Winchester, MA Homes

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  /34

  Est $1,030,311 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,859 Sq Ft

  36 Edward Dr, Winchester, MA 01890

  36 Edward Dr, 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
• 

  

  

  /25

  $1,000,000 Sold Dec 23, 2024

  • 2,355 Sq Ft
  • $425/SF
  • 11 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1900

  37-39 Middlesex St, Winchester, MA 01890

  Motivated Sellers! Wonderful 2 Family on a quiet side street area just off Wedge Pond. Welcome to 37 - 39 Middlesex Street, Winchester. Lack of inside pictures is to protect privacy of the tenants and NOT an indication of poor condition. This is a very solid Two-Family Large Backyard with tremendous privacy behind property abutting Town owned land. Reciprocal side by side duplex with separate

  Craig Celli

  37-39 Middlesex St, Winchester, MA 01890
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  /42

  Est $1,005,169 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,793 Sq Ft

  31 Edward Dr, Winchester, MA 01890

  31 Edward Dr, Winchester, MA 01890
• 

  

  

  /35

  $1,599,000

  • 6 Beds
  • 2.5 Baths
  • 3,543 Sq Ft

  189 Mystic Valley Pkwy, Winchester, MA 01890

  Great price improvement - Motivated sellers. Ready to go at this price! Nestled in the heart of downtown Winchester, the stunning Barstow House boasts a unique Mansard roof & timeless colonial architecture. This historic gem features a versatile floorplan designed for modern living while preserving its classic charm. The first level beautifully blends form & function; the home office, mudroom, a

  Anne Spry Barrett Sotheby's International Realty

  189 Mystic Valley Pkwy, Winchester, MA 01890
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  /36

  $1,875,000 Sold Dec 23, 2024

  • 3,376 Sq Ft
  • $555/SF
  • 28 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1925

  10 Marshall Rd, Winchester, MA 01890

  Fully renovated in 2012,this charming colonial is nestled on a side street near Winchester Center, both train stations and local schools.Step into a welcoming ,traditional foyer that leads to the living room, complete with custom built-ins, a cozy fireplace and French doors opening to a sunroom bathed in natural light. The chefs kitchen boasts high end appliances and flows seamlessly into a

  Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

  10 Marshall Rd, Winchester, MA 01890
• 

  

  /37

  Est $846,546 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft

  47 Edward Dr, Winchester, MA 01890

  47 Edward Dr, 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
• 

  

  /25

  $1,000,000 Sold Dec 19, 2024

  • 1,840 Sq Ft
  • $543/SF
  • 8 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1937

  15 Westland Ave, Winchester, MA 01890

  A dIamond in the rough!!! Are you a contractor or handy end user looking for a project in sought after WInchester? Look no further than this 1937, 4 bedroom Colonial brimming with potential. The charm of yesteryear shows through with custom built-ins, crown moldings, hardwood flooring and so much more. Full walk out unfinished basement with double soapstone sink and a full walk up attic lends

  Libby Rankin Hamill Berkshire Hathaway HomeServices Stephan Real Estate

  15 Westland Ave, Winchester, MA 01890
• 

  

  /31

  Est $1,813,473 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,028 Sq Ft

  56 Ridge St, Winchester, MA 01890

  56 Ridge St, Winchester, MA 01890
• 

  

  /42

  $1,399,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,141 Sq Ft

  117 Mount Vernon St, Winchester, MA 01890

  Available for the first time in over four decades and nestled just footsteps from Winchester Center, welcome to 117 Mount Vernon Street! As you enter, you are greeted by tall ceilings adorned with beautiful molding and a flood of natural light that fills the space with warmth and tranquility. The home offers three spacious bedrooms, including a flexible primary suite that boasts an adjoining

  Philip Vita Compass

  117 Mount Vernon St, Winchester, MA 01890
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  /27

  $2,120,000 Sold Dec 19, 2024

  • 4,255 Sq Ft
  • $498/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  2 Loring Ct, Winchester, MA 01890

  UNDER CONSTRUCTION to be completed by 11/24! Desirable 4+ bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open floor plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating, quartz countertops, high-end appliances and walk in pantry. Off the kitchen is a spacious family room w/gas

  Kim Covino Compass

  2 Loring Ct, Winchester, MA 01890
• 

  

  /23

  Est $966,649 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,548 Sq Ft

  12 James St, Winchester, MA 01890

  12 James St, Winchester, MA 01890
• 

  

  /15

  $965,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,333 Sq Ft

  48 Tremont St, Winchester, MA 01890

  Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom with laundry, front-to-back fire-placed living

  Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

  48 Tremont St, Winchester, MA 01890
• 

  

  /37

  $2,150,000 Sold Dec 18, 2024

  • 3,048 Sq Ft
  • $705/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1963

  18 Dix St, Winchester, MA 01890

  Elegant and timeless, this beautifully renovated colonial in the heart of Winchester Center offers the perfect blend of classic design and modern luxury. With a high-end chef’s kitchen featuring an oversized island, the home’s open floor plan seamlessly connects to a spacious family room and dining area, ideal for gatherings. The first floor also boasts a formal front-to-back living room with a

  Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

  18 Dix St, Winchester, MA 01890
• 

  

  /38

  Est $1,224,584 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,827 Sq Ft

  10 James St, Winchester, MA 01890

  10 James St, Winchester, MA 01890
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  /42

  $2,499,000 Pending

  • 6 Beds
  • 3.5 Baths
  • 4,212 Sq Ft

  19 Yale St, Winchester, MA 01890

  Welcome to the Flats, where elegance and charm abound, the neighborhood is the one everyone aspires to. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom

  Nancy Pallotta Advisors Living - Winchester

  19 Yale St, Winchester, MA 01890
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  /24

  $962,000 Sold Dec 18, 2024

  • 1,890 Sq Ft
  • $509/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  25 Hemingway St, Winchester, MA 01890

  Discover the potential of this charming and well-maintained 2-story Cape-style home, offering both comfort and privacy in a highly desirable Winchester location. Conveniently situated near a public elementary school, public transportation, healthcare services, and a variety of dining options, this home ensures easy access to everything you need. Featuring 3 spacious bedrooms and 2 full baths, the

  Andersen Group Realty Keller Williams Realty Boston Northwest

  25 Hemingway St, Winchester, MA 01890
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  /33

  Est $1,108,026 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft

  180 Dothan St, Winchester, MA 01890

  180 Dothan St, Winchester, MA 01890
• 

  

  /23

  $1,199,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,520 Sq Ft

  10 Allen Rd, Winchester, MA 01890

  Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the

  Sally Baldwin Coldwell Banker Realty - Lexington

  10 Allen Rd, Winchester, MA 01890
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  /26

  $1,725,000 Sold Dec 18, 2024

  • 3,143 Sq Ft
  • $549/SF
  • 75 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1939

  7 Ardley Rd, Winchester, MA 01890

  Spacious 4-bedroom colonial home w/a Nantucket vibe, sited on manicured lawns in a cul-de-sac neighborhood! Just a block from the newly being built elementary school, close to the bike path, Horn Pond & hiking trails, this property is sure to please! 7 Ardley Road features a flowing & welcoming floor plan w/lots of natural light. Beautiful gleaming hardwood flooring is found in the living room

  Vantage Point Team William Raveis R.E. & Home Services

  7 Ardley Rd, Winchester, MA 01890
• 

  

  /42

  Est $907,363 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,890 Sq Ft

  25 Henry St, Winchester, MA 01890

  25 Henry St, Winchester, MA 01890
• 

  

  /40

  $1,499,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,351 Sq Ft

  19 Cox Rd, Winchester, MA 01890

  Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen with newer appliances leads to the open concept dining room overlooking the beautiful, private yard. The spacious living room features a fplc & bay window; a sunroom, 3 spacious bedrooms, 1 bath & garage complete the main level; the lower level offers a large rec/ family room w

  Kim Covino Compass

  19 Cox Rd, Winchester, MA 01890
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  /37

  $773,000 Sold Dec 16, 2024

  • 1,430 Sq Ft
  • $541/SF
  • 13 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  171 Swanton St Unit 16, Winchester, MA 01890

  Welcome to this fabulous sought after end unit townhouse located at The Village,close to town,schools, and conservation.This home has been meticulously maintained and updated including new windows. Inviting living room has gas fireplace and private seating area with skylight looking over a private wooded setting and patio. Kitchen has cherry custom cabinets with granite and stainless

  Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

  171 Swanton St Unit 16, Winchester, MA 01890
• 

  

  /26

  Est $829,227 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,279 Sq Ft

  28 Henry St, Winchester, MA 01890

  28 Henry St, Winchester, MA 01890
• 

  

  /36

  $749,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,545 Sq Ft

  7 Conant Rd Unit 34, Winchester, MA 01890

  Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step-free front entrance—an ideal setup for everyday convenience. This beautifully maintained first-floor unit offers the perfect blend of comfort, style, and accessibility. Inside, you'll find two generously sized bedrooms, including a spacious en-suite with direct access to one of

  Melanie Lentini Leading Edge Real Estate

  7 Conant Rd Unit 34, Winchester, MA 01890
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  /34

  $2,960,000 Sold Dec 12, 2024

  • 4,860 Sq Ft
  • $609/SF
  • 72 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2024

  39 Everett Ave, Winchester, MA 01890

  Welcome to this stunning, brand-new construction in Winchester's most desired neighborhood. This home offers modern luxury and timeless elegance. The custom kitchen features two-toned countertops with a Pegasus marble island and Jet Mist granite perimeter, along with brass accents. The pantry provides for ample additional storage with floor to ceiling cabinets, jet mist counters and a wine

  Mark Donnellan Advisors Living - Winchester

  39 Everett Ave, Winchester, MA 01890
• 

  

  /20

  Est $1,058,066 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  14 Locke St, Winchester, MA 01890

  14 Locke St, Winchester, MA 01890
• 

  

  /37

  $1,595,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,763 Sq Ft

  7 Wainwright Rd Unit 8, Winchester, MA 01890

  Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large

  Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

  7 Wainwright Rd Unit 8, Winchester, MA 01890
• 

  

  /37

  $2,750,000 Sold Dec 12, 2024

  • 4,212 Sq Ft
  • $653/SF
  • 21 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1935

  56 Salisbury St, Winchester, MA 01890

  Beautifully renovated 4 bedroom home in sought after Winchester Flats! Featuring a picturesque combination of stylish comfort and modern design. The 1st floor welcomes with an oversized custom mudroom leading to a spacious chef's kitchen featuring upgraded Wolf appliances including gas range, steam oven, and 2 built-in beverage fridges. The family room invites with custom built-in window seats,

  The McLaren D'Agostino Team Compass

  56 Salisbury St, Winchester, MA 01890
• 

  

  /17

  Est $2,035,924 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,578 Sq Ft

  21 Dunster Ln, Winchester, MA 01890

  21 Dunster Ln, Winchester, MA 01890
• 

  

  /33

  $699,900 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,326 Sq Ft

  32 Clark St, Winchester, MA 01890

  A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a home to their liking, this residence presents the perfect blend of potential and location. This 2 bedroom single family home makes for a great condo alternative. Don't miss this rare chance to break into the Winchester market and enjoy all this town has to offer from it's great

  Rodrigo Serrano Leading Edge Real Estate

  32 Clark St, Winchester, MA 01890
• 

  

  /38

  $1,650,000 Sold Dec 11, 2024

  • 3,158 Sq Ft
  • $522/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  31 Girard Rd, Winchester, MA 01890

  Welcome to 31 Girard Road, a lovely colonial gracefully positioned on a prominent corner lot in the Vinson Owen School district! As you step inside, you’ll pass an exquisite curved staircase on your way to the front-to-back living room with custom built-ins. The heart of the home is the open kitchen, seamlessly connected to a bright and airy dining area. This space is perfect for hosting

  Philip Vita Compass

  31 Girard Rd, Winchester, MA 01890
• 

  

  /37

  Est $2,015,783 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,346 Sq Ft

  6 Ridge St, Winchester, MA 01890

  6 Ridge St, Winchester, MA 01890
• 

  

  /40

  $1,375,000 Pending

  • 3 Beds
  • 2 Baths
  • 3,406 Sq Ft

  7 Hutchinson Rd, Winchester, MA 01890

  A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a generous lot, this unique home has been lovingly maintained and is full of potential; ready for updates & your personal touch! The floor plan provides a flexible layout that’s ideal for easy living with a spacious first-floor bedroom, full bath, an oversized home office or add'l

  Kim Covino Compass

  7 Hutchinson Rd, Winchester, MA 01890
• 

  

  /42

  $1,755,000 Sold Dec 10, 2024

  • 2,886 Sq Ft
  • $608/SF
  • 7 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1911

  19 Warren St, Winchester, MA 01890

  Step into this beautifully designed 3-bedroom, 3-bathroom single-family home located in the sought-after Flats of Winchester. Nestled in a wonderful neighborhood, this home offers a perfect blend of charm and modern living. The spacious living room with a cozy fireplace flows seamlessly into a bright sunroom, filling the space with natural light. The eat-in kitchen is equipped with stainless

  Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

  19 Warren St, Winchester, MA 01890
• 

  

  /38

  Est $1,164,381 Not Listed For Sale

  • 5 Beds
  • 1.5 Baths
  • 2,383 Sq Ft

  18 Ridge St, Winchester, MA 01890

  18 Ridge St, Winchester, MA 01890
• 

  

  /11

  $1,269,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,136 Sq Ft

  158 Swanton St Unit 160, Winchester, MA 01890

  Welcome to 158 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

  Monte Marrocco Coldwell Banker Realty - Lexington

  158 Swanton St Unit 160, Winchester, MA 01890
• 

  

  /40

  $1,225,000 Sold Dec 09, 2024

  • 3,350 Sq Ft
  • $366/SF
  • 27 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1988

  7 Wainwright Rd Unit 29, Winchester, MA 01890

  Imagine arriving home to peace & serenity at The Ledges, a hilltop oasis on Winchester's West side. This tranquil retreat offers carefree living & your private sanctuary. Relax in the fireplace living room, sliders to your private deck & expansive views. The main bedroom en suite, is conveniently located on the first floor. Second level finds a loft, skylit bonus room perfect for a home office,

  Joanne Sexeny Coldwell Banker Realty - Lexington

  7 Wainwright Rd Unit 29, Winchester, MA 01890
• 

  

  /41

  Est $1,956,204 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,730 Sq Ft

  2 Tanglewood Ln, Winchester, MA 01890

  2 Tanglewood Ln, Winchester, MA 01890

Showing Results 161 - 200, Page 5 of 18