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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 4/22/2025)

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  1. Photo of 30 Highview Road, Rockport, MA 01966 (MLS # 73362249)
    $1,000,000
    Photo of 30 Highview Road, Rockport, MA 01966 (MLS # 73362249)
    Photo of 30 Highview Road, Rockport, MA 01966 (MLS # 73362249)
    33
     
    30 Highview Road, Rockport, MA
    30 Highview Road
    Rockport, MA
    • 3 Beds
    • 3 Baths
    • 2,128 Home (sqft)
    • 3 Baths
    • 37,462 Lot (sqft)
    Listed with Compass
  2. Photo of 183 Bass Point Rd, Nahant, MA 01908 (MLS # 73362247)
    $2,950,000
    Photo of 183 Bass Point Rd, Nahant, MA 01908 (MLS # 73362247)
    Photo of 183 Bass Point Rd, Nahant, MA 01908 (MLS # 73362247)
    33
     
    183 Bass Point Rd, Nahant, MA
    183 Bass Point Rd
    Nahant, MA
    • 4 Beds
    • 4 Baths
    • 3,295 Home (sqft)
    • 4 Baths
    • 12,633 Lot (sqft)
    Listed with REAL ESTATE and Company
  3. Photo of 35 Tuckernuck Ave, Oak Bluffs, MA 02557 (MLS # 73362245)
    $1,895,000
    Photo of 35 Tuckernuck Ave, Oak Bluffs, MA 02557 (MLS # 73362245)
    Photo of 35 Tuckernuck Ave, Oak Bluffs, MA 02557 (MLS # 73362245)
    34
     
    35 Tuckernuck Ave, Oak Bluffs, MA
    35 Tuckernuck Ave
    Oak Bluffs, MA
    • 5 Beds
    • 2 Baths
    • 1,918 Home (sqft)
    • 2 Baths
    • 4,792 Lot (sqft)
    Listed with Compass
  4. Photo of 21 John St, Worcester, MA 01609 (MLS # 73362242)
    $639,000
    Photo of 21 John St, Worcester, MA 01609 (MLS # 73362242)
    Photo of 21 John St, Worcester, MA 01609 (MLS # 73362242)
    20
     
    21 John St, Worcester, MA
    21 John St
    Worcester, MA
    • 6 Beds
    • 4 Baths
    • 2,663 Home (sqft)
    • 4 Baths
    • 4,792 Lot (sqft)
    Listed with Pondside Realty
  5. Photo of 3-5 Dean St, Stoneham, MA 02180 (MLS # 73362241)
    $870,000
    Photo of 3-5 Dean St, Stoneham, MA 02180 (MLS # 73362241)
    Photo of 3-5 Dean St, Stoneham, MA 02180 (MLS # 73362241)
    28
     
    3-5 Dean St, Stoneham, MA
    3-5 Dean St
    Stoneham, MA
    • 6 Beds
    • 3 Baths
    • 2,692 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
    Listed with Compass
  6. Photo of 40 Bonney Briar Dr, Plymouth, MA 02360 (MLS # 73362238)
    $550,000
    Photo of 40 Bonney Briar Dr, Plymouth, MA 02360 (MLS # 73362238)
    Photo of 40 Bonney Briar Dr, Plymouth, MA 02360 (MLS # 73362238)
    38
     
    40 Bonney Briar Dr, Plymouth, MA
    40 Bonney Briar Dr
    Plymouth, MA
    • 3 Beds
    • 2 Baths
    • 1,664 Home (sqft)
    • 2 Baths
    • 20,038 Lot (sqft)
    Listed with Conway - Mattapoisett
  7. Photo of 8 Mercer St #3, Boston, MA 02127 (MLS # 73362233)
    $1,280,000
    Photo of 8 Mercer St #3, Boston, MA 02127 (MLS # 73362233)
    Photo of 8 Mercer St #3, Boston, MA 02127 (MLS # 73362233)
    19
     
    8 Mercer St #3, Boston, MA
    8 Mercer St #3
    Boston, MA
    • 3 Beds
    • 2 Baths
    • 1,470 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Downtown Boston Realty
  8. Photo of 128 Franklin St, Haverhill, MA 01830 (MLS # 73362230)
    $689,000
    Photo of 128 Franklin St, Haverhill, MA 01830 (MLS # 73362230)
    Photo of 128 Franklin St, Haverhill, MA 01830 (MLS # 73362230)
    34
     
    128 Franklin St, Haverhill, MA
    128 Franklin St
    Haverhill, MA
    • 5 Beds
    • 2 Baths
    • 2,354 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
    Listed with Coldwell Banker Realty - Marblehead
  9. Photo of 5 Powissett St, Dover, MA 02030 (MLS # 73362220)
    $2,350,000
    Photo of 5 Powissett St, Dover, MA 02030 (MLS # 73362220)
    Photo of 5 Powissett St, Dover, MA 02030 (MLS # 73362220)
    40
     
    5 Powissett St, Dover, MA
    5 Powissett St
    Dover, MA
    • 4 Beds
    • 4 Baths
    • 4,848 Home (sqft)
    • 4 Baths
    • 2.00 Lot (ac)
    Listed with Compass
  10. Photo of 70 Upsala St, Worcester, MA 01610 (MLS # 73362199)
    $850,000
    Photo of 70 Upsala St, Worcester, MA 01610 (MLS # 73362199)
    Photo of 70 Upsala St, Worcester, MA 01610 (MLS # 73362199)
    40
     
    70 Upsala St, Worcester, MA
    70 Upsala St
    Worcester, MA
    • 8 Beds
    • 4 Baths
    • 2,672 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
    Listed with Murilo Silva
  11. Photo of 263 Woodbine Avenue, Hanson, MA 02341 (MLS # 73362226)
    $529,900
    Photo of 263 Woodbine Avenue, Hanson, MA 02341 (MLS # 73362226)
    Photo of 263 Woodbine Avenue, Hanson, MA 02341 (MLS # 73362226)
    34
     
    263 Woodbine Avenue, Hanson, MA
    263 Woodbine Avenue
    Hanson, MA
    • 3 Beds
    • 2 Baths
    • 1,794 Home (sqft)
    • 2 Baths
    • 13,940 Lot (sqft)
    Listed with Keller Williams Realty
  12. Photo of 2 Wharf Road, Rockport, MA 01966 (MLS # 73362221)
    $1,395,000
    Photo of 2 Wharf Road, Rockport, MA 01966 (MLS # 73362221)
    Photo of 2 Wharf Road, Rockport, MA 01966 (MLS # 73362221)
    24
     
    2 Wharf Road, Rockport, MA
    2 Wharf Road
    Rockport, MA
    • 2 Beds
    • 2 Baths
    • 1,296 Home (sqft)
    • 2 Baths
    • 5,663 Lot (sqft)
    Listed with Compass
  13. Photo of 324 Colonel Hunt Dr, Abington, MA 02351 (MLS # 73362204)
    $589,900
    Photo of 324 Colonel Hunt Dr, Abington, MA 02351 (MLS # 73362204)
    Photo of 324 Colonel Hunt Dr, Abington, MA 02351 (MLS # 73362204)
    39
     
    324 Colonel Hunt Dr, Abington, MA
    324 Colonel Hunt Dr
    Abington, MA
    • 3 Beds
    • 2 Baths
    • 1,492 Home (sqft)
    • 2 Baths
    • 21,345 Lot (sqft)
    Listed with HomeSmart First Class Realty
  14. Photo of 111 Daniel Shays Hwy #30, Belchertown, MA 01007 (MLS # 73362202)
    $450,000
    Photo of 111 Daniel Shays Hwy #30, Belchertown, MA 01007 (MLS # 73362202)
    Photo of 111 Daniel Shays Hwy #30, Belchertown, MA 01007 (MLS # 73362202)
    26
     
    111 Daniel Shays Hwy #30, Belchertown, MA
    111 Daniel Shays Hwy #30
    Belchertown, MA
    • 2 Beds
    • 2 Baths
    • 1,500 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with RE/MAX Compass
  15. Photo of 35 Waverly St #35, Brookline, MA 02445 (MLS # 73362190)
    $2,349,680
    Photo of 35 Waverly St #35, Brookline, MA 02445 (MLS # 73362190)
    Photo of 35 Waverly St #35, Brookline, MA 02445 (MLS # 73362190)
    32
     
    35 Waverly St #35, Brookline, MA
    35 Waverly St #35
    Brookline, MA
    • 4 Beds
    • 3 Baths
    • 2,782 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Dreamega International Realty LLC
  16. Photo of 34 Blake St, Revere, MA 02151 (MLS # 73362198)
    $425,000
    Photo of 34 Blake St, Revere, MA 02151 (MLS # 73362198)
    Photo of 34 Blake St, Revere, MA 02151 (MLS # 73362198)
    16
     
    34 Blake St, Revere, MA
    34 Blake St
    Revere, MA
    • 3 Beds
    • 1 Bath
    • 1,341 Home (sqft)
    • 1 Bath
    • 3,050 Lot (sqft)
    Listed with Harmony Hill Realty LLC
  17. Photo of 281 South St, Medfield, MA 02052 (MLS # 73362189)
    $999,000
    Photo of 281 South St, Medfield, MA 02052 (MLS # 73362189)
    Photo of 281 South St, Medfield, MA 02052 (MLS # 73362189)
    25
     
    281 South St, Medfield, MA
    281 South St
    Medfield, MA
    • 3 Beds
    • 3 Baths
    • 2,527 Home (sqft)
    • 3 Baths
    • 4.00 Lot (ac)
    Listed with William Raveis R.E. & Home Services
  18. Photo of 27 Willis St, Boston, MA 02125 (MLS # 73362187)
    $1,299,000
    Photo of 27 Willis St, Boston, MA 02125 (MLS # 73362187)
    Photo of 27 Willis St, Boston, MA 02125 (MLS # 73362187)
    24
     
    27 Willis St, Boston, MA
    27 Willis St
    Boston, MA
    • 6 Beds
    • 3 Baths
    • 3,960 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
    Listed with Compass
  19. Photo of 199 Winchester St #199, Brookline, MA 02446 (MLS # 73362227)
    $3,095,000
    Photo of 199 Winchester St #199, Brookline, MA 02446 (MLS # 73362227)
    Photo of 199 Winchester St #199, Brookline, MA 02446 (MLS # 73362227)
    26
     
    199 Winchester St #199, Brookline, MA
    199 Winchester St #199
    Brookline, MA
    • 4 Beds
    • 4 Baths
    • 2,696 Home (sqft)
    • 4 Baths
    • 0 Lot (sqft)
    Listed with RE/MAX On the Charles
  20. Photo of 50 Castle View Drive, Gloucester, MA 01930 (MLS # 73362222)
    $1,850,000
    Photo of 50 Castle View Drive, Gloucester, MA 01930 (MLS # 73362222)
    Photo of 50 Castle View Drive, Gloucester, MA 01930 (MLS # 73362222)
    39
     
    50 Castle View Drive, Gloucester, MA
    50 Castle View Drive
    Gloucester, MA
    • 4 Beds
    • 5 Baths
    • 4,292 Home (sqft)
    • 5 Baths
    • 20,038 Lot (sqft)
    Listed with Compass
  21. Photo of 50 Malibu Drive, Taunton, MA 02780 (MLS # 73362186)
    $765,000
    Photo of 50 Malibu Drive, Taunton, MA 02780 (MLS # 73362186)
    Photo of 50 Malibu Drive, Taunton, MA 02780 (MLS # 73362186)
    34
     
    50 Malibu Drive, Taunton, MA
    50 Malibu Drive
    Taunton, MA
    • 5 Beds
    • 3 Baths
    • 3,612 Home (sqft)
    • 3 Baths
    • 1.91 Lot (ac)
    Listed with F. J. Torres Insurance Agency
  22. Photo of 240 Devonshire Street #5006, Boston, MA 02110 (MLS # 73362225)
    $4,640,000
    Photo of 240 Devonshire Street #5006, Boston, MA 02110 (MLS # 73362225)
    Photo of 240 Devonshire Street #5006, Boston, MA 02110 (MLS # 73362225)
    40
     
    240 Devonshire Street #5006, Boston, MA
    240 Devonshire Street #5006
    Boston, MA
    • 2 Beds
    • 3 Baths
    • 1,755 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with MP Boston Marketing LLC
  23. Photo of 50 Thompson St, New Bedford, MA 02740 (MLS # 73362182)
    $569,900
    Photo of 50 Thompson St, New Bedford, MA 02740 (MLS # 73362182)
    Photo of 50 Thompson St, New Bedford, MA 02740 (MLS # 73362182)
    23
     
    50 Thompson St, New Bedford, MA
    50 Thompson St
    New Bedford, MA
    • 8 Beds
    • 3 Baths
    • 3,649 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
    Listed with ERA The Castelo Group
  24. Photo of 85 Cedar Street, Wellesley, MA 02481 (MLS # 73362180)
    $2,150,000
    Photo of 85 Cedar Street, Wellesley, MA 02481 (MLS # 73362180)
    Photo of 85 Cedar Street, Wellesley, MA 02481 (MLS # 73362180)
    85 Cedar Street, Wellesley, MA
    85 Cedar Street
    Wellesley, MA
    • 5 Beds
    • 5 Baths
    • 4,000 Home (sqft)
    • 5 Baths
    • 10,890 Lot (sqft)
    Listed with Century 21 Shawmut Properties
  25. Photo of 98 Prescott St #3B, Boston, MA 02128 (MLS # 73362181)
    $550,000
    Photo of 98 Prescott St #3B, Boston, MA 02128 (MLS # 73362181)
    Photo of 98 Prescott St #3B, Boston, MA 02128 (MLS # 73362181)
    98 Prescott St #3B, Boston, MA
    98 Prescott St #3B
    Boston, MA
    • 1 Bed
    • 1 Bath
    • 635 Home (sqft)
    • 1 Bath
    • 3,921 Lot (sqft)
    Listed with Access
  26. Photo of 98 Prescott St #2A, Boston, MA 02128 (MLS # 73362177)
    $600,000
    Photo of 98 Prescott St #2A, Boston, MA 02128 (MLS # 73362177)
    Photo of 98 Prescott St #2A, Boston, MA 02128 (MLS # 73362177)
    98 Prescott St #2A, Boston, MA
    98 Prescott St #2A
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 746 Home (sqft)
    • 1 Bath
    • 3,921 Lot (sqft)
    Listed with Access
  27. Photo of 137 River Road, West Newbury, MA 01985 (MLS # 73362174)
    $1,999,995
    Photo of 137 River Road, West Newbury, MA 01985 (MLS # 73362174)
    Photo of 137 River Road, West Newbury, MA 01985 (MLS # 73362174)
    40
     
    137 River Road, West Newbury, MA
    137 River Road
    West Newbury, MA
    • 3 Beds
    • 5 Baths
    • 3,767 Home (sqft)
    • 5 Baths
    • 1.30 Lot (ac)
    Listed with Lyv Realty
  28. Photo of 46 Middlesex St, Fall River, MA 02723 (MLS # 73362170)
    $340,000
    Photo of 46 Middlesex St, Fall River, MA 02723 (MLS # 73362170)
    Photo of 46 Middlesex St, Fall River, MA 02723 (MLS # 73362170)
    27
     
    46 Middlesex St, Fall River, MA
    46 Middlesex St
    Fall River, MA
    • 2 Beds
    • 1 Bath
    • 720 Home (sqft)
    • 1 Bath
    • 4,356 Lot (sqft)
    Listed with Epique Realty
  29. Photo of 6 Paddock Dr, Harwich, MA 02645 (MLS # 73362171)
    $699,900
    Photo of 6 Paddock Dr, Harwich, MA 02645 (MLS # 73362171)
    Photo of 6 Paddock Dr, Harwich, MA 02645 (MLS # 73362171)
    41
     
    6 Paddock Dr, Harwich, MA
    6 Paddock Dr
    Harwich, MA
    • 2 Beds
    • 2 Baths
    • 2,396 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
    Listed with Distinctly New England
  30. Photo of 14 Maxdale Road, Worcester, MA 01602 (MLS # 73362169)
    $599,000
    Photo of 14 Maxdale Road, Worcester, MA 01602 (MLS # 73362169)
    Photo of 14 Maxdale Road, Worcester, MA 01602 (MLS # 73362169)
    42
     
    14 Maxdale Road, Worcester, MA
    14 Maxdale Road
    Worcester, MA
    • 4 Beds
    • 3 Baths
    • 1,984 Home (sqft)
    • 3 Baths
    • 6,970 Lot (sqft)
    Listed with ERA Key Realty Services- Spenc
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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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