Sign up to get new listings emailed daily! JOIN SIGN IN
Kayla Brown
REALTOR®
VCard Icon 

1888 Winhall Hollow Road, Londonderry, VT 05155

$450,000
  • Main Photo

4 Photos

Active Under Contract
LOT SIZE 83.070 acres MLS#5104960
STATUSActive Under Contract PROPERTY TYPELand - Lot/Land SCHOOLBennington-Rutland

Listing Courtesy of: Four Seasons Sothebys Intl Realty
Agency Phone: 802-362-4551
Associate Name: Andy Reed
IDX logo


Property Description

Nestled along desirable Winhall Hollow Road in South Londonderry, this beautiful undeveloped Vermont property offers a rare opportunity to create a private mountain retreat, recreational getaway, or explore future development potential. The land features a picturesque blend of gently rolling open meadow and mature forest, with power available along the road and an old seasonal camp already in place. Ideally situated just minutes from the Stratton Mountain access road, the property provides convenient access to Stratton, Bromley, and Magic Mountain, making it an exceptional four-season location for skiing, hiking, biking, and outdoor recreation. Whether you're envisioning a secluded homesite, a long-term investment, or a place to enjoy hunting and the natural beauty of Southern Vermont, this scenic parcel offers endless possibilities. Access to camp on the north side by a shared ROW. South side has its own possible access. Buyers considering development should perform their own due diligence with the Town of Londonderry and the State of Vermont regarding zoning, wastewater permitting, wetlands, and any applicable Act 250 requirements.

1888 Winhall Hollow Road | MLS# 5104960

This land located at 1888 Winhall Hollow Road, Londonderry, VT 05155 is currently listed for sale with an asking price of $450,000. The property has approximately 83.07 Acres. Winhall Hollow Road is located within the Bennington-Rutland school district. Search Londonderry real estate on kaylabrown.masiellogrouprealestate.com today.

Property Features

Property Type: Land - Lot/Land
Lot Size: 83.07 Acres
Taxes: $4,773

Feature Descriptions

Days on Site: 31
Easements: Yes
Electric: At Street
Flood Zone: No
Lot: Near Skiing, Rural, Country Setting, Field/Pasture, Secluded, Wetlands, Wooded, Private
Road Frontage: 23873
Roads: Paved, Public, Public Maintained Road
Sewer: None
Surveyed: Yes
Water: On-Site Well Needed
Wooded: Yes
Zoning: R3

Local Schools

High School: Choice
Middle School: Flood Brook Union School
Elementary School: Flood Brook Elementary School
School District: Bennington-Rutland

Listed By / Shown By

Listed By

Agency Name: Four Seasons Sothebys Intl Realty
Agent Name: Andy Reed
Agency Phone: 802-362-4551

IDX logo

TOUR PROPERTY

Choose a date and time to see 1888 Winhall Hollow Road, Londonderry, VT 05155.
I will get in touch with you shortly.

Request a Showing
Choose your video chat app
  • Monday September 14
  • Tuesday September 15
  • Wednesday September 16
  • Thursday September 17
  • Friday September 18
  • Saturday September 19
  • Sunday September 20
  • Monday September 21
  • Tuesday September 22
  • Wednesday September 23
  • Thursday September 24
  • Friday September 25
  • Saturday September 26
  • Sunday September 27
  • Monday September 28
  • 7:00 AM
  • 7:30 AM
  • 8:00 AM
  • 8:30 AM
  • 9:00 AM
  • 9:30 AM
  • 10:00 AM
  • 10:30 AM
  • 11:00 AM
  • 11:30 AM
  • 12:00 PM
  • 12:30 PM
  • 1:00 PM
  • 1:30 PM
  • 2:00 PM
  • 2:30 PM
  • 3:00 PM
  • 3:30 PM
  • 4:00 PM
  • 4:30 PM
  • 5:00 PM
  • 5:30 PM
  • 6:00 PM
  • 6:30 PM
  • 7:00 PM
  • 7:30 PM
  • 8:00 PM
  • 8:30 PM
  • 9:00 PM
Preferred Communication Method

Estimate Your Payment

Estimated Payment

$ 1,530.50 per month $1,001.50 Principal & Interest $397.75 Property Tax $131.25 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 09/13/2026. The listing information on this page last changed on 09/13/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 09/13/2026 12:08:00 AM EST) or MLSPIN MLS (last updated Sat 09/12/2026 11:38:36 PM EST) or Prime MLS (last updated Sat 09/12/2026 11:33:34 PM EST) or MREIS (last updated Sun 09/13/2026 12:05:16 AM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display 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 2026-09-12 23:33:34

Privacy Policy / DMCA Notice / ADA Accessibility

Agency License Information: Better Homes and Gardens® and the Better Homes and Gardens Real Estate Logo are registered service marks owned by Meredith Corporation and licensed to Better Homes and Gardens Real Estate LLC. The Masiello Group Limited fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC nor any of its affiliated companies.


Login to My Homefinder