SOLD SEP 30, 2025

Listed by Gary Coger • Four Seasons Sotheby's Int'l Realty (gary.coger@fourseasonssir.com). Bought with Brattleboro Area Realty.

Off Market Sep 2025 for $1.3M

$1,559,338

•

5,700

sq ft

465 Pennell Rd, Chester, VT 05143

About this home

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.

Single-familyProperty Type

1967Year Built

79.46 acresLot Size

$274Est. Price/Sq.Ft.

3 car garageParking

Listed by Gary Coger • Four Seasons Sotheby's Int'l Realty

Contact: gary.coger@fourseasonssir.com

Bought with Christine Lewis • Brattleboro Area Realty

Redfin checked: 2 minutes ago

•Source:PrimeMLS #5047450

Redfin Estimate

$1,559,338

$184K since sold in September 2025$93K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 40.2% higher than the average sale price ($1.11M) of 6 comparable homes.

SOLD OCT 10, 2025
$598,000
A
3 beds2.5 baths2,264 sq ft
2510 E Hill Rd, Andover, VT 05143
SOLD JUN 30, 2026
$1,499,000
B
4 beds3.5 baths3,560 sq ft
652 Tierney Rd, Cavendish, VT 05142
SOLD APR 3, 2026
$675,000
C
4 beds3 baths2,200 sq ft
320 Pennell Rd, Cavendish, VT 05142
SOLD NOV 20, 2025
$845,000
D
4 beds4 baths3,278 sq ft
2904 E Hill Rd, Andover, VT 05143
SOLD MAR 20, 2026
$695,000
E
5 beds3 baths3,480 sq ft
137 Quarry Rd, Cavendish, VT 05142
SOLD MAY 12, 2026
$2,360,000
F
4 beds4.5 baths6,548 sq ft
657 Town Farm Rd, Ludlow, VT 05149

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Earn from this home

Rent

$4,302/mo

Redfin rental estimate

List your home for rent

Market trends in 05143, VT

Last updated July 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

96.2%

+1.2% MoM

Median sale price

$432K

$35K MoM

Avg. days on market

80d

58 days MoM

Recently sold homes

4 MoM

New listings for sale

NEW 29 HRS AGO
$610,000
4 beds2 baths1,908 sq ft
548 Crow Hill Rd, Chester, VT 05143
VIDEO TOUR
$995,000
3 beds3 baths2,167 sq ft
979 Andover Ridge Rd, Andover, VT 05143
COMING SOON
$255,000
3 beds1.5 baths1,683 sq ft
159 Lower Bartonsville Rd, Chester, VT 05143
$289,900
3 beds2.5 baths1,508 sq ft
3713 Trebo Rd, Chester, VT 05143
See all

Provided by Redfin

Sale history for 465 Pennell Rd

Tax history for 465 Pennell Rd

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

—

Lot width

—

Lot depth

—

Lot size

3.2 Acres

Year renovated

—

Sq. Ft.

3,844

Year built

1977

Style

Single Family Residential

County

Windsor County

APN

13204110768

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 15, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 3

Interior

Virtual Tour

Bathroom Information
# of Baths (full): 1
# of Baths (3/4): 3
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Walkout
Concrete, Concrete Floor, Finished, Stairs - Interior, Walkout

Other Interior Features
# of Rooms: 13
Level B: Bedroom, Level B: Studio, Level B: Wine Cellar
Flooring: Carpet, Hardwood, Manufactured, Tile, Wood

Equipment & Appliance Information
Dishwasher, Disposal, Dryer, Freezer, Microwave, Range - Gas, Refrigerator, Trash Compactor, Washer, Stove - Gas, Water Heater - Off Boiler, Wine Cooler

Room 1 Information
Living Room
Living Room
Dimensions: 27X18
Level: 1

Room 2 Information
Dining Room
Dimensions: 14X16
Level: 1

Room 3 Information
Eat-In Kitchen
Dimensions: 15X17
Level: 1

Room 4 Information
Den
Dimensions: 10X15
Level: 1

Room 5 Information
Bedroom
Dimensions: 13X14
Level: 1

Room 6 Information
Laundry Room
Laundry Room
Dimensions: 12X15
Level: 1

Room 7 Information
Mudroom
Dimensions: 10X10
Level: 1

Room 8 Information
Other
Dimensions: 20X9
Level: 1

Room 9 Information
Master Bedroom Suite
Dimensions: 21X25
Level: 2

Room 10 Information
Bedroom with Bath
Dimensions: 14X14
Level: 2

Room 11 Information
Studio
Dimensions: 19X12
Level: Basement

Room 12 Information
Bedroom
Dimensions: 14X14
Level: Basement

Room 13 Information
Wine Cellar
Dimensions: 10X10
Level: Basement

Exterior

Building Information
Architectural Style: Contemporary
Construction Status: Existing
Construction Materials: Wood Frame
Approximate Sq. Ft. Total Finished: 5700
Approximate Sq. Ft. Total: 5700
Roof: Flat, Membrane, Standing Seam

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot Features: Country Setting, Mountain View, Pond, Pond Frontage, Rolling, Secluded, Sloping, View, Water View, Wooded, Mountain, Near Skiing

Other Property & Lot Information
Year Built: 1967

Financial

Tax Information
Tax Year: 2024
Gross Amount Tax: 19592.26
SPAN Number: 144-045-11343

Other Tax Information
Page Deed: 20

Utilities

Heating & Cooling Information
Cooling: Central AC
Heat: Propane, Baseboard, Hot Water, Multi Zone, Radiant Floor, Stove - Wood

Sewer Information
Leach Field, Septic

Electric Information
200 Amp, Generator

Water Information
Water Source: Drilled Well

Other Utilities Information
Internet: Internet - Fiber Optic
Phone, Cable - Available, Gas - LP/Bottle, Satellite

Location

Other Location Information
Directions: Take RT 103 to Smokeshire Rd. Make the right on Pennell Rd and take up the hill and veer left into the driveway.

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 3,844
Stories: —
Lot Size: 3.2 acres
Style: Single Family Residential
Year Built: 1977
Year Renovated: —
County: Windsor County
APN: 13204110768

Home facts updated by county records on Jul 15, 2026

Around this home

Schools
Places
Transit

Some nearby schools may not be within this home's attendance zone. Please check the Green Mountain Unified School District website to verify.

Cavendish Town Elementary School

Public PreK-6 • 2.5mi

Ludlow Elementary School

Public PreK-6 • 4.1mi

7/10

Okemo Mountain School

Private 7-12 • 4.1mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

1/10 Heat Factor

7 days above 88° expected this year, 15 days in 30 years

3/10 Wind Factor

5% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Chester, VT • 05143

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.5 hours in June and 3.5 hours in December, placing it below the U.S. average for solar exposure.

8.5 hrs

3.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.48M – $1.79M

Sell confidently with a local market expert in Chester. 3 minutes to get started.

Nearby similar homes

$1,200,000

4 beds2 baths1,908 sq ft

366 Knapp Pond Rd, Cavendish, VT 05142

$1,970,000

5 beds5.5 baths4,965 sq ft

93 Godfrey Rd, Ludlow, VT 05149

NEW 29 HRS AGO

$610,000

4 beds2 baths1,908 sq ft

548 Crow Hill Rd, Chester, VT 05143

3D WALKTHROUGH

$449,000

4 beds3 baths3,129 sq ft

29 Piper Rd, North Springfield, VT 05150

$700,000

5 beds4 baths3,641 sq ft

488 Andover Rd, Ludlow, VT 05149

VIDEO TOUR

$150,000

4 beds4 baths2,838 sq ft

6 Mill St, Ludlow, VT 05149

New listings for sale in 05143

NEW 29 HRS AGO

$610,000

4 beds2 baths1,908 sq ft

548 Crow Hill Rd, Chester, VT 05143

VIDEO TOUR

$995,000

3 beds3 baths2,167 sq ft

979 Andover Ridge Rd, Andover, VT 05143

COMING SOON

$255,000

3 beds1.5 baths1,683 sq ft

159 Lower Bartonsville Rd, Chester, VT 05143

$289,900

3 beds2.5 baths1,508 sq ft

3713 Trebo Rd, Chester, VT 05143

Home values near 465 Pennell Rd

Data from public records.

Address	Redfin Estimate
320 Pennell Rd, Cavendish, VT 4 Beds \| 3 Baths \| 2200 Sq. Ft.	$758,928
63 Cemetery Rd, Chester, VT 3 Beds \| 2 Baths \| 2843 Sq. Ft.	$644,451

Address	Redfin Estimate
240 Suursoo Rd, Chester, VT 4 Beds \| 1.5 Baths \| 1926 Sq. Ft.	$496,388
1229 Smokeshire Rd, Chester, VT 3 Beds \| 3 Baths \| 2672 Sq. Ft.	$523,697

Address	Redfin Estimate
692 Smokeshire Rd, Chester, VT 3 Beds \| 2 Baths \| 1360 Sq. Ft.	$460,448
159 Murdock Rd, Chester, VT 2 Beds \| 1 Baths \| 560 Sq. Ft.	$578,514

Property information provided by PrimeMLS when last listed in 2025. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05143, VT

Sale history for 465 Pennell Rd

Tax history for 465 Pennell Rd

Public record

Property details

Around this home

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05143

Home values near 465 Pennell Rd

More real estate resources