Winchester, MA Homes

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  /42

  $1,999,900 Pending

  • 5 Beds
  • 3.5 Baths
  • 2,860 Sq Ft

  4 Leslie Rd, Winchester, MA 01890

  Set on a lush, private lot, this Royal Barry Wills home blends timeless design with extraordinary gardens. A welcoming mudroom opens to a cathedral-ceiling kitchen with slider framing views of the yard and perennial plantings. The dining room and front-to-back living room with fireplace and custom built-ins each offer sliders that extend living space outdoors and invite natural light throughout

  Anne Spry Barrett Sotheby's International Realty

  4 Leslie Rd, Winchester, MA 01890
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  $2,900 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Condo for Rent

  17 Linden St Unit 17 Linden St, Winchester, MA 01890

  Walk to Winchester center from this 2 bedroom, eat in kitchen with SS appliances and granite countertops, large living room, small office and 1 and 1/2 baths. Hard wood floors laundry hook up (previous tenant left washer/dryer in unit central AC gas heat. 2 off street parking spots.

  17 Linden St Unit 17 Linden St, Winchester, MA 01890
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  $1,580,000 Sold Feb 26, 2026

  10 Trinity Rd, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • Built 1963

  Last Sold Summary

  • 11% Above List Price
  • $748/SF
  • 5 Days On Market

  Current Estimated Value $1,375,802

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  10 Trinity Rd, Winchester, MA 01890
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  /35

  Est $1,620,896 Not Listed For Sale

  16 Nassau Dr, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 2,926 Sq Ft
  • Built 1960

  16 Nassau Dr, Winchester, MA 01890

  Last Sold Summary

  • 11% Above List Price
  • $499/SF
  • 20 Days On Market

  Last Sold Price $1,460,000

  Last Listing Agent Peter Kasseris Serhant
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  /41

  $3,747,000

  • 7 Beds
  • 6 Baths
  • 7,043 Sq Ft

  2 Everett Ave, Winchester, MA 01890

  Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end

  Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

  2 Everett Ave, Winchester, MA 01890
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  $10,000 total monthly price

  • 6 Beds
  • 4.5 Baths
  • 6,583 Sq Ft
  • House for Rent

  282 High St, Winchester, MA 01890

  Fabulous 6 month rental opportunity with full additional in-law suite with private kitchen, bedroom, bath, and laundry. Very generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and

  Anthony Marino The Marino Group Collection

  282 High St, Winchester, MA 01890
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  $2,420,000 Sold Apr 25, 2025

  48 Wedgemere Ave, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 4,173 Sq Ft
  • Built 1914

  Last Sold Summary

  • 8% Above List Price
  • $580/SF
  • 8 Days On Market

  Current Estimated Value $2,424,902

  Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

  48 Wedgemere Ave, Winchester, MA 01890
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  Est $1,552,723 Not Listed For Sale

  94 Johnson Rd, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 3,171 Sq Ft
  • Built 1971

  94 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 11% Above List Price
  • $442/SF
  • 3 Days On Market

  Last Sold Price $1,400,000

  Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group
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  /10

  $3,400,000

  • 6 Beds
  • 5.5 Baths
  • 6,100 Sq Ft

  9 Albamont Rd, Winchester, MA 01890

  Brand new high end construction in prime Winchester location! Currently under construction w/ completion expected late spring 2026. A thoughtfully designed home with immense curb appeal showcasing stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer

  Kim Covino Compass

  9 Albamont Rd, Winchester, MA 01890
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  $4,150 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Condo for Rent

  10 Webster St Unit 1, Winchester, MA 01890

  Amazing 4 bed 2 bath located within close proximity of Winchester Center! This spacious apartment takes up the first floor and lower level of a 2 family, but it has a single-family feel to it! Inside on the first floor, you'll find hardwood floors throughout, a living room, a dining room, two spacious bedrooms, and a great eat-in kitchen featuring a new dishwasher and refrigerator. Downstairs

  10 Webster St Unit 1, Winchester, MA 01890
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  $720,000 Sold Aug 26, 2025

  29 Vine St Unit 7, Winchester, MA 01890

  • 2 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Above List Price
  • $554/SF
  • 4 Days On Market

  Current Estimated Value $726,178

  Last Listing Agent Philip Vita Compass

  29 Vine St Unit 7, Winchester, MA 01890
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  Est $1,588,505 Not Listed For Sale

  104 Thornberry Rd, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft
  • Built 1973

  104 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 11% Above List Price
  • $543/SF
  • 4 Days On Market

  Last Sold Price $1,425,000

  Last Listing Agent Philip Vita Compass
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  $3,290,000 Open Sat 12PM - 1:30PM

  • 6 Beds
  • 5.5 Baths
  • 7,431 Sq Ft

  27 Everett Ave, Winchester, MA 01890

  This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are

  Nancy Pallotta Gibson Sotheby's International Realty

  27 Everett Ave, Winchester, MA 01890
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  $3,000 total monthly price

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

  200 Swanton St Unit T35, Winchester, MA 01890

  SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of

  Nuri Tirana Tirana Real Estate Group

  200 Swanton St Unit T35, Winchester, MA 01890
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  $3,174,500 Sold Sep 02, 2025

  18 Wickham Rd, Winchester, MA 01890

  • 6 Beds
  • 5 Baths
  • 7,005 Sq Ft
  • Built 2022

  Last Sold Summary

  • 2% Below List Price
  • $453/SF
  • 9 Days On Market

  Current Estimated Value $3,151,657

  Last Listing Agent Philip Vita Compass

  18 Wickham Rd, Winchester, MA 01890
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  Est $1,803,044 Not Listed For Sale

  73 Thornberry Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 3,046 Sq Ft
  • Built 1966

  73 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 9% Above List Price
  • $543/SF
  • 7 Days On Market

  Last Sold Price $1,655,000

  Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group
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  /35

  $2,649,000 Open Sat 12:30PM - 2PM

  • 4 Beds
  • 4.5 Baths
  • 5,614 Sq Ft

  2 Abby Rd, Winchester, MA 01890

  Tucked on a quiet cul-de-sac within an exclusive enclave of homes, this newer residence offers a harmony of refined living and natural beauty. Just moments from the trails and vistas of the Middlesex Fells Reservation, this home is ideally positioned for those who value serenity and effortless access to the outdoors. Thoughtfully designed, it unfolds with an airy, open-concept where a sunlit

  Nancy Pallotta Gibson Sotheby's International Realty

  2 Abby Rd, Winchester, MA 01890
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  $2,596 total monthly price

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  19 Irving St Unit 3-J, Winchester, MA 01890

  Top Floor (3rd floor) 2 Bedroom 1 Bathroom located minutes from Winchester Center & Commuter Rail. Fully carpeted Livingroom, bedrooms hallway ,with kitchen and bathroom ceramic tile. Private deck overlooking yard. gas cooking, gas heat; dishwasher being installed, carpet is being cleaned; washer dryer in unit.Tenant pays gas & electric (and trash at Winchester Transfer Station. Transfer

  19 Irving St Unit 3-J, Winchester, MA 01890
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  $1,260,000 Sold Jun 30, 2025

  261 Cambridge St Unit 261 G, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,705 Sq Ft
  • Built 1885

  Last Sold Summary

  • 3% Below List Price
  • $466/SF
  • 41 Days On Market

  Current Estimated Value $1,337,852

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

  261 Cambridge St Unit 261 G, Winchester, MA 01890
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  Est $1,736,245 Not Listed For Sale

  22 Berkshire Dr, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 3,224 Sq Ft
  • Built 1967

  22 Berkshire Dr, Winchester, MA 01890

  Last Sold Summary

  • 11% Above List Price
  • $486/SF
  • 3 Days On Market

  Last Sold Price $1,568,000

  Last Listing Agent Timothy Morgan RE/MAX
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  $2,965,000 Pending

  • 7 Beds
  • 8 Baths
  • 7,043 Sq Ft

  45 Bacon St, Winchester, MA 01890

  Situated at the corner of Ginn Road neighborhood, this home was custom built by a premier local builder- with its dramatic design, it is a must see! Ideally located near town center w/ easy access to the commuter rail, Mystic lakes trails & beach, Ginn playground & the vibrant town center. This 7000sf, 7 BR home is perfectly designed for todays living w/ au-pair & multi generational options. A

  Kim Covino Compass

  45 Bacon St, Winchester, MA 01890
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  $9,500 total monthly price

  • 6 Beds
  • 4.5 Baths
  • 3,100 Sq Ft
  • House for Rent

  23 Jefferson Rd, Winchester, MA 01890

  Stunning home situated in one of Winchester's most sought-after neighborhoods available for rare 1 or 2 year rental. Enter the elegant foyer to find large living room, sun-drenched playroom and dining room next to generous kitchen which overlooks the large, private back yard. Laundry in side entry mud room offers convenience and a front-facing home office overlooks the picturesque neighborhood.

  Kim Covino Compass

  23 Jefferson Rd, Winchester, MA 01890
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  $1,390,000 Sold Jul 15, 2025

  26 Ridge St, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft
  • Built 1963

  Last Sold Summary

  • 1% Above List Price
  • $582/SF
  • 6 Days On Market

  Current Estimated Value $1,397,590

  Last Listing Agent Dream Team Dreamega International Realty LLC

  26 Ridge St, Winchester, MA 01890
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  Est $2,144,530 Not Listed For Sale

  5 Partridge Ln, Winchester, MA 01890

  • 5 Beds
  • 4 Baths
  • 4,620 Sq Ft
  • Built 1967

  5 Partridge Ln, Winchester, MA 01890

  Last Sold Summary

  • 8% Above List Price
  • $428/SF
  • 6 Days On Market

  Last Sold Price $1,977,000

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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  $2,299,000 Pending

  • 7 Beds
  • 5.5 Baths
  • 4,929 Sq Ft

  89 Wildwood St, Winchester, MA 01890

  Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  89 Wildwood St, Winchester, MA 01890
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  $1,800 - $1,850 total monthly price

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

  219 Washington St, 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- Close to public transportation

  219 Washington St, Winchester, MA 01890
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  /41

  $1,510,000 Sold Sep 02, 2025

  155 Highland Ave, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 1,965 Sq Ft
  • Built 1900

  Last Sold Summary

  • 13% Above List Price
  • $768/SF
  • 8 Days On Market

  Current Estimated Value $1,449,218

  Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

  155 Highland Ave, Winchester, MA 01890
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  Est $2,014,362 Not Listed For Sale

  89 Thornberry Rd, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 4,532 Sq Ft
  • Built 1964

  89 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 12% Above List Price
  • $397/SF
  • 12 Days On Market

  Last Sold Price $1,799,000

  Last Listing Agent Kim Covino Compass
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  $2,299,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,283 Sq Ft

  12 Yale St, Winchester, MA 01890

  Timeless architecture blends beautifully with curated updates designed for modern living in this classic Colonial. Sunlight pours into the newly renovated gourmet kitchen, where beautiful cabinetry, premium appliances, and thoughtful design create an inviting heart of the home for both everyday living and elegant entertaining. A gracious front-to-back living room offers exceptional scale and

  Nancy Pallotta Gibson Sotheby's International Realty

  12 Yale St, Winchester, MA 01890
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  /22

  $8,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 3,500 Sq Ft
  • House for Rent

  31 Fells Rd, Winchester, MA 01890

  Available for short term rental through October 2025 with flexible lease options. Prime location on desirable Fells Road with easy access to Middlesex Fells trails and conservation land. This charming home sits on a beautiful lot and offers a spacious first floor featuring a large family room, updated kitchen, and a den or optional first floor bedroom. Enjoy the screened porch overlooking the

  Kim Covino Compass

  31 Fells Rd, Winchester, MA 01890
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  /39

  $2,050,000 Sold Oct 15, 2025

  64 Westland Ave, Winchester, MA 01890

  • 4 Beds
  • 5 Baths
  • 3,716 Sq Ft
  • Built 1931

  Last Sold Summary

  • $552/SF
  • 2 Days On Market

  Current Estimated Value $2,007,230

  Last Listing Agent The Murphy Group Lexington William Raveis R.E. & Home Services

  64 Westland Ave, Winchester, MA 01890
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  Est $2,089,027 Not Listed For Sale

  3 Berkshire Dr, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 3,344 Sq Ft
  • Built 1967

  3 Berkshire Dr, Winchester, MA 01890

  Last Sold Summary

  • 2% Below List Price
  • $635/SF
  • 4 Days On Market

  Last Sold Price $2,125,000

  Last Listing Agent Allison Shannon Berkshire Hathaway HomeServices Robert Paul Properties
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  $2,150,000 Open Sun 12PM - 1:30PM

  • 6 Beds
  • 5 Baths
  • 3,728 Sq Ft

  6 Ivy Cir, Winchester, MA 01890

  Spacious newly gut renovated colonial set back on a cul-de-sac! Unbeatable location in quiet neighborhood less than a mile from all Winchester's amazing public schools and Wedge Pond. Hardwood floors throughout with gorgeous kitchen featuring huge island, large living and dining rooms. A vaulted family room with authentic barn board detailing sits adjacent to the kitchen, opening to a large

  Rose Hall Blue Ocean Realty, LLC

  6 Ivy Cir, Winchester, MA 01890
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  $3,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  36 Cross St Unit 1, Winchester, MA 01890

  Recently updated and filled with natural light, this bright first-floor unit offers a flexible and spacious layout. The eat-in kitchen features new flooring, abundant cabinet space, a bonus closet/pantry, and an additional adjoining room ready to be customized to fit your needs.The home includes two well-sized bedrooms, high ceilings, and beautiful hardwood floors throughout. The renovated

  Dawn Felicani Gibson Sotheby's International Realty

  36 Cross St Unit 1, Winchester, MA 01890
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  $715,000 Sold Jun 27, 2025

  7 Conant Rd Unit 37, Winchester, MA 01890

  • 2 Beds
  • 2.5 Baths
  • 1,539 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $465/SF
  • 33 Days On Market

  Current Estimated Value $731,251

  Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Conant Rd Unit 37, Winchester, MA 01890
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  Est $1,286,827 Not Listed For Sale

  233 High St, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 2,218 Sq Ft
  • Built 1952

  233 High St, Winchester, MA 01890

  Last Sold Summary

  • 11% Above List Price
  • $523/SF
  • 7 Days On Market

  Last Sold Price $1,161,000

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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  $2,250,000 Open Sat 12PM - 1:30PM

  • 7 Beds
  • 3.5 Baths
  • 3,926 Sq Ft

  10 Edgehill Rd, Winchester, MA 01890

  This exceptional Colonial Revival home in a sought-after Winchester neighborhood blends craftsmanship, thoughtful updates and a design layout perfect for entertaining and modern day living. A welcoming front porch introduces a double entry foyer, high ceilings with crown molding and period detail that flow through the formal dining and living room with fireplace to the family room, kitchen and

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

  10 Edgehill Rd, Winchester, MA 01890
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  $13,000 total monthly price

  • 6 Beds
  • 5.5 Baths
  • 6,400 Sq Ft
  • House for Rent

  52 N Border Rd, Winchester, MA 01890

  Grand and masterfully crafted, this exceptional residence sits on a private road abutting the Fells conservation land, offering rare privacy and natural surroundings. The spacious home features 6 bedrooms and 6 bathrooms, beginning with a stunning foyer that opens to a sprawling first floor. Sun-filled rooms showcase exquisite custom craftsmanship throughout. The gourmet kitchen is equipped with

  Dylan Archambault Archambault Real Estate

  52 N Border Rd, Winchester, MA 01890
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  /19

  $690,000 Sold Jun 06, 2025

  7 Conant Rd Unit 60, Winchester, MA 01890

  • 2 Beds
  • 2.5 Baths
  • 1,634 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Below List Price
  • $422/SF
  • 20 Days On Market

  Current Estimated Value $732,356

  Last Listing Agent Irene Novia Loka Matahari Real Estate LLC

  7 Conant Rd Unit 60, Winchester, MA 01890
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  Est $1,293,489 Not Listed For Sale

  134 Johnson Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,430 Sq Ft
  • Built 1977

  134 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 10% Above List Price
  • $484/SF
  • 3 Days On Market

  Last Sold Price $1,175,000

  Last Listing Agent Steve Savarese Senne

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