OFF MARKET

Listed by Elyn Bischof • Berkshire Hathaway HomeServices Stratton Home. Bought with Winhall Real Estate.

Off Market Nov 2022 for $2.3M

$2,346,344

•

3,375

sq ft

103 Winhall Hollow Rd, Winhall, VT 05340

About this home

SOME OPPORTUNITIES ONLY COME ALONG ONCE IN A LIFETIME! THIS IS YOUR CHANCE! COME SEE THE HISTORIC RED FOX INN! A unique, unrivaled Vermont offering located on the famed Winhall Hollow Rd. With 10.1 gorgeous acres boasting beautiful open meadows, spacious grounds and views of Stratton, this property has a 3375 sq. ft, 9 BR 8 bath + living room Guesthouse, a magnificent 6484' Barn with 75 seat restaurant and Irish Pub, always the go to place for great food, great music and a great time! Also, there is a 1600' 3 BR carriage house used for living quarters, a 5 bay garage and a 1.53a. lot permitted for 4 BR home. The best part? State wastewater Permits are in place for all of this! Use your imagination and creativity to make this your own! You can even renovate the guesthouse to become your new dream home all the while experiencing living in a tranquil setting. The current owners have been the steadfast Innkeepers of this precious gem for the last 40 years and have raised their children here in this sought after School Choice Winhall community. This property is 5 min. to Stratton, 15 min to Bromley, 30 min to Mt. Snow, 45 min to Okemo, 60 min to Killington. It is close to golf, tennis, swimming, hiking, paddleboarding, Manchester and is part of a large arts community as well. Only 4.5 hrs to NYC, 1.25 to Albany, 2.5 hrs to Burlington, 3 hrs to Boston. YOUR VISION CAN BE YOUR ANSWER TO HAVING A PEACEFUL ENVIRONMENT, GREAT SCHOOLS AND A LESS HECTIC LIFE! WHAT ARE YOU WAITING FOR?

Single-familyProperty Type

1850Year Built

10.1 acresLot Size

$695Est. Price/Sq.Ft.

5 car garageParking

Listed by Elyn Bischof • Berkshire Hathaway HomeServices Stratton Home

Bought with Carrie Mathews • Winhall Real Estate

Redfin checked: a few seconds ago

•Source:PrimeMLS #4931129

Redfin Estimate

$2,346,344

$19K since sold in November 2022$97K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 103.5% higher than the average sale price ($1.15M) of 6 comparable homes.

SOLD JUL 17, 2026
$799,000
A
4 beds3.5 baths3,078 sq ft
63 Raspberry Hill Rd, Winhall, VT 05340
SOLD APR 10, 2026
$1,550,000
B
5 beds4 baths4,000 sq ft
147 High Meadow Rd #147, Winhall, VT 05340
SOLD JUL 27, 2026
$1,287,500
C
4 beds3.5 baths4,153 sq ft
487 Vermont Route 100, South Londonderry, VT 05155
SOLD MAY 8, 2026
$1,875,000
D
4 beds4.5 baths2,486 sq ft
97 N Brookwood Rd, Stratton, VT 05155
SOLD MAY 1, 2026
$735,000
E
4 beds3 baths2,091 sq ft
5 Wall St, Winhall, VT 05340
SOLD JUL 6, 2026
$670,500
F
4 beds3 baths2,400 sq ft
30 Upper Woods and Water Rd, Winhall, VT 05340

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Earn from this home

Rent

$2,719/mo

Redfin rental estimate

List your home for rent

Market trends in 05340, VT

Last updated July 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.5%

+0.2% MoM

Median sale price

$735K

$166 MoM

Avg. days on market

83d

8 days MoM

Recently sold homes

3 MoM

New listings for sale

COMING SOON
$599,000
3 beds2 baths1,890 sq ft
33 Burnt Hill Rd, Winhall, VT 05340
$345,000
2 beds2 baths960 sq ft
19 Winhall Condo Rd #4, Winhall, VT 05340
$2,399,000
4 beds3.5 baths4,536 sq ft
33 Stone Lodge Rd, Winhall, VT 05340
$595,000
3 beds2 baths1,416 sq ft
23 Loop Rd #10, Bondville, VT 05340
$399,000
3 beds2 baths1,225 sq ft
16B Bromley Knolls Rd Unit B, Winhall, VT 05340
See all

Provided by Redfin

Sale history for 103 Winhall Hollow Rd

Public record

Public record
Zoning

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

—

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Bennington County

APN

771-245-10397

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 24, 2023.

Property details

Parking

Parking & Garage
Garage Capacity: 5
Location: Detached
Garage, Parking Spaces 21+, Unpaved

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 4
# of Baths (3/4): 4

Basement Information
Basement: Yes
Basement Access: Interior
Bulkhead, Concrete, Stairs - Interior, Unfinished, Interior Access

Other Interior Features
# of Rooms: 10
Flooring: Carpet, Tile, Vinyl, Wood
Water Heater: Oil, Tank
Fireplace - Wood, Fireplaces - 2, Furnished, Master Bedroom With Bath, Whirlpool Tub

Equipment & Appliance Information
Carbon Monoxide Detector, Smoke Detector

Room 1 Information
Living Room
Living Room
Level: 1

Room 2 Information
Bedroom
Level: 1

Room 3 Information
Bedroom
Level: 1

Room 4 Information
Bedroom
Level: 1

Room 5 Information
Bedroom
Level: 2

Room 6 Information
Bedroom
Bedroom
Level: 2

Room 7 Information
Bedroom
Level: 2

Room 8 Information
Bedroom
Level: 2

Room 9 Information
Bedroom
Level: 2

Room 10 Information
Bedroom
Level: 2

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 3375
Approximate Sq. Ft. Total: 5115
Color: white
Barn, Guest House, Outbuilding, Porch - Covered
Construction: Wood Frame
Foundation: Concrete, Stone
Roof: Shingle
Exterior: Clapboard, Wood

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot: 01.120
Country Setting, Field/Pasture, Mountain View, Open, View, Wooded

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1850

Financial

Tax Information
Tax Year: 2022
Gross Amount Tax: 18453.76
SPAN Number: 771-245-10397

Other Tax Information
Page Deed: tbd

Financing Information
Possible Options: Cash, Conventional

Utilities

Heating & Cooling Information
Heat: Baseboard, Hot Water
Heat Fuel: Oil

Sewer Information
Leach Field, Replacement Field-OnSite

Electric Information
Electric Company: Green Mt. Power
Circuit Breaker(s)

Water Information
Drilled Well, On-Site Well Exists

Other Utilities Information
Cable Company: Comcast
Fuel Company: Cota and Cota
Cable, Internet - Cable, Oil Tank - Underground

Location

School Information
Elementary School: Choice
Elementary School: Choice
Middle/Jr School: Choice

Neighborhood Information
Near Golf Course, Near Skiing, Rural

Road Information
Road Frontage: Yes
Road Frontage Length: 718
Paved, Public

Other Location Information
Directions: From Bondville, take Winhall Hollow Rd. Red Fox is on the left. See sign.
Block: 03

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: —
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Bennington County
APN: 771-245-10397

Home facts updated by county records on Jun 24, 2023

Other

Water Body Information
Flood Zone: Unknown

Documents & Disclosures
Documents Available: Deed, State Wastewater Permit, Survey, Tax Map

Around this home

Schools

Mountain School At Winhall

Private K-8 • 0.5mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

Flood Factor

We're working on getting current and accurate flood risk information for this home.

Fire Factor

We're working on getting current and accurate fire risk information for this home.

1/10 Heat Factor

8 hot days expected this year, 19 days in 30 years

Wind Factor

We're working on getting current and accurate wind risk information for this home.

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winhall, VT • 05340

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.2 hours in June and 3.5 hours in December, placing it below the U.S. average for solar exposure.

8.2 hrs

3.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.23M – $2.70M

Sell confidently with a local market expert in Winhall. 3 minutes to get started.

Nearby similar homes

$549,000

4 beds2.5 baths2,359 sq ft

116 Teacher Rd, Jamaica, VT 05343

VIDEO TOUR

$1,200,000

Studio1 bath950 sq ft

109 Winhall Hollow Rd, Winhall, VT 05340

$875,000

3 beds2 baths1,600 sq ft

447 Rock Bottom Ln, Peru, VT 05255

$1,399,999

6 beds4 baths3,800 sq ft

121 High Meadow Rd, Winhall, VT 05340-9999

$4,500,000

5 beds5.5 baths5,700 sq ft

24 Sawmill Rd, Stratton, VT 05155

$565,000

3 beds2 baths1,814 sq ft

1886 Winhall Hollow Rd, South Londonderry, VT 05155

New listings for sale in 05340

COMING SOON

$599,000

3 beds2 baths1,890 sq ft

33 Burnt Hill Rd, Winhall, VT 05340

$345,000

2 beds2 baths960 sq ft

19 Winhall Condo Rd #4, Winhall, VT 05340

$2,399,000

4 beds3.5 baths4,536 sq ft

33 Stone Lodge Rd, Winhall, VT 05340

$595,000

3 beds2 baths1,416 sq ft

23 Loop Rd #10, Bondville, VT 05340

$399,000

3 beds2 baths1,225 sq ft

16B Bromley Knolls Rd Unit B, Winhall, VT 05340

Home values near 103 Winhall Hollow Rd

Data from public records.

Address	Redfin Estimate
82 Winhall Hollow Rd, Winhall, VT 4 Beds \| 1.5 Baths \| 1918 Sq. Ft.	$619,230
70 Winhall Hollow Rd, Winhall, VT 4 Beds \| 3.5 Baths \| 3150 Sq. Ft.	$1,100,240

Address	Redfin Estimate
95 Winhall Hollow Rd, Winhall, VT 7 Beds \| 9.5 Baths \| 6721 Sq. Ft.	$2,675,136
109 Winhall Hollow Rd, Winhall, VT - Beds \| 1 Baths \| 950 Sq. Ft.	—

Address	Redfin Estimate
73 Winhall Hollow Rd, Winhall, VT 4 Beds \| 3.5 Baths \| 3852 Sq. Ft.	$1,137,658
16 Stratton View Rd, Winhall, VT 3 Beds \| 2.5 Baths \| 1992 Sq. Ft.	$700,804

Property information provided by PrimeMLS when last listed in 2022. This data may not match . Learn more.

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