West Side Homes

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  /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
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• 

  

  

  /42

  Est $1,770,082

  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
• 

  

  

  /42

  $1,099,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,711 Sq Ft

  150 Cambridge St, Winchester, MA 01890

  Charming colonial with lots of character! Step into a welcoming foyer that leads into an open concept kitchen and dining room area. Kitchen is fully equipped along with gas cooking and breakfast bar,front to back living room with a cozy fireplace surrounded by built-ins and slider out to a big sunny deck and crown moldings, french doors from living room lead out to a 4 season sun room perfect for

  Diane Plunkett Plunkett Properties

  150 Cambridge St, 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
• 

  

  

  /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
• 

  

  /32

  $1,299,000

  $31K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,145 Sq Ft

  7 Wainwright Rd Unit 47, Winchester, MA 01890

  Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub.

  Felicity Tuttle Better Homes and Gardens Real Estate - The Shanahan Group

  7 Wainwright Rd Unit 47, 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
• 

  

  /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
• 

  

  /42

  $1,699,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 2,513 Sq Ft

  2 Olde Lyme Rd, Winchester, MA 01890

  Beautifully updated & impeccably maintained 3 BR, 3.5 bath home on a sought-after cul-de-sac w/lovely front & side yards, abutting conservation land for exceptional privacy. The main level features a spacious living room, updated sunroom, granite kitchen w/newer SS appliances, abundant cabinetry, peninsula seating, & dining room w/ access to an inviting deck. Two 1st floor bedrooms & two full

  Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

  2 Olde Lyme Rd, 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
• 

  

  /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
• 

  

  /38

  $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
• 

  

  /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 $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
• 

  

  /36

  $3,600,000

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

  11 Viking Rd, Winchester, MA 01890

  Spectacular ground-up new construction estate on a quiet Winchester cul-de-sac near Wright Locke Farm. Newly completed, this exceptional residence spans more than 7,000 square feet across four impeccably finished levels. Ideally positioned on a quiet cul-de-sac in one of Winchester’s most desirable locations, the home offers an extraordinary combination of new construction, refined design,

  Valerie Post Engel & Volkers Boston

  11 Viking 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
• 

  

  /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 Gibson Sotheby's International Realty
• 

  

  /37

  $2,500,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

  $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 $2,434,116

  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
• 

  

  /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
• 

  

  /40

  Est $1,434,908

  Not Listed For Sale

  16 Johnson Rd, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 3,142 Sq Ft
  • Built 1958

  16 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Anne Spry Barrett Sotheby's International Realty
• 

  

  /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 $1,912,567

  Not Listed For Sale

  19 Johnson Rd, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 4,318 Sq Ft
  • Built 1956

  19 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Philip Vita Compass
• 

  

  /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
• 

  

  /39

  Est $2,007,321

  Not Listed For Sale

  1 Saint Augustine Ct, Winchester, MA 01890

  • 4 Beds
  • 4 Baths
  • 3,818 Sq Ft
  • Built 1967

  1 Saint Augustine Ct, Winchester, MA 01890

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
• 

  

  /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
• 

  

  /33

  Est $1,944,465

  Not Listed For Sale

  8 Olde Lyme Rd, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 4,603 Sq Ft
  • Built 1960

  8 Olde Lyme Rd, Winchester, MA 01890

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
• 

  

  /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 $2,171,477

  Last Listing Agent Moira Lown Coldwell Banker Realty - Wellesley

  15 Gershon Way Unit 15, Winchester, MA 01890
• 

  

  /25

  Est $1,846,007

  Not Listed For Sale

  4 Olde Lyme Rd, Winchester, MA 01890

  • 4 Beds
  • 4 Baths
  • 3,488 Sq Ft
  • Built 1980

  4 Olde Lyme Rd, Winchester, MA 01890

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
• 

  

  /42

  $1,987,000

  Sold Nov 18, 2025

  6 Samoset Rd, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 4,731 Sq Ft
  • Built 1992

  Last Sold Summary

  • 1% Below List Price
  • $420/SF
  • 16 Days On Market

  Current Estimated Value $2,147,644

  Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  6 Samoset Rd, Winchester, MA 01890
• 

  

  /26

  Est $1,173,020

  Not Listed For Sale

  75 Dunster Ln, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 1,826 Sq Ft
  • Built 1928

  75 Dunster Ln, Winchester, MA 01890

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Adriano Varano Keller Williams Realty
• 

  

  /19

  $1,820,000

  Sold Aug 19, 2025

  109 Thornberry Rd, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,784 Sq Ft
  • Built 1974

  Last Sold Summary

  • 1% Above List Price
  • $481/SF
  • 5 Days On Market

  Current Estimated Value $1,924,682

  Last Listing Agent Andrew Martini Compass

  109 Thornberry Rd, Winchester, MA 01890
• 

  

  /42

  Est $3,084,305

  Not Listed For Sale

  222 High St, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 5,676 Sq Ft
  • Built 2006

  222 High St, Winchester, MA 01890

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Gayle Winters Compass
• 

  

  /42

  $2,218,500

  Sold Aug 29, 2025

  17 Wagon Wheel Rd, Winchester, MA 01890

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

  Last Sold Summary

  • 6% Below List Price
  • $563/SF
  • 74 Days On Market

  Current Estimated Value $2,294,406

  Last Listing Agent Yifei Wang Dreamega International Realty LLC

  17 Wagon Wheel Rd, Winchester, MA 01890
• 

  

  /30

  Est $937,599

  Not Listed For Sale

  62 Edward Dr, Winchester, MA 01890

  • 2 Beds
  • 2.5 Baths
  • 1,857 Sq Ft
  • Built 1985

  62 Edward Dr, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Melissa Perrone Better Homes and Gardens Real Estate - The Shanahan Group

Showing Results 41 - 80, Page 2 of 18