362 Upper Rd

Bridgewater, VT 05035

$700,000
Last Sold Price
13
Beds
6,246 Sq. Ft.
$112 / Sq. Ft.
6,246
Sq. Ft.
$112
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Closed 8/27/21
Closed 8/27/21

Description

Perfectly suited for either residential or commercial use, this unique property is anchored around an antique cape farmhouse built when the township was founded. In an exceptional location, close to both the historic village of Woodstock and Killington Mountain Ski Resort, and within walking distance of the Long Trail Brewpub and the Bridgewater Corners Country Store; the beautifully landscaped four acre grounds feature an in-ground swimming pool with sheltered deck overlooking the Ottaquechee River...Perfectly suited for either residential or commercial use, this unique property is anchored around an antique cape farmhouse built when the township was founded. In an exceptional location, close to both the historic village of Woodstock and Killington Mountain Ski Resort, and within walking distance of the Long Trail Brewpub and the Bridgewater Corners Country Store; the beautifully landscaped four acre grounds feature an in-ground swimming pool with sheltered deck overlooking the Ottaquechee River Valley. The spacious, sunny, 6,200 square feet of living space is arranged into two sections connected by an enormous commercial grade kitchen. The larger section, continuously and profitably operated as October Country Inn since 1975, has 10 bedrooms, 11 baths, two large dining/meeting /game rooms, and a spacious living room. The other section, used as the innkeepers residence, has 3 bedrooms, 1 bath, office and private living area. A large semi-finished basement houses a commercial sized pantry, laundry area, large workshop and general storage. This property could easily be used as a private home for extended family, with room to grow into a special and affordable multi-generational family compound, or continued as a turn-key opportunity to step in and take over October Country Inn's long standing, excellent four decades long reputation for outstanding hospitality to the traveling public in the tradition of New England's country inns dating back over 200 years.
  1. Listed by Laird Bradley • Williamson Group Sothebys Intl. Realty

Sold By Williamson Group Sothebys Intl. Realty

Property Details for 362 Upper Road

Parking
Parking Spaces 11 - 20
Zoning
NONE
LISTING CLOSED: 08/27/2021 12:00 AM

Property Details for 362 Upper Road

StatusClosed
MLS #4741360
Days on Market796
Taxes$8,782 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1820
Lot Size4.00 AC / 174,240 SF
CountyWindsor County
Get preapproved with Rocket Mortgage1

Location

Add your commute

Building Information for 362 Upper Road

Stories1Year Built1820Building Size-Lot Size4.00 AC / 174,240 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$4,220 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,488

Property Taxes

$732

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 362 Upper Road

Summary
Location and General Information
  • City: Bridgewater
  • County: VT-Windsor
  • Directions: US ROUTE 4 WEST 5 MILES FROM THE VILLAGE OF WOODSTOCK TOWARDS KILLINGTON SKI AREA. TAKE RIGHT ON UPPER ROAD 100 YARDS BEFORE INTERSECTION OF ROUTE 4 AND ROUTE 100A (TO COOLIDGE PRESIDENTIAL HOMESTEAD). TRAVEL 1/4 MILE TO OCTOBER COUNTRY INN ON RIGHT.
  • Latitude: 43.589495916498102
  • Longitude: -72.657619949737523
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Map: 06.112
  • Zip: 05035
Taxes and HOA Information
  • SPAN Number: 084-026-10536
  • Tax - Gross Amount: $8,782.25
  • Tax Year: 2019
  • Taxes TBD: No
School Information
  • School - High: Woodstock Senior UHSD #4
  • School - District: Windsor Central
  • School - Elementary: Woodstock Elementary School
  • School - Middle/Jr: Woodstock Union Middle Sch
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Crushed Stone
Property
Lot Information
  • Lot - Sqft: 174240.0
  • Lot Size Acres: 4.0
  • Road Frontage Length: 200.0
  • Square Feet Apx Finished Above Grade: 6246.0
  • Square Feet Apx Finished AG Source: Public Records
  • Square Feet Apx Finished Below Grade: 0.0
  • Square Feet Apx Finished BG Source: Public Records
  • Square Feet Apx Total: 8493.0
  • Square Feet Apx Total Finished: 6246.0
  • Square Feet Apx Unfinished Above Grade: 0.0
  • Square Feet Apx Unfinished AG Source: Public Records
  • Square Feet Apx Unfinished Below Grade: 2247.0
  • Square Feet Apx Unfinished BG Source: Public Records
Property and Assessments
  • Current Use: No
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • Foundation: Concrete, Fieldstone
  • PreConstruction: No
  • Suitable Use: Bed and Breakfast, Commercial, Recreation, Residential
  • Surveyed: Yes
  • Year Built: 1820
Utilities
  • Electric: 200 Amp
  • Sewer: 1500+ Gallon, Leach Field, Leach Field - Conventionl, Leach Field - Existing
  • Utilities: Cable - At Site
Interior and Exterior Features
Exterior Features
  • Roads: Gravel, Public
  • Roof: Standing Seam
Interior Features
  • Appliances: Dishwasher, Dryer, Exhaust Hood, Freezer, Microwave, Mini Fridge, Oven - Double, Range - Gas, Refrigerator, Washer
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Climate Controlled, Concrete Floor, Crawl Space, Full, Storage Space, Interior Access, Exterior Access
  • Baths - Total: 11
  • Baths - Full: 7
  • Half Baths: 0
  • One Quarter Baths: 0
  • Three Quarter Bath: 4
  • Rooms - Total: 19
  • Bedrooms - Total: 13
  • Heat Fuel: Oil
  • Heating: Baseboard, Hot Water, Multi Zone
  • Cooling: Other
  • Total Stories: 1.75

Property History for 362 Upper Road

DateEvent & SourcePriceAppreciation
Aug 27, 2021

Sold

New England Real Estate Network #4741360

$700,000—
Aug 2, 2021

Sold (Public Record)

Public Record #1468060049

$700,000—
Mar 21, 2019

Listed (Active)

New England Real Estate Network #4741360

$835,000—
DateEvent & SourcePrice
08/27/2021

Sold

New England Real Estate Network #4741360

$700,000
08/02/2021

Sold (Public Record)

Public Record #1468060049

$700,000
03/21/2019

Listed (Active)

New England Real Estate Network #4741360

$835,000

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

Public Records for 362 Upper Road

Taxable ValueLand$194,600Additions$649,600Total$844,200
Tax Record2024$14,047 ($1,171 / month)
Home Facts
Total Finished SqFt5,653 SqFtAbove Grade Finished SqFt5,653 SqFtStories2Lot Size174,240 SqFtStyleHotel / MotelYear Built1860CountyWINDSORAPN(026) 06-012

Schools near 362 Upper Road

This home is within Windsor Central Unified Union School District.
Rating
School
Type
Grades
Distance
The Prosper Valley School
Public - 5 to 6
Woodstock Senior Uhsd #4
Public - 7 to 12
Rating
School
Distance
The Prosper Valley School
Public5 to 6

Woodstock Senior Uhsd #4
Public7 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.

Similar Homes

Nearby off-market homes

AddressSold priceBedsBathsSqftLot AC
338 Upper Road, Bridgewater, VT 05035
–
3
1,271
0.75
Cemetery Road, Bridgewater, VT 05035
$69,900
2
–
1
100 A Rt 100a, Bridgewater, VT 05035
$155,000
4
2,000
2
Upper Road, Bridgewater, VT 05035
$196,000
4
2,500
10
4 Rt, Bridgewater, VT 05035
$53,000
3
600
1

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 Williamson Group Sothebys Intl. 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 07/22/2026 02:46 AM