97-99 Darling Road

Closed 9/30/20
Closed 9/30/20
Gallery Image 1
Sold
Last Sold Price
$1,500,000
5 beds4,749 sqft
97-99 Darling Rd, South Woodstock, VT 05071
Single FamilyProperty Type
75.5 acresLot Size
1962Year Built
$316/sq ftPrice per sq ft
4 carsParking Spaces

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.

    Sold By Wade I Treadway Real Estate

    • Listed by: T Story Jenks • LandVest, Inc/Woodstock
    • Listed by: Dia Jenks • LandVest, Inc/Woodstock
    Listing closed: 09/30/2020 12:00 AM • Source: New England Real Estate Network, MLS#: 4767586

    Recent comparable sales

    Median sold price

    $410,000

    Avg days on market

    455

    Sale-to-list ratio

    79.7%

    South Woodstock, VT

    3 comparable properties found

    $2,750,000 | 318 Ebbin Lockwood Way, South Woodstock, VT 05071
    1/41
    1

    $2,750,000

    Sold 02/13/25

    3
    Bedrooms
    6,443
    Square Feet
    54.83
    Acres

    318 Ebbin Lockwood Way, South Woodstock, VT 05071

    2

    $117,933

    Sold 10/04/24

    4
    Bedrooms
    2.5
    Bathrooms
    2,088
    Square Feet
    3.47
    Acres

    6012 S Road, South Woodstock, VT 05071

    3

    $410,000

    Sold 10/11/24

    3
    Bedrooms
    2
    Bathrooms
    2,030
    Square Feet
    Unavailable
    Acres

    148 Hall Circle, Unit A, South Woodstock, VT 05071

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    Property Information for 97-99 Darling Road

    Property Details
    • Taxes: $18,662 / year
    • MLS Type: Residential / Single Family
    • County: Windsor County
    • Zoning: Res
    Building Information
    • Stories: 2
    • Year Built: 1962
    • Lot Size: 75.50 AC / 3,288,780 SF
    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
    • 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
    1.5
    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 09/16/2026 05:57 AM