Listed by Jill Simon • Josiah Allen Real Estate, Inc. Bought with Josiah Allen Real Estate, Inc.

Off Market Jan 2014 for $955K

$1,765,224

Est. refi paymentEst. refi $6,246/mo

•

3,632

sq ft

886 Upper Hollow Rd, Dorset, VT 05152

About this home

Hidden Jewel- Graciously sited on 11 acres with spectacular views. Pool, hot tub, outdoor shower and large deck with it's own fireplace make this a great place for outdoor entertaining. Expansive open kitchen with many amenities adjoins a dining area with it's own gas fired hearth. Large vaulted living room with floor to ceiling stone fireplace and wet bar make it a great year round space. 5 bedrooms including a master suite with over sized walk-in closet and bath with whirlpool tub. 2 more bedrooms on the main floor that share a bath. Additional 2 bedrooms with another bath upstairs. Great office area and den. Lots of other nooks and crannies. Great storage including a cedar closet. 2 car garage with a 3rd bay for toys, equipment or another car. Beautifully landscaped with many perennials. The land has the possibility of a 3 acre piece that could be a separate parcel to be sold or built on in the future. Special Dorset Hollow panache. Come have a look and be WOWED!

Single-familyProperty Type

1976Year Built

10.96 acresLot Size

$486Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Jill Simon • Josiah Allen Real Estate, Inc.

Bought with Willard Watson • Josiah Allen Real Estate, Inc.

Redfin checked: 2 minutes ago

•Source:PrimeMLS #4255839

Redfin Estimate

$1,765,224

$810K since sold in January 2014$128K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 72.9% higher than the average sale price ($1.02M) of 6 comparable homes.

SOLD JUL 24, 2026
$825,000
A
4 beds3.5 baths3,237 sq ft
1731 Three Maple Dr, Manchester Center, VT 05255
SOLD AUG 4, 2026
$776,000
B
4 beds3.5 baths4,282 sq ft
267 Eagle Rdg, Dorset, VT 05251
SOLD JUL 17, 2026
$1,075,000
C
4 beds4.5 baths3,584 sq ft
5173 Route 30, Dorset, VT 05251
SOLD JUN 15, 2026
$650,000
D
4 beds4 baths3,161 sq ft
413 Dutch Hill Rd, Danby, VT 05739
SOLD JUL 31, 2026
$1,700,000
E
5 beds4.5 baths3,218 sq ft
5491 VT Route 315, Rupert, VT 05776
SOLD AUG 13, 2026
$1,100,000
F
3 beds3 baths2,797 sq ft
227 Birchstone Ln, East Dorset, VT 05253

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Earn from this home

Refinance

Est. cash available

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Market trends in 05251, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

99.2%

+0.9% MoM

Median sale price

$776K

$92K MoM

Avg. days on market

47d

16 days MoM

Recently sold homes

0 MoM

Provided by Redfin

Sale history for 886 Upper Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$15,628 (−4.7%)

$573,800 + $847,800

$1,421,600

2024

$16,400 (+14.3%)

$330,960 + $505,680

$836,640

2023

$14,342 (−11.7%)

$330,960 + $505,680

$836,640

2022

$16,243 (+2.8%)

$330,960 + $505,680

$836,640

2021

$15,803 (+1.6%)

$330,960 + $505,680

$836,640

2020

$15,552 (+5.6%)

$330,960 + $505,680

$836,640

2019

$14,725 (+0.6%)

$330,960 + $505,680

$836,640

2018

$14,637 (+1.2%)

$330,960 + $505,680

$836,640

2017

$14,466 (+1.7%)

$330,960 + $505,680

$836,640

2016

$14,228 (+3.3%)

$330,960 + $505,680

$836,640

2015

$13,772

$330,960 + $505,680

$836,640

2013

Tax history for 886 Upper Hollow Rd

Year

Property tax

Land + Additions

Assessment*

2025

$15,628 (−4.7%)

$573,800 + $847,800

$1,421,600

2024

$16,400 (+14.3%)

$330,960 + $505,680

$836,640

2023

$14,342 (−11.7%)

$330,960 + $505,680

$836,640

2022

$16,243 (+2.8%)

$330,960 + $505,680

$836,640

2021

$15,803 (+1.6%)

$330,960 + $505,680

$836,640

2020

$15,552 (+5.6%)

$330,960 + $505,680

$836,640

2019

$14,725 (+0.6%)

$330,960 + $505,680

$836,640

2018

$14,637 (+1.2%)

$330,960 + $505,680

$836,640

2017

$14,466 (+1.7%)

$330,960 + $505,680

$836,640

2016

$14,228 (+3.3%)

$330,960 + $505,680

$836,640

2015

$13,772

$330,960 + $505,680

$836,640

2013

*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

10.96 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Bennington County

APN

18005710014

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 2
Location: Attached
Driveway, Parking Spaces 3

Interior

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

Basement Information
Basement: Yes
Basement Access: Interior
Partial

Other Interior Features
# of Rooms: 10
Flooring: Carpet, Ceramic Tile, Hardwood
Water Heater: Domestic
Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace - Gas, Fireplace - Wood, Fireplaces - 3+, Hearth, Hot Tub, Kitchen Island, Master Bedroom With Bath, Vaulted Ceiling, Walk-in Closet, Walk-in Pantry, Whirlpool Tub, Laundry - 1st Floor

Accessibility Information
1st Floor 1/2 Bathroom, 1st Floor Bedroom, 1st Floor Full Bathroom, 1st Floor Hrd Surfce Flor, Bathroom w/Tub

Room 1 Information
Kitchen
Kitchen
Dimensions: 20.6 x 11.7
Level: 1

Room 2 Information
Dining Room
Dimensions: 13.48 x 17

Room 3 Information
Living Room
Dimensions: 28 x 17.24
Level: 1

Room 4 Information
Foyer

Room 5 Information
Office/Study
Dimensions: 13 x 13
Level: 2

Room 7 Information
Master Bedroom
Dimensions: 16. 16.6
Level: 1

Room 8 Information
Bedroom
Dimensions: 13.16 x 15.34
Level: 1

Room 9 Information
Bedroom
Dimensions: 12.79 x 9.33
Level: 1

Room 10 Information
Bedroom
Dimensions: 13 x 14..8
Level: 2

Room 11 Information
Bedroom
Dimensions: 9.75 x 9. 18
Level: 2

Room 12 Information
Den
Dimensions: 12 x 14.8
Level: 1

Room 13 Information
Other
Dimensions: 22.6 x 11.32
Level: 1

Room 14 Information
Other
Dimensions: 12 x 8.6
Level: 1

Room 15 Information
Other
Dimensions: 9.24 x 6.37
Level: 1

Room 16 Information
Full Bath
Level: 1

Room 17 Information
Full Bath
Level: 1

Room 18 Information
Full Bath
Level: 2

Room 19 Information
1/2 Bath
Level: 1

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 3632
Approximate Sq. Ft. Total: 3632
Balcony, Deck, Hot Tub, Pool - In Ground, Porch, Windows - Storm
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle - Asphalt
Exterior: Shingle, Wood

Driveway
Gravel

Lot, Zoning, & Easement Information
Country Setting, Landscaped, Mountain View

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1976

Financial

Tax Information
Tax Year: 2012
Gross Amount Tax: 12438.56
SPAN Number: 180-057010014

Other Tax Information
Page Deed: 69

Utilities

Heating & Cooling Information
Heat: Hot Air
Heat Fuel: Gas - Liquid Propane Bottle, Oil

Sewer Information
Septic

Electric Information
200 Amp, Circuit Breaker(s)

Water Information
Drilled Well

Location

Road Information
Road Frontage: Yes
Road Frontage Length: 840
Public

Other Location Information
Directions: Upper Hollow Road to 886 on your right

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 10.96 acres
Style: Other
Year Built: —
Year Renovated: —
County: Bennington County
APN: 18005710014

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 Taconic and Green Regional School District website to verify.

Dorset Elementary School

Public PreK-8 • 3.0mi

6/10

Long Trail School

Private 6-12 • 1.6mi

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 88° expected this year, 16 days in 30 years

3/10 Wind Factor

6% 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

Dorset, VT • 05152

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$1.68M – $2.03M

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

Nearby similar homes

$595,000

4 beds3 baths3,272 sq ft

1174 N Main St, Danby, VT 05739

$515,000

3 beds2 baths1,528 sq ft

335 Tinmouth Rd, Danby, VT 05739

$599,000

4 beds3 baths2,886 sq ft

209 Kelley Hill Rd, Danby, VT 05739

$925,000

3 beds2 baths2,403 sq ft

99 Holly's Way, West Rupert, VT 05776

$390,000

4 beds2 baths2,352 sq ft

85 Depot Street Ext, Mount Tabor, VT 05739

$565,000

4 beds2.5 baths2,399 sq ft

1131 Route 30, Dorset, VT 05251

Home values near 886 Upper Hollow Rd

Data from public records.

Address	Redfin Estimate
444 Upper Hollow Rd, Dorset, VT 4 Beds \| 3.5 Baths \| 2864 Sq. Ft.	$2,179,664
1060 Upper Hollow Rd, Dorset, VT 5 Beds \| 5.5 Baths \| 4674 Sq. Ft.	$5,010,567

Address	Redfin Estimate
427 Upper Hollow Rd, Dorset, VT 4 Beds \| 5 Baths \| 4799 Sq. Ft.	$1,822,240
1284 Upper Hollow Rd, Dorset, VT 4 Beds \| 3.5 Baths \| 3938 Sq. Ft.	$1,970,037

Address	Redfin Estimate
1284 Upper Hollow Rd, Dorset, VT 2 Beds \| 1 Baths \| 1085 Sq. Ft.	$887,770
511 Upper Hollow Rd, Dorset, VT 5 Beds \| 5 Baths \| 4306 Sq. Ft.	$2,230,904

Property information provided by PrimeMLS when last listed in 2013. This data may not match . Learn more.

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