West Side Homes

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  /36

  $3,600,000 Open Sun 1PM - 2PM

  • 6 Beds
  • 7 Baths
  • 8,866 Sq Ft

  20 Amberwood Dr, Winchester, MA 01890

  Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

  

  Wei Wang

  WW Real Estate LLC

  (781) 678-8050

  20 Amberwood Dr, Winchester, MA 01890
• Explore West Side

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  /20

  $2,729 - $21,078 per month plus fees

  Sanctuary Winchester West

  Studio - 3 Beds

  416 Cambridge St, Winchester, MA 01890

  The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

  416 Cambridge St, Winchester, MA 01890
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  /39

  $2,200,000 Sold Jun 30, 2025

  1 Saint Augustine Ct, Winchester, MA 01890

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

  Last Sold Summary

  • 10% Above List Price
  • $576/SF
  • 0 Days On Market

  Current Estimated Value $2,137,315

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  1 Saint Augustine Ct, Winchester, MA 01890
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  /42

  Est $1,502,190 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,091 Sq Ft

  14 Henry St, Winchester, MA 01890

  14 Henry St, Winchester, MA 01890
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  /41

  $1,750,000 Pending

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

  61 Westland Ave, Winchester, MA 01890

  This beautiful, move-in-ready Cape has been thoughtfully renovated from top to bottom. Oversized front walks lead to a charming front porch and into a welcoming foyer that opens to a sun-filled open-concept layout with fire-placed family room, dining area, and kitchen—ideal for everyday living and entertaining. A bright bonus room off the kitchen with wall-to-wall windows and heat/AC offers

  

  Catherine Albiani

  Better Homes and Gardens Real Estate - The Shanahan Group

  (781) 613-3908

  61 Westland Ave, Winchester, MA 01890
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  /19

  $4,200 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,548 Sq Ft
  • House for Rent

  12 James St, Winchester, MA 01890

  Move into a well-maintained 3-bedroom, 1.5-bathroom single-family home in quiet Winchester neighborhood. The house featuring central AC, in-home laundry, and garage parking. The finished lower level provides extra living space. Enjoy your own lovely, private backyard. You're within walking distance to McClennen Park, Wright-Locke Farm, and the scenic Whipple Hill conservation area—boasting 120

  Gigi Nguyen Harmony Hill Realty LLC

  12 James St, Winchester, MA 01890
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  /25

  $1,881,900 Sold May 30, 2025

  4 Olde Lyme Rd, Winchester, MA 01890

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

  Last Sold Summary

  • 1% Below List Price
  • $540/SF
  • 34 Days On Market

  Current Estimated Value $1,864,593

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  4 Olde Lyme Rd, Winchester, MA 01890
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  /42

  Est $2,856,133 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,265 Sq Ft

  228 Ridge St, Winchester, MA 01890

  228 Ridge St, Winchester, MA 01890
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  /42

  $2,299,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,953 Sq Ft

  19 Gershon Way Unit 1, Winchester, MA 01890

  Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

  Philip Vita Compass

  19 Gershon Way Unit 1, Winchester, MA 01890
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  /42

  $8,500 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 4,656 Sq Ft
  • House for Rent

  23 Olde Village Dr, Winchester, MA 01890

  OH January 10 11-12PM! This exceptional ranch-style home offers the ease of one-floor living with a private, serene feel while remaining close to everyday conveniences. Pets are welcome, making this a rare and flexible rental opportunity. The home features a gracious entry leading into a spacious, light-filled family room with soaring skylights, an open layout ideal for living and entertaining,

  Ngoc Anh Goldstein Leading Edge Real Estate

  23 Olde Village Dr, Winchester, MA 01890
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  /37

  $1,390,000 Sold Jul 15, 2025

  26 Ridge St, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft
  • Built 1963

  Last Sold Summary

  • 1% Above List Price
  • $582/SF
  • 6 Days On Market

  Current Estimated Value $1,387,320

  Last Listing Agent Dream Team Dreamega International Realty LLC

  26 Ridge St, Winchester, MA 01890
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  /40

  Est $1,368,150 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,529 Sq Ft

  15 Wincrest Dr, Winchester, MA 01890

  15 Wincrest Dr, Winchester, MA 01890
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  /42

  $2,299,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,953 Sq Ft

  19 Gershon Way, Winchester, MA 01890

  Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

  Philip Vita Compass

  19 Gershon Way, Winchester, MA 01890
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  /29

  $7,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 3,218 Sq Ft
  • House for Rent

  29 Wainwright Rd, Winchester, MA 01890

  No Broker Fee! Beautifully updated 4-bedroom single-family home in a top Winchester neighborhood. Over 3,200 sq ft of space with multiple living areas, a flexible layout, and a private yard—ideal for families, professionals, or anyone needing room to spread out. The main level offers an open kitchen with stainless appliances and granite counters, dining area, and two bright living spaces with

  Helen Stefan Gibson Sotheby's International Realty

  29 Wainwright Rd, Winchester, MA 01890
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  /39

  $2,050,000 Sold Oct 15, 2025

  64 Westland Ave, Winchester, MA 01890

  • 4 Beds
  • 5 Baths
  • 3,716 Sq Ft
  • Built 1931

  Last Sold Summary

  • $552/SF
  • 2 Days On Market

  Current Estimated Value $2,016,103

  Last Listing Agent The Murphy Group Lexington William Raveis R.E. & Home Services

  64 Westland Ave, Winchester, MA 01890
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  /33

  Est $1,479,735 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,034 Sq Ft

  10 Carriage Ln, Winchester, MA 01890

  10 Carriage Ln, Winchester, MA 01890
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  /42

  $2,595,000

  • 4 Beds
  • 4 Baths
  • 5,674 Sq Ft

  10 Viking Rd, Winchester, MA 01890

  Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

  Anne Spry Barrett Sotheby's International Realty

  10 Viking Rd, Winchester, MA 01890
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  /38

  $1,525,000 Sold Sep 12, 2025

  5 Thornton Rd, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 2,755 Sq Ft
  • Built 1929

  Last Sold Summary

  • 12% Below List Price
  • $554/SF
  • 30 Days On Market

  Current Estimated Value $1,558,830

  Last Listing Agent Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

  5 Thornton Rd, Winchester, MA 01890
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  /29

  Est $1,356,466 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,245 Sq Ft

  28 Thornberry Rd, Winchester, MA 01890

  28 Thornberry Rd, Winchester, MA 01890
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  /42

  $1,125,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  7 Trinity Rd, Winchester, MA 01890

  Welcome to 7 Trinity Road, a warm & inviting split level home tucked away on a quiet side street in sought after Winchester. From the moment you step inside, the home feels welcoming & comfortable, offering 3 bed & 2.5 baths with a layout that easily supports both everyday living & entertaining. Your foyer provides a convenient place to arrive home, with direct access to the attached garage. The

  Gayle Winters Compass

  7 Trinity Rd, Winchester, MA 01890
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  /42

  $1,540,000 Sold Jul 11, 2025

  21 Johnson Rd, Winchester, MA 01890

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

  Last Sold Summary

  • 1% Above List Price
  • $547/SF
  • 5 Days On Market

  Current Estimated Value $1,534,981

  Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

  21 Johnson Rd, Winchester, MA 01890
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  /35

  Est $1,677,936 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,926 Sq Ft

  16 Nassau Dr, Winchester, MA 01890

  16 Nassau Dr, Winchester, MA 01890
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  /42

  $1,149,000 Pending

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

  16 Ridge St, Winchester, MA 01890

  27,000 SF lot!!! Set far back from the street~ Don't miss this opportunity! Whether looking to lightly update/ expand or completely renovate; this well maintained 3 bedroom split entry home with a stunning oversized private yard offers tremendous potential! The first floor is spacious with large sunny rooms incl. a generously sized living room with picture window & wood burning fireplace, a

  Kim Covino Compass

  16 Ridge St, Winchester, MA 01890
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  /24

  $2,155,000 Sold Oct 21, 2025

  7 Wainwright Rd Unit 13, Winchester, MA 01890

  • 3 Beds
  • 4.5 Baths
  • 3,186 Sq Ft
  • Built 1988

  Last Sold Summary

  • $676/SF
  • 1 Day On Market

  Last Listing Agent Isabella Bruno William Raveis R.E. & Home Services

  7 Wainwright Rd Unit 13, Winchester, MA 01890
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  /36

  Est $1,570,816 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,171 Sq Ft

  94 Johnson Rd, Winchester, MA 01890

  94 Johnson Rd, Winchester, MA 01890
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  /33

  $1,499,000 Pending

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

  7 Wainwright Rd Unit 118, Winchester, MA 01890

  Exceptional 3 Bedroom 3 1/2 Bath Highly Desired End Unit Townhome at The Ledges! Main Level Features include: Inviting Sun-Filled Entry Foyer, Gleaming Hardwood Floors, Cathedral Ceilings, Granite/Stainless Chef's Kitchen w/Breakfast Room, Formal Dining Room, Living Room w/Gas Fireplace and Private Deck overlooking Tranquil Wooded Setting. Family Study w/ Custom Built-ins, Luxurious Primary

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Wainwright Rd Unit 118, Winchester, MA 01890
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  /27

  $1,200,000 Sold Feb 28, 2025

  7 Wainwright Rd Unit 22, Winchester, MA 01890

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

  Last Sold Summary

  • 30% Below List Price
  • $358/SF
  • 183 Days On Market

  Current Estimated Value $1,238,938

  Last Listing Agent DeWolfe Group Gibson Sotheby's International Realty

  7 Wainwright Rd Unit 22, Winchester, MA 01890
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  /32

  Est $1,615,482 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  104 Thornberry Rd, Winchester, MA 01890

  104 Thornberry Rd, Winchester, MA 01890
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  /40

  $1,499,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,351 Sq Ft

  19 Cox Rd, Winchester, MA 01890

  Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen with newer appliances leads to the open concept dining room overlooking the beautiful, private yard. The spacious living room features a fplc & bay window; a sunroom, 3 spacious bedrooms, 1 bath & garage complete the main level; the lower level offers a large rec/ family room w

  Kim Covino Compass

  19 Cox Rd, Winchester, MA 01890
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  /41

  $2,000,000 Sold Apr 15, 2025

  31 Coolidge Rd, Winchester, MA 01890

  • 4 Beds
  • 4 Baths
  • 4,650 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Below List Price
  • $430/SF
  • 11 Days On Market

  Current Estimated Value $1,990,584

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  31 Coolidge Rd, Winchester, MA 01890
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  /39

  Est $1,846,390 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,046 Sq Ft

  73 Thornberry Rd, Winchester, MA 01890

  73 Thornberry Rd, Winchester, MA 01890
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  /41

  $1,460,000

  • 3 Beds
  • 2.5 Baths
  • 2,316 Sq Ft

  26 Berkshire Dr, Winchester, MA 01890

  Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is

  DANIEL BEIRNE OpenDoor Brokerage LLC

  26 Berkshire Dr, Winchester, MA 01890
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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

  Last Listing Agent Debby Valdes eXp Realty

  205 Ridge St, Winchester, MA 01890
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  /35

  Est $1,736,643 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,224 Sq Ft

  22 Berkshire Dr, Winchester, MA 01890

  22 Berkshire Dr, Winchester, MA 01890
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  /24

  $969,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  139 High St, Winchester, MA 01890

  This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to

  Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

  139 High St, Winchester, MA 01890
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  /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 $1,773,844

  Last Listing Agent Hudson Santana Keller Williams Realty Boston Northwest

  44 Amberwood Dr, Winchester, MA 01890
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  /42

  Est $2,191,931 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,620 Sq Ft

  5 Partridge Ln, Winchester, MA 01890

  5 Partridge Ln, Winchester, MA 01890
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  /41

  $2,299,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,773 Sq Ft

  8 Buckman Dr, Winchester, MA 01890

  Move-in ready home on Winchester’s highly desirable West Side, set on a quiet street with a bright, inviting layout. The first floor offers a sun-filled primary suite, a kitchen with granite countertops and adjacent flexible space ideal for casual dining or family room use, plus a formal dining room, living room, and half bath. Upstairs features a second primary suite, a guest en-suite, two

  Andersen Group Realty Keller Williams Realty Boston Northwest

  8 Buckman Dr, Winchester, MA 01890
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  /2

  $1,675,000 Sold Jul 11, 2025

  7 Wainwright Rd Unit 55, Winchester, MA 01890

  • 3 Beds
  • 3.5 Baths
  • 4,228 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Above List Price
  • $396/SF
  • 8 Days On Market

  Current Estimated Value $1,689,972

  Last Listing Agent Ngoc Anh Goldstein Leading Edge Real Estate

  7 Wainwright Rd Unit 55, Winchester, MA 01890
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  /40

  Est $2,089,055 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 4,532 Sq Ft

  89 Thornberry Rd, Winchester, MA 01890

  89 Thornberry Rd, Winchester, MA 01890

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