24

Winchester, MA Open Houses

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  • /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
  • /17

    $375,000

    Open Wed 5:30PM - 6:30PM $24K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 228, Winchester, MA 01890

    Welcome to Parkview Condos! This one bed one bath, bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with new flooring and excellent closet space, freshly

    Agent Photo

    Joan Powell

    REMAX Andrew Realty Services

    (781) 417-5122

    200 Swanton St Unit 228, Winchester, MA 01890
  • /40

    $1,799,000

    Open Sun 11:30AM - 1PM $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,010 Sq Ft

    1 Town Way, Winchester, MA 01890

    Welcome home to this completely renovated gem, ideally situated 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 buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy

    Philip Vita Compass

    1 Town Way, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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

Home Prices in Winchester, MA

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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