Winchester, MA Homes

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  /32

  $868,000

  Sold Sep 04, 2025

  235 Cross St, Winchester, MA 01890

  • 3 Beds
  • 1.5 Baths
  • 1,931 Sq Ft
  • Built 1956

  Last Sold Summary

  • 16% Above List Price
  • $450/SF
  • 8 Days On Market

  Current Estimated Value $941,026

  Last Listing Agent Melanie Lentini Leading Edge Real Estate

  235 Cross St, Winchester, MA 01890
• 

  

  

  /42

  Est $1,498,166

  Not Listed For Sale

  14 Henry St, Winchester, MA 01890

  • 6 Beds
  • 3 Baths
  • 3,091 Sq Ft
  • Built 1957

  14 Henry St, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

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

  

  

  /30

  $950,000

  • 3 Beds
  • 1 Bath
  • 1,356 Sq Ft

  47 Water St, Winchester, MA 01890

  Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds

  The Mary Scimemi Team Leading Edge Real Estate

  47 Water St, Winchester, MA 01890
• 

  

  

  /39

  $1,425,000

  Sold Dec 01, 2025

  102 Hillcrest Pkwy, Winchester, MA 01890

  • 4 Beds
  • 2 Baths
  • 1,755 Sq Ft
  • Built 1939

  Last Sold Summary

  • 19% Above List Price
  • $812/SF
  • 4 Days On Market

  Current Estimated Value $1,462,947

  Last Listing Agent Curtis Howe Howe Realty Group

  102 Hillcrest Pkwy, Winchester, MA 01890
• 

  

  

  /20

  Est $1,069,180

  Not Listed For Sale

  14 Locke St, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft
  • Built 1910

  14 Locke St, Winchester, MA 01890

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Ruth Gagne Barrett Sotheby's International Realty
• 

  

  /27

  $1,825,000

  $100K PRICE DROP Pending

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

  8 Hawthorne Rd, Winchester, MA 01890

  Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees.

  Elaine Song Coldwell Banker Realty - Lexington

  8 Hawthorne Rd, Winchester, MA 01890
• 

  

  /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

  Current Estimated Value $1,619,078

  Last Listing Agent Debby Valdes eXp Realty LLC

  205 Ridge St, Winchester, MA 01890
• 

  

  /37

  Est $1,413,403

  Not Listed For Sale

  26 Ridge St, Winchester, MA 01890

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

  26 Ridge St, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Dream Team Dreamega International Realty LLC
• 

  

  /42

  $2,100,000

  • 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
• 

  

  /36

  $519,000

  Sold Oct 08, 2025

  115 Washington St Unit 3D, Winchester, MA 01890

  • 1 Bed
  • 1.5 Baths
  • 769 Sq Ft
  • Built 1988

  Last Sold Summary

  • $675/SF
  • 5 Days On Market

  Current Estimated Value $522,173

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

  115 Washington St Unit 3D, Winchester, MA 01890
• 

  

  /40

  Est $2,363,468

  Not Listed For Sale

  280 High St, Winchester, MA 01890

  • 6 Beds
  • 5 Baths
  • 6,259 Sq Ft
  • Built 1976

  280 High St, Winchester, MA 01890

  Last Sold Summary

  • 136 Days On Market

  Last Listing Agent Anthony Marino The Marino Group Collection
• 

  

  /32

  $1,125,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,736 Sq Ft

  38 Robinhood Rd, Winchester, MA 01890

  Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open

  Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

  38 Robinhood Rd, Winchester, MA 01890
• 

  

  /35

  $1,375,000

  Sold Jan 23, 2026

  32 Oak St, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,652 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Above List Price
  • $518/SF
  • 6 Days On Market

  Current Estimated Value $1,367,838

  Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

  32 Oak St, Winchester, MA 01890
• 

  

  /33

  Est $1,714,714

  Not Listed For Sale

  34 Coolidge Rd, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,338 Sq Ft
  • Built 1980

  34 Coolidge Rd, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Pauline Marino Coldwell Banker Realty - Lexington
• 

  

  /42

  $1,099,000

  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
• 

  

  /22

  $2,400,000

  Sold Dec 18, 2025

  19 Laurel Hill Ln, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 3,700 Sq Ft
  • Built 1954

  Last Sold Summary

  • 4% Below List Price
  • $649/SF
  • 3 Days On Market

  Current Estimated Value $1,959,855

  Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty

  19 Laurel Hill Ln, Winchester, MA 01890
• 

  

  /41

  Est $1,932,103

  Not Listed For Sale

  31 Coolidge Rd, Winchester, MA 01890

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

  31 Coolidge Rd, Winchester, MA 01890

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
• 

  

  /36

  $2,000,000

  Pending

  • 6 Beds
  • 5 Baths
  • 3,403 Sq Ft

  6 Ivy Cir, Winchester, MA 01890

  Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves

  Valerie Post Engel & Volkers Boston

  6 Ivy Cir, Winchester, MA 01890
• 

  

  /42

  $2,450,000

  Sold Dec 16, 2025

  30 Prospect St, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,519 Sq Ft
  • Built 1934

  Last Sold Summary

  • 17% Above List Price
  • $973/SF
  • 3 Days On Market

  Current Estimated Value $2,245,337

  Last Listing Agent Karima Alami Compass

  30 Prospect St, Winchester, MA 01890
• 

  

  /42

  Est $2,090,287

  Not Listed For Sale

  23 Olde Village Dr, Winchester, MA 01890

  • 3 Beds
  • 3.5 Baths
  • 4,997 Sq Ft
  • Built 1975

  23 Olde Village Dr, Winchester, MA 01890

  Last Sold Summary

  • 8 Days On Market

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

  

  /24

  $849,000

  • 3 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  15 Clark St Unit 15, Winchester, MA 01890

  Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated

  Jeffrey Hsu Coldwell Banker Realty - Milton

  15 Clark St Unit 15, Winchester, MA 01890
• 

  

  /4

  $700,000

  Sold Apr 28, 2026

  20 Charles Rd, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 1,317 Sq Ft
  • Built 1962

  Last Sold Summary

  • 8% Above List Price
  • $532/SF
  • 8 Days On Market

  Current Estimated Value $692,080

  Last Listing Agent Wei Wenny Fu Phoenix Real Estate

  20 Charles Rd, Winchester, MA 01890
• 

  

  /38

  Est $1,730,966

  Not Listed For Sale

  31 Girard Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 3,158 Sq Ft
  • Built 1975

  31 Girard Rd, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Philip Vita Compass
• 

  

  /32

  $1,299,000

  $31K PRICE DROP

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

  7 Wainwright Rd Unit 47, Winchester, MA 01890

  Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub.

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

  7 Wainwright Rd Unit 47, Winchester, MA 01890
• 

  

  /39

  $1,310,000

  Sold Jun 30, 2026

  12 Hancock St, Winchester, MA 01890

  • 3 Beds
  • 1.5 Baths
  • 2,030 Sq Ft
  • Built 1907

  Last Sold Summary

  • 1% Above List Price
  • $645/SF
  • 6 Days On Market

  Current Estimated Value $1,293,171

  Last Listing Agent Elena Langlois Compass

  12 Hancock St, Winchester, MA 01890
• 

  

  /40

  Est $2,174,236

  Not Listed For Sale

  99 Ridge St, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 4,567 Sq Ft
  • Built 2004

  99 Ridge St, Winchester, MA 01890

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Doug Hills Compass
• 

  

  /39

  $1,498,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,387 Sq Ft

  14 Rangeley Ridge, Winchester, MA 01890

  Located in the highly desirable Rangeley Estates - a location that puts everyday conveniences close with comfortable living. The main level is designed for everyday living & entertaining with a spacious fireplaced living room with built-in bookcase, separate family room with large closets, dining room opens to deck for easy indoor/outdoor entertaining, kitchen with island seating & stainless

  Peter Rooney Compass

  14 Rangeley Ridge, Winchester, MA 01890
• 

  

  /40

  $1,100,000

  Sold Sep 12, 2025

  5 Cutting St, Winchester, MA 01890

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $778/SF
  • 8 Days On Market

  Current Estimated Value $1,120,960

  Last Listing Agent Oliver Koester Compass

  5 Cutting St, Winchester, MA 01890
• 

  

  /42

  Est $1,248,155

  Not Listed For Sale

  119 Ridge St, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 2,542 Sq Ft
  • Built 1956

  119 Ridge St, Winchester, MA 01890

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Charles Jolin Keller Williams Realty
• 

  

  /42

  $2,499,000

  $100K PRICE DROP Pending Pre-Foreclosure

  • 5 Beds
  • 3.5 Baths
  • 5,230 Sq Ft

  78 Bacon St, Winchester, MA 01890

  Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR,

  Kim Covino Compass

  78 Bacon St, Winchester, MA 01890
• 

  

  /37

  $665,000

  Sold Nov 14, 2025

  7 Conant Rd Unit 20, Winchester, MA 01890

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Built 2000

  Last Sold Summary

  • 8% Below List Price
  • $569/SF
  • 124 Days On Market

  Current Estimated Value $689,650

  Last Listing Agent Brian Woods Woods Properties Inc.

  7 Conant Rd Unit 20, Winchester, MA 01890
• 

  

  /42

  Est $1,733,152

  Not Listed For Sale

  50 Johnson Rd, Winchester, MA 01890

  • 3 Beds
  • 4 Baths
  • 2,646 Sq Ft
  • Built 1957

  50 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 18 Days On Market

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

  

  /42

  $1,794,000

  $5K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,010 Sq Ft

  1 Town Way, Winchester, MA 01890

  Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing

  Philip Vita Compass

  1 Town Way, Winchester, MA 01890
• 

  

  /42

  $4,450,000

  Sold Oct 24, 2025

  20 Foxcroft Rd, Winchester, MA 01890

  • 5 Beds
  • 7 Baths
  • 7,679 Sq Ft
  • Built 1937

  Last Sold Summary

  • 1% Above List Price
  • $580/SF
  • 1 Day On Market

  Current Estimated Value $4,611,547

  Last Listing Agent Carolyn Walsh Better Homes and Gardens Real Estate - The Shanahan Group

  20 Foxcroft Rd, Winchester, MA 01890
• 

  

  /40

  Est $1,427,756

  Not Listed For Sale

  25 Lockeland Rd, Winchester, MA 01890

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft
  • Built 1954

  25 Lockeland Rd, Winchester, MA 01890

  Last Sold Summary

  • 12 Days On Market

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

  

  /39

  $3,799,000

  Pending

  • 6 Beds
  • 7.5 Baths
  • 6,000 Sq Ft

  29 Ginn Rd, Winchester, MA 01890

  Exceptional new construction offering approximately 6,000 sq ft of thoughtfully designed living space with 6 bedrooms, 7.5 baths, and a 3-car garage. A striking exterior showcases natural stonework, copper roof accents, copper gutters, and a welcoming covered porch. Inside, custom millwork, wide-plank hardwood floors, soaring ceilings, a floating staircase, and designer finishes create a timeless

  Peter Kasseris Serhant

  29 Ginn Rd, Winchester, MA 01890
• 

  /2

  $2,025,000

  Sold Jul 09, 2026

  36 Cambridge St, Winchester, MA 01890

  • 5 Beds
  • 5 Baths
  • 3,956 Sq Ft
  • Built 2026

  Last Sold Summary

  • 1% Above List Price
  • $512/SF
  • 5 Days On Market

  Current Estimated Value $1,178,362

  Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  36 Cambridge St, Winchester, MA 01890
• 

  

  /42

  Est $2,302,733

  Not Listed For Sale

  7 Plymouth Rd, Winchester, MA 01890

  • 4 Beds
  • 4 Baths
  • 2,770 Sq Ft
  • Built 1959

  7 Plymouth Rd, Winchester, MA 01890

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
• 

  

  /42

  $1,150,000

  $75K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  53 Lake St, Winchester, MA 01890

  Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming

  Kim Covino Compass

  53 Lake St, Winchester, MA 01890
• 

  

  /36

  $1,945,000

  Sold Sep 16, 2025

  20 Grayson Rd, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 3,825 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Above List Price
  • $508/SF
  • 7 Days On Market

  Current Estimated Value $1,916,269

  Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  20 Grayson Rd, Winchester, MA 01890

Showing Results 161 - 200, Page 5 of 18