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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 5/13/2024)

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  1. Photo of 8 Lake Street, Norfolk, MA 02056 (MLS # 73236937)
    $899,000
    Photo of 8 Lake Street, Norfolk, MA 02056 (MLS # 73236937)
    Photo of 8 Lake Street, Norfolk, MA 02056 (MLS # 73236937)
    40
     
    8 Lake Street, Norfolk, MA
    8 Lake Street
    Norfolk, MA
    • 3 Beds
    • 3 Baths
    • 3,060 Home (sqft)
    • 3 Baths
    • 30,928 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  2. Photo of 18 Pine Ridge Drive, Ayer, MA 01432 (MLS # 73236911)
    $479,900
    Photo of 18 Pine Ridge Drive, Ayer, MA 01432 (MLS # 73236911)
    Photo of 18 Pine Ridge Drive, Ayer, MA 01432 (MLS # 73236911)
    15
     
    18 Pine Ridge Drive, Ayer, MA
    18 Pine Ridge Drive
    Ayer, MA
    • 3 Beds
    • 1 Bath
    • 1,056 Home (sqft)
    • 1 Bath
    • 13,068 Lot (sqft)
    Listed with Foster-Healey Real Estate
  3. Photo of 11 (Lt 45) Darrell Drive, Littleton, MA 01460 (MLS # 73236900)
    $1,260,000
    Photo of 11 (Lt 45) Darrell Drive, Littleton, MA 01460 (MLS # 73236900)
    Photo of 11 (Lt 45) Darrell Drive, Littleton, MA 01460 (MLS # 73236900)
    11 (Lt 45) Darrell Drive, Littleton, MA
    11 (Lt 45) Darrell Drive
    Littleton, MA
    • 4 Beds
    • 3 Baths
    • 3,046 Home (sqft)
    • 3 Baths
    • 21,780 Lot (sqft)
    Listed with Westford Real Estate, Inc.
  4. Photo of 281 Riverlin Street, Millbury, MA 01527 (MLS # 73236896)
    $275,000
    Photo of 281 Riverlin Street, Millbury, MA 01527 (MLS # 73236896)
    Photo of 281 Riverlin Street, Millbury, MA 01527 (MLS # 73236896)
    281 Riverlin Street, Millbury, MA
    281 Riverlin Street
    Millbury, MA
    • 2 Beds
    • 2 Baths
    • 1,162 Home (sqft)
    • 2 Baths
    • 24,830 Lot (sqft)
    Listed with LAER Realty Partners
  5. Photo of 80 South St #5, Fitchburg, MA 01420 (MLS # 73236899)
    $349,900
    Photo of 80 South St #5, Fitchburg, MA 01420 (MLS # 73236899)
    Photo of 80 South St #5, Fitchburg, MA 01420 (MLS # 73236899)
    28
     
    80 South St #5, Fitchburg, MA
    80 South St #5
    Fitchburg, MA
    • 2 Beds
    • 2 Baths
    • 881 Home (sqft)
    • 2 Baths
    • 31,799 Lot (sqft)
    Listed with Coldwell Banker Realty - Leominster
  6. Photo of 33 Colony Rd #1A, West Springfield, MA 01089 (MLS # 73236901)
    $130,000
    Photo of 33 Colony Rd #1A, West Springfield, MA 01089 (MLS # 73236901)
    Photo of 33 Colony Rd #1A, West Springfield, MA 01089 (MLS # 73236901)
    12
     
    33 Colony Rd #1A, West Springfield, MA
    33 Colony Rd #1A
    West Springfield, MA
    • 2 Beds
    • 1 Bath
    • 541 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with RE/MAX Connections
  7. Photo of 35 Eldridge Rd #210, Boston, MA 02130 (MLS # 73236893)
    $575,000
    Photo of 35 Eldridge Rd #210, Boston, MA 02130 (MLS # 73236893)
    Photo of 35 Eldridge Rd #210, Boston, MA 02130 (MLS # 73236893)
    22
     
    35 Eldridge Rd #210, Boston, MA
    35 Eldridge Rd #210
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 980 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with eXp Realty
  8. Photo of 80 Hamblen Farm Road, Wellfleet, MA 02667 (MLS # 73236891)
    $749,000
    Photo of 80 Hamblen Farm Road, Wellfleet, MA 02667 (MLS # 73236891)
    Photo of 80 Hamblen Farm Road, Wellfleet, MA 02667 (MLS # 73236891)
    40
     
    80 Hamblen Farm Road, Wellfleet, MA
    80 Hamblen Farm Road
    Wellfleet, MA
    • 3 Beds
    • 1 Bath
    • 1,770 Home (sqft)
    • 1 Bath
    • 16,118 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  9. Photo of 265 Loudville Rd, Easthampton, MA 01027 (MLS # 73236883)
    $329,900
    Photo of 265 Loudville Rd, Easthampton, MA 01027 (MLS # 73236883)
    Photo of 265 Loudville Rd, Easthampton, MA 01027 (MLS # 73236883)
    36
     
    265 Loudville Rd, Easthampton, MA
    265 Loudville Rd
    Easthampton, MA
    • 3 Beds
    • 1 Bath
    • 1,760 Home (sqft)
    • 1 Bath
    • 1.40 Lot (ac)
    Listed with 5 College REALTORS® Northampton
  10. Photo of 582 Revere St #7, Revere, MA 02151 (MLS # 73236882)
    $510,000
    Photo of 582 Revere St #7, Revere, MA 02151 (MLS # 73236882)
    Photo of 582 Revere St #7, Revere, MA 02151 (MLS # 73236882)
    19
     
    582 Revere St #7, Revere, MA
    582 Revere St #7
    Revere, MA
    • 2 Beds
    • 2 Baths
    • 1,652 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Yuan's Team Realty
  11. Photo of 21 Linscott Rd, Hingham, MA 02043 (MLS # 73236875)
    $889,000
    Photo of 21 Linscott Rd, Hingham, MA 02043 (MLS # 73236875)
    Photo of 21 Linscott Rd, Hingham, MA 02043 (MLS # 73236875)
    32
     
    21 Linscott Rd, Hingham, MA
    21 Linscott Rd
    Hingham, MA
    • 3 Beds
    • 2 Baths
    • 1,984 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  12. Photo of 12 Proctor Street, Manchester, MA 01944 (MLS # 73236877)
    $3,800,000
    Photo of 12 Proctor Street, Manchester, MA 01944 (MLS # 73236877)
    Photo of 12 Proctor Street, Manchester, MA 01944 (MLS # 73236877)
    40
     
    12 Proctor Street, Manchester, MA
    12 Proctor Street
    Manchester, MA
    • 6 Beds
    • 5 Baths
    • 5,836 Home (sqft)
    • 5 Baths
    • 1.44 Lot (ac)
    Listed with J. Barrett & Company
  13. Photo of 33 Walton St, Chicopee, MA 01013 (MLS # 73236027)
    $229,900
    Photo of 33 Walton St, Chicopee, MA 01013 (MLS # 73236027)
    Photo of 33 Walton St, Chicopee, MA 01013 (MLS # 73236027)
    25
     
    33 Walton St, Chicopee, MA
    33 Walton St
    Chicopee, MA
    • 3 Beds
    • 1 Bath
    • 980 Home (sqft)
    • 1 Bath
    • 6,099 Lot (sqft)
    Listed with Executive Real Estate, Inc.
  14. Photo of 474 Kathleen Ave, Somerset, MA 02725 (MLS # 73236876)
    $469,000
    Photo of 474 Kathleen Ave, Somerset, MA 02725 (MLS # 73236876)
    Photo of 474 Kathleen Ave, Somerset, MA 02725 (MLS # 73236876)
    41
     
    474 Kathleen Ave, Somerset, MA
    474 Kathleen Ave
    Somerset, MA
    • 4 Beds
    • 2 Baths
    • 1,472 Home (sqft)
    • 2 Baths
    • 11,762 Lot (sqft)
    Listed with Residential Properties Ltd
  15. Photo of 21 Hampshire Road #412, Methuen, MA 01844 (MLS # 73236881)
    $289,999
    Photo of 21 Hampshire Road #412, Methuen, MA 01844 (MLS # 73236881)
    Photo of 21 Hampshire Road #412, Methuen, MA 01844 (MLS # 73236881)
    26
     
    21 Hampshire Road #412, Methuen, MA
    21 Hampshire Road #412
    Methuen, MA
    • 1 Bed
    • 1 Bath
    • 750 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Lamacchia Realty, Inc
  16. Photo of 27 Armandine St #2, Boston, MA 02124 (MLS # 73236868)
    $535,000
    Photo of 27 Armandine St #2, Boston, MA 02124 (MLS # 73236868)
    Photo of 27 Armandine St #2, Boston, MA 02124 (MLS # 73236868)
    19
     
    27 Armandine St #2, Boston, MA
    27 Armandine St #2
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 878 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  17. Photo of 3 Idlewile Lane, Weston, MA 02493 (MLS # 73236867)
    $15,000,000
    Photo of 3 Idlewile Lane, Weston, MA 02493 (MLS # 73236867)
    Photo of 3 Idlewile Lane, Weston, MA 02493 (MLS # 73236867)
    41
     
    3 Idlewile Lane, Weston, MA
    3 Idlewile Lane
    Weston, MA
    • 6 Beds
    • 11 Baths
    • 14,620 Home (sqft)
    • 11 Baths
    • 8.27 Lot (ac)
    Listed with Coldwell Banker Realty - Brookline
  18. Photo of 17 Kilbourn Rd #6, Lancaster, MA 01523 (MLS # 73236865)
    $360,000
    Photo of 17 Kilbourn Rd #6, Lancaster, MA 01523 (MLS # 73236865)
    Photo of 17 Kilbourn Rd #6, Lancaster, MA 01523 (MLS # 73236865)
    37
     
    17 Kilbourn Rd #6, Lancaster, MA
    17 Kilbourn Rd #6
    Lancaster, MA
    • 2 Beds
    • 2 Baths
    • 1,092 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Worcester
  19. Photo of 18 Elm Street, Acton, MA 01720 (MLS # 73236857)
    $939,000
    Photo of 18 Elm Street, Acton, MA 01720 (MLS # 73236857)
    Photo of 18 Elm Street, Acton, MA 01720 (MLS # 73236857)
    23
     
    18 Elm Street, Acton, MA
    18 Elm Street
    Acton, MA
    • 4 Beds
    • 4 Baths
    • 2,602 Home (sqft)
    • 4 Baths
    • 15,682 Lot (sqft)
    Listed with The Attias Group, LLC
  20. Photo of 30 Walnut St, Millis, MA 02054 (MLS # 73236864)
    $879,000
    Photo of 30 Walnut St, Millis, MA 02054 (MLS # 73236864)
    Photo of 30 Walnut St, Millis, MA 02054 (MLS # 73236864)
    30
     
    30 Walnut St, Millis, MA
    30 Walnut St
    Millis, MA
    • 4 Beds
    • 3 Baths
    • 2,324 Home (sqft)
    • 3 Baths
    • 33,542 Lot (sqft)
    Listed with Boston Realty Net
  21. Photo of 23 Baycrest Road, Ipswich, MA 01938 (MLS # 73236852)
    $825,000
    Photo of 23 Baycrest Road, Ipswich, MA 01938 (MLS # 73236852)
    Photo of 23 Baycrest Road, Ipswich, MA 01938 (MLS # 73236852)
    28
     
    23 Baycrest Road, Ipswich, MA
    23 Baycrest Road
    Ipswich, MA
    • 2 Beds
    • 1 Bath
    • 840 Home (sqft)
    • 1 Bath
    • 3,050 Lot (sqft)
    Listed with eXp Realty
  22. Photo of 267 Old Colony Ave #204, Boston, MA 02127 (MLS # 73236859)
    $699,000
    Photo of 267 Old Colony Ave #204, Boston, MA 02127 (MLS # 73236859)
    Photo of 267 Old Colony Ave #204, Boston, MA 02127 (MLS # 73236859)
    267 Old Colony Ave #204, Boston, MA
    267 Old Colony Ave #204
    Boston, MA
    • 1 Bed
    • 1 Bath
    • 745 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  23. Photo of 104 Western Ave, Weymouth, MA 02188 (MLS # 73236849)
    $829,900
    Photo of 104 Western Ave, Weymouth, MA 02188 (MLS # 73236849)
    Photo of 104 Western Ave, Weymouth, MA 02188 (MLS # 73236849)
    30
     
    104 Western Ave, Weymouth, MA
    104 Western Ave
    Weymouth, MA
    • 3 Beds
    • 2 Baths
    • 1,776 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
    Listed with Keller Williams Realty
  24. Photo of 267 Old Colony Ave #202, Boston, MA 02127 (MLS # 73236855)
    $799,000
    Photo of 267 Old Colony Ave #202, Boston, MA 02127 (MLS # 73236855)
    Photo of 267 Old Colony Ave #202, Boston, MA 02127 (MLS # 73236855)
    267 Old Colony Ave #202, Boston, MA
    267 Old Colony Ave #202
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 855 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  25. Photo of 85 Jones Road, Revere, MA 02151 (MLS # 73236850)
    $299,900
    Photo of 85 Jones Road, Revere, MA 02151 (MLS # 73236850)
    Photo of 85 Jones Road, Revere, MA 02151 (MLS # 73236850)
    85 Jones Road, Revere, MA
    85 Jones Road
    Revere, MA
    • 2 Beds
    • 1 Bath
    • 1,320 Home (sqft)
    • 1 Bath
    • 3,050 Lot (sqft)
    Listed with Century 21 North East
  26. Photo of 21 Ruggles Ct, Palmer, MA 01080 (MLS # 73230498)
    $279,000
    Photo of 21 Ruggles Ct, Palmer, MA 01080 (MLS # 73230498)
    Photo of 21 Ruggles Ct, Palmer, MA 01080 (MLS # 73230498)
    34
     
    21 Ruggles Ct, Palmer, MA
    21 Ruggles Ct
    Palmer, MA
    • 2 Beds
    • 1 Bath
    • 1,266 Home (sqft)
    • 1 Bath
    • 6,970 Lot (sqft)
    Listed with Brenda Cuoco & Associates Real Estate Brokerage
  27. Photo of 1731 Beacon Street #217, Brookline, MA 02445 (MLS # 73236844)
    $899,000
    Photo of 1731 Beacon Street #217, Brookline, MA 02445 (MLS # 73236844)
    Photo of 1731 Beacon Street #217, Brookline, MA 02445 (MLS # 73236844)
    33
     
    1731 Beacon Street #217, Brookline, MA
    1731 Beacon Street #217
    Brookline, MA
    • 2 Beds
    • 2 Baths
    • 1,218 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Compass
  28. Photo of 81 Leonard Cir, Lowell, MA 01854 (MLS # 73236845)
    $545,000
    Photo of 81 Leonard Cir, Lowell, MA 01854 (MLS # 73236845)
    Photo of 81 Leonard Cir, Lowell, MA 01854 (MLS # 73236845)
    40
     
    81 Leonard Cir, Lowell, MA
    81 Leonard Cir
    Lowell, MA
    • 3 Beds
    • 2 Baths
    • 1,632 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
    Listed with Coldwell Banker Realty - Chelmsford
  29. Photo of 78 Halfway Pond Rd, Plymouth, MA 02360 (MLS # 73236390)
    $875,000
    Photo of 78 Halfway Pond Rd, Plymouth, MA 02360 (MLS # 73236390)
    Photo of 78 Halfway Pond Rd, Plymouth, MA 02360 (MLS # 73236390)
    38
     
    78 Halfway Pond Rd, Plymouth, MA
    78 Halfway Pond Rd
    Plymouth, MA
    • 3 Beds
    • 3 Baths
    • 3,573 Home (sqft)
    • 3 Baths
    • 8.02 Lot (ac)
    Listed with Options 153, Mullen & Partners
  30. Photo of 730 Brush Hill Rd, Milton, MA 02186 (MLS # 73236840)
    $2,390,000
    Photo of 730 Brush Hill Rd, Milton, MA 02186 (MLS # 73236840)
    Photo of 730 Brush Hill Rd, Milton, MA 02186 (MLS # 73236840)
    34
     
    730 Brush Hill Rd, Milton, MA
    730 Brush Hill Rd
    Milton, MA
    • 4 Beds
    • 4 Baths
    • 3,982 Home (sqft)
    • 4 Baths
    • 2.05 Lot (ac)
    Listed with William Raveis R.E. & Home Services
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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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