33 Strattonwald Rd

$40,000
Price
2,791 Sq. Ft.
$172 / Sq. Ft.
2,791
Sq. Ft.
$172
per Sq. Ft.

Description

Lock in your rental for ski season '26-'27! This cheerful, modern-yet-classic Strattonwald chalet is nestled in a private community just 7 minutes to Stratton's Main Base, with shuttle access. There is so much room for everyone, with two primary bedroom suites plus two more bedrooms; a gourmet open-concept kitchen/dining/living room with wood stove; second living/TV room. Downstairs living room with extra kitchen, bonus room, bathroom and office with fast wifi offers an ideal teen or in-law suite....Lock in your rental for ski season '26-'27! This cheerful, modern-yet-classic Strattonwald chalet is nestled in a private community just 7 minutes to Stratton's Main Base, with shuttle access. There is so much room for everyone, with two primary bedroom suites plus two more bedrooms; a gourmet open-concept kitchen/dining/living room with wood stove; second living/TV room. Downstairs living room with extra kitchen, bonus room, bathroom and office with fast wifi offers an ideal teen or in-law suite. Getting to the mountain is easy: The Strattonwald shuttle is available to seasonal renters and owners, stopping right at the driveway hourly in the morning and early afternoon. No need to deal with mountain parking! Detached 2-car garage. It's a beloved house with a great vibe, built by an original Stratton ski patroller and lovingly maintained and updated. House also available 4/1/26-12/1/26 for $5250/mo. Access to private swimming pond, tennis and pickleball for long-term tenants. Come ski! Listing agent is owner.
  1. Listed by Jamie Luke • TPW Real Estate

Amenities

  • Air Conditioning
  • Driveway
  • Garage
  • Parking Included
  • Pickleball
  • Stove
  • Waterfront
LISTING UPDATED: 03/02/2026 07:45 PM

Property Details for 33 Strattonwald Road

StatusActive
MLS #5077276
Days on Market23
Rental Incentives-
Costs & Fees-
Available Date02/21/2026
Lease TermLease Length: Seasonal - Winter
Furnished-
Compass TypeRental
MLS TypeRental / Single Family
Year Built1976
Lot Size2.51 AC / 109,335 SF
CountyBennington County

Location

Listing Courtesy of TPW Real Estate
Add your commute

Building Information for 33 Strattonwald Road

Building/Complex33 Strattonwald RdFloor-Stories2Pet Policy-Pet Policy Details-Year Built1976Building Size-Lot Size2.51 AC / 109,335 SF

Property Information for 33 Strattonwald Road

Summary
Location and General Information
  • City: Winhall
  • County: VT-Bennington
  • Directions: From VT-30 in Bondville, turn onto Winhall Hollow Road. Take first right onto Strattonwald Road. House is approximately the 7th house on your left.
  • Latitude: 43.152807000001005
  • Longitude: -72.881195000000005
  • Road Frontage: Yes
  • Seasonal: Yes
  • State: VT
  • Street Designation: Road
  • Zip Code: 05340
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Gravel
Property
Lot Information
  • Lot Features: Country Setting, Hilly, Lake Access, Recreational, Secluded, Ski Area, Subdivision, Wooded
  • Lot Size Acres: 2.51
  • Road Frontage Length: 125.0
Property and Assessments
  • Property Class: Rental
  • Property Type: Single Family
  • Construction Status: Existing
  • PreConstruction: No
  • Year Built: 1976
Utilities
  • Electric Company: GMP
  • Fuel Company: Irving
  • Electric: Circuit Breaker(s), Generator
  • Sewer: Septic
  • Water Source: Drilled Well
  • Utilities: Cable at Site
  • Internet: High Speed Intrnt at Site, Cable Internet
Interior and Exterior Features
Exterior Features
  • Color: Brown
  • Association Amenities: Other
  • Construction Materials: Log Home, Cedar Exterior
  • Roof: Standing Seam
Interior Features
  • Appliances: Dishwasher, Disposal, Microwave, Refrigerator, Gas Stove, Water Heater off Boiler
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Finished, Insulated, Interior Stairs, Storage Space, Walkout, Interior Access
  • Rooms: Level 1: Level 1: Bedroom, Level 1: Bonus Room, Level 1: 3/4 Bathroom, Level 1: Mudroom, Level 1: Office/Study, Level 1: Playroom
  • Rooms: Level 2: Level 2: Bedroom, Level 2: Full Bathroom, Level 2: Family Room, Level 2: Kitchen/Living
  • Rooms: Level 3: Level 3: Full Bathroom, Level 3: Primary Bdm Ste
  • Flooring: Carpet, Hardwood, Tile
  • Heating: Oil, Baseboard, Wood Stove
  • Cooling: Mini Split
  • Total Stories: 2.5
Room Information
Room 1
  • Room Level: 3
  • Room Type: Primary BR Suite
Room 2
  • Room Level: 2
  • Room Type: Bedroom
Room 3
  • Room Level: 2
  • Room Type: Bedroom
Room 4
  • Room Level: 2
  • Room Type: Bathroom Full
Room 5
  • Room Level: 2
  • Room Type: Kitchen/Living
Room 6
  • Room Level: 2
  • Room Type: Family Room
Room 7
  • Room Level: 1
  • Room Type: Playroom
Room 8
  • Room Level: 1
  • Room Type: Bedroom
Room 9
  • Room Level: 1
  • Room Type: Office/Study
Room 10
  • Room Level: 1
  • Room Type: Bonus Room
Room 11
  • Room Level: 1
  • Room Type: Bathroom Three Quarter
Room 12
  • Room Level: 1
  • Room Type: Mudroom
Room 13
  • Room Level: 3
  • Room Type: Bathroom Full
Rental
Rent Information
  • Rental Amount Frequency: Seasonal
  • Lease Term: Seasonal - Winter

Property History for 33 Strattonwald Road

DateEvent & SourcePriceAppreciation
Feb 22, 2026

Listed (Active)

New England Real Estate Network #5077276

$40,000—
Jul 21, 2025

Rented

New England Real Estate Network #5035155

—
Apr 7, 2025

Listed (Active)

New England Real Estate Network #5035155

$40,000—
Mar 31, 2024

Rented

New England Real Estate Network #4985983

$40,000—
Mar 31, 2024

Pending

New England Real Estate Network #4985983

—
Feb 24, 2024

Listed (Active)

New England Real Estate Network #4985983

$44,000—
Nov 16, 2023

Expired

New England Real Estate Network #4970759

—
Oct 20, 2023

Price Change

New England Real Estate Network #4970759

$37,500—
Sep 20, 2023

Listed (Active)

New England Real Estate Network #4970759

$45,000—
DateEvent & SourcePrice
02/22/2026

Listed (Active)

New England Real Estate Network #5077276

$40,000
07/21/2025

Rented

New England Real Estate Network #5035155

—
04/07/2025

Listed (Active)

New England Real Estate Network #5035155

$40,000
03/31/2024

Rented

New England Real Estate Network #4985983

$40,000
03/31/2024

Pending

New England Real Estate Network #4985983

—
02/24/2024

Listed (Active)

New England Real Estate Network #4985983

$44,000
11/16/2023

Expired

New England Real Estate Network #4970759

—
10/20/2023

Price Change

New England Real Estate Network #4970759

$37,500
09/20/2023

Listed (Active)

New England Real Estate Network #4970759

$45,000

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

Schools near 33 Strattonwald Road

Rating
School
Type
Grades
Distance
Private - K to 8
Rating
School
Distance
Mountain School At Winhall
PrivateK to 8

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.

33 Strattonwald Road is available for rent in Winhall, VT 05340. This property was listed on February 22, 2026 by TPW Real Estate, it's currently listed at $40,000. It has been on the market for a total of 23 days and was last rented on July 21, 2025. Nearby schools include Mountain School At Winhall. 33 Strattonwald Road is a 4-bed, 3-bath, 2,791 sqft a property built in 1976.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of TPW Real Estate

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 03/18/2026 12:30 AM