77 Winding Rd

West Windsor, VT 05037

$525,000
Last Sold Price
4
Beds
2,380 Sq. Ft.
$221 / Sq. Ft.
2,380
Sq. Ft.
$221
per Sq. Ft.
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Closed 12/15/25
Closed 12/15/25

Description

Light and thoughtful architect designed home on a lovely 12 acre hilltop. Set in a magical landscape of exposed ledge, old stone walls & established perennial gardens. Stunning views of both Mt Ascutney and Little Ascutney. Spacious and airy, large windows and south-facing skylights provide passive solar warmth throughout the 4 bedroom home. Open layout is clean and efficient with cathedral ceilings & custom touches. Drilled well. The kitchen has smart, functional design. Dining/Family room and sunken...Light and thoughtful architect designed home on a lovely 12 acre hilltop. Set in a magical landscape of exposed ledge, old stone walls & established perennial gardens. Stunning views of both Mt Ascutney and Little Ascutney. Spacious and airy, large windows and south-facing skylights provide passive solar warmth throughout the 4 bedroom home. Open layout is clean and efficient with cathedral ceilings & custom touches. Drilled well. The kitchen has smart, functional design. Dining/Family room and sunken living room. Large primary bedroom with ensuite bath, laundry, and deck. A perfect spot for anyone who enjoys the outdoors. Direct access to recreational trails. Close to Ascutney Outdoors, WW Town Forest & the Brownsville Butcher & Pantry. A peaceful homestead in a truly special corner of Vermont. Listing price adjusted to reflect older roof, decks & skylights. All still serviceable.
  1. Listed by Dana Waters • Dark Horse Realty
  2. Listed by Paula Waters • Dark Horse Realty

Sold By BHG Masiello Brattleboro

Property Details for 77 Winding Road

Zoning
Res
LISTING CLOSED: 12/15/2025 12:00 AM

Property Details for 77 Winding Road

StatusClosed
MLS #5064038
Days on Market24
Taxes$8,338 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1988
Lot Size12.20 AC / 531,432 SF
CountyWindsor County
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Location

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Building Information for 77 Winding Road

Stories2Year Built1988Building Size-Lot Size12.20 AC / 531,432 SF

Payment Calculator

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$3,363 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,669

Property Taxes

$695

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 77 Winding Road

Summary
Location and General Information
  • 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
Taxes and HOA Information
  • SPAN Number: 738-235-10591
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Gravel, Other, Right-Of-Way (ROW)
Property
Lot Information
  • 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
Property and Assessments
  • Current Use: No
  • Assessment Amount: $522,000
  • Assessment Year: 2024
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • 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
Utilities
  • 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
Interior and Exterior Features
Exterior Features
  • Color: Brown
  • Construction Materials: Wood Frame, Clapboard Exterior
  • Roof: Asphalt Shingle
Interior Features
  • 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

DateEvent & SourcePriceAppreciation
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

—
DateEvent & SourcePrice
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

—

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

Public Records for 77 Winding Road

Taxable ValueLand$180,500Additions$341,500Total$522,000
Tax Record2021$7,663 ($639 / month)
Home Facts
Beds4Total Finished SqFt2,180 SqFtAbove Grade Finished SqFt2,180 SqFtStories2Lot Size531,432 SqFtStyleSingle Family ResidenceYear Built1988CountyWINDSORAPN(235) 02-052

Schools near 77 Winding Road

This home is within Mount Ascutney School District #86.
Rating
School
Type
Grades
Distance
Albert Bridge School (West Windsor)
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.

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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 07/24/2026 03:01 PM