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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 7/9/2025)

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  1. Photo of 35 Ridge Road, Wrentham, MA 02093 (MLS # 73402006)
    $1,299,900
    Photo of 35 Ridge Road, Wrentham, MA 02093 (MLS # 73402006)
    Photo of 35 Ridge Road, Wrentham, MA 02093 (MLS # 73402006)
    42
     
    35 Ridge Road, Wrentham, MA
    35 Ridge Road
    Wrentham, MA
    • 4 Beds
    • 4 Baths
    • 4,436 Home (sqft)
    • 4 Baths
    • 30,057 Lot (sqft)
    Listed with Coldwell Banker Realty - Franklin
  2. Photo of 171 Puritan Road, Bourne, MA 02532 (MLS # 73401990)
    $894,900
    Photo of 171 Puritan Road, Bourne, MA 02532 (MLS # 73401990)
    Photo of 171 Puritan Road, Bourne, MA 02532 (MLS # 73401990)
    42
     
    171 Puritan Road, Bourne, MA
    171 Puritan Road
    Bourne, MA
    • 4 Beds
    • 5 Baths
    • 3,755 Home (sqft)
    • 5 Baths
    • 37,898 Lot (sqft)
    Listed with Coldwell Banker Realty - Plymouth
  3. Photo of 43 Carver Road, Newton, MA 02461 (MLS # 73402002)
    $6,198,000
    Photo of 43 Carver Road, Newton, MA 02461 (MLS # 73402002)
    Photo of 43 Carver Road, Newton, MA 02461 (MLS # 73402002)
    42
     
    43 Carver Road, Newton, MA
    43 Carver Road
    Newton, MA
    • 7 Beds
    • 8 Baths
    • 10,400 Home (sqft)
    • 8 Baths
    • 23,958 Lot (sqft)
    Listed with Coldwell Banker Realty - Newton
  4. Photo of 12 Russell Rd #405, Wellesley, MA 02482 (MLS # 73402005)
    $925,000
    Photo of 12 Russell Rd #405, Wellesley, MA 02482 (MLS # 73402005)
    Photo of 12 Russell Rd #405, Wellesley, MA 02482 (MLS # 73402005)
    34
     
    12 Russell Rd #405, Wellesley, MA
    12 Russell Rd #405
    Wellesley, MA
    • 2 Beds
    • 2 Baths
    • 1,165 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Douglas Elliman Real Estate - Park Plaza
  5. Photo of 38 Juniper Street, Boston, MA 02119 (MLS # 73402004)
    $1,200,000
    Photo of 38 Juniper Street, Boston, MA 02119 (MLS # 73402004)
    Photo of 38 Juniper Street, Boston, MA 02119 (MLS # 73402004)
    34
     
    38 Juniper Street, Boston, MA
    38 Juniper Street
    Boston, MA
    • 7 Beds
    • 2 Baths
    • 3,398 Home (sqft)
    • 2 Baths
    • 4,356 Lot (sqft)
    Listed with Boardwalk Properties
  6. Photo of 25 Tracey Ln, East Longmeadow, MA 01028 (MLS # 73401998)
    $484,900
    Photo of 25 Tracey Ln, East Longmeadow, MA 01028 (MLS # 73401998)
    Photo of 25 Tracey Ln, East Longmeadow, MA 01028 (MLS # 73401998)
    40
     
    25 Tracey Ln, East Longmeadow, MA
    25 Tracey Ln
    East Longmeadow, MA
    • 3 Beds
    • 2 Baths
    • 1,236 Home (sqft)
    • 2 Baths
    • 37,898 Lot (sqft)
    Listed with Executive Real Estate, Inc.
  7. Photo of 4 Rileys Way, Dartmouth, MA 02747 (MLS # 73401995)
    $998,683
    Photo of 4 Rileys Way, Dartmouth, MA 02747 (MLS # 73401995)
    Photo of 4 Rileys Way, Dartmouth, MA 02747 (MLS # 73401995)
    33
     
    4 Rileys Way, Dartmouth, MA
    4 Rileys Way
    Dartmouth, MA
    • 3 Beds
    • 3 Baths
    • 3,372 Home (sqft)
    • 3 Baths
    • 1.49 Lot (ac)
    Listed with Amaral & Associates RE
  8. Photo of 67 Moscow Rd, Holden, MA 01522 (MLS # 73401994)
    $975,000
    Photo of 67 Moscow Rd, Holden, MA 01522 (MLS # 73401994)
    Photo of 67 Moscow Rd, Holden, MA 01522 (MLS # 73401994)
    41
     
    67 Moscow Rd, Holden, MA
    67 Moscow Rd
    Holden, MA
    • 4 Beds
    • 3 Baths
    • 4,510 Home (sqft)
    • 3 Baths
    • 3.88 Lot (ac)
    Listed with Keller Williams Pinnacle Central
  9. Photo of 31 Durbeck Rd, Rockland, MA 02370 (MLS # 73402000)
    $595,000
    Photo of 31 Durbeck Rd, Rockland, MA 02370 (MLS # 73402000)
    Photo of 31 Durbeck Rd, Rockland, MA 02370 (MLS # 73402000)
    25
     
    31 Durbeck Rd, Rockland, MA
    31 Durbeck Rd
    Rockland, MA
    • 3 Beds
    • 2 Baths
    • 1,260 Home (sqft)
    • 2 Baths
    • 13,068 Lot (sqft)
    Listed with William Raveis R.E. & Home Services
  10. Photo of 20 Josiah Path, Falmouth, MA 02540 (MLS # 73401999)
    $1,350,000
    Photo of 20 Josiah Path, Falmouth, MA 02540 (MLS # 73401999)
    Photo of 20 Josiah Path, Falmouth, MA 02540 (MLS # 73401999)
    20 Josiah Path, Falmouth, MA
    20 Josiah Path
    Falmouth, MA
    • 3 Beds
    • 3 Baths
    • 2,000 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
    Listed with Grade A Realty
  11. Photo of 30 Lantern Ln, Randolph, MA 02368 (MLS # 73401992)
    $575,000
    Photo of 30 Lantern Ln, Randolph, MA 02368 (MLS # 73401992)
    Photo of 30 Lantern Ln, Randolph, MA 02368 (MLS # 73401992)
    40
     
    30 Lantern Ln, Randolph, MA
    30 Lantern Ln
    Randolph, MA
    • 3 Beds
    • 2 Baths
    • 1,886 Home (sqft)
    • 2 Baths
    • 16,118 Lot (sqft)
    Listed with The Firm
  12. Photo of 129 Beacon Street #PH, Boston, MA 02116 (MLS # 73401993)
    $2,699,000
    Photo of 129 Beacon Street #PH, Boston, MA 02116 (MLS # 73401993)
    Photo of 129 Beacon Street #PH, Boston, MA 02116 (MLS # 73401993)
    40
     
    129 Beacon Street #PH, Boston, MA
    129 Beacon Street #PH
    Boston, MA
    • 3 Beds
    • 3 Baths
    • 2,169 Home (sqft)
    • 3 Baths
    • 0 Lot (sqft)
    Listed with Compass
  13. Photo of 1975 Middlesex St #10, Lowell, MA 01851 (MLS # 73401987)
    $549,900
    Photo of 1975 Middlesex St #10, Lowell, MA 01851 (MLS # 73401987)
    Photo of 1975 Middlesex St #10, Lowell, MA 01851 (MLS # 73401987)
    11
     
    1975 Middlesex St #10, Lowell, MA
    1975 Middlesex St #10
    Lowell, MA
    • 2 Beds
    • 2 Baths
    • 1,395 Home (sqft)
    • 2 Baths
    • 0 Lot (sqft)
    Listed with Hancock Realty Group LLC
  14. Photo of Lot A Bluestone Avenue, Westport, MA 02790 (MLS # 73401988)
    $1,199,000
    Photo of Lot A Bluestone Avenue, Westport, MA 02790 (MLS # 73401988)
    Photo of Lot A Bluestone Avenue, Westport, MA 02790 (MLS # 73401988)
    Lot A Bluestone Avenue, Westport, MA
    Lot A Bluestone Avenue
    Westport, MA
    • 5 Beds
    • 5 Baths
    • 5,500 Home (sqft)
    • 5 Baths
    • 1.60 Lot (ac)
    Listed with Century 21 Realty Network
  15. Photo of 46 Foster St, North Andover, MA 01845 (MLS # 73401973)
    $949,900
    Photo of 46 Foster St, North Andover, MA 01845 (MLS # 73401973)
    Photo of 46 Foster St, North Andover, MA 01845 (MLS # 73401973)
    42
     
    46 Foster St, North Andover, MA
    46 Foster St
    North Andover, MA
    • 3 Beds
    • 3 Baths
    • 3,278 Home (sqft)
    • 3 Baths
    • 1.03 Lot (ac)
    Listed with Leading Edge Real Estate
  16. Photo of 28 Rita Drive, Medford, MA 02155 (MLS # 73401979)
    $1,199,988
    Photo of 28 Rita Drive, Medford, MA 02155 (MLS # 73401979)
    Photo of 28 Rita Drive, Medford, MA 02155 (MLS # 73401979)
    36
     
    28 Rita Drive, Medford, MA
    28 Rita Drive
    Medford, MA
    • 4 Beds
    • 3 Baths
    • 3,964 Home (sqft)
    • 3 Baths
    • 8,277 Lot (sqft)
    Listed with Phoenix Realty Group
  17. Photo of 115 Alder Road, Westwood, MA 02090 (MLS # 73401970)
    $1,050,000
    Photo of 115 Alder Road, Westwood, MA 02090 (MLS # 73401970)
    Photo of 115 Alder Road, Westwood, MA 02090 (MLS # 73401970)
    40
     
    115 Alder Road, Westwood, MA
    115 Alder Road
    Westwood, MA
    • 3 Beds
    • 3 Baths
    • 2,491 Home (sqft)
    • 3 Baths
    • 1.15 Lot (ac)
    Listed with Keller Williams Realty Boston South West
  18. Photo of 36 Lorna Rd, Newton, MA 02459 (MLS # 73401968)
    $1,890,000
    Photo of 36 Lorna Rd, Newton, MA 02459 (MLS # 73401968)
    Photo of 36 Lorna Rd, Newton, MA 02459 (MLS # 73401968)
    18
     
    36 Lorna Rd, Newton, MA
    36 Lorna Rd
    Newton, MA
    • 4 Beds
    • 5 Baths
    • 3,096 Home (sqft)
    • 5 Baths
    • 10,019 Lot (sqft)
    Listed with Hillman Homes
  19. Photo of 23 Indian Lane, Franklin, MA 02038 (MLS # 73401977)
    $695,000
    Photo of 23 Indian Lane, Franklin, MA 02038 (MLS # 73401977)
    Photo of 23 Indian Lane, Franklin, MA 02038 (MLS # 73401977)
    42
     
    23 Indian Lane, Franklin, MA
    23 Indian Lane
    Franklin, MA
    • 3 Beds
    • 2 Baths
    • 1,600 Home (sqft)
    • 2 Baths
    • 28,750 Lot (sqft)
    Listed with RE/MAX Executive Realty
  20. Photo of 12 Zamora St, Boston, MA 02130 (MLS # 73401986)
    $2,649,000
    Photo of 12 Zamora St, Boston, MA 02130 (MLS # 73401986)
    Photo of 12 Zamora St, Boston, MA 02130 (MLS # 73401986)
    28
     
    12 Zamora St, Boston, MA
    12 Zamora St
    Boston, MA
    • 6 Beds
    • 4 Baths
    • 4,800 Home (sqft)
    • 4 Baths
    • 11,326 Lot (sqft)
    Listed with Coldwell Banker Realty - Newton
  21. Photo of 19 Hillcrest Ave, Lexington, MA 02420 (MLS # 73401978)
    $1,499,000
    Photo of 19 Hillcrest Ave, Lexington, MA 02420 (MLS # 73401978)
    Photo of 19 Hillcrest Ave, Lexington, MA 02420 (MLS # 73401978)
    34
     
    19 Hillcrest Ave, Lexington, MA
    19 Hillcrest Ave
    Lexington, MA
    • 4 Beds
    • 5 Baths
    • 3,806 Home (sqft)
    • 5 Baths
    • 7,406 Lot (sqft)
    Listed with Keller Williams Realty Boston Northwest
  22. Photo of 85 Brainerd Rd #202, Boston, MA 02134 (MLS # 73401971)
    $835,000
    Photo of 85 Brainerd Rd #202, Boston, MA 02134 (MLS # 73401971)
    Photo of 85 Brainerd Rd #202, Boston, MA 02134 (MLS # 73401971)
    36
     
    85 Brainerd Rd #202, Boston, MA
    85 Brainerd Rd #202
    Boston, MA
    • 2 Beds
    • 2 Baths
    • 1,050 Home (sqft)
    • 2 Baths
    • 872 Lot (sqft)
    Listed with Dreamega International Realty LLC
  23. Photo of 3 White Rd, Wayland, MA 01778 (MLS # 73401983)
    $900,000
    Photo of 3 White Rd, Wayland, MA 01778 (MLS # 73401983)
    Photo of 3 White Rd, Wayland, MA 01778 (MLS # 73401983)
    19
     
    3 White Rd, Wayland, MA
    3 White Rd
    Wayland, MA
    • 3 Beds
    • 2 Baths
    • 1,569 Home (sqft)
    • 2 Baths
    • 23,523 Lot (sqft)
    Listed with Coldwell Banker Realty - Cambridge
  24. Photo of 24 Old Amherst Rd, Sunderland, MA 01375 (MLS # 73401974)
    $439,900
    Photo of 24 Old Amherst Rd, Sunderland, MA 01375 (MLS # 73401974)
    Photo of 24 Old Amherst Rd, Sunderland, MA 01375 (MLS # 73401974)
    39
     
    24 Old Amherst Rd, Sunderland, MA
    24 Old Amherst Rd
    Sunderland, MA
    • 3 Beds
    • 2 Baths
    • 1,160 Home (sqft)
    • 2 Baths
    • 27,879 Lot (sqft)
    Listed with RE/MAX Connections - Greenfield
  25. Photo of 44 Fairview St, Fitchburg, MA 01420 (MLS # 73401963)
    $519,900
    Photo of 44 Fairview St, Fitchburg, MA 01420 (MLS # 73401963)
    Photo of 44 Fairview St, Fitchburg, MA 01420 (MLS # 73401963)
    33
     
    44 Fairview St, Fitchburg, MA
    44 Fairview St
    Fitchburg, MA
    • 5 Beds
    • 3 Baths
    • 2,433 Home (sqft)
    • 3 Baths
    • 13,504 Lot (sqft)
    Listed with Foster-Healey Real Estate
  26. Photo of 12 Ronny Terrace, Peabody, MA 01960 (MLS # 73401962)
    $749,900
    Photo of 12 Ronny Terrace, Peabody, MA 01960 (MLS # 73401962)
    Photo of 12 Ronny Terrace, Peabody, MA 01960 (MLS # 73401962)
    42
     
    12 Ronny Terrace, Peabody, MA
    12 Ronny Terrace
    Peabody, MA
    • 3 Beds
    • 2 Baths
    • 1,706 Home (sqft)
    • 2 Baths
    • 6,970 Lot (sqft)
    Listed with Moore Real Estate Team LLC
  27. Photo of 3 Antoria Way, Topsfield, MA 01983 (MLS # 73401960)
    $1,299,000
    Photo of 3 Antoria Way, Topsfield, MA 01983 (MLS # 73401960)
    Photo of 3 Antoria Way, Topsfield, MA 01983 (MLS # 73401960)
    40
     
    3 Antoria Way, Topsfield, MA
    3 Antoria Way
    Topsfield, MA
    • 6 Beds
    • 3 Baths
    • 3,612 Home (sqft)
    • 3 Baths
    • 1.19 Lot (ac)
    Listed with Lamacchia Realty, Inc.
  28. Photo of 345 Commonwealth Ave #1A, Boston, MA 02115 (MLS # 73401959)
    $825,000
    Photo of 345 Commonwealth Ave #1A, Boston, MA 02115 (MLS # 73401959)
    Photo of 345 Commonwealth Ave #1A, Boston, MA 02115 (MLS # 73401959)
    31
     
    345 Commonwealth Ave #1A, Boston, MA
    345 Commonwealth Ave #1A
    Boston, MA
    • 2 Beds
    • 1 Bath
    • 683 Home (sqft)
    • 1 Bath
    • 872 Lot (sqft)
    Listed with Coldwell Banker Realty - Brookline
  29. Photo of 253 Needham St, Dedham, MA 02026 (MLS # 73401956)
    $849,000
    Photo of 253 Needham St, Dedham, MA 02026 (MLS # 73401956)
    Photo of 253 Needham St, Dedham, MA 02026 (MLS # 73401956)
    34
     
    253 Needham St, Dedham, MA
    253 Needham St
    Dedham, MA
    • 3 Beds
    • 2 Baths
    • 1,887 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
    Listed with Hope McDermott Real Estate
  30. Photo of 17 Revere Circle, Greenfield, MA 01301 (MLS # 73401957)
    $375,000
    Photo of 17 Revere Circle, Greenfield, MA 01301 (MLS # 73401957)
    Photo of 17 Revere Circle, Greenfield, MA 01301 (MLS # 73401957)
    37
     
    17 Revere Circle, Greenfield, MA
    17 Revere Circle
    Greenfield, MA
    • 3 Beds
    • 2 Baths
    • 1,872 Home (sqft)
    • 2 Baths
    • 17,424 Lot (sqft)
    Listed with Cohn & Company
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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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