9,206

Winchester, MA Homes

Section Image Section Image
  • 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

    $375,000 Open Thu 5PM - 6:30PM

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 228, Winchester, MA 01890

    This one bed one bath, 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 closet space, freshly painted throughout all rooms, and

    Agent Photo

    Joan Powell

    RE/MAX Andrew Realty Services

    (781) 417-5122

    200 Swanton St Unit 228, Winchester, MA 01890
  • 200 Swanton St Unit 704, Winchester, MA 01890
    200 Swanton St Unit 704, Winchester, MA 01890
    200 Swanton St Unit 704, Winchester, MA 01890
    /16

    $1,890 Per Month

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

    200 Swanton St Unit 704, Winchester, MA 01890

    TOP FLOOR UNIT. HEAT, HOT WATER, AC AND ELECTRIC INCLUDED. This studio apartment offers comfort, convenience, and a scenic setting overlooking the beautiful Parkview duck pond. Balcony, access to an outdoor pool and well-maintained landscaped grounds. Off-street parking is included, and laundry facilities are conveniently located within the building. This professionally managed community is

    Agent Photo

    Joan Powell

    RE/MAX Andrew Realty Services

    (781) 725-5123

    200 Swanton St Unit 704, 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
    • 322 Cambridge St, Winchester, MA 01890
      322 Cambridge St, Winchester, MA 01890
      322 Cambridge St, Winchester, MA 01890
      /15

      Est $1,183,566 Not Listed For Sale

      322 Cambridge St, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,172 Sq Ft
      • Built 1985
      322 Cambridge St, Winchester, MA 01890

      Last Sold Summary

      • 9% Above List Price
      • $501/SF
      • 6 Days On Market
      • Last Sold Price $1,088,000
      • May 08, 2025

      Last Listing Agent Joanne McDonnell RE/MAX Real Estate Center

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

    $3,600,000

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

    Starting at $2,894 Plus Fees

    • 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.

    Sanctuary Winchester West

    (339) 214-9536

    416 Cambridge St, 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 $2,800,479

    Last Listing Agent Kim Covino Compass

    45 Brooks St, Winchester, MA 01890
    • 88 Arlington St, Winchester, MA 01890
      88 Arlington St, Winchester, MA 01890
      88 Arlington St, Winchester, MA 01890
      /42

      Est $2,218,277 Not Listed For Sale

      88 Arlington St, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 4,097 Sq Ft
      • Built 1939
      88 Arlington St, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $537/SF
      • 24 Days On Market
      • Last Sold Price $2,200,000
      • May 09, 2025

      Last Listing Agent Kim Covino Compass

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

    $1,874,000

    • 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
  • 200 Swanton St Unit 237, Winchester, MA 01890
    200 Swanton St Unit 237, Winchester, MA 01890
    200 Swanton St Unit 237, Winchester, MA 01890
    /14

    $2,600 Per Month

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

    200 Swanton St Unit 237, Winchester, MA 01890

    Sunny & Bright 2-Bedroom Condo in Winchester Park View – Available 05/15. Enjoy comfortable living in this updated and sunny 2-bedroom, 1-bathroom condo. Private balcony. Heat, electricity, hot water, and more included in rent. 2 parking spaces. Ground maintenance and trash removal included. Conveniently located near shopping, restaurants, and Winchester Town Center. Just a short walk to the

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    (781) 734-6553

    200 Swanton St Unit 237, Winchester, MA 01890
  • 12 Thornberry Rd, Winchester, MA 01890
    12 Thornberry Rd, Winchester, MA 01890
    12 Thornberry Rd, 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 $1,215,721

    Last Listing Agent Kim Covino Compass

    12 Thornberry Rd, Winchester, MA 01890
    • 48 Wedgemere Ave, Winchester, MA 01890
      48 Wedgemere Ave, Winchester, MA 01890
      48 Wedgemere Ave, Winchester, MA 01890
      /42

      Est $2,434,503 Not Listed For Sale

      48 Wedgemere Ave, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,173 Sq Ft
      • Built 1914
      48 Wedgemere Ave, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $580/SF
      • 8 Days On Market
      • Last Sold Price $2,420,000
      • Apr 25, 2025

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

  • 94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    /41

    $1,849,999

    • 4 Beds
    • 3 Baths
    • 3,512 Sq Ft

    94 Johnson Rd, Winchester, MA 01890

    This quintessential Colonial blends timeless charm with modern updates, offering a truly move-in ready home in a unique location! Directly across the street, the Winchester Swim and Tennis Club presents a rare opportunity for immediate membership—enjoy your own private club lifestyle just in time for summer. Just a few doors from Vinson-Owen Elementary. Wright-Locke Farm is just up the road.

    Philip Vita Compass

    94 Johnson Rd, 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

    Starting at $3,098 Plus Fees

    • 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

    Sanctuary Winchester North

    (781) 776-5329

    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 $2,156,313

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    1 Saint Augustine Ct, Winchester, MA 01890
    • 19 Rangeley Rd, Winchester, MA 01890
      19 Rangeley Rd, Winchester, MA 01890
      19 Rangeley Rd, Winchester, MA 01890
      /39

      Est $4,522,644 Not Listed For Sale

      19 Rangeley Rd, Winchester, MA 01890

      • 5 Beds
      • 7 Baths
      • 7,779 Sq Ft
      • Built 1915
      19 Rangeley Rd, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $598/SF
      • 5 Days On Market
      • Last Sold Price $4,650,000
      • May 01, 2025

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • 37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    /40

    $3,379,000

    • 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
  • 200 Swanton St Unit 635, Winchester, MA 01890
    200 Swanton St Unit 635, Winchester, MA 01890
    200 Swanton St Unit 635, Winchester, MA 01890
    /14

    $2,600 Per Month

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

    200 Swanton St Unit 635, Winchester, MA 01890

    ALL UTILITIES INCLUDED. Spacious 2-bedroom, 1-bath unit in a peaceful, park-like setting overlooking the duck pond. Features a well-designed layout, a balcony for relaxing outdoor space. Both bedrooms are a good size with closet space. Professionally managed community with on-site laundry, outdoor pool, landscaped grounds, and off-street parking. Conveniently located near downtown Winchester,

    Agent Photo

    Joan Powell

    RE/MAX Andrew Realty Services

    (855) 626-4977

    200 Swanton St Unit 635, 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
    • 24 Water St, Winchester, MA 01890
      24 Water St, Winchester, MA 01890
      24 Water St, Winchester, MA 01890
      /36

      Est $1,615,206 Not Listed For Sale

      24 Water St, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,809 Sq Ft
      • Built 2004
      24 Water St, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $570/SF
      • 7 Days On Market
      • Last Sold Price $1,600,000
      • Apr 30, 2025

      Last Listing Agent Domingo Medina Coldwell Banker Realty - Lexington

  • 2 Edgewater Place, Winchester, MA 01890
    2 Edgewater Place, Winchester, MA 01890
    2 Edgewater Place, Winchester, MA 01890
    /32

    $2,700,000

    • 4 Beds
    • 4.5 Baths
    • 3,945 Sq Ft

    2 Edgewater Place, Winchester, MA 01890

    A quiet cul-de-sac near the Mystic Lakes sets the stage for this exceptional Royal Barry Wills residence, masterfully reimagined. Every inch reflects elevated craftsmanship and a refined sense of luxury, with bespoke finishes and thoughtfully curated amenities throughout. The main level unfolds with effortless elegance, anchored by a state-of-the-art chef’s kitchen featuring custom cabinetry,

    Nancy Pallotta Gibson Sotheby's International Realty

    2 Edgewater Place, Winchester, MA 01890
  • 2 Elmwood Ave Unit 13, Winchester, MA 01890
    2 Elmwood Ave Unit 13, Winchester, MA 01890
    2 Elmwood Ave Unit 13, Winchester, MA 01890
    /20

    $1,500 Plus Fees

    • Studio
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 13, Winchester, MA 01890

    This Studio 1 bath in Winchester is available Now. Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions at the time the information was obtained. We are pledged to

    (781) 604-8381

    2 Elmwood Ave Unit 13, 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 $760,022

    Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

    32 Clark St, Winchester, MA 01890
    • 21 Shepard Ct, Winchester, MA 01890
      21 Shepard Ct, Winchester, MA 01890
      21 Shepard Ct, Winchester, MA 01890
      /36

      Est $712,764 Not Listed For Sale

      21 Shepard Ct, Winchester, MA 01890

      • 2 Beds
      • 1 Bath
      • 1,393 Sq Ft
      • Built 1890
      21 Shepard Ct, Winchester, MA 01890

      Last Sold Summary

      • 2% Below List Price
      • $524/SF
      • 7 Days On Market
      • Last Sold Price $730,000
      • May 01, 2025

      Last Listing Agent Abe Guillen Encore Realty

  • 2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    /41

    $3,747,000

    • 7 Beds
    • 6 Baths
    • 7,043 Sq Ft

    2 Everett Ave, Winchester, MA 01890

    Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end

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

    2 Everett Ave, 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

    (781) 604-1321

    200 Swanton St Unit 310, 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 $1,355,874

    Last Listing Agent Kim Covino Compass

    104 Church St, Winchester, MA 01890
    • 18 Pine Grove Park, Winchester, MA 01890
      18 Pine Grove Park, Winchester, MA 01890
      18 Pine Grove Park, Winchester, MA 01890
      /27

      Est $1,037,668 Not Listed For Sale

      18 Pine Grove Park, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,873 Sq Ft
      • Built 1958
      18 Pine Grove Park, Winchester, MA 01890

      Last Sold Summary

      • 6% Above List Price
      • $339/SF
      • 5 Days On Market
      • Last Sold Price $975,000
      • May 07, 2025

      Last Listing Agent Michele Forester EXIT Premier Real Estate

  • 9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    /10

    $3,400,000

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

    9 Albamont Rd, Winchester, MA 01890

    Brand new high end construction in prime Winchester location! Currently under construction w/ completion expected late spring 2026. A thoughtfully designed home with immense curb appeal showcasing 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 designer

    Kim Covino Compass

    9 Albamont Rd, Winchester, MA 01890
  • 282 High St, Winchester, MA 01890
    282 High St, Winchester, MA 01890
    282 High St, Winchester, MA 01890
    /27

    $10,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 6,583 Sq Ft
    • House for Rent

    282 High St, Winchester, MA 01890

    Fabulous 6 month rental opportunity with full additional in-law suite with private kitchen, bedroom, bath, and laundry. Very generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and

    Anthony Marino The Marino Group Collection

    282 High St, Winchester, MA 01890
  • 17 Cranston Rd, Winchester, MA 01890
    17 Cranston Rd, Winchester, MA 01890
    17 Cranston Rd, Winchester, MA 01890
    /39

    $1,560,000 Sold Apr 30, 2026

    17 Cranston Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,578 Sq Ft
    • Built 1950

    Last Sold Summary

    • $605/SF
    • 5 Days On Market

    Current Estimated Value $1,625,568

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    17 Cranston Rd, Winchester, MA 01890
    • 22 Standish Ln, Winchester, MA 01890
      22 Standish Ln, Winchester, MA 01890
      22 Standish Ln, Winchester, MA 01890
      /38

      Est $2,776,528 Not Listed For Sale

      22 Standish Ln, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 5,044 Sq Ft
      • Built 2025
      22 Standish Ln, Winchester, MA 01890

      Last Sold Summary

      • 3% Below List Price
      • $565/SF
      • 5 Days On Market
      • Last Sold Price $2,850,000
      • May 07, 2025

      Last Listing Agent Michaela Mahtani Leading Edge Real Estate

  • 27 Everett Ave, Winchester, MA 01890
    27 Everett Ave, Winchester, MA 01890
    27 Everett Ave, Winchester, MA 01890
    /39

    $3,290,000

    • 6 Beds
    • 5.5 Baths
    • 7,431 Sq Ft

    27 Everett Ave, Winchester, MA 01890

    This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are

    Nancy Pallotta Gibson Sotheby's International Realty

    27 Everett Ave, Winchester, MA 01890
  • 19 Irving St Unit 3, Winchester, MA 01890
    19 Irving St Unit 3, Winchester, MA 01890
    19 Irving St Unit 3, Winchester, MA 01890
    /8

    $2,495

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    19 Irving St Unit 3, Winchester, MA 01890

    Top Floor (3rd floor) 2 Bedroom 1 Bathroom located minutes from Winchester Center & Commuter Rail. Fully carpeted Livingroom, bedrooms hallway ,with kitchen and bathroom ceramic tile. Private deck overlooking yard. gas cooking, gas heat. Great kitchen with dishwasher, washer dryer in unit.Tenant pays gas & electric (and trash at Winchester Transfer Station. Transfer station ticket for

    19 Irving St Unit 3, 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 $1,138,443

    Last Listing Agent Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
    • 12 Prospect St, Winchester, MA 01890
      12 Prospect St, Winchester, MA 01890
      12 Prospect St, Winchester, MA 01890
      /39

      Est $3,245,755 Not Listed For Sale

      12 Prospect St, Winchester, MA 01890

      • 7 Beds
      • 5 Baths
      • 6,694 Sq Ft
      • Built 1880
      12 Prospect St, Winchester, MA 01890

      Last Sold Summary

      • 1% Above List Price
      • $478/SF
      • 9 Days On Market
      • Last Sold Price $3,199,000
      • May 09, 2025

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • 50 Brooks St, Winchester, MA 01890
    50 Brooks St, Winchester, MA 01890
    50 Brooks St, Winchester, MA 01890
    /42

    $2,595,000

    • 4 Beds
    • 3.5 Baths
    • 4,403 Sq Ft

    50 Brooks St, Winchester, MA 01890

    Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home &

    Kim Covino Compass

    50 Brooks St, Winchester, MA 01890
  • 16 Nathaniel Rd, Winchester, MA 01890
    16 Nathaniel Rd, Winchester, MA 01890
    16 Nathaniel Rd, Winchester, MA 01890
    /9

    $4,900 Per Month

    • 3 Beds
    • 1.5 Baths
    • 2,754 Sq Ft
    • House for Rent

    16 Nathaniel Rd, Winchester, MA 01890

    Available now, Spacious 3 bedroom, 1.5 bathroom single family home for rent in the heart of Winchester. This house offers a large first floor, an updated kitchen with ample cabinet space, and a private fenced backyard perfect for entertaining. The property also features a two car garage, providing additional storage and convenience. Enjoy the convenience of being just steps away from a top-rated

    Yu Li Blue Ocean Realty, LLC

    16 Nathaniel Rd, 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 $1,205,499

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    163 Main St, Winchester, MA 01890
    • 74 Hillcrest Pkwy, Winchester, MA 01890
      74 Hillcrest Pkwy, Winchester, MA 01890
      74 Hillcrest Pkwy, Winchester, MA 01890
      /20

      Est $2,515,659 Not Listed For Sale

      74 Hillcrest Pkwy, Winchester, MA 01890

      • 5 Beds
      • 4 Baths
      • 4,468 Sq Ft
      • Built 1937
      74 Hillcrest Pkwy, Winchester, MA 01890

      Last Sold Summary

      • 5% Above List Price
      • $537/SF
      • 26 Days On Market
      • Last Sold Price $2,398,000
      • May 06, 2025

      Last Listing Agent Ann Hogstadius RE/MAX Real Estate Center

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 22 days on the market compared to the national average of 58 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,558,000, down 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,558,000
Median Single Family Sale Price
$1,752,500
Median Townhouse Sale Price
$1,475,000
Median 2 Bedroom Sale Price
$935,000
Average Price Per Sq Ft
$560
Number of Homes for Sale
27
Last 12 months Home Sales
177
Months of Supply
1.80
Median List Price
$1,649,500
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-8%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group