Winchester MA FSBO Homes (136)

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We have 136 homes for sale by owner in Winchester, MA. The median list price in Winchester, MA is $1,059,956 and the average price per square foot is $339,671.

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Homes For Sale

$1,949,000

  • 5 Bed
  • 4 Bath
  • 4,744 Sqft
  • 0.22 Acre(Lot)
14 Grove Street, Winchester, MA

Located just outside the town center near brooks neighborhood & the train to boston! this spacious home has it... Read More

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Condo For Sale

$1,499,000

  • 4 Bed
  • 4 Bath
  • 4,214 Sqft
7 Wainwright Rd #117, Winchester, MA

Welcome to the largest unit at the ledges! this stunning f unit boasts soaring ceilings and an expansive open... Read More

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Homes For Sale

$2,499,000

  • 6 Bed
  • 4 Bath
  • 4,212 Sqft
  • 0.26 Acre(Lot)
19 Yale St, Winchester, MA

Welcome home to 19 yale, where elegance and charm embrace, located in the top neighborhood that everyone wants!... Read More

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Homes For Sale

$1,199,000

  • 4 Bed
  • 2 Bath
  • 2,759 Sqft
  • 0.13 Acre(Lot)
80 Harvard Street, Winchester, MA

Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. the open floor plan... Read More

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Homes For Sale

$2,450,000

  • 5 Bed
  • 5 Bath
  • 3,940 Sqft
  • 0.59 Acre(Lot)
17 Wagon Wheel Rd, Winchester, MA

Enjoy breathtaking boston skyline views from nearly every room of this meticulously maintained home, offering... Read More

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Homes For Sale

$998,000

  • 4 Bed
  • 3 Bath
  • 2,333 Sqft
  • 0.21 Acre(Lot)
48 Tremont Street, Winchester, MA

Welcome to this well loved 4-bedroom expanded cape, on quiet cul-de-sac, cared for by the original owners for... Read More

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Homes For Sale

$2,199,000

  • 6 Bed
  • 4 Bath
  • 4,696 Sqft
  • 0.41 Acre(Lot)
5 Squire Rd, Winchester, MA

Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. sunlight pours into the... Read More

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Homes For Sale

$1,499,000

  • 3 Bed
  • 2 Bath
  • 1,520 Sqft
  • 0.17 Acre(Lot)
10 Allen Rd, Winchester, MA

Located in a very desirable east hill neighborhood, this one owner circa 1929 dutch colonial offers a wonderful... Read More

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Homes For Sale

$3,599,000

  • 6 Bed
  • 6 Bath
  • 7,431 Sqft
  • 0.64 Acre(Lot)
27 Everett Ave, Winchester, MA

Completely renovated in 2023/2024! this is one of the most distinguished homes on everett avenue, with... Read More

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Homes For Sale

$1,149,000

  • 3 Bed
  • 2 Bath
  • 1,646 Sqft
  • 0.17 Acre(Lot)
7 Indian Hill Road, Winchester, MA

This inviting ranch house is cheerful and functional. sunlight floods the open living and dining rooms, while... Read More

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Homes For Sale

$2,050,000

  • 4 Bed
  • 4 Bath
  • 3,274 Sqft
  • 0.35 Acre(Lot)
57 Jefferson Rd, Winchester, MA

Situated on a picturesque corner lot, this exceptional home is nestled in a very desirable neighborhood! step... Read More

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Homes For Sale

$2,449,000

  • 4 Bed
  • 4 Bath
  • 4,959 Sqft
  • 0.59 Acre(Lot)
5 Azalea Rd, Winchester, MA

Exceptional custom contemporary home nestled on a cul-de-sac in sought after west side neighborhood! open floor... Read More

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Homes For Sale

$3,799,900

  • 7 Bed
  • 8 Bath
  • 7,429 Sqft
  • 0.57 Acre(Lot)
11 Viking Rd, Winchester, MA

Prepare to be captivated by the elegance of 11 viking rd. this magnificent home, boasting over 7,000 square feet... Read More

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Homes For Sale

$1,295,000

  • 4 Bed
  • 2 Bath
  • 2,202 Sqft
  • 0.16 Acre(Lot)
71 Woodside Rd, Winchester, MA

Nestled in the heart of winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square... Read More

Pending
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Homes For Sale

$925,000

  • 4 Bed
  • 2 Bath
  • 2,172 Sqft
  • 0.3 Acre(Lot)
322 Cambridge St, Winchester, MA

Not your average garrison colonial! you might not expect the bright, open charm waiting within this inviting... Read More

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Homes For Sale

$2,499,000

  • 6 Bed
  • 4 Bath
  • 4,667 Sqft
  • 0.26 Acre(Lot)
9 Prospect St, Winchester, MA

Step into a piece of history with this incredibly charming 1895 colonial revival, a home that exudes elegance,... Read More

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Homes For Sale

$1,250,000

  • 4 Bed
  • 2 Bath
  • 2,621 Sqft
  • 0.25 Acre(Lot)
61 Westland Avenue, Winchester, MA

Welcome to this oversized cape in a lovely west side neighborhood of winchester. opportunity for a little tlc... Read More

Active Under Contract
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Homes For Sale

$2,850,000

  • 5 Bed
  • 5 Bath
  • 5,044 Sqft
  • 0.23 Acre(Lot)
22 Standish Lane, Winchester, MA

This distinguished residence, built by premier local developer, represents the pinnacle of elegant living!... Read More

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Active Under Contract
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Homes For Sale

$1,324,000

  • 3 Bed
  • 4 Bath
  • 2,792 Sqft
  • 0.27 Acre(Lot)
24 Eugene Drive, Winchester, MA

Welcome home to this architect designed 3 plus bedroom, four bath custom cape! spacious rooms within a... Read More

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Homes For Sale

$1,549,000

  • 3 Bed
  • 4 Bath
  • 3,351 Sqft
  • 0.34 Acre(Lot)
34 Fells Road, Winchester, MA

Nestled on a peaceful street surrounded by trees, this beautifully updated cape home offers a perfect blend of... Read More