    Sterling, MA
    • 3 Beds
    • 1 Bath
    • 1,022 Home (sqft)
    • 1 Bath
    • 12,633 Lot (sqft)
    Listed with Century 21 Center Home Team
  24. Photo of 5 Sachem St #3, Boston, MA 02120 (MLS # 73205718)
    $885,000
    Photo of 5 Sachem St #3, Boston, MA 02120 (MLS # 73205718)
    Photo of 5 Sachem St #3, Boston, MA 02120 (MLS # 73205718)
    22
     
    5 Sachem St #3, Boston, MA
    5 Sachem St #3
    Boston, MA
    • 6 Beds
    • 2 Baths
    • 2,205 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Boston Property Services, LLC
  25. Photo of 16062 Ashburnham Hill Rd, Fitchburg, MA 01420 (MLS # 73205724)
    $420,000
    Photo of 16062 Ashburnham Hill Rd, Fitchburg, MA 01420 (MLS # 73205724)
    Photo of 16062 Ashburnham Hill Rd, Fitchburg, MA 01420 (MLS # 73205724)
    38
     
    16062 Ashburnham Hill Rd, Fitchburg, MA
    16062 Ashburnham Hill Rd
    Fitchburg, MA
    • 4 Beds
    • 2 Baths
    • 2,320 Home (sqft)
    • 2 Baths
    • 10,019 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  26. Photo of 645 Robbins Ave #55, Dracut, MA 01826 (MLS # 73205719)
    $350,000
    Photo of 645 Robbins Ave #55, Dracut, MA 01826 (MLS # 73205719)
    Photo of 645 Robbins Ave #55, Dracut, MA 01826 (MLS # 73205719)
    645 Robbins Ave #55, Dracut, MA
    645 Robbins Ave #55
    Dracut, MA
    • 2 Beds
    • 1 Bath
    • 1,044 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Realty Professionals
  27. Photo of 68 Charlesview St, Boston, MA 02135 (MLS # 73205723)
    $1,749,000
    Photo of 68 Charlesview St, Boston, MA 02135 (MLS # 73205723)
    Photo of 68 Charlesview St, Boston, MA 02135 (MLS # 73205723)
    37
     
    68 Charlesview St, Boston, MA
    68 Charlesview St
    Boston, MA
    • 6 Beds
    • 3 Baths
    • 3,840 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
    Listed with Coldwell Banker Realty - Newton
  28. Photo of 152154 Liberty St, Rockland, MA 02370 (MLS # 73204433)
    $425,000
    Photo of 152154 Liberty St, Rockland, MA 02370 (MLS # 73204433)
    Photo of 152154 Liberty St, Rockland, MA 02370 (MLS # 73204433)
    13
     
    152154 Liberty St, Rockland, MA
    152154 Liberty St
    Rockland, MA
    • 4 Beds
    • 2 Baths
    • 1,218 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
    Listed with Invest Realty Group
  29. Photo of 137139 Deane St, New Bedford, MA 02740 (MLS # 73205720)
    $589,900
    Photo of 137139 Deane St, New Bedford, MA 02740 (MLS # 73205720)
    Photo of 137139 Deane St, New Bedford, MA 02740 (MLS # 73205720)
    137139 Deane St, New Bedford, MA
    137139 Deane St
    New Bedford, MA
    • 9 Beds
    • 3 Baths
    • 4,422 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
    Listed with HomeSmart Professionals Real Estate
  30. Photo of 251 Prospect Street, Lawrence, MA 01841 (MLS # 73205717)
    $454,900
    Photo of 251 Prospect Street, Lawrence, MA 01841 (MLS # 73205717)
    Photo of 251 Prospect Street, Lawrence, MA 01841 (MLS # 73205717)
    33
     
    251 Prospect Street, Lawrence, MA
    251 Prospect Street
    Lawrence, MA
    • 4 Beds
    • 3 Baths
    • 1,680 Home (sqft)
    • 3 Baths
    • 6,099 Lot (sqft)
    Listed with Empire Real Estateâ„¢
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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

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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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