9

Winchester, MA Homes for Sale under $1,000,000

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  • /40

    $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
  • /38

    $900,000

    • 4 Beds
    • 2 Baths
    • 2,083 Sq Ft

    84 Oak St, Winchester, MA 01890

    Charming and Spacious Custom Built Mid-Century Bungalow offers a wonderful opportunity to live in Winchester ! Do you want to send your children to the award-winning public schools? Need an in-law? Generously sized, sun-drenched, freshly painted rooms with hardwood floors, and two fireplaces. A terrific, flat backyard perfect for growing gardens. A fully finished lower-level creates excellent 2nd

    John Magazzu Charlesgate Realty Group LLC

    84 Oak St, Winchester, MA 01890
  • /34

    $999,000

    Open Sat 1PM - 2PM $101K PRICE DROP
    • 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
  • /21

    $799,000

    Open Sat 11AM - 12:30PM
    • 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
  • /30

    $950,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 1 Bath
    • 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
  • /12

    $829,000

    • Land
    • 19,166 Sq Ft
    • $1,884,091 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
  • /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
  • /23

    $729,000

    Open Fri 5PM - 6PM
    • 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
  • /39

    $889,000

    $36K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,770 Sq Ft

    298 Forest St, Arlington, MA 02474

    Not every home needs to be finished on day one. Sometimes the best houses are the ones that already live well and leave room for your ideas later. This ranch makes life simple from the start with everything you need on one level. Discover a comfortable living room that opens into a dining area or bonus space depending on your needs. The large eat-in kitchen has room to gather today and provides

    Steve McKenna Gibson Sotheby's International Realty

    298 Forest St, Arlington, MA 02474

Home Price Trends

Median Sale Price
$1,627,000
Median Single Family Sale Price
$1,737,500
Median Townhouse Sale Price
$1,475,000
Median 2 Bedroom Sale Price
$940,000
Average Price Per Sq Ft
$565
Number of Homes for Sale
34
Last 12 months Home Sales
174
Months of Supply
2.30
Median List Price
$1,699,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-3%
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