66 Upper Oak Hill Rd

Newfane, VT 05362

$579,000
Price
4
Beds
1,723 Sq. Ft.
$336 / Sq. Ft.
1,723
Sq. Ft.
$336
per Sq. Ft.
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Active Under Contract
Active Under Contract

Description

180° +/- views, end of the road, top of the hill privacy. 12 acres,4 beds,2 baths,brick,beams,built-ins,custom features,screen room, bonus space! A combination increasingly difficult to find, especially minutes from Newfane Village, Rock River, Brattleboro, vibrant arts community, farm-to-table dining, local galleries, garden shops, farm markets, outdoor recreation that define this special corner of Southern Vermont. Tucked away,this 4 bed, 2 bath Gambrel-style home offers the kind of privacy that...180° +/- views, end of the road, top of the hill privacy. 12 acres,4 beds,2 baths,brick,beams,built-ins,custom features,screen room, bonus space! A combination increasingly difficult to find, especially minutes from Newfane Village, Rock River, Brattleboro, vibrant arts community, farm-to-table dining, local galleries, garden shops, farm markets, outdoor recreation that define this special corner of Southern Vermont. Tucked away,this 4 bed, 2 bath Gambrel-style home offers the kind of privacy that has become a luxury in its own right w/wooded & open land, rock gardens, panoramic mountain views,room to explore, relax, or simply enjoy the peace & quiet. With more clearing, the already impressive views offer the opportunity to become even more expansive. Whether you're looking for a full-time Vermont home, weekend retreat, place to work remotely while surrounded by nature, this property offers remarkable flexibility. Enjoy your morning coffee overlooking the mountains, spend the afternoon exploring your land, or gather w/friends in the screened gazebo while watching the sunset. Inside, beams,window seat, custom built-ins & a striking brick accent wall create inviting spaces filled w/warmth & character. Spacious kitchen open to dining room, formal and mudroom entries, full laundry, easily accessible mechanicals. Four bedrooms PLUS multiple flexible bonus spaces provide exceptional versatility for a home office, studio, library, fitness room, guest overflow. Whole-house generator, Wi-Fi & reliable cell service provide modern convenience, while additional utility buildings offer abundant storage, workshop space & room for outdoor gear, equipment or hobbies. Private yet close enough to everything that makes Newfane one of Southern Vermont's most beloved villages. Spend the afternoon at the Rock River, explore galleries, garden shops, linger over farm-to-table dining, hike, or enjoy a night out in Brattleboro before returning home to the rare luxury of complete privacy.
  1. Listed by Jacki Murano • Southern Vermont Realty Group

Property Details for 66 Upper Oak Hill Road

Zoning
Newfane
LISTING UPDATED: 07/23/2026 09:12 PM

Property Details for 66 Upper Oak Hill Road

StatusActive Under Contract
MLS #5100634
Days on Market5
Taxes$7,205 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1987
Lot Size12.00 AC / 522,720 SF
CountyWindham County
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Location

Listing Courtesy of Southern Vermont Realty Group
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Building Information for 66 Upper Oak Hill Road

Stories2Year Built1987Building Size-Lot Size12.00 AC / 522,720 SF

Payment Calculator

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$3,543 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,943

Property Taxes

$600

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 66 Upper Oak Hill Road

Summary
Location and General Information
  • City: Newfane
  • County: VT-Windham
  • Directions: APPOINTMENT ONLY. DO NOT USE GPS-unreliable to this address. Directions will be sent with the confirmed showing/viewing appointment. End of road, no drive-bys. Cameras on site.
  • Latitude: 42.944504621060275
  • Longitude: -72.696965547943108
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05345
Taxes and HOA Information
  • SPAN Number: 429-134-11257
  • Tax Year: 2025
  • Taxes TBD: Yes
Parking
  • Garage: No
  • Driveway: Gravel
Property
Lot Information
  • Lot Features: Open, View, Wooded, Private
  • Lot Size Acres: 12.0
  • Road Frontage Length: 658.0
  • Total Finished Area: 1723.0
  • Above Grade Finished Area: 1723.0
  • Above Grade Finished Area Source: Public Records
  • Above Grade Unfinished Area: 400.0
  • AboveGradeUnfinishedAreaSource: Estimated
  • Below Grade Finished Area: 0.0
  • Below Grade Unfinished Area: 0.0
  • Lot Size Square Feet: 522720.0
  • Total Area: 2123.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1987
Utilities
  • Electric: Circuit Breaker(s)
  • Sewer: On-Site Septic Exists
  • Water Source: Drilled Well
  • Utilities: Phone
  • Internet: Cable Internet
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame
  • Roof: Corrugated, Metal, Shingle
Interior Features
  • Basement: No
  • Basement Description: Crawl Space
  • Heating: Oil, Baseboard
  • Cooling: None
  • Total Stories: 2
  • Rooms Total: 4
  • Bathrooms Full: 1
  • Bathrooms Half: 0
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 1
  • Bedrooms Total: 4
  • Bathrooms Total: 2

Property History for 66 Upper Oak Hill Road

DateEvent & SourcePriceAppreciation
Jul 23, 2026

Active Under Contract

New England Real Estate Network #5100634

—
Jul 18, 2026

Listed (Active)

New England Real Estate Network #5100634

$579,000—
DateEvent & SourcePrice
07/23/2026

Active Under Contract

New England Real Estate Network #5100634

—
07/18/2026

Listed (Active)

New England Real Estate Network #5100634

$579,000

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

Schools near 66 Upper Oak Hill Road

This home is within West River Valley Modified Union Education District #72a.
Rating
School
Type
Grades
Distance
Newbrook Elementary School
Public - PK to 5
Leland & Gray Uhsd #34
Public - 6 to 12
Rating
School
Distance
Newbrook Elementary School
PublicPK to 5

Leland & Gray Uhsd #34
Public6 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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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 Southern Vermont Realty Group

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 08/01/2026 08:24 PM