9,215

Winchester, MA Homes

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  • /40

    $1,869,000

    • 5 Beds
    • 3.5 Baths
    • 3,294 Sq Ft

    20 Grove Place, Winchester, MA 01890

    From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a

    Andersen Group Realty Keller Williams Realty Boston Northwest

    20 Grove Place, Winchester, MA 01890
  • /7

    $1,950 per month plus fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 11, Winchester, MA 01890

    This nice 1 Bedroom 1 Bath place in the WINCHESTER area is available for 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.

    2 Elmwood Ave Unit 11, Winchester, MA 01890
  • /42

    $3,174,500 Sold Sep 02, 2025

    18 Wickham Rd, Winchester, MA 01890

    • 6 Beds
    • 5 Baths
    • 7,005 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $453/SF
    • 9 Days On Market

    Current Estimated Value $3,176,929

    Last Listing Agent Philip Vita Compass

    18 Wickham Rd, Winchester, MA 01890
    • /27

      Not Listed For Sale

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

      2 Loring Ct, Winchester, MA 01890

      2 Loring Ct, Winchester, MA 01890
  • /35

    $1,399,000 Pending

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

    6 Wyman Ct Unit 6, Winchester, MA 01890

    Another Tree Top Group masterpiece –Welcome to 6 Wyman Court! New full gut renovation townhome with 2,722 sq. ft., 3 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center

    Monte Marrocco Coldwell Banker Realty - Lexington

    6 Wyman Ct Unit 6, Winchester, MA 01890
  • /26

    $3,300 total monthly price

    • 2 Beds
    • 2.5 Baths
    • 1,486 Sq Ft
    • Apartment for Rent

    7 Conant Rd Unit 67, Winchester, MA 01890

    Beautiful 2 bed 2.5 bath townhouse with a 2 car parking at the sought-after Willows in Winchester. Condo community with use of exercise facility, outdoor pool and community center. In-unit laundry, no lead paint, Central AC, hardwood floors on main level and newer carpet on second level. Elevator building to second floor then the unit is a spacious townhouse 2nd and 3rd floors. No one above you.

    Dave Ledwig Coldwell Banker Realty - Lexington

    7 Conant Rd Unit 67, Winchester, MA 01890
  • /42

    $2,025,000 Sold Feb 21, 2025

    23 Olde Village Dr, Winchester, MA 01890

    • 3 Beds
    • 3.5 Baths
    • 4,997 Sq Ft
    • Built 1975

    Last Sold Summary

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

    Current Estimated Value $2,110,839

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    23 Olde Village Dr, Winchester, MA 01890
    • /40

      Est $1,411,226 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,350 Sq Ft

      7 Wainwright Rd Unit 29, Winchester, MA 01890

      7 Wainwright Rd Unit 29, Winchester, MA 01890
  • /42

    $1,285,000 Pending

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

    104 Church St, Winchester, MA 01890

    This charming colonial in prime flats location is full of surprises! Showcasing a stunning rear 3 story addition duplex with walls of windows & 4 rooms! Use as the primary, home office, art studio or let your children enjoy this unique space~ The first floor offers a classic layout with an expanded updated kitchen & family area open to gorgeous deck overlooking the beacon hill style yard

    Kim Covino Compass

    104 Church St, Winchester, MA 01890
  • /20

    $1,850 per month plus fees

    • Studio
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 14, Winchester, MA 01890

    This nice Studio 1 Bath place in the WINCHESTER area is available for 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

    2 Elmwood Ave Unit 14, Winchester, MA 01890
  • /28

    $1,260,000 Sold Jun 30, 2025

    261 Cambridge St Unit 261 G, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,705 Sq Ft
    • Built 1885

    Last Sold Summary

    • 3% Below List Price
    • $466/SF
    • 41 Days On Market

    Current Estimated Value $1,279,661

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

    261 Cambridge St Unit 261 G, Winchester, MA 01890
    • /25

      Est $1,055,837 Not Listed For Sale

      • 6 Beds
      • 4 Baths
      • 2,355 Sq Ft

      37-39 Middlesex St, Winchester, MA 01890

      37-39 Middlesex St, Winchester, MA 01890
  • /42

    $1,188,888

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft

    7 Trinity Rd, Winchester, MA 01890

    Welcome to 7 Trinity Road, a warm & inviting split level home tucked away on a quiet side street in sought after Winchester. From the moment you step inside, the home feels welcoming & comfortable, offering 3 bed & 2.5 baths with a layout that easily supports both everyday living & entertaining. Your foyer provides a convenient place to arrive home, with direct access to the attached garage. The

    Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
  • /16

    $3,000 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    36 Cross St Unit 1, Winchester, MA 01890

    Recently updated and bright first-floor unit featuring a spacious eat-in kitchen with new flooring, ample cabinet space, and bonus closet/pantry area. The kitchen also boasts an additional bonus room for your customization. This home offers two bedrooms, high ceilings, a renovated bathroom with a large shower, and beautiful hardwood floors. Enjoy the convenience of in-unit laundry and plenty of

    Dawn Felicani Gibson Sotheby's International Realty

    36 Cross St Unit 1, Winchester, MA 01890
  • /37

    $1,390,000 Sold Jul 15, 2025

    26 Ridge St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,388 Sq Ft
    • Built 1963

    Last Sold Summary

    • 1% Above List Price
    • $582/SF
    • 6 Days On Market

    Current Estimated Value $1,389,706

    Last Listing Agent Dream Team Dreamega International Realty LLC

    26 Ridge St, Winchester, MA 01890
    • /32

      Est $1,042,550 Not Listed For Sale

      • 1 Bed
      • 2 Baths
      • 1,275 Sq Ft

      15 Dix St Unit 9, Winchester, MA 01890

      15 Dix St Unit 9, Winchester, MA 01890
  • /42

    $3,750,000 Pending

    • 6 Beds
    • 3.5 Baths
    • 4,484 Sq Ft

    9 Lakeview Terrace, Winchester, MA 01890

    LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room!

    Kim Covino Compass

    9 Lakeview Terrace, Winchester, MA 01890
  • /32

    $4,150 total monthly price

    • 4 Beds
    • 2 Baths
    • 1,967 Sq Ft
    • Condo for Rent

    10 Webster St Unit 1, Winchester, MA 01890

    Amazing 4 bed 2 bath located within close proximity of Winchester Center! This spacious apartment takes up the first floor and lower level of a 2 family, but it has a single-family feel to it! Inside on the first floor, you'll find hardwood floors throughout, a living room, a dining room, two spacious bedrooms, and a great eat-in kitchen featuring a new dishwasher and refrigerator. Downstairs

    10 Webster St Unit 1, Winchester, MA 01890
  • /41

    $1,510,000 Sold Sep 02, 2025

    155 Highland Ave, Winchester, MA 01890

    • 5 Beds
    • 2.5 Baths
    • 1,965 Sq Ft
    • Built 1900

    Last Sold Summary

    • 13% Above List Price
    • $768/SF
    • 8 Days On Market

    Current Estimated Value $1,475,469

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

    155 Highland Ave, Winchester, MA 01890
    • /39

      Est $2,348,025 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 4,539 Sq Ft

      38 Winthrop Street Extension, Winchester, MA 01890

      38 Winthrop Street Extension, Winchester, MA 01890
  • /35

    $1,350,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,652 Sq Ft

    32 Oak St, Winchester, MA 01890

    Prime location near town center! This renovated 4-bed, 3-bath home is nestled in a private setting, walking distance to Winchester center and commuter rail to downtown Boston, nearby Middlesex Fells Reservation, High School, shops, and restaurants. Recent upgrades include new basement vinyl flooring (2025), stunning kitchen and second-floor bath renovation (2021), and new Bosch boiler and hot

    Julia Xie Keller Williams Realty-Merrimack

    32 Oak St, Winchester, MA 01890
  • /23

    $5,250 total monthly price

    • 4 Beds
    • 2 Baths
    • 2,948 Sq Ft
    • House for Rent

    113 Cambridge St, Winchester, MA 01890

    Ideally located near Winchester Center, this beautifully updated home combines modern design with classic New England charm. 113 Cambridge Street features a fully renovated kitchen with custom cabinetry, quartz counters, and premium appliances, opening to bright, inviting living spaces. The newly finished basement adds incredible versatility, ideal for a playroom, gym, or guest suite. With four

    Ryan Clunan Campion & Company Fine Homes Real Estate

    113 Cambridge St, Winchester, MA 01890
  • /39

    $2,050,000 Sold Oct 15, 2025

    64 Westland Ave, Winchester, MA 01890

    • 4 Beds
    • 5 Baths
    • 3,716 Sq Ft
    • Built 1931

    Last Sold Summary

    • $552/SF
    • 2 Days On Market

    Last Listing Agent The Murphy Group Lexington William Raveis R.E. & Home Services

    64 Westland Ave, Winchester, MA 01890
    • /34

      Est $851,175 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,584 Sq Ft

      897 Main St Unit 1, Winchester, MA 01890

      897 Main St Unit 1, Winchester, MA 01890
  • /23

    $699,000

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft

    666 Main St Unit 315, Winchester, MA 01890

    Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry, assigned parking,

    Jing Chen Peace of Mind Realty

    666 Main St Unit 315, Winchester, MA 01890
  • /14

    $3,500 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,900 Sq Ft
    • Townhouse for Rent

    112 Church St, Winchester, MA 01890

    Winchesters finest neighborhood among beautiful homes and surroundings. 2 bed townhouse with separate basement area and laundry and private porches. Lease flexible short or long term, be the first to rent this home from new buyer.2 private rooms upstairs for office (or 2 more bedrooms). Available now.

    112 Church St, Winchester, MA 01890
  • /25

    $715,000 Sold Jun 27, 2025

    7 Conant Rd Unit 37, Winchester, MA 01890

    • 2 Beds
    • 2.5 Baths
    • 1,539 Sq Ft
    • Built 1999

    Last Sold Summary

    • 5% Below List Price
    • $465/SF
    • 33 Days On Market

    Current Estimated Value $720,406

    Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Conant Rd Unit 37, Winchester, MA 01890
    • /33

      Est $1,703,941 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,254 Sq Ft

      20 Graystone Cir Unit 20, Winchester, MA 01890

      20 Graystone Cir Unit 20, Winchester, MA 01890
  • /31

    $1,999,000 Pending

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

    46 Church St, Winchester, MA 01890

    Welcome to 46 Church Street. This spacious, beautifully maintained, Paul Whitney built home is just outside the heart of Winchester center with easy access to the commuter rail, schools, restaurants, and shopping. Offering flexible living areas and abundant room throughout, the residence features four bedrooms, three and a half bathrooms, two dedicated home offices, and a generously sized bonus

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

    46 Church St, Winchester, MA 01890
  • /16

    $3,400 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Apartment for Rent

    317 Cross St Unit 319, Winchester, MA 01890

    Townhouse available 12/1! This Townhouse offers spacious 3 bedrooms, living room, kitchen and 1 full bath. There have been many updates with hardwood flooring through out, new kitchen floor, and painting in all rooms. Basement has Washer and Dryer Hook ups and 2 parking spots. There is a backyard and deck coming off kitchen. Tenant is to shovel driveway and walkway in winter months. There is a

    Robin Griffiths J. Mulkerin Realty

    317 Cross St Unit 319, Winchester, MA 01890
  • /19

    $690,000 Sold Jun 06, 2025

    7 Conant Rd Unit 60, Winchester, MA 01890

    • 2 Beds
    • 2.5 Baths
    • 1,634 Sq Ft
    • Built 1999

    Last Sold Summary

    • 6% Below List Price
    • $422/SF
    • 20 Days On Market

    Current Estimated Value $737,071

    Last Listing Agent Irene Novia Loka Matahari Real Estate LLC

    7 Conant Rd Unit 60, Winchester, MA 01890
    • /42

      Est $2,867,891 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 6,265 Sq Ft

      228 Ridge St, Winchester, MA 01890

      228 Ridge St, Winchester, MA 01890
  • /11

    $299,000 Pending

    • 1 Bed
    • 1 Bath
    • 394 Sq Ft

    200 Swanton St Unit 636, Winchester, MA 01890

    Immaculate, studio condominium within the desirable Parkview Condominiums in Winchester. The large private balcony overlooks a beautiful wildlife pond, and the grounds are meticulously landscaped. The kitchen features tile flooring, updated granite countertops, and a breakfast bar. The Condominium amenities include: in-ground swimming pool, barbecue area, large parking area with plenty of

    Michael Masci North Atlantic Realty Group

    200 Swanton St Unit 636, Winchester, MA 01890
  • /19

    $2,700 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Condo for Rent

    145 Washington St Unit 415, Winchester, MA 01890

    At 1300sqft, this unit far exceeds the average size for a 2 bed 1 bath. Priced competitively. Very close to 93 yet neatly tucked away, you'll have two side by side parking spaces on the side street (off the main road). Screened in backdoor area so you can be as close to comfort as possible. Once entering the space you'll be greeted by large bedrooms, a cozy kitchen and your choice of an

    145 Washington St Unit 415, Winchester, MA 01890
  • /38

    $1,525,000 Sold Sep 12, 2025

    5 Thornton Rd, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,755 Sq Ft
    • Built 1929

    Last Sold Summary

    • 12% Below List Price
    • $554/SF
    • 30 Days On Market

    Current Estimated Value $1,564,810

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

    5 Thornton Rd, Winchester, MA 01890
    • /40

      Est $1,378,886 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,529 Sq Ft

      15 Wincrest Dr, Winchester, MA 01890

      15 Wincrest Dr, Winchester, MA 01890
  • /38

    $1,650,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,882 Sq Ft

    82 Hillcrest Pkwy, Winchester, MA 01890

    Nestled directly across from the breathtaking Middlesex Fells Reservation, this home offers the perfect blend of charm, space, and potential. This classic 3-bedroom, 2.5 bath Cape is beautifully situated on over half an acre in one of Winchester’s most desirable locations. The home features mostly hardwood floors throughout, a brand-new roof, and a newer heating and AC system. The second floor

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

    82 Hillcrest Pkwy, Winchester, MA 01890
  • /27

    $3,300 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,338 Sq Ft
    • Condo for Rent

    7 Conant Rd Unit 21, Winchester, MA 01890

    Welcome to 7 Conant Road! This unit offers a spacious open floor plan with 1,338 square feet, featuring two bedrooms and two full bathrooms, including a roomy primary suite. Enjoy open concept living with nice flow from the kitchen to the living room & dining area. Updated & move-in ready, the bedrooms are large, complete with generous closet space. This rental showcases modern charm with an

    Kim Covino Compass

    7 Conant Rd Unit 21, Winchester, MA 01890
  • /42

    $1,540,000 Sold Jul 11, 2025

    21 Johnson Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,814 Sq Ft
    • Built 1970

    Last Sold Summary

    • 1% Above List Price
    • $547/SF
    • 5 Days On Market

    Current Estimated Value $1,534,250

    Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

    21 Johnson Rd, Winchester, MA 01890
    • /33

      Est $1,512,453 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,034 Sq Ft

      10 Carriage Ln, Winchester, MA 01890

      10 Carriage Ln, Winchester, MA 01890

Showing Results 41 - 80, Page 2 of 18

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