9,202

Winchester, MA Homes

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  • /42

    $3,175,000

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

    21 Fernway, Winchester, MA 01890

    Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mature landscape. This stately residence offers a true private oasis just minutes from all conveniences. Rich in finish, elegant in design w/ stunning living areas, large scale rooms & 4 fireplaces creating warm inviting spaces for every day

    Kim Covino Compass

    21 Fernway, Winchester, MA 01890
  • /36

    $7,000 per month

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

    846 Main St Unit IV, 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 IV, Winchester, MA 01890
  • /19

    $690,000 Sold Jun 06, 2025

    • 1,634 Sq Ft
    • $422/SF
    • 20 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1999

    7 Conant Rd Unit 60, Winchester, MA 01890

    OPEN HOUSE Sunday, May 18: 1-3:30PM. Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and 2.5 baths, making it one of the larger units in the complex. It features many modern amenities such as hardwood floors in the living area, three balconies, in-unit washer/dryer, gas fireplace, and

    Irene Novia Loka Matahari Real Estate LLC

    7 Conant Rd Unit 60, Winchester, MA 01890
    • /32

      Est $1,635,493 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,622 Sq Ft

      104 Thornberry Rd, Winchester, MA 01890

      104 Thornberry Rd, Winchester, MA 01890
  • /40

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

    • 6 Beds
    • 3.5 Baths
    • 4,696 Sq Ft

    5 Squire Rd, Winchester, MA 01890

    Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

    Alina Wang Coldwell Banker Realty - Lexington

    5 Squire Rd, Winchester, MA 01890
  • /11

    $1,895 per month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    75 Church St Unit R, Winchester, MA 01890

    1 bed and 1 bath located in Winchester. Easy access to downtown and public transportation!

    75 Church St Unit R, Winchester, MA 01890
  • /33

    $1,650,000 Sold Jun 06, 2025

    • 3,338 Sq Ft
    • $494/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1980

    34 Coolidge Rd, Winchester, MA 01890

    A chance to update and create your personal design that is located in Winchester's sought after Vinson Owen School district. Set on a impressive massive manicured corner lot that has been maintained since it has been custom built by its original owners. Scenic backyard with a patio off the kitchen that spills on a large private backyard that has an inground pool. Set the stage with a large foyer

    Pauline Marino Coldwell Banker Realty - Lexington

    34 Coolidge Rd, Winchester, MA 01890
    • /34

      Est $2,061,007 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,000 Sq Ft

      133 Johnson Rd, Winchester, MA 01890

      133 Johnson Rd, Winchester, MA 01890
  • /26

    $2,249,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 4,023 Sq Ft

    19 Sussex Rd, Winchester, MA 01890

    Ideally located in a very desirable neighborhood that abuts the town forest and surrounded by cul-de-sacs, this elegant well-designed 4-bedroom, 3.5-bathroom colonial home has been meticulously maintained by the original owners and features a spacious layout with ample room for comfortable living. The floorplan is thoughtfully designed, with a nice flow from one room to the next. The family room

    Ida Bianco Coldwell Banker Realty - Lexington

    19 Sussex Rd, Winchester, MA 01890
  • /41

    $9,800 per month

    • 5 Beds
    • 4.5 Baths
    • 5,016 Sq Ft
    • House for Rent

    22 Amberwood Dr, Winchester, MA 01890

    Fabulous rental opportunity with full wing of an additional in-law suite for multi-generational living at its best. Beautiful designers’ grade high-end finishes throughout! Features separate side entry with inviting south-facing covered porch, a dramatic two-story foyer/ceiling, and the main kitchen that flows into an additional meal prep kitchen area with integrated appliances – Thermador

    Anita Lin Coldwell Banker Realty - Lexington

    22 Amberwood Dr, Winchester, MA 01890
  • /38

    $1,475,000 Sold Jun 05, 2025

    • 2,897 Sq Ft
    • $509/SF
    • 15 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1934

    195 Mystic Valley Pkwy, Winchester, MA 01890

    Lovely brick home just up the road from EVERYTHING!!! Commuter Rail, Library, Schools, Shopping, Restaurants, Town Hall. Less than 9 miles to Boston! So close to the Middlesex Fells and the Tri-Community Greenway. Location, location, location - CHECK! Now the structure...classic brick home built to stand the test of time with BIG IMPROVEMENTS. Grand front to back living room with fireplace leads

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    195 Mystic Valley Pkwy, Winchester, MA 01890
    • /39

      Est $1,901,005 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,046 Sq Ft

      73 Thornberry Rd, Winchester, MA 01890

      73 Thornberry Rd, Winchester, MA 01890
  • /38

    $1,899,000 Pending

    • 4 Beds
    • 4 Baths
    • 4,195 Sq Ft

    5 Hastings Rd, Winchester, MA 01890

    Rare opportunity on a peaceful cul-de-sac. This extraordinary 4-bedroom, 4-bathroom home is nestled in one of Winchester's most sought-after neighborhoods. For the first time ever, this meticulously maintained residence is available on a street where properties rarely change hands. Bathed in abundant natural light, the thoughtfully designed floor plan showcases generously sized living spaces that

    Nancy Pallotta Advisors Living - Winchester

    5 Hastings Rd, Winchester, MA 01890
  • /33

    $4,200 per month

    • 4 Beds
    • 1.5 Baths
    • 1,300 Sq Ft
    • Townhouse for Rent

    848 Main St, Winchester, MA 01890

    **Elegant Winchester Home Near Wright Pond and Downtown Amenities**Spacious 4-bedroom, 1.5-bathroom townhouse style unit - located close to Winchester Center, with a park across the street and Wright Pond and Park nearby.Enjoy top rated Winchester schools nearby.Open-concept kitchen with granite countertops, island, pantry, and space for your table, plus hardwood floors, central

    848 Main St, Winchester, MA 01890
  • /42

    $2,111,000 Sold Jun 05, 2025

    • 4,744 Sq Ft
    • $445/SF
    • 6 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1922

    14 Grove St, Winchester, MA 01890

    Located just outside the town center near Brooks neighborhood & the train to Boston! This spacious home has it all! Situated on a lovely level lot w/ 2 car garage & private yard, this updated move in ready home boasts an abundance of space w/ideal layout & large sun drenched eat in kitchen with skylights & bay window, adjacent family room, living room w/ fplc, formal dining, office, laundry & 2

    Kim Covino Compass

    14 Grove St, Winchester, MA 01890
    • /35

      Est $1,800,712 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,224 Sq Ft

      22 Berkshire Dr, Winchester, MA 01890

      22 Berkshire Dr, Winchester, MA 01890
  • /35

    $1,249,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,157 Sq Ft

    63 Church St, Winchester, MA 01890

    Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with

    Nancy McLaughlin Redfin Corp.

    63 Church St, Winchester, MA 01890
  • /12

    $2,350 per month

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

    35 Vine St Unit 401, Winchester, MA 01890

    Immaculate, king-sized, 1 bedroom apartment on top floor of brick building just steps to Winchester Center and Commuter Rail. Heat and hot water included. Dishwasher /disposal, over-the-stove microwave, newly carpeted, central A/C and 1 car, assigned garage parking spot with automatic door opener. Laundry in building. Storage unit included. Available now or July-September 1st. No pets/no

    Jill Shanley CJL Rentals & Property Management Co., Inc.

    35 Vine St Unit 401, Winchester, MA 01890
  • /11

    $1,269,000 Sold Jun 04, 2025

    • 2,136 Sq Ft
    • $594/SF
    • 1 Day On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2025

    158 Swanton St Unit 160, Winchester, MA 01890

    Welcome to 158 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

    Monte Marrocco Coldwell Banker Realty - Lexington

    158 Swanton St Unit 160, Winchester, MA 01890
    • /42

      Est $2,281,368 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,620 Sq Ft

      5 Partridge Ln, Winchester, MA 01890

      5 Partridge Ln, Winchester, MA 01890
  • /37

    $1,950,000 Pending

    • 6 Beds
    • 3.5 Baths
    • 3,901 Sq Ft

    20 Elm St, Winchester, MA 01890

    Nestled in the highly sought-after "heart" of Winchester Center, this Newer Construction single-family (slightly attached) home offers space & finishes you typically find in 2.5M+ homes! With 10' ceilings and high end finishes throughout, this stunning 5-6 bedroom, 3.5 bath home is just two blocks from the vibrant town center, train station, schools, restaurants & shops! 5190 total sf w/ 3900sf

    Kim Covino Compass

    20 Elm St, Winchester, MA 01890
  • /11

    $2,200 per month

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

    253 Swanton St Unit 428, Winchester, MA 01890

    1 bed and 1 bath located in Winchester Highlands. Easy access to downtown and public transportation!

    253 Swanton St Unit 428, Winchester, MA 01890
  • /24

    $1,084,000 Sold Jun 04, 2025

    • 2,290 Sq Ft
    • $473/SF
    • 30 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2025

    160 Swanton St Unit 160, Winchester, MA 01890

    Welcome to 160 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

    Monte Marrocco Coldwell Banker Realty - Lexington

    160 Swanton St Unit 160, Winchester, MA 01890
    • /40

      Est $2,114,254 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 4,532 Sq Ft

      89 Thornberry Rd, Winchester, MA 01890

      89 Thornberry Rd, Winchester, MA 01890
  • /40

    $1,899,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,813 Sq Ft

    20 Seneca Rd, Winchester, MA 01890

    Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious

    Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

    20 Seneca Rd, Winchester, MA 01890
  • /12

    $2,300 per month

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

    4 Border St Unit 4, Woburn, MA 01801

    Available Now! 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, Horn Pond and Major Highway access.

    Robin Griffiths J. Mulkerin Realty

    4 Border St Unit 4, Woburn, MA 01801
  • /26

    $1,140,000 Sold Jun 03, 2025

    • 1,646 Sq Ft
    • $693/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1955

    7 Indian Hill Rd, Winchester, MA 01890

    This inviting ranch house is cheerful and functional. Sunlight floods the open living and dining rooms, while custom plantation shutters offer privacy. Hardwood floors, a gas fireplace, and arched doorways add character and warmth to the space. The well-equipped kitchen features granite countertops, glass-front cabinetry and access to a side deck for al fresco dining. Three bright bedrooms and a

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

    7 Indian Hill Rd, Winchester, MA 01890
    • /11

      Est $1,318,281 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,218 Sq Ft

      233 High St, Winchester, MA 01890

      233 High St, Winchester, MA 01890
  • /39

    $1,999,000 Pending

    • 4 Beds
    • 4 Baths
    • 3,818 Sq Ft

    1 Saint Augustine Ct, Winchester, MA 01890

    Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total package. With 4 bedrooms, 3 baths, and gleaming hardwood floors throughout, it strikes the perfect balance between timeless charm and fresh, move-in-ready style. The front-to-back living room is flooded with natural light—ideal for everything from morning coffee to impromptu

    Nancy Pallotta Advisors Living - Winchester

    1 Saint Augustine Ct, Winchester, MA 01890
  • /14

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,452 Sq Ft
    • Apartment for Rent

    273 Cross St Unit 273, Winchester, MA 01890

    Available September 1, 2025! Don’t miss this charming and spacious 6-room duplex townhouse—ready for you to move right in! This well-maintained home features a bright and airy living room and formal dining area, perfect for relaxing or entertaining. The renovated kitchen boasts granite countertops, modern finishes, and a walk-out to your private fenced yard—ideal for seamless indoor-outdoor

    coldown jx Phoenix Real Estate Partners, LLC

    273 Cross St Unit 273, Winchester, MA 01890
  • /34

    $2,000,000 Sold Jun 02, 2025

    • 3,039 Sq Ft
    • $658/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1927

    11 Chesterford Rd E, Winchester, MA 01890

    Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly

    Joseph Pollack Redfin Corp.

    11 Chesterford Rd E, Winchester, MA 01890
    • /4

      Est $2,990,101 Not Listed For Sale

      • 6 Beds
      • 7 Baths
      • 6,500 Sq Ft

      136 Ridge St, Winchester, MA 01890

      136 Ridge St, Winchester, MA 01890
  • /42

    $1,849,000 Pending

    • 4 Beds
    • 5 Baths
    • 3,148 Sq Ft

    15 Kendall St, Winchester, MA 01890

    Explore this pristine newer construction, freshly updated home just outside the center!! Situated on a gorgeous level lot with slider to patio & expansive rear yard, this captivating home has an absolutely beautiful setting w/natural stone walls, raised planting beds w/flowering trees, perennials & a spectacular rose garden! Enjoy the lovely farmers porch & desirable layout w/sun-drenched kitchen

    Kim Covino Compass

    15 Kendall St, Winchester, MA 01890
  • /18

    $3,300 per month

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

    40 Florence St Unit 40, Winchester, MA 01890

    2-Bedroom apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this two-bedroom and one-bathroom in a two-family house setting has a nice floor plan and decent flow. Hardwood floor throughout. It has a spacious eat-in kitchen with a pantry and with stainless appliances, granite counter tops and a side door that leads to the big and bright backyard. Two bright

    Weidong Li WINN Real Estate & Consulting

    40 Florence St Unit 40, Winchester, MA 01890
  • /33

    $699,900 Sold May 30, 2025

    • 1,326 Sq Ft
    • $528/SF
    • 4 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1890

    32 Clark St, Winchester, MA 01890

    A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a home to their liking, this residence presents the perfect blend of potential and location. This 2 bedroom single family home makes for a great condo alternative. Don't miss this rare chance to break into the Winchester market and enjoy all this town has to offer from it's great

    Rodrigo Serrano Leading Edge Real Estate

    32 Clark St, Winchester, MA 01890
    • /36

      Est $1,371,405 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,823 Sq Ft

      7 Wainwright Rd Unit 88, Winchester, MA 01890

      7 Wainwright Rd Unit 88, Winchester, MA 01890
  • /42

    $2,250,000 Pending

    • 5 Beds
    • 3.5 Baths
    • 3,719 Sq Ft

    17 Harrison St, Winchester, MA 01890

    Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester’s beautiful Flats neighborhood. This meticulously renovated 5-bedroom home features a chef's kitchen with custom cabinetry, granite surfaces, center island, beverage cooler & built-in china cabinet. Natural light floods the expansive family room, featuring custom built-ins & oversized

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

    17 Harrison St, Winchester, MA 01890
  • /11

    $2,100 per month

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

    200 Swanton St Unit 428, Winchester, MA 01890

    Bright and sunny 1 bedroom and 1 bathroom condo in Winchester Park View. close to shopping, restaurants, town Center and walking to commuter train. Easy access to all major highways. Rental fee Including heat, electricity, hot water and a lot of more... Available 06/01.

    Wei Wang WW Real Estate LLC

    200 Swanton St Unit 428, Winchester, MA 01890
  • /42

    $1,350,000 Sold May 30, 2025

    • 3,351 Sq Ft
    • $403/SF
    • 38 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 1946

    34 Fells Rd, Winchester, MA 01890

    Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

    Andersen Group Realty Keller Williams Realty Boston Northwest

    34 Fells Rd, Winchester, MA 01890
    • /33

      Est $1,675,179 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,327 Sq Ft

      7 Wainwright Rd Unit 72, Winchester, MA 01890

      7 Wainwright Rd Unit 72, Winchester, MA 01890

Showing Results 41 - 80, Page 2 of 18

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