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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 7/11/2025)

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  1. Photo of 72 River Rd, Barnstable, MA 02648 (MLS # 73403346)
    $1,895,000
    Photo of 72 River Rd, Barnstable, MA 02648 (MLS # 73403346)
    Photo of 72 River Rd, Barnstable, MA 02648 (MLS # 73403346)
    40
     
    72 River Rd, Barnstable, MA
    72 River Rd
    Barnstable, MA
    • 4 Beds
    • 5 Baths
    • 3,356 Home (sqft)
    • 5 Baths
    • 43,125 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  2. Photo of 100 Burbank Ave, Warren, MA 01083 (MLS # 73403349)
    $399,000
    Photo of 100 Burbank Ave, Warren, MA 01083 (MLS # 73403349)
    Photo of 100 Burbank Ave, Warren, MA 01083 (MLS # 73403349)
    30
     
    100 Burbank Ave, Warren, MA
    100 Burbank Ave
    Warren, MA
    • 4 Beds
    • 3 Baths
    • 1,872 Home (sqft)
    • 3 Baths
    • 24,830 Lot (sqft)
    Listed with Coldwell Banker Realty - Worcester
  3. Photo of 180 Main St #6203, Bridgewater, MA 02334 (MLS # 73403344)
    $239,900
    Photo of 180 Main St #6203, Bridgewater, MA 02334 (MLS # 73403344)
    Photo of 180 Main St #6203, Bridgewater, MA 02334 (MLS # 73403344)
    180 Main St #6203, Bridgewater, MA
    180 Main St #6203
    Bridgewater, MA
    • 1 Bed
    • 1 Bath
    • 708 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Ballow and Hutchinson Realty Group, Inc.
  4. Photo of 320 Martins Landing Way #204, North Reading, MA 01864 (MLS # 73403340)
    $472,760
    Photo of 320 Martins Landing Way #204, North Reading, MA 01864 (MLS # 73403340)
    Photo of 320 Martins Landing Way #204, North Reading, MA 01864 (MLS # 73403340)
    19
     
    320 Martins Landing Way #204, North Reading, MA
    320 Martins Landing Way #204
    North Reading, MA
    • 1 Bed
    • 1 Bath
    • 1,027 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Pulte Homes of New England
  5. Photo of 3 Frost Ln, Hadley, MA 01035 (MLS # 73403337)
    $895,500
    Photo of 3 Frost Ln, Hadley, MA 01035 (MLS # 73403337)
    Photo of 3 Frost Ln, Hadley, MA 01035 (MLS # 73403337)
    41
     
    3 Frost Ln, Hadley, MA
    3 Frost Ln
    Hadley, MA
    • 3 Beds
    • 3 Baths
    • 2,670 Home (sqft)
    • 3 Baths
    • 20,909 Lot (sqft)
    Listed with OwnerEntry.com
  6. Photo of 2 Codman Way #408, Westborough, MA 01581 (MLS # 73403336)
    $632,999
    Photo of 2 Codman Way #408, Westborough, MA 01581 (MLS # 73403336)
    Photo of 2 Codman Way #408, Westborough, MA 01581 (MLS # 73403336)
    42
     
    2 Codman Way #408, Westborough, MA
    2 Codman Way #408
    Westborough, MA
    • 2 Beds
    • 2 Baths
    • 1,375 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Pulte Homes of New England
  7. Photo of 100 Station Lndg #409, Medford, MA 02155 (MLS # 73403329)
    $630,000
    Photo of 100 Station Lndg #409, Medford, MA 02155 (MLS # 73403329)
    Photo of 100 Station Lndg #409, Medford, MA 02155 (MLS # 73403329)
    42
     
    100 Station Lndg #409, Medford, MA
    100 Station Lndg #409
    Medford, MA
    • 1 Bed
    • 1 Bath
    • 785 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Cambridge
  8. Photo of 770 Cummins Hwy #22, Boston, MA 02126 (MLS # 73403334)
    $337,850
    Photo of 770 Cummins Hwy #22, Boston, MA 02126 (MLS # 73403334)
    Photo of 770 Cummins Hwy #22, Boston, MA 02126 (MLS # 73403334)
    20
     
    770 Cummins Hwy #22, Boston, MA
    770 Cummins Hwy #22
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 652 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
    Listed with Centre Realty Group
  9. Photo of 2-4 Poe Ave #1, Boylston, MA 01505 (MLS # 73403335)
    $599,900
    Photo of 2-4 Poe Ave #1, Boylston, MA 01505 (MLS # 73403335)
    Photo of 2-4 Poe Ave #1, Boylston, MA 01505 (MLS # 73403335)
    2-4 Poe Ave #1, Boylston, MA
    2-4 Poe Ave #1
    Boylston, MA
    • 2 Beds
    • 3 Baths
    • 1,806 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with For Sale For Owner Realty
  10. Photo of 183 L St #1, Boston, MA 02127 (MLS # 73403325)
    $749,000
    Photo of 183 L St #1, Boston, MA 02127 (MLS # 73403325)
    Photo of 183 L St #1, Boston, MA 02127 (MLS # 73403325)
    17
     
    183 L St #1, Boston, MA
    183 L St #1
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,235 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
    Listed with JW Brokerage
  11. Photo of 24 Johnson St, Malden, MA 02148 (MLS # 73403322)
    $695,000
    Photo of 24 Johnson St, Malden, MA 02148 (MLS # 73403322)
    Photo of 24 Johnson St, Malden, MA 02148 (MLS # 73403322)
    22
     
    24 Johnson St, Malden, MA
    24 Johnson St
    Malden, MA
    • 3 Beds
    • 2 Baths
    • 1,874 Home (sqft)
    • 2 Baths
    • 7,841 Lot (sqft)
    Listed with Boston Residential
  12. Photo of 23 Hemlock Dr, Ayer, MA 01432 (MLS # 73403324)
    $750,000
    Photo of 23 Hemlock Dr, Ayer, MA 01432 (MLS # 73403324)
    Photo of 23 Hemlock Dr, Ayer, MA 01432 (MLS # 73403324)
    27
     
    23 Hemlock Dr, Ayer, MA
    23 Hemlock Dr
    Ayer, MA
    • 3 Beds
    • 3 Baths
    • 2,259 Home (sqft)
    • 3 Baths
    • 40,076 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  13. Photo of 34 Sumner Ave #311, Springfield, MA 01108 (MLS # 73403318)
    $209,000
    Photo of 34 Sumner Ave #311, Springfield, MA 01108 (MLS # 73403318)
    Photo of 34 Sumner Ave #311, Springfield, MA 01108 (MLS # 73403318)
    34 Sumner Ave #311, Springfield, MA
    34 Sumner Ave #311
    Springfield, MA
    • 2 Beds
    • 2 Baths
    • 925 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Samuel D. Plotkin & Associates
  14. Photo of 240 Pine Tree Lane #240, Fitzwilliam, NH 03447 (MLS # 73403316)
    $339,900
    Photo of 240 Pine Tree Lane #240, Fitzwilliam, NH 03447 (MLS # 73403316)
    Photo of 240 Pine Tree Lane #240, Fitzwilliam, NH 03447 (MLS # 73403316)
    40
     
    240 Pine Tree Lane #240, Fitzwilliam, NH
    240 Pine Tree Lane #240
    Fitzwilliam, NH
    • 2 Beds
    • 1 Bath
    • 803 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Keller Williams Realty North Central
  15. Photo of 16 Carrier Lane, Sutton, MA 01590 (MLS # 73403317)
    $539,000
    Photo of 16 Carrier Lane, Sutton, MA 01590 (MLS # 73403317)
    Photo of 16 Carrier Lane, Sutton, MA 01590 (MLS # 73403317)
    22
     
    16 Carrier Lane, Sutton, MA
    16 Carrier Lane
    Sutton, MA
    • 3 Beds
    • 2 Baths
    • 1,244 Home (sqft)
    • 2 Baths
    • 2.15 Lot (ac)
    Listed with Lamacchia Realty, Inc.
  16. Photo of 4 Fidelity #2, Rutland, MA 01543 (MLS # 73403315)
    $498,000
    Photo of 4 Fidelity #2, Rutland, MA 01543 (MLS # 73403315)
    Photo of 4 Fidelity #2, Rutland, MA 01543 (MLS # 73403315)
    4 Fidelity #2, Rutland, MA
    4 Fidelity #2
    Rutland, MA
    • 2 Beds
    • 2 Baths
    • 1,582 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Harbor Classic Realty
  17. Photo of 29 Crystal St, Lowell, MA 01852 (MLS # 73403310)
    $573,999
    Photo of 29 Crystal St, Lowell, MA 01852 (MLS # 73403310)
    Photo of 29 Crystal St, Lowell, MA 01852 (MLS # 73403310)
    28
     
    29 Crystal St, Lowell, MA
    29 Crystal St
    Lowell, MA
    • 3 Beds
    • 1 Bath
    • 1,478 Home (sqft)
    • 1 Bath
    • 10,019 Lot (sqft)
    Listed with RE/MAX Innovative Properties
  18. Photo of 58-60 Pendleton Ave, Springfield, MA 01109 (MLS # 73403313)
    $390,000
    Photo of 58-60 Pendleton Ave, Springfield, MA 01109 (MLS # 73403313)
    Photo of 58-60 Pendleton Ave, Springfield, MA 01109 (MLS # 73403313)
    14
     
    58-60 Pendleton Ave, Springfield, MA
    58-60 Pendleton Ave
    Springfield, MA
    • 6 Beds
    • 2 Baths
    • 1,920 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
    Listed with Rose Bud Realty
  19. Photo of 119 Neck, Lancaster, MA 01523 (MLS # 73403304)
    $740,000
    Photo of 119 Neck, Lancaster, MA 01523 (MLS # 73403304)
    Photo of 119 Neck, Lancaster, MA 01523 (MLS # 73403304)
    41
     
    119 Neck, Lancaster, MA
    119 Neck
    Lancaster, MA
    • 3 Beds
    • 3 Baths
    • 3,352 Home (sqft)
    • 3 Baths
    • 2.20 Lot (ac)
    Listed with Central Mass Real Estate
  20. Photo of 132 Fidelity #61, Rutland, MA 01543 (MLS # 73403303)
    $539,000
    Photo of 132 Fidelity #61, Rutland, MA 01543 (MLS # 73403303)
    Photo of 132 Fidelity #61, Rutland, MA 01543 (MLS # 73403303)
    132 Fidelity #61, Rutland, MA
    132 Fidelity #61
    Rutland, MA
    • 2 Beds
    • 2 Baths
    • 2,149 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Harbor Classic Realty
  21. Photo of 45 Boatwrights Loop, Plymouth, MA 02360 (MLS # 73403295)
    $700,000
    Photo of 45 Boatwrights Loop, Plymouth, MA 02360 (MLS # 73403295)
    Photo of 45 Boatwrights Loop, Plymouth, MA 02360 (MLS # 73403295)
    38
     
    45 Boatwrights Loop, Plymouth, MA
    45 Boatwrights Loop
    Plymouth, MA
    • 2 Beds
    • 3 Baths
    • 1,992 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
    Listed with Pinehills Brokerage Services LLC
  22. Photo of 115 Conant St, Revere, MA 02151 (MLS # 73403297)
    $1,349,000
    Photo of 115 Conant St, Revere, MA 02151 (MLS # 73403297)
    Photo of 115 Conant St, Revere, MA 02151 (MLS # 73403297)
    18
     
    115 Conant St, Revere, MA
    115 Conant St
    Revere, MA
    • 6 Beds
    • 3 Baths
    • 4,013 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
    Listed with Century 21 North East
  23. Photo of 15 Suwanee Rd, Weymouth, MA 02189 (MLS # 73403290)
    $524,900
    Photo of 15 Suwanee Rd, Weymouth, MA 02189 (MLS # 73403290)
    Photo of 15 Suwanee Rd, Weymouth, MA 02189 (MLS # 73403290)
    19
     
    15 Suwanee Rd, Weymouth, MA
    15 Suwanee Rd
    Weymouth, MA
    • 3 Beds
    • 3 Baths
    • 1,604 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
    Listed with JDS Realty Group
  24. Photo of 72 Rookery Lane #3, Concord, MA 01742 (MLS # 73403285)
    $1,649,995
    Photo of 72 Rookery Lane #3, Concord, MA 01742 (MLS # 73403285)
    Photo of 72 Rookery Lane #3, Concord, MA 01742 (MLS # 73403285)
    37
     
    72 Rookery Lane #3, Concord, MA
    72 Rookery Lane #3
    Concord, MA
    • 4 Beds
    • 3 Baths
    • 3,998 Home (sqft)
    • 3 Baths
    • 21,780 Lot (sqft)
    Listed with Pulte Homes of New England
  25. Photo of 2 Julie Ln, Barnstable, MA 02635 (MLS # 73403281)
    $899,900
    Photo of 2 Julie Ln, Barnstable, MA 02635 (MLS # 73403281)
    Photo of 2 Julie Ln, Barnstable, MA 02635 (MLS # 73403281)
    41
     
    2 Julie Ln, Barnstable, MA
    2 Julie Ln
    Barnstable, MA
    • 3 Beds
    • 3 Baths
    • 1,801 Home (sqft)
    • 3 Baths
    • 43,560 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Robert Paul Properties
  26. Photo of 15 Vine Ave, Quincy, MA 02169 (MLS # 73403287)
    $1,550,000
    Photo of 15 Vine Ave, Quincy, MA 02169 (MLS # 73403287)
    Photo of 15 Vine Ave, Quincy, MA 02169 (MLS # 73403287)
    33
     
    15 Vine Ave, Quincy, MA
    15 Vine Ave
    Quincy, MA
    • 7 Beds
    • 6 Baths
    • 3,965 Home (sqft)
    • 6 Baths
    • 13,940 Lot (sqft)
    Listed with Escalate Real Estate
  27. Photo of 95 Red Brook Rd, Falmouth, MA 02536 (MLS # 73403277)
    $1,550,000
    Photo of 95 Red Brook Rd, Falmouth, MA 02536 (MLS # 73403277)
    Photo of 95 Red Brook Rd, Falmouth, MA 02536 (MLS # 73403277)
    42
     
    95 Red Brook Rd, Falmouth, MA
    95 Red Brook Rd
    Falmouth, MA
    • 4 Beds
    • 3 Baths
    • 2,514 Home (sqft)
    • 3 Baths
    • 1.73 Lot (ac)
    Listed with William Raveis R.E. & Home Services
  28. Photo of 477 Salisbury St, Worcester, MA 01609 (MLS # 73403279)
    $679,900
    Photo of 477 Salisbury St, Worcester, MA 01609 (MLS # 73403279)
    Photo of 477 Salisbury St, Worcester, MA 01609 (MLS # 73403279)
    42
     
    477 Salisbury St, Worcester, MA
    477 Salisbury St
    Worcester, MA
    • 3 Beds
    • 3 Baths
    • 2,296 Home (sqft)
    • 3 Baths
    • 16,118 Lot (sqft)
    Listed with Keller Williams Realty North Central
  29. Photo of 30 Adams Street, Littleton, MA 01460 (MLS # 73403266)
    $595,000
    Photo of 30 Adams Street, Littleton, MA 01460 (MLS # 73403266)
    Photo of 30 Adams Street, Littleton, MA 01460 (MLS # 73403266)
    42
     
    30 Adams Street, Littleton, MA
    30 Adams Street
    Littleton, MA
    • 3 Beds
    • 2 Baths
    • 1,563 Home (sqft)
    • 2 Baths
    • 25,265 Lot (sqft)
    Listed with Coldwell Banker Realty - Concord
  30. Photo of 34 Village Dr #34, Quincy, MA 02169 (MLS # 73403259)
    $699,000
    Photo of 34 Village Dr #34, Quincy, MA 02169 (MLS # 73403259)
    Photo of 34 Village Dr #34, Quincy, MA 02169 (MLS # 73403259)
    38
     
    34 Village Dr #34, Quincy, MA
    34 Village Dr #34
    Quincy, MA
    • 2 Beds
    • 2 Baths
    • 1,532 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Elite
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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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