Winchester, MA Homes

• 

  

  

  /23

  Est $966,857 Not Listed For Sale

  12 James St, Winchester, MA 01890

  • 3 Beds
  • 1.5 Baths
  • 1,548 Sq Ft
  • Built 1950

  12 James St, Winchester, MA 01890

  Last Sold Summary

  • 14% Above List Price
  • $548/SF
  • 25 Days On Market

  Last Sold Price $849,000

  Last Listing Agent Gigi Nguyen Harmony Hill Realty LLC
• 

  

  

  /42

  $1,350,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,153 Sq Ft

  6 Marchant Rd, Winchester, MA 01890

  Updated / move in ready 3 bed, 2.5 bath home *Set on a generous 11K lot* in a fantastic Winchester location/ Lincoln Elementary close to town, schools, train & Boston. The first floor offers an ideal layout w gleaming hardwood floors, updated kitchen w/stainless steel appliances & island seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc & dining room.

  Kim Covino Compass

  6 Marchant Rd, Winchester, MA 01890
• 

  

  

  /32

  $1,250,000 Sold Jun 30, 2025

  80 Harvard St, Winchester, MA 01890

  • 4 Beds
  • 2 Baths
  • 2,759 Sq Ft
  • Built 1973

  Last Sold Summary

  • 4% Above List Price
  • $453/SF
  • 6 Days On Market

  Current Estimated Value $1,259,412

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

  80 Harvard St, Winchester, MA 01890
• 

  

  

  /42

  Est $925,522 Not Listed For Sale

  25 Henry St, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 3,890 Sq Ft
  • Built 2021

  25 Henry St, Winchester, MA 01890

  Last Sold Summary

  • 39% Below List Price
  • $388/SF
  • 3 Days On Market

  Last Sold Price $1,510,000

  Last Listing Agent Karima Alami Compass
• 

  

  

  /42

  $3,499,000

  • 5 Beds
  • 7.5 Baths
  • 6,899 Sq Ft

  54 Johnson Rd, Winchester, MA 01890

  This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the

  Kim Covino Compass

  54 Johnson Rd, 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 $2,253,239

  Last Listing Agent Karima Alami Compass

  30 Prospect St, Winchester, MA 01890
• 

  

  /26

  Est $833,341 Not Listed For Sale

  28 Henry St, Winchester, MA 01890

  • 2 Beds
  • 1 Bath
  • 1,279 Sq Ft
  • Built 1942

  28 Henry St, Winchester, MA 01890

  Last Sold Summary

  • 17% Above List Price
  • $559/SF
  • 5 Days On Market

  Last Sold Price $715,000

  Last Listing Agent Alison Socha Leading Edge Real Estate
• 

  

  /26

  $2,699,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,255 Sq Ft

  2 Priscilla Ln, Winchester, MA 01890

  Under construction / Beautifully crafted 4 bedroom home offering thoughtful design, quality finishes & an ideal layout. The open-concept 1st floor is both spacious & welcoming, perfect for entertaining & everyday living. The chef’s kitchen features quartz countertops, stainless appliances, large center island w/seating & pantry. The kitchen flows seamlessly into the generous family room w/ gas

  Kim Covino Compass

  2 Priscilla Ln, Winchester, MA 01890
• 

  

  /16

  $1,050,000 Sold Jul 11, 2025

  61 Westland Ave, Winchester, MA 01890

  • 4 Beds
  • 2 Baths
  • 2,621 Sq Ft
  • Built 1952

  Last Sold Summary

  • 16% Below List Price
  • $401/SF
  • 48 Days On Market

  Current Estimated Value $1,682,353

  Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  61 Westland Ave, Winchester, MA 01890
• 

  

  /42

  Est $1,490,807 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

  • 2% Below List Price
  • $491/SF
  • 7 Days On Market

  Last Sold Price $1,517,500

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

  

  /42

  $3,537,000 Open Sun 12PM - 1PM

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

  37 Mayflower Rd, Winchester, MA 01890

  Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

  Kim Covino Compass

  37 Mayflower Rd, 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 $1,096,432

  Last Listing Agent Oliver Koester Compass

  5 Cutting St, Winchester, MA 01890
• 

  

  /20

  Est $1,070,607 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

  • 12% Above List Price
  • $670/SF
  • 35 Days On Market

  Last Sold Price $960,000

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

  

  /25

  $999,000 Open Sat 12PM - 1:30PM

  • 4 Beds
  • 2 Baths
  • 1,552 Sq Ft

  76 Woodside Rd, Winchester, MA 01890

  Welcome to this charming 4-bedroom, 2-bath home in desirable Winchester. Ideally located in one of the town’s most sought-after neighborhoods, this well-maintained residence offers the perfect blend of classic character and everyday comfort. The home features a bright and inviting layout with generous living spaces, hardwood floors, bookshelves and windows seats. The kitchen flows seamlessly into

  Michael Pierce Mystic Properties Real Estate

  76 Woodside Rd, 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 $674,496

  Last Listing Agent Brian Woods Woods Properties Inc.

  7 Conant Rd Unit 20, Winchester, MA 01890
• 

  

  /17

  Est $2,110,564 Not Listed For Sale

  21 Dunster Ln, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 3,578 Sq Ft
  • Built 1950

  21 Dunster Ln, Winchester, MA 01890

  Last Sold Summary

  • 6% Above List Price
  • $559/SF
  • 9 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Mark Donnellan Gibson Sotheby's International Realty
• 

  /2

  $359,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  20 Arthur St, Winchester, MA 01890

  Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

  Dan O'Connell LAER Realty Partners

  20 Arthur St, Winchester, MA 01890
• 

  

  /42

  $2,111,000 Sold Jun 05, 2025

  14 Grove St, Winchester, MA 01890

  • 5 Beds
  • 4 Baths
  • 4,744 Sq Ft
  • Built 1922

  Last Sold Summary

  • 8% Above List Price
  • $445/SF
  • 6 Days On Market

  Current Estimated Value $2,100,387

  Last Listing Agent Kim Covino Compass

  14 Grove St, Winchester, MA 01890
• 

  

  /38

  Est $1,192,174 Not Listed For Sale

  18 Ridge St, Winchester, MA 01890

  • 5 Beds
  • 1.5 Baths
  • 2,383 Sq Ft
  • Built 1840

  18 Ridge St, Winchester, MA 01890

  Last Sold Summary

  • 14% Above List Price
  • $441/SF
  • 15 Days On Market

  Last Sold Price $1,050,000

  Last Listing Agent Gayle Winters Compass
• 

  

  /16

  $2,799,000 Open Sat 12PM - 1PM

  • 5 Beds
  • 4 Baths
  • 5,083 Sq Ft

  53 Winford Way, Winchester, MA 01890

  Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient

  Andersen Group Realty Keller Williams Realty Boston Northwest

  53 Winford 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

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

  20 Foxcroft Rd, Winchester, MA 01890
• 

  

  /40

  Est $2,412,180 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

  • 22% Above List Price
  • $316/SF
  • 136 Days On Market

  Last Sold Price $1,980,000

  Last Listing Agent Anthony Marino The Marino Group Collection
• 

  

  /42

  $1,599,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,343 Sq Ft

  263 Highland Ave, Winchester, MA 01890

  Great new price, below assessed value!!! Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining,

  Seeme Moreira Coldwell Banker Realty - Lexington

  263 Highland Ave, 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 $1,895,701

  Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  20 Grayson Rd, Winchester, MA 01890
• 

  

  /42

  Est $2,069,175 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

  • 2% Above List Price
  • $405/SF
  • 8 Days On Market

  Last Sold Price $2,025,000

  Last Listing Agent Ngoc Anh Goldstein Leading Edge Real Estate
• 

  

  /26

  $1,499,999

  • 6 Beds
  • 3 Baths
  • 2,658 Sq Ft

  65 High St, Winchester, MA 01890

  Fantastic! The best value in Winchester in a desired neighborhood. The sunny first floor flows nicely from room to room, with hardwood floors in the living areas and a hallway leading to the 3 original bedrooms. Ideal for an office, guests, or visiting in-laws. A screen porch and patio off the dining room ideal for al fresco dining. The generous second-floor renovation features a full bath with

  Anna Jung K Stadium Realty INC

  65 High St, Winchester, MA 01890
• 

  

  /42

  $3,745,000 Sold Aug 08, 2025

  25 Wedgemere Ave, Winchester, MA 01890

  • 7 Beds
  • 8 Baths
  • 7,587 Sq Ft
  • Built 2010

  Last Sold Summary

  • 6% Below List Price
  • $494/SF
  • 44 Days On Market

  Current Estimated Value $3,933,190

  Last Listing Agent Prestige Homes Realty Team Prestige Homes Real Estate, LLC

  25 Wedgemere Ave, Winchester, MA 01890
• 

  

  /38

  Est $1,706,087 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

  • 3% Above List Price
  • $522/SF
  • 6 Days On Market

  Last Sold Price $1,650,000

  Last Listing Agent Philip Vita Compass
• 

  

  /37

  $1,599,000

  • 4 Beds
  • 2.5 Baths
  • 3,380 Sq Ft

  34 Robinhood Rd, Winchester, MA 01890

  This spacious four bedroom Colonial is located in the desirable westside neighborhood and Ambrose school. The first level has a fully applianced kitchen followed by a oversized dining room. There is a wood burning fireplace in the spacious living room. A family room is off the kitchen and also an office and half-bath completes this level. The second level has four very large bedrooms. The main

  Janet Halloran RE/MAX Real Estate Center

  34 Robinhood Rd, Winchester, MA 01890
• 

  

  /31

  $1,965,000 Sold Jan 27, 2026

  46 Church St, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,475 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Below List Price
  • $565/SF
  • 13 Days On Market

  Current Estimated Value $1,969,459

  Last Listing Agent Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

  46 Church St, Winchester, MA 01890
• 

  

  /40

  Est $2,094,172 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

  • 10% Above List Price
  • $418/SF
  • 4 Days On Market

  Last Sold Price $1,910,000

  Last Listing Agent Doug Hills Compass
• 

  

  /37

  $1,799,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,910 Sq Ft

  58 Jefferson Rd, Winchester, MA 01890

  This well-maintained colonial is tucked at the end of a cul-de-sac in a very desirable neighborhood. Upon entering, the bright foyer with hardwood floors opens to a spacious front to back living room. The formal dining room leads to the eat in kitchen, perfect for entertaining and gatherings. Just off the kitchen the family room features a stone fireplace and sliding doors leading to the deck and

  Stephanie Macfarland Wilson Wolfe Real Estate

  58 Jefferson Rd, Winchester, MA 01890
• 

  

  /42

  $682,000 Sold Mar 28, 2025

  7 Conant Rd Unit 24, Winchester, MA 01890

  • 2 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Below List Price
  • $570/SF
  • 68 Days On Market

  Current Estimated Value $693,672

  Last Listing Agent Paul Bettencourt Beaudoin & Associates, REALTOR®

  7 Conant Rd Unit 24, Winchester, MA 01890
• 

  

  /42

  Est $1,204,289 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

  • 17% Above List Price
  • $403/SF
  • 31 Days On Market

  Last Sold Price $1,025,000

  Last Listing Agent Charles Jolin Keller Williams Realty
• 

  

  /35

  $1,060,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,849 Sq Ft

  62 Richardson St, Winchester, MA 01890

  Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is perfectly situated on a large corner lot. Venture into Unit 1 through the all seasons porch. The kitchen offers ample cabinet space, center island, & breakfast nook. Two bedrooms on level 1, both w/ ample closet storage. Full bath w/

  Frank Ventresca Strategy Street

  62 Richardson St, Winchester, MA 01890
• 

  

  /28

  $710,000 Sold Sep 10, 2025

  666 Main St Unit 206, Winchester, MA 01890

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft
  • Built 1982

  Last Sold Summary

  • 2% Below List Price
  • $607/SF
  • 50 Days On Market

  Current Estimated Value $716,555

  Last Listing Agent Sveta Vakhitova Berkshire Hathaway HomeServices Warren Residential

  666 Main St Unit 206, Winchester, MA 01890
• 

  

  /41

  Est $3,689,513 Not Listed For Sale

  11 Viking Rd, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 4,322 Sq Ft
  • Built 1980

  11 Viking Rd, Winchester, MA 01890

  Last Sold Summary

  • 148% Above List Price
  • $344/SF
  • 9 Days On Market

  Last Sold Price $1,485,000

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

  

  /13

  $3,199,000 Pending

  • 6 Beds
  • 7 Baths
  • 5,709 Sq Ft

  39 Town Way, Winchester, MA 01890

  Discover all this gorgeous new construction home in top East Side location will offer! Designed with today’s lifestyle in mind, this home features a flexible open floor plan perfect for entertaining & everyday living / A great opportunity for you to customize the finishes & bring your vision to life! First floor offers a mudroom, half bath, office/living room, bedroom w/ full bath & a stunning

  Kim Covino Compass

  39 Town Way, Winchester, MA 01890
• 

  

  /35

  $1,100,000 Sold Jun 27, 2025

  63 Church St, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 3,157 Sq Ft
  • Built 1866

  Last Sold Summary

  • 24% Below List Price
  • $348/SF
  • 20 Days On Market

  Current Estimated Value $1,169,959

  Last Listing Agent Nancy McLaughlin Redfin Corp.

  63 Church St, Winchester, MA 01890
• 

  

  /40

  Est $1,367,976 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

  • 11% Above List Price
  • $501/SF
  • 12 Days On Market

  Last Sold Price $1,230,000

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

Showing Results 161 - 200, Page 5 of 18