5 Hillwinds North
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$769,900

5 Hillwinds North
Brattleboro, VT 05301
Listed by Robert Doyle · Berkley & Veller Greenwood Country
Bedrooms
4
Bathrooms
1.2
Living area
N/A
Year built
1986

About this home

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 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. 12/1/25 new System 2000 boiler, recently paved drive and so many beautiful appointments.

Property details

MLS #
5081610
Property type
Single Family Residence
Subdivision
Hillwinds
Status
Active
Days on market
126
On market date
N/A
Stories
N/A
Garage spaces
2
Lot size
11.4 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Chesterfield Central School
6.44 mi away · Grades 0-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
273
Student:teacher ratio
10.9:1
District
Chesterfield School District
Middle
Hinsdale Middle High School
9.03 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
127
Student:teacher ratio
9.8:1
District
Hinsdale School District
High
Hinsdale High School
9.03 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
140
Student:teacher ratio
8.2:1
District
Hinsdale School District

Mortgage calculator

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Est. monthly payment
$4,786/mo
$153,980 down
$615,920 loan
Principal & interest$3,995
Property tax (est.)$642
Home insurance (est.)$150

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