Ad #7840646
MLS #5081610
New updates: roof replacement with 30 year architectural
5 Hillwinds N, Brattleboro, VT 05301
$769,900
4Beds
4Baths
3,600Sqft
11.4Acres
About this property
New updates: roof replacement with 30 year architectural shingles completed and six new skylights with remote control shades installed. 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 3/4 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. 12/1/25 new System 2000 boiler, recently paved drive and so many beautiful appointments.
Property Features
4 Beds
4 Baths
3,600 Sqft
Built in 1986
11.4 Acres
2 Stories
Open
Siding: Post and Beam, Wood Frame
Shingle Roof
Has Fireplace
Oil, Radiant, Electric (Heating), Hot Water(Heating), Radiant Floor
$15,576 / yr property tax
Windham County
Hillwinds Community
Additional Photos
Contact Information
Robert Doyle
Berkley & Veller Greenwood Country Realtors
802-254-6400
Location
Listing Agent: Robert Doyle 802-254-6400
Broker: Berkley & Veller Greenwood Country Realtors 802-254-6400 Listing Site
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.
Broker: Berkley & Veller Greenwood Country Realtors 802-254-6400 Listing Site
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.
BarrierFreeHome.com
Printed Sep 22, 2026
Photo Gallery
$769,900
4
Beds
4
Baths
3,600
Sqft
5 Hillwinds N, Brattleboro, VT 05301
By contacting this agent you agree to these Terms and Conditions.
MLS# 5081610
$769,900
5 Hillwinds N, Brattleboro, VT 05301
4
Beds
4
Baths
3,600
Sqft
11.4
Acres
$769,900
5 Hillwinds N, Brattleboro, VT 05301
4 Beds
4 Baths
3,600 Sqft
11.4 Acres
Accessibility Features
Accessible Approach with Ramp
New updates: roof replacement with 30 year architectural
New updates: roof replacement with 30 year architectural shingles completed and six new skylights with remote control shades installed. 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 3/4 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. 12/1/25 new System 2000 boiler, recently paved drive and so many beautiful appointments.
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Property Details
HOME DETAILS
4 Beds
4 Baths
3,600 Sqft
Built in 1986
11.4 Acres
2 Stories
EXTERIOR
Open
Siding: Post and Beam, Wood Frame
Shingle Roof
INTERIOR
Has Fireplace
Oil, Radiant, Electric (Heating), Hot Water(Heating), Radiant Floor
FINANCIAL & COMMUNITY
$15,576 / yr property tax
Windham County
Hillwinds Community
See More Details
Location
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Ad Statistics
Ad Number
7840646
Viewed
60 times
Listing Status
Active Under Contract
Added
Jun 03, 2026
Last Refreshed
Sep 22, 2026 10:37:00 AM
Listing Information
Data Source
PrimeMLS
Source Property ID
5081610
Listing Agent: Robert Doyle 802-254-6400
Broker: Berkley & Veller Greenwood Country Realtors 802-254-6400 Listing Site
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.
Broker: Berkley & Veller Greenwood Country Realtors 802-254-6400 Listing Site
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.
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