OFF MARKET

Listed by Terry Hill • Berkshire Hathaway HomeServices Stratton Home. Bought with Four Seasons Sotheby's Int'l Realty.

Off market dec 2021 for $1.5M

$2,023,194

Est. refi paymentEst. refi $10,138/mo

•

5,400

sq ft

21 Hollow View Rd, Winhall, VT 05340

About this home

Forever vista views of the Winhall Valley from this custom 5 bedroom mountain home off Upper Taylor Hill Road in Winhall. You will appreciate the multi level living space including a main floor guest suite, entertainer's kitchen with island and even two dishwashers for your large gatherings. Right off the kitchen island is a welcoming dining/living area, and access to an inviting screened in porch. Wide pine flooring compliments the main first floor. Master bedroom boasting wide views and second guest suite reside on the upper level. The lower level offers a fourth bedroom, den/library room , a shared bath and fun recreation room with polished bar and second fireplace. Walk out to the lower level covered patio from this level. Attached two car garage allows you to enter into a generous size mudroom. Full house generator. Most recent improvements include new furnace, new hot water heater, new carpet on lower level, freshly stained decks and a brand new sunken hot tub. If your home search consists of a well maintained property with attractive furnishings, FABULOUS VIEWS within minutes to Stratton's Base Lodge or Sun Bowl we've got just the place for you. Look no further.

Single-familyProperty Type

2006Year Built

5.79 acresLot Size

$375Est. Price/Sq.Ft.

2 car garageParking

Listed by Terry Hill • Berkshire Hathaway HomeServices Stratton Home

Bought with Steve Stettler • Four Seasons Sotheby's Int'l Realty

Redfin checked: a minute ago

•Source:PrimeMLS #4888237

Redfin Estimate

$2,023,194

$473K since sold in December 2021$23K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 53.9% higher than the average sale price ($1.31M) of 6 comparable homes.

SOLD SEP 15, 2026
$1,299,000
A
4 beds4 baths3,644 sq ft
279 French Hollow Rd, Winhall, VT 05340
SOLD OCT 2, 2026
$725,000
B
4 beds4 baths3,520 sq ft
12 Stratton Ridge Rd, Winhall, VT 05340
SOLD OCT 30, 2026
$2,350,000
C
5 beds3.5 baths4,752 sq ft
6 Sunset Ridge Rd, Winhall, VT 05340
SOLD FEB 12, 2026
$2,150,000
D
4 beds4.5 baths5,000 sq ft
16 Hunters Rdg, Winhall, VT 05340
SOLD SEP 29, 2026
$785,000
E
4 beds3.5 baths2,878 sq ft
32 Benson Fuller Dr, Winhall, VT 05340
SOLD AUG 17, 2026
$580,000
F
4 beds3 baths3,700 sq ft
53 Country Ln, West Wardsboro, VT 05360

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,071/mo

Redfin rental estimate

List your home for rent

Market trends in 05340, VT

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

98.2%

1.9% MoM

Median sale price

$725K

$53K MoM

Avg. days on market

71d

5 days MoM

Recently sold homes

2 MoM

New listings for sale

$699,000
4 beds2 baths1,598 sq ft
19 Stratton View Rd, Winhall, VT 05340
$599,000
4 beds2 baths1,680 sq ft
15 Stratton View Rd, Bondville, VT 05340
$6,950,000
8 beds9 baths8,690 sq ft
95 Winhall Hollow Rd, Winhall, VT 05340
See all

Provided by Redfin

Sale history for 21 Hollow View Rd

Year

Property tax

Land + Additions

Assessment*

2025

$19,926 (−0.8%)

$319,900 + $633,100

$953,000

2024

$20,088 (+18.4%)

$319,900 + $633,100

$953,000

2023

$16,973 (−15.6%)

$319,900 + $633,100

$953,000

2022

$20,099 (−2.6%)

$319,900 + $633,100

$953,000

2021

$20,642

$319,900 + $633,100

$953,000

2020

$20,662 (+5.3%)

$319,900 + $633,100

$953,000

2019

$19,613 (+6.0%)

$319,900 + $633,100

$953,000

2018

$18,496 (−0.7%)

$319,900 + $633,100

$953,000

2017

$18,618 (−4.3%)

$319,900 + $633,100

$953,000

2016

$19,445 (+2.3%)

$319,900 + $633,100

$953,000

2015

$19,001

$319,900 + $633,100

$953,000

2013

$319,900 + $633,100

$953,000

Tax history for 21 Hollow View Rd

Year

Property tax

Land + Additions

Assessment*

2025

$19,926 (−0.8%)

$319,900 + $633,100

$953,000

2024

$20,088 (+18.4%)

$319,900 + $633,100

$953,000

2023

$16,973 (−15.6%)

$319,900 + $633,100

$953,000

2022

$20,099 (−2.6%)

$319,900 + $633,100

$953,000

2021

$20,642

$319,900 + $633,100

$953,000

2020

$20,662 (+5.3%)

$319,900 + $633,100

$953,000

2019

$19,613 (+6.0%)

$319,900 + $633,100

$953,000

2018

$18,496 (−0.7%)

$319,900 + $633,100

$953,000

2017

$18,618 (−4.3%)

$319,900 + $633,100

$953,000

2016

$19,445 (+2.3%)

$319,900 + $633,100

$953,000

2015

$19,001

$319,900 + $633,100

$953,000

2013

$319,900 + $633,100

$953,000

*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

—

Stories

—

Lot width

—

Lot depth

—

Lot size

5.79 Acres

Year renovated

—

Sq. Ft.

2,916

Year built

—

Style

Single Family Residential

County

Bennington County

APN

77124512239

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 22, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 2
Location: Attached
Auto Open, Direct Entry

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Walkout
Finished, Stairs - Interior, Walkout, Exterior Access

Other Interior Features
# of Rooms: 9
Level B: Bedroom, Level B: Library, Level B: Rec Room
Flooring: Carpet, Softwood, Tile
Water Heater: Domestic
Central Vacuum, Blinds, Ceiling Fan, Draperies, Fireplace - Wood, Fireplaces - 2, Furnished, Hearth, Hot Tub, Kitchen Island, Living/Dining, Master Bedroom With Bath

Accessibility Information
1st Floor 1/2 Bathroom, 1st Floor 3/4 Bathroom, 1st Floor Bedroom

Equipment & Appliance Information
Dishwasher - Energy Star, Dryer, Microwave, Range - Gas, Washer, Wine Cooler
Carbon Monoxide Detector, Security System, Smoke Detectr-Hard Wired With Battery, Generator - Standby

Room 1 Information
Mudroom
Mudroom
Dimensions: 13 x 18
Level: 1

Room 2 Information
Kitchen
Dimensions: 12 x 13
Level: 1

Room 3 Information
Dining Room
Dimensions: 12 x 22.5
Level: 1

Room 4 Information
Living Room
Dimensions: 22.5 x 16
Level: 1

Room 5 Information
Bedroom
Dimensions: 13.5 x 15
Level: 1

Room 6 Information
Master Bedroom Suite
Master Bedroom Suite
Dimensions: 25 x 14
Level: 2

Room 7 Information
Bedroom
Dimensions: 11 x 12
Level: 2

Room 8 Information
Bedroom
Dimensions: 14 x 15
Level: Basement

Room 9 Information
Library
Dimensions: 10.5 x 17
Level: Basement

Room 10 Information
Rec Room
Dimensions: 25 x 25
Level: Basement

Room 11 Information
Porch
Level: 1

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 5400
Approximate Sq. Ft. Total: 5400
Color: Natural
Deck, Window Screens, Windows - Double Pane
Construction: Wood Frame
Foundation: Poured Concrete
Roof: Shingle - Architectural
Exterior: Clapboard, Stone, Wood Siding

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot: 64.1
Easements: Unknown
Landscaped, Level, Mountain View, Sloping, View, Wooded

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 2006

Financial

Tax Information
Tax Year: 2021
Gross Amount Tax: 20641.98
SPAN Number: 771-245-12239

Other Tax Information
Page Deed: 243-246

Utilities

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

Sewer Information
Leach Field, Septic

Electric Information
Electric Company: GMP
220 Plug

Water Information
Drilled Well

Other Utilities Information
Cable Company: Comcast
Fuel Company: Suburban
Cable, Gas - LP/Bottle

Location

Homeowners Association
Fee: 650
Seasonal
Plowing
Association Amenities: Snow Removal

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

Road Information
Road Frontage: Yes
Road Frontage Length: 299
Private, Privately Maintained

Other Location Information
Directions: Stratton Access Road to Upper Taylor Hill Take private Hollow View Road on your left First home on left
Block: 02

Public facts

Beds: —
Baths: —
Sq. Ft.: 2,916
Stories: —
Lot Size: 5.79 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Bennington County
APN: 77124512239

Home facts updated by county records on Oct 22, 2026

Around this home

Schools

K - 12
Preschool & daycare

Mountain School At Winhall

Private K-7 • 1.2mi

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 85° expected this year, 20 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)

22°

11°

26°

12°

42°

25°

53°

34°

59°

44°

72°

55°

76°

60°

73°

55°

69°

50°

56°

39°

42°

30°

29°

16°

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

$1.92M – $2.33M

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

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NEW CONSTRUCTION

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Open-concept layout • 12x24 back deck • Finished lower level

New listings for sale in 05340

$699,000

4 beds2 baths1,598 sq ft

19 Stratton View Rd, Winhall, VT 05340

Ev charging station • Heated entry stairs • Multiple wood stoves

$599,000

4 beds2 baths1,680 sq ft

15 Stratton View Rd, Bondville, VT 05340

Updated kitchens • Updated baths • Fully furnished

$6,950,000

8 beds9 baths8,690 sq ft

95 Winhall Hollow Rd, Winhall, VT 05340

23 acres • Sweeping views • Completely renovated

Home values near 21 Hollow View Rd

Data from public records.

Address	Redfin Estimate
14 Hollow View Rd, Winhall, VT 3 Beds \| 3.5 Baths \| 3368 Sq. Ft.	$1,216,867
15 Pearl Buck Dr, Winhall, VT 4 Beds \| 3 Baths \| 3533 Sq. Ft.	$912,093
136 Benson Fuller Dr, Winhall, VT 4 Beds \| 2 Baths \| 1736 Sq. Ft.	$552,226
37 Upper Taylor Hill Rd, Jamaica, VT 4 Beds \| 4.5 Baths \| 3640 Sq. Ft.	$991,558
4 Pearl Buck Dr, Winhall, VT 3 Beds \| 2 Baths \| 1455 Sq. Ft.	$653,441
69 Upper Taylor Hill Rd, Winhall, VT 4 Beds \| 4.5 Baths \| 6471 Sq. Ft.	$2,769,627
67 Upper Taylor Hill Rd, Winhall, VT 4 Beds \| 3 Baths \| 3552 Sq. Ft.	$915,361

Address	Redfin Estimate
18 Hollow View Rd, Winhall, VT 3 Beds \| 2.5 Baths \| 3787 Sq. Ft.	$2,351,534
122 Benson Fuller Dr, Winhall, VT 7 Beds \| 5 Baths \| 5100 Sq. Ft.	$1,296,019
65 Lower Taylor Hill Rd, Jamaica, VT 3 Beds \| 2 Baths \| 912 Sq. Ft.	$435,708
3 Mountain Haunts Rd, Winhall, VT 2 Beds \| 3.5 Baths \| 2433 Sq. Ft.	$652,575
67 Upper Taylor Hill Rd, Jamaica, VT 3 Beds \| 4 Baths \| 2644 Sq. Ft.	$835,727
28 Mountain Haunts Rd, Winhall, VT 4 Beds \| 4 Baths \| 3390 Sq. Ft.	$913,760
69 Upper Taylor Hill Rd, Winhall, VT 8 Beds \| 8.5 Baths \| 7562 Sq. Ft.	$3,563,023

Address	Redfin Estimate
48 Upper Taylor Hill Rd, Jamaica, VT 4 Beds \| 4.5 Baths \| 3224 Sq. Ft.	$1,835,051
130 Benson Fuller Dr, Winhall, VT 3 Beds \| 2 Baths \| 2576 Sq. Ft.	$662,033
29 Upper Taylor Hill Rd, Jamaica, VT 3 Beds \| 2 Baths \| 1367 Sq. Ft.	$441,574
114 Benson Fuller Dr, Winhall, VT 5 Beds \| 4.5 Baths \| 2900 Sq. Ft.	$852,826
7 Woodrock Rd, Winhall, VT 3 Beds \| 2 Baths \| 976 Sq. Ft.	$722,363
57 Upper Taylor Hill Rd, Winhall, VT 5 Beds \| 5.5 Baths \| 6479 Sq. Ft.	$2,724,613
64 Upper Taylor Hill Rd, Jamaica, VT 5 Beds \| 3.5 Baths \| 3503 Sq. Ft.	$1,502,037

Property information provided by PrimeMLS when last listed in 2021. 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 21 Hollow View Rd

Tax history for 21 Hollow View 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 21 Hollow View Rd

More real estate resources