9,206

Winchester, MA Homes

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  • /37

    $1,499,000

    $100K PRICE DROP Pending
    • 4 Beds
    • 4 Baths
    • 2,480 Sq Ft

    241 Ridge St, Winchester, MA 01890

    New roof and fresh exterior paint just completed! This move-in-ready 4-bedroom, 2 full bath, 2 half bath home has been thoughtfully updated and meticulously maintained, offering the perfect blend of timeless charm, modern updates, and exceptional outdoor living in one of Winchester's most sought-after neighborhoods. Recent improvements include a brand-new roof, freshly painted exterior, all-new

    Team Lillian Montalto Lillian Montalto Signature Properties

    241 Ridge St, Winchester, MA 01890
  • /21

    $5,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,632 Sq Ft
    • House for Rent

    111 Highland Ave, Winchester, MA 01890

    Welcome to this spacious and charming Colonial offering beautiful architectural character, a flexible floor plan, and generous living space across multiple levels.Step into the welcoming foyer and discover a bright, inviting home featuring a fireplaced living room with beamed ceilings and oversized windows, complemented by a sun-filled adjoining sunroom.The beautiful kitchen features granite

    Michelle Li PWK Realty LLC

    111 Highland Ave, Winchester, MA 01890
  • /39

    $2,150,000

    Sold Jul 13, 2026

    22 Hollywood Rd, Winchester, MA 01890

    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft
    • Built 1962

    Last Sold Summary

    • 8% Above List Price
    • $686/SF
    • 8 Days On Market

    Current Estimated Value $1,971,943

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    22 Hollywood Rd, Winchester, MA 01890
    • /42

      Est $2,903,722

      Not Listed For Sale

      228 Ridge St, Winchester, MA 01890

      • 5 Beds
      • 5.5 Baths
      • 6,265 Sq Ft
      • Built 2023
      228 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 142 Days On Market

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

  • /4

    $3,200,000

    • 5 Beds
    • 5.5 Baths
    • 5,295 Sq Ft

    18 Ridge St, Winchester, MA 01890

    Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort.

    Gayle Winters Compass

    18 Ridge St, Winchester, MA 01890
  • /20

    $4,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    7 Park Ave Unit 7 Park Ave, Winchester, MA 01890

    Best Deal in Town! This luxurious townhome is now available for immediate occupancy. Spanning two floors, it boasts an exceptional layout. The main floor is particularly impressive, featuring a primary bedroom, an additional bedroom, Open Concept living room and dining area, and a bright, inviting eat-in kitchen. The kitchen is equipped with ample cabinets, counter space, and stainless steel

    7 Park Ave Unit 7 Park Ave, Winchester, MA 01890
  • /3

    $1,930,000

    Sold Jan 09, 2026

    8 Felsdale Close, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 3,658 Sq Ft
    • Built 1935

    Last Sold Summary

    • 7% Below List Price
    • $528/SF
    • 35 Days On Market

    Current Estimated Value $1,958,095

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    8 Felsdale Close, Winchester, MA 01890
    • /40

      Est $1,357,776

      Not Listed For Sale

      15 Wincrest Dr, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 2,529 Sq Ft
      • Built 1957
      15 Wincrest Dr, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kim Covino Compass

  • /42

    $1,650,000

    • 5 Beds
    • 3.5 Baths
    • 3,722 Sq Ft

    117 Highland Ave, Winchester, MA 01890

    Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The

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

    117 Highland Ave, Winchester, MA 01890
  • /9

    $4,200 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
  • /41

    $3,230,000

    Sold Aug 21, 2026

    2 Everett Ave, Winchester, MA 01890

    • 7 Beds
    • 6 Baths
    • 7,043 Sq Ft
    • Built 1916

    Last Sold Summary

    • 14% Below List Price
    • $459/SF
    • 99 Days On Market

    Current Estimated Value $3,484,883

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

    2 Everett Ave, Winchester, MA 01890
    • /33

      Est $1,459,872

      Not Listed For Sale

      10 Carriage Ln, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 2,034 Sq Ft
      • Built 1957
      10 Carriage Ln, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Peter Kasseris Serhant

  • /42

    $1,899,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,257 Sq Ft

    11 Bonad Rd, Winchester, MA 01890

    STUNNING newer construction 4 BR, 3.5 BA home offering a wonderful blend of luxury, style & functionality in a sought-after Muraco School neighborhood near the Fells! The heart of the home is the gorgeous oversized sun-filled kitchen featuring an impressive 10' island, quartz countertops, state-of-the-art appliances & spacious dining area overlooking the gorgeous private patio filled with lush

    Kim Covino Compass

    11 Bonad Rd, Winchester, MA 01890
  • /28

    $3,250 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,461 Sq Ft
    • Apartment for Rent

    60 Lake St Unit J, Winchester, MA 01890

    Welcome to this spacious 2-bedroom, 2.5-bath townhome in a highly desirable Winchester location with beautiful views of Wedge Pond. Offering multiple levels of living space, this home provides plenty of room to spread out, work from home, and relax.The main level features an open kitchen and dining area, creating a comfortable and functional space for everyday living and entertaining. Step

    Shannon Jenkins RE/MAX Realty Experts

    60 Lake St Unit J, Winchester, MA 01890
  • /42

    $1,580,000

    Sold Feb 26, 2026

    10 Trinity Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft
    • Built 1963

    Last Sold Summary

    • 11% Above List Price
    • $748/SF
    • 5 Days On Market

    Current Estimated Value $1,543,175

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Trinity Rd, Winchester, MA 01890
    • /39

      Est $1,377,940

      Not Listed For Sale

      9 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 3 Baths
      • 2,496 Sq Ft
      • Built 1957
      9 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

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

  • /42

    $3,200,000

    Open Sat 12:30PM - 2PM $200K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 6,100 Sq Ft

    9 Albamont Rd, Winchester, MA 01890

    Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases 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

    Kim Covino Compass

    9 Albamont Rd, Winchester, MA 01890
  • /27

    $3,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft
    • Condo for Rent

    666 Main St Unit 210, Winchester, MA 01890

    Welcome to 666 Main Street, offering comfortable, low-maintenance living in a convenient Winchester location! This spacious 2-bedroom, 2-bath residence features hardwood floors, newly updated bathrooms, and a bright, well-designed layout. The primary bedroom offers a generous walk-in closet and private bath, while the living room opens directly to a private patio—perfect for morning coffee or

    Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

    666 Main St Unit 210, Winchester, MA 01890
  • /40

    $1,715,000

    Sold Sep 03, 2026

    94 Johnson Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 3,366 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $510/SF
    • 34 Days On Market

    Current Estimated Value $1,782,114

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

    94 Johnson Rd, Winchester, MA 01890
    • /29

      Est $1,335,559

      Not Listed For Sale

      28 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 2 Baths
      • 2,245 Sq Ft
      • Built 1959
      28 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 117 Days On Market

      Last Listing Agent Shaundize Moosavizadeh Coldwell Banker Realty - Boston

  • /42

    $1,699,000

    Open Fri 4PM - 5:30PM
    • 3 Beds
    • 2 Baths
    • 2,421 Sq Ft

    4 Churchill Rd, Winchester, MA 01890

    COMMUTER OPEN HOUSE! Friday 4-5:30 9/25 Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and

    Kim Covino Compass

    4 Churchill Rd, Winchester, MA 01890
  • /19

    $3,500 Per Month

    • 3 Beds
    • 1 Bath
    • 1,700 Sq Ft
    • Apartment for Rent

    303 Washington St Unit 1, Winchester, MA 01890

    **Flexible lease terms** Prime location close to town! Spacious and beautifully maintained 3-bedroom first floor unit in the heart of Winchester, with a full driveway! This great home offers a blend of classic character and thoughtful updates. This unit has always been owner occupied and is in meticulous condition .. featuring generously sized rooms with high ceilings, oversized windows, hardwood

    Kim Covino Compass

    303 Washington St Unit 1, Winchester, MA 01890
  • /41

    $1,360,000

    Sold Jul 29, 2026

    15 Thornberry Rd, Winchester, MA 01890

    • 4 Beds
    • 3 Baths
    • 4,062 Sq Ft
    • Built 1957

    Last Sold Summary

    • 1% Above List Price
    • $335/SF
    • 7 Days On Market

    Current Estimated Value $1,365,421

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

    15 Thornberry Rd, Winchester, MA 01890
    • /37

      Est $1,504,318

      Not Listed For Sale

      65 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 2.5 Baths
      • 2,525 Sq Ft
      • Built 1965
      65 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jun Zhang HMW Real Estate, LLC

  • /32

    $2,695,000

    Open Sat 10:30AM - 12PM $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,233 Sq Ft

    18 Middlesex St, Winchester, MA 01890

    Seller to offer a buyer credit paying up to 2% of loan size for buyer at closing that can go to a permanent or temporary rate buydown. European inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes,

    Tina Natale Luxury Living Real Estate

    18 Middlesex St, Winchester, MA 01890
  • /19

    $3,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    341 Washington St Unit 2, Winchester, MA 01890

    Welcome to 341 Washington St, Winchester, MA! This spacious 3-bedroom, 1-bath apartment offers a comfortable and convenient layout in a desirable Winchester location.The unit features laundry, parking for 2 cars, and access to a backyard, providing extra space to relax and enjoy the outdoors.Conveniently located near local shops, restaurants, schools, public transportation, and major routes,

    Claudia Morais P&Co Real Estate

    341 Washington St Unit 2, Winchester, MA 01890
  • /28

    $1,200,000

    Sold May 29, 2026

    31 Mystic Ave Unit 33, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 2,129 Sq Ft
    • Built 1890

    Last Sold Summary

    • $564/SF
    • 27 Days On Market

    Last Listing Agent Kim Covino Compass

    31 Mystic Ave Unit 33, Winchester, MA 01890
    • /19

      Est $1,924,682

      Not Listed For Sale

      109 Thornberry Rd, Winchester, MA 01890

      • 4 Beds
      • 3.5 Baths
      • 3,784 Sq Ft
      • Built 1974
      109 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Andrew Martini Compass

  • /42

    $2,999,000

    Pending
    • 5 Beds
    • 4 Baths
    • 4,028 Sq Ft

    10 Dartmouth St, Winchester, MA 01890

    Capture the seasons from the stunning rear porch! Must see this move in ready waterfront gem! Perfectly sited at the end of Wedgemere on Winter Pond, offering over 80 feet of direct water frontage w/ expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this home presents a rare opportunity to enjoy water activities such as kayaking,

    Kim Covino Compass

    10 Dartmouth St, Winchester, MA 01890
  • /14

    $1,950 Per Month

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

    200 Swanton St Unit 416, Winchester, MA 01890

    The sought after Parkview Condominium! Prime Winchester Location ! Living room with glass sliders to balcony overlooking a calming and picturesque landscaped wildlife garden and pond with ducks & swans. Rent includes ALL utilities - heat, cold & hot water, electricity and 1 gated parking space! No pets. No smoking of any substances. Large bedroom for a king-size bed or twins and includes a

    Ai Cheng Goh Z. Realty

    200 Swanton St Unit 416, Winchester, MA 01890
  • /18

    $452,500

    Sold Mar 30, 2026

    22 Oak St, Winchester, MA 01890

    • 3 Beds
    • 1 Bath
    • 1,573 Sq Ft
    • Built 1910

    Last Sold Summary

    • $288/SF
    • 2 Days On Market

    Current Estimated Value $485,816

    Last Listing Agent Rameel Rana Advise Realty

    22 Oak St, Winchester, MA 01890
    • /35

      Est $1,705,406

      Not Listed For Sale

      22 Berkshire Dr, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 3,224 Sq Ft
      • Built 1967
      22 Berkshire Dr, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Timothy Morgan RE/MAX Innovative Properties

  • /42

    $1,870,000

    Open Sat 10:30AM - 11:30AM $29K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,210 Sq Ft

    79 Grove St, Winchester, MA 01890

    Space where you need it, flexibility where you want it. This extensively renovated 5-bedroom Colonial offers a rare combination of a first-floor bedroom, two upstairs suites, finished lower level, attached 2-car garage, and nearly 1/3 acre, all just minutes from Winchester Center. Sophisticated and comfortable, the home features beautifully scaled living spaces and a versatile floor plan designed

    Pirani & Wile Group Gibson Sotheby's International Realty

    79 Grove St, Winchester, MA 01890
  • /28

    $7,500 Per Month

    • 6 Beds
    • 4 Baths
    • 3,000 Sq Ft
    • House for Rent

    161 Highland Ave Unit n/a, Winchester, MA 01890

    Enjoy the best of Winchester living in this beautifully maintained six-bedroom, two-and-a-half-bath Colonial, ideally situated just moments from the Middlesex Fells Reservation. Available August 1, this spacious home offers a versatile layout designed for comfortable everyday living, with generous room sizes, abundant natural light, and central HVAC for year-round comfort. Outside, the

    Lisa Godwin Gibson Sotheby's International Realty

    161 Highland Ave Unit n/a, Winchester, MA 01890
  • /35

    $1,325,000

    Sold Aug 14, 2026

    3 Chesterford Terrace, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 2,006 Sq Ft
    • Built 1933

    Last Sold Summary

    • 2% Above List Price
    • $661/SF
    • 10 Days On Market

    Current Estimated Value $1,410,363

    Last Listing Agent Scott McNeill Compass

    3 Chesterford Terrace, Winchester, MA 01890
    • /33

      Est $1,762,821

      Not Listed For Sale

      85 Thornberry Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 2,848 Sq Ft
      • Built 1968
      85 Thornberry Rd, Winchester, MA 01890

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Diane Basemera Coldwell Banker Realty - Newton

  • /42

    $1,350,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 3 Baths
    • 2,690 Sq Ft

    423 Washington St, Winchester, MA 01890

    Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday

    Danielle Fleming MA Properties

    423 Washington St, Winchester, MA 01890
  • /41

    $4,850 Per Month

    • 5 Beds
    • 2 Baths
    • 2,174 Sq Ft
    • Apartment for Rent

    79 Bacon St Unit 79, Winchester, MA 01890

    Welcome to this spacious 3-story Colonial, where timeless curb appeal meets modern living. A bluestone path invites you to the main entry, setting the tone for a home designed for both comfort and sophistication. Inside, expansive living and dining rooms showcase wood trim and custom built-ins, while hardwood floors and oversized replacement windows flood the space with natural light. The heart

    Gayle Winters Compass

    79 Bacon St Unit 79, 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

    Current Estimated Value $2,039,319

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

    64 Westland Ave, Winchester, MA 01890
    • /40

      Est $2,008,813

      Not Listed For Sale

      3 Berkshire Dr, Winchester, MA 01890

      • 5 Beds
      • 2.5 Baths
      • 3,344 Sq Ft
      • Built 1967
      3 Berkshire Dr, Winchester, MA 01890

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Allison Shannon Charlesgate Realty Group, llc

Showing Results 41 - 80, Page 2 of 18

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