SOLD OCT 14, 2025

Listed by Christiane Carroccio • TPW Real Estate. Bought with Berkshire Hathaway HomeServices Stratton Home.

Off Market Oct 2025 for $2.2M

$2,496,820

Est. refi paymentEst. refi $13,799/mo

•

7,625

sq ft

19 Old Town Rd, Winhall, VT 05340

About this home

Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain. The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking mountain vistas. A gourmet kitchen with high-end appliances, custom cabinetry, and ample workspace is perfect for entertaining. The den is a home office with a beautiful fireplace and built in bookcases. With five bedrooms each with their own bathroom, two half baths, thoughtfully designed living spaces, and high-end finishes throughout, this home seamlessly blends elegance and comfort. Enjoy privacy and seclusion while being just minutes from Stratton Resort, Magic Mountain, Bromley, and Manchester. This extraordinary property is a rare opportunity to own a piece of Vermont’s finest landscape.

Single-familyProperty Type

2000Year Built

21.53 acresLot Size

$327Est. Price/Sq.Ft.

2 car garageParking

Listed by Christiane Carroccio • TPW Real Estate

Bought with Lauren Behm • Berkshire Hathaway HomeServices Stratton Home

Redfin checked: a minute ago

•Source:PrimeMLS #5031720

Redfin Estimate

$2,496,820

$297K since sold in October 2025$6,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.2% higher than the average sale price ($2.08M) 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 FEB 12, 2026
$2,150,000
B
4 beds4.5 baths5,000 sq ft
16 Hunters Rdg, Winhall, VT 05340
SOLD MAY 22, 2026
$1,600,113
C
4 beds3.5 baths2,813 sq ft
264 French Hollow Rd, Winhall, VT 05340
SOLD APR 10, 2026
$1,550,000
D
5 beds4 baths4,000 sq ft
147 High Meadow Rd #147, 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 JUL 27, 2026
$1,287,500
F
4 beds3.5 baths4,153 sq ft
487 Vermont Route 100, South Londonderry, VT 05155

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Earn from this home

Refinance

Est. cash available

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Rent

$4,353/mo

Redfin rental estimate

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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
4 beds3 baths2,322 sq ft
72 Benson Fuller Rd, Winhall, VT 05340
See all

Provided by Redfin

Sale history for 19 Old Town Rd

Year

Property tax

Land + Additions

Assessment*

2025

$34,318 (−0.8%)

$477,200 + $1,164,100

$1,641,300

2024

$34,597 (+18.4%)

$477,200 + $1,164,100

$1,641,300

2023

$29,232 (−15.6%)

$477,200 + $1,164,100

$1,641,300

2022

$34,615 (−2.6%)

$477,200 + $1,164,100

$1,641,300

2021

$35,551

$477,200 + $1,164,100

$1,641,300

2020

$35,585 (+5.3%)

$477,200 + $1,164,100

$1,641,300

2019

$33,778 (+20.8%)

$477,200 + $1,164,100

$1,641,300

2018

$27,969 (−0.7%)

$277,000 + $1,164,100

$1,441,100

2017

$28,153 (−4.3%)

$277,000 + $1,164,100

$1,441,100

2016

$29,405 (+2.3%)

$277,000 + $1,164,100

$1,441,100

2015

$28,734 (+3.4%)

$277,000 + $1,164,100

$1,441,100

2014

$27,792

$277,000 + $1,164,100

$1,441,100

2013

$277,000 + $1,164,100

$1,441,100

Tax history for 19 Old Town Rd

Year

Property tax

Land + Additions

Assessment*

2025

$34,318 (−0.8%)

$477,200 + $1,164,100

$1,641,300

2024

$34,597 (+18.4%)

$477,200 + $1,164,100

$1,641,300

2023

$29,232 (−15.6%)

$477,200 + $1,164,100

$1,641,300

2022

$34,615 (−2.6%)

$477,200 + $1,164,100

$1,641,300

2021

$35,551

$477,200 + $1,164,100

$1,641,300

2020

$35,585 (+5.3%)

$477,200 + $1,164,100

$1,641,300

2019

$33,778 (+20.8%)

$477,200 + $1,164,100

$1,641,300

2018

$27,969 (−0.7%)

$277,000 + $1,164,100

$1,441,100

2017

$28,153 (−4.3%)

$277,000 + $1,164,100

$1,441,100

2016

$29,405 (+2.3%)

$277,000 + $1,164,100

$1,441,100

2015

$28,734 (+3.4%)

$277,000 + $1,164,100

$1,441,100

2014

$27,792

$277,000 + $1,164,100

$1,441,100

2013

$277,000 + $1,164,100

$1,441,100

*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

5.5

Stories

—

Lot width

—

Lot depth

—

Lot size

21.53 Acres

Year renovated

—

Sq. Ft.

6,625

Year built

—

Style

Single Family Residential

County

Bennington County

APN

77124510836

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 2

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Interior
Finished, Stairs - Interior, Storage Space

Other Interior Features
# of Rooms: 11
Level B: 1/2 Bath, Level B: Family Room

Room 1 Information
Kitchen
Kitchen
Dimensions: 12x8
Level: 1

Room 2 Information
Living Room
Dimensions: 35x24
Level: 1

Room 3 Information
Dining Room
Dimensions: 18x22
Level: 1

Room 4 Information
Master Bedroom
Dimensions: 20x20
Level: 1

Room 5 Information
Den
Dimensions: 17x16
Level: 1

Room 6 Information
Bedroom with Bath
Dimensions: 16x12
Level: 2

Room 7 Information
Bedroom with Bath
Dimensions: 16x12
Level: 2

Room 8 Information
Bonus Room
Dimensions: 20x17
Level: 2

Room 9 Information
Mudroom
Dimensions: 17x11
Level: 1

Room 10 Information
Family Room
Level: Basement

Room 11 Information
1/2 Bath
Level: Basement

Exterior

Building Information
Architectural Style: Adirondack, Contemporary
Construction Status: Existing
Construction Materials: Shake Siding, Stone Exterior
Approximate Sq. Ft. Total Finished: 7625
Approximate Sq. Ft. Total: 8625
Color: Gray
Roof: Shingle

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot Features: Country Setting, Landscaped, Mountain View, Secluded, Ski Area, View

Survey Information
Surveyed: Unknown

Other Property & Lot Information
Year Built: 2000

Financial

Tax Information
Tax Year: 2024
Gross Amount Tax: 45959
SPAN Number: 771-245-10836

Other Tax Information
Page Deed: 162

Utilities

Heating & Cooling Information
Heat: Oil, Baseboard, Radiant

Sewer Information
1000 Gallon, Septic

Electric Information
Circuit Breaker(s)

Water Information
Water Source: Drilled Well

Other Utilities Information
Internet: Fiber Optic Internt Avail, High Speed Intrnt -Avail
Cable - At Site, Telephone At Site

Location

School Information
School District: Bennington/Rutland
Elementary School: Choice
Elementary School: Choice
Middle/Jr School: Choice
School - High: Choice

Road Information
Road Frontage Type: Paved, Public

Other Location Information
Directions: From Manchester, take Route 30 toward Stratton. Make a left onto Old Town Road. #19 will be on your left. From Stratton, take Winhall Hollow Road to Old Town Road, #19 is on the right.

Public facts

Beds: 5
Baths: 5.5
Sq. Ft.: 6,625
Stories: —
Lot Size: 21.53 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Bennington County
APN: 77124510836

Home facts updated by county records on Jul 15, 2026

Around this home

Schools

Mountain School At Winhall

Private K-8 • 2.1mi

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

7 hot days expected this year, 17 days in 30 years

Wind Factor

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

Air Factor

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

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

$2.37M – $2.87M

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

Nearby similar homes

$875,000

3 beds2 baths1,600 sq ft

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VIDEO TOUR

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72 Benson Fuller Rd, Winhall, VT 05340

$1,250,000

3 beds2.5 baths2,035 sq ft

84 Overlook Rd, East Dorset, VT 05253

$1,399,999

6 beds4 baths3,800 sq ft

121 High Meadow Rd, Winhall, VT 05340-9999

$525,000

3 beds1.5 baths1,594 sq ft

191 Pleasant Street Ext, East Dorset, VT 05253

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

4 beds3 baths2,322 sq ft

72 Benson Fuller Rd, Winhall, VT 05340

Home values near 19 Old Town Rd

Data from public records.

Address	Redfin Estimate
11 Old Town Road, Winhall, VT 3 Beds \| 1 Baths \| 1200 Sq. Ft.	$395,868
14 Old Town Road, Winhall, VT 3 Beds \| 1.5 Baths \| 1144 Sq. Ft.	$388,055

Address	Redfin Estimate
8 Old Town Road, Winhall, VT 1 Beds \| 1 Baths \| 1236 Sq. Ft.	$379,428
24 Old Town Road, Winhall, VT 3 Beds \| 2.5 Baths \| 1955 Sq. Ft.	$656,493

Address	Redfin Estimate
37 Old Town Road, Winhall, VT 3 Beds \| 3 Baths \| 2142 Sq. Ft.	$889,025
17 Old Town Road, Winhall, VT 3 Beds \| 1 Baths \| 918 Sq. Ft.	$364,244

Property information provided by PrimeMLS when last listed in 2025. 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 19 Old Town Rd

Tax history for 19 Old Town 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 19 Old Town Rd

More real estate resources