$595,000
 $3,194 est/mo Sourced by Back At You

23 Loop Road,Winhall, VT 05340

Winhall, VT 05340

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Description

Set among sun-dappled woodlands along a peaceful country road, this distinctive post-and-beam home captures the charm of a Vermont sugar shack with the warmth of a classic ski-country retreat. This furnished three bedroom, two bath home offers 1,416 sq ft of inviting living space, thoughtfully designed for both full-time living and memorable getaways. Inside, the vaulted Great Room immediately draws you in with soaring ceilings, warm wood floors, exposed beams, and a dramatic stone fireplace with hearth and wood-storage nook, the ideal gathering place after a day on the slopes or a summer hike. The open kitchen features a breakfast bar and custom stained-glass bar cabinet, creating an inviting space for entertaining. A slider opens to the expansive 400 sq ft deck, where tranquil pond views set the stage for morning coffee, summer dinners, or quiet evenings under the stars.The main level includes a screened porch, welcoming mudroom, bunk room, guest bedroom with deck access, full bath, and laundry closet. Upstairs, a windowed landing leads to a charming loft overlooking the Great Room, offering a cozy reading or relaxation area and generous storage. The vaulted primary suite is a private retreat with his-and-hers closets, sitting area, and en-suite with sauna.Custom wrought-iron fixtures and abundant woodwork enhance the home's warm, authentic character and complement the home's woodland setting. Offered furnished, this turnkey Vermont getaway is equally suited to full-time living, a second home, or a memorable vacation retreat.Enjoy breathtaking views of Stratton Mountain beyond nearby horse-farm paddocks, on your way to Stratton's four-season activities, Manchester's renowned shopping and dining, and Southern Vermont's many outdoor adventures and cultural offerings. Trails toward Gale Meadow Pond are just down Winhall Hollow Road. A unique Southern Vermont retreat ready to create memories for years to come.

Details

MLS #5105544
Listing TypeFor Sale
StyleHouse
Sub-TypeResale
Status(31) Under Contract - Active Under Contract
Year1978
Days On Site50
Listing Provided ByFour Seasons Sotheby's Int'l Realty | Diana Stugger

Features

Bed(s)3
Bath(s) 2 Total
BasementY
Story(s)1
ZoningRural Residential Agric.
Acreage1.78

Interior

Rooms Total5
CoolingNone
HeatingForced Air
Interior FeaturesCathedral Ceiling(s), Dining Area, Draperies, Fireplace Screens/Equip, Wood Fireplace, 1 Fireplace, Furnished, Hearth, Kitchen/Dining, Lead/Stain Glass, Living/Dining, Primary BR w/ BA, Natural Woodwork, Sauna, Skylight, Vaulted Ceiling(s), Window Treatment, 1st Floor Laundry
AppliancesElectric Cooktop, Dishwasher, Dryer, Refrigerator, Washer, Electric Stove, Domestic Water Heater

Exterior

Exterior FeaturesDeck, Invisible Pet Fence, Natural Shade, Screened Porch, Shed, Window Screens
RoofAsphalt Shingle
Construction MaterialsWood Frame, Wood Exterior, Wood Siding
Foundation DetailsInsulated Concrete Forms
Lot FeaturesCountry Setting, Landscaped, Level, Pond on Lot, Subdivided, Wooded, Near Skiing
Accessibility Features1st Floor Bedroom, 1st Floor Full Bathroom, Accessible Washer/Dryer, Bathroom w/Tub, Hard Surface Flooring, Low Pile Carpet, 1st Floor Laundry

Parking

Garage Yes / NoNo

Utilities

UtilitiesCable, Phone Connected, Phone
ElectricCircuit Breakers
Sewer1000 Gallon, Existing Leach Field

Taxes

Tax Annual Amount7102.39
Tax Rate2.51
Tax Assessed Value557400
Tax Block02
Tax Lot77
Tax Year2026

Area Information

StateVT
CountyBennington
CityWinhall
Zip Code05340
AreaVT Bennington
Community NameVermont Ventures
School DistrictWinhall School District
Elementary SchoolChoice
High SchoolChoice
Listing VS Median (in Vermont Ventures)
Price:
$595,000
low | high
Med:
$0
On site:
50
low | high
Med:
Sourced by Back At You

Market Activity 05340

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Learn More About This Property

StateVT
CountyBennington
CityWinhall
Zip Code05340
AreaVT Bennington
Community NameVermont Ventures
School DistrictWinhall School District
Elementary SchoolChoice
High SchoolChoice
Listing VS Median (in Vermont Ventures)
Price:
$595,000
low | high
Med:
$0
On site:
50
low | high
Med:
Sourced by Back At You
Listing Updated: September 29, 2026 at 6:10:45 AM PDT