165 Pippin Knoll, Bennington, VT 05201
Property image
Property image
SOLD
NOV 21, 2025
Listed by Kelley M McCarthy, Mahar McCarthy Real Estate, (802) 442-8337 . Bought with Maple Leaf Real Estate

$373,200

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,994 sqft (on 4.12 acres)

165 Pippin Knoll, Bennington, VT 05201

Refinance Your Home
Currently Off Market - Sold Nov 21, 2025 for $351,000 (8% above list price)

Home Value

Trulia Estimate
$373K
Since last month
Increased$7K (+1.9%)
Since last year
Increased$25K (+7.1%)
Since last sale
Increased$22K (+6.3%)
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 +70% in the last 10 years
MonthEstimated value
2026
August 2026$373K
August 2026$373K
July 2026$366K
June 2026$370K
May 2026$361K
April 2026$356K
March 2026$357K
February 2026$352K
January 2026$352K
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
495 Fairview Street, Bennington, VT
0.34
Single-Family Home
$400,000
09/22/25
3
2
1,309
166 Cardinal Lane, Bennington, VT
0.79
Single-Family Home
$295,000
07/22/26
3
2
2,753
58 Mount Anthony Road, Bennington, VT
0.92
Single-Family Home
$505,000
08/21/26
3
2.5
2,715
126 Fox Hill Road, Bennington, VT
0.83
Single-Family Home
$600,000
11/12/25
5
1.5
2,450
34 Monument Avenue, Bennington, VT
0.97
Single-Family Home
$625,000
08/31/26
4
2.5
2,692
695 Dermody Road, Bennington, VT
0.91
Single-Family Home
$355,000
05/29/26
3
1.5
1,748
77 Monument Avenue, Old Bennington, VT
1.08
Single-Family Home
$740,000
10/10/25
4
3.5
4,032
458 Fox Hill Road, Bennington, VT
1.15
Single-Family Home
$435,000
10/10/25
4
3
3,040
55 Monument Avenue, Old Bennington, VT
1.00
Single-Family Home
$640,000
12/22/25
3
2.5
2,675

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 Walloomsac Road, Bennington, VT 05201
0.27
-
-
-
-
Off Market
495 Fairview Street, Bennington, VT 05201
0.34
$429,400
3
2
1,309
Off Market
390 Fairview Street, Bennington, VT 05201
0.39
-
-
-
-
Off Market
109 Village Lane, Bennington, VT 05201
0.40
$513,100
4
2.5
2,632
Off Market
85 Silk Road, Bennington, VT 05201
0.44
$270,100
2
1
1,053
Off Market
17 Jennings Drive, Bennington, VT 05201
0.52
$176,700
3
2
1,800
Off Market
1427 Walloomsac Road, Bennington, VT 05201
0.57
$268,400
2
1.5
1,890
Off Market
1086 West Road, Bennington, VT 05201
0.66
$1,800,000
9
6
6,956
Recently Sold
16 Walloomsac Road, Old Bennington, VT 05201
0.73
$624,300
4
4.5
3,448
Off Market
13 Monument Circle, Old Bennington, VT 05201
0.77
$1,034,000
5
4
4,995
Off Market
166 Cardinal Lane, Bennington, VT 05201
0.79
$295,000
3
2
2,753
Recently Sold

Local Information

  • Map ViewExplore the area around 165 Pippin Knoll.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1958
4.12 acre lot
2,994 sqft
$117/sqft
Garage

About this House

Set well back from the road, this mid-century modern home emphasizes simple lines, an indoor-outdoor connection, and panoramic views. The main level centers on an open living/dining/kitchen area anchored by a fireplace and oversized windows that overlook the pond and rolling landscape beyond. The primary suite on this level provides private comfort. A second-floor bedroom offers a rare upper-level retreat complete with a private bath - perfect for guests, teenagers, or a dedicated workspace. Though the home’s layout and setting are outstanding, it needs thoughtful updating: kitchens and baths could be refreshed, finishes modernized, and mechanicals upgraded to improve energy efficiency. With cosmetic work and systems improvements, this property will be transformed into a stylish, comfortable showpiece that honors its mid-century heritage. This property delivers the best of both worlds - architectural interest and a peaceful natural setting. The pond and views create an immediate sense of escape, while the four-bedroom layout and three baths make it practical for full-time living or a vacation retreat. For buyers who appreciate mid-century lines and want to add modern amenities, this is an inspired canvas.
165 Pippin Knoll, Bennington, VT 05201 is a 4 bedroom, 3 bathroom, 2,994 sqft single-family home built in 1958. It last sold for $351,000 on Nov 21, 2025 (8% above the $325,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $373,200, with a rent estimate of $3,955/month.

Home Details for 165 Pippin Knoll

Active Status

MLS Status: Closed

Interior Features

Interior Details
Number of Rooms: 8
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 2
Dimensions and Layout
Living Area: 2994 Square Feet
Appliances & Utilities
Utilities: Cable Available, Underground Oil Tank, Fiber Optic Internt AvailAppliances: Dryer, Electric Range, Refrigerator, WasherDryerLaundry: 1st Floor LaundryRefrigeratorWasher
Heating & Cooling
Heating: Oil,Baseboard,Electric,Wood StoveNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Fireplace & Spa
Number of Fireplaces: 1Fireplace: 1 Fireplace, Wood Stove Hook-upHas a Fireplace
Gas & Electric
Electric: 100 Amp Service, Circuit Breakers
Windows, Doors, Floors & Walls
Flooring: Carpet, Laminate
Levels, Entrance, & Accessibility
Stories: 2Levels: Two, Walkout Lower LevelFloors: Carpet, Laminate
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PatioExterior: Balcony, Deck, Garden, Natural ShadeFoundation: Concrete SlabGarden
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageParking Spaces: 2Parking: Crushed Stone,Detached
Frontage
Waterfront: PondRoad Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved
Water & Sewer
Sewer: Septic Tank
Farm & Range
Frontage Length: Road frontage: 300
Finished Area
Finished Area (above surface): 2994 Square Feet

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Split EntryArchitecture: Contemporary
Building
Construction Materials: Vertical Siding, Wood SidingNot a New Construction

Price & Status

Price
List Price: $325,000Price Per Sqft: $117/sqft

Location

Direction & Address
City: Bennington
School Information
Elementary School: Monument Elementary SchoolElementary 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

Building

Building Area
Building Area: 2994 Square Feet

Lot Information

Lot Area: 4.12 Acres

Miscellaneous

Mls Number: 5062264Water View: WaterAbove Grade Unfinished Area: 2994Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Source: AssessorBelow Grade Unfinished Area Units: Square Feet

Price and Tax history

DateEventPrice
Nov 21, 2025
Source: PrimeMLS #5062264
Sold
$351,000
Sep 19, 2025
Source: PrimeMLS #5062264
Listed For Sale
$325,000

Market trends in Bennington

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
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.
  • Jowasieleuski
    "I have lived here 20 years and it has gone down hill in this time. No real growth here. Drug use is rampant and jobs are few and far."
    3
    Flag
  • Thomayera
    "Nothing special about Bennington it may be pretty some times but that’s about it. When it’s pretty we have too many tourists so no win"
    1
    Flag
  • Thomayera
    "Lived on this part of Gage street for 10 years now. It’s been pretty decent. Had some theft once but other than that was okay"
    1
    Flag
  • Kjae_pristine
    "I lived in Bennington over 20 years. Bennington has a different type of living. One minute you are in the center of town the next minute you are in the country with nothing but mountains to look at"
    0
    Flag
  • Bryonbleau0217
    "Minimal traffic,I travel less then 5 miles to work most business are within walking distance.all town roads and no highways are needed if you work and live in Bennington"
    0
    Flag
  • s. lowers
    "There are other dogs around, all over. So when one barks, they all do. They’re friendly most of the time though, but I guess your dog would pull when walking? I don’t know. I’m sure everything will be great! "
    0
    Flag
  • Shennajeann
    "Not many people travel up and down the road, and the neighbors are very nice. My neighbors inform me if anybody is on my property or anything "
    0
    Flag
  • Tiggacrandall79276
    "the Neighborhood is clean and there is no drug activity here it's quite next to the Jr high school. and watch them play baseball or football"
    1
    Flag
  • Starlene G.
    "people genuinely stay to them self's ,very quiet ,always seem to be rushing around though ,and they stay busy!😊 very clean and nice place to live ,every thing is pretty much accessible!"
    0
    Flag
  • renbisson
    "I was born here. I have lived in CA, and visited several areas of the country. I came here to raise my kids."
    0
    Flag
  • mymusic54
    "Live here - very quiet, close to App hiking trail, new Highway, still super quiet and convenient travel in all directions. Although in town, beautiful countryside within miles."
    0
    Flag

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 2026-09-11 00:44:16 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.

Frequently asked questions about 165 Pippin Knoll

  • What is 165 Pippin Knoll estimated to be worth?
    Trulia's estimated value for 165 Pippin Knoll in Bennington, VT is $373,200.
  • What is the price history for 165 Pippin Knoll?
    165 Pippin Knoll in Bennington, VT last sold for $351,000 in November 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 165 Pippin Knoll have laundry facilities?
    Yes, 165 Pippin Knoll in Bennington, VT has in-unit laundry.
  • How big is the lot at 165 Pippin Knoll?
    The lot at 165 Pippin Knoll in Bennington, VT is about 4.1 acres.

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