Winchester, MA Homes

• 

  

  

  /42

  $2,100,000

  • 6 Beds
  • 2.5 Baths
  • 4,104 Sq Ft

  15 Wildwood St, Winchester, MA 01890

  Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for thoughtful updates to further enhance its value. Step inside to a sun-filled living room w/oversized

  Kim Covino Compass

  15 Wildwood St, Winchester, MA 01890
• 

  

  

  /38

  $5,400 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,659 Sq Ft
  • House for Rent

  330 Cambridge St, Winchester, MA 01890

  Well-maintained updated two-level single-family rental offering a bright, open feel and a flexible layout. The home features 4 bedrooms and two full baths, with generous living space across both levels.The main level includes spacious living and dining areas filled with natural light from large windows. An open kitchen offers space for a dining table and a functional, livable layout that opens to

  Leigh Ventura Compass

  330 Cambridge St, Winchester, MA 01890
• 

  

  

  /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 $1,551,835

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

  5 Thornton Rd, Winchester, MA 01890
• 

  

  

  /42

  Est $1,802,353 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

  • 10% Below List Price
  • $595/SF
  • 6 Days On Market

  Last Sold Price $2,000,000

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

  

  

  /42

  $2,199,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,798 Sq Ft

  61 Grove St, Winchester, MA 01890

  Experience the perfect blend of luxury and effortless living in this stunning custom-built residence, thoughtfully rebuilt and expanded to offer a sophisticated, maintenance-free lifestyle. Bathed in natural light, the flexible floor plan begins with a magnificent first-floor primary suite featuring a marble-clad bath, soaking tub, and walk-in shower. The heart of the home is a chef’s kitchen

  Dorothea Feffer Churchill Properties

  61 Grove St, Winchester, MA 01890
• 

  

  /24

  $3,300 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,486 Sq Ft
  • Apartment for Rent

  7 Conant Rd Unit 67, Winchester, MA 01890

  Condo community with use of wonderful exercise facility, outdoor heated pool and community center. In-unit laundry, no lead paint, Central AC. Beautiful 2 bed 2.5 bath townhouse with a 2 car parking at the sought-after Willows in Winchester. Elevator building to second floor then the unit is a spacious townhouse 2nd and 3rd floors. No one above you. Open floor plan from kitchen to living room

  Dave Ledwig Coldwell Banker Realty - Lexington

  7 Conant Rd Unit 67, Winchester, MA 01890
• 

  

  /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 $1,527,107

  Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

  21 Johnson Rd, Winchester, MA 01890
• 

  

  /39

  Est $1,777,508 Not Listed For Sale

  7 Wainwright Rd Unit 37, Winchester, MA 01890

  • 2 Beds
  • 4 Baths
  • 3,655 Sq Ft
  • Built 1988

  7 Wainwright Rd Unit 37, Winchester, MA 01890

  Last Sold Summary

  • 13% Above List Price
  • $431/SF
  • 6 Days On Market

  Last Sold Price $1,575,000

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

  

  /42

  $958,000 Open Sat 11:30AM - 1:30PM

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

  15 Edward Dr Unit 15, Winchester, MA 01890

  Welcome to the highly sought-after Pepper Hill Estates, ideally situated on a quiet street near Vinson-Owen Elementary School and within walking distance to Wright-Locke Farm and McClennen Park. This Colonial-style home offers a highly desirable and functional layout. The first floor features an open-concept design with a spacious living room, dining area, and a custom-built kitchen by Schrock

  Alina Wang Coldwell Banker Realty - Lexington

  15 Edward Dr Unit 15, Winchester, MA 01890
• 

  

  /29

  $5,350 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,575 Sq Ft
  • Condo for Rent

  2 Rangeley Rd Unit 2, Winchester, MA 01890

  Location, Location, Location!! This beautifully updated 2 bedroom 2.5 bath conveniently located in Winchester Center. Recently renovated, this unit boasts a stunning kitchen with farmer sink, high end stainless appliances, custom cabinetry and pantry. First floor offers living room w/ fireplace and large dining room with hardwood throughout. 2 spacious bedrooms and 1.5 baths complete the second

  Kim Covino Compass

  2 Rangeley Rd Unit 2, Winchester, MA 01890
• 

  

  /42

  $1,558,000 Sold May 29, 2025

  24 Eugene Dr, Winchester, MA 01890

  • 3 Beds
  • 3.5 Baths
  • 2,792 Sq Ft
  • Built 1993

  Last Sold Summary

  • 18% Above List Price
  • $558/SF
  • 9 Days On Market

  Current Estimated Value $1,497,012

  Last Listing Agent Andrea O'Reilly Keller Williams Realty Evolution

  24 Eugene Dr, Winchester, MA 01890
• 

  

  /42

  Est $1,879,865 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% Above List Price
  • $449/SF
  • 7 Days On Market

  Last Sold Price $1,750,000

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
• 

  

  /31

  $1,200,000 Pending

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

  12 Thornberry Rd, Winchester, MA 01890

  Lovingly maintained and tastefully renovated, this spacious three bedroom, two bath ranch with 3 car garage will impress! This remodeled open concept home is set on an oversized 16k lot and features a beautiful kitchen with custom cabinetry & dining island ideal for both every day living and entertaining. The main level also offers an inviting living room with bay window & fireplace, dining room

  Kim Covino Compass

  12 Thornberry Rd, Winchester, MA 01890
• 

  

  /42

  $1,850,000 Sold Jan 15, 2026

  77A Brooks St, Winchester, MA 01890

  • 6 Beds
  • 3.5 Baths
  • 4,122 Sq Ft
  • Built 1890

  Last Sold Summary

  • 19% Below List Price
  • $449/SF
  • 35 Days On Market

  Current Estimated Value $1,927,034

  Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  77A Brooks St, Winchester, MA 01890
• 

  

  /41

  Est $1,652,298 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

  • 10% Above List Price
  • $270/SF
  • 7 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Jill Citrano Leading Edge Real Estate
• 

  

  /39

  $1,560,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,578 Sq Ft

  17 Cranston Rd, Winchester, MA 01890

  Expanded Cape blends timeless charm with thoughtful updates, offering inviting living spaces designed for comfort and connection. A fireplaced living room with hardwood floors and French doors sets a warm tone, flowing into an elegant dining area accented by custom built-ins and refined detailing. The kitchen serves as the heart of the home, featuring stone countertops, stainless appliances, and

  Anne Spry Barrett Sotheby's International Realty

  17 Cranston Rd, 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 $1,923,907

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

  7 Wainwright Rd Unit 13, Winchester, MA 01890
• 

  

  /42

  Est $1,938,290 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

  • 1% Above List Price
  • $669/SF
  • 7 Days On Market

  Last Sold Price $1,910,000

  Last Listing Agent Kim Covino Compass
• 

  

  /18

  $452,500 Pending

  • 3 Beds
  • 1 Bath
  • 1,573 Sq Ft

  22 Oak St, Winchester, MA 01890

  Welcome to Winchester! Ideally located within walking distance of WHS and Winchester Center, this home offers exceptional value in one of the area’s most desirable communities. The main level features a newly renovated kitchen with adjacent living and dining areas, creating a functional and inviting open layout ideal for everyday living and entertaining. The second floor includes three bedrooms

  Rameel Rana Advise Realty

  22 Oak St, Winchester, MA 01890
• 

  

  /40

  $1,160,000 Sold Aug 14, 2025

  518 Washington St, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,302 Sq Ft
  • Built 1915

  Last Sold Summary

  • 3% Below List Price
  • $504/SF
  • 22 Days On Market

  Current Estimated Value $1,206,162

  Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

  518 Washington St, Winchester, MA 01890
• 

  

  /42

  Est $2,802,208 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

  • 6% Above List Price
  • $467/SF
  • 12 Days On Market

  Last Sold Price $2,650,000

  Last Listing Agent Lucille Murray Gibson Sotheby's International Realty
• 

  

  /42

  $1,749,000 Open Fri 5PM - 6:30PM

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

  29 Pilgrim Dr, Winchester, MA 01890

  Beautifully updated home offers generous living spaces and a seamless, open flow. Sun-filled living and dining areas feature hardwood floors, elegant detailing, and a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, and large island that opens to the dining area, which flows into the

  Anne Spry Barrett Sotheby's International Realty

  29 Pilgrim Dr, Winchester, MA 01890
• 

  

  /41

  $2,425,000 Sold Jul 31, 2025

  15 Churchill Rd, Winchester, MA 01890

  • 4 Beds
  • 4.5 Baths
  • 5,501 Sq Ft
  • Built 2025

  Last Sold Summary

  • 7% Below List Price
  • $441/SF
  • 61 Days On Market

  Current Estimated Value $2,373,037

  Last Listing Agent Kim Covino Compass

  15 Churchill Rd, Winchester, MA 01890
• 

  

  /42

  Est $2,727,009 Not Listed For Sale

  40 Amberwood Dr, Winchester, MA 01890

  • 6 Beds
  • 3.5 Baths
  • 5,713 Sq Ft
  • Built 1983

  40 Amberwood Dr, Winchester, MA 01890

  Last Sold Summary

  • 19% Above List Price
  • $403/SF
  • 8 Days On Market

  Last Sold Price $2,300,000

  Last Listing Agent Kim Covino Compass
• 

  

  /42

  $1,795,000 Pending

  • 3 Beds
  • 3 Baths
  • 3,182 Sq Ft

  114 Johnson Rd, Winchester, MA 01890

  Welcome Home to this gracious Colonial set on beautifully manicured grounds in one of Winchester’s most sought-after neighborhoods, known for its vibrant community & top-rated schools. An oversized updated kitchen w/ Corian countertops, double ovens & abundant cabinetry anchors the home, opening to an elegant dining room & inviting formal living room. Lovely hardwood floors thruout add warmth &

  Rosemary Kelleher LAER Realty Partners

  114 Johnson Rd, Winchester, MA 01890
• 

  

  /42

  $2,499,000 Sold May 19, 2025

  50 Winford Way, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 4,270 Sq Ft
  • Built 2024

  Last Sold Summary

  • $585/SF
  • 0 Days On Market

  Current Estimated Value $2,388,889

  Last Listing Agent Kim Covino Compass

  50 Winford Way, Winchester, MA 01890
• 

  

  /38

  Est $1,833,017 Not Listed For Sale

  45 Amberwood Dr, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 4,008 Sq Ft
  • Built 1983

  45 Amberwood Dr, Winchester, MA 01890

  Last Sold Summary

  • 18% Above List Price
  • $387/SF
  • 3 Days On Market

  Last Sold Price $1,550,000

  Last Listing Agent Kim Covino Compass
• 

  

  /39

  $3,425,000 Open Sat 1PM - 2:30PM

  • 7 Beds
  • 7.5 Baths
  • 7,226 Sq Ft

  15 Mayflower Rd, Winchester, MA 01890

  Discover a stunningly reimagined home nestled in one of Winchester’s most sought after neighborhoods—an exceptional opportunity to own a beautifully crafted, completely transformed residence. Expanded and rebuilt with intention, 15 Mayflower delivers the space, layout, and flexibility today’s lifestyle demands, with a thoughtful floor plan that balances open concept living and well defined

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  15 Mayflower Rd, Winchester, MA 01890
• 

  

  /13

  $680,000 Sold May 15, 2025

  15 Charles Rd, Winchester, MA 01890

  • 2 Beds
  • 2 Baths
  • 968 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Above List Price
  • $702/SF
  • 12 Days On Market

  Current Estimated Value $649,283

  Last Listing Agent Beiping Zhao Jack Gately Real Estate, LLC

  15 Charles Rd, Winchester, MA 01890
• 

  

  /36

  Est $2,320,508 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

  • 21% Above List Price
  • $451/SF
  • 195 Days On Market

  Last Sold Price $1,920,000

  Last Listing Agent Nicholas Gatto Better Homes and Gardens Real Estate - The Shanahan Group
• 

  

  /42

  $3,750,000 Pending

  • 6 Beds
  • 3.5 Baths
  • 4,484 Sq Ft

  9 Lakeview Terrace, Winchester, MA 01890

  LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room!

  Kim Covino Compass

  9 Lakeview Terrace, Winchester, MA 01890
• 

  

  /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 $1,982,501

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  31 Coolidge Rd, Winchester, MA 01890
• 

  

  /42

  Est $2,181,042 Not Listed For Sale

  9 Buckman Dr, Winchester, MA 01890

  • 6 Beds
  • 3.5 Baths
  • 4,124 Sq Ft
  • Built 1970

  9 Buckman Dr, Winchester, MA 01890

  Last Sold Summary

  • 15% Above List Price
  • $461/SF
  • 4 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Philip Vita Compass
• 

  

  /42

  $1,249,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,454 Sq Ft

  40 Pickering St, Winchester, MA 01890

  This charming home retains period details while delivering flexible modern living. Through the glass-enclosed front porch, the first floor offers an entry stair hall, formal living room, a bedroom or home office with full bath and separate entrance, kid's homework room/drop zone, and - the star of the show - a sun-drenched open plan kitchen/family room with fireplace, massive island, and plenty

  Timothy Haynes Keller Williams Realty Signature Properties

  40 Pickering St, Winchester, MA 01890
• 

  

  /23

  $950,000 Sold Dec 04, 2025

  16 Park Ave Unit 1, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft
  • Built 1915

  Last Sold Summary

  • 5% Below List Price
  • $619/SF
  • 26 Days On Market

  Current Estimated Value $953,457

  Last Listing Agent Andrea Mackey The Agency Boston

  16 Park Ave Unit 1, Winchester, MA 01890
• 

  

  /42

  Est $2,339,906 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

  • 3% Below List Price
  • $580/SF
  • 5 Days On Market

  Last Sold Price $2,400,000

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
• 

  

  /22

  $649,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,317 Sq Ft

  20 Charles Rd, Winchester, MA 01890

  Rarely available 3 bedroom 2 full bathrooms Townhouse at The Residences at Winchester, located in the most coveted and brand new Lynch School district. Updated kitchen with stainless steel appliances, spacious and sun-filled living room with large picture window, gleaming hardwood floor throughout. Upstairs features 3 bright bedrooms and an updated full bath. Finished lower level boasts a laundry

  Wei Wenny Wenny Fu Phoenix Real Estate

  20 Charles Rd, Winchester, MA 01890
• 

  

  /39

  $4,650,000 Sold May 01, 2025

  19 Rangeley Rd, Winchester, MA 01890

  • 5 Beds
  • 7 Baths
  • 7,779 Sq Ft
  • Built 1915

  Last Sold Summary

  • 3% Below List Price
  • $598/SF
  • 5 Days On Market

  Current Estimated Value $4,348,275

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  19 Rangeley Rd, Winchester, MA 01890
• 

  

  /42

  Est $1,963,699 Not Listed For Sale

  15 Pilgrim Dr, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 4,256 Sq Ft
  • Built 1959

  15 Pilgrim Dr, Winchester, MA 01890

  Last Sold Summary

  • 5% Above List Price
  • $441/SF
  • 13 Days On Market

  Last Sold Price $1,875,000

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
• 

  

  /35

  $1,000,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,749 Sq Ft

  320 Washington St, Winchester, MA 01890

  Classic Victorian charm in a convenient Winchester location close to shops, the commuter rail, library, Farmers’ Market, and the Middlesex Fells. An inviting entry opens to a bright living room with a built-in window seat offering hidden storage. The main level flows into the dining room with an attached office alcove and half bath, providing flexible work-from-home space. The renovated eat-in

  John Conroy East Coast Realty, Inc.

  320 Washington St, Winchester, MA 01890

Showing Results 81 - 120, Page 3 of 18