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 6/20/2025)

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

 
 

Show Map
  • List View
  • Grid View
Sorted by
271 - 300 of 500+ | Previous Page 10 of 17 Next
  1. Photo of 3 Rosewood Lane, Hingham, MA 02043 (MLS # 73394105)
    $2,599,000
    Photo of 3 Rosewood Lane, Hingham, MA 02043 (MLS # 73394105)
    Photo of 3 Rosewood Lane, Hingham, MA 02043 (MLS # 73394105)
    42
     
    3 Rosewood Lane, Hingham, MA
    3 Rosewood Lane
    Hingham, MA
    • 4 Beds
    • 4 Baths
    • 5,527 Home (sqft)
    • 4 Baths
    • 30,057 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  2. Photo of 137 Brook St, Haverhill, MA 01830 (MLS # 73394106)
    $469,900
    Photo of 137 Brook St, Haverhill, MA 01830 (MLS # 73394106)
    Photo of 137 Brook St, Haverhill, MA 01830 (MLS # 73394106)
    42
     
    137 Brook St, Haverhill, MA
    137 Brook St
    Haverhill, MA
    • 2 Beds
    • 2 Baths
    • 1,221 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
    Listed with RE/MAX Synergy
  3. Photo of 22 Marengo St #22, North Andover, MA 01845 (MLS # 73394102)
    $539,900
    Photo of 22 Marengo St #22, North Andover, MA 01845 (MLS # 73394102)
    Photo of 22 Marengo St #22, North Andover, MA 01845 (MLS # 73394102)
    39
     
    22 Marengo St #22, North Andover, MA
    22 Marengo St #22
    North Andover, MA
    • 2 Beds
    • 3 Baths
    • 2,046 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Realty
  4. Photo of 22 Newton Ave, Tewksbury, MA 01876 (MLS # 73394101)
    $629,000
    Photo of 22 Newton Ave, Tewksbury, MA 01876 (MLS # 73394101)
    Photo of 22 Newton Ave, Tewksbury, MA 01876 (MLS # 73394101)
    41
     
    22 Newton Ave, Tewksbury, MA
    22 Newton Ave
    Tewksbury, MA
    • 5 Beds
    • 2 Baths
    • 2,579 Home (sqft)
    • 2 Baths
    • 11,326 Lot (sqft)
    Listed with Crimson Real Estate Agency, LLC
  5. Photo of 33 Minot St #33, Reading, MA 01867 (MLS # 73394104)
    $550,000
    Photo of 33 Minot St #33, Reading, MA 01867 (MLS # 73394104)
    Photo of 33 Minot St #33, Reading, MA 01867 (MLS # 73394104)
    40
     
    33 Minot St #33, Reading, MA
    33 Minot St #33
    Reading, MA
    • 2 Beds
    • 2 Baths
    • 1,390 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with ERA Key Realty Services
  6. Photo of 216 Water Street #B101, Plymouth, MA 02360 (MLS # 73394097)
    $679,000
    Photo of 216 Water Street #B101, Plymouth, MA 02360 (MLS # 73394097)
    Photo of 216 Water Street #B101, Plymouth, MA 02360 (MLS # 73394097)
    18
     
    216 Water Street #B101, Plymouth, MA
    216 Water Street #B101
    Plymouth, MA
    • 2 Beds
    • 1 Bath
    • 1,104 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Heritage Companies R.E.Brokerage Inc.
  7. Photo of 25 Sunset Drive, Taunton, MA 02780 (MLS # 73394098)
    $659,900
    Photo of 25 Sunset Drive, Taunton, MA 02780 (MLS # 73394098)
    Photo of 25 Sunset Drive, Taunton, MA 02780 (MLS # 73394098)
    40
     
    25 Sunset Drive, Taunton, MA
    25 Sunset Drive
    Taunton, MA
    • 3 Beds
    • 3 Baths
    • 2,066 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Coldwell Banker Realty - Easton
  8. Photo of 60 Ruggles Street, Westborough, MA 01581 (MLS # 73394096)
    $799,900
    Photo of 60 Ruggles Street, Westborough, MA 01581 (MLS # 73394096)
    Photo of 60 Ruggles Street, Westborough, MA 01581 (MLS # 73394096)
    42
     
    60 Ruggles Street, Westborough, MA
    60 Ruggles Street
    Westborough, MA
    • 5 Beds
    • 3 Baths
    • 3,171 Home (sqft)
    • 3 Baths
    • 29,621 Lot (sqft)
    Listed with Gibbs Realty Inc.
  9. Photo of 31 Dix Rd Ext, Woburn, MA 01801 (MLS # 73394095)
    $550,000
    Photo of 31 Dix Rd Ext, Woburn, MA 01801 (MLS # 73394095)
    Photo of 31 Dix Rd Ext, Woburn, MA 01801 (MLS # 73394095)
    22
     
    31 Dix Rd Ext, Woburn, MA
    31 Dix Rd Ext
    Woburn, MA
    • 3 Beds
    • 2 Baths
    • 1,812 Home (sqft)
    • 2 Baths
    • 19,167 Lot (sqft)
    Listed with Leading Edge Real Estate
  10. Photo of 150 Orleans Street #PH1, Boston, MA 02128 (MLS # 73394093)
    $1,299,000
    Photo of 150 Orleans Street #PH1, Boston, MA 02128 (MLS # 73394093)
    Photo of 150 Orleans Street #PH1, Boston, MA 02128 (MLS # 73394093)
    41
     
    150 Orleans Street #PH1, Boston, MA
    150 Orleans Street #PH1
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,019 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Perlera Real Estate
  11. Photo of 25 Jessica Dr #F, Stoughton, MA 02072 (MLS # 73394090)
    $374,900
    Photo of 25 Jessica Dr #F, Stoughton, MA 02072 (MLS # 73394090)
    Photo of 25 Jessica Dr #F, Stoughton, MA 02072 (MLS # 73394090)
    24
     
    25 Jessica Dr #F, Stoughton, MA
    25 Jessica Dr #F
    Stoughton, MA
    • 2 Beds
    • 2 Baths
    • 1,250 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with RE/MAX Distinct Advantage
  12. Photo of 19 Birch St, Millis, MA 02054 (MLS # 73394092)
    $749,900
    Photo of 19 Birch St, Millis, MA 02054 (MLS # 73394092)
    Photo of 19 Birch St, Millis, MA 02054 (MLS # 73394092)
    42
     
    19 Birch St, Millis, MA
    19 Birch St
    Millis, MA
    • 3 Beds
    • 3 Baths
    • 2,273 Home (sqft)
    • 3 Baths
    • 1.25 Lot (ac)
    Listed with Berkshire Hathaway HomeServices Page Realty
  13. Photo of 85 Lynde Street, Melrose, MA 02176 (MLS # 73394087)
    $1,099,000
    Photo of 85 Lynde Street, Melrose, MA 02176 (MLS # 73394087)
    Photo of 85 Lynde Street, Melrose, MA 02176 (MLS # 73394087)
    40
     
    85 Lynde Street, Melrose, MA
    85 Lynde Street
    Melrose, MA
    • 5 Beds
    • 3 Baths
    • 3,100 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
    Listed with J. Mulkerin Realty
  14. Photo of 34 Lewis Ave #34, Arlington, MA 02474 (MLS # 73394089)
    $1,200,000
    Photo of 34 Lewis Ave #34, Arlington, MA 02474 (MLS # 73394089)
    Photo of 34 Lewis Ave #34, Arlington, MA 02474 (MLS # 73394089)
    35
     
    34 Lewis Ave #34, Arlington, MA
    34 Lewis Ave #34
    Arlington, MA
    • 4 Beds
    • 3 Baths
    • 2,748 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Real Broker MA, LLC
  15. Photo of 45 Westmoreland St, Boston, MA 02124 (MLS # 73394080)
    $1,190,000
    Photo of 45 Westmoreland St, Boston, MA 02124 (MLS # 73394080)
    Photo of 45 Westmoreland St, Boston, MA 02124 (MLS # 73394080)
    42
     
    45 Westmoreland St, Boston, MA
    45 Westmoreland St
    Boston, MA
    • 6 Beds
    • 4 Baths
    • 3,225 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
    Listed with Preservation Properties
  16. Photo of 23 Morgan Lane #23, Norton, MA 02766 (MLS # 73394088)
    $379,900
    Photo of 23 Morgan Lane #23, Norton, MA 02766 (MLS # 73394088)
    Photo of 23 Morgan Lane #23, Norton, MA 02766 (MLS # 73394088)
    28
     
    23 Morgan Lane #23, Norton, MA
    23 Morgan Lane #23
    Norton, MA
    • 2 Beds
    • 2 Baths
    • 1,334 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Elite
  17. Photo of 33A Stacey Street #A, Natick, MA 01760 (MLS # 73394079)
    $1,488,000
    Photo of 33A Stacey Street #A, Natick, MA 01760 (MLS # 73394079)
    Photo of 33A Stacey Street #A, Natick, MA 01760 (MLS # 73394079)
    33A Stacey Street #A, Natick, MA
    33A Stacey Street #A
    Natick, MA
    • 4 Beds
    • 5 Baths
    • 3,877 Home (sqft)
    • 5 Baths
    • 12,633 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  18. Photo of 17 Kingsley Rd, Norton, MA 02766 (MLS # 73394075)
    $599,900
    Photo of 17 Kingsley Rd, Norton, MA 02766 (MLS # 73394075)
    Photo of 17 Kingsley Rd, Norton, MA 02766 (MLS # 73394075)
    37
     
    17 Kingsley Rd, Norton, MA
    17 Kingsley Rd
    Norton, MA
    • 3 Beds
    • 1 Bath
    • 1,680 Home (sqft)
    • 1 Bath
    • 17,860 Lot (sqft)
    Listed with Philip Renzi
  19. Photo of 336 Russellville Road, Westfield, MA 01085 (MLS # 73394071)
    $2,300,000
    Photo of 336 Russellville Road, Westfield, MA 01085 (MLS # 73394071)
    Photo of 336 Russellville Road, Westfield, MA 01085 (MLS # 73394071)
    18
     
    336 Russellville Road, Westfield, MA
    336 Russellville Road
    Westfield, MA
    • 3 Beds
    • 4 Baths
    • 1,456 Home (sqft)
    • 4 Baths
    • 66.00 Lot (ac)
    Listed with RE/MAX Compass
  20. Photo of 101 Drummer Rd #101, Acton, MA 01720 (MLS # 73394069)
    $499,000
    Photo of 101 Drummer Rd #101, Acton, MA 01720 (MLS # 73394069)
    Photo of 101 Drummer Rd #101, Acton, MA 01720 (MLS # 73394069)
    23
     
    101 Drummer Rd #101, Acton, MA
    101 Drummer Rd #101
    Acton, MA
    • 2 Beds
    • 2 Baths
    • 1,415 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Keller Williams Realty-Merrimack
  21. Photo of 169 Lyman Rd, Berlin, MA 01503 (MLS # 73394064)
    $735,000
    Photo of 169 Lyman Rd, Berlin, MA 01503 (MLS # 73394064)
    Photo of 169 Lyman Rd, Berlin, MA 01503 (MLS # 73394064)
    41
     
    169 Lyman Rd, Berlin, MA
    169 Lyman Rd
    Berlin, MA
    • 4 Beds
    • 4 Baths
    • 2,208 Home (sqft)
    • 4 Baths
    • 5.54 Lot (ac)
    Listed with Bridge Realty
  22. Photo of 50 Union Place, Braintree, MA 02184 (MLS # 73394068)
    $849,900
    Photo of 50 Union Place, Braintree, MA 02184 (MLS # 73394068)
    Photo of 50 Union Place, Braintree, MA 02184 (MLS # 73394068)
    40
     
    50 Union Place, Braintree, MA
    50 Union Place
    Braintree, MA
    • 3 Beds
    • 2 Baths
    • 2,299 Home (sqft)
    • 2 Baths
    • 10,890 Lot (sqft)
    Listed with Coldwell Banker Realty - Hingham
  23. Photo of 64 E Old Princeton Rd, Hubbardston, MA 01452 (MLS # 73394070)
    $425,000
    Photo of 64 E Old Princeton Rd, Hubbardston, MA 01452 (MLS # 73394070)
    Photo of 64 E Old Princeton Rd, Hubbardston, MA 01452 (MLS # 73394070)
    30
     
    64 E Old Princeton Rd, Hubbardston, MA
    64 E Old Princeton Rd
    Hubbardston, MA
    • 4 Beds
    • 1 Bath
    • 1,248 Home (sqft)
    • 1 Bath
    • 13,068 Lot (sqft)
    Listed with RE/MAX Vision
  24. Photo of 52 Mill Rd, Sandwich, MA 02537 (MLS # 73394062)
    $629,000
    Photo of 52 Mill Rd, Sandwich, MA 02537 (MLS # 73394062)
    Photo of 52 Mill Rd, Sandwich, MA 02537 (MLS # 73394062)
    36
     
    52 Mill Rd, Sandwich, MA
    52 Mill Rd
    Sandwich, MA
    • 3 Beds
    • 2 Baths
    • 1,638 Home (sqft)
    • 2 Baths
    • 14,811 Lot (sqft)
    Listed with Kinlin Grover Compass
  25. Photo of 426 Moraine St, Brockton, MA 02301 (MLS # 73394056)
    $509,900
    Photo of 426 Moraine St, Brockton, MA 02301 (MLS # 73394056)
    Photo of 426 Moraine St, Brockton, MA 02301 (MLS # 73394056)
    38
     
    426 Moraine St, Brockton, MA
    426 Moraine St
    Brockton, MA
    • 3 Beds
    • 1 Bath
    • 1,786 Home (sqft)
    • 1 Bath
    • 10,019 Lot (sqft)
    Listed with Coldwell Banker Realty - Dorchester
  26. Photo of 148-150 Pleasant Street, Boston, MA 02125 (MLS # 73394054)
    $2,500,000
    Photo of 148-150 Pleasant Street, Boston, MA 02125 (MLS # 73394054)
    Photo of 148-150 Pleasant Street, Boston, MA 02125 (MLS # 73394054)
    17
     
    148-150 Pleasant Street, Boston, MA
    148-150 Pleasant Street
    Boston, MA
    • 6 Beds
    • 6 Baths
    • 3,592 Home (sqft)
    • 6 Baths
    • 3,485 Lot (sqft)
    Listed with Boston Realty Advisors
  27. Photo of 53 Richards Rd, Southborough, MA 01772 (MLS # 73394055)
    $1,199,900
    Photo of 53 Richards Rd, Southborough, MA 01772 (MLS # 73394055)
    Photo of 53 Richards Rd, Southborough, MA 01772 (MLS # 73394055)
    42
     
    53 Richards Rd, Southborough, MA
    53 Richards Rd
    Southborough, MA
    • 4 Beds
    • 4 Baths
    • 3,458 Home (sqft)
    • 4 Baths
    • 27,443 Lot (sqft)
    Listed with RE/MAX Signature Properties
  28. Photo of 156 Langen Rd, Lancaster, MA 01523 (MLS # 73394057)
    $649,000
    Photo of 156 Langen Rd, Lancaster, MA 01523 (MLS # 73394057)
    Photo of 156 Langen Rd, Lancaster, MA 01523 (MLS # 73394057)
    26
     
    156 Langen Rd, Lancaster, MA
    156 Langen Rd
    Lancaster, MA
    • 3 Beds
    • 3 Baths
    • 2,712 Home (sqft)
    • 3 Baths
    • 21.00 Lot (ac)
    Listed with The Mitchell Group
  29. Photo of 152 Pleasant Street, Boston, MA 02125 (MLS # 73394059)
    $1,225,000
    Photo of 152 Pleasant Street, Boston, MA 02125 (MLS # 73394059)
    Photo of 152 Pleasant Street, Boston, MA 02125 (MLS # 73394059)
    17
     
    152 Pleasant Street, Boston, MA
    152 Pleasant Street
    Boston, MA
    • 3 Beds
    • 3 Baths
    • 1,800 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
    Listed with Boston Realty Advisors
  30. Photo of 10 Brewster St, Plymouth, MA 02360 (MLS # 73394061)
    $995,000
    Photo of 10 Brewster St, Plymouth, MA 02360 (MLS # 73394061)
    Photo of 10 Brewster St, Plymouth, MA 02360 (MLS # 73394061)
    42
     
    10 Brewster St, Plymouth, MA
    10 Brewster St
    Plymouth, MA
    • 3 Beds
    • 3 Baths
    • 3,000 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
    Listed with Tarantino Real Estate
Previous Page 10 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 IDX Solution 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