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$1,375,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 1 Full Bath
  • 4 Partial Baths
  • 5,700 Sq. Ft.
  • 79.46 Acres
  • 3 Car Garage
See This Home
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See This Home
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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.

Full Property Details for 465 Pennell Rd

General

  • Sold For: $1,375,000
  • Taxes: $19,592 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: PrimeMLS
  • MLS ID: 5047450
  • Added to Site: 259 day(s) ago

Interior

  • Number of Rooms: 13
  • Interior Features: Cathedral Ceiling, Ceiling Fan, Dining Area, Hot Tub, Kitchen Island, Kitchen/Dining, Living/Dining, Primary BR w/ BA, Natural Light, Natural Woodwork, Soaking Tub, Vaulted Ceiling, Wood Stove Hookup, 1st Floor Laundry
  • Appliances: Dishwasher, Disposal, Dryer, Freezer, Microwave, Gas Range, Refrigerator, Trash Compactor, Washer, Gas Stove, Water Heater off Boiler, Wine Cooler
  • Flooring: Carpet, Hardwood, Manufactured, Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 1
  • 3/4 Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: 21 x 25, Level 2
  • Bedroom 1: 13 x 14, Level 1
  • Bedroom 2: 14 x 14, Basement

Other Rooms

  • Living Room: 27 x 18, Level 1
  • Dining Room: Dining Room, 14 x 16, Level 1
  • Den: Den, 10 x 15, Level 1
  • Wine Cellar: 10 x 10, Basement
  • Laundry: 12 x 15, Level 1
  • Other Room 1: 20 x 9, Level 1
  • Studio: 19 x 12, Basement
  • Mud Room: Mudroom, 10 x 10, Level 1

Exterior

  • Exterior Features: Docks, Balcony, Deck, Hot Tub, Natural Shade, Tennis Court

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Parking: Heated Garage, Attached, Detached

Location

  • County: Windsor
  • Driving Directions: Take RT 103 to Smokeshire Rd. Make the right on Pennell Rd and take up the hill and veer left into the driveway.

Heating & Cooling

  • Cooling Type: Central AC
  • Heating Type: Propane, Baseboard, Hot Water, Multi Zone, Radiant Floor, Wood Stove

Utilities

  • Sewer: Leach Field, Septic

Structural Information

  • Construction Status: Existing
  • Basement Entrance: Walkout
  • Basement Desc.: Concrete, Concrete Floor, Finished, Interior Stairs, Walkout
  • Roof: Flat, Membrane, Standing Seam
  • Stories/Levels: 1.5
  • Square Feet: 5,700
  • Finished Total: 5,700 Sq. Ft.
  • Finished Above Grnd: 4,400 Sq. Ft.
  • Finished Below Grnd: 1,300 Sq. Ft.
  • Current Bldg. Use: Yes
  • Year Built: 1967

Lot Features

  • Lot Size (Acres): 79.46
  • Lot Size (Sq. Ft.): 3,461,278
  • Frontage: No Road Frontage
  • Driveway/Sidewalk: Gravel
  • Zoning: RES

Financial Considerations

  • Price Per Sq. Ft.: $263.16
  • Tax Amount: $19,592.26
  • Tax Year: 2024

Disclosures and Reports

  • APN: 144-045-11343

Listed by Four Seasons Sotheby's Int'l Realty, Gary Coger
Sold by Brattleboro Area Realty, Christine M. Lewis

Listed by Four Seasons Sotheby's Int'l Realty, Gary Coger
Sold by Brattleboro Area Realty, Christine M. Lewis

Listing agent

— 465 Pennell Rd —

  • Gary Coger

    Four Seasons Sotheby's Int'l Realty

gary.coger@fourseasonssir.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Price & Sales History for 465 Pennell Rd

Date
Details
Price
Change
Source
9/30/2025
Sold
$1,375,000
-8.33%
MLS
6/19/2025
Listed
$1,500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Four Seasons Sotheby's Int'l Realty, Gary Coger
Sold by Brattleboro Area Realty, Christine M. Lewis

465 Pennell Road, Chester, VT 05143 (MLS# 5047450) is a Single Family property that was sold at $1,375,000 on September 30, 2025. Want to learn more about 465 Pennell Road? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.