22

Winchester, MA Homes for Sale with Pool

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  • /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
  • /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
  • /40

    $3,179,000

    $200K PRICE DROP
    • 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
  • /32

    $2,695,000

    $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,233 Sq Ft

    18 Middlesex St, Winchester, MA 01890

    Your Dream Home, now at a price you'll love. 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

    Tina Natale Luxury Living Real Estate

    18 Middlesex St, 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
  • /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
  • /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
  • /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
  • /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
  • /36

    $2,100,000

    $100K PRICE INCREASE
    • 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
  • /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
  • /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
  • /30

    $349,900

    $15K PRICE DROP
    • 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
  • /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
  • /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
  • /34

    $1,329,000

    $171K 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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

Home Price Trends

Median Sale Price
$1,699,000
Median Single Family Sale Price
$1,794,000
Median Townhouse Sale Price
$1,412,500
Median 2 Bedroom Sale Price
$975,000
Average Price Per Sq Ft
$566
Number of Homes for Sale
30
Last 12 months Home Sales
177
Months of Supply
2.00
Median List Price
$1,750,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
2%
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