Winchester, MA Homes

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  $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
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  Explore Winchester

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  /9

  $1,890 per month plus fees

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

  200 Swanton St Unit 708, Winchester, MA 01890

  Available Oct 1Bright and inviting top-floor studio condo at the sought-after Parkview community. This unit features a private balcony overlooking the pond, perfect for enjoying peaceful views. Rent includes heat, hot water, electricity, and air conditioning for added convenience. Residents benefit from on-site laundry, parking, and access to the community pool. A well-maintained building in a

  

  Joan Powell

  Advisors Living - Merrimac

  (781) 653-7188

  200 Swanton St Unit 708, Winchester, MA 01890
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  /42

  $1,725,000 Sold Sep 19, 2025

  • 2,541 Sq Ft
  • $679/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1960

  9 Pilgrim Dr, Winchester, MA 01890

  Welcome to this beautiful split-level home nestled on a desirable corner lot in Winchester’s sought after west side. Featuring gleaming hardwood floors throughout, this home offers a perfect blend of comfort and style. The main level boasts an open floor plan connecting the dining room, kitchen, and living room, and seamlessly flows into a stunning vaulted family room, perfect for both everyday

  McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

  9 Pilgrim Dr, Winchester, MA 01890
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  /24

  Est $296,714 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 394 Sq Ft

  200 Swanton St Unit 502, Winchester, MA 01890

  200 Swanton St Unit 502, Winchester, MA 01890
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  /35

  $2,399,000

  • 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
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  /20

  $2,249 - $9,297 total monthly price

  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
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  /31

  $1,465,000 Sold Sep 18, 2025

  • 2,506 Sq Ft
  • $585/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1974

  6 Highland Ave, Winchester, MA 01890

  4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is

  Peter Rooney Compass

  6 Highland Ave, Winchester, MA 01890
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  /39

  Est $2,334,620 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
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  $2,399,000 Open Sun 11AM - 12PM

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  14 Grant Rd, Winchester, MA 01890

  Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space

  Monte Marrocco Coldwell Banker Realty - Lexington

  14 Grant Rd, Winchester, MA 01890
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  /29

  $3,800 per month plus fees

  • 2 Beds
  • 1.5 Baths
  • 896 Sq Ft
  • Apartment for Rent

  40 Dunster Ln Unit 1, Winchester, MA 01890

  Welcome to this charming, sun-filled 2-bed, 2-bath home in the heart of Winchester. With nearly 900 sq. ft. of living space, it blends classic New England charm with modern convenience. The house comes fully furnished—down to the silverware, linens, and decor—so you can simply unpack and relax. Enjoy hardwood floors, a bright living room, a modern kitchen with upgraded counters, and a private

  William Dynan Keller Williams Realty Evolution

  40 Dunster Ln Unit 1, Winchester, MA 01890
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  /36

  $1,945,000 Sold Sep 16, 2025

  • 3,825 Sq Ft
  • $508/SF
  • 7 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2025

  20 Grayson Rd, Winchester, MA 01890

  Another Tree Top Group masterpiece—where natural light, luxury finishes, & thoughtful design come together in perfect harmony. This 5-bed, 4.5-bath new construction home boasts 9+ ft ceilings, exceptional light fixtures, and a stunning waterfall center island that anchors the designer kitchen w/ custom cabinetry that extends to the ceiling. Custom built-ins & storage throughout. A sleek linear

  Monte Marrocco Coldwell Banker Realty - Lexington

  20 Grayson Rd, Winchester, MA 01890
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  /33

  Est $1,723,238 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
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  /40

  $2,999,999

  • 5 Beds
  • 4.5 Baths
  • 5,716 Sq Ft

  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
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  /24

  $3,275 - $7,774 total monthly price

  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
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  /32

  $505,000 Sold Sep 15, 2025

  • 822 Sq Ft
  • $614/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1966

  200 Swanton St Unit 239, Winchester, MA 01890

  Sunny second-floor 2-bedroom unit overlooking a serene duck pond. This home features an open layout with hardwood floors, an updated granite and stainless-steel kitchen, and a modern bath with a sleek barn door. Each bedroom offers two closets, plus three additional hallway closets for exceptional storage. Enjoy a private enclosed balcony with serene views. The HOA fee includes heat, hot water,

  Joan Powell Advisors Living - Merrimac

  200 Swanton St Unit 239, Winchester, MA 01890
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  /42

  Est $2,890,710 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
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  /40

  $2,199,000

  • 5 Beds
  • 3.5 Baths
  • 6,232 Sq Ft

  5 Azalea Rd, Winchester, MA 01890

  NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  5 Azalea Rd, Winchester, MA 01890
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  /15

  $2,500 per month plus fees

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  343 Washington St Unit 343, Winchester, MA 01890

  Sunny 2-Bedroom in Winchester! Beautifully maintained 5-room apartment featuring 2 bedrooms, 1 bath, and parking for 2 cars. This first-floor unit offers gleaming hardwood floors throughout, a bright kitchen with dishwasher and spacious pantry, and a dining room with built-in cabinet and charming chandelier. Two generously sized bedrooms with closets, a full bath, and both front (enclosed) and

  Danielle Storella Berkshire Hathaway HomeServices Commonwealth Real Estate

  343 Washington St Unit 343, Winchester, MA 01890
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  /39

  $1,770,000 Sold Sep 12, 2025

  • 2,850 Sq Ft
  • $621/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2012

  178 Mystic Valley Pkwy, Winchester, MA 01890

  This carefully crafted Colonial, custom-built by Andrew Pywell, combines solid construction with a bounty of special touches and timeless charm. Delight in sun-splashed living spaces, gleaming hardwood floors, crown moldings, and a layout that balances an open flow, defined spaces and beautifully proportioned rooms across 2,850 square feet. The gracious formal living room, dining room, and

  Katherine Waters-Clark Compass

  178 Mystic Valley Pkwy, Winchester, MA 01890
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  /40

  Est $1,362,897 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
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  /39

  $2,695,000

  • 5 Beds
  • 3.5 Baths
  • 4,779 Sq Ft

  48 Salisbury St, Winchester, MA 01890

  Thoughtfully renovated & meticulously maintained, this classic colonial home in the Flats invites with timeless charm & modern conveniences. Through the center entrance be welcomed into the fireplaced living room & dining room- both refreshed in 2025 with new lighting, paint & wallpaper. The open-plan custom kitchen with marble counters, stainless appliances, and a butler’s pantry with sink,

  Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

  48 Salisbury St, Winchester, MA 01890
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  $2,200 total monthly price

  • 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 11-02-2025.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

  2 Elmwood Ave Unit 11, Winchester, MA 01890
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  /40

  $1,100,000 Sold Sep 12, 2025

  • 1,414 Sq Ft
  • $778/SF
  • 8 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  5 Cutting St, Winchester, MA 01890

  OFFER DEADLINE TUE JULY 29th 5:00PM | Exceedingly charming + in-town location to be envied. Shops, schools + both MBTA stations at your fingertips. Step up onto your porch, pass the bench swing you’re yet to install; entering into the inviting foyer w/ original stairs preserved & tall ceilings. The main level is sophisticated & functional. A front facing dining room w/ plantation shutters +

  Oliver Koester Compass

  5 Cutting St, Winchester, MA 01890
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  /33

  Est $1,508,916 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
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  /42

  $2,099,000

  • 6 Beds
  • 3.5 Baths
  • 3,521 Sq Ft

  19 Glengarry Rd, Winchester, MA 01890

  A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personalize & create their dream home. Nestled in a top neighborhood near wedge pond, the home boasts classic

  Kim Covino Compass

  19 Glengarry Rd, Winchester, MA 01890
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  /25

  $7,000 per month plus fees

  • 3 Beds
  • 3 Baths
  • 2,443 Sq Ft
  • House for Rent

  25 Berkshire Dr, Winchester, MA 01890

  No broker fee. Pets Negotiable. This beautifully renovated home offers over 2,400 square feet of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today’s lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with

  Nadia Mounsif Coldwell Banker Realty - Cambridge

  25 Berkshire Dr, Winchester, MA 01890
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  $1,525,000 Sold Sep 12, 2025

  • 2,755 Sq Ft
  • $554/SF
  • 30 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1929

  5 Thornton Rd, Winchester, MA 01890

  This stately home near the Flats blends original character with modern-day living, 8' ceilings and awaits your personal touches. The living room features stunning woodwork, a fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen.

  Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

  5 Thornton Rd, Winchester, MA 01890
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  /42

  Est $1,438,324 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,125 Sq Ft

  47 Thornberry Rd, Winchester, MA 01890

  47 Thornberry Rd, Winchester, MA 01890
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  /42

  $2,689,000

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

  382 S Border Rd, Winchester, MA 01890

  NEW HIGH-END CONSTRUCTION - 12 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 Advisors Living - Winchester

  382 S Border Rd, Winchester, MA 01890
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  /4

  $2,000 total monthly price

  • 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
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  /7

  $3,450,000 Sold Sep 11, 2025

  • 4,800 Sq Ft
  • $719/SF
  • 151 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1932

  58 Wedgemere Ave, Winchester, MA 01890

  Experience the timeless charm of this stunning English Tudor in Winchester’s coveted Flats neighborhood. Set on an oversized lot with mature landscaping, this home is undergoing a full renovation and expansion by Mark Stephen Development, blending classic elegance with modern luxury. The reimagined design features two fireplaces, an expansive family room, living room, dining room, first- and

  Mark Donnellan Advisors Living - Winchester

  58 Wedgemere Ave, Winchester, MA 01890
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  Est $1,677,777 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
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  /42

  $2,245,000

  • 6 Beds
  • 4 Baths
  • 4,385 Sq Ft

  5 Bacon St, Winchester, MA 01890

  This stunning Victorian home, in the style of Painted Ladies with soaring ceilings & hardwood floors, is in a prime neighborhood just moments from Winchester Center, the commuter rail, Shannon Beach, & a short ride to the Airport & downtown Boston. The house lives as a harmonious single family with an inlaw apartment on the 1st floor. It has 6 beds & 4 baths, over 4,385 SF of living area on 3

  Anne Spry Barrett Sotheby's International Realty

  5 Bacon St, Winchester, MA 01890
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  /29

  $7,500 per month plus fees

  • 3 Beds
  • 3.5 Baths
  • 3,218 Sq Ft
  • House for Rent

  29 Wainwright Rd, Winchester, MA 01890

  Picture-perfect single-family home in Winchester, just 8 miles north of Boston, but in a world of its own. This light-filled home features a large kitchen with stainless steel appliances and granite countertops opening to the dining area, living room, family room and extra-large office on first floor with a treehouse feel outdoor patio. Second level has primary bedroom and ensuite bath and 2

  Helen Stefan Gibson Sotheby's International Realty

  29 Wainwright Rd, Winchester, MA 01890
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  $710,000 Sold Sep 10, 2025

  • 1,170 Sq Ft
  • $607/SF
  • 50 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1982

  666 Main St Unit 206, Winchester, MA 01890

  Back on Market - buyer got cold feet. Welcome to Wedgewood Place at 666 Main Street in Winchester Center - a perfect blend of small-town charm and urban convenience. This desirable and well-maintained 2 bed/2 bath home comes with 1 covered parking. Enjoy a spacious open-concept layout with a wood-burning fireplace, screened-in balcony overlooking courtyard & pool, and updated kitchen and guest

  Sveta Vakhitova Berkshire Hathaway HomeServices Warren Residential

  666 Main St Unit 206, Winchester, MA 01890
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  /36

  Est $1,602,532 Not Listed For Sale

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

  94 Johnson Rd, Winchester, MA 01890

  94 Johnson Rd, Winchester, MA 01890
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  $2,239,000 Open Sun 2:30PM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 4,798 Sq Ft

  61 Grove St, Winchester, MA 01890

  - 2017 - STUNNING CUSTOM- BUILT HOME, COMPLETELY rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. Welcome to this easy living, maintenance free sophisticated residence. FIRST FLOOR LUXURIOUS SUITE with a LARGE BEDROOM, marble bath w/double sink vanity, walk in shower & soaking tub. An exquisite kitchen with granite island, counters and back splash, All Bosch

  Dorothea Feffer Coldwell Banker Realty - Lexington

  61 Grove St, Winchester, MA 01890
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  /40

  $3,800 total monthly price

  • 4 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • Townhouse for Rent

  848 Main St, Winchester, MA 01890

  **Elegant Winchester Home Near Wright Pond and Downtown Amenities**Spacious 4-bedroom, 1.5-bathroom townhouse style unit - located close to Winchester Center, with a park across the street and Wright Pond and Park nearby.Enjoy top rated Winchester schools nearby.Open-concept kitchen with granite countertops, island, pantry, and space for your table, plus hardwood floors, central

  848 Main St, Winchester, MA 01890
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  $740,000 Sold Sep 09, 2025

  • 1,358 Sq Ft
  • $545/SF
  • 8 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1903

  15 Governors Ave Unit 1, Winchester, MA 01890

  Turn-key 3-bed condo offers effortless living just moments from downtown Winchester, Muraco School, & Middlesex Fells—nothing to do but unpack your bags & settle in. The main level offers a spacious entry area that functions well as a mudroom or sitting room, along with a sunny living room, dining room, & renovated kitchen featuring granite counters, center island, ss appliances, Sub-Zero fridge,

  Pirani & Wile Group Advisors Living - Winchester

  15 Governors Ave Unit 1, Winchester, MA 01890
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  /32

  Est $1,654,432 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  104 Thornberry Rd, Winchester, MA 01890

  104 Thornberry Rd, Winchester, MA 01890

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