374 Winhall Hollow Rd

Winhall, VT 05340

$500,000
Last Sold Price
4
Beds
1,920 Sq. Ft.
$260 / Sq. Ft.
1,920
Sq. Ft.
$260
per Sq. Ft.
Closed 11/26/25
Closed 11/26/25

Description

Tucked away on 9.5 private acres that border the scenic Gale Meadows Pond, this Vermont retreat offers the perfect mix of nature, comfort, and functionality. Whether you're seeking a year-round residence or a seasonal getaway, this property is move-in ready with thoughtful renovations and room to explore. Step inside to a warm and inviting atmosphere where you’ll find brand-new kitchen appliances, a new washer and dryer, new carpet on the main level, and updates in bathrooms with new toilets, sinks,...Tucked away on 9.5 private acres that border the scenic Gale Meadows Pond, this Vermont retreat offers the perfect mix of nature, comfort, and functionality. Whether you're seeking a year-round residence or a seasonal getaway, this property is move-in ready with thoughtful renovations and room to explore. Step inside to a warm and inviting atmosphere where you’ll find brand-new kitchen appliances, a new washer and dryer, new carpet on the main level, and updates in bathrooms with new toilets, sinks, and fixtures. The living room centers around a cozy fireplace—perfect for cold winter nights—while the finished lower level features a built-in bar, ideal for relaxing or entertaining after a day on the slopes or trails. Behind the scenes, the home has been upgraded with a new septic system, new well pump, and new water heater, ensuring efficiency and peace of mind for years to come. Outside, enjoy the peaceful setting from the enclosed, covered deck, surrounded by stone walls, a small frog pond, and beautifully maintained grounds. A two-car detached garage and separate two-bay machine barn provide ample space for snowmobiles, tractors, or other equipment. With a mix of open fields and forest, the property invites outdoor adventure, take a walk through the woods to cast a line in Gale Meadows Pond or simply enjoy the changing seasons in your own backyard sanctuary. This is a one-of-a-kind property! Showings begin at open house 8/31 from 11am-1pm.
  1. Listed by Annette Gallo • Real Broker LLC
  2. Listed by Stephanie Sugden • Real Broker LLC

Sold By EXP Realty

Property Details for 374 Winhall Hollow Road

Zoning
Residential
LISTING UPDATED: 11/26/2025 08:49 PM

Property Details for 374 Winhall Hollow Road

StatusClosed
MLS #5058796
Days on Market4
Taxes$6,381 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1986
Lot Size9.50 AC / 413,820 SF
CountyBennington County

Location

Add your commute

Building Information for 374 Winhall Hollow Road

Stories2Year Built1986Building Size-Lot Size9.50 AC / 413,820 SF

Payment Calculator

$3,002 per month

30 year fixed, 6.28% Interest

Principal and Interest

$2,471

Property Taxes

$532

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 374 Winhall Hollow Road

Summary
Location and General Information
  • City: Winhall
  • County: VT-Bennington
  • Directions: From Bondville take a right on Winhall Hollow Rd. Just past French Hollow Rd. house is first house on the right. From Manchester coming up Route 30, take a left onto Old Town Road to a slight left onto Winhall Hollow take a left. House is first house on the right.
  • Latitude: 43.179279000001003
  • Longitude: -72.882154999999997
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05340
Taxes and HOA Information
  • SPAN Number: 771-245-10101
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Gravel
Property
Lot Information
  • Lot Features: Hilly, Lake Access, Pond, Trail/Near Trail, Wooded
  • Lot Size Acres: 9.5
  • Road Frontage Length: 1100.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Yes
  • Year Built: 1986
Utilities
  • Electric: 220 Volt
  • Sewer: Septic
  • Water Source: Drilled Well, Private
  • Utilities: Cable Available, Propane, Satellite, Telephone Available
  • Internet: Fiber Optic Internet
Interior and Exterior Features
Exterior Features
  • Construction Materials: Vinyl Siding
  • Roof: Metal
Interior Features
  • Appliances: Dryer, Range Hood, Microwave, Refrigerator, Washer
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Finished, Interior Stairs, Walkout
  • Heating: Propane, Oil, Wood, Electric, Hot Water
  • Cooling: None
  • Total Stories: 2

Property History for 374 Winhall Hollow Road

DateEvent & SourcePriceAppreciation
Nov 26, 2025

Sold

New England Real Estate Network #5058796

$500,000—
Nov 26, 2025

Pending

New England Real Estate Network #5058796

—
Aug 29, 2025

Listed (Active)

New England Real Estate Network #5058796

$495,000—
Jul 24, 2023

Sold (Public Record)

Public Record #1515889073

$540,000—
Jul 24, 2023

Sold

New England Real Estate Network #4934077

$540,000—
May 24, 2023

Active Under Contract

New England Real Estate Network #4934077

—
Oct 18, 2022

Listed (Active)

New England Real Estate Network #4934077

$550,000—
DateEvent & SourcePrice
11/26/2025

Sold

New England Real Estate Network #5058796

$500,000
11/26/2025

Pending

New England Real Estate Network #5058796

—
08/29/2025

Listed (Active)

New England Real Estate Network #5058796

$495,000
07/24/2023

Sold (Public Record)

Public Record #1515889073

$540,000
07/24/2023

Sold

New England Real Estate Network #4934077

$540,000
05/24/2023

Active Under Contract

New England Real Estate Network #4934077

—
10/18/2022

Listed (Active)

New England Real Estate Network #4934077

$550,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 374 Winhall Hollow Road

Taxable ValueLand$126,000Additions$128,300Total$254,300
Tax Record2024$7,120 ($593 / month)
Home Facts
Baths1.5Total Finished SqFt960 SqFtAbove Grade Finished SqFt960 SqFtUnfinished Basement SqFt560 SqFtLot Size631,620 SqFtStyleMobile / Manufactured HomeYear Built1986CountyBENNINGTONAPN(245)01480Fireplace TypeHas Fireplace

Schools near 374 Winhall Hollow Road

Rating
School
Type
Grades
Distance
Mountain School At Winhall
Private - K to 8
Rating
School
Distance
Mountain School At Winhall
PrivateK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of Real Broker LLC

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 01/01/2026 12:16 PM