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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 4/28/2024)

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  1. Photo of 20 Boxwood Dr, Barnstable, MA 02668 (MLS # 73227531)
    $579,000
    Photo of 20 Boxwood Dr, Barnstable, MA 02668 (MLS # 73227531)
    Photo of 20 Boxwood Dr, Barnstable, MA 02668 (MLS # 73227531)
    16
     
    20 Boxwood Dr, Barnstable, MA
    20 Boxwood Dr
    Barnstable, MA
    • 3 Beds
    • 2 Baths
    • 1,190 Home (sqft)
    • 2 Baths
    • 16,553 Lot (sqft)
    Listed with LAER Realty Partners
  2. Photo of 12 Liberty St, Southbridge, MA 01550 (MLS # 73224390)
    $300,000
    Photo of 12 Liberty St, Southbridge, MA 01550 (MLS # 73224390)
    Photo of 12 Liberty St, Southbridge, MA 01550 (MLS # 73224390)
    22
     
    12 Liberty St, Southbridge, MA
    12 Liberty St
    Southbridge, MA
    • 4 Beds
    • 2 Baths
    • 1,440 Home (sqft)
    • 2 Baths
    • 37,462 Lot (sqft)
    Listed with Real Estate Exchange
  3. Photo of 577 Podunk Rd, East Brookfield, MA 01515 (MLS # 73226536)
    $525,000
    Photo of 577 Podunk Rd, East Brookfield, MA 01515 (MLS # 73226536)
    Photo of 577 Podunk Rd, East Brookfield, MA 01515 (MLS # 73226536)
    42
     
    577 Podunk Rd, East Brookfield, MA
    577 Podunk Rd
    East Brookfield, MA
    • 3 Beds
    • 3 Baths
    • 1,933 Home (sqft)
    • 3 Baths
    • 5.03 Lot (ac)
    Listed with MA Homes, LLC
  4. Photo of 1 Beach Ter, Woburn, MA 01801 (MLS # 73229704)
    $799,900
    Photo of 1 Beach Ter, Woburn, MA 01801 (MLS # 73229704)
    Photo of 1 Beach Ter, Woburn, MA 01801 (MLS # 73229704)
    38
     
    1 Beach Ter, Woburn, MA
    1 Beach Ter
    Woburn, MA
    • 4 Beds
    • 4 Baths
    • 2,424 Home (sqft)
    • 4 Baths
    • 12,197 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  5. Photo of 191 E Spring Street, Avon, MA 02322 (MLS # 73229628)
    $525,000
    Photo of 191 E Spring Street, Avon, MA 02322 (MLS # 73229628)
    Photo of 191 E Spring Street, Avon, MA 02322 (MLS # 73229628)
    191 E Spring Street, Avon, MA
    191 E Spring Street
    Avon, MA
    • 3 Beds
    • 1 Bath
    • 1,398 Home (sqft)
    • 1 Bath
    • 1.50 Lot (ac)
    Listed with Century 21 Marella Realty
  6. Photo of 210 Brook Village Rd #20, Nashua, NH 03062 (MLS # 73229550)
    $289,900
    Photo of 210 Brook Village Rd #20, Nashua, NH 03062 (MLS # 73229550)
    Photo of 210 Brook Village Rd #20, Nashua, NH 03062 (MLS # 73229550)
    12
     
    210 Brook Village Rd #20, Nashua, NH
    210 Brook Village Rd #20
    Nashua, NH
    • 2 Beds
    • 1 Bath
    • 980 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Greatland Real Estate LLC
  7. Photo of 110 Pasadena St, Springfield, MA 01108 (MLS # 73229548)
    $470,000
    Photo of 110 Pasadena St, Springfield, MA 01108 (MLS # 73229548)
    Photo of 110 Pasadena St, Springfield, MA 01108 (MLS # 73229548)
    14
     
    110 Pasadena St, Springfield, MA
    110 Pasadena St
    Springfield, MA
    • 8 Beds
    • 4 Baths
    • 4,968 Home (sqft)
    • 4 Baths
    • 7,406 Lot (sqft)
    Listed with Naples Realty Group
  8. Photo of 8 Priscilla Ln, Quincy, MA 02169 (MLS # 73229546)
    $799,900
    Photo of 8 Priscilla Ln, Quincy, MA 02169 (MLS # 73229546)
    Photo of 8 Priscilla Ln, Quincy, MA 02169 (MLS # 73229546)
    32
     
    8 Priscilla Ln, Quincy, MA
    8 Priscilla Ln
    Quincy, MA
    • 3 Beds
    • 2 Baths
    • 1,488 Home (sqft)
    • 2 Baths
    • 6,534 Lot (sqft)
    Listed with Success! Real Estate
  9. Photo of 224 Bartholomew St, Peabody, MA 01960 (MLS # 73229540)
    $929,900
    Photo of 224 Bartholomew St, Peabody, MA 01960 (MLS # 73229540)
    Photo of 224 Bartholomew St, Peabody, MA 01960 (MLS # 73229540)
    41
     
    224 Bartholomew St, Peabody, MA
    224 Bartholomew St
    Peabody, MA
    • 3 Beds
    • 3 Baths
    • 2,444 Home (sqft)
    • 3 Baths
    • 14,375 Lot (sqft)
    Listed with Keller Williams Realty Evolution
  10. Photo of 81 Richview Ave, South Hadley, MA 01075 (MLS # 73229537)
    $339,900
    Photo of 81 Richview Ave, South Hadley, MA 01075 (MLS # 73229537)
    Photo of 81 Richview Ave, South Hadley, MA 01075 (MLS # 73229537)
    42
     
    81 Richview Ave, South Hadley, MA
    81 Richview Ave
    South Hadley, MA
    • 3 Beds
    • 2 Baths
    • 1,060 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
    Listed with Real Broker MA, LLC
  11. Photo of 122 French Ave, Brockton, MA 02301 (MLS # 73229536)
    $795,500
    Photo of 122 French Ave, Brockton, MA 02301 (MLS # 73229536)
    Photo of 122 French Ave, Brockton, MA 02301 (MLS # 73229536)
    21
     
    122 French Ave, Brockton, MA
    122 French Ave
    Brockton, MA
    • 5 Beds
    • 3 Baths
    • 2,518 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
    Listed with Collier Cacciola Real Estate, LLC
  12. Photo of 11 Hills View, Milton, MA 02186 (MLS # 73229534)
    $939,000
    Photo of 11 Hills View, Milton, MA 02186 (MLS # 73229534)
    Photo of 11 Hills View, Milton, MA 02186 (MLS # 73229534)
    17
     
    11 Hills View, Milton, MA
    11 Hills View
    Milton, MA
    • 4 Beds
    • 5 Baths
    • 2,530 Home (sqft)
    • 5 Baths
    • 18,296 Lot (sqft)
    Listed with Keller Williams Realty Boston Northwest
  13. Photo of 49 Lexington St, Boston, MA 02128 (MLS # 73229532)
    $900,000
    Photo of 49 Lexington St, Boston, MA 02128 (MLS # 73229532)
    Photo of 49 Lexington St, Boston, MA 02128 (MLS # 73229532)
    49 Lexington St, Boston, MA
    49 Lexington St
    Boston, MA
    • 3 Beds
    • 3 Baths
    • 2,043 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
    Listed with Arthur L. Bowen
  14. Photo of 47 Lexington St, Boston, MA 02128 (MLS # 73229528)
    $900,000
    Photo of 47 Lexington St, Boston, MA 02128 (MLS # 73229528)
    Photo of 47 Lexington St, Boston, MA 02128 (MLS # 73229528)
    47 Lexington St, Boston, MA
    47 Lexington St
    Boston, MA
    • 5 Beds
    • 3 Baths
    • 2,043 Home (sqft)
    • 3 Baths
    • 1,307 Lot (sqft)
    Listed with Arthur L. Bowen
  15. Photo of 305 Webster Ave #107, Cambridge, MA 02141 (MLS # 73229529)
    $749,800
    Photo of 305 Webster Ave #107, Cambridge, MA 02141 (MLS # 73229529)
    Photo of 305 Webster Ave #107, Cambridge, MA 02141 (MLS # 73229529)
    15
     
    305 Webster Ave #107, Cambridge, MA
    305 Webster Ave #107
    Cambridge, MA
    • 1 Bed
    • 1 Bath
    • 795 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Compass
  16. Photo of 105 Winnacunnet Road #16, Hampton, NH 03842 (MLS # 73229527)
    $350,000
    Photo of 105 Winnacunnet Road #16, Hampton, NH 03842 (MLS # 73229527)
    Photo of 105 Winnacunnet Road #16, Hampton, NH 03842 (MLS # 73229527)
    39
     
    105 Winnacunnet Road #16, Hampton, NH
    105 Winnacunnet Road #16
    Hampton, NH
    • 1 Bed
    • 2 Baths
    • 1,014 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Cameron Prestige - Amesbury
  17. Photo of 134 Millers Lane, Somerset, MA 02726 (MLS # 73229523)
    $576,000
    Photo of 134 Millers Lane, Somerset, MA 02726 (MLS # 73229523)
    Photo of 134 Millers Lane, Somerset, MA 02726 (MLS # 73229523)
    36
     
    134 Millers Lane, Somerset, MA
    134 Millers Lane
    Somerset, MA
    • 3 Beds
    • 2 Baths
    • 2,364 Home (sqft)
    • 2 Baths
    • 23,087 Lot (sqft)
    Listed with JT Realty Group LLC
  18. Photo of 323 Bacon St #323, Natick, MA 01760 (MLS # 73229522)
    $689,900
    Photo of 323 Bacon St #323, Natick, MA 01760 (MLS # 73229522)
    Photo of 323 Bacon St #323, Natick, MA 01760 (MLS # 73229522)
    19
     
    323 Bacon St #323, Natick, MA
    323 Bacon St #323
    Natick, MA
    • 3 Beds
    • 2 Baths
    • 1,600 Home (sqft)
    • 2 Baths
    • 13,504 Lot (sqft)
    Listed with Compass
  19. Photo of 54 Fountain Ln #6, Weymouth, MA 02190 (MLS # 73229521)
    $349,900
    Photo of 54 Fountain Ln #6, Weymouth, MA 02190 (MLS # 73229521)
    Photo of 54 Fountain Ln #6, Weymouth, MA 02190 (MLS # 73229521)
    13
     
    54 Fountain Ln #6, Weymouth, MA
    54 Fountain Ln #6
    Weymouth, MA
    • 2 Beds
    • 1 Bath
    • 933 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  20. Photo of 163 2nd St West St, Boston, MA 02127 (MLS # 73229520)
    $1,395,000
    Photo of 163 2nd St West St, Boston, MA 02127 (MLS # 73229520)
    Photo of 163 2nd St West St, Boston, MA 02127 (MLS # 73229520)
    19
     
    163 2nd St West St, Boston, MA
    163 2nd St West St
    Boston, MA
    • 3 Beds
    • 4 Baths
    • 1,671 Home (sqft)
    • 4 Baths
    • 1,743 Lot (sqft)
    Listed with Captivating Realty
  21. Photo of 335 Crawford St, Northborough, MA 01532 (MLS # 73229514)
    $1,250,000
    Photo of 335 Crawford St, Northborough, MA 01532 (MLS # 73229514)
    Photo of 335 Crawford St, Northborough, MA 01532 (MLS # 73229514)
    42
     
    335 Crawford St, Northborough, MA
    335 Crawford St
    Northborough, MA
    • 3 Beds
    • 3 Baths
    • 3,715 Home (sqft)
    • 3 Baths
    • 4.00 Lot (ac)
    Listed with Andrew J. Abu Inc., REALTORS®
  22. Photo of 27 Morse Ave, Attleboro, MA 02703 (MLS # 73229511)
    $829,000
    Photo of 27 Morse Ave, Attleboro, MA 02703 (MLS # 73229511)
    Photo of 27 Morse Ave, Attleboro, MA 02703 (MLS # 73229511)
    13
     
    27 Morse Ave, Attleboro, MA
    27 Morse Ave
    Attleboro, MA
    • 4 Beds
    • 3 Baths
    • 2,700 Home (sqft)
    • 3 Baths
    • 21,780 Lot (sqft)
    Listed with eXp Realty
  23. Photo of 4 Clipper Rd #4, Plymouth, MA 02360 (MLS # 73229504)
    $819,000
    Photo of 4 Clipper Rd #4, Plymouth, MA 02360 (MLS # 73229504)
    Photo of 4 Clipper Rd #4, Plymouth, MA 02360 (MLS # 73229504)
    40
     
    4 Clipper Rd #4, Plymouth, MA
    4 Clipper Rd #4
    Plymouth, MA
    • 2 Beds
    • 4 Baths
    • 1,901 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with Thorndike Development
  24. Photo of 312 Water St #27, Lawrence, MA 01841 (MLS # 73229495)
    $285,000
    Photo of 312 Water St #27, Lawrence, MA 01841 (MLS # 73229495)
    Photo of 312 Water St #27, Lawrence, MA 01841 (MLS # 73229495)
    26
     
    312 Water St #27, Lawrence, MA
    312 Water St #27
    Lawrence, MA
    • 2 Beds
    • 2 Baths
    • 988 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Realty Evolution
  25. Photo of 265 County St, Rehoboth, MA 02769 (MLS # 73229493)
    $650,000
    Photo of 265 County St, Rehoboth, MA 02769 (MLS # 73229493)
    Photo of 265 County St, Rehoboth, MA 02769 (MLS # 73229493)
    42
     
    265 County St, Rehoboth, MA
    265 County St
    Rehoboth, MA
    • 3 Beds
    • 2 Baths
    • 1,692 Home (sqft)
    • 2 Baths
    • 3.83 Lot (ac)
    Listed with Bay Market Real Estate
  26. Photo of 1239 Main Street #365B, Tewksbury, MA 01876 (MLS # 73229497)
    $329,900
    Photo of 1239 Main Street #365B, Tewksbury, MA 01876 (MLS # 73229497)
    Photo of 1239 Main Street #365B, Tewksbury, MA 01876 (MLS # 73229497)
    24
     
    1239 Main Street #365B, Tewksbury, MA
    1239 Main Street #365B
    Tewksbury, MA
    • 2 Beds
    • 1 Bath
    • 960 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Chelmsford
  27. Photo of 31 Blake St, Revere, MA 02151 (MLS # 73229492)
    $749,723
    Photo of 31 Blake St, Revere, MA 02151 (MLS # 73229492)
    Photo of 31 Blake St, Revere, MA 02151 (MLS # 73229492)
    23
     
    31 Blake St, Revere, MA
    31 Blake St
    Revere, MA
    • 4 Beds
    • 3 Baths
    • 2,127 Home (sqft)
    • 3 Baths
    • 3,050 Lot (sqft)
    Listed with Tremont Realty Group, LLC
  28. Photo of 4 Hyde St, Brookfield, MA 01506 (MLS # 73229490)
    $339,000
    Photo of 4 Hyde St, Brookfield, MA 01506 (MLS # 73229490)
    Photo of 4 Hyde St, Brookfield, MA 01506 (MLS # 73229490)
    42
     
    4 Hyde St, Brookfield, MA
    4 Hyde St
    Brookfield, MA
    • 3 Beds
    • 2 Baths
    • 1,354 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
    Listed with Century 21 North East
  29. Photo of 2325 Elizabeth St, Northampton, MA 01060 (MLS # 73229491)
    $499,000
    Photo of 2325 Elizabeth St, Northampton, MA 01060 (MLS # 73229491)
    Photo of 2325 Elizabeth St, Northampton, MA 01060 (MLS # 73229491)
    23
     
    2325 Elizabeth St, Northampton, MA
    2325 Elizabeth St
    Northampton, MA
    • 4 Beds
    • 2 Baths
    • 2,318 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
    Listed with 5 College REALTORS®
  30. Photo of 224 Old Westport Rd, Dartmouth, MA 02747 (MLS # 73229482)
    $925,000
    Photo of 224 Old Westport Rd, Dartmouth, MA 02747 (MLS # 73229482)
    Photo of 224 Old Westport Rd, Dartmouth, MA 02747 (MLS # 73229482)
    31
     
    224 Old Westport Rd, Dartmouth, MA
    224 Old Westport Rd
    Dartmouth, MA
    • 4 Beds
    • 5 Baths
    • 3,615 Home (sqft)
    • 5 Baths
    • 1.03 Lot (ac)
    Listed with Milbury and Company
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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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