OFF MARKET

Listed by Terry Hill • Berkshire Hathaway HomeServices Stratton Home. Bought with Berkshire Hathaway HomeServices Stratton Home.

Off Market May 2022 for $1.8M

$2,278,599

Est. refi paymentEst. refi $11,410/mo

•

5,000

sq ft

29 Deeryard Rd #21, Winhall, VT 05340

About this home

GREEN ACRES IS THE PLACE TO BE. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. Unprecedented views from this amazing mountain contemporary. BIG Stratton views and beyond await you on 26 rolling acres with all the recreation at your doorstep you can possibly take in, in one day. This gorgeous property is perfect for entertaining your large family or guest gatherings with many common areas inside & out. Attractive stone patios, porches and decks allow you to enjoy the scenic outdoors while almost every interior room boasts magnificent mtn views. Over the years the current owners have renovated, updated & added additional space to accommodate their active lifestyle. The enormous recreation room on the upper level overlooking the back patio is a huge feature you will greatly appreciate. Sleek kitchen w/ granite counter tops, breakfast table & island. Comfortable media room, den with additional fireplace and loft office area add extra living spaces for you & your company. Plenty of sleeping accommodations on multiple levels. Wine cellar is conveniently located below the dining/kitchen. Private screened in porch. Sunken hot tub. Solar panels on the roof. Take a walk up to the upper property & after a vigorous game of tennis on a well maintained court follow the groomed path down to a beautiful, clean swimming pond 9' deep or simply jump in the outdoor shower. Enjoy walking & snowshoeing trails already laid out for you. We can't wait for you to see this extraordinary listing!

Single-familyProperty Type

1980Year Built

26 acresLot Size

$456Est. Price/Sq.Ft.

Listed by Terry Hill • Berkshire Hathaway HomeServices Stratton Home

Bought with Lauren Behm • Berkshire Hathaway HomeServices Stratton Home

Redfin checked: a minute ago

•Source:PrimeMLS #4896195

Redfin Estimate

$2,278,599

$479K since sold in May 2022$45K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 117.1% higher than the average sale price ($1.05M) of 6 comparable homes.

SOLD DEC 15, 2025
$502,500
A
4 beds4 baths2,370 sq ft
377 Glen Rd, Peru, VT 05152
SOLD JUL 27, 2026
$1,287,500
B
4 beds3.5 baths4,153 sq ft
487 Vermont Route 100, South Londonderry, VT 05155
SOLD JUL 17, 2026
$799,000
C
4 beds3.5 baths3,078 sq ft
63 Raspberry Hill Rd, Winhall, VT 05340
SOLD MAY 21, 2026
$1,374,000
D
4 beds3.5 baths5,397 sq ft
12 Sunny Hill Rd, Winhall, VT 05340
SOLD MAY 1, 2026
$735,000
E
4 beds3 baths2,091 sq ft
5 Wall St, Winhall, VT 05340
SOLD MAY 22, 2026
$1,600,113
F
4 beds3.5 baths2,813 sq ft
264 French Hollow Rd, Winhall, VT 05340

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,300/mo

Redfin rental estimate

List your home for rent

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

VIDEO TOUR
$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
See all

Provided by Redfin

Sale history for 29 Deeryard Rd #21

Year

Property tax

Land + Additions

Assessment*

2025

$20,290 (+2.2%)

$359,700 + $744,800

$1,104,500

2024

$19,857 (+0.9%)

$359,700 + $744,800

$1,104,500

2023

$19,671 (+6.6%)

$359,700 + $744,800

$1,104,500

2022

$18,454 (−2.6%)

$359,700 + $515,300

$875,000

2021

$18,953

$359,700 + $515,300

$875,000

2020

$18,971 (+5.3%)

$359,700 + $515,300

$875,000

2019

$18,008 (+6.0%)

$359,700 + $515,300

$875,000

2018

$16,982 (−0.7%)

$359,700 + $515,300

$875,000

2017

$17,094 (−4.3%)

$359,700 + $515,300

$875,000

2016

$17,854 (+2.3%)

$359,700 + $515,300

$875,000

2015

$17,446 (+3.4%)

$359,700 + $515,300

$875,000

2014

$16,874

$359,700 + $515,300

$875,000

2013

$359,700 + $515,300

$875,000

Tax history for 29 Deeryard Rd #21

Year

Property tax

Land + Additions

Assessment*

2025

$20,290 (+2.2%)

$359,700 + $744,800

$1,104,500

2024

$19,857 (+0.9%)

$359,700 + $744,800

$1,104,500

2023

$19,671 (+6.6%)

$359,700 + $744,800

$1,104,500

2022

$18,454 (−2.6%)

$359,700 + $515,300

$875,000

2021

$18,953

$359,700 + $515,300

$875,000

2020

$18,971 (+5.3%)

$359,700 + $515,300

$875,000

2019

$18,008 (+6.0%)

$359,700 + $515,300

$875,000

2018

$16,982 (−0.7%)

$359,700 + $515,300

$875,000

2017

$17,094 (−4.3%)

$359,700 + $515,300

$875,000

2016

$17,854 (+2.3%)

$359,700 + $515,300

$875,000

2015

$17,446 (+3.4%)

$359,700 + $515,300

$875,000

2014

$16,874

$359,700 + $515,300

$875,000

2013

$359,700 + $515,300

$875,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

—

Lot width

—

Lot depth

—

Lot size

26.11 Acres

Year renovated

—

Sq. Ft.

4,144

Year built

1980

Style

Single Family Residential

County

Bennington County

APN

77124511242

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Interior

Virtual Tour

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

Basement Information
Basement: Yes
Basement Access: Interior
Concrete

Other Interior Features
# of Rooms: 15
Level B: Wine Cellar
Flooring: Carpet, Hardwood, Softwood, Tile
Water Heater: Electric
Fireplaces - 2, Kitchen Island, Living/Dining, Master Bedroom With Bath, Walk-in Pantry, Laundry - 1st Floor

Equipment & Appliance Information
Cooktop - Electric, Dishwasher, Dryer, Microwave, Oven - Wall, Refrigerator, Washer
Security System, Smoke Detectr-Battery Powered, Stove-Wood

Room 1 Information
Foyer
Foyer
Dimensions: 11.5 x 11
Level: 1

Room 2 Information
Mudroom
Dimensions: 10 x 7
Level: 1

Room 3 Information
Living Room
Dimensions: 24 x 23
Level: 1

Room 4 Information
Dining Room
Dimensions: 17 x 16
Level: 1

Room 5 Information
Kitchen
Dimensions: 19 x 20
Level: 1

Room 6 Information
Library
Library
Dimensions: 11 x 12.8
Level: 1

Room 7 Information
Den
Dimensions: 13.8 x 18
Level: 1

Room 8 Information
Bedroom
Dimensions: 18.8 x 12.10
Level: 1

Room 9 Information
Rec Room
Dimensions: 21.8 x 35
Level: 2

Room 10 Information
Master Bedroom
Dimensions: 15.5 x 15
Level: 2

Room 11 Information
Loft
Dimensions: 11 x 8
Level: 2

Room 12 Information
Bedroom
Dimensions: 15.3 x 16
Level: 2

Room 13 Information
Bedroom
Dimensions: 19 x 10.10
Level: 3

Room 14 Information
Bedroom
Dimensions: 25 x 15
Level: 3

Room 15 Information
Wine Cellar
Dimensions: 14 x 14
Level: Basement

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 5000
Approximate Sq. Ft. Total: 5000
Color: Tan/Stone
Deck, Garden Space, Hot Tub, Patio, Porch - Covered, Porch - Screened, Tennis Court, Window Screens
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle - Asphalt, Standing Seam
Exterior: Wood Siding

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot: 21 Midlands
Easements: Unknown
Landscaped, Mountain View, Pond, Rolling, Trail/Near Trail, View, Walking Trails, Wooded

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1980
Unit/Lot #: 21
Water Body Access: No

Financial

Tax Information
Tax Year: 2021
Gross Amount Tax: 18952.51
SPAN Number: 771-245-11242

Other Tax Information
Page Deed: 394

Utilities

Heating & Cooling Information
Heat: Baseboard, Electric, Passive Solar
Heat Fuel: Electric, Solar, Wood

Sewer Information
Septic

Electric Information
Electric Company: GMP
200 Amp

Water Information
Drilled Well

Other Utilities Information
Fuel Company: GMP
Internet - Fixed Wireless

Location

School Information
School District: Choice
Elementary School: Choice
Elementary School: Choice
Middle/Jr School: Choice

Road Information
Road Frontage: Yes
Road Frontage Length: 250
Gravel, Public

Other Location Information
Directions: From Winhall/Bondville Village travel Winhall Hollow Rd to French Hollow Road to Deeryard Second to last drive on left

Public facts

Beds: 4
Baths: 4.0
Sq. Ft.: 4,144
Stories: —
Lot Size: 26.11 acres
Style: Single Family Residential
Year Built: 1980
Year Renovated: —
County: Bennington County
APN: 77124511242

Home facts updated by county records on Jul 15, 2026

Around this home

Schools

Some nearby schools may not be within this home's attendance zone. Please check the school district website to verify.

Flood Brook Unified School District #20

Public PreK-8 • 4.6mi

6/10

Mountain School At Winhall

Private K-8 • 2.2mi

Stratton Mountain School

Private 7-12 • 4.7mi

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 days above 87° expected this year, 17 days in 30 years

3/10 Wind Factor

5% 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

In this area, properties receive around 8.3 hours in June and 3.4 hours in December, placing it below the U.S. average for solar exposure.

8.3 hrs

3.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.17M – $2.62M

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

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New listings for sale in 05340

VIDEO TOUR

$599,000

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33 Burnt Hill Rd, Winhall, VT 05340

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2 beds2 baths960 sq ft

19 Winhall Condo Rd #4, Winhall, VT 05340

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4 beds3.5 baths4,536 sq ft

33 Stone Lodge Rd, Winhall, VT 05340

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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

Home values near 29 Deeryard Rd #21

Data from public records.

Address	Redfin Estimate
21 Deeryard Rd, Winhall, VT 4 Beds \| 4 Baths \| 4330 Sq. Ft.	$1,044,857
28 Deeryard Rd, Winhall, VT 3 Beds \| 3 Baths \| 2250 Sq. Ft.	$636,073

Address	Redfin Estimate
18 Deeryard Rd, Winhall, VT 5 Beds \| 3.5 Baths \| 3904 Sq. Ft.	$1,242,192
30 Deeryard Rd, Winhall, VT 2 Beds \| 2 Baths \| 3245 Sq. Ft.	$765,549

Address	Redfin Estimate
10 Deeryard Rd, Winhall, VT 3 Beds \| 3 Baths \| 2241 Sq. Ft.	$978,808
9 Deeryard Rd, Winhall, VT 3 Beds \| 3 Baths \| 2961 Sq. Ft.	$830,476

Property information provided by PrimeMLS when last listed in 2022. 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 29 Deeryard Rd #21

Tax history for 29 Deeryard Rd #21

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 29 Deeryard Rd #21

More real estate resources