Homes for Sale near Winchester High School

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  /39

  $1,099,000

  • 5 Beds
  • 2.5 Baths
  • 2,801 Sq Ft

  257 Cross St, Winchester, MA 01890

  Exceptional two-family opportunity with incredible potential to renovate/expand! Situated on a large, level corner lot with frontage on both Cross Street and Verplast Avenue, this property offers endless possibilities for investors, builders, or owner-occupants. The first-floor unit features a fireplaced living room, an updated kitchen, three bedrooms, 1.5 baths and sunroom overlooking the

  Kim Covino Compass

  257 Cross St, Winchester, MA 01890
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  /40

  $2,300,000

  Open Sat 11AM - 1PM $80K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,881 Sq Ft

  14 Hillside Ave, Winchester, MA 01890

  Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom

  Rebecca Huang William Raveis R.E. & Home Services

  14 Hillside Ave, Winchester, MA 01890
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  /38

  $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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  /33

  $1,150,000

  • 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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  /39

  $400,000

  Open Sat 12PM - 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
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  /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 a quiet Winchester cul-de-sac near Wright Locke Farm. Newly completed, this exceptional residence spans more than 7,000 square feet across four impeccably finished levels. Ideally positioned on a quiet cul-de-sac in one of Winchester’s most desirable locations, the home offers an extraordinary combination of new construction, refined design,

  Valerie Post Engel & Volkers Boston

  11 Viking Rd, Winchester, MA 01890
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  /37

  $2,500,000

  • 5 Beds
  • 3 Baths
  • 4,071 Sq Ft

  9 Plymouth Rd, Winchester, MA 01890

  Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for

  Stephanie Crawford Real Broker MA, LLC

  9 Plymouth Rd, Winchester, MA 01890

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