Old Bennington, VT Homes

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  /46

  $795,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 3,560 Sq Ft

  1 Monument Ave, Bennington, VT 05201

  This beautifully restored Old Bennington 4-bedroom Colonial, originally built in 1790 by Captain David Robinson, Jr., grandson of the founder of Bennington, seamlessly blends rich history with modern luxury. Located in the heart of the historic district, the home boasts breathtaking views of the Bennington Battle Monument, Mount Anthony, and the surrounding mountains. Meticulously updated, the

  Kelley Mccarthy Mahar McCarthy Real Estate

  1 Monument Ave, Bennington, VT 05201
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  /50

  $530,000 Sold Jan 16, 2025

  • 3,782 Sq Ft
  • $140/SF
  • 86 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1829

  3 Seminary Ln, Bennington, VT 05201

  Coveted Three Seminary Lane | Old Bennington Originally established in 1829 as Mount Anthony Seminary, this remarkable property first served as a boys' boarding school. In 1897, it transitioned to become the clubhouse of the Mount Anthony Country Club, a role it maintained well into the early 20th century. Now situated on 2.5 acres, this charming Colonial-style home exudes character and grace,

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  3 Seminary Ln, Bennington, VT 05201
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  /37

  Est $382,478 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,496 Sq Ft

  115 Monument Ave, Bennington, VT 05201

  115 Monument Ave, Bennington, VT 05201
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  /40

  $1,015,000 Sold Oct 18, 2024

  • 4,995 Sq Ft
  • $203/SF
  • 70 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1983

  13 Monument Cir, Bennington, VT 05201

  Set on 7.16 picturesque acres, graced by the iconic Bennington Battle Monument, this beautifully crafted saltbox colonial offers a blend of historic charm and modern comfort. The spacious, light-filled living room features a cozy wood-burning fireplace and an elegant, coffered ceiling, perfect for relaxed evenings. The country-style kitchen, complete with a dining area, provides stunning mountain

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  13 Monument Cir, Bennington, VT 05201
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  /40

  Est $670,468 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,969 Sq Ft

  43 Monument Ave, Bennington, VT 05201

  43 Monument Ave, Bennington, VT 05201
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  /35

  $575,000 Sold Jun 27, 2024

  • 3,448 Sq Ft
  • $167/SF
  • 136 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1830

  16 Walloomsac Rd, Bennington, VT 05201

  Nestled in the charming Old Bennington, this historic home offers a unique blend of timeless elegance and breathtaking views of the monument. Set on a generous 2-acre lot, this property boasts four bedrooms and four-and-a-half bathrooms, providing ample space for comfortable living. Three fireplaces grace this home, creating a cozy and inviting atmosphere. Imagine the crackling warmth and soft

  Kelley Mccarthy Mahar McCarthy Real Estate

  16 Walloomsac Rd, Bennington, VT 05201
• 

  

  /39

  Est $686,722 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,870 Sq Ft

  195 Walloomsac Rd, Bennington, VT 05201

  195 Walloomsac Rd, Bennington, VT 05201
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  /40

  Est $650,500 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,366 Sq Ft

  110 Monument Ave, Bennington, VT 05201

  110 Monument Ave, Bennington, VT 05201
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  /40

  Est $384,751 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,320 Sq Ft

  2 Church Ln, Bennington, VT 05201

  2 Church Ln, Bennington, VT 05201
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  /40

  Est $678,077 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,638 Sq Ft

  88 Monument Ave, Bennington, VT 05201

  88 Monument Ave, Bennington, VT 05201
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  /40

  Est $770,852 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,968 Sq Ft

  74 Monument Ave, Bennington, VT 05201

  74 Monument Ave, Bennington, VT 05201
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  /40

  Est $474,558 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,814 Sq Ft

  10 West Rd, Bennington, VT 05201

  10 West Rd, Bennington, VT 05201
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  /40

  Est $674,078 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,716 Sq Ft

  57 Monument Ave, Bennington, VT 05201

  57 Monument Ave, Bennington, VT 05201
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  /38

  Est $510,356 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft

  55 Monument Ave, Bennington, VT 05201

  55 Monument Ave, Bennington, VT 05201
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  /40

  Est $435,640 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,586 Sq Ft

  12 West Rd, Bennington, VT 05201

  12 West Rd, Bennington, VT 05201
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  /40

  Est $1,052,440 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 5,056 Sq Ft

  11 West Rd, Bennington, VT 05201

  11 West Rd, Bennington, VT 05201
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  /40

  Est $598,678 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,516 Sq Ft

  32 Bank St, Bennington, VT 05201

  32 Bank St, Bennington, VT 05201
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  /28

  Est $444,693 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,120 Sq Ft

  31 Bank St, Bennington, VT 05201

  31 Bank St, Bennington, VT 05201
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  /40

  Est $434,940 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,304 Sq Ft

  41 Bank St, Bennington, VT 05201

  41 Bank St, Bennington, VT 05201
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  /40

  Est $518,835 Not Listed For Sale

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

  34 Monument Ave, Bennington, VT 05201

  34 Monument Ave, Bennington, VT 05201
• 

  

  /29

  Est $676,181 Not Listed For Sale

  • 3 Beds
  • 4.5 Baths
  • 3,555 Sq Ft

  33 Monument Ave, Bennington, VT 05201

  33 Monument Ave, Bennington, VT 05201
• 

  

  /39

  Est $708,827 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,541 Sq Ft

  11 Monument Ave, Bennington, VT 05201

  11 Monument Ave, Bennington, VT 05201
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  /36

  Est $604,019 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,594 Sq Ft

  7 Fairview St, Bennington, VT 05201

  7 Fairview St, Bennington, VT 05201
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  /40

  Est $403,965 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,433 Sq Ft

  364 Elm St, Bennington, VT 05201

  364 Elm St, Bennington, VT 05201
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  /2

  Est $495,508 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  85 Monument Ave Unit 87, Bennington, VT 05201

  85 Monument Ave Unit 87, Bennington, VT 05201
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  /40

  Est $475,546 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,706 Sq Ft

  81 Monument Ave, Bennington, VT 05201

  81 Monument Ave, Bennington, VT 05201
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  /35

  Est $1,206,566 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 7,522 Sq Ft

  7 Monument Cir, Bennington, VT 05201

  7 Monument Cir, Bennington, VT 05201
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  /35

  Est $602,324 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,442 Sq Ft

  46 Bank St, Bennington, VT 05201

  46 Bank St, Bennington, VT 05201
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  /39

  Est $699,273 Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 4,772 Sq Ft

  40 Monument Ave, Bennington, VT 05201

  40 Monument Ave, Bennington, VT 05201
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  /34

  Est $419,945 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  38 Monument Ave, Bennington, VT 05201

  38 Monument Ave, Bennington, VT 05201
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  /27

  Est $569,017 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,480 Sq Ft

  9 Monument Cir, Bennington, VT 05201

  9 Monument Cir, Bennington, VT 05201
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  /3

  Not Listed For Sale

  00 Fairview St, Bennington, VT 05201

  00 Fairview St, Bennington, VT 05201
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  /15

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  50 Catamount Ln, Bennington, VT 05201

  50 Catamount Ln, Bennington, VT 05201
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  /25

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft

  30 Catamount Ln, Bennington, VT 05201

  30 Catamount Ln, Bennington, VT 05201
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  /2

  Est $677,139 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,284 Sq Ft

  11 Catamount Ln, Bennington, VT 05201

  11 Catamount Ln, Bennington, VT 05201
• 

  /2

  Not Listed For Sale

  0 West Rd, Bennington, VT 05201

  0 West Rd, Bennington, VT 05201
• 

  /2

  Est $378,000 Not Listed For Sale

  • Studio
  • 17,722 Sq Ft

  67 Monument Ave, Bennington, VT 05201

  67 Monument Ave, Bennington, VT 05201
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  /2

  Est $267,205 Not Listed For Sale

  • 1,152 Sq Ft

  1 College Dr, Bennington, VT 05201

  1 College Dr, Bennington, VT 05201
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  /2

  Est $375,880 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,872 Sq Ft

  107 Monument Ave, Bennington, VT 05201

  107 Monument Ave, Bennington, VT 05201
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  /2

  Est $500,603 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,554 Sq Ft

  120 Monument Ave, Bennington, VT 05201

  120 Monument Ave, Bennington, VT 05201

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