9,206

Winchester, MA Homes

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  • /42

    $3,450,000

    Open Sat 12:30PM - 2PM
    • 6 Beds
    • 4.5 Baths
    • 5,735 Sq Ft

    7 Hutchinson Rd, Winchester, MA 01890

    Situated on a generous18,000SF level lot! Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the

    Kim Covino Compass

    7 Hutchinson Rd, Winchester, MA 01890
  • /17

    $3,200 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,460 Sq Ft
    • Condo for Rent

    60 Lake St Unit D, Winchester, MA 01890

    LOCATION! LOCATION! LOCATION! Here is your opportunity to live in a quiet and beautifully renovated townhouse in the heart of Winchester, MA. Walking distance to all local schools, parks, downtown shops and restaurants, the commuter rail, tennis courts, and right next to Wedge Pond; where you can enjoy year round fun whether it’s swimming in the summer, or ice skating in the winter. The first

    Clara Wu United Real Estate, LLC

    60 Lake St Unit D, Winchester, MA 01890
  • /39

    $3,100,000

    Sold Jul 15, 2026

    27 Everett Ave, Winchester, MA 01890

    • 6 Beds
    • 5.5 Baths
    • 7,431 Sq Ft
    • Built 1905

    Last Sold Summary

    • 14% Below List Price
    • $417/SF
    • 118 Days On Market

    Current Estimated Value $3,249,259

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    27 Everett Ave, Winchester, MA 01890
    • /42

      Est $1,560,744

      Not Listed For Sale

      21 Johnson Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,814 Sq Ft
      • Built 1970
      21 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

  • /37

    $950,000

    Open Sun 11AM - 12:30PM $150K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,365 Sq Ft

    83 Church St Unit 15, Winchester, MA 01890

    Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal

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

    83 Church St Unit 15, Winchester, MA 01890
  • /16

    $3,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft
    • Condo for Rent

    666 Main St Unit 208, Winchester, MA 01890

    Freshly painted and move in ready, 2 bed, 2 bath unit is located in the highly desirable Wedgewood Place. This unit boasts an open concept kitchen, dining and living room complete with a fireplace and alcove perfect for a home office. . The primary suite offers walk in closet closet space and private bath with tub and shower. Second bedroom, additional full bath and washer and dryer complete this

    Pirani & Wile Group Gibson Sotheby's International Realty

    666 Main St Unit 208, Winchester, MA 01890
  • /42

    $2,350,000

    Sold Aug 12, 2026

    50 Brooks St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 4,403 Sq Ft
    • Built 1988

    Last Sold Summary

    • 9% Below List Price
    • $534/SF
    • 67 Days On Market

    Current Estimated Value $2,402,198

    Last Listing Agent Kim Covino Compass

    50 Brooks St, Winchester, MA 01890
    • /36

      Est $2,303,255

      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

      • 195 Days On Market

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

  • /41

    $700,000

    Open Sat 10AM - 12PM
    • 2 Beds
    • 2 Baths
    • 1,240 Sq Ft

    666 Main St Unit 217, Winchester, MA 01890

    Easy one-floor living in Winchester Center with garage parking for one car! Fabulous location near town center, TRAIN, shopping, restaurants, schools and library. Enjoy the open layout with extra wall of beautiful kitchen cabinets, large peninsula/eating bar, fireplace, balcony and a nook for a desk or whatever you wish. Large primary bedroom has two windows, large walk-in closet and full bath.

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    666 Main St Unit 217, Winchester, MA 01890
  • /19

    $3,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Condo for Rent

    7 Conant Rd Unit 19, Winchester, MA 01890

    Available NOW! Welcome to your oasis at The Willows at Winchester. This fully gut-renovated, first-floor corner unit offers seamless single-level living at its finest. The Living Space offers open-concept layout featuring rich hardwoods, a gourmet chef's kitchen, dining area and living room w/ a cozy gas fireplace opening to your private patio. The Bedrooms: A lavish primary suite with a walk-in

    Ides Figueiredo Coldwell Banker Realty - Brookline

    7 Conant Rd Unit 19, 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 $952,457

    Last Listing Agent Andrea Mackey The Agency Boston

    16 Park Ave Unit 1, Winchester, MA 01890
    • /42

      Est $2,434,116

      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

      • 5 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /26

    $349,900

    • 1 Bed
    • 1 Bath
    • 602 Sq Ft

    200 Swanton St Unit T14, Winchester, MA 01890

    An exceptional opportunity to own in Winchester at an accessible price point! This first-floor, one-bedroom Terrace level at The Parkview offers an unbeatable combination of convenience, affordability, and practical living. Positioned on the ground level for easy direct access, the unit features peaceful views of the scenic duck ponds and mature, green landscaping. Step inside to an efficient

    Paul Cirignano The Synergy Group

    200 Swanton St Unit T14, Winchester, MA 01890
  • /18

    $3,895 Per Month

    • 2 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Apartment for Rent

    77 Church St Unit A, Winchester, MA 01890

    Beautiful condo style apartment for rent on picturesque Church Street. A lovely 2nd floor unit, generously sized with hardwood floors throughout. Walk upstairs to an open vestibule perfect for reading a good book with direct access to the covered front porch. Living room with faux fireplace opens to a bright and airy home office or a classic dining room with period built-in cabinet. Oversized

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

    77 Church St Unit A, Winchester, MA 01890
  • /38

    $2,600,000

    Sold Jun 18, 2026

    15 York Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Above List Price
    • $578/SF
    • 7 Days On Market

    Current Estimated Value $2,501,265

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

    15 York Rd, Winchester, MA 01890
    • /42

      Est $1,846,914

      Not Listed For Sale

      19 Pilgrim Dr, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 3,150 Sq Ft
      • Built 1961
      19 Pilgrim Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Gorfinkle Group eXp Realty LLC - Corporate Office

  • /42

    $685,000

    Open Sat 10AM - 12PM $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    666 Main St Unit 211, Winchester, MA 01890

    NEW PRICE! Great layout and numerous recent improvements make this a wonderful opportunity! Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    666 Main St Unit 211, Winchester, MA 01890
  • /21

    $2,700 Per Month

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

    115 Washington St Unit 1B, Winchester, MA 01890

    Best rental on the market in Winchester! This Beautifully updated one bedroom and one bathroom condo is avaiable for rent. The enter island kitchen opens up to a bright living and dining room area. This home boasts of all new kitchen appliances, heat pump (heat and AC), efinished hardwood floors, & recessed dimmable lighting. California closets in both closets in the bedroom, laundry room with

    Leah Pennini Gamut Group LLC

    115 Washington St Unit 1B, Winchester, MA 01890
  • /35

    $2,575,000

    Sold May 14, 2026

    2 Abby Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 5,614 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Below List Price
    • $459/SF
    • 12 Days On Market

    Current Estimated Value $2,591,245

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    2 Abby Rd, Winchester, MA 01890
    • /40

      Est $1,434,908

      Not Listed For Sale

      16 Johnson Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 3,142 Sq Ft
      • Built 1958
      16 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • /21

    $774,900

    $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    50 Middlesex St Unit 52, Winchester, MA 01890

    Completely renovated from top to bottom, this brand-new 2-bedroom, 2-bath condo offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy white oak hardwood floors, a stunning chef's kitchen

    The North Star Group Keller Williams Realty Evolution

    50 Middlesex St Unit 52, Winchester, MA 01890
  • /38

    $6,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,443 Sq Ft
    • House for Rent

    25 Berkshire Dr, Winchester, MA 01890

    This beautifully renovated home offers over 2,400 sq ft of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today's lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high end Spanish panels, dovetail

    Nadia Mounsif McCaul & Mounsif Real Estate Group LLC

    25 Berkshire Dr, Winchester, MA 01890
  • /42

    $2,650,000

    Sold Apr 21, 2026

    45 Bacon St, Winchester, MA 01890

    • 7 Beds
    • 8 Baths
    • 7,043 Sq Ft
    • Built 2011

    Last Sold Summary

    • 11% Below List Price
    • $376/SF
    • 29 Days On Market

    Current Estimated Value $2,814,090

    Last Listing Agent Kim Covino Compass

    45 Bacon St, Winchester, MA 01890
    • /42

      Est $1,912,567

      Not Listed For Sale

      19 Johnson Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 4,318 Sq Ft
      • Built 1956
      19 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Philip Vita Compass

  • /27

    $829,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    666 Main St Unit 207, Winchester, MA 01890

    Sunlit, pristine and perfectly located in the center of town ! This second floor unit features a fully renovated white kitchen (2019) with new appliances, seamlessly flowing into an open, inviting living space. Step directly out onto your private roof deck overlooking tranquil views of Wedge Pond...the ultimate spot for morning coffee or evening relaxing. The two bedroom, two bath unit also

    Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

    666 Main St Unit 207, Winchester, MA 01890
  • /28

    $3,100 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    7 Ridge St, Winchester, MA 01890

    Welcome to this charming 2-bedroom, 1.5-bath rental located on the desirable west side of Winchester. Offering three levels of living space, this home provides plenty of room to spread out and enjoy a comfortable, flexible layout. Beautiful hardwood floors add warmth and character throughout, while the level, partially fenced backyard provides a wonderful private outdoor space for relaxing,

    Shannon Jenkins RE/MAX Realty Experts

    7 Ridge St, Winchester, MA 01890
  • /42

    $1,700,000

    Sold May 01, 2026

    114 Johnson Rd, Winchester, MA 01890

    • 3 Beds
    • 3 Baths
    • 3,182 Sq Ft
    • Built 1880

    Last Sold Summary

    • 5% Below List Price
    • $534/SF
    • 22 Days On Market

    Current Estimated Value $1,696,035

    Last Listing Agent Rosemary Kelleher LAER Realty Partners

    114 Johnson Rd, Winchester, MA 01890
    • /33

      Est $1,359,793

      Not Listed For Sale

      3 Socrates Way, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,570 Sq Ft
      • Built 1966
      3 Socrates Way, Winchester, MA 01890

      Last Sold Summary

      • 9 Days On Market

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

  • /42

    $3,149,000

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

    37 Mayflower Rd, Winchester, MA 01890

    Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by

    Kim Covino Compass

    37 Mayflower Rd, Winchester, MA 01890
  • /42

    $1,830,000

    Sold Feb 26, 2026

    35 Glen Green, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 3,509 Sq Ft
    • Built 1934

    Last Sold Summary

    • 8% Below List Price
    • $522/SF
    • 36 Days On Market

    Current Estimated Value $1,883,181

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    35 Glen Green, Winchester, MA 01890
    • /39

      Est $2,007,321

      Not Listed For Sale

      1 Saint Augustine Ct, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 3,818 Sq Ft
      • Built 1967
      1 Saint Augustine Ct, Winchester, MA 01890

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • /30

    $899,000

    Open Sun 12:30PM - 2PM $51K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 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
  • /42

    $1,800,000

    Sold Aug 17, 2026

    18 Graystone Cir Unit 18, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,833 Sq Ft
    • Built 2012

    Last Sold Summary

    • 3% Above List Price
    • $635/SF
    • 1 Day On Market

    Last Listing Agent Kim Covino Compass

    18 Graystone Cir Unit 18, Winchester, MA 01890
    • /42

      Est $2,418,415

      Not Listed For Sale

      12 Olde Lyme Rd, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,215 Sq Ft
      • Built 1955
      12 Olde Lyme Rd, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Mary Beth McGillicuddy Engel & Völkers , South Shore

  • /42

    $1,495,000

    • 4 Beds
    • 2.5 Baths
    • 2,973 Sq Ft

    7 Sherman Place, Winchester, MA 01890

    Move-in-ready luxury townhouse in Winchester with the space, privacy, and single-family-home feel rarely found in condominium living. Built in 2005 and thoughtfully updated, 7 Sherman Place is set on a cul-de-sac and offers 3,095 square feet across four finished levels with four bedrooms, two-and-a-half baths, a private one-car garage, and outstanding indoor and outdoor living spaces.The bright,

    John Dean Engel & Volkers Boston

    7 Sherman Place, Winchester, MA 01890
  • /42

    $1,330,000

    Sold Apr 14, 2026

    40 Pickering St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,454 Sq Ft
    • Built 1870

    Last Sold Summary

    • 6% Above List Price
    • $542/SF
    • 0 Days On Market

    Current Estimated Value $1,300,556

    Last Listing Agent Timothy Haynes Keller Williams Realty Signature Properties

    40 Pickering St, Winchester, MA 01890
    • /33

      Est $1,944,465

      Not Listed For Sale

      8 Olde Lyme Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 4,603 Sq Ft
      • Built 1960
      8 Olde Lyme Rd, Winchester, MA 01890

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • /42

    $1,679,900

    Pending
    • 3 Beds
    • 2 Baths
    • 2,483 Sq Ft

    5 Willowdale Rd, Winchester, MA 01890

    Distinctive in both design and craftsmanship, this custom expanded Ranch combines balanced architectural proportions, generous living space, and everyday comfort in Winchester’s highly sought-after East Hill neighborhood. A welcoming foyer with built-in bench opens to warm, light-filled interiors curated to feel both connected and intimate. At the heart of the home, the expansive mahogany kitchen

    Erica Carson Coldwell Banker Realty - Lexington

    5 Willowdale Rd, Winchester, MA 01890
  • /30

    $900,000

    Sold Oct 20, 2025

    171 Swanton St Unit 5, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,843 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $488/SF
    • 8 Days On Market

    Current Estimated Value $923,879

    Last Listing Agent Jonathan Radford Coldwell Banker Realty - Boston

    171 Swanton St Unit 5, Winchester, MA 01890
    • /25

      Est $1,846,007

      Not Listed For Sale

      4 Olde Lyme Rd, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 3,488 Sq Ft
      • Built 1980
      4 Olde Lyme Rd, Winchester, MA 01890

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

Showing Results 121 - 160, Page 4 of 18

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