5 Hillwinds N Brattleboro, VT 05301

Price
$749,000
Listed On
Type
For Sale
Status
Active
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
5 Hillwinds N, Brattleboro, VT 05301
4 Beds
4 Bath
3600 sqft
Asking  $749,000

Snapshot

Type
For Sale
Category
Purchase
Property Type
Residential
Property Subtype
Other
MLS Number
5081610
Parcel Number
Property Sqft
3,600 sqft
Lot Size
11.40 acres
Year Built
1986
Year Updated
Bedrooms
4
Bathrooms
4
Full Bathrooms
1
3/4 Bathrooms
1
Half Bathrooms
2
Quarter Bathrooms
0
Lot Size (in sqft)
496,584
Price Low
-
Room Count
11
Building Unit Count
-
Condo Floor Number
-
Number of Buildings
-
Number of Floors
2
Parking Spaces
0
Location Directions
Upper Dummerston Road to Hillwinds Road. Take to the first right (Hillwinds North) and the house is the first on the right.
Subdivision Name
Hillwinds
Franchise Affiliation
None
Special Listing Conditions
Auction
Auction
Bankruptcy Property
Bankruptcy Property
HUD Owned
HUD Owned
In Foreclosure
In Foreclosure
Notice Of Default
Notice Of Default
Probate Listing
Probate Listing
Real Estate Owned
Real Estate Owned
Short Sale
Short Sale
Third Party Approval
Third Party Approval

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 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.

More Details

MLS Name
PrimeMLS
Source
ListHub
MLS Number
5081610
MLS ID
NNERENNH
Virtual Tour
PARTICIPANT
Name
Robert Doyle
Primary Phone
(802) 254-6400
Key
3YD-NNERENNH-16556
Email
mollykammerer@gmail.com
BROKER
Name
Berkley & Veller Greenwood Country Realtors
Phone
(802) 254-6400
OFFICE
Name
Berkley & Veller Greenwood Country
Phone
(802) 254-6400
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.

Features

Basement
Basement
Dock
Dock
Elevator
Elevator
Fireplace
Fireplace
Greenhouse
Greenhouse
Hot Tub Spa
Hot Tub Spa
New Construction
New Construction
Pool
Pool
Sauna
Sauna
Sports Court
Sports Court
Waterfront
Waterfront
Accessibility
Accessible Approach with Ramp
Accessible Approach with Ramp
Appliances
Gas Cooktop
Gas Cooktop
Dishwasher
Dishwasher
Dryer
Dryer
Microwave
Microwave
Wall Oven
Wall Oven
Refrigerator
Refrigerator
Washer
Washer
Domestic Water Heater
Domestic Water Heater
Tank Water Heater
Tank Water Heater
Architectural Style
Contemporary
Contemporary
Construction Materials
Post and Beam
Post and Beam
 Wood Frame
Wood Frame
Exterior
Deck
Deck
Garden Space
Garden Space
Patio
Patio
Covered Porch
Covered Porch
Shed
Shed
Double Pane Window(s)
Double Pane Window(s)
Handicap Modified
Handicap Modified
Flooring
Tile - Ceramic
Tile - Ceramic
Marble
Marble
Carpet
Carpet
Hardwood
Hardwood
Heating
Radiant
Radiant
Electric (Heating)
Electric (Heating)
Oil
Oil
Radiant Floor
Radiant Floor
Hot Water(Heating)
Hot Water(Heating)
Interior
Cathedral Ceiling
Cathedral Ceiling
Gas Fireplace
Gas Fireplace
Wood Fireplace
Wood Fireplace
3+ Fireplaces
3+ Fireplaces
Kitchen Island
Kitchen Island
Kitchen/Dining
Kitchen/Dining
LED Lighting
LED Lighting
Natural Light
Natural Light
Skylight
Skylight
Vaulted Ceiling
Vaulted Ceiling
Wet Bar
Wet Bar
Parking
Open
Open
Patio and Porch
Deck
Deck
Patio
Patio
Porch
Porch
Roof
Shingle
Shingle
Rooms
Bedroom 3
Bedroom 3
Bathroom 1
Bathroom 1
Bathroom 2
Bathroom 2
 Dining Room
Dining Room
Bedroom 1
Bedroom 1
Bathroom 3
Bathroom 3
Bedroom 2
Bedroom 2
Bathroom 4
Bathroom 4
 Basement
Basement
 Family Room
Family Room
Den
Den
 Game Room
Game Room
Bedroom 4
Bedroom 4
Utilities
Propane
Propane

History

DateEventPrice$/SqftSource
For Sale ~ Price Changed
Residential
$749,000
-5.8%
$208Berkley & Veller Greenwood Country
Listed For Sale
Residential
$795,000$221Berkley & Veller Greenwood Country
Report issue with price history

Taxes

YearAnnual AmountDescription
2025$15,576

Nearby Schools

Elementary School

Academy School (Brattleboro)

2.8 miles awayKG - 06

Elementary School

Green Street School

3.2 miles awayKG - 06

High School

Brattleboro Sr. Uhsd #6

4.2 miles away09 - 12
Show more
Get more info on 5 Hillwinds N, Brattleboro, VT 05301
Profile
Robert Doyle
Listing Agent
(802) 254-6400 ext. 133
By pressing request info, you agree that Residential and real estate professionals may contact you via phone/text about your inquiry, which may involve the use of automated means.
Profile
Robert Doyle
Listing Agent
(802) 254-6400 ext. 133
By pressing request info, you agree that Residential and real estate professionals may contact you via phone/text about your inquiry, which may involve the use of automated means.