Newest Homes for Sale in Winchester, MA

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  $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
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  $1,110,000

  $40K PRICE DROP

  • 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
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  $1,099,000

  $200K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,420 Sq Ft

  129 Washington St Unit 131, Winchester, MA 01890

  Experience the best of Winchester with a home that pairs exceptional value with an unbeatable location. Just moments from Winchester Center, enjoy a low-maintenance lifestyle within walking distance of downtown, the commuter rail, and all three school levels. This townhouse-style condo lives like a single-family home, offering space, flow, and flexibility across four finished levels. The open

  The Mary Scimemi Team Leading Edge Real Estate

  129 Washington St Unit 131, Winchester, MA 01890
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  $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
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  $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
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  $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
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  $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
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  $3,299,000

  $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
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  $975,000

  $125K 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
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  $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
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  $3,200,000

  $200K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 6,100 Sq Ft

  9 Albamont Rd, Winchester, MA 01890

  Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept

  Kim Covino Compass

  9 Albamont Rd, Winchester, MA 01890

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