465 Pennell Rd

Chester, VT 05143

$1,375,000
Last Sold Price
4
Beds
5,700 Sq. Ft.
$241 / Sq. Ft.
5,700
Sq. Ft.
$241
per Sq. Ft.
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Closed 9/30/25Virtual Tour
Closed 9/30/25Virtual Tour

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.
  1. Listed by Gary Coger • Four Seasons Sotheby's Int'l Realty • gary.coger@fourseasonssir.com

Sold By Brattleboro Area Realty

Property Details for 465 Pennell Road

Zoning
RES
LISTING CLOSED: 09/30/2025 12:00 AM

Property Details for 465 Pennell Road

StatusClosed
MLS #5047450
Days on Market21
Taxes$19,592 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1967
Lot Size79.46 AC / 3,461,277 SF
CountyWindsor County
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Location

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Building Information for 465 Pennell Road

Stories1Year Built1967Building Size-Lot Size79.46 AC / 3,461,277 SF

Payment Calculator

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$8,484 per month

30 year fixed, 6.36% Interest

Principal and Interest

$6,852

Property Taxes

$1,633

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 465 Pennell Road

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
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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
  • Construction Status: Existing
  • 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

DateEvent & SourcePriceAppreciation
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

—
DateEvent & SourcePrice
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

—

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

Public Records for 465 Pennell Road

Taxable ValueLand$58,000Additions$242,400Total$300,400
Tax Record2024$8,770 ($731 / month)
Home Facts
Total Finished SqFt3,844 SqFtAbove Grade Finished SqFt3,844 SqFtLot Size139,392 SqFtStyleMiscellaneous CommercialYear Built1977CountyWINDSORAPN(041) 1R14-033

Schools near 465 Pennell Road

This home is within Green Mountain Unified School District.
Rating
School
Type
Grades
Distance
Chester-Andover Usd #29
Public - PK to 6
Green Mountain Uhsd #35
Public - 7 to 12
Rating
School
Distance
Chester-Andover Usd #29
PublicPK to 6

Green Mountain Uhsd #35
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.

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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 07/18/2026 10:18 AM