OFF MARKET

Listed by Kevin Moran • Four Seasons Sotheby's Int'l Realty. Bought with Four Seasons Sotheby's Int'l Realty.

Off Market Nov 2023 for $2.2M

$2,675,136

Est. refi paymentEst. refi $14,112/mo

•

6,721

sq ft

95 Winhall Hollow Rd, Winhall, VT 05340

About this home

Nestled on 23 acres of secluded natural beauty with breathtaking mountain vistas, this custom-crafted estate offers a blend of comfort and leisure. Equestrian enthusiasts will appreciate the horse facilities, including a three-stall barn and a fenced paddock. The barn's versatility allows it to serve as a party space or extra storage as needed. A spacious three-car attached garage complements the property, while a charming stone patio and perennial gardens create an outdoor oasis where relaxation and functionality harmonize. Step indoors, and you'll find a home filled with exquisite features. The kitchen is a culinary masterpiece, the great room boasts a stone fireplace, and the billiard room invites friendly competition. The residence features high ceilings throughout and boasts seven ensuite bedrooms, ensuring maximum comfort and privacy for residents and guests alike. The inviting three-season porch hints at opportunities for entertaining in this private retreat. Conveniently located near Stratton, Bromley, and Magic resorts, this property is a dream for winter sports enthusiasts. It embodies a tranquil mountain lifestyle, seamlessly blending natural beauty with the comforts of upscale living.

Single-familyProperty Type

2001Year Built

23 acresLot Size

$398Est. Price/Sq.Ft.

3 car garageParking

Listed by Kevin Moran • Four Seasons Sotheby's Int'l Realty

Bought with Andrea Kaplan • Four Seasons Sotheby's Int'l Realty

Redfin checked: a minute ago

•Source:PrimeMLS #4968392

Redfin Estimate

$2,675,136

$425K since sold in November 2023$101K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 14.4% higher than the average sale price ($2.34M) of 6 comparable homes.

SOLD MAY 22, 2026
$2,850,000
A
4 beds6 baths5,082 sq ft
41 Stark Farm Rd, Winhall, VT 05340
SOLD OCT 14, 2025
$2,200,000
B
5 beds6 baths7,625 sq ft
19 Old Town Rd, Winhall, VT 05340
SOLD FEB 12, 2026
$2,150,000
C
4 beds4.5 baths5,000 sq ft
16 Hunters Rdg, Winhall, VT 05340
SOLD SEP 25, 2025
$2,250,000
D
8 beds8.5 baths6,471 sq ft
69 Upper Taylor Hill Rd Unit D, Winhall, VT 05340
SOLD MAR 31, 2026
$3,025,000
E
6 beds5 baths6,437 sq ft
67 High Meadow Rd, Winhall, VT 05340
SOLD APR 10, 2026
$1,550,000
F
5 beds4 baths4,000 sq ft
147 High Meadow Rd #147, Winhall, VT 05340

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,400/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
$765,000
3 beds3 baths2,322 sq ft
72 Benson Fuller Rd, Winhall, VT 05340
See all

Provided by Redfin

Sale history for 95 Winhall Hollow Rd

Date

Event

Price

PrimeMLS #4968392

Nov 3, 2023

Sold

$2,250,000

$335/sq ft

Sep 28, 2023

Pending

—

Sep 20, 2023

Contingent

—

Sep 1, 2023

Listed

$2,350,000

$350/sq ft

Public Records

Jun 6, 2023

Sold

$1,900,000

$283/sq ft

PrimeMLS #3073983

Dec 15, 2010

Sold

$1,800,000

$268/sq ft

Sep 23, 2009

Listed

$1,995,000

$297/sq ft

Prestigious custom built home located on 23 private acres with mountain views, equestrian facilities, 3 car attached garage, stone patio and beautiful perennial gardens. This well contructed home features a beautiful kitchen with top of the line appliances, impressive great room with stone fireplace, billiard room, wine cellar, sunroom, exercise room, sauna and more too numerous to list. All measurements are approximate.

Year

Property tax

Land + Additions

Assessment*

2025

$31,345 (+2.2%)

$508,800 + $1,197,500

$1,706,300

2024

$30,676 (+11.1%)

$508,800 + $1,197,500

$1,706,300

2023

$27,606 (−15.6%)

$508,800 + $1,041,200

$1,550,000

2022

$32,690 (−2.6%)

$508,800 + $1,041,200

$1,550,000

2021

$33,573

$508,800 + $1,041,200

$1,550,000

2020

$33,606 (+5.3%)

$508,800 + $1,041,200

$1,550,000

2019

$31,899 (+6.0%)

$508,800 + $1,041,200

$1,550,000

2018

$30,082 (−0.7%)

$508,800 + $1,041,200

$1,550,000

2017

$30,281 (−4.3%)

$508,800 + $1,041,200

$1,550,000

2016

$31,627 (+2.3%)

$508,800 + $1,041,200

$1,550,000

2015

$30,905 (+3.4%)

$508,800 + $1,041,200

$1,550,000

2014

$29,892

$508,800 + $1,041,200

$1,550,000

2013

$508,800 + $1,041,200

$1,550,000

Tax history for 95 Winhall Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$31,345 (+2.2%)

$508,800 + $1,197,500

$1,706,300

2024

$30,676 (+11.1%)

$508,800 + $1,197,500

$1,706,300

2023

$27,606 (−15.6%)

$508,800 + $1,041,200

$1,550,000

2022

$32,690 (−2.6%)

$508,800 + $1,041,200

$1,550,000

2021

$33,573

$508,800 + $1,041,200

$1,550,000

2020

$33,606 (+5.3%)

$508,800 + $1,041,200

$1,550,000

2019

$31,899 (+6.0%)

$508,800 + $1,041,200

$1,550,000

2018

$30,082 (−0.7%)

$508,800 + $1,041,200

$1,550,000

2017

$30,281 (−4.3%)

$508,800 + $1,041,200

$1,550,000

2016

$31,627 (+2.3%)

$508,800 + $1,041,200

$1,550,000

2015

$30,905 (+3.4%)

$508,800 + $1,041,200

$1,550,000

2014

$29,892

$508,800 + $1,041,200

$1,550,000

2013

$508,800 + $1,041,200

$1,550,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

Baths

7.5

Stories

—

Lot width

—

Lot depth

—

Lot size

23.51 Acres

Year renovated

—

Sq. Ft.

7,042

Year built

2001

Style

Single Family Residential

County

Bennington County

APN

77124510702

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 3
Location: Attached
Auto Open

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 4
# of Baths (3/4): 5
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Interior
Other, Partially Finished, Stairs - Interior

Other Interior Features
# of Rooms: 17
Level B: Other, Level B: Playroom
Flooring: Carpet, Tile
Water Heater: Domestic, Gas - Liquid Propane Bottle
Bar, Blinds, Cedar Closet, Ceiling Fan, Fireplace - Screens/Equip, Fireplace - Wood, Fireplaces - 1, Master Bedroom With Bath, Sauna, Walk-in Closet, Walk-in Pantry, Wet Bar

Equipment & Appliance Information
Cooktop - Down-Draft, Dishwasher, Disposal, Dryer, Microwave, Oven - Double, Refrigerator, Washer
Humidifier, Satellite Dish, Security System, Smoke Detector

Room 1 Information
Mudroom
Mudroom
Dimensions: 9x8
Level: 1

Room 2 Information
Laundry Room
Dimensions: 5x7
Level: 1

Room 3 Information
Eat-In Kitchen
Dimensions: 16x24
Level: 1

Room 4 Information
Dining Room
Dimensions: 16x20
Level: 1

Room 5 Information
Sunroom
Dimensions: 14x15
Level: 1

Room 6 Information
Living Room
Living Room
Dimensions: 23x27
Level: 1

Room 7 Information
Rec Room
Dimensions: 18x21
Level: 1

Room 8 Information
Master Bedroom
Dimensions: 17x20
Level: 1

Room 9 Information
Bedroom with Bath
Dimensions: 14x16
Level: 2

Room 10 Information
Bedroom with Bath
Dimensions: 16x16
Level: 2

Room 11 Information
Bedroom with Bath
Dimensions: 12x14
Level: 2

Room 12 Information
Bedroom with Bath
Dimensions: 14x14
Level: 2

Room 13 Information
Bedroom with Bath
Dimensions: 11x15
Level: 2

Room 14 Information
Bedroom with Bath
Dimensions: 15x15
Level: 2

Room 15 Information
Playroom
Dimensions: 15x20
Level: Basement

Room 16 Information
Other
Dimensions: 10x20
Level: Basement

Room 17 Information
Other
Dimensions: 6x11
Level: 1

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 6721
Approximate Sq. Ft. Total: 7321
Color: White
Barn, Fence - Full, Fence - Partial, Outbuilding, Patio, Porch - Covered, Porch - Screened, Stable(s)
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle
Exterior: Clapboard

Driveway
Circular, Gravel

Lot, Zoning, & Easement Information
Common Land Acres: 0
Country Setting, Farm - Horse/Animal, Mountain View, Pond

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 2001

Financial

Tax Information
Tax Year: 2023
Gross Amount Tax: 37341.05
SPAN Number: 771-245-10702

Other Tax Information
Page Deed: 391

Utilities

Heating & Cooling Information
Cooling: Multi Zone
Heat: Baseboard, Hot Water, Multi Zone
Heat Fuel: Gas - Liquid Propane Bottle

Sewer Information
Septic

Electric Information
Electric Company: GMP
Circuit Breaker(s)

Water Information
Drilled Well

Other Utilities Information
Fuel Company: Haskins
Gas - LP/Bottle

Location

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

Road Information
Road Frontage: Yes
Road Frontage Length: 700
Public

Other Location Information
Directions: Route 30 to Winhall Hollow Road. No Drive by's

Public facts

Beds: 7
Baths: 7.5
Sq. Ft.: 7,042
Stories: —
Lot Size: 23.51 acres
Style: Single Family Residential
Year Built: 2001
Year Renovated: —
County: Bennington County
APN: 77124510702

Home facts updated by county records on Jul 15, 2026

Other

Documents & Disclosures
Documents Available: Deed

Around this home

Schools

Mountain School At Winhall

Private K-8 • 0.4mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

1/10 Heat Factor

8 days above 87° expected this year, 19 days in 30 years

3/10 Wind Factor

6% chance of strong winds in next 30 years

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

$2.54M – $3.08M

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

Nearby similar homes

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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

$765,000

3 beds3 baths2,322 sq ft

72 Benson Fuller Rd, Winhall, VT 05340

Home values near 95 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
73 Winhall Hollow Rd, Winhall, VT 4 Beds \| 3.5 Baths \| 3852 Sq. Ft.	$1,137,658
103 Winhall Hollow Rd, Winhall, VT 9 Beds \| 8 Baths \| 3375 Sq. Ft.	$2,346,344

Address	Redfin Estimate
64 Winhall Hollow Rd, Winhall, VT 3 Beds \| 2 Baths \| 1835 Sq. Ft.	$446,461
109 Winhall Hollow Rd, Winhall, VT - Beds \| 1 Baths \| 950 Sq. Ft.	—

Property information provided by PrimeMLS when last listed in 2023. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05340, VT

Sale history for 95 Winhall Hollow Rd

Tax history for 95 Winhall Hollow Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05340

Home values near 95 Winhall Hollow Rd

More real estate resources