9,200

Winchester, MA Homes

Section Image
  • 112 Highland Ave, Winchester, MA 01890
    112 Highland Ave, Winchester, MA 01890
    112 Highland Ave, Winchester, MA 01890
    /42

    $2,495,000

    Pending
    • 6 Beds
    • 3.5 Baths
    • 5,121 Sq Ft

    112 Highland Ave, Winchester, MA 01890

    Timeless Victorian grandeur meets modern living in this iconic Winchester home situated on the corner of Wilson Street w/ easy access to Fells trails! This recently renovated sun-filled 6 BR 4 BA home offers nearly 5000 ft.2 of beautifully scaled living spaces filled w/ extraordinary architectural charm & elegant details featuring a brand new state of the art gorgeous kitchen w/ Wolf & Sub Zero

    Kim Covino Compass

    112 Highland Ave, Winchester, MA 01890
  • 58 Oak St Unit 58, Winchester, MA 01890
    58 Oak St Unit 58, Winchester, MA 01890
    58 Oak St Unit 58, Winchester, MA 01890
    /18

    $2,750 Per Month

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

    58 Oak St Unit 58, Winchester, MA 01890

    Don't miss this beautifully updated upper-level apartment at 58 Oak Street, offering two floors of bright, spacious living in one of Winchester's most convenient locations! Combining modern updates with classic charm, this sun-filled home features hardwood floors throughout, high ceilings, central air conditioning, and in-unit laundry for everyday comfort. The spacious eat-in kitchen offers ample

    Marika & Associates Group Hammond Residential Real Estate

    58 Oak St Unit 58, Winchester, MA 01890
  • 518 Washington St, Winchester, MA 01890
    518 Washington St, Winchester, MA 01890
    518 Washington St, Winchester, MA 01890
    /40

    $1,160,000

    Sold Aug 14, 2025

    518 Washington St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,302 Sq Ft
    • Built 1915

    Last Sold Summary

    • 3% Below List Price
    • $504/SF
    • 22 Days On Market

    Current Estimated Value $1,231,718

    Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

    518 Washington St, Winchester, MA 01890
    • 4 Olde Lyme Rd, Winchester, MA 01890
      4 Olde Lyme Rd, Winchester, MA 01890
      4 Olde Lyme Rd, Winchester, MA 01890
      /25

      Est $1,846,007

      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

      Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  • 16 & 16A Glenwood Ave, Winchester, MA 01890
    16 & 16A Glenwood Ave, Winchester, MA 01890
    16 & 16A Glenwood Ave, Winchester, MA 01890
    /41

    $1,899,000

    $301K PRICE DROP Pending
    • 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
  • 270 Cross St Unit SF, Winchester, MA 01890
    270 Cross St Unit SF, Winchester, MA 01890
    270 Cross St Unit SF, Winchester, MA 01890
    /34

    $6,000 Per Month

    • 4 Beds
    • 4 Baths
    • 2,700 Sq Ft
    • House for Rent

    270 Cross St Unit SF, Winchester, MA 01890

    Beautifully renovated 4BR/4BA home in Winchester’s desirable Lynch School District offering three levels of modern living. The main floor features a dedicated office, hardwood floors, mini-split cooling, a wood-burning fireplace, 2-zone Nest heating, and a spacious kitchen with quartz countertops and stainless steel appliances. The walkout lower level is perfect for an in-law or au-pair suite

    The Abundant Group Real Broker MA, LLC

    270 Cross St Unit SF, Winchester, MA 01890
  • 16 Park Ave Unit 1, Winchester, MA 01890
    16 Park Ave Unit 1, Winchester, MA 01890
    16 Park Ave Unit 1, 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 $974,620

    Last Listing Agent Andrea Mackey The Agency Boston

    16 Park Ave Unit 1, Winchester, MA 01890
    • 75 Dunster Ln, Winchester, MA 01890
      75 Dunster Ln, Winchester, MA 01890
      75 Dunster Ln, Winchester, MA 01890
      /26

      Est $1,173,020

      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

      Last Listing Agent Adriano Varano Keller Williams Realty

  • 53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    /24

    $2,399,000

    $400K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 5,083 Sq Ft

    53 Winford Way, Winchester, MA 01890

    Offer Deadline AUGUST 17, 12 pm - see firm remarks for offer submission. 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

    Andersen Group Realty Keller Williams Realty Boston Northwest

    53 Winford Way, Winchester, MA 01890
  • 7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    /30

    $3,200 Per Month

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

    7 Ridge St, Winchester, MA 01890

    Welcome to this charming 2-bedroom, 1.5-bath rental located on the desirable west side of Winchester. Offering three levels of living space, this home provides plenty of room to spread out and enjoy a comfortable, flexible layout. Beautiful hardwood floors add warmth and character throughout, while the level, partially fenced backyard provides a wonderful private outdoor space for relaxing,

    Shannon Jenkins RE/MAX Realty Experts

    7 Ridge St, Winchester, MA 01890
  • 15 York Rd, Winchester, MA 01890
    15 York Rd, Winchester, MA 01890
    15 York Rd, 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 $2,494,290

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

    15 York Rd, Winchester, MA 01890
    • 222 High St, Winchester, MA 01890
      222 High St, Winchester, MA 01890
      222 High St, Winchester, MA 01890
      /42

      Est $3,084,305

      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

      Last Listing Agent Gayle Winters Compass

  • 129 Washington St Unit 131, Winchester, MA 01890
    129 Washington St Unit 131, Winchester, MA 01890
    129 Washington St Unit 131, Winchester, MA 01890
    /30

    $1,099,000

    $200K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,420 Sq Ft

    129 Washington St Unit 131, Winchester, MA 01890

    Experience the best of Winchester with a home that pairs exceptional value with an unbeatable location. Just moments from Winchester Center, enjoy a low-maintenance lifestyle within walking distance of downtown, the commuter rail, and all three school levels. This townhouse-style condo lives like a single-family home, offering space, flow, and flexibility across four finished levels. The open

    The Mary Scimemi Team Leading Edge Real Estate

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

    $4,495 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
  • 2 Abby Rd, Winchester, MA 01890
    2 Abby Rd, Winchester, MA 01890
    2 Abby Rd, 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 $2,601,690

    Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

    2 Abby Rd, Winchester, MA 01890
    • 62 Edward Dr, Winchester, MA 01890
      62 Edward Dr, Winchester, MA 01890
      62 Edward Dr, Winchester, MA 01890
      /30

      Est $937,599

      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

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

  • 7 Hutchinson Rd, Winchester, MA 01890
    7 Hutchinson Rd, Winchester, MA 01890
    7 Hutchinson Rd, Winchester, MA 01890
    /42

    $3,450,000

    • 6 Beds
    • 4.5 Baths
    • 5,735 Sq Ft

    7 Hutchinson Rd, Winchester, MA 01890

    Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the oversized three car garage into the

    Kim Covino Compass

    7 Hutchinson Rd, Winchester, MA 01890
  • 48 Spruce St Unit 1, Winchester, MA 01890
    48 Spruce St Unit 1, Winchester, MA 01890
    48 Spruce St Unit 1, Winchester, MA 01890
    /29

    $5,000 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 The Archambault Group

    48 Spruce St Unit 1, Winchester, MA 01890
  • 45 Bacon St, Winchester, MA 01890
    45 Bacon St, Winchester, MA 01890
    45 Bacon St, 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 $2,814,090

    Last Listing Agent Kim Covino Compass

    45 Bacon St, Winchester, MA 01890
    • 46 Edward Dr, Winchester, MA 01890
      46 Edward Dr, Winchester, MA 01890
      46 Edward Dr, Winchester, MA 01890
      /27

      Est $1,088,503

      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

      Last Listing Agent Sam Zhu Keller Williams Realty

  • 83 Church St Unit 15, Winchester, MA 01890
    83 Church St Unit 15, Winchester, MA 01890
    83 Church St Unit 15, Winchester, MA 01890
    /37

    $999,000

    $101K PRICE DROP
    • 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
  • 60 Graystone Cir Unit 60, Winchester, MA 01890
    60 Graystone Cir Unit 60, Winchester, MA 01890
    60 Graystone Cir Unit 60, Winchester, MA 01890
    /39

    $6,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft
    • Apartment for Rent

    60 Graystone Cir Unit 60, Winchester, MA 01890

    Meticulously maintained, 2/3-bedroom, 2.5-bath townhome with 2 car garage. The kitchen features custom cabinets, granite countertops, high-end stainless steel appliances and gleaming hardwood floors. The living/dining room combo features hardwood floors, gas fireplace, cathedral ceilings along with french doors that open to a private patio with gas grill. Spacious first floor primary suite boasts

    Pirani & Wile Group Gibson Sotheby's International Realty

    60 Graystone Cir Unit 60, Winchester, MA 01890
  • 114 Johnson Rd, Winchester, MA 01890
    114 Johnson Rd, Winchester, MA 01890
    114 Johnson 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 $1,696,035

    Last Listing Agent Rosemary Kelleher LAER Realty Partners

    114 Johnson Rd, Winchester, MA 01890
    • 55 Edward Dr, Winchester, MA 01890
      55 Edward Dr, Winchester, MA 01890
      55 Edward Dr, Winchester, MA 01890
      /36

      Est $1,023,075

      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

      Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  • 339-341 Washington St, Winchester, MA 01890
    339-341 Washington St, Winchester, MA 01890
    339-341 Washington St, Winchester, MA 01890
    /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
  • 35 Glen Green, Winchester, MA 01890
    35 Glen Green, Winchester, MA 01890
    35 Glen Green, 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 $1,883,181

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    35 Glen Green, Winchester, MA 01890
    • 41 Edward Dr, Winchester, MA 01890
      41 Edward Dr, Winchester, MA 01890
      41 Edward Dr, Winchester, MA 01890
      /42

      Est $1,076,384

      Not Listed For Sale

      41 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,738 Sq Ft
      • Built 1985
      41 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Beth Sager Group Keller Williams Realty Boston Northwest

  • 666 Main St Unit 211, Winchester, MA 01890
    666 Main St Unit 211, Winchester, MA 01890
    666 Main St Unit 211, Winchester, MA 01890
    /42

    $700,000

    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    666 Main St Unit 211, Winchester, MA 01890

    Great layout and numerous recent improvements make this a wonderful opportunity! Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new chandelier. Spacious

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    666 Main St Unit 211, Winchester, MA 01890
  • 40 Pickering St, Winchester, MA 01890
    40 Pickering St, Winchester, MA 01890
    40 Pickering St, 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 $1,300,556

    Last Listing Agent Timothy Haynes Keller Williams Realty Signature Properties

    40 Pickering St, Winchester, MA 01890
    • 34 Edward Dr, Winchester, MA 01890
      34 Edward Dr, Winchester, MA 01890
      34 Edward Dr, Winchester, MA 01890
      /38

      Est $1,072,677

      Not Listed For Sale

      34 Edward Dr, Winchester, MA 01890

      • 3 Beds
      • 3.5 Baths
      • 2,754 Sq Ft
      • Built 1985
      34 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 5 Forest Cir, Winchester, MA 01890
    5 Forest Cir, Winchester, MA 01890
    5 Forest Cir, Winchester, MA 01890
    /10

    $2,999,000

    • 4 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    5 Forest Cir, Winchester, MA 01890

    New construction currently underway. Estimated completion in approximately Spring/Summer 2027. Set on an impressive 22,629 sq. ft. lot, this beautifully crafted new construction offers exceptional space, thoughtful design, and a peaceful setting with easy access to the Middlesex Fells Reservation and I-93. Designed for today's lifestyle, the main level features a welcoming foyer, elegant living

    Pirani & Wile Group Gibson Sotheby's International Realty

    5 Forest Cir, Winchester, MA 01890
  • 21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    21 Fernway, 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 $2,969,905

    Last Listing Agent Kim Covino Compass

    21 Fernway, Winchester, MA 01890
    • 47 Edward Dr, Winchester, MA 01890
      47 Edward Dr, Winchester, MA 01890
      47 Edward Dr, Winchester, MA 01890
      /37

      Est $902,763

      Not Listed For Sale

      47 Edward Dr, Winchester, MA 01890

      • 2 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 1985
      47 Edward Dr, Winchester, MA 01890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  • 50 Middlesex St Unit 52, Winchester, MA 01890
    50 Middlesex St Unit 52, Winchester, MA 01890
    50 Middlesex St Unit 52, Winchester, MA 01890
    /21

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    50 Middlesex St Unit 52, Winchester, MA 01890

    Completely renovated from top to bottom, this brand-new 2-bedroom, 2-bath condo offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy white oak hardwood floors, a stunning chef's kitchen

    The North Star Group Keller Williams Realty Evolution

    50 Middlesex St Unit 52, Winchester, MA 01890
  • 171 Swanton St Unit 5, Winchester, MA 01890
    171 Swanton St Unit 5, Winchester, MA 01890
    171 Swanton St Unit 5, 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 $923,879

    Last Listing Agent Jonathan Radford Coldwell Banker Realty - Boston

    171 Swanton St Unit 5, Winchester, MA 01890
    • 25 Henry St, Winchester, MA 01890
      25 Henry St, Winchester, MA 01890
      25 Henry St, Winchester, MA 01890
      /42

      Est $921,607

      Not Listed For Sale

      25 Henry St, Winchester, MA 01890

      • 5 Beds
      • 4.5 Baths
      • 3,890 Sq Ft
      • Built 2021
      25 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Karima Alami Compass

  • 666 Main St Unit 207, Winchester, MA 01890
    666 Main St Unit 207, Winchester, MA 01890
    666 Main St Unit 207, Winchester, MA 01890
    /27

    $829,000

    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    666 Main St Unit 207, Winchester, MA 01890

    Sunlit, pristine and perfectly located in the center of town ! This second floor unit features a fully renovated white kitchen (2019) with new appliances, seamlessly flowing into an open, inviting living space. Step directly out onto your private roof deck overlooking tranquil views of Wedge Pond...the ultimate spot for morning coffee or evening relaxing. The two bedroom, two bath unit also

    Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

    666 Main St Unit 207, Winchester, MA 01890
  • 17 Charles Rd Unit 17, Winchester, MA 01890
    17 Charles Rd Unit 17, Winchester, MA 01890
    17 Charles Rd Unit 17, 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 $646,725

    Last Listing Agent Jessica Later JL+CoRE

    17 Charles Rd Unit 17, Winchester, MA 01890
    • 28 Henry St, Winchester, MA 01890
      28 Henry St, Winchester, MA 01890
      28 Henry St, Winchester, MA 01890
      /26

      Est $856,301

      Not Listed For Sale

      28 Henry St, Winchester, MA 01890

      • 2 Beds
      • 1 Bath
      • 1,279 Sq Ft
      • Built 1942
      28 Henry St, Winchester, MA 01890

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Alison Socha Leading Edge Real Estate

  • 22 Arthur St, Winchester, MA 01890
    22 Arthur St, Winchester, MA 01890
    22 Arthur St, Winchester, MA 01890
    /13

    $414,500

    Pending
    • 2 Beds
    • 1 Bath
    • 1,121 Sq Ft

    22 Arthur St, Winchester, MA 01890

    This property is available to and priced for Income Eligible families in 100% of the moderate-income range. See attached application for eligibility requirements. Throughout the tenure of the current homeowner many upgrades have been made to this property. Roof, new porch, updated Electrical, kitchen cabinets, Gas furnace, DE leading, new brick chimney. The exterior of the home is being prepped

    Karen Morand MCO Realty Service, LLC

    22 Arthur St, Winchester, MA 01890

Showing Results 121 - 160, Page 4 of 18

Massachusetts Middlesex County

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group