West Side Homes

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  /33

  Est $2,057,891 Not Listed For Sale

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

  8 Olde Lyme Rd, Winchester, MA 01890

  8 Olde Lyme Rd, Winchester, MA 01890
• 

  

  

  /37

  $1,450,000 Sold May 30, 2025

  • 3,763 Sq Ft
  • $385/SF
  • 34 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1988

  7 Wainwright Rd Unit 8, Winchester, MA 01890

  Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large

  Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

  7 Wainwright Rd Unit 8, Winchester, MA 01890
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  /42

  Est $1,794,196 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,315 Sq Ft

  8 Hawthorne Rd, Winchester, MA 01890

  8 Hawthorne Rd, Winchester, MA 01890
• 

  

  

  /25

  $1,881,900 Sold May 30, 2025

  • 3,488 Sq Ft
  • $540/SF
  • 34 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1980

  4 Olde Lyme Rd, Winchester, MA 01890

  This stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulted ceilings, a floor-to-ceiling fireplace and an open-concept design, this spacious home is bathed in natural beauty. The gourmet kitchen is pristine and boasts high-end appliances, quartz countertops, a prep sink and secondary dishwasher, and a large island—ideal for

  Nancy Pallotta Gibson Sotheby's International Realty

  4 Olde Lyme Rd, Winchester, MA 01890
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  /42

  Est $2,537,083 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,473 Sq Ft

  239 Ridge St, Winchester, MA 01890

  239 Ridge St, Winchester, MA 01890
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  /33

  $1,785,000 Sold May 22, 2025

  • 2,848 Sq Ft
  • $627/SF
  • 13 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1968

  85 Thornberry Rd, Winchester, MA 01890

  Welcome to the highly-coveted Westside of Winchester, MA. This meticulously maintained Colonial-style home is set on 20,000 sqft lot with professional landscaping. The living room features a charming wood-burning fireplace, while the sun-filled formal dining room is centered with an elegant chandelier. The kitchen has granite countertops, stainless steel appliances, and an adjacent eat-in area

  Diane Basemera Coldwell Banker Realty - Newton

  85 Thornberry Rd, Winchester, MA 01890
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  /26

  Est $1,152,913 Not Listed For Sale

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

  75 Dunster Ln, Winchester, MA 01890

  75 Dunster Ln, Winchester, MA 01890
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  /42

  $4,065,000 Sold May 16, 2025

  • 7,500 Sq Ft
  • $542/SF
  • 71 Days On Market

  • 6 Beds
  • 7.5 Baths
  • Built 2025

  6 Vinson Cir, Winchester, MA 01890

  Nestled on a cul-de-sac in Winchester's desirable west side, this brand-new construction redefines modern luxury living. Spanning 7,500 sq. ft., this exquisite 6-bedroom, 7.5-bathroom home combines style, comfort, and functionality. Discover an open-concept floor plan bathed in natural light, perfect for entertaining and everyday living. The kitchen features top-of-the-line Wolf appliances,

  Peter Kasseris Compass

  6 Vinson Cir, Winchester, MA 01890
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  /42

  Est $3,292,108 Not Listed For Sale

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

  222 High St, Winchester, MA 01890

  222 High St, Winchester, MA 01890
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  /15

  $1,088,000 Sold May 08, 2025

  • 2,172 Sq Ft
  • $501/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1985

  322 Cambridge St, Winchester, MA 01890

  Not your average Garrison Colonial! You might not expect the bright, open charm waiting within this inviting 8-room, 3-level home. The stunning main level living room, dining and kitchen area boasts cathedral ceilings, skylights, and a dramatic brick fireplace, creating a sense of space and light. This home features 2 full baths and 4 bedrooms, including 3 with brand-new hardwood floors and a

  Joanne McDonnell RE/MAX Real Estate Center

  322 Cambridge St, Winchester, MA 01890
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  /27

  Est $1,094,077 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,859 Sq Ft

  46 Edward Dr, Winchester, MA 01890

  46 Edward Dr, Winchester, MA 01890
• 

  

  /42

  $1,890,000 Sold Mar 28, 2025

  • 4,318 Sq Ft
  • $438/SF
  • 7 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1956

  19 Johnson Rd, Winchester, MA 01890

  A DESIGNER DREAM! Welcome to 19 Johnson Road, a pristine 5-bedroom colonial-style home located in the highly sought-after Vinson Owen School district! As you enter the home, you are greeted by a stunning curved staircase adorned with molding and a statement-making light fixture. The first level boasts a fireplaced living room, a fireplaced family room, an updated kitchen, and a gorgeous formal

  Philip Vita Compass

  19 Johnson Rd, Winchester, MA 01890
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  /36

  Est $1,033,168 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,568 Sq Ft

  55 Edward Dr, Winchester, MA 01890

  55 Edward Dr, Winchester, MA 01890
• 

  

  /31

  $940,000 Sold Mar 14, 2025

  • 2,418 Sq Ft
  • $389/SF
  • 8 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  60 Edward Dr Unit 60, Winchester, MA 01890

  Welcome to this move in ready townhouse in Pepper Hill Estates! Enjoy easy living with this stunning open concept home boasting a newer eat-in kitchen, spacious dining room & oversized living room with a wood burning fireplace and floor to ceiling windows that are flooded w/natural light. This main floor also has great closet space, a half bath and a beautiful rear deck to enjoy. The 2nd level

  Kim Covino Compass

  60 Edward Dr Unit 60, Winchester, MA 01890
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  /42

  Est $1,050,725 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,738 Sq Ft

  41 Edward Dr, Winchester, MA 01890

  41 Edward Dr, Winchester, MA 01890
• 

  

  /27

  $1,200,000 Sold Feb 28, 2025

  • 3,350 Sq Ft
  • $358/SF
  • 183 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1989

  7 Wainwright Rd Unit 22, Winchester, MA 01890

  Now is the time to make a move! Step into a sophisticated lifestyle as you enter through a charming courtyard into this elegant condo. The beautifully updated kitchen is a standout, featuring granite countertops, cherry cabinetry, and premium new stainless steel appliances—a chef’s dream come true. The open-concept layout is perfect for modern living, with a dining area flowing into the inviting

  DeWolfe Group Gibson Sotheby's International Realty

  7 Wainwright Rd Unit 22, Winchester, MA 01890
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  /38

  Est $1,078,186 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,754 Sq Ft

  34 Edward Dr, Winchester, MA 01890

  34 Edward Dr, Winchester, MA 01890
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  /42

  $2,025,000 Sold Feb 21, 2025

  • 4,997 Sq Ft
  • $405/SF
  • 8 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1975

  23 Olde Village Dr, Winchester, MA 01890

  Welcome to this exceptional one floor living ranch-style home, a true haven for both luxury living and car enthusiasts. Nestled among towering trees, this expansive property offers the perfect balance of privacy and beauty, with a stunning 4-car garage designed to accommodate your prized vehicles, ample storage space, workshop, home gym or additional living space. With a grand, welcoming entrance

  Andersen Group Realty Keller Williams Realty Boston Northwest

  23 Olde Village Dr, Winchester, MA 01890
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  /37

  Est $881,400 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft

  47 Edward Dr, Winchester, MA 01890

  47 Edward Dr, Winchester, MA 01890
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  /38

  $1,650,000 Sold Jan 30, 2025

  • 2,376 Sq Ft
  • $694/SF
  • 30 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1927

  36 Oneida Rd, Winchester, MA 01890

  TOTAL RENOVATION! Thoughtfully crafted to create a warm and inviting abode. Step inside to discover the completely reimagined first floor with an open concept dining room, sitting room, and show-stopping brand new kitchen with a center island, and a slider leading to a patio, ideal for alfresco dining and entertaining. The first floor also hosts a versatile family room with access to a private

  Philip Vita Compass

  36 Oneida Rd, Winchester, MA 01890
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  /31

  Est $1,875,566 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,028 Sq Ft

  56 Ridge St, Winchester, MA 01890

  56 Ridge St, Winchester, MA 01890
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  /38

  $1,900,000 Sold Jan 29, 2025

  • 3,611 Sq Ft
  • $526/SF
  • 50 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1984

  11 Plymouth Rd, Winchester, MA 01890

  OPEN HOUSE SUNDAY 11/17 11:30-1:00pm. Magnificent Brick Colonial, perfectly situated at the end of a quite dead-end street, abutting conservation that offers unmatched privacy and tranquility. The gorgeous, spacious foyer leads into the beautiful front to back living room with a warm and inviting fireplace. The well-appointed dining room with custom built-in China cabinet is perfect for large

  Darryl Brian RE/MAX Bentley's

  11 Plymouth Rd, Winchester, MA 01890
• 

  

  /23

  Est $1,017,694 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,548 Sq Ft

  12 James St, Winchester, MA 01890

  12 James St, Winchester, MA 01890
• 

  

  /42

  $1,517,500 Sold Jan 09, 2025

  • 3,091 Sq Ft
  • $491/SF
  • 7 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1957

  14 Henry St, Winchester, MA 01890

  Incredible value! Don’t miss this 6 BR, 3 full bathroom expanded colonial w/ over 3,000 square feet of living space tucked away in a charming Vinson Owen School neighborhood. This expansive home features an open concept, eat-in kitchen/family room w/ granite countertops, double ovens, large island, recessed lighting & cozy family room. The sunny kitchen also opens to a private backyard w/ stone

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

  14 Henry St, Winchester, MA 01890
• 

  

  /38

  Est $1,250,372 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,827 Sq Ft

  10 James St, Winchester, MA 01890

  10 James St, Winchester, MA 01890
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  /29

  $1,335,000 Sold Dec 27, 2024

  • 2,245 Sq Ft
  • $595/SF
  • 117 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  28 Thornberry Rd, Winchester, MA 01890

  Welcome to 28 Thornberry! Located in the highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the home sits high above the road, you can enjoy complete privacy in your open-concept living, dining,

  Shaundize Moosavizadeh Coldwell Banker Realty - Boston

  28 Thornberry Rd, Winchester, MA 01890
• 

  

  /42

  Est $944,501 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,890 Sq Ft

  25 Henry St, Winchester, MA 01890

  25 Henry St, Winchester, MA 01890
• 

  

  /38

  $1,650,000 Sold Dec 11, 2024

  • 3,158 Sq Ft
  • $522/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  31 Girard Rd, Winchester, MA 01890

  Welcome to 31 Girard Road, a lovely colonial gracefully positioned on a prominent corner lot in the Vinson Owen School district! As you step inside, you’ll pass an exquisite curved staircase on your way to the front-to-back living room with custom built-ins. The heart of the home is the open kitchen, seamlessly connected to a bright and airy dining area. This space is perfect for hosting

  Philip Vita Compass

  31 Girard Rd, Winchester, MA 01890
• 

  

  /26

  Est $838,577 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,279 Sq Ft

  28 Henry St, Winchester, MA 01890

  28 Henry St, Winchester, MA 01890
• 

  

  /30

  $900,000 Sold Nov 21, 2024

  • 1,857 Sq Ft
  • $485/SF
  • 6 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  62 Edward Dr, Winchester, MA 01890

  Welcome to 62 Edward Drive in the sought-after Pepper Hill Estates. This spacious townhouse-style condo features two bedrooms and a versatile bonus room on the lower level, perfect for a home office, guest space, or playroom. The well-maintained home boasts an open living and dining area filled with natural light and a beautiful fireplace. The updated kitchen includes granite countertops, newer

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

  62 Edward Dr, Winchester, MA 01890
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  /20

  Est $1,064,140 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  14 Locke St, Winchester, MA 01890

  14 Locke St, Winchester, MA 01890
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  /42

  $2,035,000 Sold Nov 19, 2024

  • 4,730 Sq Ft
  • $430/SF
  • 12 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1953

  43 Emerson Rd, Winchester, MA 01890

  See it to believe it! Don’t miss this sprawling 5 bed, 4 full bath Cape-style home in an idyllic Ambrose school neighborhood. 1st floor features mudroom w/entry from attached garage, laundry room w/sink, living room w/fireplace, bedroom, full bath, & dining area w/French doors to a deck. But the jewel of this floor is the recent addition of a stunning eat-in kitchen & sun-filled primary suite.

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

  43 Emerson Rd, Winchester, MA 01890
• 

  

  /17

  Est $2,163,979 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,578 Sq Ft

  21 Dunster Ln, Winchester, MA 01890

  21 Dunster Ln, Winchester, MA 01890
• 

  /2

  $1,910,000 Sold Nov 04, 2024

  • 5,287 Sq Ft
  • $361/SF
  • 9 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1977

  5 Thoreau Cir, Winchester, MA 01890

  Welcome to this custom-built oversized ranch, cherished & meticulously maintained by the current owners. This idyllic property is situated on a large lot at the end of a cul-de-sac, abutting peaceful conservation land. The main level features grand scale rooms including a spacious eat in kitchen, 2 beautiful living rooms w/ wood burning fireplaces, a stunning dining room for holidays & dinner

  Kim Covino Compass

  5 Thoreau Cir, Winchester, MA 01890
• 

  

  /38

  Est $1,238,423 Not Listed For Sale

  • 5 Beds
  • 1.5 Baths
  • 2,383 Sq Ft

  18 Ridge St, Winchester, MA 01890

  18 Ridge St, Winchester, MA 01890
• 

  /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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  /40

  Est $2,557,739 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 6,259 Sq Ft

  280 High St, Winchester, MA 01890

  280 High St, Winchester, MA 01890
• 

  

  /41

  Est $2,120,665 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,730 Sq Ft

  2 Tanglewood Ln, Winchester, MA 01890

  2 Tanglewood Ln, Winchester, MA 01890
• 

  

  /40

  Est $2,228,283 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
• 

  

  /42

  Est $1,263,153 Not Listed For Sale

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

  119 Ridge St, Winchester, MA 01890

  119 Ridge St, Winchester, MA 01890

Showing Results 81 - 120, Page 3 of 18