Sold
Last Sold Price
3 beds1,312 sqft
3539 Weatherhead Hollow Rd, Guilford, VT 05301
Single FamilyProperty Type
41.9 acresLot Size
1968Year Built
$164/sq ftPrice per sq ft

Description

What a Guilford Gem! This house sits up high, right off of a paved road. Only one family has lived in this home. The rooms are light-filled with an open concept kitchen/dining and living area. Not only is this a great location but there is a gorgeous pond that a new owner will enjoy every day. Imagine morning coffee looking out onto this amazing picturesque setting. The owners have been making great improvements and renovations this past year. Almost 42 acres in your backyard for hiking, snow shoeing,...What a Guilford Gem! This house sits up high, right off of a paved road. Only one family has lived in this home. The rooms are light-filled with an open concept kitchen/dining and living area. Not only is this a great location but there is a gorgeous pond that a new owner will enjoy every day. Imagine morning coffee looking out onto this amazing picturesque setting. The owners have been making great improvements and renovations this past year. Almost 42 acres in your backyard for hiking, snow shoeing, snowmobiling and future logging potential. At the top of the property is a lovely open meadow lined with Christmas trees. Easy commute to Brattleboro and I91.

    Sold By BHG Masiello Brattleboro

    • Listed by: Kristen Ziter Taylor • Brattleboro Area Realty
    Listing closed: 08/23/2016 12:00 AM • Source: New England Real Estate Network, MLS#: 4494191

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    Recent comparable sales

    Median sold price

    $239,000

    Avg days on market

    60

    Sale-to-list ratio

    91.0%

    Guilford, VT

    9 comparable properties found

    $395,000 | 44 Russell Road, Guilford, VT 05301
    1/35
    1

    $395,000

    Sold 07/24/25

    3
    Bedrooms
    1,440
    Square Feet
    10.4
    Acres
    2

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    Sold 05/06/26

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    Bedrooms
    2
    Bathrooms
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    0.75
    Acres
    3

    $200,000

    Sold 04/11/25

    3
    Bedrooms
    2
    Bathrooms
    2,016
    Square Feet
    8
    Acres
    $239,000 | 21926 Sr 1, Guilford, IN 47022
    1/15
    4

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    Sold 06/23/25

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    3
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    Sold 03/05/25

    3
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    Acres
    $180,000 | 1455 Highway 8, Guilford, NY 13809
    1/2
    6

    $180,000

    Sold 01/07/25

    3
    Bedrooms
    1,421
    Square Feet
    0.9
    Acres
    $260,000 | 196 Randall Drive, Guilford, VT 05301
    1/32
    7

    $260,000

    Sold 10/22/24

    3
    Bedrooms
    1,335
    Square Feet
    3.4
    Acres
    $287,000 | 63 Guilford Center Road, Guilford, ME 04443
    1/34
    8

    $287,000

    Sold 08/14/26

    3
    Bedrooms
    1,400
    Square Feet
    2.4
    Acres
    $798,219 | 1736 River Road, Guilford, VT 05301
    1/32
    9

    $798,219

    Sold 06/17/26

    3
    Bedrooms
    2,300
    Square Feet
    13.63
    Acres

    Location

    Add your commute

    Payment Calculator

    $1,470 per month

    30 year fixed, 7.03% Interest

    Principal and Interest

    $1,148

    Property Taxes

    $322

    HOA Dues

    $0

    The Payment Calculator is for illustrative purposes only.

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    Property Information for 3539 Weatherhead Hollow Road

    Property Details
    • Taxes: $3,868 / year
    • MLS Type: Residential / Single Family
    • Parking: Driveway
    • Water Body Type: Pond
    • Zoning: none
    Building Information
    • Stories: 2
    • Year Built: 1968
    • Lot Size: 41.90 AC / 1,825,164 SF
    Summary
    Location and General Information
    • Area Description: Rural
    • City: Guilford
    • County: VT-Windham
    • Directions: From Weatherhead Hollow Rd go 3.5 miles, house on left immediately after Indigo Drive, see sign
    • Latitude: 42.751647984605
    • Longitude: -72.608694951412
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip: 05301
    Taxes and HOA Information
    • SPAN Number: 27308610126
    • Tax - Gross Amount: $3,868.32
    • Tax Year: 2015
    • Taxes TBD: No
    School Information
    • School - High: Brattleboro High School
    • School - Elementary: Guilford Central School
    • School - Middle/Jr: Guilford Central School
    Parking
    • Garage: No
    • Garage Capacity: .00
    • Driveway: Dirt, Gravel
    Property
    Lot Information
    • Lot - Sqft: 1825164.0
    • Lot Size Acres: 41.9
    • Road Frontage Length: 1400.0
    • Square Feet Apx Finished Above Grade: 1312.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Finished BG Source: Public Records
    • Square Feet Apx Tot Below Grade: 832.0
    • Square Feet Apx Total Finished: 1312.0
    • Square Feet Apx Unfinished Below Grade: 832.0
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete
    • Surveyed: Unknown
    • Year Built: 1968
    Utilities
    • Electric: 100 Amp
    • Sewer: 1000 Gallon, Leach Field, Septic
    Interior and Exterior Features
    Exterior Features
    • Color: white
    • Features - Exterior: Deck, Porch, Porch - Screened
    • Roads: Public
    • Roof: Shingle - Asphalt
    Interior Features
    • Appliances: Cooktop - Electric, Dryer, Refrigerator, Washer
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Concrete, Full, Unfinished
    • Baths - Total: 2
    • Baths - Full: 2
    • Half Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 7
    • Bedrooms - Total: 3
    • Features - Interior: Dining Area, Fireplaces - 1
    • Flooring: Hardwood, Laminate, Tile, Vinyl
    • Heat Fuel: Gas - LP/Bottle
    • Heating: Baseboard
    • Total Stories: 2
    Room Information
    Room 1
    • Room Dimensions: 10x20.6
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 7.6x15
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 13x15
    • Room Level: 1
    • Room Type: Living Room
    Room 7
    • Room Dimensions: 10x14.6
    • Room Level: 2
    • Room Type: Master Bedroom
    Room 8
    • Room Dimensions: 9x10.3
    • Room Level: 1
    • Room Type: Bedroom
    Room 9
    • Room Dimensions: 9.6x10
    • Room Level: 2
    • Room Type: Bedroom
    Room 12
    • Room Dimensions: 10x10
    • Room Level: 1
    • Room Type: Den
    Room 13
    • Room Dimensions: 5.6x8
    • Room Level: 1
    • Room Type: Other
    Room 14
    • Room Dimensions: 5x8.6
    • Room Level: 2
    • Room Type: Other

    Property History for 3539 Weatherhead Hollow Road

    DateEvent & SourcePriceAppreciation
    Aug 23, 2016

    Sold

    New England Real Estate Network #4494191

    $215,000—
    Aug 22, 2016

    Sold (Public Record)

    Public Record #589920756

    $215,000—
    Aug 10, 2016

    Pending

    New England Real Estate Network #4494191

    —
    DateEvent & SourcePrice
    08/23/2016

    Sold

    New England Real Estate Network #4494191

    $215,000
    08/22/2016

    Sold (Public Record)

    Public Record #589920756

    $215,000
    08/10/2016

    Pending

    New England Real Estate Network #4494191

    —

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

    Public Records for 3539 Weatherhead Hollow Road

    Taxable ValueLand-Additions-Total-
    Tax Record2025$4,288 ($357 / month)
    Home Facts
    Beds3Baths2Total Finished SqFt1,456 SqFtAbove Grade Finished SqFt1,456 SqFtStories2Lot Size1,825,164 SqFtStyleSingle Family ResidenceYear Built1968Year Renovated1968ZoningVRCountyWINDHAMAPN(086) 796

    Schools near 3539 Weatherhead Hollow Road

    This home is within Windham Southeast Unified Union School District #96.
    Rating
    School
    Type
    Grades
    Distance
    Public - PK to 6
    Public - 9 to 12
    Public - 9 to 12
    Public - PK to 6
    Rating
    School
    Distance
    Guilford Central School
    PublicPK to 6

    Brattleboro Senior Uhsd #6
    Public9 to 12

    Windham Regional Career Center
    Public9 to 12

    Canal Street/Oak Grove Schools
    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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    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 3539 Weatherhead Hollow Road, Guilford, VT 05301
    $215,000
    3
    1,312
    1,825,164
    –
    3
    1
    1,092
    2,761,704
    –
    –
    –
    –
    618,552
    –
    7
    4
    4,068
    4,159,109
    $212,000
    3
    1,257
    174,240
    $190,000
    4
    2
    1,801
    230,868

    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 Brattleboro Area 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 09/28/2026 03:01 AM