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Newest Homes for Sale in Winchester, MA

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  • 7 Viking Rd, Winchester, MA 01890
    7 Viking Rd, Winchester, MA 01890
    7 Viking Rd, Winchester, MA 01890
    /29

    $2,849,000

    • 5 Beds
    • 4.5 Baths
    • 5,058 Sq Ft

    7 Viking Rd, Winchester, MA 01890

    Tucked on a quiet cul-de-sac in the sought-after Vinson Owen school district, this completely renovated 5-bedroom, 4.5-bath Colonial offers an exceptional blend of comfort and elevated design. Massive columns in classic revival style create stunning curb appeal, offering a striking introduction to the transformation inside. A spectacular chef's kitchen anchors the main level, featuring an

    Andersen Group Realty Keller Williams Realty Boston Northwest

    7 Viking Rd, Winchester, MA 01890
  • 30 Farrow St, Winchester, MA 01890
    30 Farrow St, Winchester, MA 01890
    30 Farrow St, Winchester, MA 01890
    /35

    $1,699,000

    • 5 Beds
    • 3.5 Baths
    • 3,180 Sq Ft

    30 Farrow St, Winchester, MA 01890

    Built in 2019 and perfectly positioned near downtown Winchester and the commuter rail, this 5 bed, 3.5 bath Colonial offers a bright, open layout with oversized windows, newly installed custom interior shutters and great natural light throughout. The large living room flows into the dining room, making the first floor great for everyday living and entertaining. The kitchen features a 2025

    Carlisle Group Compass

    30 Farrow St, Winchester, MA 01890
  • 2 Stratton Dr Unit 41876298, Woburn, MA 01801
    2 Stratton Dr Unit 41876298, Woburn, MA 01801
    2 Stratton Dr Unit 41876298, Woburn, MA 01801
    /17

    $899,995

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,667 Sq Ft

    Ashford Plan at Highland at Vale - Richfield Collection, Woburn, MA 01801

    The spacious Ashford plan offers More Life Built In with a kitchen perfect for entertaining friends & family alike. A corner-unit location lets the natural light pour in through the many windows.

    Pulte Homes Builder
    2 Stratton Dr Unit 41876298, Woburn, MA 01801
  • 17 Russell Rd, Winchester, MA 01890
    17 Russell Rd, Winchester, MA 01890
    17 Russell Rd, Winchester, MA 01890
    /17

    $1,098,000

    • 3 Beds
    • 1.5 Baths
    • 1,657 Sq Ft

    17 Russell Rd, Winchester, MA 01890

    Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a

    KoKo Kwan Kwan Realty Inc.

    17 Russell Rd, Winchester, MA 01890
  • 85 High St, Winchester, MA 01890
    85 High St, Winchester, MA 01890
    85 High St, Winchester, MA 01890
    /38

    $1,999,000

    • 4 Beds
    • 2.5 Baths
    • 3,757 Sq Ft

    85 High St, Winchester, MA 01890

    Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a

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

    85 High St, Winchester, MA 01890
  • 10 Rangeley Rd, Winchester, MA 01890
    10 Rangeley Rd, Winchester, MA 01890
    10 Rangeley Rd, Winchester, MA 01890
    /42

    $3,199,000

    • 5 Beds
    • 4.5 Baths
    • 5,406 Sq Ft

    10 Rangeley Rd, Winchester, MA 01890

    Exceptionally rare property on prestigious Rangeley Road, steps to downtown Winchester. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Brand NEW Roof+HVAC. Grand, sun drenched

    Karima Alami Compass

    10 Rangeley Rd, Winchester, MA 01890
  • 23 Lantern Ln, Arlington, MA 02474
    23 Lantern Ln, Arlington, MA 02474
    23 Lantern Ln, Arlington, MA 02474
    /42

    $2,950,000

    • 6 Beds
    • 5.5 Baths
    • 5,550 Sq Ft

    23 Lantern Ln, Arlington, MA 02474

    Stunning new-construction home set on a winding hillside street in Arlington's sought-after Morningside neighborhood. Designed for flexible modern living, this 6-bedroom residence features a serene second-floor primary suite plus a complete first-floor suite with its own private entrance — a self-contained space offering exceptional versatility. Two dedicated offices, one on each level, make

    Plato Asadov Steve Bremis Realty Group

    23 Lantern Ln, Arlington, MA 02474
  • 2 Atherton Rd, Winchester, MA 01890
    2 Atherton Rd, Winchester, MA 01890
    2 Atherton Rd, Winchester, MA 01890
    /42

    $3,295,000

    • 6 Beds
    • 6.5 Baths
    • 6,100 Sq Ft

    2 Atherton Rd, Winchester, MA 01890

    Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an

    Peter Kasseris Serhant

    2 Atherton Rd, Winchester, MA 01890
  • 110 Thornberry Rd, Winchester, MA 01890
    110 Thornberry Rd, Winchester, MA 01890
    110 Thornberry Rd, Winchester, MA 01890
    /34

    $1,399,000

    $101K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,459 Sq Ft

    110 Thornberry Rd, Winchester, MA 01890

    110 Thornberry Road. Strong west side location near Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. An exceptional opportunity to establish roots in Winchester. 2021 Natural Gas Brute FT Floor Standing Boiler. Replacement windows. Central cooling. 200 amp electric. Updated Kitchen w Double oven. Prefinished hardwood floors. Therma-Tru French doors flow from the dining room to

    Mark Kiklis Kiklis Real Estate, LLC

    110 Thornberry Rd, Winchester, MA 01890
  • 96 Loring Ave, Winchester, MA 01890
    96 Loring Ave, Winchester, MA 01890
    96 Loring Ave, Winchester, MA 01890
    /29

    $949,999

    • 4 Beds
    • 2 Baths
    • 2,326 Sq Ft

    96 Loring Ave, Winchester, MA 01890

    Discover a rare opportunity to own a versatile ranch in sought-after Winchester, offering flexible living with a two-bedroom main level and a full two-bedroom in-law suite below. The gracious first floor welcomes you with gleaming hardwood floors and a handsome fireplace anchoring the living room. A generously proportioned dining room, complete with a classic built-in china cabinet, opens

    Agent Photo

    Jeremy Smith

    StartPoint Realty

    96 Loring Ave, Winchester, MA 01890
  • 54 Squire Rd, Winchester, MA 01890
    54 Squire Rd, Winchester, MA 01890
    54 Squire Rd, Winchester, MA 01890
    /42

    $2,499,000

    • 4 Beds
    • 4.5 Baths
    • 4,450 Sq Ft

    54 Squire Rd, Winchester, MA 01890

    Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with

    Anthony Marino The Marino Group Collection

    54 Squire Rd, Winchester, MA 01890
  • 18 Ridge St, Winchester, MA 01890
    18 Ridge St, Winchester, MA 01890
    18 Ridge St, Winchester, MA 01890
    /4

    $3,200,000

    • 5 Beds
    • 5.5 Baths
    • 5,295 Sq Ft

    18 Ridge St, Winchester, MA 01890

    Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort.

    Gayle Winters Compass

    18 Ridge St, Winchester, MA 01890
  • 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

    Situated on a generous18,000SF level lot! 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

    Kim Covino Compass

    7 Hutchinson Rd, Winchester, MA 01890
  • 148 Marble St Unit 404, Stoneham, MA 02180
    148 Marble St Unit 404, Stoneham, MA 02180
    148 Marble St Unit 404, Stoneham, MA 02180
    /34

    $420,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    148 Marble St Unit 404, Stoneham, MA 02180

    Exceptional opportunity for easy, single-level living in an elevator building at The Gates in Stoneham, just over the Winchester line. Welcome to 148 Marble Street, Unit 404, offering approximately 1,000 square feet of thoughtfully designed living space and a lifestyle of comfort and convenience. This inviting residence features a spacious bedroom with wall-to-wall closets and abundant natural

    Cheryl Pendenza REMAX Andrew Realty Services

    148 Marble St Unit 404, Stoneham, MA 02180
  • 5 Forest Cir, Winchester, MA 01890
    5 Forest Cir, Winchester, MA 01890
    5 Forest Cir, Winchester, MA 01890
    /10

    $2,999,000

    • 5 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
  • 7 Wainwright Rd Unit 113, Winchester, MA 01890
    7 Wainwright Rd Unit 113, Winchester, MA 01890
    7 Wainwright Rd Unit 113, Winchester, MA 01890
    /42

    $2,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    7 Wainwright Rd Unit 113, Winchester, MA 01890

    Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home

    Kim Covino Compass

    7 Wainwright Rd Unit 113, Winchester, MA 01890
  • 50 Holland St, Winchester, MA 01890
    50 Holland St, Winchester, MA 01890
    50 Holland St, Winchester, MA 01890
    /42

    $1,549,000

    • 3 Beds
    • 2.5 Baths
    • 2,640 Sq Ft

    50 Holland St, Winchester, MA 01890

    Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted

    Kim Covino Compass

    50 Holland St, Winchester, MA 01890
  • 11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    /36

    $3,600,000

    • 7 Beds
    • 7.5 Baths
    • 7,429 Sq Ft

    11 Viking Rd, Winchester, MA 01890

    Spectacular ground-up NEW construction estate on expansive, large level lot of 24,688sf, ready for move in, located on a quiet Winchester cul-de-sac. Newly completed, this exceptional residence spans more than 7,000 square feet across impeccably finished levels. Ideally positioned on a quiet cul-de-sac on over half an acre of land in one of Winchester’s most desirable locations, the home offers

    Valerie Post Engel & Volkers Boston

    11 Viking Rd, Winchester, MA 01890
  • 1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    /42

    $1,794,000

    $5K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,010 Sq Ft

    1 Town Way, Winchester, MA 01890

    Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing

    Philip Vita Compass

    1 Town Way, Winchester, MA 01890
  • 42 Wildwood St, Winchester, MA 01890
    42 Wildwood St, Winchester, MA 01890
    42 Wildwood St, Winchester, MA 01890
    /42

    $2,299,000

    • 7 Beds
    • 4.5 Baths
    • 4,930 Sq Ft

    42 Wildwood St, Winchester, MA 01890

    Exceptional craftsmanship defines this majestic home in The Flats, where beautifully-preserved architectural details blend seamlessly w/ modern livability. A showstopping foyer welcomes you w/ a sweeping staircase, exquisite millwork, graceful arched openings & leaded glass windows. You’ll find quarter-sawn oak floors, rich woodwork, generously scaled windows & impressive ceiling height

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

    42 Wildwood St, Winchester, MA 01890
  • 15 Clark St Unit 17, Winchester, MA 01890
    15 Clark St Unit 17, Winchester, MA 01890
    15 Clark St Unit 17, Winchester, MA 01890
    /22

    $849,000

    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    15 Clark St Unit 17, Winchester, MA 01890

    Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated

    Jeffrey Hsu Coldwell Banker Realty - Milton

    15 Clark St Unit 17, Winchester, MA 01890
  • 2 Stratton Dr Unit 104, Woburn, MA 01801
    2 Stratton Dr Unit 104, Woburn, MA 01801
    2 Stratton Dr Unit 104, Woburn, MA 01801
    /23

    $899,995

    • 2 Beds
    • 2 Baths
    • 1,667 Sq Ft

    2 Stratton Dr Unit 104, Woburn, MA 01801

    Luxury new construction—this is the final opportunity to own the former Model Home at Highland at Vale in Woburn! The Ashford corner residence is filled with natural light from expansive windows and offers a thoughtfully designed open-concept layout. The gourmet-inspired kitchen features stainless steel appliances, an oversized center island, and beautiful cabinetry that flows seamlessly into the

    Erin Sullivan Pulte Homes of New England

    2 Stratton Dr Unit 104, Woburn, MA 01801
  • 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

    $685,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    666 Main St Unit 211, Winchester, MA 01890

    NEW PRICE! 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

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    666 Main St Unit 211, Winchester, MA 01890
  • 15 Clark St Unit 15, Winchester, MA 01890
    15 Clark St Unit 15, Winchester, MA 01890
    15 Clark St Unit 15, Winchester, MA 01890
    /24

    $849,000

    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    15 Clark St Unit 15, Winchester, MA 01890

    Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated

    Jeffrey Hsu Coldwell Banker Realty - Milton

    15 Clark St Unit 15, Winchester, MA 01890
  • 151 Wright St, Arlington, MA 02474
    151 Wright St, Arlington, MA 02474
    151 Wright St, Arlington, MA 02474
    /30

    $899,000

    • 3 Beds
    • 1.5 Baths
    • 2,520 Sq Ft

    151 Wright St, Arlington, MA 02474

    Step back in time at 151 Wright Street, a true time capsule brimming with original charm and endless potential. Lovingly maintained over the years, this classic Cape offers a rare opportunity to own a home that has preserved its character while providing the perfect canvas for your personal vision. Featuring three bedrooms, one and a half bathrooms, specious living space, the home offers a

    AJ Arstamyan Coldwell Banker Realty - Boston

    151 Wright St, Arlington, MA 02474
  • 47 Water St, Winchester, MA 01890
    47 Water St, Winchester, MA 01890
    47 Water St, Winchester, MA 01890
    /30

    $950,000

    • 3 Beds
    • 1.5 Baths
    • 1,356 Sq Ft

    47 Water St, Winchester, MA 01890

    Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds

    The Mary Scimemi Team Leading Edge Real Estate

    47 Water St, Winchester, MA 01890
  • 247 Washington St Unit 11, Winchester, MA 01890
    247 Washington St Unit 11, Winchester, MA 01890
    247 Washington St Unit 11, Winchester, MA 01890
    /23

    $650,000

    $79K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,494 Sq Ft

    247 Washington St Unit 11, Winchester, MA 01890

    Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for

    Heejeong Joo Coldwell Banker Realty - Lexington

    247 Washington St Unit 11, Winchester, MA 01890
  • 200 Swanton St Unit L8, Winchester, MA 01890
    200 Swanton St Unit L8, Winchester, MA 01890
    200 Swanton St Unit L8, Winchester, MA 01890
    /28

    $288,750

    • 1 Bed
    • 1 Bath
    • 388 Sq Ft

    200 Swanton St Unit L8, Winchester, MA 01890

    Welcome to effortless living in the most desirable community of Winchester. This beautifully updated studio condominium at The Parkview Condominiums offers an exceptional opportunity to own the most affordable home in Winchester. Rarely offered sunny side lobby level. You'll find a thoughtfully renovated interior featuring a stunning new kitchen with white shaker cabinetry, gleaming quartz

    Stephen DeConto Cameron Real Estate Group

    200 Swanton St Unit L8, Winchester, MA 01890
  • 10 Dartmouth St, Winchester, MA 01890
    10 Dartmouth St, Winchester, MA 01890
    10 Dartmouth St, Winchester, MA 01890
    /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
  • 79 Grove St, Winchester, MA 01890
    79 Grove St, Winchester, MA 01890
    79 Grove St, Winchester, MA 01890
    /41

    $1,899,000

    • 5 Beds
    • 3.5 Baths
    • 3,210 Sq Ft

    79 Grove St, Winchester, MA 01890

    As close to new construction as you’ll find, this exceptional Colonial was comprehensively renovated in 2016, with numerous additional improvements since. Sophisticated and comfortable, the home offers beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level features hardwood floors, elegant architectural details,

    Pirani & Wile Group Gibson Sotheby's International Realty

    79 Grove St, Winchester, MA 01890
  • 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

    $789,000

    $10K PRICE DROP
    • 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
  • 9 Plymouth Rd, Winchester, MA 01890
    9 Plymouth Rd, Winchester, MA 01890
    9 Plymouth Rd, Winchester, MA 01890
    /37

    $2,500,000

    • 5 Beds
    • 3 Baths
    • 4,071 Sq Ft

    9 Plymouth Rd, Winchester, MA 01890

    Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for

    Stephanie Crawford Real Broker MA, LLC

    9 Plymouth Rd, Winchester, MA 01890
  • 666 Main St Unit 315, Winchester, MA 01890
    666 Main St Unit 315, Winchester, MA 01890
    666 Main St Unit 315, Winchester, MA 01890
    /37

    $649,900

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft

    666 Main St Unit 315, Winchester, MA 01890

    Enjoy easy living at Wedgewood Place, a sought-after condominium community in the heart of Winchester Center. This spacious 2-bedroom, 2-bath home offers a bright, open layout with a wood-burning fireplace and a great balcony. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. The generous primary suite features

    Kim Covino Compass

    666 Main St Unit 315, Winchester, MA 01890
  • 22 Oldham Rd, Arlington, MA 02474
    22 Oldham Rd, Arlington, MA 02474
    22 Oldham Rd, Arlington, MA 02474
    /42

    $3,100,000

    • 5 Beds
    • 5.5 Baths
    • 5,600 Sq Ft

    22 Oldham Rd, Arlington, MA 02474

    Elegantly positioned in Arlington's desirable Morningside neighborhood, this custom build luxury colonial offers over 5600 sf of refined living space on a beautifully landscaped lot. This recently built home features 5 bedrooms,5 full and 1 half bath. A grand two-story living room filled with natural light creates a dramatic centerpiece, while the chef's kitchen is equipped with premium Thermador

    Kathleen Lyons Century 21 North East

    22 Oldham Rd, Arlington, MA 02474
  • 84 Oak St, Winchester, MA 01890
    84 Oak St, Winchester, MA 01890
    84 Oak St, Winchester, MA 01890
    /38

    $849,000

    $51K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,083 Sq Ft

    84 Oak St, Winchester, MA 01890

    Charming and Spacious Custom Built Mid-Century Bungalow offers a terrific opportunity to live in Winchester! Do you want to send your children to the award-winning public schools? Need an in-law apt.? Generously sized, sun-drenched, freshly painted rooms with high ceilings and hardwood floors, beautiful architectural details, and two fireplaces. A private, flat backyard perfect for growing

    John Magazzu Charlesgate Realty Group LLC

    84 Oak St, Winchester, MA 01890
  • 423 Washington St, Winchester, MA 01890
    423 Washington St, Winchester, MA 01890
    423 Washington St, Winchester, MA 01890
    /42

    $1,350,000

    • 4 Beds
    • 3 Baths
    • 2,690 Sq Ft

    423 Washington St, Winchester, MA 01890

    Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday

    Danielle Fleming MA Properties

    423 Washington St, Winchester, MA 01890
  • 258 Cross St, Winchester, MA 01890
    258 Cross St, Winchester, MA 01890
    258 Cross St, Winchester, MA 01890
    /39

    $999,900

    • 4 Beds
    • 2 Baths
    • 1,719 Sq Ft

    258 Cross St, Winchester, MA 01890

    A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth,

    Agent Photo

    Justin Blankenship

    Fiv Realty Co

    258 Cross St, Winchester, MA 01890
  • 269 Cambridge Rd Unit 608, Woburn, MA 01801
    269 Cambridge Rd Unit 608, Woburn, MA 01801
    269 Cambridge Rd Unit 608, Woburn, MA 01801
    /38

    $509,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 974 Sq Ft

    269 Cambridge Rd Unit 608, Woburn, MA 01801

    Enjoy stunning 6th-floor views from this bright and modern corner unit south east facing 2-bedroom, 2-bath condo in the sought-after Crescent Park community. Prime location just 1 minute from Whole Foods, 6 minutes to H Mart and Market Basket, and 10 minutes to Trader Joe’s and Burlington Mall, with convenient access to I-95 and the MBTA 350 bus to Alewife Station. This home offers abundant

    Rose Hall Blue Ocean Realty, LLC

    269 Cambridge Rd Unit 608, Woburn, MA 01801
  • 14 Cross St, Woburn, MA 01801
    14 Cross St, Woburn, MA 01801
    14 Cross St, Woburn, MA 01801
    /12

    $789,000

    $40K PRICE DROP
    • Land
    • 19,166 Sq Ft
    • $1,793,182 per Acre

    14 Cross St, Woburn, MA 01801

    Improved Land Opportunity - Developers, Contractors, Investors and Future single-family homeowners – recently reconfigured 14 Cross Street located immediately over the WINCHESTER line is an attractive sized residential lot consisting of 19,277 square feet of land (see attached recorded plan, Lot 1) Lot is zoned R-2 (Per Building Department - single or 2 family residential structure permitted.)

    Donna Bozza Barrett Sotheby's International Realty

    14 Cross St, Woburn, MA 01801
  • 298 Forest St, Arlington, MA 02474
    298 Forest St, Arlington, MA 02474
    298 Forest St, Arlington, MA 02474
    /40

    $799,000

    $126K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,770 Sq Ft

    298 Forest St, Arlington, MA 02474

    There’s more to this ranch than you might expect from the street. The main level keeps daily life straightforward, with great natural light in the fireplaced living room and adjoining dining or bonus area. Sliders lead to a deck with treetop views overlooking the yard, giving the main living areas a welcome connection to the outdoors. The eat-in kitchen is ready for its next update, but its size

    Steve McKenna Gibson Sotheby's International Realty

    298 Forest St, Arlington, MA 02474

Showing Results 1 - 40, Page 1 of 2

Massachusetts Middlesex County

Newest Listings for Sale in Winchester, MA

Winchester, MA Home Prices vs. Nearby Neighborhoods

Winchester, MA West Side North Main The Flats
Median Home Price
$1,750,000
$1,899,000
$1,237,450
$2,674,500
Median Sale Price
$1,699,000
+1% YoY
$1,678,500
+2% YoY
$1,325,000
-16% YoY
$2,575,000
+10% YoY
Avg. Price per Square Foot
$566
$534
$582
$562
Median Single Family Price
$1,794,000
$1,725,000
$1,330,000
$2,600,000
Median Townhouse Price
$1,412,500
$2,130,500
$849,000
$1,475,000
Median Condo Price
$1,389,000
$1,807,500
$1,160,000
$1,399,000
Total Active Listings
30 listings
14 listings
7 listings
5 listings
Market Conditions
2 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
2 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Winchester, MA?
Homes for sale in Winchester, MA have an average home price of $1,939,298.
How many homes have sold over the last 12 months in Winchester, MA?
177 homes have sold in Winchester, MA over the last 12 months.
What is the average household income in Winchester, MA?
The average household income in Winchester, MA is $206K.
Is Winchester, MA a safe city?
In general, the safest neighborhoods in Winchester, MA with lower crime scores are The Flats, West Side, Grove Street, Winchester Highlands and Symmes Corner.
What are the most popular zip codes in Winchester, MA?
The most popular zip codes in Winchester, MA include 01890, 01801, 02474, 02155 and 02420.
What are the most popular neighborhoods in Winchester, MA?
The most popular neighborhoods in Winchester, MA with the most homes for sale are North Main, The Flats, West Side, Grove Street and Winchester Highlands.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $1,750,000. If you put a 20% down payment of $350,000 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $9,000 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $386K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $206K.
How are the schools in Winchester, MA?
Winchester, MA has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Greater Boston Academy, Jonas Clarke Middle School and Lexington Christian Academy. The neighborhoods in Winchester with the highest rated schools are North Main, The Flats and West Side. Browse all the schools in Winchester, MA to learn more.
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