Last Sold Price
3 beds3,218 sqft$233/sqft
21 Roundtree Rd, Winhall, VT 05340

Description

First time on the market, just minutes from Stratton! One of the only properties currently available in the North Brookwood area. This mountain home offers a well thought out floor plan, open main floor, 2 living areas, 3 bedrooms, 3.5 baths and a bonus room. Positioned up off of the street on an end lot, you have privacy while still having the leisure of resort living. Enjoy winter views while enjoying the warmth of the fireplace after a day out on the slopes! Plenty of room for you and all of your...First time on the market, just minutes from Stratton! One of the only properties currently available in the North Brookwood area. This mountain home offers a well thought out floor plan, open main floor, 2 living areas, 3 bedrooms, 3.5 baths and a bonus room. Positioned up off of the street on an end lot, you have privacy while still having the leisure of resort living. Enjoy winter views while enjoying the warmth of the fireplace after a day out on the slopes! Plenty of room for you and all of your guests to gather! Catch the shuttle to and from Stratton at the end of the driveway on winter weekends and holidays. Easy mountain living awaits! New furnace and on demand hot water installed in 2019. Sports Center bond available with purchase, fee paid for by purchaser.
LISTING CLOSED: 10/18/2021 12:00 AM

  1. Listed by Lauren Behm • Mountain Realty

Sold By Mountain Realty

Property Details for 21 Roundtree Road

Status
MLS #
4883265
Days on Market
6
Taxes
$9,959 / year
HOA Fees
$1,200 / year
Condo/Co-op Fees
-
Property Type
MLS Type
Residential / Single Family
Year Built
2000
Lot Size
1.49 AC / 64,904 SF
Parking
Driveway, Garage, Parking Spaces 5
Zoning
res

Recent comparable sales

Median sold price

$775,000

Avg days on market

39

Sale-to-list ratio

95.4%

Winhall, VT

9 comparable properties found

$795,000 | 5 Founders Hill Road, Winhall, VT 05340
1/27
1

$795,000

Sold 08/21/25

3
Bedrooms
1,624
Square Feet
0.97
Acres
$775,000 | 52 High Meadow Road, Unit 11, Winhall, VT 05340
1/40
2

$775,000

Sold 07/16/26

3
Bedrooms
3,100
Square Feet
Unavailable
Acres
$770,000 | 5 Stratton Ridge Road, Winhall, VT 05340
1/29
3

$770,000

Sold 07/18/25

4
Bedrooms
3,676
Square Feet
1.2
Acres
$950,000 | 154 High Meadow Road, Unit C17, Winhall, VT 05340
1/33
4

$950,000

Sold 12/06/24

4
Bedrooms
3,658
Square Feet
1
Acres
$817,500 | 53 Stratton View Road, Winhall, VT 05340
1/61
5

$817,500

Sold 12/13/24

4
Bedrooms
3,772
Square Feet
2.95
Acres
$630,000 | 5 Linscott Road, Winhall, VT 05340
1/36
6

$630,000

Sold 05/01/26

3
Bedrooms
2,370
Square Feet
1
Acres
$605,000 | 6 Golden Triangle Road, Winhall, VT 05340
1/31
7

$605,000

Sold 10/08/24

3
Bedrooms
2,730
Square Feet
0.81
Acres
$799,000 | 13 Betty Johnson Lane, Winhall, VT 05340
1/38
8

$799,000

Sold 06/26/26

4
Bedrooms
2,797
Square Feet
1.1
Acres
$575,000 | 14 Nearing Road, Winhall, VT 05340
1/2
9

$575,000

Sold 09/12/25

3
Bedrooms
2,064
Square Feet
1.27
Acres

Location

Add your commute

Building Information for 21 Roundtree Road

Stories2Year Built2000Building Size-Lot Size1.49 AC / 64,904 SF

Payment Calculator

$4,742 per month

30 year fixed, 6.55% Interest

Principal and Interest

$3,812

Property Taxes

$830

HOA Dues

$100

The Payment Calculator is for illustrative purposes only.

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Property Information for 21 Roundtree Road

Summary
Location and General Information
  • City: Winhall
  • County: VT-Bennington
  • Directions: Head up the Stratton Mtn Access Road, Right onto North Brookwood, 2nd right in Roundtree Rd, follow to the end, last house on the left.
  • Latitude: 43.119811156293281
  • Longitude: -72.916092915344251
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip: 05340
Taxes and HOA Information
  • Fee: $1,200.00
  • Fee 2 Frequency: Quarterly
  • Fee Frequency: Yearly
  • SPAN Number: 771-245-10416
  • Tax - Gross Amount: $9,959.27
  • Tax Year: 2021
  • Taxes TBD: No
School Information
  • School - High: Choice
  • School - District: Choice
  • School - Elementary: Choice
  • School - Middle/Jr: Choice
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Gravel
Property
Lot Information
  • Lot - Sqft: 64904.0
  • Lot Size Acres: 1.49
  • Road Frontage Length: 60.0
  • Square Feet Apx Finished Above Grade: 1952.0
  • Square Feet Apx Finished AG Source: Assessor
  • Square Feet Apx Finished Below Grade: 1266.0
  • Square Feet Apx Finished BG Source: Assessor
  • Square Feet Apx Total: 3218.0
  • Square Feet Apx Total Finished: 3218.0
  • Square Feet Apx Unfinished Above Grade: 0.0
  • Square Feet Apx Unfinished Below Grade: 0.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Flood Zone: Unknown
  • Foundation: Poured Concrete
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 2000
Utilities
  • Electric Company: GMP
  • Cable Company: Comcast
  • Fuel Company: Suburban
  • Electric: 200 Amp
  • Sewer: Public
  • Utilities: High Speed Intrnt -Avail, Internet - Cable
Interior and Exterior Features
Exterior Features
  • Features - Exterior: Deck, Porch - Covered
  • Roads: Private, Privately Maintained
  • Roof: Shingle - Asphalt
Interior Features
  • Appliances: Dishwasher, Freezer, Microwave, Range - Gas, Refrigerator
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Finished
  • Baths - Total: 4
  • Baths - Full: 2
  • Half Baths: 1
  • One Quarter Baths: 0
  • Three Quarter Bath: 1
  • Rooms - Total: 12
  • Rooms: Level 1: Level 1: Bedroom, Level 1: Bath - Full, Level 1: Bath - 1/2, Level 1: Family Room, Level 1: Foyer, Level 1: Kitchen/Dining
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Bath - 3/4
  • Rooms: Level B: Level B: Bonus Room, Level B: Bath - 3/4, Level B: Living Room
  • Bedrooms - Total: 3
  • Features - Interior: Cathedral Ceiling, Dining Area, Fireplaces - 2, Natural Woodwork, Laundry - Basement
  • Flooring: Carpet, Tile
  • Heat Fuel: Gas - LP/Bottle
  • Heating: Baseboard
  • Cooling: None
  • Total Stories: 2
Room Information
Room 1
  • Room Level: 1
  • Room Type: Bedroom
Room 2
  • Room Level: 2
  • Room Type: Bedroom
Room 3
  • Room Level: 2
  • Room Type: Bedroom
Room 4
  • Room Level: Basement
  • Room Type: Bonus Room
Room 5
  • Room Level: 1
  • Room Type: Bath - 1/2
Room 6
  • Room Level: Basement
  • Room Type: Bath - 3/4
Room 7
  • Room Level: 2
  • Room Type: Bath - 3/4
Room 8
  • Room Level: 1
  • Room Type: Bath - Full
Room 9
  • Room Level: 1
  • Room Type: Family Room
Room 10
  • Room Level: Basement
  • Room Type: Living Room
Room 11
  • Room Level: 1
  • Room Type: Kitchen/Dining
Room 12
  • Room Level: 1
  • Room Type: Foyer

Property History for 21 Roundtree Road

DateEvent & SourcePriceAppreciation
Oct 18, 2021

Sold (Public Record)

Public Record #1476475462

$750,000
Oct 18, 2021

Sold

New England Real Estate Network #4883265

$750,000
Oct 18, 2021

Pending

New England Real Estate Network #4883265

DateEvent & SourcePrice
10/18/2021

Sold (Public Record)

Public Record #1476475462

$750,000
10/18/2021

Sold

New England Real Estate Network #4883265

$750,000
10/18/2021

Pending

New England Real Estate Network #4883265

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 21 Roundtree Road

Taxable ValueLand$179,600Additions$280,200Total$459,800
Tax Record2025$9,614 ($801 / month)
Home Facts
Beds3Baths2Total Finished SqFt1,952 SqFtAbove Grade Finished SqFt1,952 SqFtUnfinished Basement SqFt256 SqFtLot Size64,904 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(245)00430

Schools near 21 Roundtree Road

Rating
School
Type
Grades
Distance
Private - 7 to 12
Private - K to 8
Rating
School
Distance
Stratton Mountain School
Private7 to 12

Mountain School At Winhall
PrivateK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Square Feet
23.5
Acres
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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 21 Roundtree Road, Winhall, VT 05340
$750,000
3
3,218
64,904
$1,130,000
5
4,296
43,995
$625,000
6
5,100
77,536
$550,000
4
2,600
43,995
$135,000
51,836
$897,500
5
4,000
60,984

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Mountain Realty

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 08/21/2026 01:14 AM