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Newest Homes for Sale in Winchester, MA

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  • 23 Shepard Ct Unit U23, Winchester, MA 01890
    23 Shepard Ct Unit U23, Winchester, MA 01890
    23 Shepard Ct Unit U23, Winchester, MA 01890
    /37

    $749,000

    Open Sat 12:30PM - 2PM
    • 3 Beds
    • 4 Baths
    • 1,380 Sq Ft

    23 Shepard Ct Unit U23, Winchester, MA 01890

    Beautifully maintained townhouse-style condex offering 3 levels of living in a prime Winchester location. This sun-filled home features 3 bedrooms, 2 full baths, a convenient 3rd floor half bath, and an additional half bath in the basement. The third-floor bedroom offers flexibility as a primary suite, guest retreat, or home office. Recent updates include a 2019 high-efficiency gas boiler, 2019

    Nancy Zhang Zhenning Fairview Partners International LLC

    23 Shepard Ct Unit U23, Winchester, MA 01890
  • 10 Bonad Rd, Winchester, MA 01890
    10 Bonad Rd, Winchester, MA 01890
    10 Bonad Rd, Winchester, MA 01890
    /39

    $1,499,000

    Open Sat 11AM - 12:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,233 Sq Ft

    10 Bonad Rd, Winchester, MA 01890

    Welcome home to this sun-filled, south-facing 4-bed Colonial in a beloved Winchester neighborhood. Hardwood floors guide you from the gracious foyer into a spacious, fireplaced living room ideal for gatherings. The airy formal dining room flows seamlessly onto a private back deck overlooking a professionally landscaped, fully fenced yard—perfect for al fresco dining & entertaining. The updated

    Kim Covino Compass

    10 Bonad Rd, Winchester, MA 01890
  • 24 Hinds Rd, Winchester, MA 01890
    24 Hinds Rd, Winchester, MA 01890
    24 Hinds Rd, Winchester, MA 01890
    /42

    $1,799,000

    Open Sat 11AM - 12:30PM
    • 4 Beds
    • 3 Baths
    • 2,814 Sq Ft

    24 Hinds Rd, Winchester, MA 01890

    Welcome to the home that has it all! Where thoughtful upgrades meet effortless living. This tastefully updated open-concept home is designed for both quiet nights and grand entertaining. Enjoy one-level living with a stunning sun drenched family room, adjacent dining & renovated kitchen with direct outdoor access, ideal for hosting!The home features 4 generously sized bedrooms, and 3 full baths

    Kim Covino Compass

    24 Hinds Rd, Winchester, MA 01890
  • 15 Thornberry Rd, Winchester, MA 01890
    15 Thornberry Rd, Winchester, MA 01890
    15 Thornberry Rd, Winchester, MA 01890
    /41

    $1,350,000

    • 4 Beds
    • 3 Baths
    • 4,062 Sq Ft

    15 Thornberry Rd, Winchester, MA 01890

    Located on a level corner lot in the desirable Vinson Owen School district and nearby Winchester Swim & Tennis Club, this ranch-style home offers abundant space and a flexible floor plan. The main level features three bedrooms, a full bath, hardwood floors, and a fireplace living room that flows into the dining area and kitchen. A heated sunroom/mudroom with skylights and exposed beams connects

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

    15 Thornberry Rd, Winchester, MA 01890
  • 18 Bradford Rd, Winchester, MA 01890
    18 Bradford Rd, Winchester, MA 01890
    18 Bradford Rd, Winchester, MA 01890
    /28

    $659,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 1.5 Baths
    • 1,331 Sq Ft

    18 Bradford Rd, Winchester, MA 01890

    Welcome to this beautifully updated 3-bedroom,1.5-bath townhouse with a large flat Exclusive to use backyard (0.18 acres) located in Residences at Winchester, the highly desirable new Lynch School district with low condo fees. The spacious sun-filled living room offers large windows, abundant natural light, and gleaming hardwood floors throughout the home. The renovated kitchen features quartz

    Wei Wenny Fu Phoenix Real Estate

    18 Bradford Rd, Winchester, MA 01890
  • 22 Hollywood Rd, Winchester, MA 01890
    22 Hollywood Rd, Winchester, MA 01890
    22 Hollywood Rd, Winchester, MA 01890
    /39

    $1,999,000

    Open Sat 11AM - 12PM
    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft

    22 Hollywood Rd, Winchester, MA 01890

    Beautifully appointed 5BR, 2 full/2 half bath home with 3,136 sq ft of thoughtfully designed living space on a flat, fully fenced .34 acre lot. Renovated kitchen with quartz countertops and luxury appliances. Expansive and bright living room with custom built-ins, window seating, and gas fireplace. The main living level also offers 3 spacious bedrooms and a serene primary suite with a walk-in

    Andersen Group Realty Keller Williams Realty Boston Northwest

    22 Hollywood Rd, Winchester, MA 01890
  • 41 Cross St, Winchester, MA 01890
    41 Cross St, Winchester, MA 01890
    41 Cross St, Winchester, MA 01890
    /42

    $1,110,000

    $111K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 2,085 Sq Ft

    41 Cross St, Winchester, MA 01890

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

    Andersen Group Realty Keller Williams Realty Boston Northwest

    41 Cross St, Winchester, MA 01890
  • 7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    /39

    $1,550,000

    Open Sat 11:30AM - 1PM
    • 5 Beds
    • 5 Baths
    • 3,360 Sq Ft

    7 Ridge St, Winchester, MA 01890

    Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds

    Paul Cirignano The Synergy Group

    7 Ridge St, Winchester, MA 01890
  • 28 Tyler Rd, Lexington, MA 02420
    28 Tyler Rd, Lexington, MA 02420
    28 Tyler Rd, Lexington, MA 02420
    /36

    $5,500,000

    • 7 Beds
    • 7.5 Baths
    • 10,557 Sq Ft

    28 Tyler Rd, Lexington, MA 02420

    True private resort living. Set on a private .73-acre lot in one of Lexington’s most coveted neighborhoods, This home offers over 10,500SF of curated living & entertaining space w/ 7 beds & 7.5 baths. Privately sited behind mature landscaping, this estate blends timeless architecture w/ resort-style amenities. Dramatic two-story foyer w/ arched windows, formal living & dining rooms, expansive

    Ricardo Rodriguez Coldwell Banker Realty - Boston

    28 Tyler Rd, Lexington, MA 02420
  • 303 Washington St, Winchester, MA 01890
    303 Washington St, Winchester, MA 01890
    303 Washington St, Winchester, MA 01890
    /42

    $1,375,000

    Open Sat 1PM - 2:30PM
    • 6 Beds
    • 2 Baths
    • 5,047 Sq Ft

    303 Washington St, Winchester, MA 01890

    Pleased to present this meticulously maintained and nicely updated two family home in the heart of Winchester! Each spacious unit is one level & features seven rooms including 3 large bedrooms, living room w fplc, dining room w/wainscoting, sunroom, kitchen & updated baths. The generously sized flowing rooms are highlighted by high ceilings, oversized windows, beautiful original woodwork and

    Kim Covino Compass

    303 Washington St, Winchester, MA 01890
  • 78 Bacon St, Winchester, MA 01890
    78 Bacon St, Winchester, MA 01890
    78 Bacon St, Winchester, MA 01890
    /42

    $2,599,000

    Open Sat 11AM - 12:30PM Pre-Foreclosure
    • 5 Beds
    • 3.5 Baths
    • 5,230 Sq Ft

    78 Bacon St, Winchester, MA 01890

    Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR,

    Kim Covino Compass

    78 Bacon St, Winchester, MA 01890
  • 94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    /40

    $1,799,000

    Open Sat 1PM - 2:30PM
    • 4 Beds
    • 3 Baths
    • 3,366 Sq Ft

    94 Johnson Rd, Winchester, MA 01890

    Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated

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

    94 Johnson Rd, Winchester, MA 01890
  • 53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    /12

    $2,599,000

    Open Sat 2PM - 3PM $200K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 5,083 Sq Ft

    53 Winford Way, Winchester, MA 01890

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

    Andersen Group Realty Keller Williams Realty Boston Northwest

    53 Winford Way, Winchester, MA 01890
  • 105 Thornberry Rd, Winchester, MA 01890
    105 Thornberry Rd, Winchester, MA 01890
    105 Thornberry Rd, Winchester, MA 01890
    /35

    $1,899,000

    • 5 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    105 Thornberry Rd, Winchester, MA 01890

    Perfectly situated on Winchester’s sought-after Westside, this beautifully updated Colonial offers 5 bedrooms, 2.5 baths, and exceptional indoor-outdoor living. A recent renovation transformed and expanded the first floor, featuring an updated kitchen with oversized mahogany topped center island, family room, dining room, mudroom, and half bath. The kitchen opens seamlessly to a spacious family

    Monte Marrocco Coldwell Banker Realty - Lexington

    105 Thornberry Rd, Winchester, MA 01890
  • 200 Swanton St Unit 303, Winchester, MA 01890
    200 Swanton St Unit 303, Winchester, MA 01890
    200 Swanton St Unit 303, Winchester, MA 01890
    /19

    $505,000

    Open Sat 2PM - 3PM
    • 2 Beds
    • 1 Bath
    • 822 Sq Ft

    200 Swanton St Unit 303, Winchester, MA 01890

    Enjoy living in sought-after Winchester, just minutes from Winchester Center, local shops, dining, parks, and commuter access. This beautifully updated two-bedroom condo at Parkview features a modern kitchen with stainless steel appliances, perfect for entertaining, fresh paint throughout, and a bright open-concept layout. Both generously sized bedrooms offer excellent closet space and

    Agent Photo

    Joan Powell

    REMAX Andrew Realty Services

    (781) 562-4157

    200 Swanton St Unit 303, Winchester, MA 01890
  • 8 Hawthorne Rd, Winchester, MA 01890
    8 Hawthorne Rd, Winchester, MA 01890
    8 Hawthorne Rd, Winchester, MA 01890
    /24

    $1,925,000

    Open Mon 6PM - 7PM
    • 5 Beds
    • 4 Baths
    • 3,315 Sq Ft

    8 Hawthorne Rd, Winchester, MA 01890

    Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees.

    Elaine Song Coldwell Banker Realty - Lexington

    8 Hawthorne Rd, Winchester, MA 01890
  • 22 Arthur St, Winchester, MA 01890
    22 Arthur St, Winchester, MA 01890
    22 Arthur St, Winchester, MA 01890
    /13

    $414,500

    • 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
  • 2 Atherton Rd, Winchester, MA 01890
    2 Atherton Rd, Winchester, MA 01890
    2 Atherton Rd, Winchester, MA 01890
    /38

    $3,600,000

    Open Sat 12:30PM - 1:30PM
    • 6 Beds
    • 6.5 Baths
    • 7,400 Sq Ft

    2 Atherton Rd, Winchester, MA 01890

    This extraordinary 6-bedroom, 6.5-bath luxury home offers approximately 7,400 square feet of impeccably crafted living space designed for sophisticated living and grand-scale entertaining. A dramatic open-concept floor plan is highlighted by soaring ceilings, a statement fireplace, and expansive walls of Pella windows that flood the interiors with natural light. The designer chef’s kitchen is

    Brooke Zarbano Regatta Realty

    2 Atherton Rd, Winchester, MA 01890
  • 53 Lake St, Winchester, MA 01890
    53 Lake St, Winchester, MA 01890
    53 Lake St, Winchester, MA 01890
    /36

    $1,225,000

    Open Sun 11AM - 12PM
    • 3 Beds
    • 2.5 Baths
    • 2,235 Sq Ft

    53 Lake St, Winchester, MA 01890

    Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming

    Kim Covino Compass

    53 Lake St, Winchester, MA 01890
  • 18 Middlesex St, Winchester, MA 01890
    18 Middlesex St, Winchester, MA 01890
    18 Middlesex St, Winchester, MA 01890
    /32

    $2,795,000

    Open Sat 11AM - 12:30PM
    • 4 Beds
    • 4.5 Baths
    • 5,233 Sq Ft

    18 Middlesex St, Winchester, MA 01890

    This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the

    Tina Natale Luxury Living Real Estate

    18 Middlesex St, Winchester, MA 01890
  • 465 Washington St Unit 467, Winchester, MA 01890
    465 Washington St Unit 467, Winchester, MA 01890
    465 Washington St Unit 467, Winchester, MA 01890
    /26

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 2,666 Sq Ft

    465 Washington St Unit 467, Winchester, MA 01890

    Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is

    Nancy Pallotta Gibson Sotheby's International Realty

    465 Washington St Unit 467, Winchester, MA 01890
  • 47 Yale St, Winchester, MA 01890
    47 Yale St, Winchester, MA 01890
    47 Yale St, Winchester, MA 01890
    /35

    $2,675,000

    Open Sat 12PM - 1:30PM $75K PRICE DROP
    • 6 Beds
    • 5 Baths
    • 4,540 Sq Ft

    47 Yale St, Winchester, MA 01890

    Timeless 1920 brick Tudor in the heart of the Flats neighborhood combines all of today’s modern amenities with classic architectural charm to create an exceptional home for modern living offering 6 bedrooms, 3 full and 2 half baths. A welcoming entry opens to a sun-filled living room with custom built-ins, fireplace, and French doors to a private office. The open dining room flows into a chef’s

    Molly Nolan Byrne Coldwell Banker Realty - Belmont

    47 Yale St, Winchester, MA 01890
  • 63-65 Harvard St, Winchester, MA 01890
    63-65 Harvard St, Winchester, MA 01890
    63-65 Harvard St, Winchester, MA 01890
    /33

    $1,150,000

    • 5 Beds
    • 3 Baths
    • 2,186 Sq Ft

    63-65 Harvard St, Winchester, MA 01890

    Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home.

    Beth Sager Group Keller Williams Realty Boston Northwest

    63-65 Harvard St, Winchester, MA 01890
  • 7 Sherman Place, Winchester, MA 01890
    7 Sherman Place, Winchester, MA 01890
    7 Sherman Place, Winchester, MA 01890
    /40

    $1,495,000

    Open Sun 11AM - 12PM
    • 4 Beds
    • 2.5 Baths
    • 2,605 Sq Ft

    7 Sherman Place, Winchester, MA 01890

    Welcome to this sun-drenched newer construction & freshly updated 4 Bed 2.5 Bath luxury townhome, set on a quiet cul-de-sac with a private, professionally landscaped yard & secret garden. This spacious home lives like a free standing house with a thoughtful layout designed for both everyday living and entertaining. Highlights include soaring 9-foot ceilings, oversized windows & high efficiency

    Kim Covino Compass

    7 Sherman Place, Winchester, MA 01890
  • 200 Swanton St Unit 318, Winchester, MA 01890
    200 Swanton St Unit 318, Winchester, MA 01890
    200 Swanton St Unit 318, Winchester, MA 01890
    /9

    $379,900

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 318, Winchester, MA 01890

    Beautifully renovated oversized one-bedroom condo at Parkview Condominium featuring an open floor plan and private balcony overlooking a serene Japanese garden and duck pond. Spacious primary bedroom offers room for a king-size bed and includes a walk-in closet. Updated kitchen, bathroom, and flooring provide years of low-maintenance living. Amenities include swimming pool, cabana, picnic

    Mike Huang Lewis & Joyce Real Estate

    200 Swanton St Unit 318, Winchester, MA 01890
  • 8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    /35

    $3,250,000

    Open Sun 12PM - 1PM
    • 5 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    8 Priscilla Ln, Winchester, MA 01890

    Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef’s kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and

    The Pezzano Group Rise Signature Homes

    8 Priscilla Ln, Winchester, MA 01890
  • 129 Washington St Unit 131, Winchester, MA 01890
    129 Washington St Unit 131, Winchester, MA 01890
    129 Washington St Unit 131, Winchester, MA 01890
    /31

    $1,260,000

    $39K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,420 Sq Ft

    129 Washington St Unit 131, Winchester, MA 01890

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

    The Mary Scimemi Team Leading Edge Real Estate

    129 Washington St Unit 131, Winchester, MA 01890
  • 50 Brooks St, Winchester, MA 01890
    50 Brooks St, Winchester, MA 01890
    50 Brooks St, Winchester, MA 01890
    /42

    $2,549,000

    Open Sat 1PM - 2:30PM $46K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,403 Sq Ft

    50 Brooks St, Winchester, MA 01890

    Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home &

    Kim Covino Compass

    50 Brooks St, Winchester, MA 01890
  • 6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    /36

    $2,000,000

    • 6 Beds
    • 5 Baths
    • 3,403 Sq Ft

    6 Ivy Cir, Winchester, MA 01890

    Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves

    Valerie Post Engel & Volkers Boston

    6 Ivy Cir, Winchester, MA 01890
  • 2 Stratton Dr Unit 307, Woburn, MA 01801
    2 Stratton Dr Unit 307, Woburn, MA 01801
    2 Stratton Dr Unit 307, Woburn, MA 01801
    /21

    $599,000

    $26K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 985 Sq Ft

    2 Stratton Dr Unit 307, Woburn, MA 01801

    2024-built 1 bedroom condo at Highland at Vale offering easy single-level living! This bright, open-concept home features an airy, contemporary layout ideal for both everyday living and entertaining. The stylish white kitchen showcases stainless steel appliances, ample storage, and a center island, seamlessly flowing into the dining and living areas. Sliders from the living room lead to a private

    Kim Covino Compass

    2 Stratton Dr Unit 307, Woburn, MA 01801
  • 16 Glenwood Ave, Winchester, MA 01890
    16 Glenwood Ave, Winchester, MA 01890
    16 Glenwood Ave, Winchester, MA 01890
    /41

    $2,099,000

    Open Sat 1PM - 2:30PM $101K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft

    16 Glenwood Ave, Winchester, MA 01890

    Must see! Beautifully renovated & expanded Cape 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, dining room, 1st flr

    Kim Covino Compass

    16 Glenwood Ave, Winchester, MA 01890
  • 37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    /40

    $3,379,000

    • 7 Beds
    • 7.5 Baths
    • 8,540 Sq Ft

    37 Mayflower Rd, Winchester, MA 01890

    Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

    Kim Covino Compass

    37 Mayflower Rd, Winchester, MA 01890
  • 14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    /36

    $2,799,000

    $51K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 6,968 Sq Ft

    14 Nassau Dr, Winchester, MA 01890

    Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

    Weidong Li WINN Real Estate & Consulting

    14 Nassau Dr, Winchester, MA 01890
  • 200 Swanton St Unit 717, Winchester, MA 01890
    200 Swanton St Unit 717, Winchester, MA 01890
    200 Swanton St Unit 717, Winchester, MA 01890
    /30

    $364,900

    • 1 Bed
    • 1 Bath
    • 613 Sq Ft

    200 Swanton St Unit 717, Winchester, MA 01890

    Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for

    Cameron Moniz Coldwell Banker Realty - Lexington

    200 Swanton St Unit 717, Winchester, MA 01890
  • 1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    /35

    $3,299,000

    Open Sat 11AM - 12:30PM $100K PRICE DROP
    • 7 Beds
    • 7.5 Baths
    • 7,226 Sq Ft

    1 Plymouth Rd, Winchester, MA 01890

    Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    1 Plymouth Rd, Winchester, MA 01890
  • 83 Church St Unit 15, Winchester, MA 01890
    83 Church St Unit 15, Winchester, MA 01890
    83 Church St Unit 15, Winchester, MA 01890
    /34

    $1,100,000

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

    83 Church St Unit 15, Winchester, MA 01890

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

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

    83 Church St Unit 15, Winchester, MA 01890
  • 380 Cross St, Winchester, MA 01890
    380 Cross St, Winchester, MA 01890
    380 Cross St, Winchester, MA 01890
    /41

    $929,900

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,938 Sq Ft

    380 Cross St, Winchester, MA 01890

    This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a nice place for family to congregate and get to

    Rajive Dogra Coldwell Banker Realty - Lexington

    380 Cross St, Winchester, MA 01890
  • 4 Stratton Dr Unit 308, Woburn, MA 01801
    4 Stratton Dr Unit 308, Woburn, MA 01801
    4 Stratton Dr Unit 308, Woburn, MA 01801
    /24

    $889,000

    • 3 Beds
    • 2 Baths
    • 1,370 Sq Ft

    4 Stratton Dr Unit 308, Woburn, MA 01801

    Commuter-friendly, thoughtfully designed newer construction condo at Highland at Vale offering a refined take on low-maintenance living in Woburn. Positioned on the 3rd floor with high ceilings, this single-level home features scenic sunset views from a private balcony with a hilltop vantage and seamless indoor-outdoor flow. The layout is effortlessly arranged for privacy with 2 spacious

    Erika Tarlow Coldwell Banker Realty - Boston

    4 Stratton Dr Unit 308, Woburn, MA 01801
  • 200 Swanton St Unit T35, Winchester, MA 01890
    200 Swanton St Unit T35, Winchester, MA 01890
    200 Swanton St Unit T35, Winchester, MA 01890
    /39

    $400,000

    Open Sat 11:30AM - 2PM $115K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 810 Sq Ft

    200 Swanton St Unit T35, Winchester, MA 01890

    SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of

    Nuri Tirana Tirana Real Estate Group

    200 Swanton St Unit T35, Winchester, MA 01890
  • 276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    /38

    $2,195,000

    $104K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 5,006 Sq Ft

    276 High St, Winchester, MA 01890

    Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

    Kim Covino Compass

    276 High St, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

Massachusetts Middlesex County Winchester

Newest Listings for Sale in Winchester, MA

Frequently Asked Questions

What is the average home price in Winchester, MA?
Homes for sale in Winchester, MA have an average home price of $1,867,835.
Are home prices dropping in Winchester?
Yes, home prices in Winchester are down 2% in the last 12 months.
How many homes have sold over the last 12 months in Winchester, MA?
181 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, 02155, 02474 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, Winchester Highlands and Symmes Corner.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $1,612,500. If you put a 20% down payment of $322,500 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $8,140 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $349K 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, Lexington Christian Academy and Lexington High School. 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.

Home Prices in Winchester, MA

The median home sale price in Winchester, MA is $1,558,200, down 8% year-over-year. Homes in Winchester sell in 22 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$1,558,200
Median Single Family Sale Price
$1,737,500
Median Townhouse Sale Price
$1,300,000
Median 2 Bedroom Sale Price
$940,000
Average Price Per Sq Ft
$559
Number of Homes for Sale
33
Last 12 months Home Sales
181
Months of Supply
2.20
Median List Price
$1,612,500
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-8%
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