West Side Homes

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  /42

  $1,700,000

  Sold May 01, 2026

  114 Johnson Rd, Winchester, MA 01890

  • 3 Beds
  • 3 Baths
  • 3,182 Sq Ft
  • Built 1880

  Last Sold Summary

  • 5% Below List Price
  • $534/SF
  • 22 Days On Market

  Current Estimated Value $1,696,035

  Last Listing Agent Rosemary Kelleher LAER Realty Partners

  114 Johnson Rd, Winchester, MA 01890
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• 

  

  

  /33

  Est $1,762,821

  Not Listed For Sale

  85 Thornberry Rd, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 2,848 Sq Ft
  • Built 1968

  85 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Diane Basemera Coldwell Banker Realty - Newton
• 

  

  

  /42

  $1,599,000

  Open Sat 11AM - 12PM

  • 5 Beds
  • 3 Baths
  • 2,944 Sq Ft

  143 Arlington St, Winchester, MA 01890

  JOIN US FOR AN OPEN HOUSE SATURDAY 9/19 11-12;30! Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases

  Kim Covino Compass

  143 Arlington St, Winchester, MA 01890
• 

  

  

  /42

  $1,550,000

  Sold Oct 31, 2025

  205 Ridge St, Winchester, MA 01890

  • 5 Beds
  • 3 Baths
  • 2,995 Sq Ft
  • Built 1960

  Last Sold Summary

  • $518/SF
  • 5 Days On Market

  Current Estimated Value $1,619,078

  Last Listing Agent Debby Valdes eXp Realty LLC

  205 Ridge St, Winchester, MA 01890
• 

  

  

  /40

  Est $2,008,813

  Not Listed For Sale

  3 Berkshire Dr, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 3,344 Sq Ft
  • Built 1967

  3 Berkshire Dr, Winchester, MA 01890

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Allison Shannon Charlesgate Realty Group, llc
• 

  

  /42

  $3,295,000

  Pending

  • 6 Beds
  • 6.5 Baths
  • 6,100 Sq Ft

  2 Atherton Rd, Winchester, MA 01890

  Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an

  Peter Kasseris Serhant

  2 Atherton Rd, Winchester, MA 01890
• 

  

  /23

  $1,440,150

  Sold Jun 01, 2026

  65 High St, Winchester, MA 01890

  • 6 Beds
  • 3 Baths
  • 2,658 Sq Ft
  • Built 1949

  Last Sold Summary

  • 3% Above List Price
  • $542/SF
  • 5 Days On Market

  Current Estimated Value $1,449,275

  Last Listing Agent Anna Jung K Stadium Realty INC

  65 High St, Winchester, MA 01890
• 

  

  /11

  Est $1,301,828

  Not Listed For Sale

  233 High St, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 2,218 Sq Ft
  • Built 1952

  233 High St, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
• 

  

  /30

  $1,289,000

  Open Sun 1PM - 3PM $211K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,459 Sq Ft

  110 Thornberry Rd, Winchester, MA 01890

  Key upgrades include 200-amp electrical service, a 2021 Brute natural gas boiler and replacement windows. The updated kitchen features stone counters, stainless appliances and a double oven. On Winchester's West Side, this 3-bedroom, 2.5-bath home offers 2,459 sq. ft., including a finished lower level. Enjoy hardwood floors, two fireplaces, central air and a year-round sunroom.The 0.46-acre

  Mark Kiklis Kiklis Real Estate, LLC

  110 Thornberry Rd, Winchester, MA 01890
• 

  

  /38

  $1,655,000

  Sold Aug 13, 2026

  11 Carriage Ln, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,707 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Below List Price
  • $611/SF
  • 9 Days On Market

  Current Estimated Value $1,646,501

  Last Listing Agent Kim Covino Compass

  11 Carriage Ln, Winchester, MA 01890
• 

  

  /40

  Est $1,340,210

  Not Listed For Sale

  134 Johnson Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,430 Sq Ft
  • Built 1977

  134 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Steve Savarese Senne
• 

  

  /42

  $2,450,000

  Open Sat 12PM - 1:30PM $49K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,450 Sq Ft

  54 Squire Rd, Winchester, MA 01890

  Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with

  Anthony Marino The Marino Group Collection

  54 Squire Rd, Winchester, MA 01890
• 

  

  /34

  $2,100,000

  Sold Mar 19, 2026

  10 Hawthorne Rd, Winchester, MA 01890

  • 5 Beds
  • 6 Baths
  • 3,191 Sq Ft
  • Built 1961

  Last Sold Summary

  • 5% Above List Price
  • $658/SF
  • 7 Days On Market

  Current Estimated Value $2,020,776

  Last Listing Agent Susan Kadilak Fiv Realty Co.

  10 Hawthorne Rd, Winchester, MA 01890
• 

  

  /42

  Est $1,814,988

  Not Listed For Sale

  7 Wainwright Rd Unit 98, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,361 Sq Ft
  • Built 1995

  7 Wainwright Rd Unit 98, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group
• 

  

  /36

  $2,195,000

  $104K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 5,006 Sq Ft

  276 High St, Winchester, MA 01890

  Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

  Kim Covino Compass

  276 High St, Winchester, MA 01890
• 

  

  /42

  $1,090,000

  Sold Feb 06, 2026

  16 Ridge St, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft
  • Built 1965

  Last Sold Summary

  • 9% Below List Price
  • $591/SF
  • 82 Days On Market

  Current Estimated Value $1,150,221

  Last Listing Agent Kim Covino Compass

  16 Ridge St, Winchester, MA 01890
• 

  

  /27

  Est $1,332,398

  Not Listed For Sale

  7 Wainwright Rd Unit 22, Winchester, MA 01890

  • 2 Beds
  • 2.5 Baths
  • 3,350 Sq Ft
  • Built 1989

  7 Wainwright Rd Unit 22, Winchester, MA 01890

  Last Sold Summary

  • 183 Days On Market

  Last Listing Agent DeWolfe Group Gibson Sotheby's International Realty
• 

  

  /36

  $3,600,000

  Open Sat 12PM - 1PM

  • 7 Beds
  • 7.5 Baths
  • 7,429 Sq Ft

  11 Viking Rd, Winchester, MA 01890

  Spectacular ground-up NEW construction set on an expansive, level lot of 24,688 square foot lot at the end of a quiet Winchester cul-de-sac. Newly completed and ready for immediate occupancy, this exceptional residence offers more than 7,000 square feet of beautifully finished living space, combining impressive scale, refined design, privacy and convenience just moments from Winchester Country

  Valerie Post Engel & Volkers Boston

  11 Viking Rd, Winchester, MA 01890
• 

  

  /32

  $1,475,000

  Sold Apr 29, 2026

  28 Emerson Rd, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 2,344 Sq Ft
  • Built 1952

  Last Sold Summary

  • 9% Above List Price
  • $629/SF
  • 4 Days On Market

  Current Estimated Value $1,466,943

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  28 Emerson Rd, Winchester, MA 01890
• 

  

  /42

  Est $1,870,330

  Not Listed For Sale

  7 Wainwright Rd Unit 5, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,901 Sq Ft
  • Built 1988

  7 Wainwright Rd Unit 5, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
• 

  

  /37

  $2,250,000

  $250K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 4,071 Sq Ft

  9 Plymouth Rd, Winchester, MA 01890

  Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for

  Stephanie Crawford Real Broker MA, LLC

  9 Plymouth Rd, Winchester, MA 01890
• 

  

  /41

  $1,810,000

  Sold May 18, 2026

  12 Wincrest Dr, Winchester, MA 01890

  • 6 Beds
  • 4.5 Baths
  • 3,833 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Above List Price
  • $472/SF
  • 5 Days On Market

  Current Estimated Value $1,801,279

  Last Listing Agent Kim Covino Compass

  12 Wincrest Dr, Winchester, MA 01890
• 

  

  /41

  Est $1,623,837

  Not Listed For Sale

  7 Wainwright Rd Unit 41, Winchester, MA 01890

  • 2 Beds
  • 4 Baths
  • 5,564 Sq Ft
  • Built 1988

  7 Wainwright Rd Unit 41, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Jill Citrano Leading Edge Real Estate
• 

  

  /28

  $1,713,000

  Sold Sep 26, 2025

  44 Amberwood Dr, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 3,002 Sq Ft
  • Built 1983

  Last Sold Summary

  • 11% Below List Price
  • $571/SF
  • 53 Days On Market

  Current Estimated Value $1,824,555

  Last Listing Agent Hudson Santana Keller Williams Realty Boston Northwest

  44 Amberwood Dr, Winchester, MA 01890
• 

  

  /15

  Est $1,135,855

  Not Listed For Sale

  322 Cambridge St, Winchester, MA 01890

  • 4 Beds
  • 2 Baths
  • 2,172 Sq Ft
  • Built 1985

  322 Cambridge St, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Joanne McDonnell McDonnell Real Estate Group, LLC
• 

  

  /24

  $1,165,000

  Sold Oct 14, 2025

  59 Johnson Rd, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,458 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $474/SF
  • 43 Days On Market

  Current Estimated Value $1,248,283

  Last Listing Agent Angela Zhang Greatland Real Estate LLC

  59 Johnson Rd, Winchester, MA 01890
• 

  

  /42

  Est $2,000,869

  Not Listed For Sale

  40 Wainwright Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,853 Sq Ft
  • Built 1992

  40 Wainwright Rd, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Kim Covino Compass
• 

  

  /41

  $2,150,000

  Sold Nov 05, 2025

  7 Wainwright Rd Unit 72, Winchester, MA 01890

  • 4 Beds
  • 4.5 Baths
  • 3,512 Sq Ft
  • Built 1989

  Last Sold Summary

  • 10% Above List Price
  • $612/SF
  • 7 Days On Market

  Current Estimated Value $2,121,373

  Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

  7 Wainwright Rd Unit 72, Winchester, MA 01890
• 

  

  /42

  Est $2,816,240

  Not Listed For Sale

  19 Socrates Way, Winchester, MA 01890

  • 5 Beds
  • 6 Baths
  • 5,678 Sq Ft
  • Built 1994

  19 Socrates Way, Winchester, MA 01890

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Lucille Murray Better Homes and Gardens Real Estate - The Shanahan Group
• 

  

  /33

  $1,502,500

  Sold Jan 10, 2026

  7 Wainwright Rd Unit 118, Winchester, MA 01890

  • 3 Beds
  • 3.5 Baths
  • 3,807 Sq Ft
  • Built 1995

  Last Sold Summary

  • $395/SF
  • 5 Days On Market

  Current Estimated Value $1,565,871

  Last Listing Agent Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Wainwright Rd Unit 118, Winchester, MA 01890
• 

  

  /42

  Est $2,294,406

  Not Listed For Sale

  17 Wagon Wheel Rd, Winchester, MA 01890

  • 5 Beds
  • 5 Baths
  • 3,940 Sq Ft
  • Built 1983

  17 Wagon Wheel Rd, Winchester, MA 01890

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Yifei Wang Dreamega International Realty LLC
• 

  

  /35

  $1,310,000

  Sold Dec 24, 2025

  7 Thornberry Rd, Winchester, MA 01890

  • 5 Beds
  • 2 Baths
  • 3,033 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Below List Price
  • $432/SF
  • 73 Days On Market

  Current Estimated Value $1,350,775

  Last Listing Agent Kim Covino Compass

  7 Thornberry Rd, Winchester, MA 01890
• 

  

  /42

  Est $1,560,744

  Not Listed For Sale

  21 Johnson Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,814 Sq Ft
  • Built 1970

  21 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest
• 

  

  /40

  $1,515,000

  Sold May 22, 2026

  7 Wainwright Rd Unit 107, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,907 Sq Ft
  • Built 1995

  Last Sold Summary

  • 12% Above List Price
  • $521/SF
  • 8 Days On Market

  Current Estimated Value $1,437,863

  Last Listing Agent Kim Covino Compass

  7 Wainwright Rd Unit 107, Winchester, MA 01890
• 

  

  /36

  Est $2,303,255

  Not Listed For Sale

  9 Amberwood Dr, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 4,257 Sq Ft
  • Built 2021

  9 Amberwood Dr, Winchester, MA 01890

  Last Sold Summary

  • 195 Days On Market

  Last Listing Agent Nicholas Gatto Better Homes and Gardens Real Estate - The Shanahan Group
• 

  

  /41

  $1,800,000

  Sold Feb 24, 2026

  61 Westland Ave, Winchester, MA 01890

  • 3 Beds
  • 3.5 Baths
  • 2,785 Sq Ft
  • Built 1952

  Last Sold Summary

  • 3% Above List Price
  • $646/SF
  • 6 Days On Market

  Current Estimated Value $1,711,175

  Last Listing Agent Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

  61 Westland Ave, Winchester, MA 01890
• 

  

  /42

  Est $2,434,116

  Not Listed For Sale

  5 Pilgrim Dr, Winchester, MA 01890

  • 6 Beds
  • 3.5 Baths
  • 4,138 Sq Ft
  • Built 1962

  5 Pilgrim Dr, Winchester, MA 01890

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
• 

  

  /35

  $2,325,000

  Sold Jun 18, 2026

  15 Gershon Way Unit 15, Winchester, MA 01890

  • 3 Beds
  • 3.5 Baths
  • 4,087 Sq Ft
  • Built 2020

  Last Sold Summary

  • 3% Below List Price
  • $569/SF
  • 13 Days On Market

  Current Estimated Value $2,266,443

  Last Listing Agent Moira Lown Coldwell Banker Realty - Wellesley

  15 Gershon Way Unit 15, Winchester, MA 01890
• 

  

  /42

  Est $1,846,914

  Not Listed For Sale

  19 Pilgrim Dr, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 3,150 Sq Ft
  • Built 1961

  19 Pilgrim Dr, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Gorfinkle Group eXp Realty LLC - Corporate Office
• 

  

  /27

  $1,775,000

  Sold Aug 21, 2026

  8 Hawthorne Rd, Winchester, MA 01890

  • 5 Beds
  • 4 Baths
  • 3,315 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $535/SF
  • 53 Days On Market

  Current Estimated Value $1,842,817

  Last Listing Agent Elaine Song Coldwell Banker Realty - Lexington

  8 Hawthorne Rd, Winchester, MA 01890

Showing Results 41 - 80, Page 2 of 18