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 4/21/2025)

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

 
 

Show Map
  • List View
  • Grid View
Sorted by
241 - 270 of 500+ | Previous Page 9 of 17 Next
  1. Photo of 6 Kenmar Dr #8, Billerica, MA 01821 (MLS # 73362209)
    $339,900
    Photo of 6 Kenmar Dr #8, Billerica, MA 01821 (MLS # 73362209)
    Photo of 6 Kenmar Dr #8, Billerica, MA 01821 (MLS # 73362209)
    12
     
    6 Kenmar Dr #8, Billerica, MA
    6 Kenmar Dr #8
    Billerica, MA
    • 2 Beds
    • 1 Bath
    • 800 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with RE/MAX Triumph Realty
  2. Photo of 1251 Sea Street #1251, Quincy, MA 02169 (MLS # 73361805)
    $349,900
    Photo of 1251 Sea Street #1251, Quincy, MA 02169 (MLS # 73361805)
    Photo of 1251 Sea Street #1251, Quincy, MA 02169 (MLS # 73361805)
    24
     
    1251 Sea Street #1251, Quincy, MA
    1251 Sea Street #1251
    Quincy, MA
    • 1 Bed
    • 1 Bath
    • 576 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Blue Marble Group, Inc.
  3. Photo of 19 Father Francis Gilday Street #102, Boston, MA 02118 (MLS # 73361759)
    $955,000
    Photo of 19 Father Francis Gilday Street #102, Boston, MA 02118 (MLS # 73361759)
    Photo of 19 Father Francis Gilday Street #102, Boston, MA 02118 (MLS # 73361759)
    19
     
    19 Father Francis Gilday Street #102, Boston, MA
    19 Father Francis Gilday Street #102
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 961 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with Venture
  4. Photo of 46 Aspen St, Brockton, MA 02302 (MLS # 73361756)
    $495,000
    Photo of 46 Aspen St, Brockton, MA 02302 (MLS # 73361756)
    Photo of 46 Aspen St, Brockton, MA 02302 (MLS # 73361756)
    21
     
    46 Aspen St, Brockton, MA
    46 Aspen St
    Brockton, MA
    • 3 Beds
    • 1 Bath
    • 1,120 Home (sqft)
    • 1 Bath
    • 16,118 Lot (sqft)
    Listed with McCorry Real Estate, LLC
  5. Photo of 33 Queen Anne Road, Harwich, MA 02645 (MLS # 73361753)
    $1,275,000
    Photo of 33 Queen Anne Road, Harwich, MA 02645 (MLS # 73361753)
    Photo of 33 Queen Anne Road, Harwich, MA 02645 (MLS # 73361753)
    41
     
    33 Queen Anne Road, Harwich, MA
    33 Queen Anne Road
    Harwich, MA
    • 4 Beds
    • 3 Baths
    • 2,752 Home (sqft)
    • 3 Baths
    • 30,928 Lot (sqft)
    Listed with Gibson Sotheby's International Realty
  6. Photo of 15 Houghton St #8, Worcester, MA 01604 (MLS # 73361751)
    $249,900
    Photo of 15 Houghton St #8, Worcester, MA 01604 (MLS # 73361751)
    Photo of 15 Houghton St #8, Worcester, MA 01604 (MLS # 73361751)
    15
     
    15 Houghton St #8, Worcester, MA
    15 Houghton St #8
    Worcester, MA
    • 2 Beds
    • 1 Bath
    • 839 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with LAER Realty Partners
  7. Photo of 136 Dartmouth St, New Bedford, MA 02740 (MLS # 73361749)
    $649,999
    Photo of 136 Dartmouth St, New Bedford, MA 02740 (MLS # 73361749)
    Photo of 136 Dartmouth St, New Bedford, MA 02740 (MLS # 73361749)
    15
     
    136 Dartmouth St, New Bedford, MA
    136 Dartmouth St
    New Bedford, MA
    • 9 Beds
    • 3 Baths
    • 3,348 Home (sqft)
    • 3 Baths
    • 3,485 Lot (sqft)
    Listed with Martins & Associates R.E. Inc.
  8. Photo of 126 Kenwood Rd, Dracut, MA 01826 (MLS # 73361748)
    $719,900
    Photo of 126 Kenwood Rd, Dracut, MA 01826 (MLS # 73361748)
    Photo of 126 Kenwood Rd, Dracut, MA 01826 (MLS # 73361748)
    41
     
    126 Kenwood Rd, Dracut, MA
    126 Kenwood Rd
    Dracut, MA
    • 4 Beds
    • 2 Baths
    • 2,056 Home (sqft)
    • 2 Baths
    • 40,511 Lot (sqft)
    Listed with Arcieri Real Estate
  9. Photo of 61-63 Hall St, Springfield, MA 01108 (MLS # 73361746)
    $300,000
    Photo of 61-63 Hall St, Springfield, MA 01108 (MLS # 73361746)
    Photo of 61-63 Hall St, Springfield, MA 01108 (MLS # 73361746)
    30
     
    61-63 Hall St, Springfield, MA
    61-63 Hall St
    Springfield, MA
    • 6 Beds
    • 3 Baths
    • 2,698 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
    Listed with Signature Realty
  10. Photo of 59 School St, Middleboro, MA 02346 (MLS # 73361732)
    $525,000
    Photo of 59 School St, Middleboro, MA 02346 (MLS # 73361732)
    Photo of 59 School St, Middleboro, MA 02346 (MLS # 73361732)
    27
     
    59 School St, Middleboro, MA
    59 School St
    Middleboro, MA
    • 3 Beds
    • 1 Bath
    • 1,140 Home (sqft)
    • 1 Bath
    • 19,602 Lot (sqft)
    Listed with Boston Connect Real Estate
  11. Photo of 686 Brook St, Clinton, MA 01510 (MLS # 73361728)
    $769,000
    Photo of 686 Brook St, Clinton, MA 01510 (MLS # 73361728)
    Photo of 686 Brook St, Clinton, MA 01510 (MLS # 73361728)
    39
     
    686 Brook St, Clinton, MA
    686 Brook St
    Clinton, MA
    • 7 Beds
    • 4 Baths
    • 5,500 Home (sqft)
    • 4 Baths
    • 5,663 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Commonwealth Real Estate
  12. Photo of 15 Rutledge Ave, Springfield, MA 01105 (MLS # 73361727)
    $429,000
    Photo of 15 Rutledge Ave, Springfield, MA 01105 (MLS # 73361727)
    Photo of 15 Rutledge Ave, Springfield, MA 01105 (MLS # 73361727)
    41
     
    15 Rutledge Ave, Springfield, MA
    15 Rutledge Ave
    Springfield, MA
    • 8 Beds
    • 3 Baths
    • 3,231 Home (sqft)
    • 3 Baths
    • 4,356 Lot (sqft)
    Listed with Naples Realty Group
  13. Photo of 123 Green Pond Rd, Falmouth, MA 02536 (MLS # 73361723)
    $2,250,000
    Photo of 123 Green Pond Rd, Falmouth, MA 02536 (MLS # 73361723)
    Photo of 123 Green Pond Rd, Falmouth, MA 02536 (MLS # 73361723)
    42
     
    123 Green Pond Rd, Falmouth, MA
    123 Green Pond Rd
    Falmouth, MA
    • 4 Beds
    • 5 Baths
    • 5,953 Home (sqft)
    • 5 Baths
    • 26,572 Lot (sqft)
    Listed with Sotheby's International Realty
  14. Photo of 54 Ward Ave #54, Easthampton, MA 01027 (MLS # 73361721)
    $389,000
    Photo of 54 Ward Ave #54, Easthampton, MA 01027 (MLS # 73361721)
    Photo of 54 Ward Ave #54, Easthampton, MA 01027 (MLS # 73361721)
    29
     
    54 Ward Ave #54, Easthampton, MA
    54 Ward Ave #54
    Easthampton, MA
    • 3 Beds
    • 2 Baths
    • 1,774 Home (sqft)
    • 2 Baths
    • 8,712 Lot (sqft)
    Listed with Brick & Mortar Northampton
  15. Photo of 32 John Perkins Way, Middleboro, MA 02346 (MLS # 73361716)
    $874,900
    Photo of 32 John Perkins Way, Middleboro, MA 02346 (MLS # 73361716)
    Photo of 32 John Perkins Way, Middleboro, MA 02346 (MLS # 73361716)
    32 John Perkins Way, Middleboro, MA
    32 John Perkins Way
    Middleboro, MA
    • 4 Beds
    • 3 Baths
    • 2,056 Home (sqft)
    • 3 Baths
    • 1.84 Lot (ac)
    Listed with Southbrook Realty Group, Inc
  16. Photo of 56 Fairwood Rd, Yarmouth, MA 02664 (MLS # 73361714)
    $799,900
    Photo of 56 Fairwood Rd, Yarmouth, MA 02664 (MLS # 73361714)
    Photo of 56 Fairwood Rd, Yarmouth, MA 02664 (MLS # 73361714)
    42
     
    56 Fairwood Rd, Yarmouth, MA
    56 Fairwood Rd
    Yarmouth, MA
    • 3 Beds
    • 3 Baths
    • 1,640 Home (sqft)
    • 3 Baths
    • 13,940 Lot (sqft)
    Listed with Majestic Realty Group
  17. Photo of 219 Charles St, Fitchburg, MA 01420 (MLS # 73361710)
    $625,000
    Photo of 219 Charles St, Fitchburg, MA 01420 (MLS # 73361710)
    Photo of 219 Charles St, Fitchburg, MA 01420 (MLS # 73361710)
    41
     
    219 Charles St, Fitchburg, MA
    219 Charles St
    Fitchburg, MA
    • 8 Beds
    • 3 Baths
    • 3,169 Home (sqft)
    • 3 Baths
    • 9,584 Lot (sqft)
    Listed with Prospective Realty INC
  18. Photo of 2 Mariner Way, Nantucket, MA 02564 (MLS # 73361709)
    $6,995,000
    Photo of 2 Mariner Way, Nantucket, MA 02564 (MLS # 73361709)
    Photo of 2 Mariner Way, Nantucket, MA 02564 (MLS # 73361709)
    39
     
    2 Mariner Way, Nantucket, MA
    2 Mariner Way
    Nantucket, MA
    • 4 Beds
    • 6 Baths
    • 3,438 Home (sqft)
    • 6 Baths
    • 4,792 Lot (sqft)
    Listed with EW Doherty Real Estate
  19. Photo of 4 Lawrence Rd, Derry, NH 03038 (MLS # 73361707)
    $450,000
    Photo of 4 Lawrence Rd, Derry, NH 03038 (MLS # 73361707)
    Photo of 4 Lawrence Rd, Derry, NH 03038 (MLS # 73361707)
    38
     
    4 Lawrence Rd, Derry, NH
    4 Lawrence Rd
    Derry, NH
    • 0 Beds
    • 2 Baths
    • 1,133 Home (sqft)
    • 2 Baths
    • 27,443 Lot (sqft)
    Listed with Keller Williams Gateway Realty
  20. Photo of 36 Brewster Rd, Brockton, MA 02301 (MLS # 73361706)
    $569,900
    Photo of 36 Brewster Rd, Brockton, MA 02301 (MLS # 73361706)
    Photo of 36 Brewster Rd, Brockton, MA 02301 (MLS # 73361706)
    18
     
    36 Brewster Rd, Brockton, MA
    36 Brewster Rd
    Brockton, MA
    • 3 Beds
    • 2 Baths
    • 1,224 Home (sqft)
    • 2 Baths
    • 14,375 Lot (sqft)
    Listed with The Greene Realty Group
  21. Photo of 50 S Common Street #104, Lynn, MA 01902 (MLS # 73361702)
    $325,000
    Photo of 50 S Common Street #104, Lynn, MA 01902 (MLS # 73361702)
    Photo of 50 S Common Street #104, Lynn, MA 01902 (MLS # 73361702)
    19
     
    50 S Common Street #104, Lynn, MA
    50 S Common Street #104
    Lynn, MA
    • 1 Bed
    • 1 Bath
    • 850 Home (sqft)
    • 1 Bath
    • 0 Lot (sqft)
    Listed with RE/MAX Renaissance Inc.
  22. Photo of 23 Beechwood Dr, Haverhill, MA 01832 (MLS # 73361700)
    $675,000
    Photo of 23 Beechwood Dr, Haverhill, MA 01832 (MLS # 73361700)
    Photo of 23 Beechwood Dr, Haverhill, MA 01832 (MLS # 73361700)
    39
     
    23 Beechwood Dr, Haverhill, MA
    23 Beechwood Dr
    Haverhill, MA
    • 3 Beds
    • 3 Baths
    • 1,788 Home (sqft)
    • 3 Baths
    • 30,928 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Verani Realty
  23. Photo of 416 Seaver St #6, Boston, MA 02121 (MLS # 73361697)
    $375,000
    Photo of 416 Seaver St #6, Boston, MA 02121 (MLS # 73361697)
    Photo of 416 Seaver St #6, Boston, MA 02121 (MLS # 73361697)
    14
     
    416 Seaver St #6, Boston, MA
    416 Seaver St #6
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 712 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
    Listed with Clements Realty Group
  24. Photo of 77 Pells Fishing Rd, Brewster, MA 02631 (MLS # 73361696)
    $950,000
    Photo of 77 Pells Fishing Rd, Brewster, MA 02631 (MLS # 73361696)
    Photo of 77 Pells Fishing Rd, Brewster, MA 02631 (MLS # 73361696)
    36
     
    77 Pells Fishing Rd, Brewster, MA
    77 Pells Fishing Rd
    Brewster, MA
    • 3 Beds
    • 4 Baths
    • 1,625 Home (sqft)
    • 4 Baths
    • 29,186 Lot (sqft)
    Listed with Kinlin Grover Compass
  25. Photo of 94-96 Hamilton Street, Worcester, MA 01604 (MLS # 73361694)
    $1,050,000
    Photo of 94-96 Hamilton Street, Worcester, MA 01604 (MLS # 73361694)
    Photo of 94-96 Hamilton Street, Worcester, MA 01604 (MLS # 73361694)
    42
     
    94-96 Hamilton Street, Worcester, MA
    94-96 Hamilton Street
    Worcester, MA
    • 9 Beds
    • 5 Baths
    • 5,402 Home (sqft)
    • 5 Baths
    • 4,356 Lot (sqft)
    Listed with RE/MAX Partners
  26. Photo of 21 - 23 Hartford Ave S, Upton, MA 01568 (MLS # 73361683)
    $460,000
    Photo of 21 - 23 Hartford Ave S, Upton, MA 01568 (MLS # 73361683)
    Photo of 21 - 23 Hartford Ave S, Upton, MA 01568 (MLS # 73361683)
    39
     
    21 - 23 Hartford Ave S, Upton, MA
    21 - 23 Hartford Ave S
    Upton, MA
    • 6 Beds
    • 2 Baths
    • 2,605 Home (sqft)
    • 2 Baths
    • 20,474 Lot (sqft)
    Listed with Berkshire Hathaway HomeServices Page Realty
  27. Photo of 12 Spencer St, Boston, MA 02124 (MLS # 73361675)
    $949,900
    Photo of 12 Spencer St, Boston, MA 02124 (MLS # 73361675)
    Photo of 12 Spencer St, Boston, MA 02124 (MLS # 73361675)
    27
     
    12 Spencer St, Boston, MA
    12 Spencer St
    Boston, MA
    • 6 Beds
    • 3 Baths
    • 3,672 Home (sqft)
    • 3 Baths
    • 3,921 Lot (sqft)
    Listed with Keller Williams Realty
  28. Photo of 26 Russell St #A-B, Hadley, MA 01035 (MLS # 73361670)
    $1,299,000
    Photo of 26 Russell St #A-B, Hadley, MA 01035 (MLS # 73361670)
    Photo of 26 Russell St #A-B, Hadley, MA 01035 (MLS # 73361670)
    42
     
    26 Russell St #A-B, Hadley, MA
    26 Russell St #A-B
    Hadley, MA
    • 3 Beds
    • 5 Baths
    • 5,000 Home (sqft)
    • 5 Baths
    • 17,860 Lot (sqft)
    Listed with Signature Realty
  29. Photo of 325 Walnut St, Lynnfield, MA 01940 (MLS # 73361672)
    $1,599,000
    Photo of 325 Walnut St, Lynnfield, MA 01940 (MLS # 73361672)
    Photo of 325 Walnut St, Lynnfield, MA 01940 (MLS # 73361672)
    17
     
    325 Walnut St, Lynnfield, MA
    325 Walnut St
    Lynnfield, MA
    • 4 Beds
    • 4 Baths
    • 3,225 Home (sqft)
    • 4 Baths
    • 30,492 Lot (sqft)
    Listed with Littlefield Real Estate, LLC
  30. Photo of 4 Bishops Park #4, Mashpee, MA 02649 (MLS # 73361664)
    $557,000
    Photo of 4 Bishops Park #4, Mashpee, MA 02649 (MLS # 73361664)
    Photo of 4 Bishops Park #4, Mashpee, MA 02649 (MLS # 73361664)
    17
     
    4 Bishops Park #4, Mashpee, MA
    4 Bishops Park #4
    Mashpee, MA
    • 2 Beds
    • 3 Baths
    • 1,906 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Decoy Realty LTD
Previous Page 9 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 Software 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