9,202

Winchester, MA Homes

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  • 11 Fieldstone Dr, Winchester, MA 01890
    11 Fieldstone Dr, Winchester, MA 01890
    11 Fieldstone Dr, Winchester, MA 01890
    /41

    $2,899,000

    • 5 Beds
    • 4.5 Baths
    • 6,904 Sq Ft

    11 Fieldstone Dr, Winchester, MA 01890

    Stunning 5BD/4.5BA contemporary estate on a private cul-de-sac in Winchester’s most coveted neighborhood. Modern design with soaring two-story ceilings, skylights, wide-plank hardwoods, and a dramatic stone fireplace. Gourmet chef’s kitchen with all-white waterfall island, Sub-Zero appliances, and butler’s pantry. Luxe primary suite with dual walk-in closet, spa bath, and private terrace. Fully

    Andersen Group Realty Keller Williams Realty Boston Northwest

    11 Fieldstone Dr, Winchester, MA 01890
  • 200 Swanton St Unit 239, Winchester, MA 01890
    200 Swanton St Unit 239, Winchester, MA 01890
    200 Swanton St Unit 239, Winchester, MA 01890
    /13

    $2,680 per month

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

    200 Swanton St Unit 239, Winchester, MA 01890

    HEAT, HOT WATER, AC and ELECTRIC included. Enjoy scenic pond views from this beautifully updated second-floor condo, perfectly situated overlooking the pond. This two-bedroom unit features an inviting open-concept layout that flows seamlessly onto a spacious private balcony—ideal for relaxing or entertaining outdoors. Generous closet space is found throughout the home, with additional storage

    Agent Photo

    Joan Powell

    Advisors Living - Merrimac

    (781) 818-0292

    200 Swanton St Unit 239, Winchester, MA 01890
  • 48 Tremont St, Winchester, MA 01890
    48 Tremont St, Winchester, MA 01890
    48 Tremont St, Winchester, MA 01890
    /15

    $930,000 Sold Jun 20, 2025

    • 2,333 Sq Ft
    • $399/SF
    • 25 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1959

    48 Tremont St, Winchester, MA 01890

    Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom with laundry, front-to-back fire-placed living

    Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

    48 Tremont St, Winchester, MA 01890
    • 38 Winthrop Street Extension, Winchester, MA 01890
      38 Winthrop Street Extension, Winchester, MA 01890
      38 Winthrop Street Extension, Winchester, MA 01890
      /39

      Est $2,304,324 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 4,539 Sq Ft

      38 Winthrop Street Extension, Winchester, MA 01890

      38 Winthrop Street Extension, Winchester, MA 01890
  • 8 Chestnut St, Winchester, MA 01890
    8 Chestnut St, Winchester, MA 01890
    8 Chestnut St, Winchester, MA 01890
    /42

    $2,890,000

    • 5 Beds
    • 6 Baths
    • 5,354 Sq Ft

    8 Chestnut St, Winchester, MA 01890

    Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and

    The McLaren D'Agostino Team Compass

    8 Chestnut St, Winchester, MA 01890
  • 25-35 River St, Winchester, MA 01890
    25-35 River St, Winchester, MA 01890
    25-35 River St, Winchester, MA 01890
    /24

    $3,275 - $4,845 per month

    Sanctuary Winchester North

    1-3 Beds

    25-35 River St, Winchester, MA 01890

    The Sanctuary at Winchester North is designed for the way you live - casual fireside gatherings in the Den, a game of billiards in the Hive, a meal with friends prepared in the Nest's Chef's Kitchen. Maybe you prefer to make a splash in the pool, or stay on track with personal health goals in the fitness and health facility. With meticulously appointed common spaces designed for work, play, and

    25-35 River St, Winchester, MA 01890
  • 44 Forest St, Winchester, MA 01890
    44 Forest St, Winchester, MA 01890
    44 Forest St, Winchester, MA 01890
    /42

    $1,187,000 Sold Jun 18, 2025

    • 1,906 Sq Ft
    • $623/SF
    • 12 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1926

    44 Forest St, Winchester, MA 01890

    This charming home is move-in ready with many updates throughout, situated on a large fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living

    Kim Covino Compass

    44 Forest St, Winchester, MA 01890
    • 20 Graystone Cir Unit 20, Winchester, MA 01890
      20 Graystone Cir Unit 20, Winchester, MA 01890
      20 Graystone Cir Unit 20, Winchester, MA 01890
      /33

      Est $1,745,337 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,254 Sq Ft

      20 Graystone Cir Unit 20, Winchester, MA 01890

      20 Graystone Cir Unit 20, Winchester, MA 01890
  • 4 Worthen Rd, Winchester, MA 01890
    4 Worthen Rd, Winchester, MA 01890
    4 Worthen Rd, Winchester, MA 01890
    /40

    $1,999,000 Open Sun 11:30AM - 1PM

    • 5 Beds
    • 3.5 Baths
    • 3,874 Sq Ft

    4 Worthen Rd, Winchester, MA 01890

    Must see! Sprawling 5 bed 3.5 bath customized colonial situated on a gorgeous street with 1/2 acre lot! This sun-drenched home is filled w/ natural light & is perfectly designed for both everyday living & entertaining. The first floor features a spacious, updated kitchen w/ an oversized island, dining room w fplc & two beautiful great rooms on either side of the home w/ vaulted ceilings,

    Kim Covino Compass

    4 Worthen Rd, Winchester, MA 01890
  • 29 Harvard St Unit 1, Winchester, MA 01890
    29 Harvard St Unit 1, Winchester, MA 01890
    29 Harvard St Unit 1, Winchester, MA 01890
    /25

    $2,550 per month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Apartment for Rent

    29 Harvard St Unit 1, Winchester, MA 01890

    Don’t miss this charming rental located in a desirable Winchester neighborhood! This unit features three spacious rooms and one full bathroom, offering comfortable and convenient living. Perfect for professionals or anyone seeking a quiet, well-situated home close to shops, dining, and public transportation. Pet friendly, recently updated with off street parking available. Kitchen boasts

    Prestige Homes Realty Team Prestige Homes Real Estate, LLC

    29 Harvard St Unit 1, Winchester, MA 01890
  • 18 Englewood Rd, Winchester, MA 01890
    18 Englewood Rd, Winchester, MA 01890
    18 Englewood Rd, Winchester, MA 01890
    /35

    $1,750,000 Sold Jun 17, 2025

    • 2,597 Sq Ft
    • $674/SF
    • 2 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1925

    18 Englewood Rd, Winchester, MA 01890

    OFFER ACCEPTED - Open Houses CANCELED This stunning, sun-filled home welcomes you with a front porch facing southwest for sunset views! Move right in and enjoy so many updates - new windows, new kitchen, new shared bath, new heating and cooling systems, new exercise/mudroom, new landscaping and so much more!!! With fabulous detail and a focus on energy efficiency, this home will win your heart

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    18 Englewood Rd, Winchester, MA 01890
    • 15 Vinson Cir, Winchester, MA 01890
      15 Vinson Cir, Winchester, MA 01890
      15 Vinson Cir, Winchester, MA 01890
      /41

      Est $2,846,171 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,662 Sq Ft

      15 Vinson Cir, Winchester, MA 01890

      15 Vinson Cir, Winchester, MA 01890
  • 4 Fieldstone Dr, Winchester, MA 01890
    4 Fieldstone Dr, Winchester, MA 01890
    4 Fieldstone Dr, Winchester, MA 01890
    /41

    $2,190,000 Open Sun 1:30PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 4,378 Sq Ft

    4 Fieldstone Dr, Winchester, MA 01890

    Nestled in a desirable Westside neighborhood, this stunning California contemporary/colonial home sits on a quiet cul-de-sac and offers 5 bedrooms, 3.5 baths, and over 20,000 sq ft of beautifully landscaped grounds. The sun-drenched interior features an open-concept kitchen and dining room with five fully opening doors leading to a bright four-seasons sunroom—perfect for gatherings year-round.

    Wenli Zheng Fairview Partners International LLC

    4 Fieldstone Dr, Winchester, MA 01890
  • 416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    416 Cambridge St, Winchester, MA 01890
    /20

    $2,650 - $5,780 per month

    Sanctuary Winchester West

    Studio-3 Beds

    416 Cambridge St, Winchester, MA 01890

    The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

    416 Cambridge St, Winchester, MA 01890
  • 19 Yale St, Winchester, MA 01890
    19 Yale St, Winchester, MA 01890
    19 Yale St, Winchester, MA 01890
    /42

    $2,350,000 Sold Jun 16, 2025

    • 4,212 Sq Ft
    • $558/SF
    • 15 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1880

    19 Yale St, Winchester, MA 01890

    Welcome to the Flats, where elegance and charm abound, the neighborhood is the one everyone aspires to. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom

    Nancy Pallotta Advisors Living - Winchester

    19 Yale St, Winchester, MA 01890
    • 228 Ridge St, Winchester, MA 01890
      228 Ridge St, Winchester, MA 01890
      228 Ridge St, Winchester, MA 01890
      /42

      Est $2,827,214 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 6,265 Sq Ft

      228 Ridge St, Winchester, MA 01890

      228 Ridge St, Winchester, MA 01890
  • 58 Bacon St, Winchester, MA 01890
    58 Bacon St, Winchester, MA 01890
    58 Bacon St, Winchester, MA 01890
    /40

    $2,295,000 Open Sun 12PM - 1:30PM

    • 6 Beds
    • 5.5 Baths
    • 5,791 Sq Ft

    58 Bacon St, Winchester, MA 01890

    Timeless elegance & contemporary comfort span four meticulously finished levels.This stately residence boasts 15 rooms, including six bedrooms and five-and-a-half bathrooms(2 en-suite). An inviting living room, anchored by a distinguished fireplace, flows seamlessly into an adjacent sunroom, offering a perfect retreat. The formal dining room opens to a covered porch, complete with a gas line for

    Real Estate Advisors Group Coldwell Banker Realty - Belmont

    58 Bacon St, Winchester, MA 01890
  • 29 Vine St Unit 3, Winchester, MA 01890
    29 Vine St Unit 3, Winchester, MA 01890
    29 Vine St Unit 3, Winchester, MA 01890
    /13

    $3,200 per month

    • 2 Beds
    • 1.5 Baths
    • 1,331 Sq Ft
    • Condo for Rent

    29 Vine St Unit 3, Winchester, MA 01890

    Two-level apartment with two bedrooms, two baths, and a parking space. Possible second parking space - negotiable. Large kitchen space with stainless steel appliances. Spacious off-living room, fenced porch. In-unit laundry. Walk-in closet. Dream location: t-station, shops, bike path, cafes, and much more, all within a 5-minute walk. Beautiful views of the Fells. First month and security deposit.

    Jasmina Cesic Danehy Realty Corp.

    29 Vine St Unit 3, Winchester, MA 01890
  • 7 Conant Rd Unit 34, Winchester, MA 01890
    7 Conant Rd Unit 34, Winchester, MA 01890
    7 Conant Rd Unit 34, Winchester, MA 01890
    /36

    $749,900 Sold Jun 13, 2025

    • 1,545 Sq Ft
    • $485/SF
    • 8 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1999

    7 Conant Rd Unit 34, Winchester, MA 01890

    Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step-free front entrance—an ideal setup for everyday convenience. This beautifully maintained first-floor unit offers the perfect blend of comfort, style, and accessibility. Inside, you'll find two generously sized bedrooms, including a spacious en-suite with direct access to one of

    Melanie Lentini Leading Edge Real Estate

    7 Conant Rd Unit 34, Winchester, MA 01890
    • 15 Wincrest Dr, Winchester, MA 01890
      15 Wincrest Dr, Winchester, MA 01890
      15 Wincrest Dr, Winchester, MA 01890
      /40

      Est $1,375,039 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,529 Sq Ft

      15 Wincrest Dr, Winchester, MA 01890

      15 Wincrest Dr, Winchester, MA 01890
  • 6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    /35

    $2,499,000 Open Sun 1:30PM - 3PM

    • 6 Beds
    • 5 Baths
    • 3,728 Sq Ft

    6 Ivy Cir, Winchester, MA 01890

    Stunning new construction Colonial tucked away at the end of a quiet cul-de-sac in "The Flats", offering the ideal combination of luxury, comfort, and convenience. Just minutes from Winchester Center, this beautifully crafted home places top-rated schools, boutique shopping, and vibrant dining right at your doorstep. Meticulously designed with high-end finishes throughout. Features include an

    Monte Marrocco Coldwell Banker Realty - Lexington

    6 Ivy Cir, Winchester, MA 01890
  • 2 Elmwood Ave Unit 1, Winchester, MA 01890
    2 Elmwood Ave Unit 1, Winchester, MA 01890
    2 Elmwood Ave Unit 1, Winchester, MA 01890
    /7

    $2,050 per month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 1, Winchester, MA 01890

    This nice 1 Bed 1 Bath place in the WINCHESTER area is available for Now. Included Features are: Laundry in Basement.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions

    2 Elmwood Ave Unit 1, Winchester, MA 01890
  • 21 Sheffield W, Winchester, MA 01890
    21 Sheffield W, Winchester, MA 01890
    21 Sheffield W, Winchester, MA 01890
    /40

    $3,025,000 Sold Jun 13, 2025

    • 5,198 Sq Ft
    • $582/SF
    • 50 Days On Market
    • 6 Beds
    • 5 Baths
    • Built 1910

    21 Sheffield W, Winchester, MA 01890

    Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of

    Kim Covino Compass

    21 Sheffield W, Winchester, MA 01890
    • 10 Carriage Ln, Winchester, MA 01890
      10 Carriage Ln, Winchester, MA 01890
      10 Carriage Ln, Winchester, MA 01890
      /33

      Est $1,506,725 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,034 Sq Ft

      10 Carriage Ln, Winchester, MA 01890

      10 Carriage Ln, Winchester, MA 01890
  • 1 Fox Hunt Ln, Winchester, MA 01890
    1 Fox Hunt Ln, Winchester, MA 01890
    1 Fox Hunt Ln, Winchester, MA 01890
    /41

    $2,250,000 Open Sun 2PM - 3:30PM

    • 5 Beds
    • 5 Baths
    • 5,000 Sq Ft

    1 Fox Hunt Ln, Winchester, MA 01890

    Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lot on a quiet cul-de-sac near Winchester Country Club. The first floor features a welcoming formal living room just off the entry, a spacious primary suite with two walk-in closets and a private bath, a guest bedroom with en-suite bath, and a third bedroom or home office.

    Leigh Ventura Compass

    1 Fox Hunt Ln, Winchester, MA 01890
  • 247 Washington St Unit 13, Winchester, MA 01890
    247 Washington St Unit 13, Winchester, MA 01890
    247 Washington St Unit 13, Winchester, MA 01890
    /13

    $3,000 per month

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft
    • Apartment for Rent

    247 Washington St Unit 13, Winchester, MA 01890

    Tucked away in the rear of the complex and facing a peaceful courtyard, this sparkling clean 2-bedroom, 1-bath unit offers the perfect blend of comfort, convenience, and charm. Accessible via a quiet side street, this home is ideal for anyone looking for tranquility without sacrificing location. Open-concept first floor with a non-working fireplace. Bonus loft space for a home office. Private

    Brooke Zarbano Regatta Realty

    247 Washington St Unit 13, Winchester, MA 01890
  • 65 Thornberry Rd, Winchester, MA 01890
    65 Thornberry Rd, Winchester, MA 01890
    65 Thornberry Rd, Winchester, MA 01890
    /37

    $1,535,000 Sold Jun 12, 2025

    • 2,525 Sq Ft
    • $608/SF
    • 5 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1965

    65 Thornberry Rd, Winchester, MA 01890

    Beautifully updated 4-bed, 2.5-bath ranch on a landscaped half-acre lot with attached 2-car garage. Enjoy single-level living with an open floor plan, cathedral-ceiling kitchen with granite counters, island seating, and stainless appliances. Living and dining areas flow seamlessly; cozy family room with fireplace. Sunroom with wall of windows overlooks the expansive backyard. Primary suite

    Hongmei Wang HMW Real Estate, LLC

    65 Thornberry Rd, Winchester, MA 01890
    • 16 Carriage Ln, Winchester, MA 01890
      16 Carriage Ln, Winchester, MA 01890
      16 Carriage Ln, Winchester, MA 01890
      /33

      Est $1,467,161 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,968 Sq Ft

      16 Carriage Ln, Winchester, MA 01890

      16 Carriage Ln, Winchester, MA 01890
  • 107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    /42

    $2,599,000

    • 6 Beds
    • 4.5 Baths
    • 5,824 Sq Ft

    107 Cambridge St, Winchester, MA 01890

    Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern updates. Rich with sumptuous period details and soaring 9' ceilings, the inviting first floor features a grand marble foyer with custom built-ins and a sweeping staircase. The formal living room offers a stately fireplace, while the chef’s kitchen—complete with expansive quartz

    Maija Sawyer Puleo William Raveis R.E. & Home Services

    107 Cambridge St, Winchester, MA 01890
  • 200 Swanton St, Winchester, MA 01890
    200 Swanton St, Winchester, MA 01890
    200 Swanton St, Winchester, MA 01890
    /10

    $2,680 per month

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

    200 Swanton St, Winchester, MA 01890

    HEAT, HOT WATER, AC and ELECTRIC included. Enjoy scenic pond views from this beautifully updated second-floor condo, perfectly situated overlooking the pond. This two-bedroom unit features an inviting open-concept layout that flows seamlessly onto a spacious private balcony—ideal for relaxing or entertaining outdoors. Generous closet space is found throughout the home, with additional storage

    200 Swanton St, Winchester, MA 01890
  • 7 Hutchinson Rd, Winchester, MA 01890
    7 Hutchinson Rd, Winchester, MA 01890
    7 Hutchinson Rd, Winchester, MA 01890
    /40

    $1,510,000 Sold Jun 09, 2025

    • 3,406 Sq Ft
    • $443/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1959

    7 Hutchinson Rd, Winchester, MA 01890

    A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a generous lot, this unique home has been lovingly maintained and is full of potential; ready for updates & your personal touch! The floor plan provides a flexible layout that’s ideal for easy living with a spacious first-floor bedroom, full bath, an oversized home office or add'l

    Kim Covino Compass

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

      Est $1,468,020 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,125 Sq Ft

      47 Thornberry Rd, Winchester, MA 01890

      47 Thornberry Rd, Winchester, MA 01890
  • 162 Swanton St Unit 162, Winchester, MA 01890
    162 Swanton St Unit 162, Winchester, MA 01890
    162 Swanton St Unit 162, Winchester, MA 01890
    /32

    $1,299,000 Open Sun 11AM - 12PM

    • 3 Beds
    • 3.5 Baths
    • 2,136 Sq Ft

    162 Swanton St Unit 162, Winchester, MA 01890

    Opportunity to own the last available end unit! Welcome to 162 Swanton Street, the final new construction townhome by Ron Roy in the heart of Winchester. This home blends modern design with exceptional craftsmanship. The open-concept first floor features hardwood floors, a cozy fireplace, and a chef-inspired kitchen with stainless steel appliances, a large island, and adjacent mudroom with half

    Monte Marrocco Coldwell Banker Realty - Lexington

    162 Swanton St Unit 162, Winchester, MA 01890
  • 846 Main St Unit III, Winchester, MA 01890
    846 Main St Unit III, Winchester, MA 01890
    846 Main St Unit III, Winchester, MA 01890
    /35

    $7,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,900 Sq Ft
    • Apartment for Rent

    846 Main St Unit III, Winchester, MA 01890

    No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

    Anthony Marino The Marino Group Collection

    846 Main St Unit III, Winchester, MA 01890
  • 10 Allen Rd, Winchester, MA 01890
    10 Allen Rd, Winchester, MA 01890
    10 Allen Rd, Winchester, MA 01890
    /23

    $1,182,000 Sold Jun 09, 2025

    • 1,520 Sq Ft
    • $778/SF
    • 24 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1929

    10 Allen Rd, Winchester, MA 01890

    Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the

    Sally Baldwin Coldwell Banker Realty - Lexington

    10 Allen Rd, Winchester, MA 01890
    • 16 Nassau Dr, Winchester, MA 01890
      16 Nassau Dr, Winchester, MA 01890
      16 Nassau Dr, Winchester, MA 01890
      /35

      Est $1,637,803 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,926 Sq Ft

      16 Nassau Dr, Winchester, MA 01890

      16 Nassau Dr, Winchester, MA 01890
  • 9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    /40

    $2,299,000

    • 6 Beds
    • 3.5 Baths
    • 4,667 Sq Ft

    9 Prospect St, Winchester, MA 01890

    Step into timeless elegance with this Colonial Revival, a true celebration of classic architecture, refined style, and exceptional craftsmanship. From the moment you arrive, the home's rich character makes a striking first impression, setting the stage for everything that follows. Inside, you’ll discover a harmonious blend of historic charm and modern comfort. Gleaming hardwood floors, intricate

    Nancy Pallotta Advisors Living - Winchester

    9 Prospect St, Winchester, MA 01890
  • 200 Swanton St Unit 331, Winchester, MA 01890
    200 Swanton St Unit 331, Winchester, MA 01890
    200 Swanton St Unit 331, Winchester, MA 01890
    /14

    $2,100 per month

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

    200 Swanton St Unit 331, Winchester, MA 01890

    NO BROKER FEE!Be in the heart of Winchester and minutes from downtown Boston by train!A FULL SIZE 1-BEDROOM apartment (for rent in Winchester in the most convenient location! Walk to the T Train Station, walk to Stop & Shop. Beautiful downtown Winchester just steps away. Rent includes ALL the utilities, including heat, water, hot water, central A/C, and EVEN ELECTRICITY! One parking

    200 Swanton St Unit 331, Winchester, MA 01890
  • 45 Brooks St, Winchester, MA 01890
    45 Brooks St, Winchester, MA 01890
    45 Brooks St, Winchester, MA 01890
    /41

    $2,850,000 Sold Jun 09, 2025

    • 4,325 Sq Ft
    • $659/SF
    • 8 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1953

    45 Brooks St, Winchester, MA 01890

    Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300+ sf 4BD 4 BA home offering a classic exterior with a stunning "must see" interior; featuring formal spaces great for entertaining blended w/casual living areas both inside & out w/ walls of floor to ceiling windows capturing the elements of

    Kim Covino Compass

    45 Brooks St, Winchester, MA 01890
    • 94 Johnson Rd, Winchester, MA 01890
      94 Johnson Rd, Winchester, MA 01890
      94 Johnson Rd, Winchester, MA 01890
      /36

      Est $1,592,138 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,171 Sq Ft

      94 Johnson Rd, Winchester, MA 01890

      94 Johnson Rd, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18

Massachusetts Winchester

Real Estate & Homes

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 23 days on the market compared to the national average of 50 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,558,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,558,000
Median Single Family Sale Price
$1,900,000
Median Townhouse Sale Price
$1,450,000
Median 2 Bedroom Sale Price
$732,500
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$549
Number of Homes for Sale
49
Last 12 months Home Sales
227
Months of Supply
2.60
Median List Price
$1,649,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
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