465 Pennell Road

Closed 9/30/25Virtual Tour

Sold

Last Sold Price

$1,375,000

4 beds5 baths5,700 sqft

465 Pennell Rd, Chester, VT 05143

Single FamilyProperty Type

79.46 acresLot Size

1967Year Built

$241/sq ftPrice per sq ft

3 carsParking Spaces

Description

Discover a truly exceptional, custom-built contemporary home nestled on approximately 79 breathtaking acres with panoramic views, offering the ultimate Vermont lifestyle. This versatile 4-bedroom residence features a flexible floor plan that includes a private in-law suite, perfect for extended family, guests, or additional living options. The setting is nothing short of spectacular. Enjoy two spring-fed ponds ideal for swimming and fishing, a charming sugar house, and an enchanting treehouse tucked...Discover a truly exceptional, custom-built contemporary home nestled on approximately 79 breathtaking acres with panoramic views, offering the ultimate Vermont lifestyle. This versatile 4-bedroom residence features a flexible floor plan that includes a private in-law suite, perfect for extended family, guests, or additional living options. The setting is nothing short of spectacular. Enjoy two spring-fed ponds ideal for swimming and fishing, a charming sugar house, and an enchanting treehouse tucked among the trees. Sports enthusiasts will love the full-size tennis court, while hobbyists and makers will appreciate the oversized detached garage, perfect as a workshop or studio space. Recent updates add comfort and peace of mind, including a whole-house generator, updated appliances, new flooring and carpeting, and a freshly painted entryway. The expansive wrap-around deck invites you to relax and soak in the stunning scenery year-round. Located just minutes from Okemo Mountain and the vibrant village of Chester, this rare property is the perfect blend of seclusion, recreation, and convenience. Whether you are looking for a family compound, private retreat, or year-round residence, this one-of-a-kind estate has it all.

Listing Agent

Gary Coger
Listing Agent
Four Seasons Sotheby's Int'l Realty
gary.coger@fourseasonssir.com
P: (802) 824-3113
M: (802) 591-7262
Call Text Email

Sold By Brattleboro Area Realty

Listing closed: 09/30/2025 12:00 AM • Source: New England Real Estate Network, MLS#: 5047450

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Location

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$8,973 per month

30 year fixed, 7.03% Interest

Principal and Interest

$7,341

Property Taxes

$1,633

HOA Dues

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Property Information for 465 Pennell Road

Property Details

Taxes: $19,592 / year
MLS Type: Residential / Single Family
County: Windsor County
Zoning: RES

Building Information

Stories: 1
Year Built: 1967
Lot Size: 79.46 AC / 3,461,277 SF

Summary

Location and General Information

City: Chester
County: VT-Windsor

Directions: Take RT 103 to Smokeshire Rd. Make the right on Pennell Rd and take up the hill and veer left into the driveway.
Latitude: 43.348200594119078
Longitude: -72.644245424606282
Road Frontage: No
Seasonal: No
State: VT
Street Designation: Road
Zip Code: 05143

Taxes and HOA Information

SPAN Number: 144-045-11343
Tax Year: 2024

Taxes TBD: No

Parking

Garage: Yes
Garage Capacity: 3.00

Driveway: Gravel

Virtual Tour

Property Panorama Virtual Tour: https://tour.neren.com/465-Pennell-Road-Chester-VT-05143/unbranded

Property

Lot Information

Lot Features: Country Setting, Mountain View, Pond, Pond Frontage, Rolling, Secluded, Sloping, View, Water View, Wooded, Mountain, Near Skiing
Lot Size Acres: 79.46

Total Finished Area: 5700.0
Above Grade Finished Area: 4400.0
Above Grade Finished Area Source: Public Records
Above Grade Unfinished Area: 0.0
AboveGradeUnfinishedAreaSource: Public Records
Below Grade Finished Area: 1300.0
Below Grade Finished Area Source: Public Records
Below Grade Unfinished Area: 0.0
BelowGradeUnfinishedAreaSource: Public Records
Lot Size Square Feet: 3461278.0
Total Area: 5700.0

Property and Assessments

Current Use: Yes
Property Class: Residential

Property Type: Single Family
Flood Zone: No
PreConstruction: No
Surveyed: No
Year Built: 1967

Utilities

Electric: 200+ Amp Service, Generator
Sewer: Leach Field, Septic

Water Source: Drilled Well
Utilities: Cable Available, Phone, Propane, Satellite
Internet: Fiber Optic Internet

Interior and Exterior Features

Exterior Features

Construction Materials: Wood Frame
Roof: Flat, Membrane, Standing Seam

Interior Features

Appliances: Dishwasher, Disposal, Dryer, Freezer, Microwave, Gas Range, Refrigerator, Trash Compactor, Washer, Gas Stove, Water Heater off Boiler, Wine Cooler
Basement: Yes

Basement Access Type: Walkout
Basement Description: Concrete, Concrete Floor, Finished, Interior Stairs, Walkout
Rooms: Level 1: Level 1: Bedroom, Level 1: Den, Level 1: Dining Room, Level 1: Eat-in Kitchen, Level 1: Laundry Room, Level 1: Living Room, Level 1: Mudroom, Level 1: Other
Rooms: Level 2: Level 2: Primary Bdm Ste
Rooms: Level B: Level B: Bedroom, Level B: Studio, Level B: Wine Cellar
Flooring: Carpet, Hardwood, Manufactured, Tile, Wood
Heating: Propane, Baseboard, Hot Water, Multi Zone, Radiant Floor, Wood Stove
Cooling: Central AC
Total Stories: 1.5
Rooms Total: 13
Bathrooms Full: 1
Bathrooms Half: 1
Bathrooms One Quarter: 0
Bathrooms Three Quarter: 3
Bedrooms Total: 4
Bathrooms Total: 5

Room Information

Room 1

Room Dimensions: 27X18
Room Level: 1

Room Type: Living Room

Room 2

Room Dimensions: 14X16
Room Level: 1

Room Type: Dining Room

Room 3

Room Dimensions: 15X17
Room Level: 1

Room Type: Eat-in Kitchen

Room 4

Room Dimensions: 10X15
Room Level: 1

Room Type: Den

Room 5

Room Dimensions: 13X14
Room Level: 1

Room Type: Bedroom

Room 6

Room Dimensions: 12X15
Room Level: 1

Room Type: Laundry Room

Room 7

Room Dimensions: 10X10
Room Level: 1

Room Type: Mudroom

Room 8

Room Dimensions: 20X9
Room Level: 1

Room Type: Other

Room 9

Room Dimensions: 21X25
Room Level: 2

Room Type: Primary BR Suite

Room 10

Room Dimensions: 14X14
Room Level: 2

Room Type: Bedroom with Bath

Room 11

Room Dimensions: 19X12
Room Level: Basement

Room Type: Studio

Room 12

Room Dimensions: 14X14
Room Level: Basement

Room Type: Bedroom

Room 13

Room Dimensions: 10X10
Room Level: Basement

Room Type: Wine Cellar

Property History for 465 Pennell Road

Date	Event & Source	Price	Appreciation
Sep 30, 2025	Sold (Public Record) Public Record #1915472958	$1,375,000	+1.3% / yr
Sep 30, 2025	Sold New England Real Estate Network #5047450	$1,375,000	—
Sep 30, 2025	Pending New England Real Estate Network #5047450		—
Jun 19, 2025	Listed (Active) New England Real Estate Network #5047450	$1,500,000	—
Jun 28, 2023	Sold (Public Record) Public Record #1514510607	$1,335,000	+16452.4% / yr
Jun 28, 2023	Sold New England Real Estate Network #4918189	$1,335,000	—
Jun 27, 2023	Pending New England Real Estate Network #4918189		—
May 23, 2023	Active Under Contract New England Real Estate Network #4918189		—
Sep 30, 2022	Sold (Public Record) Public Record #1499257422	$30,000	-30.7% / yr
Jun 29, 2022	Listed (Active) New England Real Estate Network #4918189	$1,685,000	—
Jun 28, 2021	Listed (Active) New England Real Estate Network #4869423	$1,135,000	—
Aug 8, 2017	Sold (Public Record) Public Record #602735212	$197,500	—

Date	Event & Source	Price
09/30/2025	Sold (Public Record) Public Record #1915472958	$1,375,000 +1.3% / yr
09/30/2025	Sold New England Real Estate Network #5047450	$1,375,000
09/30/2025	Pending New England Real Estate Network #5047450	—
06/19/2025	Listed (Active) New England Real Estate Network #5047450	$1,500,000
06/28/2023	Sold (Public Record) Public Record #1514510607	$1,335,000 +16452.4% / yr
06/28/2023	Sold New England Real Estate Network #4918189	$1,335,000
06/27/2023	Pending New England Real Estate Network #4918189	—
05/23/2023	Active Under Contract New England Real Estate Network #4918189	—
09/30/2022	Sold (Public Record) Public Record #1499257422	$30,000 -30.7% / yr
06/29/2022	Listed (Active) New England Real Estate Network #4918189	$1,685,000
06/28/2021	Listed (Active) New England Real Estate Network #4869423	$1,135,000
08/08/2017	Sold (Public Record) Public Record #602735212	$197,500

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

Public Records for 465 Pennell Road

Taxable Value

Land

$58,000

Additions

$242,400

Total$300,400

Tax Record

2025

$13,921 ($1,160 / month)

Home Facts

Baths

Total Finished SqFt

6,071 SqFt

Above Grade Finished SqFt

3,844 SqFt

Finished Basement SqFt

2,227 SqFt

Lot Size

139,392 SqFt

Style

Miscellaneous Commercial

Year Built

1977

Year Renovated

1977

County

WINDSOR

APN

(041) 1R14-033

Schools near 465 Pennell Road

This home is within Green Mountain Unified School District.


Rating	School	Type	Grades	Distance
6/10	Chester-Andover Usd #29	Public - Serves this home	PK to 6	6.3 mi
7/10	Green Mountain Uhsd #35	Public - Serves this home	7 to 12	7.3 mi


Rating	School	Distance
6/10	Chester-Andover Usd #29 PublicPK to 6 Serves this home	6.3 mi
7/10	Green Mountain Uhsd #35 Public7 to 12 Serves this home	7.3 mi

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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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. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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 10/06/2026 04:46 PM