Listed by Andrew King • Stratton Real Estate.

For sale

$1,325,000

Est. $8,823/mo —

•

3,400

sq ft

11 Round Tree Rd, Winhall, VT 05340

About this home

11 Round Tree Road, Winhall, VT 05340 A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. With 1.83 acres the house has a very private setting in back for the patio, fire pit and hot tub. Unique U-shaped driveway has plenty of room for friends and family. Appropriately sized mud room for all the gear. Downstairs family room with fireplace and kitchenette. Wonderful staircase leading to the second floor. Great open living space and bedrooms throughout including a useful loft with bathroom. Quality metal roof sheds snow easily. A must-see property at Stratton.

Single-familyProperty Type

1983Year Built

1.83 acresLot Size

$390Price/Sq.Ft.

1 car garageParking

Listed by Andrew King • Stratton Real Estate

Listing updated: Aug 30, 2026 at 09:25pm

Redfin checked: 3 minutes ago

•Source:PrimeMLS #5107395

Payment calculator

$8,823 per month

Principal and interest$7,412

Property taxes

$1,202

HOA dues

Home insurance

$210

Utilities

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Open houses

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Nearby open houses (10)

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6 Jamie Ln, Winhall, VT 05340
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5 beds4 baths4,491 sq ft
866 E Manchester Rd, Manchester Center, VT 05255
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$1,200,000
5 beds5 baths5,092 sq ft
2313 Barnumville Rd, Manchester Center, VT 05255
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$1,200,000
6 beds3.5 baths4,017 sq ft
11 Founders Hill Rd, Winhall, VT 05155
OPEN SAT, 1PM TO 3PM
$450,000
4 beds3 baths3,268 sq ft
2855 Thompsonburg Rd, South Londonderry, VT 05155
OPEN SAT, 2PM TO 5PM
$995,000
4 beds3 baths2,614 sq ft
3269 Route 30, Dorset, VT 05251
OPEN SUN, 11AM TO 1PM
$425,000
3 beds2.5 baths1,377 sq ft
34 Sugar Brook Rd Unit F3, Peru, VT 05152
OPEN SUN, 11AM TO 2PMVIDEO TOUR
$1,575,000
3 beds2.5 baths5,296 sq ft
395 Alzac Ln, Wardsboro, VT 05355
OPEN SUN, 12PM TO 2PM3D & VIDEO TOUR
$1,050,000
4 beds4 baths2,380 sq ft
20 W Branch Rd, Winhall, VT 05340

Around this home

Schools

K - 12
Preschool & daycare

Mountain School At Winhall

Private K-8 • 2.4mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

11 Round Tree Rd · $1,325,000

Strong offer

$1.33M and above

75% chance or better to win

Why $1.33M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 72 days.

SALE-TO-LIST

Most homes are selling 3% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
10 total rooms

Bathrooms
3 full bathrooms
1 half bathroom

Heating & cooling
Baseboard heating
Electric heating
Radiant heating

Sale and tax history for 11 Round Tree Rd

Sale History
Tax History

Date

Event

Price

PrimeMLS #5107395

Aug 30, 2026

Listed

$1,325,000

$390/sq ft

PrimeMLS #4227431

Sep 24, 2014

Sold

$515,000

$151/sq ft

Apr 6, 2013

Listed

$595,000

$175/sq ft

Always impressive & solidly built, recent renovations have greatly enhanced this handsome Stratton resort property on a quiet cul de sac with shuttle service. 5 spacious bedrooms, renovated master bath & 2 renovated guest baths all with exquisite tile work & heated floors is only the beginning of what this house offers. The entry level with foyer has heated tile flooring, a family room & remodeled Pullman kitchen, 2 guest bedrooms & bath. The main level kitchen with breakfast bar & living/dining area with stone fireplace rises up to a stunning vaulted wood paneled ceiling. The master bedroom en suite has private access onto a large mahogany back deck with new hot tub overlook a sloping woodland backyard. A guest bedroom with hallway bath completes this level. The 3rd level reveals a loft bedroom en suite with vaulted ceiling & expansive scenic view. A heated oversized windowed one-car garage offers future expansion area. Offered furnished for a turnkey opportunity not to be missed.

Year

Property tax

Land + Additions

Assessment*

2025

$10,768 (−0.8%)

$195,200 + $319,800

$515,000

2024

$10,856 (+18.4%)

$195,200 + $319,800

$515,000

2023

$9,172 (−15.6%)

$195,200 + $319,800

$515,000

2022

$10,861 (−2.6%)

$195,200 + $319,800

$515,000

2021

$11,155

$195,200 + $319,800

$515,000

2020

$11,166 (+5.3%)

$195,200 + $319,800

$515,000

2019

$10,599 (+6.0%)

$195,200 + $319,800

$515,000

2018

$9,995 (−0.7%)

$195,200 + $319,800

$515,000

2017

$10,061 (−4.3%)

$195,200 + $319,800

$515,000

2016

$10,508 (+2.3%)

$195,200 + $319,800

$515,000

2015

$10,268 (+3.4%)

$195,200 + $319,800

$515,000

2014

$9,932

$195,200 + $319,800

$515,000

2013

$195,200 + $319,800

$515,000

Public record

Public record
Zoning

Beds

Baths

Stories

—

Lot width

—

Lot depth

—

Lot size

1.88 Acres

Year renovated

—

Finished Sq. Ft.

2,413

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,413

Year built

1978

Style

Single Family Residential

County

Bennington County

APN

77124511414

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

REC

Recreational District

The Recreational District is established as areas to provide various recreational opportunities for residents and visitors alike, as well as a variety of housing and related commercial uses. Commercial development, where feasible, shall support residential and recreational uses and shall be clearly secondary to the commercial uses in the Bondville Village District.

Permitted uses

Include but are not limited to:

Agriculture
Housing-Single unit
Housing-Senior
Cemetery
Timberland

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 84° expected this year, 19 days in 30 years

3/10 Wind Factor

7% 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

82/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Winhall. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.8 hrs

4.9 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 11 Round Tree Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $643,868 and $1,100,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $644K to $1.1M.

SOLD SEP 29, 2026
$785,000 Last sold price
4 beds3.5 baths2,878 sq ft
32 Benson Fuller Dr, Winhall, VT 05340
$117/sq ft
smaller lot
6 years newer
SOLD AUG 31, 2026
$1,100,000 Last sold price
3 beds4 baths2,745 sq ft
65 Lower Taylor Hill Rd, Winhall, VT 05340
$11/sq ft
larger lot
31 years newer
SOLD NOV 27, 2025
$975,000 Last sold price
5 beds3.5 baths3,500 sq ft
20 Jamie Ln, Winhall, VT 05340
$111/sq ft
smaller lot
4 years newer
SOLD AUG 21, 2026
$643,868 Last sold price
3 beds2 baths2,204 sq ft
11 Stratton View Rd, Winhall, VT 05340
$98/sq ft
smaller lot
14 years older
SOLD OCT 2, 2026
$725,000 Last sold price
4 beds4 baths3,520 sq ft
12 Stratton Ridge Rd, Winhall, VT 05340
$184/sq ft
larger lot
3 years older
SOLD JUN 5, 2026
$1,050,000 Last sold price
3 beds4.5 baths4,279 sq ft
3 Linscott Rd, Winhall, VT 05340
$145/sq ft
smaller lot
5 years newer

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Early Access listings

EARLY ACCESSCOMPASS COMING SOON

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New listings for sale in 05340

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15 Nearing Rd, Winhall, VT 05340

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45 Benson Fuller Dr, Winhall, VT 05340

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Details provided by PrimeMLS and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Offer insights

Property details

Sale and tax history for 11 Round Tree Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 11 Round Tree Rd

Early Access listings

Nearby similar homes

New listings for sale in 05340

More real estate resources