21 Roundtree Road

Closed 10/18/21
Closed 10/18/21
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Closed
Last Sold Price
$750,000
3 beds3,218 sqft

21 Roundtree Rd, Winhall, VT 05340

Single FamilyProperty Type
1.49 acresLot Size
2000Year Built
$233/sq ftPrice per sq ft
$1,200/yrHOA Fees
2 carsParking Spaces

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.

    Sold By Mountain Realty

    • Listed by: Lauren Behm • Mountain Realty
    Listing closed: 10/18/2021 12:00 AM • Source: New England Real Estate Network, MLS#: 4883265
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    Recent comparable sales

    Median sold price

    $775,000

    Avg days on market

    41

    Sale-to-list ratio

    95.2%

    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

    5 Founders Hill Road, Winhall, VT 05340

    $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

    52 High Meadow Road, Unit 11, Winhall, VT 05340

    $725,000 | 12 Stratton Ridge Road, Winhall, VT 05340
    1/39
    3

    $725,000

    Sold 10/02/26

    4
    Bedrooms
    3,520
    Square Feet
    2.39
    Acres

    12 Stratton Ridge Road, Winhall, VT 05340

    $770,000 | 5 Stratton Ridge Road, Winhall, VT 05340
    1/29
    4

    $770,000

    Sold 07/18/25

    4
    Bedrooms
    3,676
    Square Feet
    1.2
    Acres

    5 Stratton Ridge Road, Winhall, VT 05340

    $950,000 | 154 High Meadow Road, Unit C17, Winhall, VT 05340
    1/33
    5

    $950,000

    Sold 12/06/24

    4
    Bedrooms
    3,658
    Square Feet
    1
    Acres

    154 High Meadow Road, Unit C17, Winhall, VT 05340

    $785,000 | 32 Benson Fuller Drive, Winhall, VT 05340
    1/33
    6

    $785,000

    Sold 09/29/26

    4
    Bedrooms
    2,878
    Square Feet
    1
    Acres

    32 Benson Fuller Drive, Winhall, VT 05340

    $750,000 | 12 Jamie Lane, Winhall, VT 05340
    1/30
    7

    $750,000

    Sold 05/12/25

    4
    Bedrooms
    3,084
    Square Feet
    1
    Acres

    12 Jamie Lane, Winhall, VT 05340

    $817,500 | 53 Stratton View Road, Winhall, VT 05340
    1/61
    8

    $817,500

    Sold 12/13/24

    4
    Bedrooms
    3,772
    Square Feet
    2.95
    Acres

    53 Stratton View Road, Winhall, VT 05340

    $630,000 | 5 Linscott Road, Winhall, VT 05340
    1/36
    9

    $630,000

    Sold 05/01/26

    3
    Bedrooms
    2,370
    Square Feet
    1
    Acres

    5 Linscott Road, Winhall, VT 05340

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    $4,934 per month

    30 year fixed, 7.03% Interest

    Principal and Interest

    $4,004

    Property Taxes

    $830

    HOA Dues

    $100

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    Property Information for 21 Roundtree Road

    Property Details

    • Taxes: $9,959 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Parking: Driveway, Garage, Parking Spaces 5
    • Zoning: res

    Building Information

    • Stories: 2
    • Year Built: 2000
    • Lot Size: 1.49 AC / 64,904 SF

    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 Value

    Land

    $179,600

    Additions

    $280,200
    Total$459,800

    Tax Record

    2025

    $9,614 ($801 / month)

    Home Facts

    Beds

    3

    Baths

    2

    Total Finished SqFt

    3,218 SqFt

    Above Grade Finished SqFt

    1,952 SqFt

    Finished Basement SqFt

    1,266 SqFt

    Unfinished Basement SqFt

    256 SqFt

    Lot Size

    64,904 SqFt

    Style

    Single Family Residence

    County

    BENNINGTON

    APN

    (245)00430

    Schools near 21 Roundtree Road

    Rating
    School
    Type
    Grades
    Distance
    Stratton Mountain School
    		Private - 6 to 12
    Mountain School At Winhall
    		Private - K to 8
    Rating
    School
    Distance
    Stratton Mountain School
    Private6 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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    Nearby home values

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

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    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 11/03/2026 08:52 AM