Sold
Last Sold Price
4 beds4,330 sqft$85/sqft
21 Deeryard Rd, Winhall, VT 05340
Single FamilyProperty Type
5 acresLot Size
1986Year Built
$85/sq ftPrice per sq ft
2 carsParking Spaces

Description

Located on 5 private acres with views of Stratton Mountain, this spacious home is perfect for enjoying family and friends with large open floor plan and 4 bedrooms and 4 bathrooms. The original owners thought of everything when building their home: living room with wood burning fireplace and cathedral ceiling; ground floor family room; den with gas fireplace and bar; office, screened in porch, whole house generator, wood storage, plenty of great closets, 2 car heated garage, large deck perfect for...Located on 5 private acres with views of Stratton Mountain, this spacious home is perfect for enjoying family and friends with large open floor plan and 4 bedrooms and 4 bathrooms. The original owners thought of everything when building their home: living room with wood burning fireplace and cathedral ceiling; ground floor family room; den with gas fireplace and bar; office, screened in porch, whole house generator, wood storage, plenty of great closets, 2 car heated garage, large deck perfect for barbeques & beautiful landscaping. Enjoy skiing, golf, fishing,hiking, biking and Manchester shopping - all minutes away! Full time residents will appreciate Winhall's school choice.

    Sold By Four Seasons Sotheby's Int'l Realty

    • Listed by: Robin Apps • Four Seasons Sotheby's Int'l Realty
    Listing closed: 11/03/2016 12:00 AM • Source: New England Real Estate Network, MLS#: 4237066

    Recent comparable sales

    Median sold price

    $1,270,000

    Avg days on market

    183

    Sale-to-list ratio

    92.0%

    Winhall, VT

    9 comparable properties found

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

    $817,500

    Sold 12/13/24

    4
    Bedrooms
    3,772
    Square Feet
    2.95
    Acres
    $2,150,000 | 16 Hunter Ridge Road, Winhall, VT 05340
    1/56
    2

    $2,150,000

    Sold 02/12/26

    4
    Bedrooms
    5,000
    Square Feet
    2.66
    Acres
    $1,600,113 | 264 French Hollow Road, Winhall, VT 05340
    1/2
    3

    $1,600,113

    Sold 05/22/26

    4
    Bedrooms
    2,813
    Square Feet
    10.54
    Acres
    $1,300,000 | 33 Jamie Lane, Winhall, VT 05340
    1/52
    4

    $1,300,000

    Sold 08/25/25

    4
    Bedrooms
    4,541
    Square Feet
    11.96
    Acres
    $945,000 | 520 Moose Hollow Road, Winhall, VT 05340
    1/56
    5

    $945,000

    Sold 06/05/26

    4
    Bedrooms
    4,184
    Square Feet
    0.98
    Acres
    $1,665,000 | 14 Old Ridge Road, Winhall, VT 05340
    1/41
    6

    $1,665,000

    Sold 03/09/26

    4
    Bedrooms
    4,270
    Square Feet
    1
    Acres
    $895,000 | 73 Cranberry Hill Road, Winhall, VT 05340
    1/32
    7

    $895,000

    Sold 12/12/25

    4
    Bedrooms
    2,658
    Square Feet
    1.27
    Acres
    $1,270,000 | 33 Forest Haunts Road, Winhall, VT 05343
    1/47
    8

    $1,270,000

    Sold 03/20/26

    4
    Bedrooms
    4,640
    Square Feet
    20.8
    Acres
    $950,000 | 154 High Meadow Road, Unit C17, Winhall, VT 05340
    1/33
    9

    $950,000

    Sold 12/06/24

    4
    Bedrooms
    3,658
    Square Feet
    1
    Acres

    Location

    Add your commute

    Payment Calculator

    $2,782 per month

    30 year fixed, 6.55% Interest

    Principal and Interest

    $1,881

    Property Taxes

    $901

    HOA Dues

    $0

    The Payment Calculator is for illustrative purposes only.

    Know your buying power with a preapproval and custom rate in minutes

    Rocket Mortgage1

    Property Information for 21 Deeryard Road

    Property Details
    • Taxes: $10,817 / year
    • MLS Type: Residential / Single Family
    • Zoning: 5 acre res
    Building Information
    • Stories: 3
    • Year Built: 1986
    • Lot Size: 5.00 AC / 217,800 SF
    Summary
    Location and General Information
    • City: Winhall
    • County: VT-Bennington
    • Directions: From Bondville, to Winhall Hollow Road to French Hollow, to Deeryard. 21 Deeryard is on the left.
    • Latitude: 43.181371
    • Longitude: -72.889961
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Map: 08
    • Zip: 05340
    Taxes and HOA Information
    • SPAN Number: 77124511137
    • Tax - Gross Amount: $10,816.91
    • Tax Year: 2015
    • Tax Year Notes: 2015
    • Taxes TBD: No
    School Information
    • School - High: Choice
    • School - Elementary: Choice
    • School - Middle/Jr: Choice
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Gravel
    Property
    Lot Information
    • Lot: 0136
    • Lot - Sqft: 217800.0
    • Lot Size Acres: 5.0
    • Road Frontage Length: 223.0
    • Square Feet Apx Finished Above Grade: 2766.0
    • Square Feet Apx Finished AG Source: Other
    • Square Feet Apx Finished Below Grade: 1564.0
    • Square Feet Apx Finished BG Source: Other
    • Square Feet Apx Total: 4330.0
    • Square Feet Apx Tot Below Grade: 0.0
    • Square Feet Apx Total Finished: 4330.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished Below Grade: 0.0
    • Square Feet Apx Unfinished BG Source: Other
    Property and Assessments
    • Current Use: No
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete
    • PreConstruction: No
    • Surveyed: Yes
    • Year Built: 1986
    Utilities
    • Electric Company: cvps
    • Electric: 220 Plug
    • Sewer: Concrete, Leach Field, Septic
    • Utilities: Satellite Internet
    Interior and Exterior Features
    Exterior Features
    • Color: Beige
    • Features - Accessibility: 1st Floor Bedroom
    • Features - Exterior: Balcony, Deck, Porch - Covered, Porch - Enclosed, Porch - Screened, Window Screens
    • Roads: Gravel
    • Roof: Shingle - Asphalt
    Interior Features
    • Appliances: Dishwasher, Disposal, Dryer, Microwave, Range - Electric, Refrigerator, Washer
    • Basement: Yes
    • Basement Access Type: Walkout
    • Basement Description: Finished
    • Baths - Total: 4
    • Baths - Full: 3
    • Half Baths: 0
    • One Quarter Baths: 0
    • Three Quarter Bath: 1
    • Rooms - Total: 10
    • Rooms: Level 1: Level 1: Bedroom, Level 1: Family Room, Level 1: Office/Study
    • Rooms: Level 2: Level 2: Bedroom, Level 2: Den, Level 2: Dining Room, Level 2: Kitchen, Level 2: Living Room, Level 2: Master Bedroom
    • Rooms: Level 3: Level 3: Bedroom
    • Bedrooms - Total: 4
    • Equipment: Satellite, Satellite Dish, Security System, Smoke Detector, Smoke Detectr-Batt Powrd
    • Features - Interior: Blinds, Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace - Gas, Fireplace - Wood, Fireplaces - 2, Furnished, Living/Dining, Master BR w/ BA, Skylight, Whirlpool Tub, Window Treatment, Laundry - 1st Floor
    • Flooring: Carpet, Ceramic Tile, Hardwood, Tile
    • Heat Fuel: Oil
    • Heating: Baseboard, Multi Zone, Stove, Stove - Gas, Stove - Wood
    • Cooling: Multi Zone
    • Total Stories: 3
    Room Information
    Room 1
    • Room Dimensions: 12.7 X 13.9
    • Room Level: 2
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 15.5 X 11
    • Room Level: 2
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 17 X 19
    • Room Level: 2
    • Room Type: Living Room
    Room 4
    • Room Dimensions: 19.2 X 17.6
    • Room Level: 1
    • Room Type: Family Room
    Room 5
    • Room Dimensions: 20 X 12.4
    • Room Level: 1
    • Room Type: Office/Study
    Room 7
    • Room Dimensions: 21.10 X 22
    • Room Level: 2
    • Room Type: Master Bedroom
    Room 8
    • Room Dimensions: 13 X 13.7
    • Room Level: 2
    • Room Type: Bedroom
    Room 9
    • Room Dimensions: 13.8 X 14.8
    • Room Level: 3
    • Room Type: Bedroom
    Room 10
    • Room Dimensions: 16 X 13.1
    • Room Level: 1
    • Room Type: Bedroom
    Room 12
    • Room Dimensions: 22.6 X 15
    • Room Level: 2
    • Room Type: Den
    Room 13
    • Room Dimensions: 13.7 X 11.6
    Room 14
    • Room Dimensions: 16.7 X 19.3

    Property History for 21 Deeryard Road

    DateEvent & SourcePriceAppreciation
    Nov 16, 2016

    Sold (Public Record)

    Public Record #593667246

    $370,000
    Nov 3, 2016

    Sold

    New England Real Estate Network #4237066

    $370,000
    Nov 2, 2016

    Pending

    New England Real Estate Network #4237066

    DateEvent & SourcePrice
    11/16/2016

    Sold (Public Record)

    Public Record #593667246

    $370,000
    11/03/2016

    Sold

    New England Real Estate Network #4237066

    $370,000
    11/02/2016

    Pending

    New England Real Estate Network #4237066

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

    Public Records for 21 Deeryard Road

    Taxable ValueLand$285,300Additions$289,800Total$575,100
    Tax Record2025$12,025 ($1,002 / month)
    Home Facts
    Beds3Baths2Total Finished SqFt2,766 SqFtAbove Grade Finished SqFt2,766 SqFtUnfinished Basement SqFt660 SqFtLot Size671,695 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(245)00849

    Schools near 21 Deeryard Road

    Rating
    School
    Type
    Grades
    Distance
    Private - K to 8
    Rating
    School
    Distance
    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.

    Similar Homes

    New listings in 05340

    $910,000 | 7 Roundtree Road, Winhall, VT 05340
    1/41

    $910,000

    4
    Bedrooms
    3,031
    Square Feet
    1.37
    Acres
    $899,000 | E1 Rock Ridge Road, Winhall, VT 05340
    1/41

    $899,000

    4
    Bedrooms
    3,252
    Square Feet
    $2,399,000 | 33 Stone Lodge Road, Winhall, VT 05340
    1/58
    Virtual Tour

    $2,399,000

    4
    Bedrooms
    4,536
    Square Feet
    2.5
    Acres
    $949,000 | 41-43 Cranberry Hill Road, Winhall, VT 05340
    1/58

    $949,000

    4
    Bedrooms
    5,248
    Square Feet
    2
    Acres
    $609,000 | 60 Hilltop Road, Unit 60, Winhall, VT 05340
    1/27
    Virtual Tour

    $609,000

    4
    Bedrooms
    1,650
    Square Feet
    $1,399,999 | 121 High Meadow Road, Winhall, VT 05340
    1/33

    $1,399,999

    6
    Bedrooms
    3,800
    Square Feet
    1
    Acres
    $649,000 | 39 Pond View Road, Unit 39, Winhall, VT 05340
    1/33
    Active Under Contract

    $649,000

    3
    Bedrooms
    1,650
    Square Feet
    $1,200,000 | 109 Winhall Hollow Road, Winhall, VT 05340
    1/31
    Virtual Tour

    $1,200,000

    Unavailable
    Bedrooms
    950
    Square Feet
    23.5
    Acres
    $720,000 | B2 Maple Ridge Road, Winhall, VT 05340
    1/40
    Active Under Contract

    $720,000

    4
    Bedrooms
    2,317
    Square Feet

    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 21 Deeryard Road, Winhall, VT 05340
    $370,000
    4
    4,330
    217,800
    $1,800,000
    4
    4
    4,144
    1,137,352
    3
    3
    2,250
    274,864
    $400,000
    4
    3,245
    229,561
    $1,050,000
    3
    2,849
    217,800
    $540,000
    3
    2,241
    307,098

    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 Four Seasons Sotheby's Int'l 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 09/03/2026 12:57 PM