Sold
Last Sold Price
3 beds1,700 sqft$126/sqft
14 Deep Woods Rd, Winhall, VT 05255
Single FamilyProperty Type
1.2 acresLot Size
1978Year Built
$126/sq ftPrice per sq ft

Description

Charming updated "country " style chalet. Lovely wide board pine floors. Wood burning fireplace in upper living room with pellet stove in family room fireplace. 3 bedrooms, 2 fulls baths and "crows nest" loft. Privately sited on a 1+ acre lot - located close to both Manchester and skiing. Suitable for a primary or second home.Charming updated "country " style chalet. Lovely wide board pine floors. Wood burning fireplace in upper living room with pellet stove in family room fireplace. 3 bedrooms, 2 fulls baths and "crows nest" loft. Privately sited on a 1+ acre lot - located close to both Manchester and skiing. Suitable for a primary or second home.

    Sold By Four Seasons Sotheby's Int'l Realty

    • Listed by: Betsy Cetron • Stratton Real Estate
    Listing closed: 12/07/2018 12:00 AM • Source: New England Real Estate Network, MLS#: 4676944

    Recent comparable sales

    Median sold price

    $565,000

    Avg days on market

    33

    Sale-to-list ratio

    94.2%

    Winhall, VT

    9 comparable properties found

    $580,000 | 20 Deep Woods Circle, Winhall, VT 05255
    1/36
    1

    $580,000

    Sold 10/21/24

    3
    Bedrooms
    1,592
    Square Feet
    2.17
    Acres
    $565,000 | 5 Vermont Haunts Road, Winhall, VT 05255
    1/40
    2

    $565,000

    Sold 09/30/24

    2
    Bedrooms
    1,910
    Square Feet
    2
    Acres
    $340,000 | 8 Winhall Woods Road, Winhall, VT 05340
    1/28
    3

    $340,000

    Sold 03/11/26

    3
    Bedrooms
    1,144
    Square Feet
    1.2
    Acres
    $560,000 | 35 Glendon Hills Road, Winhall, VT 05340
    1/33
    4

    $560,000

    Sold 09/26/25

    3
    Bedrooms
    1,400
    Square Feet
    1
    Acres
    $580,000 | 39 Todd Hill Road, Winhall, VT 05340
    1/34
    5

    $580,000

    Sold 10/26/24

    3
    Bedrooms
    1,484
    Square Feet
    1.3
    Acres
    $565,000 | 4 Pearl Buck Drive, Winhall, VT 05340
    1/35
    6

    $565,000

    Sold 06/18/26

    3
    Bedrooms
    1,455
    Square Feet
    2.01
    Acres
    $725,000 | 11 Todd Hill Road, Winhall, VT 05340
    1/37
    7

    $725,000

    Sold 01/03/25

    3
    Bedrooms
    1,800
    Square Feet
    0.9
    Acres
    $430,000 | 13 Lower Taylor Hill Road, Winhall, VT 05340
    1/25
    8

    $430,000

    Sold 03/26/25

    3
    Bedrooms
    1,716
    Square Feet
    0.56
    Acres
    $615,000 | 29 Burnt Hill Road, Winhall, VT 05340
    1/38
    9

    $615,000

    Sold 04/15/25

    3
    Bedrooms
    1,500
    Square Feet
    1.09
    Acres

    Location

    Add your commute

    Payment Calculator

    $1,394 per month

    30 year fixed, 6.55% Interest

    Principal and Interest

    $1,093

    Property Taxes

    $301

    HOA Dues

    $0

    The Payment Calculator is for illustrative purposes only.

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    Property Information for 14 Deep Woods Road

    Property Details
    • Taxes: $3,615 / year
    • MLS Type: Residential / Single Family
    • Zoning: res
    Building Information
    • Stories: 2
    • Year Built: 1978
    • Lot Size: 1.20 AC / 52,272 SF
    Summary
    Location and General Information
    • City: Winhall
    • County: VT-Bennington
    • Directions: Second house on right on Deepwoods Road -- Long Driveway -- Number out front
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip: 05340
    Taxes and HOA Information
    • SPAN Number: 77112451177
    • Tax - Gross Amount: $3,615.00
    • Tax Year: 2018
    • Taxes TBD: No
    School Information
    • School - High: Choice
    • School - District: Bennington/Rutland
    • School - Elementary: Choice
    • School - Middle/Jr: Choice
    Parking
    • Garage: No
    • Driveway: Gravel
    Property
    Lot Information
    • Lot - Sqft: 52272.0
    • Lot Size Acres: 1.2
    • Road Frontage Length: 200.0
    • Square Feet Apx Finished Above Grade: 1700.0
    • 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: 1700.0
    • Square Feet Apx Total Finished: 1700.0
    • 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
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete
    • PreConstruction: No
    • Surveyed: Unknown
    • Year Built: 1978
    Utilities
    • Cable Company: Comcast
    • Electric: 220 Plug
    • Sewer: Septic
    • Utilities: Cable, Cable - At Site, Internet - Cable
    Interior and Exterior Features
    Exterior Features
    • Color: brown
    • Features - Exterior: Deck, Window Screens, Windows - Double Pane, Windows - Energy Star
    • Roads: Gravel, Public
    • Roof: Shingle - Asphalt
    Interior Features
    • Appliances: Dishwasher, Dryer, Exhaust Hood, Range - Gas, Refrigerator, Washer
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Crawl Space
    • Baths - Total: 2
    • Baths - Full: 2
    • Half Baths: 0
    • One Quarter Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 7
    • Rooms: Level 1: Level 1: Bedroom, Level 1: Family Room, Level 1: Mudroom
    • Rooms: Level 2: Level 2: Dining Room, Level 2: Kitchen, Level 2: Living Room, Level 2: Master Bedroom
    • Rooms: Level 3: Level 3: Loft
    • Bedrooms - Total: 3
    • Equipment: Air Conditioner, Smoke Detectr-Batt Powrd
    • Features - Interior: Cathedral Ceiling, Dining Area, Fireplace - Screens/Equip, Fireplace - Wood, Fireplaces - 2, Living/Dining, Wood Stove Insert, Laundry - 1st Floor
    • Flooring: Softwood, Tile, Vinyl
    • Heat Fuel: Kerosene, Oil
    • Heating: Forced Air
    • Cooling: Wall AC Units
    • Total Stories: 2
    Room Information
    Room 1
    • Room Dimensions: 14 x 14
    • Room Level: 2
    • Room Type: Living Room
    Room 2
    • Room Dimensions: 14x 14
    • Room Level: 2
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 14 x 10
    • Room Level: 2
    • Room Type: Kitchen
    Room 4
    • Room Dimensions: 14 x 16
    • Room Level: 2
    • Room Type: Master Bedroom
    Room 5
    • Room Dimensions: 12 x 24
    • Room Level: 1
    • Room Type: Family Room
    Room 6
    • Room Dimensions: 10 x 14
    • Room Level: 1
    • Room Type: Bedroom
    Room 7
    • Room Dimensions: 14 x 10
    • Room Level: 1
    • Room Type: Bedroom
    Room 8
    • Room Dimensions: 8 x8
    • Room Level: 1
    • Room Type: Mudroom
    Room 9
    • Room Dimensions: 10 x 14
    • Room Level: 3
    • Room Type: Loft

    Property History for 14 Deep Woods Road

    DateEvent & SourcePriceAppreciation
    Dec 20, 2018

    Sold (Public Record)

    Public Record #637323593

    $215,000
    Dec 7, 2018

    Sold

    New England Real Estate Network #4676944

    $215,000
    Dec 7, 2018

    Pending

    New England Real Estate Network #4676944

    DateEvent & SourcePrice
    12/20/2018

    Sold (Public Record)

    Public Record #637323593

    $215,000
    12/07/2018

    Sold

    New England Real Estate Network #4676944

    $215,000
    12/07/2018

    Pending

    New England Real Estate Network #4676944

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

    Public Records for 14 Deep Woods Road

    Taxable ValueLand$63,000Additions$138,400Total$201,400
    Tax Record2025$3,700 ($308 / month)
    Home Facts
    Beds3Baths2Total Finished SqFt1,456 SqFtAbove Grade Finished SqFt1,456 SqFtStories1Lot Size52,272 SqFtStyleSingle Family ResidenceYear Built1975Year Renovated1975CountyBENNINGTONAPN(245)84047

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    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 14 Deep Woods Road, Winhall, VT 05255
    $215,000
    3
    1,700
    52,272
    $55,000
    47,916
    $26,000
    47,916
    $105,000
    3
    1,116
    43,560
    $105,000
    3
    986
    43,560
    $105,000
    3
    1,250
    60,984

    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 Stratton Real Estate

    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 08:11 PM