West Side Homes

• 

  

  

  /33

  $2,849,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 5,058 Sq Ft

  7 Viking Rd, Winchester, MA 01890

  Tucked on a quiet cul-de-sac in the sought-after Vinson Owen school district, this completely renovated 5-bedroom, 4.5-bath Colonial offers an exceptional blend of comfort and elevated design. Massive columns in classic revival style create stunning curb appeal, offering a striking introduction to the transformation inside. A spectacular chef's kitchen anchors the main level, featuring an

  Andersen Group Realty Keller Williams Realty Boston Northwest

  7 Viking Rd, Winchester, MA 01890
• Explore West Side

• 

  

  

  /20

  Starting at $2,568

  Total Monthly Price

  • Studio - 3 Beds

  416 Cambridge St, Winchester, MA 01890

  The Sanctuary at Winchester West is crafted to elevate every moment of your day—from morning workouts in the fully equipped fitness center to productive afternoons in private work-from-home pods and inviting gathering spaces. Whether you're entertaining in the chef-inspired kitchen and lounge, relaxing by the fire with neighbors, or enjoying the convenience of Whole Foods and local shops just

  Sanctuary Winchester West

  

  416 Cambridge St, Winchester, MA 01890
• 

  

  

  /42

  $1,055,000

  Sold May 15, 2026

  15 Edward Dr Unit 15, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Above List Price
  • $507/SF
  • 5 Days On Market

  Last Listing Agent Alina Wang Coldwell Banker Realty - Lexington

  15 Edward Dr Unit 15, Winchester, MA 01890
• 

  

  

  /42

  Est $1,696,280

  Not Listed For Sale

  9 Pilgrim Dr, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,541 Sq Ft
  • Built 1960

  9 Pilgrim Dr, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate
• 

  

  

  /42

  $1,925,000

  $75K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  15 Fieldstone Dr, Winchester, MA 01890

  Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless

  Anne Spry Barrett Sotheby's International Realty

  15 Fieldstone Dr, Winchester, MA 01890
• 

  

  /11

  $2,293 Plus Fees

  • 1 Bed
  • 1 Bath
  • 651 Sq Ft
  • Condo for Rent

  3 Wainwright Rd Unit 203, Winchester, MA 01890

  With common spaces designed with you in mind, The Sanctuary at Winchester West invites you to live an inspired life. Gather around the fireplace in the Great Room, create a culinary masterpiece in the Chef’s Kitchen, or reflect and recharge in one of many curated outdoor living spaces. At The Sanctuary, there’s space for all your pursuits. Each apartment home at The Sanctuary at Winchester West

  3 Wainwright Rd Unit 203, Winchester, MA 01890
• 

  

  /31

  $1,240,000

  Sold Apr 27, 2026

  12 Thornberry Rd, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 2,087 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Above List Price
  • $594/SF
  • 6 Days On Market

  Current Estimated Value $1,238,250

  Last Listing Agent Kim Covino Compass

  12 Thornberry Rd, Winchester, MA 01890
• 

  

  /42

  Est $3,598,589

  Not Listed For Sale

  6 Vinson Cir, Winchester, MA 01890

  • 6 Beds
  • 7.5 Baths
  • 7,500 Sq Ft
  • Built 2025

  6 Vinson Cir, Winchester, MA 01890

  Last Sold Summary

  • 71 Days On Market

  Last Listing Agent Peter Kasseris Serhant
• 

  

  /37

  $1,499,000

  $100K PRICE DROP Pending

  • 4 Beds
  • 4 Baths
  • 2,480 Sq Ft

  241 Ridge St, Winchester, MA 01890

  New roof and fresh exterior paint just completed! This move-in-ready 4-bedroom, 2 full bath, 2 half bath home has been thoughtfully updated and meticulously maintained, offering the perfect blend of timeless charm, modern updates, and exceptional outdoor living in one of Winchester's most sought-after neighborhoods. Recent improvements include a brand-new roof, freshly painted exterior, all-new

  Team Lillian Montalto Lillian Montalto Signature Properties

  241 Ridge St, Winchester, MA 01890
• 

  

  /11

  $2,293 Plus Fees

  • 1 Bed
  • 1 Bath
  • 767 Sq Ft
  • Condo for Rent

  3 Wainwright Rd Unit 212, Winchester, MA 01890

  With common spaces designed with you in mind, The Sanctuary at Winchester West invites you to live an inspired life. Gather around the fireplace in the Great Room, create a culinary masterpiece in the Chef’s Kitchen, or reflect and recharge in one of many curated outdoor living spaces. At The Sanctuary, there’s space for all your pursuits. Each apartment home at The Sanctuary at Winchester West

  3 Wainwright Rd Unit 212, Winchester, MA 01890
• 

  

  /42

  $1,055,000

  Sold Feb 26, 2026

  7 Trinity Rd, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 1963

  Last Sold Summary

  • 11% Below List Price
  • $495/SF
  • 24 Days On Market

  Current Estimated Value $1,191,098

  Last Listing Agent Gayle Winters Compass

  7 Trinity Rd, Winchester, MA 01890
• 

  

  /42

  Est $2,903,722

  Not Listed For Sale

  228 Ridge St, Winchester, MA 01890

  • 5 Beds
  • 5.5 Baths
  • 6,265 Sq Ft
  • Built 2023

  228 Ridge St, Winchester, MA 01890

  Last Sold Summary

  • 142 Days On Market

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

  

  /4

  $3,200,000

  • 5 Beds
  • 5.5 Baths
  • 5,295 Sq Ft

  18 Ridge St, Winchester, MA 01890

  Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort.

  Gayle Winters Compass

  18 Ridge St, Winchester, MA 01890
• 

  

  /11

  $2,769 Plus Fees

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft
  • Condo for Rent

  3 Wainwright Rd Unit 525, Winchester, MA 01890

  With common spaces designed with you in mind, The Sanctuary at Winchester West invites you to live an inspired life. Gather around the fireplace in the Great Room, create a culinary masterpiece in the Chef’s Kitchen, or reflect and recharge in one of many curated outdoor living spaces. At The Sanctuary, there’s space for all your pursuits. Each apartment home at The Sanctuary at Winchester West

  3 Wainwright Rd Unit 525, Winchester, MA 01890
• 

  

  /42

  $1,580,000

  Sold Feb 26, 2026

  10 Trinity Rd, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • Built 1963

  Last Sold Summary

  • 11% Above List Price
  • $748/SF
  • 5 Days On Market

  Current Estimated Value $1,543,175

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  10 Trinity Rd, Winchester, MA 01890
• 

  

  /40

  Est $1,357,776

  Not Listed For Sale

  15 Wincrest Dr, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,529 Sq Ft
  • Built 1957

  15 Wincrest Dr, Winchester, MA 01890

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Kim Covino Compass
• 

  

  /42

  $3,200,000

  Open Sat 12:30PM - 2PM $200K PRICE DROP

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

  9 Albamont Rd, Winchester, MA 01890

  Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept

  Kim Covino Compass

  9 Albamont Rd, Winchester, MA 01890
• 

  

  /38

  $6,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,443 Sq Ft
  • House for Rent

  25 Berkshire Dr, Winchester, MA 01890

  This beautifully renovated home offers over 2,400 sq ft of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today's lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high end Spanish panels, dovetail

  Nadia Mounsif McCaul & Mounsif Real Estate Group LLC

  25 Berkshire Dr, Winchester, MA 01890
• 

  

  /40

  $1,715,000

  Sold Sep 03, 2026

  94 Johnson Rd, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 3,366 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $510/SF
  • 34 Days On Market

  Current Estimated Value $1,782,114

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

  94 Johnson Rd, Winchester, MA 01890
• 

  

  /33

  Est $1,459,872

  Not Listed For Sale

  10 Carriage Ln, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 2,034 Sq Ft
  • Built 1957

  10 Carriage Ln, Winchester, MA 01890

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Peter Kasseris Serhant
• 

  

  /30

  $2,799,000

  $51K PRICE DROP Pending

  • 6 Beds
  • 7 Baths
  • 6,968 Sq Ft

  14 Nassau Dr, Winchester, MA 01890

  Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

  Weidong Li WINN Real Estate & Consulting

  14 Nassau Dr, Winchester, MA 01890
• 

  

  /28

  $3,100 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  7 Ridge St, Winchester, MA 01890

  Welcome to this charming 2-bedroom, 1.5-bath rental located on the desirable west side of Winchester. Offering three levels of living space, this home provides plenty of room to spread out and enjoy a comfortable, flexible layout. Beautiful hardwood floors add warmth and character throughout, while the level, partially fenced backyard provides a wonderful private outdoor space for relaxing,

  Shannon Jenkins RE/MAX Realty Experts

  7 Ridge St, Winchester, MA 01890
• 

  

  /41

  $1,360,000

  Sold Jul 29, 2026

  15 Thornberry Rd, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 4,062 Sq Ft
  • Built 1957

  Last Sold Summary

  • 1% Above List Price
  • $335/SF
  • 7 Days On Market

  Current Estimated Value $1,365,421

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

  15 Thornberry Rd, Winchester, MA 01890
• 

  

  /39

  Est $1,377,940

  Not Listed For Sale

  9 Thornberry Rd, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft
  • Built 1957

  9 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Louise Coakley Better Homes and Gardens Real Estate - The Shanahan Group
• 

  

  /42

  $3,450,000

  Open Sat 12:30PM - 2PM

  • 6 Beds
  • 4.5 Baths
  • 5,735 Sq Ft

  7 Hutchinson Rd, Winchester, MA 01890

  Situated on a generous18,000SF level lot! Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the

  Kim Covino Compass

  7 Hutchinson Rd, Winchester, MA 01890
• 

  

  /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 $2,039,319

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

  64 Westland Ave, Winchester, MA 01890
• 

  

  /29

  Est $1,335,559

  Not Listed For Sale

  28 Thornberry Rd, Winchester, MA 01890

  • 4 Beds
  • 2 Baths
  • 2,245 Sq Ft
  • Built 1959

  28 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 117 Days On Market

  Last Listing Agent Shaundize Moosavizadeh Coldwell Banker Realty - Boston
• 

  

  /42

  $3,149,000

  • 7 Beds
  • 7.5 Baths
  • 8,540 Sq Ft

  37 Mayflower Rd, Winchester, MA 01890

  Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by

  Kim Covino Compass

  37 Mayflower Rd, Winchester, MA 01890
• 

  

  /40

  $3,150,000

  Sold May 28, 2026

  257 High St, Winchester, MA 01890

  • 5 Beds
  • 7 Baths
  • 7,101 Sq Ft
  • Built 1994

  Last Sold Summary

  • 3% Below List Price
  • $444/SF
  • 2 Days On Market

  Current Estimated Value $3,118,023

  Last Listing Agent Kim Covino Compass

  257 High St, Winchester, MA 01890
• 

  

  /37

  Est $1,504,318

  Not Listed For Sale

  65 Thornberry Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,525 Sq Ft
  • Built 1965

  65 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Jun Zhang HMW Real Estate, LLC
• 

  

  /42

  $2,100,000

  Open Sat 11AM - 12PM

  • 4 Beds
  • 3.5 Baths
  • 3,640 Sq Ft

  7 Wainwright Rd Unit 113, Winchester, MA 01890

  Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home

  Kim Covino Compass

  7 Wainwright Rd Unit 113, Winchester, MA 01890
• 

  

  /33

  $1,936,000

  Sold Jun 23, 2026

  2 Gershon Way Unit 2, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,306 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Above List Price
  • $840/SF
  • 7 Days On Market

  Current Estimated Value $1,906,419

  Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  2 Gershon Way Unit 2, Winchester, MA 01890
• 

  

  /19

  Est $1,924,682

  Not Listed For Sale

  109 Thornberry Rd, Winchester, MA 01890

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

  109 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Andrew Martini Compass
• 

  

  /42

  $1,050,000

  $49K PRICE DROP 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
• 

  

  /42

  $1,700,000

  Sold Jun 29, 2026

  29 Pilgrim Dr, Winchester, MA 01890

  • 5 Beds
  • 3 Baths
  • 3,271 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $520/SF
  • 20 Days On Market

  Current Estimated Value $1,737,516

  Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  29 Pilgrim Dr, Winchester, MA 01890
• 

  

  /35

  Est $1,705,406

  Not Listed For Sale

  22 Berkshire Dr, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 3,224 Sq Ft
  • Built 1967

  22 Berkshire Dr, Winchester, MA 01890

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Timothy Morgan RE/MAX Innovative Properties
• 

  

  /37

  $1,295,000

  Open Fri 4PM - 6PM

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

  7 Wainwright Rd Unit 47, Winchester, MA 01890

  This Ledges "A" Style townhouse condo offers extensive single floor living with a spacious first floor primary suite as well as a separate second floor suite and loft area. The main bedroom is truly vast. The first floor den can be used as a third bedroom. The home is move-in ready with all new oak hardwood floors throughout the finished areas! Entirely freshly painted in Moore's attractive

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

  7 Wainwright Rd Unit 47, Winchester, MA 01890
• 

  

  /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

  Current Estimated Value $1,856,310

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

  7 Wainwright Rd Unit 13, Winchester, MA 01890
• 

  

  /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
• 

  

  /25

  $2,249,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 4,368 Sq Ft

  11 Locke St, Winchester, MA 01890

  Built in 2021, this stunning home is ready for its next owners to enjoy. Its elevated setting provides a peaceful retreat with multiple areas for outdoor living, including a charming front porch. Inside, thoughtful design and exceptional attention to detail are evident throughout. The expansive open-concept kitchen, living and dining areas offer an ideal setting for entertaining, complemented by

  Lesley Smith Barrett Sotheby's International Realty

  11 Locke St, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18