Winchester, MA Homes for Sale

• 

  

  

  /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
• 

  

  

  /42

  $2,650,000

  • 4 Beds
  • 3 Baths
  • 4,276 Sq Ft

  8 Tanglewood Ln, Winchester, MA 01890

  This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous home, nestled into a cul-de-sac on the West side was custom designed with soaring ceilings & large scale rooms offering unparalleled views! Enjoy meals in the updated kitchen w/ high end appliances & direct access to deck overlooking private yard.

  Kim Covino Compass

  8 Tanglewood Ln, Winchester, MA 01890
• 

  

  

  /34

  $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
• 

  

  

  /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
• 

  

  

  /42

  $2,790,000

  • 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
• 

  

  /37

  $679,900 Open Sun 1PM - 2PM

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /35

  $974,900 Open Sun 10AM - 12PM

  • 4 Beds
  • 2.5 Baths
  • 2,983 Sq Ft

  2 Washington Ave, Woburn, MA 01801

  Welcome to this well-maintained and spacious ranch-style home located on the desirable Winchester line, offering a versatile floor plan ideal for a variety of living needs. The main level features an open-concept layout that flows seamlessly, while the fully finished lower level includes a pellet stove, walk-out access, and flexible space perfect for a guest suite, home office, or recreation

  Meghan Maraghy

  2 Washington Ave, Woburn, MA 01801
• 

  

  /42

  $895,000

  • 3 Beds
  • 2 Baths
  • 1,691 Sq Ft

  338 Forest St, Arlington, MA 02474

  Welcome home to 338 Forest Street, a lovely, move-in ready Bungalow that is ideal for first-time buyers or downsizers alike. The main level features a modern, open-concept layout, with a charming living room, accented by a wood-burning fireplace, flowing into a dining area and updated kitchen, equipped with an abundance of cabinetry, granite counters, peninsula, pot filler and gas stove. This

  Steve McKenna Gibson Sotheby's International Realty

  338 Forest St, Arlington, MA 02474
• 

  

  /32

  $1,499,900 Open Sun 10:30AM - 12PM

  • 4 Beds
  • 3.5 Baths
  • 2,572 Sq Ft

  32 Henry St, Arlington, MA 02474

  Welcome to 32 Henry St! Beautifully renovated 4BR, 3.5BA Cape in sought-after Turkey Hill neighborhood. This 2,500+ sq ft home sits on a 12,000 sq ft lot with mature trees and offers modern comfort with timeless charm. The sunlit open floor plan features hardwood floors throughout and a welcoming living room with fireplace. A stunning new kitchen offers sleek custom cabinetry and a quartz island

  Acone & Company Team Darwin Associates

  32 Henry St, Arlington, MA 02474
• 

  

  /19

  $1,249,995 Open Sun 11AM - 1PM

  • 3 Beds
  • 3.5 Baths
  • 1,921 Sq Ft

  15 Mason Way Unit 73, Woburn, MA 01801

  New construction townhome at Highland at Vale in Woburn! The Wheaton floor plan offers 1,921 sq. ft. across two thoughtfully designed levels. The bright, open kitchen features stainless steel appliances, ample cabinetry, and a large island—perfect for everyday living or entertaining. An expansive gathering room and optional bay window in the dining area bring in abundant natural light, with

  Erin Sullivan Pulte Homes of New England

  15 Mason Way Unit 73, Woburn, MA 01801
• 

  

  /28

  $1,274,995 Open Sun 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  10 Mason Way Unit 61, Woburn, MA 01801

  Discover new construction at Highland at Vale in Woburn! The Southbrook is a stunning townhome featuring open-concept living and abundant natural light throughout. The spacious kitchen flows seamlessly into the gathering room and private deck—ideal for entertaining. Enjoy the ease of a first-floor Owner’s Suite complete with a spa-like bath for the perfect retreat. Upstairs, a generous loft is

  Erin Sullivan Pulte Homes of New England

  10 Mason Way Unit 61, Woburn, MA 01801
• 

  

  /30

  $1,299,995 Open Sun 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,143 Sq Ft

  13 Mason Way Unit 72, Woburn, MA 01801

  Welcome to Highland at Vale in Woburn! This new construction Jackson townhome offers 2,143 square feet of thoughtfully designed living space across two levels. The open-concept kitchen is a chef’s dream with stainless steel appliances, abundant cabinetry, and a large center island. A bright gathering room and dining area with optional bay window lead to a private outdoor deck—perfect for

  Erin Sullivan Pulte Homes of New England

  13 Mason Way Unit 72, Woburn, MA 01801

Showing Results 41 - 56, Page 2 of 2