# 1060 Upper Hollow Road, Dorset, VT 05251

> **TL;DR:** 5bd/6ba single family, $5,600,000 ($1198/sqft), built 1965, 4,674 sqft.
> Fireplace, A/C. Est. $29,950/mo. Listed 227 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $5,600,000 |
| Price/sqft | $1198 |
| Bedrooms | 5 |
| Bathrooms | 1 full, 1 half |
| Square Feet | 4,674 |
| Year Built | 1965 |
| Lot Size | 2,901,096 sqft (66.60 acres) |
| Stories | 1 |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 227 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $28,317 |
| Estimated Insurance | $1,633 |
| **Total** | **$29,950** |

## Nearby Schools

- **High:** Burr and Burton Academy

## Key Amenities

- Fireplace
- A/C

## Property Highlights

- Built in 1965
- 66.60 acre lot
- Fireplace

## Description

### Agent Description
'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'... This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplace, perfect for cozy evenings. The main residence captures the landscape from every angle blending modern architecture seamlessly with nature. This is much more than a home, it is truly a legacy property... Prestigious, Private and Profoundly Peaceful and must be seen to be fully appreciated!! Beauty, solitude, quiet luxury!!! Subdivision potential.

## Location

- **Address:** 1060 Upper Hollow Road, Dorset, VT 05251
- **County:** VT-Bennington
- **Coordinates:** 43.26389519, -73.06509227
- **Google Maps:** https://www.google.com/maps?q=43.26389519,-73.06509227

## Virtual Tour & Media

- **Video Tour:** https://tour.neren.com/1060-Upper-Hollow-Road-Dorset-VT-05251/unbranded

## Listing Agent

- **Name:** Sunny Breen
- **Brokerage:** Josiah Allen Real Estate inc.
- **Phone:** (802) 867-5555
- **Broker Phone:** (802) 867-5555
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1060-Upper-Hollow-Rd_Dorset_VT_05251_M39054-87080?f=listhub&s=NNERENNH&m=5075285&c=propsimple)

## Photos

![1060 Upper Hollow Road - Photo 1](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f4060028080r.jpg)

![1060 Upper Hollow Road - Photo 2](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f1430777608r.jpg)

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![1060 Upper Hollow Road - Photo 35](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f1986687447r.jpg)

![1060 Upper Hollow Road - Photo 36](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f1484893411r.jpg)

![1060 Upper Hollow Road - Photo 37](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f1435384236r.jpg)

![1060 Upper Hollow Road - Photo 38](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f2337591925r.jpg)

![1060 Upper Hollow Road - Photo 39](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f3945606382r.jpg)

![1060 Upper Hollow Road - Photo 40](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f1500937421r.jpg)

![1060 Upper Hollow Road - Photo 41](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f1651731986r.jpg)

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![1060 Upper Hollow Road - Photo 47](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f923020539r.jpg)

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![1060 Upper Hollow Road - Photo 49](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f2269087695r.jpg)

![1060 Upper Hollow Road - Photo 50](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f191651924r.jpg)

![1060 Upper Hollow Road - Photo 51](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f1403529283r.jpg)

![1060 Upper Hollow Road - Photo 52](http://lh.rdcpix.com/61b3454fc5a92f0c9199454007c1faedl-f4180008180r.jpg)

---

**MLS#:** 5075285 | **Updated:** 2026-09-13
**Source:** listhub

*Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/1060-upper-hollow-road-dorset-vt-05251-5075285)

---

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