West Side Homes

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  /40

  Est $2,207,897 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,567 Sq Ft

  99 Ridge St, Winchester, MA 01890

  99 Ridge St, Winchester, MA 01890
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  /2

  $1,675,000 Sold Jul 11, 2025

  • 4,228 Sq Ft
  • $396/SF
  • 8 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1987

  7 Wainwright Rd Unit 55, Winchester, MA 01890

  Welcome to The Ledges—an exceptional custom-designed “E” style end-unit townhouse offering over 10 rooms of refined living space and a distinctive layout found in no other unit. Thoughtfully maintained and tastefully updated, this residence features an expansive open floor plan with cathedral ceilings, elegant crown molding, and a gourmet chef’s kitchen equipped with premium appliances. The first

  Ngoc Anh Goldstein Leading Edge Real Estate

  7 Wainwright Rd Unit 55, Winchester, MA 01890
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  /42

  Est $1,171,015 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,542 Sq Ft

  119 Ridge St, Winchester, MA 01890

  119 Ridge St, Winchester, MA 01890
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  /2

  $1,200,000 Sold Nov 01, 2024

  • 2,122 Sq Ft
  • $566/SF
  • 0 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1959

  15 Mayflower Rd, Winchester, MA 01890

  Welcome to 15 Mayflower Road! This property includes 4 bedrooms and 2.5 bathrooms, providing a comfortable living space. The layout features common areas suitable for everyday living and gatherings. The home is in need of some work and updates to fully realize its potential. The neighborhood is welcoming and a good place to establish a home. Consider this property if you're looking for a

  Monte Marrocco Coldwell Banker Realty - Lexington

  15 Mayflower Rd, Winchester, MA 01890
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  /40

  Est $1,388,780 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  25 Lockeland Rd, Winchester, MA 01890

  25 Lockeland Rd, Winchester, MA 01890
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  /37

  Est $2,203,287 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,209 Sq Ft

  4 Mayflower Rd, Winchester, MA 01890

  4 Mayflower Rd, Winchester, MA 01890
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  /40

  Est $1,812,928 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,744 Sq Ft

  20 Mayflower Rd, Winchester, MA 01890

  20 Mayflower Rd, Winchester, MA 01890
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  /42

  Est $2,119,944 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,770 Sq Ft

  7 Plymouth Rd, Winchester, MA 01890

  7 Plymouth Rd, Winchester, MA 01890
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  /36

  Est $1,640,967 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 4,190 Sq Ft

  43 Mayflower Rd, Winchester, MA 01890

  43 Mayflower Rd, Winchester, MA 01890
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  /35

  Est $2,068,512 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,439 Sq Ft

  34 Mayflower Rd, Winchester, MA 01890

  34 Mayflower Rd, Winchester, MA 01890
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  /42

  Est $3,199,550 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 4,805 Sq Ft

  53 Hutchinson Rd, Winchester, MA 01890

  53 Hutchinson Rd, Winchester, MA 01890
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  /33

  Est $1,312,595 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,636 Sq Ft

  132 Cambridge St, Winchester, MA 01890

  132 Cambridge St, Winchester, MA 01890
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  /42

  Est $2,321,933 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 7,292 Sq Ft

  7 Russett Ln, Winchester, MA 01890

  7 Russett Ln, Winchester, MA 01890
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  /42

  Est $2,190,589 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 5,800 Sq Ft

  8 Johnson Rd, Winchester, MA 01890

  8 Johnson Rd, Winchester, MA 01890
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  /40

  Est $2,851,306 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,051 Sq Ft

  50 Emerson Rd, Winchester, MA 01890

  50 Emerson Rd, Winchester, MA 01890
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  /37

  Est $1,897,988 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,689 Sq Ft

  36 Robinhood Rd, Winchester, MA 01890

  36 Robinhood Rd, Winchester, MA 01890
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  /33

  Est $1,533,004 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,920 Sq Ft

  10 Albamont Rd, Winchester, MA 01890

  10 Albamont Rd, Winchester, MA 01890
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  /27

  Est $1,376,734 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,413 Sq Ft

  12 Albamont Rd, Winchester, MA 01890

  12 Albamont Rd, Winchester, MA 01890
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  /37

  Est $1,417,102 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,597 Sq Ft

  22 Albamont Rd, Winchester, MA 01890

  22 Albamont Rd, Winchester, MA 01890
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  /31

  Est $1,155,740 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,321 Sq Ft

  23 New Meadows Rd, Winchester, MA 01890

  23 New Meadows Rd, Winchester, MA 01890
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  /37

  Est $1,383,355 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,386 Sq Ft

  15 New Meadows Rd, Winchester, MA 01890

  15 New Meadows Rd, Winchester, MA 01890
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  /25

  Est $1,575,697 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,139 Sq Ft

  11 New Meadows Rd, Winchester, MA 01890

  11 New Meadows Rd, Winchester, MA 01890
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  /36

  Est $1,850,070 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,432 Sq Ft

  21 Westland Ave, Winchester, MA 01890

  21 Westland Ave, Winchester, MA 01890
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  /40

  Est $1,760,203 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,414 Sq Ft

  23 Westland Ave, Winchester, MA 01890

  23 Westland Ave, Winchester, MA 01890
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  /41

  Est $2,799,707 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,100 Sq Ft

  14 Seneca Rd, Winchester, MA 01890

  14 Seneca Rd, Winchester, MA 01890
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  /42

  Est $2,768,709 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,315 Sq Ft

  6 Agawam Rd, Winchester, MA 01890

  6 Agawam Rd, Winchester, MA 01890
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  /39

  Est $1,628,685 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,428 Sq Ft

  21 Samoset Rd, Winchester, MA 01890

  21 Samoset Rd, Winchester, MA 01890
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  /28

  Est $1,761,756 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,800 Sq Ft

  5 Manomet Rd, Winchester, MA 01890

  5 Manomet Rd, Winchester, MA 01890
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  /36

  Est $2,514,501 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,871 Sq Ft

  111 Arlington St, Winchester, MA 01890

  111 Arlington St, Winchester, MA 01890
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  /41

  Est $2,951,381 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,830 Sq Ft

  108 Arlington St, Winchester, MA 01890

  108 Arlington St, Winchester, MA 01890
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  /42

  Est $2,225,026 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  20 Westland Ave, Winchester, MA 01890

  20 Westland Ave, Winchester, MA 01890
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  /40

  Est $1,571,380 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,071 Sq Ft

  10 Westland Ave, Winchester, MA 01890

  10 Westland Ave, Winchester, MA 01890
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  /36

  Est $1,813,989 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,189 Sq Ft

  152 Hutchinson Rd, Arlington, MA 02474

  152 Hutchinson Rd, Arlington, MA 02474
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  /41

  Est $1,598,274 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft

  78 Dunster Ln, Winchester, MA 01890

  78 Dunster Ln, Winchester, MA 01890
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  /42

  Est $4,096,650 Not Listed For Sale

  • 6 Beds
  • 6.5 Baths
  • 8,000 Sq Ft

  12 Saint Thomas More Dr, Winchester, MA 01890

  12 Saint Thomas More Dr, Winchester, MA 01890
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  /35

  Est $2,368,678 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,138 Sq Ft

  29 Gershon Way Unit 29, Winchester, MA 01890

  29 Gershon Way Unit 29, Winchester, MA 01890
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  /38

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,638 Sq Ft

  26 Gershon Way Unit 26, Winchester, MA 01890

  26 Gershon Way Unit 26, Winchester, MA 01890
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  /30

  Est $1,064,337 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,679 Sq Ft

  29 Edward Dr Unit 29, Winchester, MA 01890

  29 Edward Dr Unit 29, Winchester, MA 01890
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  /38

  Est $2,036,299 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,638 Sq Ft

  27 Gershon Way Unit 27, Winchester, MA 01890

  27 Gershon Way Unit 27, Winchester, MA 01890
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  /41

  Est $2,131,472 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,938 Sq Ft

  19 Gershon Way Unit 19, Winchester, MA 01890

  19 Gershon Way Unit 19, Winchester, MA 01890

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