Listed by Lindsey Martin, Maple Leaf Real Estate, (802) 447-3210 . Bought with Four Corner Properties LLC
$205,400
- 3 Beds
- 1 Bath
- 1,416 sqft (on 0.45 acres)
100 Webb Street, Bennington, VT 05201
Est. Refi. Payment $1,468/mo*
Refinance Your HomeCurrently Off Market - Sold Sep 16, 2025 for $190,000
Home Value
Trulia Estimate
$205KSince last month
Increased$2K (+1%)Since last year
Increased$16K (+8.4%)Since last sale
Increased$16K (+8.5%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +125% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $206K |
| August 2026 | $204K |
| July 2026 | $199K |
| June 2026 | $200K |
| May 2026 | $197K |
| April 2026 | $194K |
| March 2026 | $194K |
| February 2026 | $190K |
| January 2026 | $190K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.14 | Single-Family Home | $241,000 | 09/25/25 | 3 | 1 | 1,070 | |
0.33 | Single-Family Home | $215,000 | 08/27/26 | 3 | 1 | 1,047 | |
0.35 | Single-Family Home | $260,000 | 04/28/26 | 3 | 1.5 | 1,570 | |
0.25 | Single-Family Home | $206,000 | 02/20/26 | 3 | 2 | 1,680 | |
0.15 | Single-Family Home | $130,000 | 01/28/26 | 3 | 1.5 | 1,485 | |
0.45 | Single-Family Home | $77,000 | 08/04/26 | 3 | 1 | 1,508 | |
0.19 | Single-Family Home | $296,500 | 11/21/25 | 3 | 2 | 1,896 | |
0.38 | Single-Family Home | $168,000 | 07/17/26 | 3 | 1 | 1,232 | |
0.31 | Single-Family Home | $225,000 | 02/18/26 | 4 | 2 | 1,702 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.10 | $700,000 | 10 | 9 | 8,300 | Recently Sold | |
0.11 | $226,900 | 3 | 1 | 1,680 | Off Market | |
0.10 | $248,200 | 4 | 1 | 1,620 | Off Market | |
0.12 | $176,300 | 3 | 1.5 | 1,709 | Off Market | |
0.12 | $250,800 | 6 | 3 | 2,240 | Off Market | |
0.12 | $236,300 | 3 | 2 | 1,271 | Off Market | |
0.07 | $275,000 | 4 | 2 | 2,022 | For Sale | |
0.09 | $401,400 | 12 | 4 | 5,400 | Off Market | |
0.08 | $325,700 | 7 | 4 | 4,264 | Off Market | |
0.09 | $269,000 | 4 | 2 | 2,206 | For Sale | |
0.16 | $237,200 | 3 | 2 | 1,416 | Off Market |
Local Information
-- mins to
Home Highlights
Single-Family Home
Built in 1943
0.45 acre lot
1,416 sqft
$145/sqft
Garage
About this House
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.
100 Webb Street, Bennington, VT 05201 is a 3 bedroom, 1 bathroom, 1,416 sqft single-family home built in 1943. It last sold for $190,000 on Sep 16, 2025 (5% below the $200,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $205,400, with a rent estimate of $2,275/month.
Home Details for 100 Webb Street
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MLS Status: Closed |
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Interior Details Basement: Concrete,Interior Stairs,Interior EntryNumber of Rooms: 6 |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1 |
Dimensions and Layout Living Area: 1416 Square Feet |
Appliances & Utilities Utilities: Cable Available, Phone AvailableAppliances: Dryer, Freezer, Electric Range, Refrigerator, WasherDryerLaundry: In BasementRefrigeratorWasher |
Heating & Cooling Heating: Oil,Hot AirNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil |
Fireplace & Spa Number of Fireplaces: 1Fireplace: 1 FireplaceHas a Fireplace |
Gas & Electric Electric: 100 Amp Service, Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Carpet, Laminate |
Levels, Entrance, & Accessibility Stories: 1.5Levels: One and One HalfFloors: Carpet, Laminate |
View No View |
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Exterior Home Features Roof: Architectural ShinglePatio / Porch: Covered PorchExterior: Garden, Natural Shade, StorageFoundation: ConcreteGarden |
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1Has a GarageParking Spaces: 1Parking: Garage |
Frontage Road Frontage: Public |
Water & Sewer Sewer: Public Sewer |
Farm & Range Frontage Length: Road frontage: 248 |
Finished Area Finished Area (above surface): 1416 Square Feet |
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Year Built Year Built: 1943 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Historic Vintage,New Englander |
Building Construction Materials: Wood Frame, Wood SidingNot a New Construction |
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Price List Price: $200,000 |
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Direction & Address City: Bennington |
School Information Elementary School District: Southwest VermontJr High / Middle School: Mt. Anthony Union Middle SchJr High / Middle School District: Southwest VermontHigh School: Mt. Anthony Sr. UHSD 14High School District: Southwest Vermont |
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Building Area Building Area: 2286 Square Feet |
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Lot Area: 0.45 acres |
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BasementMls Number: 5042437Above Grade Unfinished Area: 1416Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 870Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Sep 16, 2025 Source: PrimeMLS #5042437 | Sold | $190,000 |
Aug 6, 2025 Source: PrimeMLS #5042437 | Contingent | $200,000 |
Jul 16, 2025 Source: PrimeMLS #5042437 | PriceChange | $200,000 Price decreased by 7% |
Jun 30, 2025 Source: PrimeMLS #5042437 | PendingToActive | $215,000 |
Jun 13, 2025 Source: PrimeMLS #5042437 | Contingent | $215,000 |
May 22, 2025 Source: PrimeMLS #5042437 | Listed For Sale | $215,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $2,468 | $84,900 |
Home facts updated by county records
Market trends in Bennington
Last updated August 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
36
Around this home
What Locals Say about Bennington
At least 58 Trulia users voted on each feature.
92 % Say it's dog friendly
82 % Say car is needed
79 % Say yards are well-kept
78 % Say parking is easy
71 % Say there are sidewalks
69 % Say there's holiday spirit
66 % Say there's wildlife
63 % Say it's walkable to restaurants
62 % Say kids play outside
59 % Say people would walk alone at night
56 % Say neighbors are friendly
48 % Say streets are well-lit
44 % Say it's quiet
38 % Say they plan to stay for at least 5 years
33 % Say there are community events
28 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections

Copyright 2026 PrimeMLS, Inc. All rights reserved.
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-09-20 23:08:23 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.
Frequently asked questions about 100 Webb Street
- What is 100 Webb Street estimated to be worth?Trulia's estimated value for 100 Webb Street in Bennington, VT is $205,400.
- What is the price history for 100 Webb Street?100 Webb Street in Bennington, VT last sold for $190,000 in September 2025.
- Is Bennington a buyer's or seller's market?Bennington is currently a buyer's market, based on recent for-sale activity.
- What do residents say about Bennington?Residents describe Bennington, VT as dog-friendly, well-kept, and easy to park in. Most residents say you need a car. See recently sold homes in Bennington, VT.
- Does 100 Webb Street have laundry facilities?Yes, 100 Webb Street in Bennington, VT has in-unit laundry.
- How big is the lot at 100 Webb Street?The lot at 100 Webb Street in Bennington, VT is about 0.45 acres (19,602 sq ft).

