Homes for Sale near Winchester High School

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  /40

  $2,099,000

  • 6 Beds
  • 3.5 Baths
  • 4,696 Sq Ft

  5 Squire Rd, Winchester, MA 01890

  Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

  Alina Wang Coldwell Banker Realty - Lexington

  5 Squire Rd, Winchester, MA 01890
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  /4

  $3,799,900

  • 7 Beds
  • 7.5 Baths
  • 7,429 Sq Ft

  11 Viking Rd, Winchester, MA 01890

  Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

  The McLaren D'Agostino Team Compass

  11 Viking Rd, Winchester, MA 01890
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  /22

  $1,295,000

  • 4 Beds
  • 1.5 Baths
  • 2,202 Sq Ft

  71 Woodside Rd, Winchester, MA 01890

  Nestled in the heart of Winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square feet of living space on a 7,126-square-foot lot. Built in 1927, the home exudes timeless character with its spacious rooms, abundant natural light, and original architectural details. Perfect for homeowners and developers alike, the property offers endless potential for renovation,

  Jorge Rodriguez Carlton's Wharf & Co.

  71 Woodside Rd, Winchester, MA 01890
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  $3,698,000

  • 6 Beds
  • 7 Baths
  • 8,866 Sq Ft

  20 Amberwood Dr, Winchester, MA 01890

  Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

  Dan Li Keller Williams Realty

  20 Amberwood Dr, Winchester, MA 01890
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  /42

  $3,989,000

  • 6 Beds
  • 6.5 Baths
  • 8,463 Sq Ft

  26 Swan Rd, Winchester, MA 01890

  Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary suite options! This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end

  Kim Covino Compass

  26 Swan Rd, Winchester, MA 01890
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  /42

  $2,890,000

  • 5 Beds
  • 6 Baths
  • 5,354 Sq Ft

  8 Chestnut St, Winchester, MA 01890

  Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and

  The McLaren D'Agostino Team Compass

  8 Chestnut St, Winchester, MA 01890
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  /37

  $679,900

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft

  7 Conant Rd Unit 20, Winchester, MA 01890

  Rarely available and beautifully renovated first-floor unit at The Willows designed with everyday functionality in mind. This one-story unit offers stair-free access and living, along with easy accessibility from the adjacent one-car garage with an attic and a tandem parking spot. Upon entry, you’ll find an inviting open concept living and dining area with freshly installed hardwood flooring, a

  Brian Woods Woods Properties Inc.

  7 Conant Rd Unit 20, Winchester, MA 01890
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  /42

  $3,699,000

  • 7 Beds
  • 7.5 Baths
  • 7,982 Sq Ft

  54 Johnson Rd, Winchester, MA 01890

  This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master

  Kim Covino Compass

  54 Johnson Rd, Winchester, MA 01890
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  /5

  $3,999,000 New Construction

  • 6 Beds
  • 4.5 Baths
  • 6,367 Sq Ft

  40 Foxcroft Rd, Winchester, MA 01890

  An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and

  Monte Marrocco Coldwell Banker Realty - Lexington

  40 Foxcroft Rd, Winchester, MA 01890
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  /5

  $2,899,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,627 Sq Ft

  11 Taft Dr, Winchester, MA 01890

  Luxury and location converge in this stunning 5-bedroom, 5.5-bathroom home nestled in one of Winchester’s most coveted Westside neighborhoods. Beautifully rehabbed and thoughtfully expanded, this turnkey residence offers over 4,600 sq. ft. of refined living space, just steps from Ambrose School, one block from the Alewife bus stop, & a short ½-mile stroll to the commuter rail. Every detail has

  Monte Marrocco Coldwell Banker Realty - Lexington

  11 Taft Dr, Winchester, MA 01890
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  /2

  $674,900

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  20 Arthur St, Winchester, MA 01890

  Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show.

  Dan O'Connell LAER Realty Partners

  20 Arthur St, Winchester, MA 01890

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