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$849,000
2 Days On Site

5 Hillwinds North Road
Brattleboro, VT 05301

For Sale|Single Family Residence|Active
4
Beds
4
Total Baths
1
Full Bath
3
Partial Baths
3,600
SqFt
$236
/SqFt
1986
Built
Subdivision:
Hillwinds
County:
VT-Windham
Listing courtesy of Robert Doyle of Berkley & Veller Greenwood Country Off: 802-254-6400
Call Now: 802-254-6400
Is this the listing for you? We can help make it yours.
802-254-6400
5 Hillwinds North Road5 Hillwinds North Road5 Hillwinds North Road5 Hillwinds North Road
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Mortgage Calculator

Monthly Payment (Est.)

$3,873
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2025 Information is deemed reliable but not guaranteed.

Elegant Post-and-Beam home in coveted Hillwinds. Tucked along a birch-lined drive, this exceptional post-and-beam home is set on 11+ acres of landscaped grounds with lawns, stone walls, gardens, and mixed woodland 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. Delay show 8/30.

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Listing Snapshot
Price 
$849,000
Days On Site 
2 Days
Bedrooms 
4
Inside Area (SqFt) 
3,600 sqft
Total Baths 
4
Full Baths 
1
Partial Baths 
3
Lot Size 
11.4 Acres
Year Built 
1986
MLS® Number 
5058499
Status 
Active
Property Tax 
$15,575.56
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
yesterdayListing updated with changes from the MLS®
2 days agoListing first seen on site
General Features
Acres 
11.4
Garage 
Yes
Garage Spaces 
2
Number Of Stories 
2
Parking 
PavedDetached
Parking Spaces 
2
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Above 
3000
SqFt Below 
600
SqFt Total 
4200
Style 
ContemporaryPost and Beam
Water Source 
WellPrivate
Zoning 
Residential
Interior Features
Appliances 
DishwasherDryerRefrigeratorMicrowaveWasher
Basement 
ConcretePartially FinishedPartial
Electric 
200+ Amp ServiceCircuit Breakers
Fireplace 
Yes
Fireplace Features 
GasWood Burning
Fireplaces 
3
Flooring 
CarpetCeramic TileHardwoodMarble
Heating 
Hot WaterRadiant
Interior 
Kitchen IslandWet BarCathedral Ceiling(s)Vaulted Ceiling(s)
Bathroom 1 
Dimensions - 16.5X11
Bathroom 2 
Dimensions - 6X10 Irreg
Bathroom 3 
Dimensions - 13.5X5 &W&D
Bathroom 4 
Dimensions - 4.5X5
Bedroom 1 
Dimensions - 14.5X17.5
Bedroom 2 
Dimensions - 10X13.5
Bedroom 3 
Dimensions - 11X19.5
Bedroom 4 
Dimensions - 11X11.5
Den 
Dimensions - 8X13
Family Room 
Dimensions - 22X22 Irregular
Foyer 
Dimensions - 21X17
Kitchen 
Dimensions - 22X13
Living Room 
Dimensions - 17X17
Mudroom 
Dimensions - 7X8
Rec Room 
Dimensions - 35X17.5
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Exterior Features
Lot Features 
Corner Lot
Other Structures 
Shed(s)
Patio And Porch 
DeckPatio
Roof 
Shingle
View 
Mountain(s)
Waterview 
Mountain(s)
Community Features
Accessibility Features 
Accessible Full Bath
School District 
Windham Southeast
Schools
School District
Windham Southeast
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of Robert Doyle of Berkley & Veller Greenwood Country Off: 802-254-6400



Copyright 2025, PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Last checked: 2025-08-29 07:16 PM UTC
Neighborhood & Commute
Source: Walkscore
Community information and market data Powered by ATTOM Data Solutions. Copyright ©2019 ATTOM Data Solutions. Information is deemed reliable but not guaranteed.
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