9,202

Winchester, MA Homes

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    • /36

      Est $1,445,977 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,019 Sq Ft

      99 Loring Ave, Winchester, MA 01890

      99 Loring Ave, Winchester, MA 01890
  • /32

    $1,262,000 Sold Jul 24, 2024

    • 1,965 Sq Ft
    • $642/SF
    • 56 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1879

    79 Oak St, Winchester, MA 01890

    Opportunity knocks in Winchester to own a beautifully maintained South facing home on a Sun-drenched corner lot! Gorgeous landscaping surrounds the large front yard and private fenced in backyard, an oasis for entertainment! Features include a 2-car garage with additional off-street driveway parking and irrigation system. The 1st level offers an updated kitchen/dining room with radiant floor

    Michelle Doyle Flow Realty, Inc.

    79 Oak St, Winchester, MA 01890
    • /42

      Est $1,095,926 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,913 Sq Ft

      5 Highland View Ave, Winchester, MA 01890

      5 Highland View Ave, Winchester, MA 01890
  • /28

    $715,000 Sold Jul 18, 2024

    • 1,160 Sq Ft
    • $616/SF
    • 7 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2000

    7 Conant Rd Unit 27, Winchester, MA 01890

    Step into luxury living with this meticulously renovated single-level condo. No detail has been overlooked in this exquisite residence. Hardwood floors that flow seamlessly throughout the open concept floor plan, creating a warm and inviting ambiance. Brand new tiled bathrooms, featuring new fixtures, stylish vanities, and pristine finishes. Entertain with ease in the spacious living area

    Alyssa Vozzella Cameron Real Estate Group

    7 Conant Rd Unit 27, Winchester, MA 01890
    • /29

      Est $760,636 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 828 Sq Ft

      241 Cross St, Winchester, MA 01890

      241 Cross St, Winchester, MA 01890
  • /42

    $2,375,000 Sold Jul 17, 2024

    • 4,091 Sq Ft
    • $581/SF
    • 4 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1865

    7 Stevens St, Winchester, MA 01890

    Circa 1865, this spectacular Mansard roof Victorian home blends timeless elegance with modern amenities and charm. Exquisite period detail and appeal abound with leaded and stained glass windows and grand staircase all lovingly maintained. In town location is perfect for shopping and transportation. The private estate-like setting has magnificent gardens, large private yard, bluestone dining

    Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

    7 Stevens St, Winchester, MA 01890
    • /17

      Est $1,161,559 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,016 Sq Ft

      269 Cross St Unit 271, Winchester, MA 01890

      269 Cross St Unit 271, Winchester, MA 01890
  • /42

    $1,792,900 Sold Jul 16, 2024

    • 3,175 Sq Ft
    • $565/SF
    • 4 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1931

    18 Stone Ave, Winchester, MA 01890

    Cherished home located on a quiet side street in Winchester Highlands, close to the popular Fells Reservation. Flexible layout perfect for today's living with 5 beds & 3.5 baths. The 1st floor features a formal living room with fireplace, expansive family room & open concept dining room/kitchen with new appliances, cherry cabinets and beverage cooler. Two 1st floor bedrooms and a full bath

    Paul Cirignano The Synergy Group

    18 Stone Ave, Winchester, MA 01890
    • /9

      Est $1,771,071 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,415 Sq Ft

      118 Wendell St, Winchester, MA 01890

      118 Wendell St, Winchester, MA 01890
  • /41

    $2,330,000 Sold Jul 15, 2024

    • 3,676 Sq Ft
    • $634/SF
    • 5 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1942

    79 Yale St, Winchester, MA 01890

    One of the most coveted, vibrant locations in town, the part of the Flats that everyone wants! This Colonial offers the space and layout to meet today's lifestyle demands while retaining beautiful architectural character and grace. The first floor offers a spacious kitchen with a center island and plenty of cabinet space. It opens onto a huge family room highlighted by vaulted ceilings, a

    Nancy Pallotta Advisors Living - Winchester

    79 Yale St, Winchester, MA 01890
    • /39

      Est $990,547 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,323 Sq Ft

      108 Wendell St, Winchester, MA 01890

      108 Wendell St, Winchester, MA 01890
  • /40

    $2,125,000 Sold Jul 15, 2024

    • 3,344 Sq Ft
    • $635/SF
    • 4 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1967

    3 Berkshire Dr, Winchester, MA 01890

    Beautifully situated on a corner lot (Nearly 1/2 an Acre!!) this West Side Gem on Lexington line is the one you've been waiting for. Quintessential New England Colonial has been updated throughout + is move-in ready. First floor offers generous / flexible living areas - private family room and a front facing formal parlor. Gorgeous Chef’s kitchen is ideal for entertaining and boasts custom

    Allison Shannon Berkshire Hathaway HomeServices Commonwealth Real Estate

    3 Berkshire Dr, Winchester, MA 01890
    • /35

      Est $1,374,197 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,910 Sq Ft

      14 Hill St, Winchester, MA 01890

      14 Hill St, Winchester, MA 01890
  • /42

    $1,960,000 Sold Jul 15, 2024

    • 5,800 Sq Ft
    • $338/SF
    • 24 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2016

    8 Johnson Rd, Winchester, MA 01890

    Nestled in Winchester's esteemed WEST SIDE, this Colonial gem epitomizes modern luxury. This includes an iPad-operated control system for sound, heat, alarm, and property security camera! Spanning 4 floors, the main level invites with a grand living and family room adorned with a gas fireplace and soaring ceilings. Culinary delights await in the oversized kitchen boasting granite counters, SS

    Monte Marrocco Coldwell Banker Realty - Lexington

    8 Johnson Rd, Winchester, MA 01890
    • /42

      Est $1,377,517 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,365 Sq Ft

      18 Forest St, Winchester, MA 01890

      18 Forest St, Winchester, MA 01890
  • /41

    $1,850,000 Sold Jul 15, 2024

    • 4,274 Sq Ft
    • $433/SF
    • 36 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1916

    204 Highland Ave, Winchester, MA 01890

    Imagine living at the foot of the Fells, surrounded by a natural setting while being close to the Muraco School, trains, and the town center. This gorgeous Colonial sits high on a hill, surrounded by custom rock walls, a stone patio, and mature landscaping. With 5 bedrooms, including a first-floor guest suite, there’s room for everyone and options for live-in nannies, in-laws, or aging in place.

    Nancy Pallotta Advisors Living - Winchester

    204 Highland Ave, Winchester, MA 01890
    • /42

      Est $1,415,317 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,381 Sq Ft

      24 Brookside Ave, Winchester, MA 01890

      24 Brookside Ave, Winchester, MA 01890
  • /33

    $1,160,000 Sold Jul 12, 2024

    • 2,490 Sq Ft
    • $466/SF
    • 2 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1927

    17 Cross St, Winchester, MA 01890

    Don’t miss this meticulously maintained, beautifully renovated home~ move right in & enjoy! This great home is situated on an adorable lot with patio, perfectly sized yard & garage. High ceilings throughout w/ a large sun drenched living room which flows seamlessly into the dining room, featuring sliding glass doors opening to a charming 3-season sunroom. The large eat-in kitchen offers cherry

    Kim Covino Compass

    17 Cross St, Winchester, MA 01890
    • /29

      Est $1,037,533 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,380 Sq Ft

      88 Forest St, Winchester, MA 01890

      88 Forest St, Winchester, MA 01890
  • /42

    $1,425,000 Sold Jul 11, 2024

    • 2,534 Sq Ft
    • $562/SF
    • 10 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1933

    124 Forest St, Winchester, MA 01890

    Welcome to this charming renovated home on a lush oversized lot in a super convenient location near Muraco School. This updated 3-bedroom, 2.5-bathroom home w/ A/C offers a perfect blend of modern finishes & original old world detail. Inside you'll find a beautifully renovated, open concept kitchen with stainless steel appliances, quartz counters, pantry & plenty of prep space open to a dining

    Kim Covino Compass

    124 Forest St, Winchester, MA 01890
    • /42

      Est $1,458,849 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,347 Sq Ft

      15 Garfield Ave, Winchester, MA 01890

      15 Garfield Ave, Winchester, MA 01890
  • /42

    $2,070,000 Sold Jul 11, 2024

    • 7,292 Sq Ft
    • $284/SF
    • 39 Days On Market
    • 5 Beds
    • 7 Baths
    • Built 1974

    7 Russett Ln, Winchester, MA 01890

    Your chance to be the 2nd proud owner of this meticulously maintained home in the heart of Winchester, where luxury living meets timeless elegance. This magnificent property offers unparalleled comfort & sophistication, boasting 5 bedrooms, 5 full & 2 half bathrooms across its sprawling 6,700+ floor plan. As you step in, you are greeted by a beautiful bridal staircase and marble flooring. The 3

    Reliable Results Realty Coldwell Banker Realty - Westford

    7 Russett Ln, Winchester, MA 01890
    • /36

      Est $963,494 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,288 Sq Ft

      27 Garfield Ave, Winchester, MA 01890

      27 Garfield Ave, Winchester, MA 01890
  • /42

    $1,900,000 Sold Jul 10, 2024

    • 2,816 Sq Ft
    • $675/SF
    • 6 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1934

    26 Stowell Rd, Winchester, MA 01890

    Nestled in an idyllic neighborhood, this stunning property underwent complete renovation/addition in 2016, ensuring modern comfort & space. As you step through the entry, you're greeted by an abundance of natural light & a sense of airiness that permeates every corner of the home. The open-concept layout seamlessly connects the living, dining, & kitchen, creating an ideal space for both family

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    26 Stowell Rd, Winchester, MA 01890
    • /41

      Est $1,212,479 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,696 Sq Ft

      28 Garfield Ave, Winchester, MA 01890

      28 Garfield Ave, Winchester, MA 01890
  • /30

    $1,148,000 Sold Jul 10, 2024

    • 2,240 Sq Ft
    • $512/SF
    • 25 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1966

    350 S Border Rd, Winchester, MA 01890

    This stunning 3-bedroom/2.5-bath home blends indoor comfort and outdoor charm. The main floor is an open concept design with cathedral ceilings and a striking floor-to-ceiling fireplace. Large windows offer abundant light and impressive views of nature’s beauty. The kitchen has stainless-steel appliances and a large island with extra storage and seating, the ideal spot for gatherings. Sunset

    Jill Fitzpatrick Century 21 North East

    350 S Border Rd, Winchester, MA 01890
    • /41

      Est $1,278,528 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,302 Sq Ft

      39 Forest St, Winchester, MA 01890

      39 Forest St, Winchester, MA 01890
  • /31

    $755,000 Sold Jul 05, 2024

    • 1,523 Sq Ft
    • $496/SF
    • 17 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2004

    400 Cross St Unit 401, Winchester, MA 01890

    Experience unparalleled charm in the CORNER and BIGGEST unit at Winchester Crossing. Step into an inviting atmosphere with an open-concept living area, adorned with abundant natural light. Relax in the expansive living room, complete with a cozy fireplace and direct access to a private balcony, ideal for enjoying serene evenings. The kitchen features a breakfast nook, which always offers a

    Montivista Real Estate Group eXp Realty

    400 Cross St Unit 401, Winchester, MA 01890
    • /41

      Est $1,198,224 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,281 Sq Ft

      502 Washington St, Winchester, MA 01890

      502 Washington St, Winchester, MA 01890
  • /39

    $1,387,500 Sold Jul 03, 2024

    • 3,206 Sq Ft
    • $433/SF
    • 5 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1925

    20 Bacon St Unit A, Winchester, MA 01890

    Beautifully maintained & filled w/character & charm! This beautifully renovated home offers high ceilings, stunning updated kitchen flooded w/sunlight, quartz countertops, built ins & cozy dining nook w/ access to spacious private deck overlooking the yard. A Large bow front dining room w/ hardwood floors china cabinet & fire-placed living room create the perfect setting for family &

    Kim Covino Compass

    20 Bacon St Unit A, Winchester, MA 01890
    • /35

      Est $975,108 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,726 Sq Ft

      21 Holton St, Winchester, MA 01890

      21 Holton St, Winchester, MA 01890
  • /26

    $1,160,000 Sold Jul 02, 2024

    • 2,700 Sq Ft
    • $430/SF
    • 4 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1986

    51-53 Charles Rd, Winchester, MA 01890

    Rare opportunity in Winchester to buy a large two-family at a great price! This property offers the ideal blend of investment potential & comfortable living. Each unit features 3 bds,1.5 br & extra-large, separated level lot, providing a perfect setup for rental income or multi-gen living. Top-tier schools & public transportation. This is a must see and won't last! Showings limited to open houses

    Kim Covino Compass

    51-53 Charles Rd, Winchester, MA 01890
    • /42

      Est $2,171,879 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,350 Sq Ft

      7 Nathaniel Rd, Winchester, MA 01890

      7 Nathaniel Rd, Winchester, MA 01890
  • /29

    $1,365,000 Sold Jul 02, 2024

    • 2,769 Sq Ft
    • $493/SF
    • 41 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1925

    50 Allen Rd, Winchester, MA 01890

    Top East side neighborhood! Don't miss this renovated & expanded 3BR home offering a great layout, flooded w/natural light. Spacious Living room w/wood burning fireplace, adjacent sun room, office/play room plus a stunning eat in kitchen w/ ample storage, prep space, large island & dining area w/ vaulted ceilings & picture window overlooking the well manicured yard. The main floor also includes a

    Kim Covino Compass

    50 Allen Rd, Winchester, MA 01890
    • /38

      Est $1,379,476 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,799 Sq Ft

      39 Nathaniel Rd, Winchester, MA 01890

      39 Nathaniel Rd, Winchester, MA 01890
  • /41

    $2,125,000 Sold Jul 01, 2024

    • 3,938 Sq Ft
    • $540/SF
    • 43 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2021

    19 Gershon Way Unit 19, Winchester, MA 01890

    This home evokes a fresh, breezy, coastal vibe-making everyday feel like vacation. Located on the MOST PRIVATE homesite within this Award Winning 55+ Community. It is a modern, entertainer's dream house which boasts an open concept plan, TOP OF THE LINE CHEF'S KITCHEN + a buffet & bev. center in the adjacent dining room - which is "topped off" by a masterfully built coffered ceiling. All rooms

    Michelle Faust Coldwell Banker Realty - Westwood

    19 Gershon Way Unit 19, Winchester, MA 01890
    • /38

      Est $1,245,574 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,681 Sq Ft

      32 Nathaniel Rd, Winchester, MA 01890

      32 Nathaniel Rd, Winchester, MA 01890
  • /41

    $1,649,500 Sold Jun 28, 2024

    • 3,011 Sq Ft
    • $548/SF
    • 17 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1950

    67 Wildwood St, Winchester, MA 01890

    Yes you can have it all. Winchester Flats, corner of Yale Street location. Exquisite move in ready gracious home, that will truly impress. Excellent layout, with a first floor bedroom and bath, walk in shower and double sink vanity. Spacious and sunny living room with a fireplace, dining room, and a first floor office. Family Room off the updated, eat-in Kitchen with sliders to the Patio and

    Dorothea Feffer Coldwell Banker Realty - Lexington

    67 Wildwood St, Winchester, MA 01890
    • /42

      Est $2,216,000 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,634 Sq Ft

      15 Tufts Rd, Winchester, MA 01890

      15 Tufts Rd, Winchester, MA 01890
  • /40

    $1,175,000 Sold Jun 27, 2024

    • 2,430 Sq Ft
    • $484/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1977

    134 Johnson Rd, Winchester, MA 01890

    Extraordinary opportunity to own this updated 4 bedroom, 2.5 bath Colonial abutting the 120 acre Whipple Hill Conservation Area. This home boasts a wonderful-for-entertaining first floor layout, including a spacious living room, dining room with wainscoting, eat-in kitchen, 1/2 bath and family room with beautiful wide-board flooring and fireplace. Access the deck off of the family room. The

    Steve Savarese Senne

    134 Johnson Rd, Winchester, MA 01890

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