16

Winchester, MA Open Houses

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  • /41

    $1,990,000 Open Sun 1PM - 2:30PM

    • 4 Beds
    • 4.5 Baths
    • 4,474 Sq Ft

    4 Chestnut St, Winchester, MA 01890

    Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blue cabinetry, copper accents, and bold designer touches. One bedroom opens to a composite deck

    Agent Photo

    Tyson Lynch

    The Proper Nest Real Estate

    (781) 633-6582

    4 Chestnut St, Winchester, MA 01890
  • /26

    $2,239,000 Open Sat 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 4,798 Sq Ft

    61 Grove St, Winchester, MA 01890

    STUNNING CUSTOM-BUILT HOME, Welcome to this easy living, maintenance free sophisticated residence. Completely rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. FIRST FLOOR LUXURIOUS SUITE with a LARGE BEDROOM, marble bath w/double sink vanity, walk in shower & soaking tub. An exquisite kitchen with granite island, counters and back splash, All Bosch appliances,

    Dorothea Feffer Coldwell Banker Realty - Lexington

    61 Grove St, Winchester, MA 01890
  • /42

    $2,499,000 Open Sat 11AM - 12PM

    • 6 Beds
    • 4.5 Baths
    • 4,200 Sq Ft

    14 Grant Rd, Winchester, MA 01890

    Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space

    Monte Marrocco Coldwell Banker Realty - Lexington

    14 Grant Rd, Winchester, MA 01890
  • /35

    $2,399,000 Open Sat 12:30PM - 1:30PM

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

    6 Ivy Cir, Winchester, MA 01890

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

    Monte Marrocco Coldwell Banker Realty - Lexington

    6 Ivy Cir, Winchester, MA 01890
  • /41

    $2,899,000 Open Sat 1PM - 2PM

    • 7 Beds
    • 5.5 Baths
    • 5,864 Sq Ft

    10 Sheffield Rd, Winchester, MA 01890

    This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master

    Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Sheffield Rd, Winchester, MA 01890
  • /41

    $2,899,000 Open Sun 1:30PM - 2:30PM

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

    11 Fieldstone Dr, Winchester, MA 01890

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

    Andersen Group Realty Keller Williams Realty Boston Northwest

    11 Fieldstone Dr, Winchester, MA 01890
  • /35

    $2,299,000 Open Thu 4PM - 6PM

    • 5 Beds
    • 3.5 Baths
    • 6,232 Sq Ft

    5 Azalea Rd, Winchester, MA 01890

    NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials

    Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

    5 Azalea Rd, Winchester, MA 01890
  • /38

    $2,499,000 Open Sun 12PM - 1:30PM

    • 7 Beds
    • 5.5 Baths
    • 4,829 Sq Ft

    89 Wildwood St, Winchester, MA 01890

    Brand-New Luxury Construction! This exquisite 7-bedroom, 5.5-bath home blends sophisticated design with functional elegance. Crafted w/ top-tier finishes throughout, the open-concept layout is ideal for modern living & effortless entertaining. The chef’s kitchen showcases an oversized quartz island, premium appliances, & a sunny breakfast nook w/ sliders opening to a private backyard oasis. A

    Monte Marrocco Coldwell Banker Realty - Lexington

    89 Wildwood St, Winchester, MA 01890
  • /33

    $1,725,000 Open Thu 5PM - 6:30PM

    • 4 Beds
    • 3.5 Baths
    • 2,755 Sq Ft

    5 Thornton Rd, Winchester, MA 01890

    This stately home near the Flats blends original character with modern-day living and awaits your personal touches. The living room features stunning woodwork, a wood-burning fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen.

    Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

    5 Thornton Rd, Winchester, MA 01890
  • /16

    $1,225,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3 Baths
    • 1,860 Sq Ft

    60 Harvard St, Winchester, MA 01890

    Exceptional investment opportunity. Located in the heart of desirable Winchester, this 3 family property offers a rare opportunity to own a ready to renovate vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while

    Mark Krasnyansky eXp Realty

    60 Harvard St, Winchester, MA 01890
  • /42

    $1,899,000 Open Thu 5:30PM - 6:30PM

    • 5 Beds
    • 3.5 Baths
    • 3,294 Sq Ft

    20 Grove Place, Winchester, MA 01890

    From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Cafe appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a

    Andersen Group Realty Keller Williams Realty Boston Northwest

    20 Grove Place, Winchester, MA 01890
  • /36

    $1,980,000 Open Sat 1PM - 2:30PM

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

    4 Fieldstone Dr, Winchester, MA 01890

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

    Wenli Zheng Fairview Partners International LLC

    4 Fieldstone Dr, Winchester, MA 01890
  • /36

    $1,349,900 Open Wed 4PM - 5:30PM

    • 5 Beds
    • 2 Baths
    • 1,706 Sq Ft

    35 Harvard St, Winchester, MA 01890

    Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well

    Joanne Mulkerin J. Mulkerin Realty

    35 Harvard St, Winchester, MA 01890
  • /32

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

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

    162 Swanton St Unit 162, Winchester, MA 01890

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

    Monte Marrocco Coldwell Banker Realty - Lexington

    162 Swanton St Unit 162, Winchester, MA 01890
  • /39

    $3,249,000 Open Sat 12PM - 1PM

    • 6 Beds
    • 6.5 Baths
    • 6,028 Sq Ft

    44 Cabot St, Winchester, MA 01890

    Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The

    Andersen Group Realty Keller Williams Realty Boston Northwest

    44 Cabot St, Winchester, MA 01890
  • /32

    $1,499,900 Open Sat 12:30PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 2,572 Sq Ft

    32 Henry St, Arlington, MA 02474

    Welcome to 32 Henry St! Beautifully renovated 4BR, 3.5BA Cape in sought-after Turkey Hill neighborhood. This 2,500+ sq ft home sits on a 12,000 sq ft lot with mature trees and offers modern comfort with timeless charm. The sunlit open floor plan features hardwood floors throughout and a welcoming living room with fireplace. A stunning new kitchen offers sleek custom cabinetry and a quartz island

    Acone & Company Team Darwin Associates

    32 Henry St, Arlington, MA 02474

Home Trends in Winchester, MA

Housing Trends

Median Sale Price
$1,558,000
Median Single Family Sale Price
$1,952,000
Median Townhouse Sale Price
$1,450,000
Median 2 Bedroom Sale Price
$715,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$552
Number of Homes for Sale
46
Last 12 months Home Sales
233
Months of Supply
2.40
Median List Price
$1,649,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
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