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$190,000

  • Sold
  • Closed
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1,416 Sq. Ft.
  • 0.45 Acres
  • 1 Car Garage
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Enchanted Historic Home with Storybook Charm - A Hidden Gem Near Downtown! Step into a fairytale in this one-of-a-kind, lovingly maintained home - a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort. From the moment you arrive, you're greeted by the cobblestone driveway leading to the wraparound porch with pillars adorned with regal lion heads, perfect for tea, tales, and twilight daydreams. Inside you'll find Dragons carved into the stair railings, an open living room, formal dining room, and a sunny breakfast nook tucked in the heart of the kitchen. The fireplace glows with Bennington pottery tiles around the hearth, and a vintage tub pours water from a sculpted fish faucet, offering a splash of whimsy. Discover a rare delight below: a basement projector booth and private children's puppet theater waiting to be finished. Fantasy meets function in this home Whether you're sipping espresso in the garden or hosting dinner parties in the grand dining room, this home feels like a European escape - without ever leaving town.

Full Property Details for 100 Webb St

General

  • Sold For: $190,000
  • Status: Closed
  • Type: Single Family
  • Source: PrimeMLS
  • MLS ID: 5042437
  • Added to Site: 310 day(s) ago

Interior

  • Number of Rooms: 6
  • Interior Features: Dining Area, 1 Fireplace, Basement Laundry
  • Fireplace: Yes
  • Appliances: Dryer, Freezer, Electric Range, Refrigerator, Washer
  • Flooring: Carpet, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 1
  • Full Bathrooms: 1
  • Bathroom 1: Bathroom Full, Level 1

Bedrooms

  • Total Bedrooms: 3
  • Bedroom 1: Level 2
  • Bedroom 2: Level 2
  • Bedroom 3: Level 2

Other Rooms

  • Living Room: Level 1
  • Dining Room: Dining Room, Level 1

Exterior

  • Exterior Features: Garden Space, Natural Shade, Covered Porch, Storage
  • Color: Brown

Parking

  • Garage: Yes
  • Garage Spaces: 1

Location

  • County: Bennington
  • Driving Directions: From Downtown Bennington drive east on Main St. Take a right onto Beech St. In 0.2 miles turn left onto Rollin St. Then Right onto Webb. The house will be on the right.

School Information

  • School District: Southwest Vermont
  • Middle School: Mt. Anthony Union Middle Sch
  • High School: Mt. Anthony Sr. UHSD 14

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Oil, Hot Air

Utilities

  • Sewer: Public

Structural Information

  • Construction Status: Existing
  • Basement Entrance: Interior
  • Basement Desc.: Concrete, Interior Stairs
  • Roof: Architectural Shingle
  • Stories/Levels: 1.5
  • Square Feet: 1,416
  • Finished Total: 1,416 Sq. Ft.
  • Finished Above Grnd: 1,416 Sq. Ft.
  • Year Built: 1943

Lot Features

  • Lot Size (Acres): 0.45
  • Lot Size (Sq. Ft.): 19,602
  • Frontage: Yes Road Frontage
  • Frontage Feet: 248
  • Driveway/Sidewalk: Other
  • Zoning: VR

Financial Considerations

  • Price Per Sq. Ft.: $141.24

Disclosures and Reports

  • APN: 051-015-67918

Listed by Maple Leaf Realty, Lindsey Martin
Sold by Four Corner Properties LLC, Patrick J. Sady

Listed by Maple Leaf Realty, Lindsey Martin
Sold by Four Corner Properties LLC, Patrick J. Sady

Listing agent

— 100 Webb St —

  • Lindsey Martin

    Maple Leaf Realty

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Price & Sales History for 100 Webb St

Date
Details
Price
Change
Source
9/16/2025
Sold
$190,000
-5%
MLS
7/16/2025
Price Reduced
$200,000
-6.98%
MLS
5/22/2025
Listed
$215,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Maple Leaf Realty, Lindsey Martin
Sold by Four Corner Properties LLC, Patrick J. Sady

100 Webb Street, Bennington, VT 05201 (MLS# 5042437) is a Single Family property that was sold at $190,000 on September 16, 2025. Want to learn more about 100 Webb Street? Do you have questions about finding other Single Family real estate for sale in Bennington? You can browse all Bennington real estate or contact a Coldwell Banker agent to request more information.