Call Alexa: (781) 630-1704

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.

  • List View
  • Map View
  • Grid View

See all Real estate matching your search.
(all data current as of 6/18/2025)

Listing information deemed reliable but not guaranteed. Read full disclaimer.

 
 

Show Map
  • List View
  • Grid View
Sorted by
31 - 60 of 500+ | Previous Page 2 of 17 Next
  1. Photo of 33 Pearl St #D, Boston, MA 02125 (MLS # 73393100)
    $1,100,000
    Photo of 33 Pearl St #D, Boston, MA 02125 (MLS # 73393100)
    Photo of 33 Pearl St #D, Boston, MA 02125 (MLS # 73393100)
    33 Pearl St #D, Boston, MA
    33 Pearl St #D
    Boston, MA
    • 3 Beds
    • 2 Baths
    • 1,887 Home (sqft)
    • 2 Baths
    • 9,584 Lot (sqft)
    Listed with Northeast Realty + Co.
  2. Photo of 26 Dalby Street, Newton, MA 02458 (MLS # 73393087)
    $1,795,000
    Photo of 26 Dalby Street, Newton, MA 02458 (MLS # 73393087)
    Photo of 26 Dalby Street, Newton, MA 02458 (MLS # 73393087)
    22
     
    26 Dalby Street, Newton, MA
    26 Dalby Street
    Newton, MA
    • 4 Beds
    • 4 Baths
    • 3,554 Home (sqft)
    • 4 Baths
    • 23,523 Lot (sqft)
    Listed with Compass
  3. Photo of 16-26 Dalby Street #4, Newton, MA 02458 (MLS # 73393082)
    $1,795,000
    Photo of 16-26 Dalby Street #4, Newton, MA 02458 (MLS # 73393082)
    Photo of 16-26 Dalby Street #4, Newton, MA 02458 (MLS # 73393082)
    22
     
    16-26 Dalby Street #4, Newton, MA
    16-26 Dalby Street #4
    Newton, MA
    • 4 Beds
    • 4 Baths
    • 3,554 Home (sqft)
    • 4 Baths
    • 23,523 Lot (sqft)
    Listed with Compass
  4. Photo of 758 North Hoosac Road, Williamstown, MA 01267 (MLS # 73393104)
    $460,000
    Photo of 758 North Hoosac Road, Williamstown, MA 01267 (MLS # 73393104)
    Photo of 758 North Hoosac Road, Williamstown, MA 01267 (MLS # 73393104)
    30
     
    758 North Hoosac Road, Williamstown, MA
    758 North Hoosac Road
    Williamstown, MA
    • 3 Beds
    • 2 Baths
    • 2,024 Home (sqft)
    • 2 Baths
    • 19,602 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  5. Photo of 60 Shore Road, Douglas, MA 01516 (MLS # 73393094)
    $609,000
    Photo of 60 Shore Road, Douglas, MA 01516 (MLS # 73393094)
    Photo of 60 Shore Road, Douglas, MA 01516 (MLS # 73393094)
    38
     
    60 Shore Road, Douglas, MA
    60 Shore Road
    Douglas, MA
    • 2 Beds
    • 1 Bath
    • 1,020 Home (sqft)
    • 1 Bath
    • 10,019 Lot (sqft)
    Listed with Lindsey Sarah Realty Group
  6. Photo of 453 Forest Street, North Andover, MA 01845 (MLS # 73393098)
    $1,299,000
    Photo of 453 Forest Street, North Andover, MA 01845 (MLS # 73393098)
    Photo of 453 Forest Street, North Andover, MA 01845 (MLS # 73393098)
    31
     
    453 Forest Street, North Andover, MA
    453 Forest Street
    North Andover, MA
    • 4 Beds
    • 4 Baths
    • 5,142 Home (sqft)
    • 4 Baths
    • 2.00 Lot (ac)
    Listed with Compass
  7. Photo of 24 Coventry Rd #24, Grafton, MA 01519 (MLS # 73393093)
    $400,000
    Photo of 24 Coventry Rd #24, Grafton, MA 01519 (MLS # 73393093)
    Photo of 24 Coventry Rd #24, Grafton, MA 01519 (MLS # 73393093)
    24
     
    24 Coventry Rd #24, Grafton, MA
    24 Coventry Rd #24
    Grafton, MA
    • 3 Beds
    • 2 Baths
    • 1,344 Home (sqft)
    • 2 Baths
    • 10.26 Lot (ac)
    Listed with RE/MAX Executive Realty
  8. Photo of 9 Hinckley Rd, Tewksbury, MA 01876 (MLS # 73393097)
    $539,900
    Photo of 9 Hinckley Rd, Tewksbury, MA 01876 (MLS # 73393097)
    Photo of 9 Hinckley Rd, Tewksbury, MA 01876 (MLS # 73393097)
    21
     
    9 Hinckley Rd, Tewksbury, MA
    9 Hinckley Rd
    Tewksbury, MA
    • 2 Beds
    • 1 Bath
    • 936 Home (sqft)
    • 1 Bath
    • 11,326 Lot (sqft)
    Listed with Re/Max Innovative Properties
  9. Photo of 58 Field Street, West Springfield, MA 01089 (MLS # 73393095)
    $249,000
    Photo of 58 Field Street, West Springfield, MA 01089 (MLS # 73393095)
    Photo of 58 Field Street, West Springfield, MA 01089 (MLS # 73393095)
    28
     
    58 Field Street, West Springfield, MA
    58 Field Street
    West Springfield, MA
    • 4 Beds
    • 2 Baths
    • 1,323 Home (sqft)
    • 2 Baths
    • 3,921 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Realty Professionals
  10. Photo of 23 Indian Cove Way #23, Easton, MA 02375 (MLS # 73393075)
    $424,900
    Photo of 23 Indian Cove Way #23, Easton, MA 02375 (MLS # 73393075)
    Photo of 23 Indian Cove Way #23, Easton, MA 02375 (MLS # 73393075)
    41
     
    23 Indian Cove Way #23, Easton, MA
    23 Indian Cove Way #23
    Easton, MA
    • 1 Bed
    • 3 Baths
    • 2,160 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Premier Properties
  11. Photo of 74 Muller Rd, Burlington, MA 01803 (MLS # 73393080)
    $1,395,000
    Photo of 74 Muller Rd, Burlington, MA 01803 (MLS # 73393080)
    Photo of 74 Muller Rd, Burlington, MA 01803 (MLS # 73393080)
    40
     
    74 Muller Rd, Burlington, MA
    74 Muller Rd
    Burlington, MA
    • 4 Beds
    • 3 Baths
    • 3,568 Home (sqft)
    • 3 Baths
    • 20,038 Lot (sqft)
    Listed with Elite Realty Experts, LLC
  12. Photo of 8 Messina Circle, Methuen, MA 01844 (MLS # 73393076)
    $649,900
    Photo of 8 Messina Circle, Methuen, MA 01844 (MLS # 73393076)
    Photo of 8 Messina Circle, Methuen, MA 01844 (MLS # 73393076)
    42
     
    8 Messina Circle, Methuen, MA
    8 Messina Circle
    Methuen, MA
    • 5 Beds
    • 2 Baths
    • 3,290 Home (sqft)
    • 2 Baths
    • 20,474 Lot (sqft)
    Listed with Lamacchia Realty, Inc.
  13. Photo of 9 Judith Rd, Worcester, MA 01602 (MLS # 73393079)
    $479,900
    Photo of 9 Judith Rd, Worcester, MA 01602 (MLS # 73393079)
    Photo of 9 Judith Rd, Worcester, MA 01602 (MLS # 73393079)
    33
     
    9 Judith Rd, Worcester, MA
    9 Judith Rd
    Worcester, MA
    • 2 Beds
    • 2 Baths
    • 1,900 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
    Listed with Keller Williams Boston Metrowest
  14. Photo of 70 Fox Meadow Ln, Dedham, MA 02026 (MLS # 73393077)
    $679,900
    Photo of 70 Fox Meadow Ln, Dedham, MA 02026 (MLS # 73393077)
    Photo of 70 Fox Meadow Ln, Dedham, MA 02026 (MLS # 73393077)
    33
     
    70 Fox Meadow Ln, Dedham, MA
    70 Fox Meadow Ln
    Dedham, MA
    • 3 Beds
    • 3 Baths
    • 1,706 Home (sqft)
    • 3 Baths
    • 12,197 Lot (sqft)
    Listed with Donahue Real Estate Co.
  15. Photo of 2104 Hockley Drive #2104, Hingham, MA 02043 (MLS # 73393078)
    $499,900
    Photo of 2104 Hockley Drive #2104, Hingham, MA 02043 (MLS # 73393078)
    Photo of 2104 Hockley Drive #2104, Hingham, MA 02043 (MLS # 73393078)
    29
     
    2104 Hockley Drive #2104, Hingham, MA
    2104 Hockley Drive #2104
    Hingham, MA
    • 2 Beds
    • 1 Bath
    • 936 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  16. Photo of 39 Story St #2, Boston, MA 02127 (MLS # 73393069)
    $609,000
    Photo of 39 Story St #2, Boston, MA 02127 (MLS # 73393069)
    Photo of 39 Story St #2, Boston, MA 02127 (MLS # 73393069)
    17
     
    39 Story St #2, Boston, MA
    39 Story St #2
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 608 Home (sqft)
    • 1 Bath
    • 436 Lot (sqft)
    Listed with Engel & Volkers Boston
  17. Photo of 42 Mccabe Street, Dartmouth, MA 02748 (MLS # 73393061)
    $389,900
    Photo of 42 Mccabe Street, Dartmouth, MA 02748 (MLS # 73393061)
    Photo of 42 Mccabe Street, Dartmouth, MA 02748 (MLS # 73393061)
    20
     
    42 Mccabe Street, Dartmouth, MA
    42 Mccabe Street
    Dartmouth, MA
    • 2 Beds
    • 1 Bath
    • 640 Home (sqft)
    • 1 Bath
    • 3,921 Lot (sqft)
    Listed with RE/MAX Vantage
  18. Photo of 16 Merrills Way, Rowley, MA 01969 (MLS # 73393071)
    $929,000
    Photo of 16 Merrills Way, Rowley, MA 01969 (MLS # 73393071)
    Photo of 16 Merrills Way, Rowley, MA 01969 (MLS # 73393071)
    37
     
    16 Merrills Way, Rowley, MA
    16 Merrills Way
    Rowley, MA
    • 4 Beds
    • 3 Baths
    • 2,428 Home (sqft)
    • 3 Baths
    • 42,254 Lot (sqft)
    Listed with Coldwell Banker Realty - Lexington
  19. Photo of 3302 Briarwood Village #3302, Clinton, MA 01510 (MLS # 73393072)
    $410,000
    Photo of 3302 Briarwood Village #3302, Clinton, MA 01510 (MLS # 73393072)
    Photo of 3302 Briarwood Village #3302, Clinton, MA 01510 (MLS # 73393072)
    31
     
    3302 Briarwood Village #3302, Clinton, MA
    3302 Briarwood Village #3302
    Clinton, MA
    • 2 Beds
    • 2 Baths
    • 1,135 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Worcester
  20. Photo of 94 Kimball Rd, Amesbury, MA 01931 (MLS # 73393066)
    $750,000
    Photo of 94 Kimball Rd, Amesbury, MA 01931 (MLS # 73393066)
    Photo of 94 Kimball Rd, Amesbury, MA 01931 (MLS # 73393066)
    37
     
    94 Kimball Rd, Amesbury, MA
    94 Kimball Rd
    Amesbury, MA
    • 4 Beds
    • 3 Baths
    • 2,235 Home (sqft)
    • 3 Baths
    • 2.01 Lot (ac)
    Listed with Red Post Realty, LLC
  21. Photo of 15 Hillside St, Rowley, MA 01969 (MLS # 73393060)
    $985,000
    Photo of 15 Hillside St, Rowley, MA 01969 (MLS # 73393060)
    Photo of 15 Hillside St, Rowley, MA 01969 (MLS # 73393060)
    41
     
    15 Hillside St, Rowley, MA
    15 Hillside St
    Rowley, MA
    • 4 Beds
    • 3 Baths
    • 3,138 Home (sqft)
    • 3 Baths
    • 40,076 Lot (sqft)
    Listed with Five Mark Realty Group LLC
  22. Photo of 14 Frost Lane, Sudbury, MA 01776 (MLS # 73393068)
    $1,699,000
    Photo of 14 Frost Lane, Sudbury, MA 01776 (MLS # 73393068)
    Photo of 14 Frost Lane, Sudbury, MA 01776 (MLS # 73393068)
    42
     
    14 Frost Lane, Sudbury, MA
    14 Frost Lane
    Sudbury, MA
    • 4 Beds
    • 4 Baths
    • 4,294 Home (sqft)
    • 4 Baths
    • 1.41 Lot (ac)
    Listed with Coldwell Banker Realty - Sudbury
  23. Photo of 45 Main St, Medway, MA 02053 (MLS # 73393073)
    $599,000
    Photo of 45 Main St, Medway, MA 02053 (MLS # 73393073)
    Photo of 45 Main St, Medway, MA 02053 (MLS # 73393073)
    35
     
    45 Main St, Medway, MA
    45 Main St
    Medway, MA
    • 3 Beds
    • 2 Baths
    • 1,875 Home (sqft)
    • 2 Baths
    • 26,136 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Page Realty
  24. Photo of 176 Medford St #176, Arlington, MA 02474 (MLS # 73393070)
    $1,150,000
    Photo of 176 Medford St #176, Arlington, MA 02474 (MLS # 73393070)
    Photo of 176 Medford St #176, Arlington, MA 02474 (MLS # 73393070)
    38
     
    176 Medford St #176, Arlington, MA
    176 Medford St #176
    Arlington, MA
    • 4 Beds
    • 3 Baths
    • 2,162 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with RE/MAX Way
  25. Photo of 10 Salem St Ave #2, Boston, MA 02129 (MLS # 73393063)
    $939,000
    Photo of 10 Salem St Ave #2, Boston, MA 02129 (MLS # 73393063)
    Photo of 10 Salem St Ave #2, Boston, MA 02129 (MLS # 73393063)
    16
     
    10 Salem St Ave #2, Boston, MA
    10 Salem St Ave #2
    Boston, MA
    • 3 Beds
    • 1 Bath
    • 1,308 Home (sqft)
    • 1 Bath
    • 1,307 Lot (sqft)
    Listed with Coldwell Banker Realty - Boston
  26. Photo of 9 Country Club Ln #A, Milford, MA 01757 (MLS # 73393058)
    $449,900
    Photo of 9 Country Club Ln #A, Milford, MA 01757 (MLS # 73393058)
    Photo of 9 Country Club Ln #A, Milford, MA 01757 (MLS # 73393058)
    42
     
    9 Country Club Ln #A, Milford, MA
    9 Country Club Ln #A
    Milford, MA
    • 2 Beds
    • 3 Baths
    • 1,567 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Gerry Abbott REALTORS®
  27. Photo of 59 Cutter Lane #59, Amesbury, MA 01913 (MLS # 73393055)
    $924,900
    Photo of 59 Cutter Lane #59, Amesbury, MA 01913 (MLS # 73393055)
    Photo of 59 Cutter Lane #59, Amesbury, MA 01913 (MLS # 73393055)
    42
     
    59 Cutter Lane #59, Amesbury, MA
    59 Cutter Lane #59
    Amesbury, MA
    • 3 Beds
    • 3 Baths
    • 2,530 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Leading Edge Real Estate
  28. Photo of 20 King St, Wilmington, MA 01887 (MLS # 73393057)
    $599,000
    Photo of 20 King St, Wilmington, MA 01887 (MLS # 73393057)
    Photo of 20 King St, Wilmington, MA 01887 (MLS # 73393057)
    20
     
    20 King St, Wilmington, MA
    20 King St
    Wilmington, MA
    • 4 Beds
    • 1 Bath
    • 1,261 Home (sqft)
    • 1 Bath
    • 9,148 Lot (sqft)
    Listed with Cameron Real Estate Group - Framingham
  29. Photo of 86 S Ashburnham Rd, Westminster, MA 01473 (MLS # 73393053)
    $649,900
    Photo of 86 S Ashburnham Rd, Westminster, MA 01473 (MLS # 73393053)
    Photo of 86 S Ashburnham Rd, Westminster, MA 01473 (MLS # 73393053)
    36
     
    86 S Ashburnham Rd, Westminster, MA
    86 S Ashburnham Rd
    Westminster, MA
    • 3 Beds
    • 3 Baths
    • 2,094 Home (sqft)
    • 3 Baths
    • 4.14 Lot (ac)
    Listed with Real Broker MA, LLC
  30. Photo of 99 Oak St, North Attleboro, MA 02760 (MLS # 73393051)
    $480,000
    Photo of 99 Oak St, North Attleboro, MA 02760 (MLS # 73393051)
    Photo of 99 Oak St, North Attleboro, MA 02760 (MLS # 73393051)
    41
     
    99 Oak St, North Attleboro, MA
    99 Oak St
    North Attleboro, MA
    • 2 Beds
    • 2 Baths
    • 1,396 Home (sqft)
    • 2 Baths
    • 17,424 Lot (sqft)
    Listed with eXp Realty
Previous Page 2 of 17 Next

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

This Real Estate IDX is (c) Diverse Solutions 2025. Privacy | Terms & Conditions

 
 

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.

Contact Alexa

Alexa Dealy, Realtor® RE/MAX Andrew Realty Services Hours: 9:00 am – 7:00 pm

Compare listings

Compare
Call Now Button