97-99 Darling Road

Closed 9/30/20
Closed 9/30/20
Gallery Image 1
Last Sold Price
$1,500,000
5 beds4,749 sqft$316/sqft
97-99 Darling Rd, South Woodstock, VT 05071

Description

High Riding’s 75.5 acres with panoramic views from Mt. Ascutney to Mt. Washington comprise one of the most beautiful land parcels in Woodstock and includes two separate residences, two garages and stables. Architect Harvey Stevenson’s (NYC Mayor Fiorello LaGuardia’s “chief architect”) 1962 modern design at 99 Darling Road embraces the striking layered views of meadow, near hillsides, and distant mountains. The 2,365 square-foot interior OF 99 blends Japanese-style simplicity with Vermont provenance,...High Riding’s 75.5 acres with panoramic views from Mt. Ascutney to Mt. Washington comprise one of the most beautiful land parcels in Woodstock and includes two separate residences, two garages and stables. Architect Harvey Stevenson’s (NYC Mayor Fiorello LaGuardia’s “chief architect”) 1962 modern design at 99 Darling Road embraces the striking layered views of meadow, near hillsides, and distant mountains. The 2,365 square-foot interior OF 99 blends Japanese-style simplicity with Vermont provenance, such as curved walls of a honey-colored butternut veneer, curly maple on the stairs, and birds-eye maple on the kitchen cabinets. The large main level master bedroom is paired with two additional bedrooms on the garden level, which opens to a covered patio. A detached two-car garage is conveniently accessible. The “Studio” at 97 Darling Road, a 2,384 square-foot separate building, has a 2-bay garage, 3 offices (or living) areas on the first level, and a completely equipped two-bedroom guest apartment above with lovely North light and near and long-range views. A private deck leads down to the stone patio. The landscape combines birch and maple glades with mature specimen trees of many varieties in a park-like setting, naturalistic plantings, perennial gardens and dramatic stone steps leading down to a swimming pond. There are over 800 sugar maples- tapped for maple syrup, apple trees, well maintained pastures, forest, private riding and hiking trails and a 3-stall stable.
LISTING CLOSED: 09/30/2020 12:00 AM

  1. Listed by T Story Jenks • LandVest, Inc/Woodstock
  2. Listed by Dia Jenks • LandVest, Inc/Woodstock

Sold By Wade I Treadway Real Estate

Property Details for 97-99 Darling Road

Status
Closed
MLS #
4767586
Days on Market
291
Taxes
$18,662 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential / Single Family
Year Built
1962
Lot Size
75.50 AC / 3,288,780 SF
County
Windsor County
Zoning
Res
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Building Information for 97-99 Darling Road

Stories2Year Built1962Building Size-Lot Size75.50 AC / 3,288,780 SF

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Principal and Interest

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Property Information for 97-99 Darling Road

Summary
Location and General Information
  • City: Woodstock
  • County: VT-Windsor
  • Latitude: 43.563475552552056
  • Longitude: -72.574846238098075
  • Road Frontage: TBD
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip: 05071
Taxes and HOA Information
  • SPAN Number: 786-250-11064
  • Tax - Gross Amount: $18,661.62
  • Tax Year: 2018
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 4.00
  • Driveway: Gravel
Virtual Tour
Property
Lot Information
  • Lot - Sqft: 3288780.0
  • Lot Size Acres: 75.5
  • Square Feet Apx Finished Above Grade: 4749.0
  • Square Feet Apx Finished AG Source: Other
  • Square Feet Apx Finished Below Grade: 0.0
  • Square Feet Apx Finished BG Source: Other
  • Square Feet Apx Total: 4749.0
  • Square Feet Apx Total Finished: 4749.0
  • Square Feet Apx Unfinished Above Grade: 0.0
  • Square Feet Apx Unfinished AG Source: Other
  • Square Feet Apx Unfinished Below Grade: 0.0
  • Square Feet Apx Unfinished BG Source: Other
Property and Assessments
  • Current Use: Yes
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: Unknown
  • Foundation: Concrete
  • PreConstruction: No
  • Surveyed: Yes
  • Year Built: 1962
Utilities
  • Electric Company: Green Mountain Power
  • Fuel Company: Dead River
  • Electric: Circuit Breaker(s)
  • Sewer: Private
  • Utilities: DSL, Multi Phone Lines, Satellite, Telephone Available, Underground Utilities
Interior and Exterior Features
Exterior Features
  • Features - Exterior: Deck, Guest House, Patio, Porch, Stable(s)
  • Roads: Public
  • Roof: Membrane
Interior Features
  • Appliances: Cooktop - Gas, Dishwasher, Dryer, Exhaust Hood, Microwave, Oven - Double, Refrigerator, Trash Compactor, Washer, Wine Cooler
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Concrete Floor, Daylight, Finished, Full, Stairs - Interior, Storage Space, Walkout, Exterior Access
  • Baths - Total: 5
  • Baths - Full: 3
  • Half Baths: 1
  • One Quarter Baths: 0
  • Three Quarter Bath: 1
  • Rooms - Total: 14
  • Bedrooms - Total: 5
  • Equipment: Dehumidifier, Satellite Dish, Security System, Smoke Detector, Generator - Standby
  • Features - Interior: Blinds, Dining Area, Fireplace - Wood, Master BR w/ BA, Natural Light, Natural Woodwork, Wood Stove Hook-up
  • Flooring: Carpet, Hardwood, Slate/Stone
  • Heat Fuel: Electric, Gas - LP/Bottle, Oil
  • Heating: Baseboard, Forced Air, Radiator
  • Cooling: Mini Split
  • Total Stories: 2

Property History for 97-99 Darling Road

DateEvent & SourcePriceAppreciation
Sep 30, 2020

Sold

New England Real Estate Network #4767586

$1,500,000—
May 15, 2020

Pending

New England Real Estate Network #4767586

—
Jul 29, 2019

Listed (Active)

New England Real Estate Network #4767586

$1,575,000—
DateEvent & SourcePrice
09/30/2020

Sold

New England Real Estate Network #4767586

$1,500,000
05/15/2020

Pending

New England Real Estate Network #4767586

—
07/29/2019

Listed (Active)

New England Real Estate Network #4767586

$1,575,000

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

Schools near 97-99 Darling Road

This home is within Windsor Central Unified Union School District.
Rating
School
Type
Grades
Distance
Woodstock Elementary School
Public - PK to 6
Woodstock Senior Uhsd #4
Public - 7 to 12
Rating
School
Distance
Woodstock Elementary School
PublicPK to 6

Woodstock Senior Uhsd #4
Public7 to 12

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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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 97-99 Darling Road, South Woodstock, VT 05071
$1,500,000
5
4,749
3,288,780
99 Darling Road, South Woodstock, VT 05071
$1,500,000
2
2
2,384
3,288,780
232 Darling Road, South Woodstock, VT 05071
–
–
–
–
1,345,133
12107 Long Hill Road, Woodstock, VT 05071
$287,500
4
–
56,628
1384 Long Hill Road, Woodstock, VT 05071
–
4
2
2,228
239,580
12108 Long Hill Road, Woodstock, VT 05071
$210,000
3
–
618,552

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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. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of LandVest, Inc/Woodstock

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 08/05/2026 01:11 AM