77 Winding Road
Description
Sold By BHG Masiello Brattleboro
- Listed by: Dana Waters • Dark Horse Realty
- Listed by: Paula Waters • Dark Horse Realty
Recent comparable sales
Median sold price
$525,000
Avg days on market
33
Sale-to-list ratio
97.4%
West Windsor, VT
9 comparable properties found
$515,000
Sold 11/14/25
- 4
- Bedrooms
- 3
- Bathrooms
- 2,380
- Square Feet
- 0.5
- Acres
$460,000
Sold 01/15/25
- 4
- Bedrooms
- 4
- Bathrooms
- 2,388
- Square Feet
- 0.91
- Acres
$875,000
Sold 08/21/26
- 4
- Bedrooms
- 3
- Bathrooms
- 2,352
- Square Feet
- 80
- Acres
$525,000
Sold 06/20/25
- 3
- Bedrooms
- 2
- Bathrooms
- 2,064
- Square Feet
- 2.73
- Acres
$720,000
Sold 11/08/25
- 3
- Bedrooms
- 2
- Bathrooms
- 2,727
- Square Feet
- 10.51
- Acres
$474,800
Sold 08/27/26
- 3
- Bedrooms
- 2
- Bathrooms
- 1,480
- Square Feet
- 1.53
- Acres
$530,000
Sold 05/29/25
- 3
- Bedrooms
- 4
- Bathrooms
- 2,313
- Square Feet
- 3.49
- Acres
$485,000
Sold 08/21/26
- 5
- Bedrooms
- 3
- Bathrooms
- 3,120
- Square Feet
- 2.2
- Acres
$925,000
Sold 01/08/25
- 4
- Bedrooms
- 2
- Bathrooms
- 2,000
- Square Feet
- 38.5
- Acres
Location
Payment Calculator
$3,363 per month
30 year fixed, 6.55% Interest
$2,669
$695
$0
Know your buying power with a preapproval and custom rate in minutes
1Property Information for 77 Winding Road
- Taxes: $8,338 / year
- MLS Type: Residential / Single Family
- County: Windsor County
- Zoning: Res
- Stories: 2
- Year Built: 1988
- Lot Size: 12.20 AC / 531,432 SF
- City: West Windsor
- County: VT-Windsor
- Directions: Route 44 to Westgate Road, immediate left onto Winding Road, at fork bear left on to driveway follow past shed on left, up hill to the house (you can't see it from road.)
- Latitude: 43.454372000001001
- Longitude: -72.500583000000006
- Road Frontage: Yes
- Seasonal: No
- State: VT
- Street Designation: Road
- Zip Code: 05037
- SPAN Number: 738-235-10591
- Tax Year: 2025
- Taxes TBD: No
- Garage: Yes
- Garage Capacity: 2.00
- Driveway: Gravel, Other, Right-Of-Way (ROW)
- Lot Features: Corner, Country Setting, Mountain View, Recreational, Rolling, Secluded, Sloping, Trail/Near Trail, Walking Trails, Wooded
- Lot Size Acres: 12.2
- Road Frontage Length: 435.0
- Total Finished Area: 2380.0
- Above Grade Finished Area: 2180.0
- Above Grade Finished Area Source: Public Records
- Above Grade Unfinished Area: 0.0
- AboveGradeUnfinishedAreaSource: Public Records
- Below Grade Finished Area: 200.0
- Below Grade Finished Area Source: Public Records
- Below Grade Unfinished Area: 0.0
- BelowGradeUnfinishedAreaSource: Public Records
- Lot Size Square Feet: 531432.0
- Total Area: 2380.0
- Current Use: No
- Assessment Amount: $522,000
- Assessment Year: 2024
- Property Class: Residential
- Property Type: Single Family
- Easements: Yes
- Flood Zone: No
- PreConstruction: No
- Surveyed: Yes
- Year Built: 1988
- School District: Windsor Southeast
- High School: Windsor High School
- Middle/Jr School: Windsor High School
- Elementary School: Albert Bridge School
- Cable Company: Xfinity
- Electric: 100 Amp Service, Circuit Breaker(s), Underground
- Sewer: 1000 Gallon, On-Site Septic Exists, Septic
- Water Source: Drilled Well, Private
- Utilities: Cable
- Internet: Fiber Optic Internet
- Color: Brown
- Construction Materials: Wood Frame, Clapboard Exterior
- Roof: Asphalt Shingle
- Appliances: Dishwasher, Dryer, Freezer, Microwave, Gas Range, Refrigerator, Washer, Propane Water Heater
- Basement: Yes
- Basement Access Type: Walkout
- Basement Description: Concrete, Partial, Unfinished, Interior Access, Exterior Access, Basement Stairs
- Flooring: Carpet, Hardwood, Tile
- Heating: Propane, Baseboard, Passive Solar, Radiant, Wood Stove
- Cooling: None
- Total Stories: 2
- Rooms Total: 7
- Bathrooms Full: 2
- Bathrooms Half: 0
- Bathrooms One Quarter: 0
- Bathrooms Three Quarter: 0
- Bedrooms Total: 4
- Bathrooms Total: 2
Property History for 77 Winding Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Dec 15, 2025 | Sold (Public Record) Public Record #1929234743 | $525,000 | +7.2% / yr |
| Dec 15, 2025 | Sold New England Real Estate Network #5064038 | $525,000 | — |
| Oct 26, 2025 | Pending New England Real Estate Network #5064038 | — | |
| Oct 26, 2025 | Active Under Contract New England Real Estate Network #5064038 | — | |
| Oct 2, 2025 | Listed (Active) New England Real Estate Network #5064038 | $520,000 | — |
| Nov 30, 2016 | Sold (Public Record) Public Record #584365366 | $280,000 | — |
| Nov 28, 2016 | Sold New England Real Estate Network #4466187 | $280,000 | — |
| Jan 10, 2016 | Price Change New England Real Estate Network #4466187 | $345,000 | — |
| Jan 10, 2016 | Listed (Active) New England Real Estate Network #4466187 | $299,000 | — |
| Nov 2, 2015 | Expired New England Real Estate Network #4407287 | — | |
| Mar 16, 2015 | Listed (Active) New England Real Estate Network #4407287 | $395,000 | — |
| Jun 22, 2006 | Expired New England Real Estate Network #804759 | — | |
| May 22, 2001 | Listed (Active) New England Real Estate Network #804759 | $275,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 12/15/2025 | Sold (Public Record) Public Record #1929234743 | $525,000 +7.2% / yr |
| 12/15/2025 | Sold New England Real Estate Network #5064038 | $525,000 |
| 10/26/2025 | Pending New England Real Estate Network #5064038 | — |
| 10/26/2025 | Active Under Contract New England Real Estate Network #5064038 | — |
| 10/02/2025 | Listed (Active) New England Real Estate Network #5064038 | $520,000 |
| 11/30/2016 | Sold (Public Record) Public Record #584365366 | $280,000 |
| 11/28/2016 | Sold New England Real Estate Network #4466187 | $280,000 |
| 01/10/2016 | Price Change New England Real Estate Network #4466187 | $345,000 |
| 01/10/2016 | Listed (Active) New England Real Estate Network #4466187 | $299,000 |
| 11/02/2015 | Expired New England Real Estate Network #4407287 | — |
| 03/16/2015 | Listed (Active) New England Real Estate Network #4407287 | $395,000 |
| 06/22/2006 | Expired New England Real Estate Network #804759 | — |
| 05/22/2001 | Listed (Active) New England Real Estate Network #804759 | $275,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 77 Winding Road
Schools near 77 Winding Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 6 |
Rating | School | Distance |
|---|---|---|
Albert Bridge School (West Windsor) PublicPK to 6 |
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.
Similar Homes
New listings in 05037
$255,000
- Unavailable
- Bedrooms
- Unavailable
- Bathrooms
- Unavailable
- Square Feet
- 9.4
- Acres
Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 77 Winding Road, West Windsor, VT 05037 | $525,000 | 4 | 2 | 2,380 | 531,432 |
– | 7 | 4 | 3,497 | 410,335 | |
– | – | – | – | 927,828 | |
$360,000 | 3 | 3 | 2,356 | 405,543 | |
$230,000 | 3 | 3 | 1,400 | 217,800 | |
$116,000 | – | – | – | 235,224 | |
– | 6 | 3 | 2,052 | 579,348 | |
$405,000 | 4 | 2 | 1,800 | 242,193 | |
$945,000 | 6 | 5 | 4,385 | 3,643,794 | |
$250,000 | 3 | 2 | 1,744 | 125,017 | |
$1,000,000 | 4 | 3 | 3,796 | 1,459,260 | |
$1,000,000 | 4 | 3 | 3,298 | 1,459,260 | |
– | 5 | 4.5 | 3,226 | 221,720 | |
– | 4 | 1.5 | 2,288 | 72,745 | |
– | 3 | 2 | 3,031 | 156,380 | |
$165,000 | 3 | 2 | 3,120 | 555,390 |
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of Dark Horse Realty
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 09/07/2026 09:06 PM
