9,200

Winchester, MA Homes

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  • /40

    $1,675,000

    $50K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,722 Sq Ft

    117 Highland Ave, Winchester, MA 01890

    Excellent New Price! Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace,

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

    117 Highland Ave, 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 Zhensight 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
    • /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

  • /40

    $1,799,000

    Pending
    • 4 Beds
    • 3 Baths
    • 3,366 Sq Ft

    94 Johnson Rd, Winchester, MA 01890

    Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated

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

    94 Johnson Rd, Winchester, MA 01890
  • /9

    $4,600 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
  • /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
    • /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

  • /10

    $3,200,000

    $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
  • /24

    $2,900 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Apartment for Rent

    926 Main St Unit 2, Winchester, MA 01890

    Available 9/1!! Beautifully updated second-floor apartment offering more than 1,000 square feet with 6 rooms, 2 spacious bedrooms, 1 full bath, and a home office in one of Winchester's most convenient commuter locations. Directly on the bus line and just moments from Winchester Center, the MBTA commuter rail, restaurants, shops, and major routes, this home combines space, comfort, and

    Nancy Pallotta Gibson Sotheby's International Realty

    926 Main St Unit 2, 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
    • /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

  • /35

    $1,300,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 2,006 Sq Ft

    3 Chesterford Terrace, Winchester, MA 01890

    Nestled at the end of a coveted cul-de-sac, 3 Chesterford Terrace presents a rare opportunity to own a timeless Winchester home on a picture-perfect 12,972 SQ FT flat lot. Designed by renowned Winchester architect Jerome Bailey Foster, this charming 3+ bed, 1.5-bath residence blends classic architectural character with an exceptional setting. Surrounded by mature landscaping & set on one of

    Scott McNeill Compass

    3 Chesterford Terrace, Winchester, MA 01890
  • /19

    $3,900 Per Month

    • 3 Beds
    • 3 Baths
    • 1,900 Sq Ft
    • House for Rent

    159 Cross St Unit 159, Winchester, MA 01890

    Wonderful opportunity to rent a single family home in Winchester. Main level welcomes you in to a fireplaced Livingroom with hardwood floors and formal dining room with direct access to Eat-in Kitchen featuring granite counters, tile floor and good storage. Second floor offers an over sized full bath with tile floor and three bedrooms all with hardwood floors. Lower level is finished with tile

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

    159 Cross St Unit 159, Winchester, MA 01890
  • /2

    $720,000

    Sold Aug 26, 2025

    29 Vine St Unit 7, Winchester, MA 01890

    • 2 Beds
    • 1.5 Baths
    • 1,300 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Above List Price
    • $554/SF
    • 4 Days On Market

    Current Estimated Value $742,851

    Last Listing Agent Philip Vita Compass

    29 Vine St Unit 7, 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

  • /34

    $2,225,000

    Pending
    • 4 Beds
    • 4 Baths
    • 4,210 Sq Ft

    6 Davey Ln, Winchester, MA 01890

    Rarely available in one of Winchester’s most desirable neighborhoods, this beautifully maintained Colonial offers the perfect blend of modern comfort and convenience. Set on a quiet cul-de-sac surrounded by historic homes, this late 1990s residence provides newer construction, a thoughtfully designed floor plan and an exceptional location just minutes from Winchester Center, commuter rail,

    Gretchen Papineau Coldwell Banker Realty - Andovers/Readings Regional

    6 Davey Ln, Winchester, MA 01890
  • /20

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • House for Rent

    22 Baldwin St, Winchester, MA 01890

    Beautifully renovated single-family home on a quiet cul-de-sac in desirable Winchester. Situated on a spacious 9,500± sq. ft. lot, this move-in-ready home features newly finished hardwood floors throughout, an open-concept living and dining area, an updated kitchen with gas cooking, a cozy family room with a wood-burning fireplace, and a full bath on the main level. Upstairs offers three spacious

    Qian Han JW Real Estate Services, LLC

    22 Baldwin St, 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
    • /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

  • /41

    $1,899,000

    $301K PRICE DROP Pending
    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft

    16 Glenwood Ave, Winchester, MA 01890

    Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr

    Kim Covino Compass

    16 Glenwood Ave, Winchester, MA 01890
  • /42

    $6,995 Per Month

    • 4 Beds
    • 2.5 Baths
    • 4,253 Sq Ft
    • House for Rent

    18 Grant Rd, Winchester, MA 01890

    Located in a favorite Winchester neighborhood, this spacious and thoughtfully designed home offers an ideal layout for today's lifestyle. The oversized family room flows seamlessly from the kitchen, creating a perfect space for entertaining and everyday living. The kitchen features modern appliances and a slider to the back deck for easy indoor-outdoor enjoyment. A first-floor bedroom or home

    Kim Covino Compass

    18 Grant Rd, 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
    • /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

  • /42

    $2,450,000

    $145K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 4,403 Sq Ft

    50 Brooks St, Winchester, MA 01890

    Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home &

    Kim Covino Compass

    50 Brooks St, Winchester, MA 01890
  • /15

    $4,800 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,657 Sq Ft
    • House for Rent

    17 Russell Rd, Winchester, MA 01890

    Move in date: Now. Tenant pays all utilities (gas, heat, electricity, cold/hot water and trash disposal). Lead Paint: Certified Treated. 2 off street parking. Central AC ,Pets negotiable. Laundry in the unit. 12-month lease minimum Move-in costs: First month's rent, one month's rent as a security deposit, Last month rent Welcome to 17 Russell Road, a well-maintained single-family home tucked away

    KoKo Kwan Kwan Realty Inc.

    17 Russell Rd, 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 $3,282,100

    Last Listing Agent Philip Vita Compass

    18 Wickham Rd, 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

  • /32

    $2,695,000

    $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,233 Sq Ft

    18 Middlesex St, Winchester, MA 01890

    This 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, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the

    Tina Natale Luxury Living Real Estate

    18 Middlesex St, Winchester, MA 01890
  • /11

    $2,300 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Apartment for Rent

    4 Border St Unit 4, Woburn, MA 01801

    Available September 1st! A two bedroom, kitchen, living room and full bath. This unit has hardwood floors and many windows letting in plenty of sunlight. Basement has laundry hook ups and 1 spot for parking. Convenient to Shopping, Schools, Restaurants, Library, Horn Pond and Major Highway access. S.howings will begin August 18th

    Robin Griffiths J. Mulkerin Realty

    4 Border St Unit 4, Woburn, MA 01801
  • /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
    • /42

      Est $1,770,082

      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

  • /36

    $3,149,000

    $101K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    8 Priscilla Ln, Winchester, MA 01890

    Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef's kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and

    The Pezzano Group Rise Signature Homes

    8 Priscilla Ln, Winchester, MA 01890
  • /14

    $2,050 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
  • /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 $1,524,849

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

    155 Highland Ave, 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

  • /42

    $2,999,000

    • 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
  • /28

    $7,500 Per Month

    • 6 Beds
    • 3 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
  • /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
    • /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

Showing Results 41 - 80, Page 2 of 18

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