The details, craftsmanship and enchanting +/-9 surveyed acre setting is right out of a fairy tale. A perfect Vermont getaway retreat with the sounds of Oven Brook at your door- complete with foot bridge to your own back meadow where you can take in the views overlooking the gorgeous Kent Hollow setting. The c1865 antique cabin is loaded with character – wide-plank “bow-tie” floors, log doors and stairs, and stone fireplace/wood stove… Simple but perfect with generous living/dining room (FP and sliding door to deck/brook), ample kitchen, bath and two low ceilinged cozy bedrooms upstairs. Amenities include 2007 installed septic, (Artesian) drilled well, oil hot air heat, 100 amp electric, etc
Closed
Listed by:
Scott Mcchesney,
McChesney RE, Inc. 802-325-3100,
Robin Chesnut-Tangerman,
McChesney RE, Inc.
Bought with: BHG Masiello Brattleboro
$300,000
3606 Kent Hollow Road, Rupert, VT 05778
2beds
890sqft
Single Family Residence
Built in 1865
9 Acres Lot
$304,500 Zestimate®
$337/sqft
$2,155 Estimated rent
Home value
$304,500
Estimated sales range
Not available
$2,155/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: October 20, 2025 at 08:59am
Listed by:
Scott Mcchesney,
McChesney RE, Inc. 802-325-3100,
Robin Chesnut-Tangerman,
McChesney RE, Inc.
Bought with:
Monica Sumner
BHG Masiello Brattleboro
Source: PrimeMLS,MLS#: 5061400
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- 3/4 bathrooms: 1
Heating
- Oil, Wood, Hot Air, Wood Stove
Cooling
- None
Appliances
- Included: Gas Range, Refrigerator, Propane Water Heater, Instant Hot Water
Features
- Living/Dining, Natural Woodwork
- Flooring: Wood
- Windows: Screens, Storm Window(s)
- Basement: Crawl Space,Insulated,Partial,Unfinished,Basement Stairs,Walk-Up Access
- Has fireplace: Yes
- Fireplace features: Wood Burning, Wood Stove Insert
Interior area
- Total structure area: 1,140
- Total interior livable area: 890 sqft
- Finished area above ground: 890
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Gravel, Attached
- Garage spaces: 1
Features
- Levels: One and One Half
- Stories: 1
- Exterior features: Deck, Natural Shade
- Waterfront features: Stream, Waterfall
- Body of water: Oven Brook
- Frontage length: Road frontage: 610
Lot
- Size: 9 Acres
- Features: Country Setting, Field/Pasture, Open Lot, Recreational, Secluded, Sloped, Trail/Near Trail, Wooded, Near Snowmobile Trails, Rural
Details
- Zoning description: resource management
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Antique,Cabin,Cottage/Camp
- Property subtype: Single Family Residence
Materials
- Wood Frame, Wood Exterior
- Foundation: Stone
- Roof: Metal,Rolled/Hot Mop,Standing Seam
Condition
- New construction: No
- Year built: 1865
Utilities & green energy
- Electric: 100 Amp Service
- Sewer: Septic Tank
- Utilities for property: Telephone at Site, Other
Community & neighborhood
Location
- Region: Whiting
Other
Other facts
- Road surface type: Gravel
Price history
| Date | Event | Price |
|---|---|---|
| 10/20/2025 | Sold | $300,000+11.3%$337/sqft |
Source:  PrimeMLS #5061400 Report a problem | ||
| 9/27/2025 | Contingent | $269,500$303/sqft |
Source: PrimeMLS #5061400 Report a problem | ||
| 9/15/2025 | Listed for sale | $269,500+73.9%$303/sqft |
Source: PrimeMLS #5061400 Report a problem | ||
| 6/19/2019 | Sold | $155,000$174/sqft |
Source: PrimeMLS #4747604 Report a problem | ||
Public tax history
Tax history is unavailable.
Neighborhood: 05778
Nearby schools
GreatSchools rating
- 4/10Mettawee Community School Usd #47Grades: PK-6Distance: 11.4 mi
- 6/10Dorset Elementary SchoolGrades: PK-8Distance: 5.7 mi
- NABurr & Burton AcademyGrades: 9-12Distance: 6.7 mi
Schools provided by the listing agent
- Elementary: Mettowee Community School
- District: Rupert School District
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Vermont
- Bennington County
- Rupert
- 05778
- 3606 Kent Hollow Road