# 5 Hillwinds North, Brattleboro, VT 05301

> **TL;DR:** 4bd/4ba single family, $795,000 ($221/sqft), built 1986, 3,600 sqft.
> Hardwood, Basement. Est. $3,445/mo. Listed 61 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $795,000 |
| Price/sqft | $221 |
| Bedrooms | 4 |
| Bathrooms | 1 full, 2 half |
| Square Feet | 3,600 |
| Year Built | 1986 |
| Lot Size | 496,584 sqft (11.40 acres) |
| Stories | 2 |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 61 |

## Why This Home Stands Out

- **Hardwood Floors** - Throughout the home

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $3,445 |
| **Total** | **$3,445** |

## Key Amenities

- Hardwood
- Basement

## Property Highlights

- Built in 1986
- 11.40 acre lot
- 2 stories
- 2 parking spaces

## Description

### Agent Description
Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community.  Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer with skylight, entry closet and stained-glass windows.  Adjacent, opens into a warm, spacious family room with cherry wainscoting, a gas stone fireplace, curved architectural accents and mud room access.  The formal living room features a brick fireplace and is surrounded by classic post & beam architecture and stained glass windows. The open kitchen & dining area are ideal for entertaining and impress with cherry cabinetry, quartz countertops, stainless appliances, and sliders to an expansive deck with serene views. A den, half bath, and laundry closet complete the main level. Upstairs offers four bedrooms, including a stunning primary suite with cathedral ceiling, triple closets, fireplace, and Palladian windows. There is a tucked-away guest room that enjoys a private ¾ bath. The finished lower level includes a generous game room with wet bar, half bath, propane stove, & TV area—pool table included! A detached 2-car garage with storage, a garden shed, and timeless craftsmanship throughout make this a truly rare offering.

## Location

- **Address:** 5 Hillwinds North, Brattleboro, VT 05301
- **County:** Windham
- **Neighborhood:** Hillwinds

## Listing Agent

- **Name:** Robert Doyle
- **Brokerage:** Berkley & Veller Greenwood Country
- **Phone:** 8022546400x133
- **Email:** robert.doyle@berkleyveller.com

## Primary Photo

![5 Hillwinds North - Primary Photo](http://lh.rdcpix.com/cacaaf65b749f2c6810a5bfd63c88b3fl-f3417218848r.jpg)

*37 total photos available on [listing page](https://www.propertysimple.com/listing/5-hillwinds-north-brattleboro-vt-05301-5081610)*

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**MLS#:** 5081610 | **Updated:** 2026-06-17
**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.com/listing/5-hillwinds-north-brattleboro-vt-05301-5081610)

---

## Structured Data

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  "@type": "RealEstateListing",
  "name": "5 Hillwinds North, Brattleboro, VT 05301",
  "description": "Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community.  Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered porch that opens into a marble floored foyer with skylight, entry closet and stained-glass",
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  "numberOfBedrooms": 4,
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