9,206

Winchester, MA Homes

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  • /30

    $2,799,000

    $51K PRICE DROP Pending
    • 6 Beds
    • 7 Baths
    • 6,968 Sq Ft

    14 Nassau Dr, Winchester, MA 01890

    Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

    Weidong Li WINN Real Estate & Consulting

    14 Nassau Dr, Winchester, MA 01890
  • /41

    $11,500 Per Month

    • 5 Beds
    • 3 Baths
    • 4,132 Sq Ft
    • House for Rent

    10 Bellevue Ave, Winchester, MA 01890

    Beautiful newer construction 4/5 bedroom *furnished or *unfurnished home with an attached garage, ideally situated on a gorgeous 11,000+ sq. ft. lot in a wonderful neighborhood with easy access to Route 93 and Boston. This spacious and inviting home offers a flexible floor plan, including a first-floor bedroom with a full bath, perfect for guests, a home office, or additional living space. The

    Kim Covino Compass

    10 Bellevue Ave, Winchester, MA 01890
  • /40

    $3,150,000

    Sold May 28, 2026

    257 High St, Winchester, MA 01890

    • 5 Beds
    • 7 Baths
    • 7,101 Sq Ft
    • Built 1994

    Last Sold Summary

    • 3% Below List Price
    • $444/SF
    • 2 Days On Market

    Current Estimated Value $3,118,023

    Last Listing Agent Kim Covino Compass

    257 High St, Winchester, MA 01890
    • /11

      Est $1,301,828

      Not Listed For Sale

      233 High St, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 2,218 Sq Ft
      • Built 1952
      233 High St, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /38

    $1,125,000

    Pending
    • 5 Beds
    • 2.5 Baths
    • 2,391 Sq Ft

    8-10 Oak St, Winchester, MA 01890

    Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz

    Paul Cirignano The Synergy Group

    8-10 Oak St, Winchester, MA 01890
  • /16

    $3,200 Per Month

    • 3 Beds
    • 1.5 Baths
    • Apartment for Rent

    5 Quigley Ct Unit 5, Winchester, MA 01890

    Great opportunity to rent this spacious 3-bedroom duplex offering three levels of living space, tucked away on a quiet dead-end street. Freshly painted throughout, the unit features new flooring, an updated kitchen equipped with a stove, dishwasher, and refrigerator, three generously sized bedrooms, and 1.5 bathrooms. The basement offers additional storage space, with a washer and dryer available

    Anna Mean AC Realty

    5 Quigley Ct Unit 5, Winchester, MA 01890
  • /42

    $1,730,000

    Sold Jul 24, 2026

    307 Cross St, Winchester, MA 01890

    • 5 Beds
    • 5 Baths
    • 3,500 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $494/SF
    • 6 Days On Market

    Current Estimated Value $1,678,133

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

    307 Cross St, Winchester, MA 01890
    • /40

      Est $1,340,210

      Not Listed For Sale

      134 Johnson Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,430 Sq Ft
      • Built 1977
      134 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Steve Savarese Senne

  • /39

    $799,000

    $101K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,083 Sq Ft

    84 Oak St, Winchester, MA 01890

    $5000 Closing Costs Credit to Buyer closing by Oct. 31st. Best Value in Winchester! Charming and Spacious Custom Built Mid-Century Bungalow offers a terrific opportunity to live in Winchester! Do you want to send your children to the award-winning public schools? Need an in-law apt.? Generously sized, sun-drenched, freshly painted rooms with high ceilings and hardwood floors, beautiful

    John Magazzu Charlesgate Realty Group LLC

    84 Oak St, Winchester, MA 01890
  • /25

    $2,800 Per Month

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

    200 Swanton St Unit 705, Winchester, MA 01890

    All utilities included (heat, hot water, and electricity) in this top-floor 2-bedroom, 1-bath condo with stunning views over the treetops and duck pond. Its 7th-floor perch offers exceptional privacy, quiet, and floor-to-ceiling, south-facing windows that fill the home with natural light. One cat allowed. The kitchen and bath were fully renovated several years ago, and the entire unit has been

    Noha Soliman Leading Edge Real Estate

    200 Swanton St Unit 705, Winchester, MA 01890
  • /42

    $1,850,000

    Sold Jan 15, 2026

    77A Brooks St, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 4,122 Sq Ft
    • Built 1890

    Last Sold Summary

    • 19% Below List Price
    • $449/SF
    • 35 Days On Market

    Current Estimated Value $1,997,994

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    77A Brooks St, Winchester, MA 01890
    • /42

      Est $1,814,988

      Not Listed For Sale

      7 Wainwright Rd Unit 98, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,361 Sq Ft
      • Built 1995
      7 Wainwright Rd Unit 98, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

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

  • /38

    $1,999,000

    • 4 Beds
    • 2.5 Baths
    • 3,757 Sq Ft

    85 High St, Winchester, MA 01890

    Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a

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

    85 High St, Winchester, MA 01890
  • /18

    $3,500 Per Month

    • 3 Beds
    • 1.5 Baths
    • 968 Sq Ft
    • Apartment for Rent

    34 Charles Rd Unit 34, Winchester, MA 01890

    Bright and sunny 3 bedroom /1.5 bathroom town home in a quiet neighborhood in Winchester to rent. It features a nice floor plan with a new foyer/mudroom entrance, a spacious living room and dining area, a kitchen which can directly access to the beautiful back yard. The second floor offers three good sized bedrooms. The basement offers plenty storage space with included washer and dryer. Fenced

    Weidong Li WINN Real Estate & Consulting

    34 Charles Rd Unit 34, Winchester, MA 01890
  • /24

    $703,000

    Sold Jun 16, 2026

    115 Washington St Unit 2A, Winchester, MA 01890

    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $683/SF
    • 36 Days On Market

    Current Estimated Value $708,797

    Last Listing Agent Kim Covino Compass

    115 Washington St Unit 2A, Winchester, MA 01890
    • /27

      Est $1,332,398

      Not Listed For Sale

      7 Wainwright Rd Unit 22, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 3,350 Sq Ft
      • Built 1989
      7 Wainwright Rd Unit 22, Winchester, MA 01890

      Last Sold Summary

      • 183 Days On Market

      Last Listing Agent DeWolfe Group Gibson Sotheby's International Realty

  • /38

    $1,125,000

    Pending
    • 5 Beds
    • 2.5 Baths
    • 2,391 Sq Ft

    8 Oak St Unit 10, Winchester, MA 01890

    Thoughtfully updated 1870 home with a versatile footprint offering many options for multi-generational living, a grand home office setup, dedicated au pair quarters, or separately rented as an Accessory Dwelling Unit (ADU). Elegant renovations have preserved the home's original historic character while seamlessly incorporating today's modern luxuries. A charming farmer's porch welcomes you into

    Paul Cirignano The Synergy Group

    8 Oak St Unit 10, Winchester, MA 01890
  • /12

    $3,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Apartment for Rent

    28 East St, Winchester, MA 01890

    Spacious and well-maintained 3-bedroom, 2-bath townhouse featuring three levels of living space, with a large private yard and a storage shed. Enjoy hardwood floors throughout, a fully equipped kitchen with stainless steel appliances, and a finished basement with laundry and abundant storage space. The property includes 4 off-street parking spaces on a paved driveway. Conveniently located with an

    Jennifer Zhao HMW Real Estate, LLC

    28 East St, Winchester, MA 01890
  • /34

    $2,250,000

    Sold Sep 02, 2026

    6 Davey Ln, Winchester, MA 01890

    • 4 Beds
    • 4 Baths
    • 4,210 Sq Ft
    • Built 1996

    Last Sold Summary

    • 1% Above List Price
    • $534/SF
    • 4 Days On Market

    Current Estimated Value $2,064,267

    Last Listing Agent Gretchen Papineau Coldwell Banker Realty - Andovers/Readings Regional

    6 Davey Ln, Winchester, MA 01890
    • /42

      Est $1,870,330

      Not Listed For Sale

      7 Wainwright Rd Unit 5, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,901 Sq Ft
      • Built 1988
      7 Wainwright Rd Unit 5, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • /22

    $799,000

    $50K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    15 Clark St Unit 17, Winchester, MA 01890

    Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated

    Jeffrey Hsu Coldwell Banker Realty - Milton

    15 Clark St Unit 17, Winchester, MA 01890
  • /37

    $2,900 Per Month

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

    666 Main St Unit 315-3, Winchester, MA 01890

    Enjoy easy living at Wedgewood Place, a sought-after condominium community in the heart of Winchester Center. This spacious 2-bedroom, 2-bath home offers a bright, open layout with a wood-burning fireplace and a great balcony. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. The generous primary suite features

    Kim Covino Compass

    666 Main St Unit 315-3, Winchester, MA 01890
  • /33

    $1,936,000

    Sold Jun 23, 2026

    2 Gershon Way Unit 2, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,306 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Above List Price
    • $840/SF
    • 7 Days On Market

    Current Estimated Value $1,906,419

    Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

    2 Gershon Way Unit 2, Winchester, MA 01890
    • /41

      Est $1,623,837

      Not Listed For Sale

      7 Wainwright Rd Unit 41, Winchester, MA 01890

      • 2 Beds
      • 4 Baths
      • 5,564 Sq Ft
      • Built 1988
      7 Wainwright Rd Unit 41, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Jill Citrano Leading Edge Real Estate

  • /38

    $4,299,000

    • 5 Beds
    • 5.5 Baths
    • 6,526 Sq Ft

    4 Dartmouth St, Winchester, MA 01890

    Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined

    Nancy Pallotta Gibson Sotheby's International Realty

    4 Dartmouth St, Winchester, MA 01890
  • /31

    $3,700 Per Month

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

    10-12 Webster St Unit 1, Winchester, MA 01890

    Spacious 4-bedroom, 2-bath apartment available for immediate occupancy in a two-family home just minutes from Winchester Center. Please note: This is NOT a single-family home. This unique unit occupies the entire first floor and finished lower level. The main level features hardwood floors throughout, a living room, dining room, two spacious bedrooms, a full bath, and an eat-in kitchen with a new

    Ryan Kelly Real Broker MA, LLC

    10-12 Webster St Unit 1, Winchester, MA 01890
  • /41

    $1,820,000

    Sold Sep 10, 2026

    16 Glenwood Ave, Winchester, MA 01890

    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft
    • Built 1966

    Last Sold Summary

    • 17% Below List Price
    • $264/SF
    • 101 Days On Market

    Current Estimated Value $2,091,200

    Last Listing Agent Kim Covino Compass

    16 Glenwood Ave, Winchester, MA 01890
    • /15

      Est $1,135,855

      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

      • 6 Days On Market

      Last Listing Agent Joanne McDonnell McDonnell Real Estate Group, LLC

  • /35

    $1,699,000

    Pending
    • 5 Beds
    • 3.5 Baths
    • 3,180 Sq Ft

    30 Farrow St, Winchester, MA 01890

    Built in 2019 and perfectly positioned near downtown Winchester and the commuter rail, this 5 bed, 3.5 bath Colonial offers a bright, open layout with oversized windows, newly installed custom interior shutters and great natural light throughout. The large living room flows into the dining room, making the first floor great for everyday living and entertaining. The kitchen features a 2025

    Carlisle Group Compass

    30 Farrow St, Winchester, MA 01890
  • /19

    $4,400 Per Month

    • 3 Beds
    • 1.5 Baths
    • 2,000 Sq Ft
    • Apartment for Rent

    79 Church St Unit 1, Winchester, MA 01890

    Rare opportunity to rent an exceptionally spacious home on historic Church Street in the heart of Winchester! Offering over 2000 sq. ft. of living space, this charming Victorian features 3 generous bedrooms, 1.5 baths, a grand foyer, spacious living and dining rooms, and an eat-in kitchen with granite countertops and gas cooking. High ceilings, hardwood floors, original architectural details and

    Anna Mean AC Realty

    79 Church St Unit 1, Winchester, MA 01890
  • /42

    $1,700,000

    Sold Jun 29, 2026

    29 Pilgrim Dr, Winchester, MA 01890

    • 5 Beds
    • 3 Baths
    • 3,271 Sq Ft
    • Built 1963

    Last Sold Summary

    • 3% Below List Price
    • $520/SF
    • 20 Days On Market

    Current Estimated Value $1,737,516

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    29 Pilgrim Dr, Winchester, MA 01890
    • /42

      Est $2,000,869

      Not Listed For Sale

      40 Wainwright Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,853 Sq Ft
      • Built 1992
      40 Wainwright Rd, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Kim Covino Compass

  • /16

    $399,000

    Open Sat 10AM - 12PM
    • 1 Bed
    • 1 Bath
    • 613 Sq Ft

    200 Swanton St Unit 727, Winchester, MA 01890

    Welcome to Parkview Condominiums in Winchester! This well-maintained 1-bedroom, 1-bathroom condo offers comfortable living in a desirable location. The spacious living room features a glass slider that opens to a private balcony overlooking the pond and garden, perfect for relaxing and enjoying the peaceful surroundings. The condo fee includes all utilities, including heat, hot water, and

    Alice Zheng Shore Real Estate LLC

    200 Swanton St Unit 727, Winchester, MA 01890
  • /22

    $2,900 Per Month

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

    63-65 Harvard St Unit 2, Winchester, MA 01890

    Three bedrooms and an office in this two floor, second floor unit in Winchester. Open kitchen with pantry, spacious living room. Two bedrooms on this main level. Upstairs two more rooms. Two full baths and laundry in the basement. One car garage parking and plenty of space for several cars. Shareable backyard. All of this in the Muraco School District.

    Beth Sager Group Keller Williams Realty Boston Northwest

    63-65 Harvard St Unit 2, Winchester, MA 01890
  • /24

    $2,155,000

    Sold Oct 21, 2025

    7 Wainwright Rd Unit 13, Winchester, MA 01890

    • 3 Beds
    • 4.5 Baths
    • 3,186 Sq Ft
    • Built 1988

    Last Sold Summary

    • $676/SF
    • 1 Day On Market

    Current Estimated Value $1,856,310

    Last Listing Agent Isabella Bruno William Raveis R.E. & Home Services

    7 Wainwright Rd Unit 13, Winchester, MA 01890
    • /42

      Est $2,816,240

      Not Listed For Sale

      19 Socrates Way, Winchester, MA 01890

      • 5 Beds
      • 6 Baths
      • 5,678 Sq Ft
      • Built 1994
      19 Socrates Way, Winchester, MA 01890

      Last Sold Summary

      • 12 Days On Market

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

  • /42

    $975,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,475 Sq Ft

    199 Washington St, Winchester, MA 01890

    Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large,

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    199 Washington St, Winchester, MA 01890
  • /12

    $3,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,367 Sq Ft
    • Apartment for Rent

    52 Sheridan Cir Unit 52, Winchester, MA 01890

    This beautifully maintained residence offers a unique opportunity to lease a comfortable and stylish home.This residential property, built in 1997, offers 1367 square feet of inviting, move-in ready space, presenting an open floor plan living room, dining area and kitchen with hardwood floors and lots of windows with natural sunlight. Modern kitchen white cabinets, quartz counters, range,

    Robin Griffiths J. Mulkerin Realty

    52 Sheridan Cir Unit 52, Winchester, MA 01890
  • /37

    $888,000

    Sold Jun 08, 2026

    9 Governors Ave Unit 2, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,799 Sq Ft
    • Built 1903

    Last Sold Summary

    • 1% Below List Price
    • $494/SF
    • 6 Days On Market

    Current Estimated Value $883,967

    Last Listing Agent Philip Vita Compass

    9 Governors Ave Unit 2, Winchester, MA 01890
    • /42

      Est $2,294,406

      Not Listed For Sale

      17 Wagon Wheel Rd, Winchester, MA 01890

      • 5 Beds
      • 5 Baths
      • 3,940 Sq Ft
      • Built 1983
      17 Wagon Wheel Rd, Winchester, MA 01890

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Yifei Wang Dreamega International Realty LLC

Showing Results 81 - 120, Page 3 of 18

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