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

165 Pippin Knoll
Bennington, VT 05201

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

$351,000

Last Sold: Nov 21, 2025
8% over list $325K
$117/sqft

$351,000

Last Sold: Nov 21, 2025
8% over list $325K
$117/sqft
4 Beds
3 Baths
2,994 sqft
(on 4.12 acres)

Homes for sale near 165 Pippin Knoll

Skip to last item
Skip to first item

Apartments for Rent

Skip to last item
Skip to first item

Local Information

Map showing home location
© Google
-- mins to
Commute Destination
Last check for updates: about 3 hours ago
Listed by Kelley M McCarthy
Mahar McCarthy Real Estate, (802) 442-8337
Bought with: Lillian West, Maple Leaf Real Estate, (802) 447-3210
Source: PrimeMLS, MLS#5062264

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from November 21, 2025

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating only
HOA
None
Price/Sqft
$117/sqft
Listed
180+ days ago

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 History for 165 Pippin Knoll

DatePriceEventSource
11/21/2025$351,000Sold
PrimeMLS #5062264
09/19/2025$325,000Listed For SalePrimeMLS #5062264
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax
Assessment$245,200
Home facts updated by county records

Comparable Sales for 165 Pippin Knoll

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
126 Fox Hill Road, Bennington, VT
0.83
Single-Family Home
$600,000
11/12/25
5
1.5
2,450
17 Jennings Drive, Bennington, VT
0.52
Single-Family Home
$162,900
07/18/25
3
2
1,800
169 Bard Road, Bennington, VT
1.03
Single-Family Home
$316,000
08/07/25
3
2
1,584
77 Monument Avenue, Old Bennington, VT
1.08
Single-Family Home
$740,000
10/10/25
4
3.5
4,032
1 Monument Avenue, Old Bennington, VT
0.84
Single-Family Home
$800,000
05/21/25
4
2
3,560
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

Assigned Schools

These are the assigned schools for 165 Pippin Knoll.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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 2026-05-09 17:46:37 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.

Homes for rent near 165 Pippin Knoll

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 165 Pippin Knoll

Skip to last item
Skip to first item

Explore by feature

165 Pippin Knoll, Bennington, VT 05201 is a 4 bedroom, 3 bathroom, 2,994 sqft single-family home built in 1958. This property is not currently available for sale. 165 Pippin Knoll was last sold on Nov 21, 2025 for $351,000 (8% higher than the asking price of $325,000). The current Trulia Estimate for 165 Pippin Knoll is $358,400.