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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 3/28/2024)

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  1. Photo of 35 Pilgrim Road, Harwich, MA 02646 (MLS # 73217228)
    $1,699,000
    Photo of 35 Pilgrim Road, Harwich, MA 02646 (MLS # 73217228)
    Photo of 35 Pilgrim Road, Harwich, MA 02646 (MLS # 73217228)
    33
     
    35 Pilgrim Road, Harwich, MA
    35 Pilgrim Road
    Harwich, MA
    • 3 Beds
    • 3 Baths
    • 2,895 Home (sqft)
    • 3 Baths
    • 10,455 Lot (sqft)
    Listed with Brady J. McDevitt
  2. Photo of 99 Ice House Lndg #99, Marlborough, MA 01752 (MLS # 73217224)
    $529,000
    Photo of 99 Ice House Lndg #99, Marlborough, MA 01752 (MLS # 73217224)
    Photo of 99 Ice House Lndg #99, Marlborough, MA 01752 (MLS # 73217224)
    27
     
    99 Ice House Lndg #99, Marlborough, MA
    99 Ice House Lndg #99
    Marlborough, MA
    • 2 Beds
    • 3 Baths
    • 1,488 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Redfin Corp.
  3. Photo of 43 Tupper Hill Rd #43, Plymouth, MA 02360 (MLS # 73217226)
    $435,000
    Photo of 43 Tupper Hill Rd #43, Plymouth, MA 02360 (MLS # 73217226)
    Photo of 43 Tupper Hill Rd #43, Plymouth, MA 02360 (MLS # 73217226)
    34
     
    43 Tupper Hill Rd #43, Plymouth, MA
    43 Tupper Hill Rd #43
    Plymouth, MA
    • 2 Beds
    • 2 Baths
    • 1,150 Home (sqft)
    • 2 Baths
    • 13.00 Lot (ac)
    Listed with Century 21 Classic Gold
  4. Photo of 90 School Street, Belmont, MA 02478 (MLS # 73217223)
    $1,875,000
    Photo of 90 School Street, Belmont, MA 02478 (MLS # 73217223)
    Photo of 90 School Street, Belmont, MA 02478 (MLS # 73217223)
    31
     
    90 School Street, Belmont, MA
    90 School Street
    Belmont, MA
    • 5 Beds
    • 2 Baths
    • 2,620 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
    Listed with Coldwell Banker Realty - Belmont
  5. Photo of 88 Rockland Street, Boston, MA 02132 (MLS # 73217225)
    $855,000
    Photo of 88 Rockland Street, Boston, MA 02132 (MLS # 73217225)
    Photo of 88 Rockland Street, Boston, MA 02132 (MLS # 73217225)
    34
     
    88 Rockland Street, Boston, MA
    88 Rockland Street
    Boston, MA
    • 3 Beds
    • 2 Baths
    • 2,054 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  6. Photo of 12 Woodland St #18, Everett, MA 02149 (MLS # 73217220)
    $349,900
    Photo of 12 Woodland St #18, Everett, MA 02149 (MLS # 73217220)
    Photo of 12 Woodland St #18, Everett, MA 02149 (MLS # 73217220)
    12
     
    12 Woodland St #18, Everett, MA
    12 Woodland St #18
    Everett, MA
    • 2 Beds
    • 1 Bath
    • 693 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  7. Photo of 220 Wood St, Hopkinton, MA 01748 (MLS # 73217221)
    $649,900
    Photo of 220 Wood St, Hopkinton, MA 01748 (MLS # 73217221)
    Photo of 220 Wood St, Hopkinton, MA 01748 (MLS # 73217221)
    25
     
    220 Wood St, Hopkinton, MA
    220 Wood St
    Hopkinton, MA
    • 3 Beds
    • 2 Baths
    • 2,164 Home (sqft)
    • 2 Baths
    • 33,106 Lot (sqft)
    Listed with eXp Realty
  8. Photo of 35 Proctor Ave, Fitchburg, MA 01420 (MLS # 73217219)
    $360,000
    Photo of 35 Proctor Ave, Fitchburg, MA 01420 (MLS # 73217219)
    Photo of 35 Proctor Ave, Fitchburg, MA 01420 (MLS # 73217219)
    40
     
    35 Proctor Ave, Fitchburg, MA
    35 Proctor Ave
    Fitchburg, MA
    • 3 Beds
    • 1 Bath
    • 1,080 Home (sqft)
    • 1 Bath
    • 14,811 Lot (sqft)
    Listed with Prestige Homes Real Estate, LLC
  9. Photo of 343 Commercial St #305, Boston, MA 02109 (MLS # 73217217)
    $1,895,000
    Photo of 343 Commercial St #305, Boston, MA 02109 (MLS # 73217217)
    Photo of 343 Commercial St #305, Boston, MA 02109 (MLS # 73217217)
    33
     
    343 Commercial St #305, Boston, MA
    343 Commercial St #305
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,394 Home (sqft)
    • 2 Baths
    • 1,307 Lot (sqft)
    Listed with CL Properties
  10. Photo of 150 Seaport Blvd #16E, Boston, MA 02210 (MLS # 73217208)
    $8,290,000
    Photo of 150 Seaport Blvd #16E, Boston, MA 02210 (MLS # 73217208)
    Photo of 150 Seaport Blvd #16E, Boston, MA 02210 (MLS # 73217208)
    34
     
    150 Seaport Blvd #16E, Boston, MA
    150 Seaport Blvd #16E
    Boston, MA
    • 3 Beds
    • 4 Baths
    • 2,553 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with Elevated Realty, LLC
  11. Photo of 453 Main St, Northborough, MA 01532 (MLS # 73213499)
    $875,000
    Photo of 453 Main St, Northborough, MA 01532 (MLS # 73213499)
    Photo of 453 Main St, Northborough, MA 01532 (MLS # 73213499)
    42
     
    453 Main St, Northborough, MA
    453 Main St
    Northborough, MA
    • 4 Beds
    • 3 Baths
    • 3,000 Home (sqft)
    • 3 Baths
    • 1.06 Lot (ac)
    Listed with Century 21 North East
  12. Photo of 201 Gorwin Dr, Holliston, MA 01746 (MLS # 73217210)
    $649,900
    Photo of 201 Gorwin Dr, Holliston, MA 01746 (MLS # 73217210)
    Photo of 201 Gorwin Dr, Holliston, MA 01746 (MLS # 73217210)
    21
     
    201 Gorwin Dr, Holliston, MA
    201 Gorwin Dr
    Holliston, MA
    • 4 Beds
    • 2 Baths
    • 1,950 Home (sqft)
    • 2 Baths
    • 22,652 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Page Realty
  13. Photo of 95 Anderer Lane #7, Boston, MA 02132 (MLS # 73217211)
    $650,000
    Photo of 95 Anderer Lane #7, Boston, MA 02132 (MLS # 73217211)
    Photo of 95 Anderer Lane #7, Boston, MA 02132 (MLS # 73217211)
    18
     
    95 Anderer Lane #7, Boston, MA
    95 Anderer Lane #7
    Boston, MA
    • 2 Beds
    • 3 Baths
    • 1,501 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Brookline
  14. Photo of 69 Robeson St #4, Boston, MA 02130 (MLS # 73217209)
    $989,000
    Photo of 69 Robeson St #4, Boston, MA 02130 (MLS # 73217209)
    Photo of 69 Robeson St #4, Boston, MA 02130 (MLS # 73217209)
    34
     
    69 Robeson St #4, Boston, MA
    69 Robeson St #4
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 2,145 Home (sqft)
    • 2 Baths
    • 30,057 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  15. Photo of 16 Shire Rd #16, Leominster, MA 01453 (MLS # 73217212)
    $330,000
    Photo of 16 Shire Rd #16, Leominster, MA 01453 (MLS # 73217212)
    Photo of 16 Shire Rd #16, Leominster, MA 01453 (MLS # 73217212)
    31
     
    16 Shire Rd #16, Leominster, MA
    16 Shire Rd #16
    Leominster, MA
    • 2 Beds
    • 2 Baths
    • 1,376 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Central Mass Real Estate
  16. Photo of 147 Boylston St, Shrewsbury, MA 01545 (MLS # 73217206)
    $424,900
    Photo of 147 Boylston St, Shrewsbury, MA 01545 (MLS # 73217206)
    Photo of 147 Boylston St, Shrewsbury, MA 01545 (MLS # 73217206)
    23
     
    147 Boylston St, Shrewsbury, MA
    147 Boylston St
    Shrewsbury, MA
    • 3 Beds
    • 2 Baths
    • 1,492 Home (sqft)
    • 2 Baths
    • 7,406 Lot (sqft)
    Listed with Real Broker MA, LLC
  17. Photo of 65 Bennett St, Waltham, MA 02453 (MLS # 73217207)
    $629,900
    Photo of 65 Bennett St, Waltham, MA 02453 (MLS # 73217207)
    Photo of 65 Bennett St, Waltham, MA 02453 (MLS # 73217207)
    30
     
    65 Bennett St, Waltham, MA
    65 Bennett St
    Waltham, MA
    • 2 Beds
    • 1 Bath
    • 1,058 Home (sqft)
    • 1 Bath
    • 4,792 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  18. Photo of 88 Round Hill Rd #4, Northampton, MA 01060 (MLS # 73217200)
    $699,000
    Photo of 88 Round Hill Rd #4, Northampton, MA 01060 (MLS # 73217200)
    Photo of 88 Round Hill Rd #4, Northampton, MA 01060 (MLS # 73217200)
    40
     
    88 Round Hill Rd #4, Northampton, MA
    88 Round Hill Rd #4
    Northampton, MA
    • 2 Beds
    • 3 Baths
    • 2,184 Home (sqft)
    • 3 Baths
    • 24,830 Lot (sqft)
    Listed with The Murphys REALTORS®, Inc.
  19. Photo of 98 Mechanic St #F, Foxboro, MA 02035 (MLS # 73217198)
    $399,999
    Photo of 98 Mechanic St #F, Foxboro, MA 02035 (MLS # 73217198)
    Photo of 98 Mechanic St #F, Foxboro, MA 02035 (MLS # 73217198)
    22
     
    98 Mechanic St #F, Foxboro, MA
    98 Mechanic St #F
    Foxboro, MA
    • 2 Beds
    • 2 Baths
    • 1,164 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with StartPoint Realty
  20. Photo of 121 Cedar St, Ashland, MA 01721 (MLS # 73217197)
    $899,900
    Photo of 121 Cedar St, Ashland, MA 01721 (MLS # 73217197)
    Photo of 121 Cedar St, Ashland, MA 01721 (MLS # 73217197)
    42
     
    121 Cedar St, Ashland, MA
    121 Cedar St
    Ashland, MA
    • 5 Beds
    • 4 Baths
    • 3,812 Home (sqft)
    • 4 Baths
    • 30,057 Lot (sqft)
    Listed with Realty Executives Boston West
  21. Photo of 54 Marjorie St, Ware, MA 01082 (MLS # 73217199)
    $249,900
    Photo of 54 Marjorie St, Ware, MA 01082 (MLS # 73217199)
    Photo of 54 Marjorie St, Ware, MA 01082 (MLS # 73217199)
    29
     
    54 Marjorie St, Ware, MA
    54 Marjorie St
    Ware, MA
    • 2 Beds
    • 2 Baths
    • 1,365 Home (sqft)
    • 2 Baths
    • 16,989 Lot (sqft)
    Listed with ROVI Homes
  22. Photo of 210 South St #5-1, Boston, MA 02111 (MLS # 73217195)
    $1,125,000
    Photo of 210 South St #5-1, Boston, MA 02111 (MLS # 73217195)
    Photo of 210 South St #5-1, Boston, MA 02111 (MLS # 73217195)
    22
     
    210 South St #5-1, Boston, MA
    210 South St #5-1
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,730 Home (sqft)
    • 2 Baths
    • 1,743 Lot (sqft)
    Listed with Redfin Corp.
  23. Photo of 4 Murray Hill Rd, Chelmsford, MA 01824 (MLS # 73217196)
    $665,000
    Photo of 4 Murray Hill Rd, Chelmsford, MA 01824 (MLS # 73217196)
    Photo of 4 Murray Hill Rd, Chelmsford, MA 01824 (MLS # 73217196)
    42
     
    4 Murray Hill Rd, Chelmsford, MA
    4 Murray Hill Rd
    Chelmsford, MA
    • 3 Beds
    • 3 Baths
    • 2,914 Home (sqft)
    • 3 Baths
    • 22,652 Lot (sqft)
    Listed with LAER Realty Partners
  24. Photo of 23 Dartmouth St, Quincy, MA 02169 (MLS # 73217193)
    $795,000
    Photo of 23 Dartmouth St, Quincy, MA 02169 (MLS # 73217193)
    Photo of 23 Dartmouth St, Quincy, MA 02169 (MLS # 73217193)
    23 Dartmouth St, Quincy, MA
    23 Dartmouth St
    Quincy, MA
    • 5 Beds
    • 2 Baths
    • 2,210 Home (sqft)
    • 2 Baths
    • 3,050 Lot (sqft)
    Listed with Landing Realty, Inc.
  25. Photo of 6 Elmcrest Dr #6, Chicopee, MA 01013 (MLS # 73217187)
    $465,000
    Photo of 6 Elmcrest Dr #6, Chicopee, MA 01013 (MLS # 73217187)
    Photo of 6 Elmcrest Dr #6, Chicopee, MA 01013 (MLS # 73217187)
    34
     
    6 Elmcrest Dr #6, Chicopee, MA
    6 Elmcrest Dr #6
    Chicopee, MA
    • 3 Beds
    • 3 Baths
    • 1,305 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Realty Professionals
  26. Photo of 4 Derne St #1, Boston, MA 02114 (MLS # 73217188)
    $899,000
    Photo of 4 Derne St #1, Boston, MA 02114 (MLS # 73217188)
    Photo of 4 Derne St #1, Boston, MA 02114 (MLS # 73217188)
    14
     
    4 Derne St #1, Boston, MA
    4 Derne St #1
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,145 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with The Charles Realty
  27. Photo of 947949 Chestnut Street #2, Newton, MA 02464 (MLS # 73217189)
    $620,000
    Photo of 947949 Chestnut Street #2, Newton, MA 02464 (MLS # 73217189)
    Photo of 947949 Chestnut Street #2, Newton, MA 02464 (MLS # 73217189)
    33
     
    947949 Chestnut Street #2, Newton, MA
    947949 Chestnut Street #2
    Newton, MA
    • 2 Beds
    • 2 Baths
    • 1,190 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
    Listed with Redfin Corp.
  28. Photo of 3 Colonel Rolls Drive (Lot 7) Dr, Westford, MA 01886 (MLS # 73217183)
    $1,499,000
    Photo of 3 Colonel Rolls Drive (Lot 7) Dr, Westford, MA 01886 (MLS # 73217183)
    Photo of 3 Colonel Rolls Drive (Lot 7) Dr, Westford, MA 01886 (MLS # 73217183)
    15
     
    3 Colonel Rolls Drive (Lot 7) Dr, Westford, MA
    3 Colonel Rolls Drive (Lot 7) Dr
    Westford, MA
    • 5 Beds
    • 3 Baths
    • 3,570 Home (sqft)
    • 3 Baths
    • 21,345 Lot (sqft)
    Listed with Keller Williams Realty-Merrimack
  29. Photo of 135 Bayberry Circle, Winchendon, MA 01475 (MLS # 73217180)
    $375,000
    Photo of 135 Bayberry Circle, Winchendon, MA 01475 (MLS # 73217180)
    Photo of 135 Bayberry Circle, Winchendon, MA 01475 (MLS # 73217180)
    39
     
    135 Bayberry Circle, Winchendon, MA
    135 Bayberry Circle
    Winchendon, MA
    • 3 Beds
    • 2 Baths
    • 1,138 Home (sqft)
    • 2 Baths
    • 17,860 Lot (sqft)
    Listed with Elm Grove Realty, LLC
  30. Photo of 21 Aspen Drive, Pelham, NH 03076 (MLS # 73217186)
    $832,900
    Photo of 21 Aspen Drive, Pelham, NH 03076 (MLS # 73217186)
    Photo of 21 Aspen Drive, Pelham, NH 03076 (MLS # 73217186)
    36
     
    21 Aspen Drive, Pelham, NH
    21 Aspen Drive
    Pelham, NH
    • 2 Beds
    • 2 Baths
    • 2,052 Home (sqft)
    • 2 Baths
    • 40,511 Lot (sqft)
    Listed with Keller Williams Realty Evolution
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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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