5855 Windham Hill Road
Windham, VT 05359
2 Beds
2 Baths
$499,000
$499,000
2 Beds
2 Baths
(on 33.34 acres)
We estimate this home will sell faster than 84% nearby.
Home Highlights
Climate Control
Wood, Baseboard, Hot Water, Wood Boiler, Mini Split & Mini Split
Listed
7 days ago
Local Information
- Map ViewExplore the area around 5855 Windham Hill Road.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Last check for updates: about 7 hours ago
Listing courtesy of Keith Nowak
Four Seasons Sotheby's Int'l Realty, (802) 464-1200
Source: PrimeMLS, MLS#5104617
Also Listed on PrimeMLS.
About this House
Bring your vision to life on 33.34 acres in the scenic hills of Windham, Vermont. This partially completed home offers a rare opportunity to finish a thoughtfully designed residence surrounded by open meadows, established trails, and an idyllic rural setting. Designed with a 4 bedroom septic system, the home is ready for the next owner to complete the interior and exterior finishes. The clapboard siding remains unfinished, and the lower level walk out basement is plumbed for a third full bathroom, offering additional flexibility for finished living space. A substantial 24' x 48' completed foundation is in place for the planned garage. It will accommodate a 24' x 24' two car garage plus an additional 24' x 24' area of approximately 552 square feet, ready to be finished and purposed according to your needs, ideal for a workshop, studio, storage, recreation space, or other use. The land is equally appealing, with expansive meadows featuring tillable soils formerly used to grow organic fruits and vegetables, established trails, mature woods, and high quality gravel on the property. Adding to the sense of privacy and protected open space, the property abuts a National Wildlife Refuge along its western and northern boundaries. Enjoy gardening, exploring the trails, working on projects, or simply taking in the peaceful Vermont landscape. Conveniently located within reach of Stratton, Magic, and Bromley Mountains and the villages of Londonderry, Chester, and Grafton. An exceptional opportunity to complete a substantial Vermont property and create something truly your own.
We estimate this home will sell faster than 84% nearby.
Home Details for 5855 Windham Hill Road
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MLS Status: Active |
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Interior Details Basement: Concrete,Concrete Floor,Walkout,Basement Stairs,Interior EntryNumber of Rooms: 5 |
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 1 |
Appliances & Utilities Utilities: Cable |
Heating & Cooling Heating: Wood,Baseboard,Hot Water,Wood Boiler,Mini SplitHas CoolingAir Conditioning: Mini SplitHas HeatingHeating Fuel: Wood |
Gas & Electric Electric: 200+ Amp Service |
Levels, Entrance, & Accessibility Stories: 1Levels: One |
View Has a View |
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Exterior Home Features Roof: ShingleFoundation: Concrete |
Parking & Garage No GarageParking: Dirt |
Frontage Road Frontage: Public |
Water & Sewer Sewer: 1000 Gallon, On-Site Septic Exists |
Farm & Range Frontage Length: Road frontage: 1300 |
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Days on Market: 7 |
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Year Built Year Built: 2006 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: New Englander |
Building Construction Materials: Wood FrameIs a New Construction |
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Price List Price: $499,000 |
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Direction & Address City: Windham |
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Listing Agent Listing ID: 5104617 |
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Building Area Building Area: 3320 Square Feet |
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Lot Area: 33.34 Acres |
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BasementMls Number: 5104617Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 1660Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet |
Around this home
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.
What Locals Say about Londonderry
At least 6 Trulia users voted on each feature.
100 % Say car is needed
100 % Say parking is easy
100 % Say it's dog friendly
100 % Say there's wildlife
89 % Say there's holiday spirit
67 % Say people would walk alone at night
67 % Say they plan to stay for at least 5 years
58 % Say it's quiet
57 % Say neighbors are friendly
57 % Say yards are well-kept
55 % Say there are community events
43 % Say it's walkable to restaurants
13 % Say it's walkable to grocery stores
13 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
Market trends in Londonderry
Last updated July 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
28
3MoM
Home Value
Trulia Estimate
$485KSince last month
Increased$122K (+33.5%)Since last year
Increased$96K (+24.6%)Since last sale
Increased$404K (+499.1%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +281% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $485K |
| July 2026 | $364K |
| June 2026 | $357K |
| May 2026 | $366K |
| April 2026 | $357K |
| March 2026 | $358K |
| February 2026 | $326K |
| January 2026 | $310K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
1.05 | Single-Family Home | $475,000 | 09/18/25 | 3 | 2 | 2,160 | |
1.18 | Single-Family Home | $147,000 | 08/22/25 | 2 | 1 | 1,230 | |
1.39 | Single-Family Home | $320,000 | 12/12/25 | 3 | 2.5 | 1,266 | |
1.73 | Single-Family Home | $390,000 | 10/03/25 | 3 | 2 | 1,554 | |
2.24 | Single-Family Home | $625,000 | 01/15/26 | 2 | 2 | 2,144 | |
1.75 | Single-Family Home | $572,500 | 01/05/26 | 4 | 3 | 2,344 | |
2.46 | Single-Family Home | $375,000 | 07/24/26 | 3 | 2 | 1,600 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.07 | $715,300 | 4 | 4 | 3,854 | Off Market | |
0.55 | $343,900 | 2 | 2.5 | 1,410 | Off Market | |
0.57 | $49,000 | - | - | - | Recently Sold | |
0.66 | $546,200 | 4 | 1.5 | 1,800 | Off Market | |
0.91 | $46,277 | - | - | - | Recently Sold | |
1.05 | $492,100 | 3 | 2 | 2,160 | Off Market | |
1.05 | $398,200 | 6 | 2 | 3,005 | Off Market | |
1.18 | $152,700 | 2 | 1 | 1,230 | Off Market | |
1.24 | - | - | - | - | Off Market | |
1.32 | - | - | - | - | Off Market | |
1.39 | $320,000 | 3 | 2.5 | 1,266 | Recently Sold |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Aug 12, 2026 Source: PrimeMLS #5104617 | Listed For Sale | $499,000 |
Jul 27, 2004 Source: N/A | Sold | $81,000 |
| Year | Property tax | Tax assessment |
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| 2024 | Unavailable | $327,100 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Keith Nowak, Four Seasons Sotheby's Int'l Realty, (802) 464-1200
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 2026-08-19 16:59:13 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.
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Frequently asked questions about 5855 Windham Hill Road
- What is the estimated monthly payment for 5855 Windham Hill Road?Based on a $499,000 list price with 20% down at today's rates, the estimated monthly payment for 5855 Windham Hill Road is approximately $3,459 (about $2,606 principal & interest, $778 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What do residents say about Windham?Residents describe Windham, VT as easy to park in, dog-friendly, and established. Most residents say you need a car. See homes for sale in Windham, VT.
- What are the closest schools to 5855 Windham Hill Road?The closest schools to 5855 Windham Hill Road are Leland & Gray Uhsd #34 (Middle/High, rated 3/10), Windham Elementary School (Pre-K).
- What is 5855 Windham Hill Road estimated to be worth?Trulia's estimated value for 5855 Windham Hill Road is $485,300.
- Does 5855 Windham Hill Road have air conditioning?Yes, 5855 Windham Hill Road has air conditioning.
- How big is the lot at 5855 Windham Hill Road?The lot at 5855 Windham Hill Road is about 33.3 acres.
5855 Windham Hill Road, Windham, VT 05359 is a 2 bedroom, 2 bathroom single-family home built in 2006. This property is currently available for sale and was listed by PrimeMLS on Aug 12, 2026. The MLS # for this home is MLS# 5104617.