Winchester, MA Homes

• 

  

  

  /18

  $385,000 Open Sat 10:30AM - 12PM

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft

  200 Swanton St Unit T28, Winchester, MA 01890

  Beautiful terrace-level 1-bedroom condo at Parkview Condos in Winchester! This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with

  

  Joan Powell

  RE/MAX Andrew Realty Services

  (781) 384-5553

  200 Swanton St Unit T28, Winchester, MA 01890
• Explore Winchester

• 

  

  

  /13

  $3,795 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Apartment for Rent

  7 Lewis Rd Unit 2, Winchester, MA 01890

  Wonderful opportunity to rent in Winchester, less than a half mile from the town common. Rarely available First floor unit with hardwood floors throughout, 2 bedrooms and one full tiled bath. Additional storage space in lower level that is wired to your specific unit...could be used for office space, home gym, craft room, etc. Carefree living with Heat, basic cable tv and all exterior maintenance

  

  Catherine Albiani

  Better Homes and Gardens Real Estate - The Shanahan Group

  (781) 404-8664

  7 Lewis Rd Unit 2, Winchester, MA 01890
• 

  

  

  /40

  $1,600,000 Sold Nov 07, 2025

  • 3,591 Sq Ft
  • $446/SF
  • 8 Days On Market

  • 8 Beds
  • 2.5 Baths
  • Built 1880

  112 Church St, Winchester, MA 01890

  Rare Opportunity: Spacious Side-by-Side Two-Family Home Less Than 1 Mile from Town Center. This charming two-family home offers classic period details, including fireplaced living rooms, formal dining rooms with built-in china cabinets located directly off the kitchen. Each unit features two large bedrooms with hardwood floors and a full bath on the second floor, plus two additional bedrooms and

  Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

  112 Church St, Winchester, MA 01890
• 

  

  

  /19

  Est $286,731 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft

  200 Swanton St Unit T8, Winchester, MA 01890

  200 Swanton St Unit T8, Winchester, MA 01890
• 

  

  

  /41

  $1,990,000

  • 4 Beds
  • 4.5 Baths
  • 4,474 Sq Ft

  4 Chestnut St, Winchester, MA 01890

  Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blue cabinetry, copper accents, and bold designer touches. One bedroom opens to a composite deck

  

  Tyson Lynch

  The Proper Nest Real Estate

  (781) 633-6582

  4 Chestnut St, Winchester, MA 01890
• 

  

  /20

  $2,358 - $20,886 per month plus fees

  Sanctuary Winchester West

  Studio - 3 Beds

  416 Cambridge St, Winchester, MA 01890

  The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

  416 Cambridge St, Winchester, MA 01890
• 

  

  /41

  $2,150,000 Sold Nov 05, 2025

  • 3,512 Sq Ft
  • $612/SF
  • 7 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1989

  7 Wainwright Rd Unit 72, Winchester, MA 01890

  Extensively renovated and move-in ready, this stunning F-unit townhouse offers 4 bedrooms and 4.5 baths with impeccable detail and modern appeal throughout. The many windows, high ceilings, gleaming hardwood floors, and open design create a warm sun-filled home. You will enjoy the large kitchen and the ability to retreat to the dazzling first-floor primary suite, which provides single floor

  Pirani & Wile Group Gibson Sotheby's International Realty

  7 Wainwright Rd Unit 72, Winchester, MA 01890
• 

  

  /12

  Est $355,391 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 602 Sq Ft

  200 Swanton St Unit L32, Winchester, MA 01890

  200 Swanton St Unit L32, Winchester, MA 01890
• 

  

  /42

  $2,599,000 Pending

  • 6 Beds
  • 5.5 Baths
  • 4,563 Sq Ft

  382 S Border Rd, Winchester, MA 01890

  NEW HIGH-END CONSTRUCTION - 13 Rms - 6 BD's - 5.5 BA's You will be captivated by the grand entrance - attention to detail - high coffered 10' ceilings and excellent flow that leads you to the magnificent Open Floor Plan - custom-designed Kitchen which is the heart of this home. no expense was spared; custom Cabinets, Thermador appliances, oversized Center Island; Living Rm/Great Rm w/FP, Dining

  Lucille Murray Gibson Sotheby's International Realty

  382 S Border Rd, Winchester, MA 01890
• 

  

  /36

  $6,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,900 Sq Ft
  • Apartment for Rent

  846 Main St Unit 301, Winchester, MA 01890

  No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

  Anthony Marino The Marino Group Collection

  846 Main St Unit 301, Winchester, MA 01890
• 

  

  /42

  $1,750,000 Sold Oct 31, 2025

  • 2,397 Sq Ft
  • $730/SF
  • 1 Day On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1937

  15 Westland Ave, Winchester, MA 01890

  OFFER ACCEPTED OH SUNDAY CANCELLED Taken down to the studs, this renovated and reimagined center entrance Colonial offers timeless elegance and modern comfort in one of Winchester’s most desirable neighborhoods. The gracious foyer gives way to a front-to-back living room anchored by a wood-burning fireplace with custom mantle. An adjacent sun-filled, south-facing room provides the perfect space

  Erica Carson Coldwell Banker Realty - Lexington

  15 Westland Ave, Winchester, MA 01890
• 

  

  /39

  Est $2,335,271 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 4,539 Sq Ft

  38 Winthrop Street Extension, Winchester, MA 01890

  38 Winthrop Street Extension, Winchester, MA 01890
• 

  

  /42

  $2,075,000 Open Sun 12PM - 1:30PM

  • 4 Beds
  • 2.5 Baths
  • 3,658 Sq Ft

  8 Felsdale Close, Winchester, MA 01890

  Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells' scenic trails, the setting is both serene and convenient. Designed by renowned architect Harry M.

  Anne Spry Barrett Sotheby's International Realty

  8 Felsdale Close, Winchester, MA 01890
• 

  

  /24

  $2,650 - $9,668 per month plus fees

  Sanctuary Winchester North

  1 - 3 Beds

  25-35 River St, Winchester, MA 01890

  The Sanctuary at Winchester North is designed for the way you live - casual fireside gatherings in the Den, a game of billiards in the Hive, a meal with friends prepared in the Nest's Chef's Kitchen. Maybe you prefer to make a splash in the pool, or stay on track with personal health goals in the fitness and health facility. With meticulously appointed common spaces designed for work, play, and

  25-35 River St, Winchester, MA 01890
• 

  

  /42

  $1,550,000 Sold Oct 31, 2025

  • 2,995 Sq Ft
  • $518/SF
  • 5 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1960

  205 Ridge St, Winchester, MA 01890

  Welcome to 205 Ridge Street, a stunning residence that blends timeless elegance with modern comfort, perfectly designed for today’s lifestyle. Nestled in one of Winchester’s most desirable neighborhoods, this five-bedroom, three-bath home offers the perfect balance of refined living and everyday convenience. From the moment you arrive, the property’s curb appeal and thoughtful details set the

  Debby Valdes eXp Realty

  205 Ridge St, Winchester, MA 01890
• 

  

  /34

  Est $843,399 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  897 Main St Unit 1, Winchester, MA 01890

  897 Main St Unit 1, Winchester, MA 01890
• 

  

  /42

  $2,299,000 Open Sat 12PM - 1:30PM

  • 3 Beds
  • 2.5 Baths
  • 3,953 Sq Ft

  19 Gershon Way, Winchester, MA 01890

  Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

  Philip Vita Compass

  19 Gershon Way, Winchester, MA 01890
• 

  

  /27

  $3,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,338 Sq Ft
  • Condo for Rent

  7 Conant Rd Unit 21, Winchester, MA 01890

  Welcome to 7 Conant Road! This unit offers a spacious open floor plan with 1,338 square feet, featuring two bedrooms and two full bathrooms, including a roomy primary suite. Enjoy open concept living with nice flow from the kitchen to the living room & dining area. Updated & move-in ready, the bedrooms are large, complete with generous closet space. This rental showcases modern charm with an

  Kim Covino Compass

  7 Conant Rd Unit 21, Winchester, MA 01890
• 

  

  /40

  $2,895,000 Sold Oct 30, 2025

  • 5,716 Sq Ft
  • $506/SF
  • 28 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2025

  6 Abby Rd, Winchester, MA 01890

  Here's a rare opportunity to own a spectacular new construction home by a premier local builder on a BRAND-NEW road. This property stands prominently on its lot, overlooking a lush wooded area with close proximity to “The Fells”. The first floor is designed for both entertaining and everyday living, featuring formal dining, a designer kitchen with a butler's pantry, and a fireplaced family room

  Philip Vita Compass

  6 Abby Rd, Winchester, MA 01890
• 

  

  /33

  Est $1,704,114 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,254 Sq Ft

  20 Graystone Cir Unit 20, Winchester, MA 01890

  20 Graystone Cir Unit 20, Winchester, MA 01890
• 

  

  /35

  $2,149,000 Open Sat 1PM - 2:30PM

  • 5 Beds
  • 4 Baths
  • 4,334 Sq Ft

  237 Swanton St, Winchester, MA 01890

  NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas

  Kim Covino Compass

  237 Swanton St, Winchester, MA 01890
• 

  

  /7

  $2,100 per month plus fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  2 Elmwood Ave Unit 11, Winchester, MA 01890

  This nice 1 Bedroom 1 Bath place in the WINCHESTER area is available for Now.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions at the time the information was obtained.

  2 Elmwood Ave Unit 11, Winchester, MA 01890
• 

  

  /38

  $2,000,000 Sold Oct 29, 2025

  • 5,000 Sq Ft
  • $400/SF
  • 3 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1968

  1 Fox Hunt Ln, Winchester, MA 01890

  Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lot on a quiet cul-de-sac near Winchester Country Club. The first floor features a welcoming formal living room just off the entry, a spacious primary suite with two walk-in closets and a private bath, a guest bedroom with en-suite bath, and a third bedroom or home office.

  Leigh Ventura Compass

  1 Fox Hunt Ln, Winchester, MA 01890
• 

  

  /42

  Est $2,869,935 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,265 Sq Ft

  228 Ridge St, Winchester, MA 01890

  228 Ridge St, Winchester, MA 01890
• 

  

  /42

  $1,950,000

  • 3 Beds
  • 2.5 Baths
  • 2,443 Sq Ft

  5 Wood Ln, Winchester, MA 01890

  Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cypress shingle exterior, and classic New England design. Inside, three magnificent fireplaces, exquisite

  Kim Covino Compass

  5 Wood Ln, Winchester, MA 01890
• 

  

  /29

  $5,700 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,575 Sq Ft
  • Condo for Rent

  2 Rangeley Rd Unit 2, Winchester, MA 01890

  Location, Location, Location!! This beautifully updated 2 bedroom 2.5 bath conveniently located in Winchester Center. Recently renovated, this unit boasts a stunning kitchen with farmer sink, high end stainless appliances, custom cabinetry and pantry. First floor offers living room w/ fireplace and large dining room with hardwood throughout. 2 spacious bedrooms and 1.5 baths complete the second

  Kim Covino Compass

  2 Rangeley Rd Unit 2, Winchester, MA 01890
• 

  

  /36

  $2,750,000 Sold Oct 29, 2025

  • 4,627 Sq Ft
  • $594/SF
  • 30 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2025

  11 Taft Dr, Winchester, MA 01890

  Open house canceled! Offer accepted! Luxury, location, and lifestyle come together in this beautiful new 5-bed, 5.5-bath home in Winchester’s sought-after Westside. Just steps to Ambrose School, one block from the Alewife bus stop, a short stroll to the commuter rail, and right down the street from the Winchester Boat Club, this home offers unmatched convenience and charm. Inside, enjoy over

  Rose Hall Blue Ocean Realty, LLC

  11 Taft Dr, Winchester, MA 01890
• 

  

  /40

  Est $1,375,352 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,529 Sq Ft

  15 Wincrest Dr, Winchester, MA 01890

  15 Wincrest Dr, Winchester, MA 01890
• 

  

  /40

  $2,785,000 Open Sat 12PM - 1:30PM

  • 4 Beds
  • 4 Baths
  • 5,674 Sq Ft

  10 Viking Rd, Winchester, MA 01890

  Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

  Anne Spry Barrett Sotheby's International Realty

  10 Viking Rd, Winchester, MA 01890
• 

  

  /16

  $1,850 per month plus fees

  • Studio
  • 1 Bath
  • Condo for Rent

  2 Elmwood Ave Unit 14, Winchester, MA 01890

  This nice Studio 1 Bath place in the WINCHESTER area is available for Now.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions at the time the information was obtained. We

  2 Elmwood Ave Unit 14, Winchester, MA 01890
• 

  

  /41

  $3,900,000 Sold Oct 24, 2025

  • 5,069 Sq Ft
  • $769/SF
  • 2 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2016

  12 Ledgewood Rd, Winchester, MA 01890

  A rare Winchester offering set on an acre in a wooded enclave of luxury homes near town center. Custom-built, this 5-bedroom, 4.5-bath residence combines timeless design with balanced proportions across four levels. The primary suite includes a private deck, spa-like bath with soaking tub, and gas fireplace. The chef’s kitchen features quarter-sawn oak cabinetry, high-end appliances, large

  Leigh Ventura Compass

  12 Ledgewood Rd, Winchester, MA 01890
• 

  

  /33

  Est $1,525,632 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,034 Sq Ft

  10 Carriage Ln, Winchester, MA 01890

  10 Carriage Ln, Winchester, MA 01890
• 

  

  /30

  $2,799,000

  • 5 Beds
  • 4 Baths
  • 5,083 Sq Ft

  53 Winford Way, Winchester, MA 01890

  Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient

  Andersen Group Realty Keller Williams Realty Boston Northwest

  53 Winford Way, Winchester, MA 01890
• 

  

  /12

  $2,050 total monthly price

  • 1 Bed
  • 1 Bath
  • 606 Sq Ft
  • Condo for Rent

  200 Swanton St Unit 432, Winchester, MA 01890

  This beautifully maintained one-bedroom condo at Parkview offers exceptional value in Winchester—one of Massachusetts’ most desirable towns. Conveniently located within the building, this bright and inviting unit features a stylish kitchen with granite countertops and modern cabinetry, plus a renovated bathroom with contemporary finishes. Enjoy peaceful views from the private balcony. The

  Alex Wang Hestia

  200 Swanton St Unit 432, Winchester, MA 01890
• 

  

  /42

  $4,450,000 Sold Oct 24, 2025

  • 7,679 Sq Ft
  • $580/SF
  • 1 Day On Market

  • 5 Beds
  • 7 Baths
  • Built 1937

  20 Foxcroft Rd, Winchester, MA 01890

  A rare opportunity to own one of The Flats’ most celebrated homes! This 1930s Colonial Revival w/ classic curb appeal & elegant proportions sits on over 1⁄2 acre of estate-like grounds featuring heated pool, patios, pergola & multiple areas for effortless entertaining. Inside, a grand foyer & sweeping staircase introduce gracious rooms w/ exquisite millwork & superb flow, equally suited for

  Carolyn Walsh Better Homes and Gardens Real Estate - The Shanahan Group

  20 Foxcroft Rd, Winchester, MA 01890
• 

  

  /35

  Est $1,710,477 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,926 Sq Ft

  16 Nassau Dr, Winchester, MA 01890

  16 Nassau Dr, Winchester, MA 01890
• 

  

  /42

  $2,275,000 Open Sat 1PM - 2:30PM

  • 6 Beds
  • 2.5 Baths
  • 4,104 Sq Ft

  15 Wildwood St, Winchester, MA 01890

  Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for thoughtful updates to further enhance its value. Step inside to a sun-filled living room w/oversized

  Kim Covino Compass

  15 Wildwood St, Winchester, MA 01890
• 

  

  /27

  $1,850 total monthly price

  • Studio
  • 1 Bath
  • 250 Sq Ft
  • Condo for Rent

  219 Washington St Unit 11, Winchester, MA 01890

  Amazing location right in the heart of Winchester! Close walking distance to downtown. - Utilities INCLUDED! - Off-street parking available- Laundry on-site

  219 Washington St Unit 11, Winchester, MA 01890
• 

  

  /39

  $800,000 Sold Oct 24, 2025

  • 1,545 Sq Ft
  • $518/SF
  • 5 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1982

  62 Vine St Unit 62, Winchester, MA 01890

  Bright & Airy Cottage at Desirable Wedgewood Place in the heart of Winchester! This charming 2-level, 2-bed, 2-bath “cottage” style condo offers convenience of condo living w/ the feel of a single-family home. Sun-filled layout features a wood-burning fireplace w/ brick hearth, built-ins, hardwood floors, and an updated kitchen with new lighting, flooring, stainless fridge, dishwasher, cooktop &

  David Shorey Real Broker MA, LLC

  62 Vine St Unit 62, Winchester, MA 01890
• 

  

  /36

  Est $1,575,493 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,171 Sq Ft

  94 Johnson Rd, Winchester, MA 01890

  94 Johnson Rd, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18