386 Winhall Hollow Road

Closed 11/4/22
Closed 11/4/22
Gallery Image 1
Gallery Image 2
Gallery Image 3
Gallery Image 4
Gallery Image 5
Gallery Image 6
Gallery Image 7
Gallery Image 8
Gallery Image 9
Gallery Image 10
Gallery Image 11
Gallery Image 12
Gallery Image 13
Gallery Image 14
Gallery Image 15
Gallery Image 16
Gallery Image 17
Gallery Image 18
Gallery Image 19
Gallery Image 20
Gallery Image 21
Gallery Image 22
Gallery Image 23
Gallery Image 24
Gallery Image 25
Gallery Image 26
Gallery Image 27
Gallery Image 28
Gallery Image 29
Gallery Image 30
Gallery Image 31
Gallery Image 32
Gallery Image 33
Gallery Image 34
Gallery Image 35
Gallery Image 36
Gallery Image 37
Gallery Image 38
Gallery Image 39
Gallery Image 40
Sold
Last Sold Price
$645,000
5 beds4,000 sqft
386 Winhall Hollow Rd, Winhall, VT 05340
Single FamilyProperty Type
6 acresLot Size
1987Year Built
$161/sq ftPrice per sq ft
2 carsParking Spaces

Description

Come make this 5 bedroom Winhall Hollow Road your new home or your home away from home. Set back from the road this beautiful 4000 sq ft home has enough room for a growing family or a gathered family for skiing adventures. Just minutes from Stratton Mountain and down the street from public access to Gale Meadow Pond, there are year round adventures ready to be explored from this well maintained home on 6 acres. The Pond is only a short stroll through the woods, along a beautiful mountain stream....Come make this 5 bedroom Winhall Hollow Road your new home or your home away from home. Set back from the road this beautiful 4000 sq ft home has enough room for a growing family or a gathered family for skiing adventures. Just minutes from Stratton Mountain and down the street from public access to Gale Meadow Pond, there are year round adventures ready to be explored from this well maintained home on 6 acres. The Pond is only a short stroll through the woods, along a beautiful mountain stream. Come park your car in the heated two car garage, kick off your ski gear and sit by the cozy fireplace. There's so much that this property and location have to offer, just in time for the winter season.

    Sold By Flex Realty

    • Listed by: Trent Stephens • Wohler Realty Group
    Listing closed: 11/04/2022 12:00 AM • Source: New England Real Estate Network, MLS#: 4927384

    Recent comparable sales

    Median sold price

    $770,000

    Avg days on market

    41

    Sale-to-list ratio

    95.9%

    Winhall, VT

    9 comparable properties found

    $810,000 | 15 Benson Fuller Drive, Winhall, VT 05340
    1/22
    1

    $810,000

    Sold 11/15/24

    5
    Bedrooms
    3,062
    Square Feet
    1.1
    Acres

    15 Benson Fuller Drive, Winhall, VT 05340

    $770,000 | 5 Stratton Ridge Road, Winhall, VT 05340
    1/29
    2

    $770,000

    Sold 07/18/25

    4
    Bedrooms
    3,676
    Square Feet
    1.2
    Acres

    5 Stratton Ridge Road, Winhall, VT 05340

    $668,000 | 32 Beaver Street, Winhall, VT 05340
    1/30
    3

    $668,000

    Sold 10/04/24

    4
    Bedrooms
    2,179
    Square Feet
    1.6
    Acres

    32 Beaver Street, Winhall, VT 05340

    $350,000 | 44 Lake Road, Winhall, VT 05340
    1/33
    4

    $350,000

    Sold 03/20/26

    5
    Bedrooms
    2,303
    Square Feet
    2.64
    Acres

    44 Lake Road, Winhall, VT 05340

    $575,000 | 2 Spruce High Road, Winhall, VT 05340
    1/27
    5

    $575,000

    Sold 08/15/25

    4
    Bedrooms
    2,448
    Square Feet
    2.1
    Acres

    2 Spruce High Road, Winhall, VT 05340

    $500,000 | 374 Winhall Hollow Road, Winhall, VT 05340
    1/21
    6

    $500,000

    Sold 11/26/25

    4
    Bedrooms
    1,920
    Square Feet
    9.5
    Acres

    374 Winhall Hollow Road, Winhall, VT 05340

    $975,000 | 20 Jamie Lane, Winhall, VT 05340
    1/57
    7

    $975,000

    Sold 11/27/25

    5
    Bedrooms
    3,500
    Square Feet
    1
    Acres

    20 Jamie Lane, Winhall, VT 05340

    $850,000 | 36 Rd To Millbrook, Winhall, VT 05340
    1/41
    8

    $850,000

    Sold 04/04/25

    4
    Bedrooms
    3,119
    Square Feet
    5.28
    Acres

    36 Rd To Millbrook, Winhall, VT 05340

    $799,000 | 63 Raspberry Hill Road, Winhall, VT 05340
    1/36
    9

    $799,000

    Sold 07/17/26

    4
    Bedrooms
    3,078
    Square Feet
    1.5
    Acres

    63 Raspberry Hill Road, Winhall, VT 05340

    Get preapproved with Rocket Mortgage1

    Location

    Add your commute

    Payment Calculator

    Get preapproved with Rocket Mortgage1

    $3,905 per month

    30 year fixed, 6.71% Interest

    Principal and Interest

    $3,333

    Property Taxes

    $572

    HOA Dues

    $0

    The Payment Calculator is for illustrative purposes only.

    Know your buying power with a preapproval and custom rate in minutes

    Rocket Mortgage1

    Property Information for 386 Winhall Hollow Road

    Property Details
    • Taxes: $6,861 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Parking: Garage
    • Zoning: residential
    Building Information
    • Stories: 2
    • Year Built: 1987
    • Lot Size: 6.00 AC / 261,360 SF
    Summary
    Location and General Information
    • City: Winhall
    • County: VT-Bennington
    • Directions: From Manchester, take Route 30 to French Hollow Road. French Hollow dead ends on Winhall Hollow turn left. House is third driveway on right. From Winhall take Route 30, right turn onto Winhall Hollow Rd. Follow for approximately 3.5 Miles. Just past French Hollow road, third driveway on right.
    • Latitude: 43.180001118297589
    • Longitude: -72.880107575393680
    • Road Frontage: No
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip Code: 05340
    Taxes and HOA Information
    • SPAN Number: 771-245-10456
    • Tax - Gross Amount: $6,860.58
    • Tax Year: 2022
    • Taxes TBD: No
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Gravel, Right-Of-Way (ROW)
    Property
    Lot Information
    • Lot - Sqft: 261360.0
    • Lot Size Acres: 6.0
    • Square Feet Apx Finished Above Grade: 4000.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Finished BG Source: Public Records
    • Square Feet Apx Total: 4000.0
    • Square Feet Apx Total Finished: 4000.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Public Records
    • Square Feet Apx Unfinished Below Grade: 0.0
    • Square Feet Apx Unfinished BG Source: Public Records
    Property and Assessments
    • Current Use: No
    • Property Class: Residential
    • Property Type: Single Family
    • Easements: No
    • Flood Zone: No
    • Foundation: Poured Concrete
    • PreConstruction: No
    • Resort: No
    • ROW - Length: 164
    • ROW - Parcel Access: Yes
    • ROW - Width: 50
    • Surveyed: Unknown
    • Year Built: 1987
    Utilities
    • Electric Company: Green Mountain Power
    • Cable Company: Xfinity
    • Fuel Company: Suburban Propane
    • Electric: 200 Amp
    • Sewer: 1000 Gallon, Septic
    • Utilities: Cable - Available, Fiber Optic Internt Avail, Gas - LP/Bottle, High Speed Intrnt -Avail, Internet - Fiber Optic, Phone, Telephone Available
    Interior and Exterior Features
    Exterior Features
    • Features - Exterior: Porch, Porch - Enclosed
    • Roads: Public
    • Roof: Metal
    Interior Features
    • Appliances: Dishwasher, Dryer, Microwave, Range - Gas, Refrigerator, Washer
    • Basement: Yes
    • Basement Access Type: Walkout
    • Basement Description: Finished, Stairs - Interior, Interior Access, Exterior Access
    • Baths - Total: 3
    • Baths - Full: 1
    • Half Baths: 0
    • One Quarter Baths: 0
    • Three Quarter Bath: 2
    • Rooms - Total: 9
    • Rooms: Level 1: Level 1: Bedroom, Level 1: Dining Room, Level 1: Family Room, Level 1: Kitchen/Dining, Level 1: Primary Bedroom
    • Rooms: Level B: Level B: Bedroom, Level B: Family Room
    • Bedrooms - Total: 5
    • Flooring: Carpet, Wood
    • Heat Fuel: Gas - LP/Bottle
    • Heating: Baseboard, Hot Water
    • Cooling: None
    • Total Stories: 2
    Room Information
    Room 1
    • Room Level: 1
    • Room Type: Dining Room
    Room 2
    • Room Level: 1
    • Room Type: Family Room
    Room 3
    • Room Level: 1
    • Room Type: Kitchen/Dining
    Room 4
    • Room Level: 1
    • Room Type: Primary Bedroom
    Room 5
    • Room Level: 1
    • Room Type: Bedroom
    Room 6
    • Room Level: Basement
    • Room Type: Family Room
    Room 7
    • Room Level: Basement
    • Room Type: Bedroom
    Room 8
    • Room Level: Basement
    • Room Type: Bedroom
    Room 9
    • Room Level: Basement
    • Room Type: Bedroom

    Property History for 386 Winhall Hollow Road

    DateEvent & SourcePriceAppreciation
    Nov 4, 2022

    Sold (Public Record)

    Public Record #1501990681

    		$645,000—
    Nov 4, 2022

    Sold

    New England Real Estate Network #4927384

    		$645,000—
    Sep 12, 2022

    Active Under Contract

    New England Real Estate Network #4927384

    		—
    DateEvent & SourcePrice
    11/04/2022

    Sold (Public Record)

    Public Record #1501990681

    $645,000
    11/04/2022

    Sold

    New England Real Estate Network #4927384

    $645,000
    09/12/2022

    Active Under Contract

    New England Real Estate Network #4927384

    —

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

    Public Records for 386 Winhall Hollow Road

    Taxable ValueLand$57,000Additions$257,100Total$314,100
    Tax Record2025$6,568 ($547 / month)
    Home Facts
    Beds2Baths2Total Finished SqFt2,304 SqFtAbove Grade Finished SqFt2,304 SqFtUnfinished Basement SqFt824 SqFtLot Size261,360 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(245)87018

    Schools near 386 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.

    Similar Homes

    New listings in 05340

    $910,000 | 7 Roundtree Road, Winhall, VT 05340
    1/41

    $910,000

    4
    Bedrooms
    3,031
    Square Feet
    1.37
    Acres

    7 Roundtree Road, Winhall, VT 05340

    $2,399,000 | 33 Stone Lodge Road, Winhall, VT 05340
    1/58
    Virtual Tour

    $2,399,000

    4
    Bedrooms
    4,536
    Square Feet
    2.5
    Acres

    33 Stone Lodge Road, Winhall, VT 05340

    $1,399,999 | 121 High Meadow Road, Winhall, VT 05340
    1/33

    $1,399,999

    6
    Bedrooms
    3,800
    Square Feet
    1
    Acres

    121 High Meadow Road, Winhall, VT 05340

    $649,000 | 39 Pond View Road, Unit 39, Winhall, VT 05340
    1/33
    Active Under Contract

    $649,000

    3
    Bedrooms
    1,650
    Square Feet

    39 Pond View Road, Unit 39, Winhall, VT 05340

    $1,200,000 | 109 Winhall Hollow Road, Winhall, VT 05340
    1/31
    Virtual Tour

    $1,200,000

    Unavailable
    Bedrooms
    950
    Square Feet
    23.5
    Acres

    109 Winhall Hollow Road, Winhall, VT 05340

    $2,500,000 | 59 Garden Loop Road, Winhall, VT 05340
    1/60
    Virtual Tour

    $2,500,000

    4
    Bedrooms
    3,762
    Square Feet
    3.43
    Acres

    59 Garden Loop Road, Winhall, VT 05340

    $1,160,000 | 82 North Brookwood Road, Stratton, VT 05340
    1/59

    $1,160,000

    5
    Bedrooms
    3,664
    Square Feet
    1.57
    Acres

    82 North Brookwood Road, Stratton, VT 05340

    $1,225,000 | 153 High Meadow Road, Winhall, VT 05340
    1/47

    $1,225,000

    4
    Bedrooms
    3,357
    Square Feet
    1.2
    Acres

    153 High Meadow Road, Winhall, VT 05340

    $1,100,000 | 6 Old Ridge Road, Winhall, VT 05340
    1/39
    Virtual Tour

    $1,100,000

    5
    Bedrooms
    4,453
    Square Feet
    1
    Acres

    6 Old Ridge Road, Winhall, VT 05340

    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 386 Winhall Hollow Road, Winhall, VT 05340
    $645,000
    5
    4,000
    261,360
    0 French Hollow, Winhall, VT 05340
    $212,000
    1
    325
    522,720
    374 Winhall Hollow Road, Winhall, VT 05340
    $500,000
    4
    1,920
    413,820
    381 Winhall Hollow Road, Bondville, VT 05340
    $399,000
    5
    4
    2,840
    221,285
    383 Winhall Hollow Road, Winhall, VT 05340
    $375,000
    3
    1,470
    226,512
    8 Smith Meadow Road, Bondville, VT 05340
    –
    3
    2
    1,648
    217,800

    Explore Nearby Homes

    No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

    Listing Courtesy of Wohler Realty Group

    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 09/21/2026 01:50 AM