9,270

Homes in ZIP Code 01890

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  • /41

    $2,099,000

    $101K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft

    16 & 16A Glenwood Ave, Winchester, MA 01890

    Must see! sprawling 2-3 family beautifully renovated & expanded home 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,

    Kim Covino Compass

    16 & 16A Glenwood Ave, Winchester, MA 01890
  • /36

    $3,200 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,332 Sq Ft
    • Condo for Rent

    7 Conant Rd Unit 11, Winchester, MA 01890

    Available 8/1/2026! Highly Desirable The Willows Condominiums.... Sunny 2 bedrooms and 2.5 bathrooms second floor unit... Open layout living room, dining room, kitchen & sliding door leads to private deck.... In-unit laundry, Stainless Steel Appliances, Gas fireplace, Hardwood floors... Gas heating with Central AC... Spacious master bedroom with large walk-in closet and bathroom in suite...

    Young Wang Phoenix Real Estate Partners, LLC

    7 Conant Rd Unit 11, Winchester, MA 01890
  • /41

    $2,425,000

    Sold Jul 31, 2025

    15 Churchill Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 5,501 Sq Ft
    • Built 2025

    Last Sold Summary

    • 7% Below List Price
    • $441/SF
    • 61 Days On Market

    Current Estimated Value $2,466,164

    Last Listing Agent Kim Covino Compass

    15 Churchill Rd, Winchester, MA 01890
    • /36

      Est $2,316,747

      Not Listed For Sale

      9 Amberwood Dr, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,257 Sq Ft
      • Built 2021
      9 Amberwood Dr, Winchester, MA 01890

      Last Sold Summary

      • 195 Days On Market

  • /12

    $2,399,000

    Open Sat 11AM - 12PM $400K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 5,083 Sq Ft

    53 Winford Way, Winchester, MA 01890

    Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient

    Andersen Group Realty Keller Williams Realty Boston Northwest

    53 Winford Way, Winchester, MA 01890
  • /9

    $3,500 Per Month

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

    63 Holland St Unit 63, Winchester, MA 01890

    Welcome to 63 Holland St in Winchester! This beautifully renovated 2-bedroom, 1-bath townhome offers the perfect blend of classic charm and modern updates, featuring hardwood floors throughout, recessed lighting, freshly painted interiors, and a stunning new kitchen with quartz countertops and stainless steel appliances. The updated bathroom showcases a walk-in tiled shower with a custom glass

    Issam Dib Skyline Realty

    63 Holland St Unit 63, Winchester, MA 01890
  • /23

    $950,000

    Sold Dec 04, 2025

    16 Park Ave Unit 1, Winchester, MA 01890

    • 3 Beds
    • 2 Baths
    • 1,535 Sq Ft
    • Built 1915

    Last Sold Summary

    • 5% Below List Price
    • $619/SF
    • 26 Days On Market

    Current Estimated Value $979,062

    Last Listing Agent Andrea Mackey The Agency Boston

    16 Park Ave Unit 1, Winchester, MA 01890
    • /42

      Est $2,424,951

      Not Listed For Sale

      5 Pilgrim Dr, Winchester, MA 01890

      • 6 Beds
      • 3.5 Baths
      • 4,138 Sq Ft
      • Built 1962
      5 Pilgrim Dr, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

  • /31

    $1,199,000

    Open Sat 10AM - 12PM $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,420 Sq Ft

    129 Washington St Unit 131, Winchester, MA 01890

    Prime Winchester location just moments from Winchester Center, within walking distance to elementary, middle, high school, downtown and commuter rail. Ideal for commuters and locals alike. This townhouse-style condo lives like a single-family, offering space, flow, and flexibility across four finished levels. The main living area is designed for how you actually live, with an open layout that

    The Mary Scimemi Team Leading Edge Real Estate

    129 Washington St Unit 131, Winchester, MA 01890
  • /20

    $4,850 Per Month

    • 4 Beds
    • 1.5 Baths
    • 1,700 Sq Ft
    • House for Rent

    488 Washington St, Winchester, MA 01890

    Charming, updated Colonial filled with character. This beautiful home features an updated kitchen that is bright and open and offers granite counter tops, stainless steel appliances, frameless maple cabinets & recessed lights. Updated bathrooms. Hardwood floors throughout the 1st & 2nd floors. Access the stone and granite patio through French doors in the dining room. The patio is fenced in and

    Matthew Pierce True North Realty

    488 Washington St, Winchester, MA 01890
  • /38

    $2,600,000

    Sold Jun 18, 2026

    15 York Rd, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • Built 2017

    Last Sold Summary

    • 4% Above List Price
    • $578/SF
    • 7 Days On Market

    Current Estimated Value $2,601,163

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

    15 York Rd, Winchester, MA 01890
    • /40

      Est $1,501,516

      Not Listed For Sale

      16 Johnson Rd, Winchester, MA 01890

      • 3 Beds
      • 2 Baths
      • 3,142 Sq Ft
      • Built 1958
      16 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

  • /42

    $2,950,000

    $349K PRICE DROP Pending
    • 5 Beds
    • 4.5 Baths
    • 5,202 Sq Ft

    74 Wedgemere Ave, Winchester, MA 01890

    The most idyllic setting in town! This beautifully renovated and expanded Colonial blends timeless charm with modern sophistication. Perfectly sited on an 18,000 sq ft lot abutting conservation land, it offers exceptional privacy in one of the town’s most coveted neighborhoods. This stunning home features 5+ bedrooms and 4.5 baths, with new windows, updated systems, an expanded kitchen, and

    Kim Covino Compass

    74 Wedgemere Ave, Winchester, MA 01890
  • /29

    $5,200 Per Month

    • 4 Beds
    • 3.5 Baths
    • 1,928 Sq Ft
    • Apartment for Rent

    48 Spruce St Unit 1, Winchester, MA 01890

    Spacious 4-bedroom, 3.5-bath townhouse ideally located within walking distance to the town center, schools, and commuter rail. This well-maintained home features beautiful hardwood flooring throughout, a bright and functional layout, and generous living space perfect for everyday living and entertaining. Enjoy outdoor living with a private fenced-in patio. Landscaped yard space. Additional

    Dylan Archambault Archambault Real Estate

    48 Spruce St Unit 1, Winchester, MA 01890
  • /35

    $2,575,000

    Sold May 14, 2026

    2 Abby Rd, Winchester, MA 01890

    • 4 Beds
    • 4.5 Baths
    • 5,614 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Below List Price
    • $459/SF
    • 12 Days On Market

    Current Estimated Value $2,646,202

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    2 Abby Rd, Winchester, MA 01890
    • /42

      Est $1,842,115

      Not Listed For Sale

      19 Johnson Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 4,318 Sq Ft
      • Built 1956
      19 Johnson Rd, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

  • /39

    $1,949,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,494 Sq Ft

    2 York Rd, Winchester, MA 01890

    Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet & spa-like bath with an oversized

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

    2 York Rd, Winchester, MA 01890
  • /42

    $2,650,000

    Sold Apr 21, 2026

    45 Bacon St, Winchester, MA 01890

    • 7 Beds
    • 8 Baths
    • 7,043 Sq Ft
    • Built 2011

    Last Sold Summary

    • 11% Below List Price
    • $376/SF
    • 29 Days On Market

    Current Estimated Value $2,800,406

    Last Listing Agent Kim Covino Compass

    45 Bacon St, Winchester, MA 01890
    • /33

      Est $1,883,627

      Not Listed For Sale

      8 Olde Lyme Rd, Winchester, MA 01890

      • 5 Beds
      • 3.5 Baths
      • 4,603 Sq Ft
      • Built 1960
      8 Olde Lyme Rd, Winchester, MA 01890

      Last Sold Summary

      • 2 Days On Market

  • /42

    $1,689,000

    Pending
    • 3 Beds
    • 2 Baths
    • 3,090 Sq Ft

    41 Sunset Rd, Winchester, MA 01890

    Completely gut renovated in 2023, this stunning home overlooks conservation & offers serene views, privacy & lives like-new construction. The home was thoughtfully redesigned & opened up to feature dramatic soaring vaulted ceilings & an open floor plan, flooded with natural light. The designer kitchen is the centerpiece of the home, showcasing custom cabinetry, paneled appliances, oversized

    Kim Covino Compass

    41 Sunset Rd, Winchester, MA 01890
  • /42

    $1,700,000

    Sold May 01, 2026

    114 Johnson Rd, Winchester, MA 01890

    • 3 Beds
    • 3 Baths
    • 3,182 Sq Ft
    • Built 1880

    Last Sold Summary

    • 5% Below List Price
    • $534/SF
    • 22 Days On Market

    Current Estimated Value $1,764,234

    Last Listing Agent Rosemary Kelleher LAER Realty Partners

    114 Johnson Rd, Winchester, MA 01890
    • /25

      Est $1,912,364

      Not Listed For Sale

      4 Olde Lyme Rd, Winchester, MA 01890

      • 4 Beds
      • 4 Baths
      • 3,488 Sq Ft
      • Built 1980
      4 Olde Lyme Rd, Winchester, MA 01890

      Last Sold Summary

      • 34 Days On Market

  • /42

    $3,549,000

    $201K PRICE DROP Pending
    • 6 Beds
    • 4.5 Baths
    • 6,460 Sq Ft

    40 Foxcroft Rd, Winchester, MA 01890

    40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows.

    The Boston ONE Team Serhant

    40 Foxcroft Rd, Winchester, MA 01890
  • /42

    $1,830,000

    Sold Feb 26, 2026

    35 Glen Green, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 3,509 Sq Ft
    • Built 1934

    Last Sold Summary

    • 8% Below List Price
    • $522/SF
    • 36 Days On Market

    Current Estimated Value $1,874,372

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    35 Glen Green, Winchester, MA 01890
    • /42

      Est $2,261,727

      Not Listed For Sale

      239 Ridge St, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 4,473 Sq Ft
      • Built 2018
      239 Ridge St, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

  • /34

    $1,100,000

    • 2 Beds
    • 1.5 Baths
    • 1,365 Sq Ft

    83 Church St Unit 15, Winchester, MA 01890

    Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal

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

    83 Church St Unit 15, Winchester, MA 01890
  • /42

    $1,330,000

    Sold Apr 14, 2026

    40 Pickering St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,454 Sq Ft
    • Built 1870

    Last Sold Summary

    • 6% Above List Price
    • $542/SF
    • 0 Days On Market

    Current Estimated Value $1,288,673

    Last Listing Agent Timothy Haynes Keller Williams Realty Signature Properties

    40 Pickering St, Winchester, MA 01890
    • /26

      Est $1,166,928

      Not Listed For Sale

      75 Dunster Ln, Winchester, MA 01890

      • 3 Beds
      • 2.5 Baths
      • 1,826 Sq Ft
      • Built 1928
      75 Dunster Ln, Winchester, MA 01890

      Last Sold Summary

      • 15 Days On Market

  • /36

    $999,000

    $100K PRICE DROP Pending
    • 5 Beds
    • 2 Baths
    • 2,160 Sq Ft

    339-341 Washington St, Winchester, MA 01890

    Exceptional opportunity for investors, owner-occupants, or multigenerational living in this two-family home conveniently located near Winchester Center, restaurants, shopping, commuter rail, and major routes. The first floor has 2 bedrooms plus an office, while the second floor includes a third bedroom. Both units are filled with natural light and share nearly identical layouts with enclosed

    Nancy Pallotta Gibson Sotheby's International Realty

    339-341 Washington St, Winchester, MA 01890
  • /42

    $2,890,000

    Sold Aug 14, 2025

    21 Fernway, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,386 Sq Ft
    • Built 1963

    Last Sold Summary

    • $537/SF
    • 9 Days On Market

    Current Estimated Value $2,972,365

    Last Listing Agent Kim Covino Compass

    21 Fernway, Winchester, MA 01890
    • /42

      Est $3,064,248

      Not Listed For Sale

      222 High St, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 5,676 Sq Ft
      • Built 2006
      222 High St, Winchester, MA 01890

      Last Sold Summary

      • 0 Days On Market

  • /42

    $1,100,000

    Open Sat 12:30PM - 1:30PM
    • 4 Beds
    • 2 Baths
    • 2,085 Sq Ft

    41 Cross St, Winchester, MA 01890

    Freshly painted side-entrance Colonial offering space, flexibility, and a prime Winchester location. The expansive eat-in kitchen flows seamlessly into the dining area and family room, creating an ideal layout for everyday living and entertaining. The main level includes a bedroom or office, full bath, mudroom with laundry, and is well-suited for one-level living. Upstairs features three

    Andersen Group Realty Keller Williams Realty Boston Northwest

    41 Cross St, Winchester, MA 01890
  • /30

    $900,000

    Sold Oct 20, 2025

    171 Swanton St Unit 5, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 1,843 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $488/SF
    • 8 Days On Market

    Current Estimated Value $922,275

    Last Listing Agent Jonathan Radford Coldwell Banker Realty - Boston

    171 Swanton St Unit 5, Winchester, MA 01890
    • /30

      Est $964,893

      Not Listed For Sale

      62 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 2.5 Baths
      • 1,857 Sq Ft
      • Built 1985
      62 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

  • /40

    $3,099,000

    Pending
    • 6 Beds
    • 8 Baths
    • 7,168 Sq Ft

    4 Lawrence St, Winchester, MA 01890

    A beautifully renovated and expanded Colonial in the Flats, blending old-world charm with modern living that suits a myriad of needs. The main home features high ceilings, restored original woodwork, and updated systems throughout. The kitchen invites the outdoors in with views of the private, tree-lined backyard with mature plantings, an expansive covered patio, and firepit for cozy evenings.

    Burbs To Boston Compass

    4 Lawrence St, Winchester, MA 01890
  • /40

    $645,000

    Sold Jun 16, 2026

    17 Charles Rd Unit 17, Winchester, MA 01890

    • 2 Beds
    • 2 Baths
    • 1,326 Sq Ft
    • Built 1963

    Last Sold Summary

    • 8% Above List Price
    • $486/SF
    • 10 Days On Market

    Current Estimated Value $611,380

    Last Listing Agent Jessica Later JL+CoRE

    17 Charles Rd Unit 17, Winchester, MA 01890
    • /27

      Est $1,102,164

      Not Listed For Sale

      46 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,859 Sq Ft
      • Built 1985
      46 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 8 Days On Market

  • /41

    $4,449,000

    $250K PRICE DROP
    • 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 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 entertaining and

    Nancy Pallotta Gibson Sotheby's International Realty

    4 Dartmouth St, Winchester, MA 01890
  • /32

    $868,000

    Sold Sep 04, 2025

    235 Cross St, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,931 Sq Ft
    • Built 1956

    Last Sold Summary

    • 16% Above List Price
    • $450/SF
    • 8 Days On Market

    Current Estimated Value $927,917

    Last Listing Agent Melanie Lentini Leading Edge Real Estate

    235 Cross St, Winchester, MA 01890
    • /36

      Est $1,025,095

      Not Listed For Sale

      55 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,568 Sq Ft
      • Built 1987
      55 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

Showing Results 121 - 160, Page 4 of 18

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