9,222

Winchester, MA Homes

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  • 259 Washington St, Winchester, MA 01890
    259 Washington St, Winchester, MA 01890
    259 Washington St, Winchester, MA 01890
    /42

    $1,349,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,590 Sq Ft

    259 Washington St, Winchester, MA 01890

    Step into timeless charm in this STUNNING, impeccably maintained Dutch Colonial Revival home, where historic character meets modern living! Thoughtfully updated with 4 bedrooms and 4 baths, including TWO ENSUITE RETREATS—one private and perfect as a 4th bedroom, au pair suite, studio, or office. Endless flexibility! The updated kitchen shines with abundant cabinetry, center island, granite

    Agent Photo

    Laurie Cappuccio

    Classified Realty Group

    (781) 412-7772

    259 Washington St, Winchester, MA 01890
  • 416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    /20

    $2,458 - $11,422 per month plus fees

    Sanctuary Winchester West

    Studio - 3 Beds

    416 Cambridge St, Winchester, MA 01890

    The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

    416 Cambridge St, Winchester, MA 01890
  • 6 Francis Circuit Unit 6, Winchester, MA 01890
    6 Francis Circuit Unit 6, Winchester, MA 01890
    6 Francis Circuit Unit 6, Winchester, MA 01890
    /39

    $950,000 Sold Jul 17, 2025

    6 Francis Circuit Unit 6, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • Built 1875

    Last Sold Summary

    • 1% Below List Price
    • $617/SF
    • 10 Days On Market

    Last Listing Agent Katherine Waters-Clark Compass

    6 Francis Circuit Unit 6, Winchester, MA 01890
    • 9 Robinson Park, Winchester, MA 01890
      9 Robinson Park, Winchester, MA 01890
      9 Robinson Park, Winchester, MA 01890
      /42

      Est $1,696,756 Not Listed For Sale

      9 Robinson Park, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,224 Sq Ft
      • Built 1945
      9 Robinson Park, Winchester, MA 01890

      Last Sold Summary

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

      Last Sold Price $1,670,000

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

  • 20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    /36

    $3,600,000 Open Sun 12:30PM - 1:30PM

    • 6 Beds
    • 7 Baths
    • 8,866 Sq Ft

    20 Amberwood Dr, Winchester, MA 01890

    Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    (781) 678-8050

    20 Amberwood Dr, Winchester, MA 01890
  • 232 Washington St Unit 1, Winchester, MA 01890
    232 Washington St Unit 1, Winchester, MA 01890
    232 Washington St Unit 1, Winchester, MA 01890
    /10

    $2,600 total monthly price

    • 2 Beds
    • 1 Bath
    • 761 Sq Ft
    • Apartment for Rent

    232 Washington St Unit 1, Winchester, MA 01890

    JUNE 1ST 1ST FLOOR 5rm/2bd 1 bath with driveway. Eat in kitchen. Ceramic Tile Bathroom** Two good sized bedrooms with good closet space. Dining room and living room. Utilities are to be paid by tenant, heat is by oil. Separate driveway for you. Short distance to train, downtown and the pond. No pets preferred, but a cat will be considered.Washer and dryer for your use (neg) Modern Kitchen with

    Kelly Catallo Realty ONE Group Cosmopolitan

    232 Washington St Unit 1, Winchester, MA 01890
  • 45 Brooks St, Winchester, MA 01890
    45 Brooks St, Winchester, MA 01890
    45 Brooks St, Winchester, MA 01890
    /41

    $2,850,000 Sold Jun 09, 2025

    45 Brooks St, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 4,325 Sq Ft
    • Built 1953

    Last Sold Summary

    • 2% Below List Price
    • $659/SF
    • 8 Days On Market

    Current Estimated Value $2,733,525

    Last Listing Agent Kim Covino Compass

    45 Brooks St, Winchester, MA 01890
    • 23 Everett Ave, Winchester, MA 01890
      23 Everett Ave, Winchester, MA 01890
      23 Everett Ave, Winchester, MA 01890
      /42

      Est $3,166,357 Not Listed For Sale

      23 Everett Ave, Winchester, MA 01890

      • 6 Beds
      • 6 Baths
      • 4,714 Sq Ft
      • Built 1909
      23 Everett Ave, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $689/SF
      • 9 Days On Market

      Last Sold Price $3,250,000

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • 200 Swanton St Unit T28, Winchester, MA 01890
    200 Swanton St Unit T28, Winchester, MA 01890
    200 Swanton St Unit T28, Winchester, MA 01890
    /34

    $375,000 Pending

    • 1 Bed
    • 1 Bath
    • 634 Sq Ft

    200 Swanton St Unit T28, Winchester, MA 01890

    1 bedroom condo in Winchester. This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with access to the community pool and well-kept

    Agent Photo

    Joan Powell

    RE/MAX Andrew Realty Services

    (781) 384-5553

    200 Swanton St Unit T28, Winchester, MA 01890
  • 25-35 River St, Winchester, MA 01890
    25-35 River St, Winchester, MA 01890
    25-35 River St, Winchester, MA 01890
    /24

    $3,089 - $13,102 per month plus fees

    Sanctuary Winchester North

    1 - 3 Beds

    25-35 River St, Winchester, MA 01890

    The Sanctuary at Winchester North is designed for the way you live - casual fireside gatherings in the Den, a game of billiards in the Hive, a meal with friends prepared in the Nest's Chef's Kitchen. Maybe you prefer to make a splash in the pool, or stay on track with personal health goals in the fitness and health facility. With meticulously appointed common spaces designed for work, play, and

    25-35 River St, Winchester, MA 01890
  • 1 Saint Augustine Ct, Winchester, MA 01890
    1 Saint Augustine Ct, Winchester, MA 01890
    1 Saint Augustine Ct, Winchester, MA 01890
    /39

    $2,200,000 Sold Jun 30, 2025

    1 Saint Augustine Ct, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 3,818 Sq Ft
    • Built 1967

    Last Sold Summary

    • 10% Above List Price
    • $576/SF
    • 0 Days On Market

    Current Estimated Value $2,104,584

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    1 Saint Augustine Ct, Winchester, MA 01890
    • 17 Dix St, Winchester, MA 01890
      17 Dix St, Winchester, MA 01890
      17 Dix St, Winchester, MA 01890
      /42

      Est $2,309,715 Not Listed For Sale

      17 Dix St, Winchester, MA 01890

      • 5 Beds
      • 2 Baths
      • 3,059 Sq Ft
      • Built 1940
      17 Dix St, Winchester, MA 01890

      Last Sold Summary

      • 2% Below List Price
      • $768/SF
      • 6 Days On Market

      Last Sold Price $2,350,000

      Last Listing Agent Kim Covino Compass

  • 200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    /26

    $379,000

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 228, Winchester, MA 01890

    Newly Renovated 1-bedroom condo at Parkview Condominiums in Winchester. This bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with new flooring and excellent

    Agent Photo

    Joan Powell

    RE/MAX Andrew Realty Services

    (781) 417-5122

    200 Swanton St Unit 228, Winchester, MA 01890
  • 415 Washington St Unit 1, Winchester, MA 01890
    415 Washington St Unit 1, Winchester, MA 01890
    415 Washington St Unit 1, Winchester, MA 01890
    /16

    $2,600 total monthly price

    • 2 Beds
    • 1 Bath
    • Apartment for Rent

    415 Washington St Unit 1, Winchester, MA 01890

    At 1300sqft, this unit far exceeds the average size for a 2 bed 1 bath. Very well maintained and close to 93, yet neatly tucked away, parking space on the side street (off the main road). A second off-street parking spot is negotiable. Screened in backdoor area so you can be as close to comfort as possible. Once inside the space, you'll be greeted by large bedrooms, a cozy kitchen and your choice

    Thomas Tsui Keller Williams Realty

    415 Washington St Unit 1, Winchester, MA 01890
  • 6 Wyman Ct Unit 6, Winchester, MA 01890
    6 Wyman Ct Unit 6, Winchester, MA 01890
    6 Wyman Ct Unit 6, Winchester, MA 01890
    /35

    $1,379,000 Sold Jan 05, 2026

    6 Wyman Ct Unit 6, Winchester, MA 01890

    • 3 Beds
    • 4.5 Baths
    • 2,722 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $507/SF
    • 15 Days On Market

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    6 Wyman Ct Unit 6, Winchester, MA 01890
    • 299 Cross St Unit 299, Winchester, MA 01890
      299 Cross St Unit 299, Winchester, MA 01890
      299 Cross St Unit 299, Winchester, MA 01890
      /33

      Not Listed For Sale

      299 Cross St Unit 299, Winchester, MA 01890

      • 2 Beds
      • 1.5 Baths
      • 1,452 Sq Ft
      • Built 1960
      299 Cross St Unit 299, Winchester, MA 01890

      Last Sold Summary

      • $424/SF
      • 5 Days On Market

      Last Sold Price $615,000

      Last Listing Agent Patricia Nunez Redfin Corp.

  • 4 Leslie Rd, Winchester, MA 01890
    4 Leslie Rd, Winchester, MA 01890
    4 Leslie Rd, Winchester, MA 01890
    /42

    $1,999,900 Pending

    • 5 Beds
    • 3.5 Baths
    • 2,860 Sq Ft

    4 Leslie Rd, Winchester, MA 01890

    Set on a lush, private lot, this Royal Barry Wills home blends timeless design with extraordinary gardens. A welcoming mudroom opens to a cathedral-ceiling kitchen with slider framing views of the yard and perennial plantings. The dining room and front-to-back living room with fireplace and custom built-ins each offer sliders that extend living space outdoors and invite natural light throughout

    Anne Spry Barrett Sotheby's International Realty

    4 Leslie Rd, Winchester, MA 01890
  • 200 Swanton St Unit 310, Winchester, MA 01890
    200 Swanton St Unit 310, Winchester, MA 01890
    200 Swanton St Unit 310, Winchester, MA 01890
    /4

    $2,000 total monthly price

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    200 Swanton St Unit 310, Winchester, MA 01890

    NO BROKER FEE TO TENANT OWNER PAYS!Fee Disclosure:Last Month Rent: $2,000First Month Rent: $2,000Security Deposit: $1,000Disclaimer: Contact EDGE for more information on this listing, and hundreds of our other listings! See why more people are choosing the highest and most-reviewed real estate firm in Massachusetts. Brokerage fee applies. EDGE Realty Advisors is not

    200 Swanton St Unit 310, Winchester, MA 01890
  • 32 Clark St, Winchester, MA 01890
    32 Clark St, Winchester, MA 01890
    32 Clark St, Winchester, MA 01890
    /33

    $699,900 Sold May 30, 2025

    32 Clark St, Winchester, MA 01890

    • 2 Beds
    • 1.5 Baths
    • 1,326 Sq Ft
    • Built 1890

    Last Sold Summary

    • $528/SF
    • 4 Days On Market

    Current Estimated Value $751,539

    Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

    32 Clark St, Winchester, MA 01890
    • 38 Winthrop Street Extension, Winchester, MA 01890
      38 Winthrop Street Extension, Winchester, MA 01890
      38 Winthrop Street Extension, Winchester, MA 01890
      /39

      Est $2,319,501 Not Listed For Sale

      38 Winthrop Street Extension, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 4,539 Sq Ft
      • Built 2020
      38 Winthrop Street Extension, Winchester, MA 01890

      Last Sold Summary

      • 16% Above List Price
      • $441/SF
      • 48 Days On Market

      Last Sold Price $2,000,000

      Last Listing Agent Ryan Wilson Keller Williams Realty

  • 19 Town Way, Winchester, MA 01890
    19 Town Way, Winchester, MA 01890
    19 Town Way, Winchester, MA 01890
    /42

    $2,899,000 Pending

    • 5 Beds
    • 5.5 Baths
    • 5,257 Sq Ft

    19 Town Way, Winchester, MA 01890

    Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive

    Philip Vita Compass

    19 Town Way, Winchester, MA 01890
  • 200 Swanton St Unit T37, Winchester, MA 01890
    200 Swanton St Unit T37, Winchester, MA 01890
    200 Swanton St Unit T37, Winchester, MA 01890
    /15

    $2,750 total monthly price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    200 Swanton St Unit T37, Winchester, MA 01890

    ALL UTILITIES INCLUDED!!!! Ground Level with Private Entrance. NO STAIRS! Lovely terrace level unit at Parkview available 5/1 This immaculate and well cared for home includes dishwasher, on site laundry, parking,Situated in a very convenient location, near everything! Enjoy the beautifully landscaped common area with pool, cabana and picnic table. Super Value with ALL UTILITIES INCLUDED make this

    Mary Doyle Berkshire Hathaway HomeServices Commonwealth Real Estate

    200 Swanton St Unit T37, Winchester, MA 01890
  • 104 Church St, Winchester, MA 01890
    104 Church St, Winchester, MA 01890
    104 Church St, Winchester, MA 01890
    /42

    $1,255,000 Sold Jan 07, 2026

    104 Church St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,696 Sq Ft
    • Built 1897

    Last Sold Summary

    • 10% Below List Price
    • $466/SF
    • 46 Days On Market

    Current Estimated Value $1,349,179

    Last Listing Agent Kim Covino Compass

    104 Church St, Winchester, MA 01890
    • 897 Main St Unit 1, Winchester, MA 01890
      897 Main St Unit 1, Winchester, MA 01890
      897 Main St Unit 1, Winchester, MA 01890
      /34

      Est $868,008 Not Listed For Sale

      897 Main St Unit 1, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,584 Sq Ft
      • Built 2014
      897 Main St Unit 1, Winchester, MA 01890

      Last Sold Summary

      • 7% Above List Price
      • $511/SF
      • 74 Days On Market

      Last Sold Price $810,000

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 171 Swanton St Unit 21, Winchester, MA 01890
    171 Swanton St Unit 21, Winchester, MA 01890
    171 Swanton St Unit 21, Winchester, MA 01890
    /40

    $749,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,834 Sq Ft

    171 Swanton St Unit 21, Winchester, MA 01890

    Welcome to The Village at 171 Swanton St, # 21! This end unit town home has everything you have been looking for in Winchester! The layout will afford you comfort & flexibility with the kitchen opening into dining room. Kitchen features upgraded counters, cabinets, crown molding and stainless appliances. Enjoy the use of your private patio just off of the dining room. An oversized family room

    Jesse Mason Colby Hunter Realty

    171 Swanton St Unit 21, Winchester, MA 01890
  • 5 Sheridan Cir Unit 5, Winchester, MA 01890
    5 Sheridan Cir Unit 5, Winchester, MA 01890
    5 Sheridan Cir Unit 5, Winchester, MA 01890
    /26

    $4,200 total monthly price

    • 4 Beds
    • 2 Baths
    • 1,786 Sq Ft
    • Townhouse for Rent

    5 Sheridan Cir Unit 5, Winchester, MA 01890

    $4,200month, Beautiful newly renovated side by side 3 level townhouse, 1768 sqft, featuring 4 Bedrooms, 2 full bathrooms, walk in closet, high ceiling, huge kitchen with lots of storage, entire hardwood floor. Top rated school system and great location. Minutes walking distance to daycares and Lynch elementary School. About 15 minutes walking distance to Winchester high school. Near bus stop,

    5 Sheridan Cir Unit 5, Winchester, MA 01890
  • 7 Trinity Rd, Winchester, MA 01890
    7 Trinity Rd, Winchester, MA 01890
    7 Trinity Rd, 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 $1,223,372

    Last Listing Agent Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
    • 228 Ridge St, Winchester, MA 01890
      228 Ridge St, Winchester, MA 01890
      228 Ridge St, Winchester, MA 01890
      /42

      Est $2,850,771 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

      • 14% Above List Price
      • $399/SF
      • 142 Days On Market

      Last Sold Price $2,499,000

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

  • 10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    /42

    $2,499,000 Open Sat 11AM - 12:30PM

    • 4 Beds
    • 4 Baths
    • 5,674 Sq Ft

    10 Viking Rd, Winchester, MA 01890

    Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

    Anne Spry Barrett Sotheby's International Realty

    10 Viking Rd, Winchester, MA 01890
  • 8 Richardson St Unit 2, Winchester, MA 01890
    8 Richardson St Unit 2, Winchester, MA 01890
    8 Richardson St Unit 2, Winchester, MA 01890
    /38

    $4,500 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,811 Sq Ft
    • Condo for Rent

    8 Richardson St Unit 2, Winchester, MA 01890

    Beautiful, high end two story condo for rent; close to everything Winchester has to offer! This unique penthouse dulpex condo offers all the space of a single family home with an open concept floor plan featuring high end finishes and hardwood floors throughout. Enjoy a private entrance, a stunning living room w/ high ceilings, a beautiful gas fireplace and high end buit ins; chefs kitchen

    Kim Covino Compass

    8 Richardson St Unit 2, Winchester, MA 01890
  • 163 Main St, Winchester, MA 01890
    163 Main St, Winchester, MA 01890
    163 Main St, Winchester, MA 01890
    /36

    $1,175,000 Sold Aug 18, 2025

    163 Main St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,335 Sq Ft
    • Built 1961

    Last Sold Summary

    • 18% Above List Price
    • $503/SF
    • 8 Days On Market

    Current Estimated Value $1,184,815

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    163 Main St, Winchester, MA 01890
    • 15 Wincrest Dr, Winchester, MA 01890
      15 Wincrest Dr, Winchester, MA 01890
      15 Wincrest Dr, Winchester, MA 01890
      /40

      Est $1,351,087 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

      • 7% Above List Price
      • $498/SF
      • 4 Days On Market

      Last Sold Price $1,260,000

      Last Listing Agent Kim Covino Compass

  • 149 Horn Pond Brook Rd, Winchester, MA 01890
    149 Horn Pond Brook Rd, Winchester, MA 01890
    149 Horn Pond Brook Rd, Winchester, MA 01890
    /34

    $1,095,000 Open Fri 5:30PM - 6:30PM

    • 5 Beds
    • 2 Baths
    • 2,331 Sq Ft

    149 Horn Pond Brook Rd, Winchester, MA 01890

    Picture-perfect Cape Cod single family home on a corner lot across the street from the brand new Lynch Elementary School. This special residence is much larger than it looks & has 4–5 spacious bedrooms across two levels & two full baths on each floor. Such space offers versatility with 2 beds on main level & 3 bedrooms on the upper floor. The sun-filled living room flows nicely to a charming

    Nancy McLaughlin Redfin Corp.

    149 Horn Pond Brook Rd, Winchester, MA 01890
  • 200 Swanton St Unit 3, Winchester, MA 01890
    200 Swanton St Unit 3, Winchester, MA 01890
    200 Swanton St Unit 3, Winchester, MA 01890
    /8

    $2,000 total monthly price

    • 1 Bed
    • 1 Bath
    • 9,999 Sq Ft
    • Condo for Rent

    200 Swanton St Unit 3, Winchester, MA 01890

    All utilities are included and 1 parking space included! NO BROKER'S FEE.

    200 Swanton St Unit 3, Winchester, MA 01890
  • 8 Felsdale Close, Winchester, MA 01890
    8 Felsdale Close, Winchester, MA 01890
    8 Felsdale Close, Winchester, MA 01890
    /3

    $1,930,000 Sold Jan 09, 2026

    8 Felsdale Close, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 3,658 Sq Ft
    • Built 1935

    Last Sold Summary

    • 7% Below List Price
    • $528/SF
    • 35 Days On Market

    Current Estimated Value $1,939,907

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    8 Felsdale Close, Winchester, MA 01890
    • 10 Carriage Ln, Winchester, MA 01890
      10 Carriage Ln, Winchester, MA 01890
      10 Carriage Ln, Winchester, MA 01890
      /33

      Est $1,450,343 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

      • 2% Above List Price
      • $698/SF
      • 5 Days On Market

      Last Sold Price $1,420,000

      Last Listing Agent Peter Kasseris Serhant

  • 1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    /40

    $1,899,000 Open Sun 1:30PM - 3PM

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

    1 Town Way, Winchester, MA 01890

    Welcome home to this completely renovated gem, ideally situated 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 buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy

    Philip Vita Compass

    1 Town Way, Winchester, MA 01890
  • 6 Skillings Rd Unit 1, Winchester, MA 01890
    6 Skillings Rd Unit 1, Winchester, MA 01890
    6 Skillings Rd Unit 1, Winchester, MA 01890
    /8

    $2,400 total monthly price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Apartment for Rent

    6 Skillings Rd Unit 1, Winchester, MA 01890

    Great sunny two bedroom with high ceilings, open living/ kitchen, good size bedrooms, laundry in the unit, central a/c and one off street parking spot.

    Kristen Day RE/MAX Realty Plus

    6 Skillings Rd Unit 1, Winchester, MA 01890
  • 4 Olde Lyme Rd, Winchester, MA 01890
    4 Olde Lyme Rd, Winchester, MA 01890
    4 Olde Lyme Rd, Winchester, MA 01890
    /25

    $1,881,900 Sold May 30, 2025

    4 Olde Lyme Rd, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 3,488 Sq Ft
    • Built 1980

    Last Sold Summary

    • 1% Below List Price
    • $540/SF
    • 34 Days On Market

    Current Estimated Value $1,832,690

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    4 Olde Lyme Rd, Winchester, MA 01890
    • 28 Thornberry Rd, Winchester, MA 01890
      28 Thornberry Rd, Winchester, MA 01890
      28 Thornberry Rd, Winchester, MA 01890
      /29

      Est $1,329,799 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

      • $595/SF
      • 117 Days On Market

      Last Sold Price $1,335,000

      Last Listing Agent Shaundize Moosavizadeh Coldwell Banker Realty - Boston

Showing Results 1 - 40, Page 1 of 18

Massachusetts Middlesex County Winchester

Real Estate & Homes

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 21 days on the market compared to the national average of 55 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,605,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,605,000
Median Single Family Sale Price
$1,750,000
Median Townhouse Sale Price
$1,305,000
Median 2 Bedroom Sale Price
$770,000
Average Price Per Sq Ft
$563
Number of Homes for Sale
26
Last 12 months Home Sales
176
Months of Supply
1.80
Median List Price
$1,669,444
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-3%
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