886 Upper Hollow Road

Closed 1/31/14
Closed 1/31/14
Gallery Image 1
Last Sold Price
$955,000
5 beds3,632 sqft$263/sqft
886 Upper Hollow Rd, Dorset, VT 05251

Description

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...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!
LISTING CLOSED: 01/31/2014 12:00 AM

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

Sold By Josiah Allen Real Estate, Inc.

Property Details for 886 Upper Hollow Road

Status
Closed
MLS #
4255839
Days on Market
103
Taxes
$12,439 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential / Single Family
Year Built
1976
Lot Size
10.96 AC / 477,417 SF
County
Bennington County
Parking
Driveway, Parking Spaces 3
Zoning
residential

Recent comparable sales

Median sold price

$1,075,000

Avg days on market

78

Sale-to-list ratio

94.2%

Dorset, VT

9 comparable properties found

$1,390,000 | 92 Barrows Heights, Dorset, VT 05251
1/46
1

$1,390,000

Sold 08/20/25

5
Bedrooms
3,165
Square Feet
3.89
Acres

92 Barrows Heights, Dorset, VT 05251

$939,000 | 3478 Highway 30, Dorset, VT 05251
1/40
2

$939,000

Sold 10/11/24

5
Bedrooms
4,452
Square Feet
0.45
Acres

3478 Highway 30, Dorset, VT 05251

$1,500,000 | 59 Church Street, Dorset, VT 05251
1/41
3

$1,500,000

Sold 10/01/25

5
Bedrooms
3,436
Square Feet
0.45
Acres

59 Church Street, Dorset, VT 05251

$1,075,000 | 5173 Highway 30, Dorset, VT 05251
1/45
4

$1,075,000

Sold 07/17/26

4
Bedrooms
3,584
Square Feet
0.85
Acres

5173 Highway 30, Dorset, VT 05251

$897,000 | 3444 Highway 30, Dorset, VT 05251
1/28
5

$897,000

Sold 09/12/24

4
Bedrooms
3,082
Square Feet
0.62
Acres

3444 Highway 30, Dorset, VT 05251

$1,250,000 | 7 Timberbrook North, Dorset, VT 05251
1/38
6

$1,250,000

Sold 11/21/25

5
Bedrooms
4,686
Square Feet
4.7
Acres

7 Timberbrook North, Dorset, VT 05251

$650,000 | 364 Barrows Heights, Dorset, VT 05251
1/35
7

$650,000

Sold 10/07/24

4
Bedrooms
4,228
Square Feet
3.2
Acres

364 Barrows Heights, Dorset, VT 05251

$3,025,000 | 73 Pine Road, Dorset, VT 05251
1/49
8

$3,025,000

Sold 08/08/25

6
Bedrooms
3,250
Square Feet
6.21
Acres

73 Pine Road, Dorset, VT 05251

$776,000 | 267 Eagle Ridge, Dorset, VT 05251
1/15
9

$776,000

Sold 08/04/26

4
Bedrooms
4,282
Square Feet
5.92
Acres

267 Eagle Ridge, Dorset, VT 05251

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Building Information for 886 Upper Hollow Road

Stories2Year Built1976Building Size-Lot Size10.96 AC / 477,417 SF

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$5,891 per month

30 year fixed, 6.55% Interest

Principal and Interest

$4,854

Property Taxes

$1,037

HOA Dues

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Property Information for 886 Upper Hollow Road

Summary
Location and General Information
  • City: Dorset
  • County: VT-Bennington
  • Directions: Upper Hollow Road to 886 on your right
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05152
Taxes and HOA Information
  • SPAN Number: 180-057010014
  • Tax - Gross Amount: $12,438.56
  • Tax Year: 2012
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Gravel
Property
Lot Information
  • Lot - Sqft: 477418.0
  • Lot Size Acres: 10.96
  • Road Frontage Length: 840.0
  • Square Feet Apx Finished Above Grade: 3632.0
  • Square Feet Apx Finished Below Grade: 0.0
  • Square Feet Apx Total: 3632.0
  • Square Feet Apx Tot Below Grade: 0.0
  • Square Feet Apx Total Finished: 3632.0
Property and Assessments
  • Current Use: No
  • Property Class: Residential
  • Property Type: Single Family
  • Flood Zone: No
  • Foundation: Concrete
  • Surveyed: Yes
  • Year Built: 1976
Utilities
  • Electric: 200 Amp, Circuit Breaker(s)
  • Sewer: Septic
Interior and Exterior Features
Exterior Features
  • Features - Accessibility: 1st Floor 1/2 Bathroom, 1st Floor Bedroom, 1st Floor Full Bathroom, 1st Floor Hrd Surfce Flr, Bathroom w/Tub
  • Features - Exterior: Balcony, Deck, Hot Tub, Pool - In Ground, Porch, Windows - Storm
  • Roads: Public
  • Roof: Shingle - Asphalt
Interior Features
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Partial
  • Baths - Total: 4
  • Baths - Full: 3
  • Half Baths: 1
  • One Quarter Baths: 0
  • Three Quarter Bath: 0
  • Rooms - Total: 10
  • Rooms: Level 1: Level 1: Bedroom, Level 1: Bath - Full, Level 1: Bath - 1/2, Level 1: Den, Level 1: Kitchen, Level 1: Living Room, Level 1: Primary Bedroom, Level 1: Other
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Bath - Full, Level 2: Office/Study
  • Bedrooms - Total: 5
  • Features - Interior: Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace - Gas, Fireplace - Wood, Fireplaces - 3+, Hearth, Hot Tub, Kitchen Island, Primary BR w/ BA, Vaulted Ceiling, Walk-in Closet, Walk-in Pantry, Whirlpool Tub, Laundry - 1st Floor
  • Flooring: Carpet, Ceramic Tile, Hardwood
  • Heat Fuel: Gas - LP/Bottle, Oil
  • Heating: Hot Air
  • Total Stories: 2
Room Information
Room 1
  • Room Dimensions: 20.6 x 11.7
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Dimensions: 13.48 x 17
  • Room Type: Dining Room
Room 3
  • Room Dimensions: 28 x 17.24
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Type: Foyer
Room 5
  • Room Dimensions: 13 x 13
  • Room Level: 2
  • Room Type: Office/Study
Room 7
  • Room Dimensions: 16. 16.6
  • Room Level: 1
  • Room Type: Primary Bedroom
Room 8
  • Room Dimensions: 13.16 x 15.34
  • Room Level: 1
  • Room Type: Bedroom
Room 9
  • Room Dimensions: 12.79 x 9.33
  • Room Level: 1
  • Room Type: Bedroom
Room 10
  • Room Dimensions: 13 x 14..8
  • Room Level: 2
  • Room Type: Bedroom
Room 11
  • Room Dimensions: 9.75 x 9. 18
  • Room Level: 2
  • Room Type: Bedroom
Room 12
  • Room Dimensions: 12 x 14.8
  • Room Level: 1
  • Room Type: Den
Room 13
  • Room Dimensions: 22.6 x 11.32
  • Room Level: 1
  • Room Type: Other
Room 14
  • Room Dimensions: 12 x 8.6
  • Room Level: 1
  • Room Type: Other
Room 15
  • Room Dimensions: 9.24 x 6.37
  • Room Level: 1
  • Room Type: Other
Room 16
  • Room Level: 1
  • Room Type: Bath - Full
Room 17
  • Room Level: 1
  • Room Type: Bath - Full
Room 18
  • Room Level: 2
  • Room Type: Bath - Full
Room 19
  • Room Level: 1
  • Room Type: Bath - 1/2

Property History for 886 Upper Hollow Road

DateEvent & SourcePriceAppreciation
Feb 3, 2014

Sold (Public Record)

Public Record #409532765

$955,000—
Jan 31, 2014

Sold

New England Real Estate Network #4255839

$955,000—
Dec 3, 2013

Pending

New England Real Estate Network #4255839

—
DateEvent & SourcePrice
02/03/2014

Sold (Public Record)

Public Record #409532765

$955,000
01/31/2014

Sold

New England Real Estate Network #4255839

$955,000
12/03/2013

Pending

New England Real Estate Network #4255839

—

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

Public Records for 886 Upper Hollow Road

Taxable ValueLand$573,800Additions$847,800Total$1,421,600
Tax Record2025$15,628 ($1,302 / month)
Home Facts
Beds0Lot Size477,418 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(057)001213

Schools near 886 Upper Hollow Road

This home is within Taconic and Green Regional School District.
Rating
School
Type
Grades
Distance
Dorset Elementary School
Public - PK to 8
Long Trail School
Private - 6 to 12
Rating
School
Distance
Dorset Elementary School
PublicPK to 8

Long Trail School
Private6 to 12

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: 886 Upper Hollow Road, Dorset, VT 05251
$955,000
5
3,632
477,417
1676 Upper Hollow Road, Dorset, VT 05251
$1,500,000
–
–
–
740,520
50 Red Tail Lane, Dorset, VT 05251
$1,100,000
4
5,293
368,953
1284 Upper Hollow Road, Dorset, VT 05251
$1,000,000
4
3,938
1,089,000
61 Dunn Lane, Dorset, VT 05251
$1,150,000
4
6,238
740,520
Lot 7 Red Tail Lane, Dorset, VT 05251
$210,000
–
–
–
1,742,400

Explore Nearby Homes

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 Josiah Allen Real Estate, Inc.

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 08/27/2026 01:28 AM