Sold
Last Sold Price
5 beds4,800 sqft
314 Prosper Rd, Woodstock, VT 05091
Single FamilyProperty Type
22.44 acresLot Size
1996Year Built
$363/sq ftPrice per sq ft
2 carsParking Spaces

Description

A wonderful Colonial-style residence & one of Woodstock's finest homes sited across from the National Park. Historic restored antique structural elements artfully combined with modern mechanical systems create a 21st Century house with 18th Century appeal. 10'ceilings- Classic moldings;Spring-fed Pond; great views! A remarkable country retreat.A wonderful Colonial-style residence & one of Woodstock's finest homes sited across from the National Park. Historic restored antique structural elements artfully combined with modern mechanical systems create a 21st Century house with 18th Century appeal. 10'ceilings- Classic moldings;Spring-fed Pond; great views! A remarkable country retreat.

    Sold By Williamson Group Sothebys Intl. Realty

    • Listed by: Laird Bradley • Williamson Group Sothebys Intl. Realty
    Listing closed: 10/30/2009 12:00 AM • Source: New England Real Estate Network, MLS#: 2731100

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    Recent comparable sales

    Median sold price

    $1,650,000

    Avg days on market

    112

    Sale-to-list ratio

    89.8%

    Woodstock, VT

    9 comparable properties found

    $1,650,000 | 10 College Hill Road, Woodstock, VT 05091
    1/36
    1

    $1,650,000

    Sold 11/24/25

    5
    Bedrooms
    4,214
    Square Feet
    1.07
    Acres
    $2,220,000 | 1059 Carlton Hill Road, Woodstock, VT 05091
    1/51
    2

    $2,220,000

    Sold 11/24/25

    5
    Bedrooms
    4,832
    Square Feet
    2.64
    Acres
    $2,350,000 | 182 Rose Hill Road, Woodstock, VT 05091
    1/37
    3

    $2,350,000

    Sold 10/11/24

    5
    Bedrooms
    3,925
    Square Feet
    1.12
    Acres
    $1,800,000 | 484 Carlton Hill Road, Woodstock, VT 05091
    1/37
    4

    $1,800,000

    Sold 05/23/25

    4
    Bedrooms
    4,100
    Square Feet
    7.66
    Acres
    $1,075,000 | 119 English Mills Way, Woodstock, VT 05091
    1/42
    5

    $1,075,000

    Sold 07/15/25

    5
    Bedrooms
    4,698
    Square Feet
    5.1
    Acres
    $1,580,000 | 33 River Street, Woodstock, VT 05091
    1/43
    6

    $1,580,000

    Sold 12/30/24

    4
    Bedrooms
    4,378
    Square Feet
    0.47
    Acres
    $775,000 | 3961 Hartland Hill Road, Woodstock, VT 05091
    1/59
    7

    $775,000

    Sold 05/11/26

    5
    Bedrooms
    3,886
    Square Feet
    2.36
    Acres
    $2,425,000 | 739 Westerdale Road, Woodstock, VT 05091
    1/41
    8

    $2,425,000

    Sold 08/15/25

    4
    Bedrooms
    5,017
    Square Feet
    10.86
    Acres
    $900,000 | 19 Church Street, Woodstock, VT 05091
    1/28
    9

    $900,000

    Sold 10/17/25

    5
    Bedrooms
    3,486
    Square Feet
    0.2
    Acres

    Location

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    Payment Calculator

    $11,062 per month

    30 year fixed, 7.03% Interest

    Principal and Interest

    $9,294

    Property Taxes

    $1,768

    HOA Dues

    $0

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    Property Information for 314 Prosper Road

    Property Details
    • Taxes: $21,217 / year
    • MLS Type: Residential / Single Family
    • Parking: Parking Spaces 2
    • Water View: Yes
    • Zoning: RD 5
    Building Information
    • Stories: 2
    • Year Built: 1996
    • Lot Size: 22.44 AC / 977,486 SF
    Summary
    Location and General Information
    • Area Description: Abuts Conservation, Mountain, Valley
    • City: Woodstock
    • County: VT-Windsor
    • Directions: Route 12 North from Woodstock Village approximately 3 miles to left on Prosper Road. Go 1 mile+/- to 314 Prosper Road on right (northerly side).
    • Seasonal: No
    • State: VT
    • Map: 03
    • Zip: 05091
    Taxes and HOA Information
    • Tax - Gross Amount: $21,216.52
    • Tax Year: 2008
    • Taxes TBD: No
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Crushed Stone
    Property
    Lot Information
    • Lot: 02-24
    • Lot - Sqft: 977486.0
    • Lot Size Acres: 22.44
    • Square Feet Apx Finished Above Grade: 4800.0
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Total Finished: 4800.0
    Property and Assessments
    • Current Use: No
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete
    • Surveyed: Yes
    • Year Built: 1996
    Utilities
    • Electric: 200 Amp, Circuit Breaker(s)
    • Sewer: 1000 Gallon, Mound
    • Utilities: Cable, Multi Phone Lines, Underground Utilities
    Interior and Exterior Features
    Exterior Features
    • Features - Accessibility: 1st Floor Full Bathroom, Access Common Use Areas, Access Mailboxes No Steps, Access Parking, Bathroom w/Tub, Kitchen w/5 Ft. Diameter, Zero-Step Entry Ramp
    • Features - Exterior: Barn, Outbuilding, Porch - Screened
    • Roads: Public
    • Roof: Shingle - Asphalt
    Interior Features
    • Appliances: Dishwasher, Dryer, Freezer, Microwave, Mini Fridge, Oven - Wall, Range - Gas, Refrigerator, Washer
    • Basement Description: Full, Partially Finished
    • Baths - Total: 4
    • Baths - Full: 4
    • Half Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 10
    • Bedrooms - Total: 5
    • Equipment: Satellite Dish, Smoke Detector
    • Features - Interior: Ceiling Fan, Dining Area, Fireplace - Wood, Kitchen Island, Master BR w/ BA, Walk-in Pantry, Window Treatment, Laundry - 1st Floor, Laundry - 2nd Floor
    • Heat Fuel: Oil
    • Heating: Hot Air
    • Total Stories: 2
    Room Information
    Room 1
    • Room Dimensions: 16x32
    • Room Type: Kitchen - Eat-in
    Room 2
    • Room Dimensions: 15x15
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 20x20
    • Room Type: Living Room
    Room 4
    • Room Dimensions: 15x20
    • Room Type: Family Room
    Room 5
    • Room Type: Office/Study
    Room 6
    • Room Type: Mudroom
    Room 7
    • Room Dimensions: 18x20
    • Room Level: 1
    • Room Type: Master Bedroom
    Room 8
    • Room Dimensions: 13x15
    • Room Type: Bedroom
    Room 9
    • Room Dimensions: 13x17
    • Room Type: Bedroom
    Room 10
    • Room Dimensions: 12x18
    • Room Type: Bedroom
    Room 11
    • Room Type: Library
    Room 12
    • Room Dimensions: 14x16
    • Room Type: Den
    Room 13
    • Room Dimensions: 26x26
    • Room Type: Other
    Room 14
    • Room Dimensions: 10x26
    • Room Type: Other

    Property History for 314 Prosper Road

    DateEvent & SourcePriceAppreciation
    Oct 30, 2009

    Sold

    New England Real Estate Network #2731100

    $1,741,000—
    Sep 7, 2009

    Pending

    New England Real Estate Network #2731100

    —
    Jul 3, 2008

    Price Change

    New England Real Estate Network #2731100

    $2,100,000—
    DateEvent & SourcePrice
    10/30/2009

    Sold

    New England Real Estate Network #2731100

    $1,741,000
    09/07/2009

    Pending

    New England Real Estate Network #2731100

    —
    07/03/2008

    Price Change

    New England Real Estate Network #2731100

    $2,100,000

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

    Schools near 314 Prosper Road

    This home is within Windsor Central Unified Union School District.
    Rating
    School
    Type
    Grades
    Distance
    Public - PK to 6
    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: 314 Prosper Road, Woodstock, VT 05091
    $1,741,000
    5
    4,800
    977,486
    $1,200,000
    5
    –
    4,454,010
    $720,500
    3
    2,830
    439,956
    –
    –
    –
    1,541
    1,742
    $180,000
    6
    2,704
    10,890
    $120,000
    3
    1,726
    70,131

    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 Williamson Group Sothebys Intl. 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 09/27/2026 11:29 PM