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Deb Rees
REALTOR®
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5 Hillwinds North, Brattleboro, VT 05301

$795,000
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Active
BEDS4 BATHS2 full 2 partial SQUARE FEET3,600 MLS#5081610
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONHillwinds SCHOOLWindham Southeast

Listing Courtesy of: Berkley Veller Greenwood Country
Agency Contact: Off: 802-254-6400
Associate Name: Robert Doyle
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Property 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.

5 Hillwinds North | MLS# 5081610

This single family home located at 5 Hillwinds North, Brattleboro, VT 05301 is currently listed for sale with an asking price of $795,000. This property was built in 1986 and has 4 bedrooms and 2 full and 2 partial baths with 3600 sq. ft. Hillwinds North is located in the Hillwinds subdivision within the Windham Southeast school district. Search Hillwinds real estate on debrees.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Concrete, Concrete Floor, Partial, Partially Finished, Storage Space
Basement: Yes
Cooling: None
Garage: 2
Heating: Oil, Electric, Hot Water, Radiant Floor
Home Style: Contemporary, Post and Beam
Lot Size: 11.40 Acres
Roof Type: Asphalt Shingle
Stories: 2.0
Taxes: $15,576
Year Built: 1986

Amenities

Cathedral Ceiling
Gas Fireplace
Wood Fireplace
3+ Fireplaces
Kitchen Island
Kitchen/Dining
LED Lighting
Natural Light
Skylight
Vaulted Ceiling
Wet Bar
Deck
Garden Space
Patio
Covered Porch
Shed
Double Pane Window(s)
Handicap Modified

Feature Descriptions

Accessibility: 1st Floor 1/2 Bathroom, 1st Floor 3 Ft. Doors
Appliances: Gas Cooktop, Dishwasher, Dryer, Microwave, Wall Oven, Refrigerator, Washer, Domestic Water Heater, Tank Water Heater
Baths 1/2: 2
Baths 3/4: 1
Baths Full: 1
Color: White
Construction: Post and Beam, Wood Frame
Construction Status: Existing
Days on Site: 16
Driveway: Paved
Electric: 200+ Amp Service, Circuit Breaker(s)
Exterior: Post and Beam, Wood Frame
Flood Zone: No
Flooring: Carpet, Ceramic Tile, Hardwood, Marble, Other
Foundation: Poured Concrete
Lot: Corner, Country Setting, Field/Pasture, Landscaped, Major Road Frontage, Mountain View, Near Country Club, Near Golf Course, Near Paths
Number of Rooms: 11
Parking: Auto Open, Storage Above, Paved, Detached
Road Frontage: 2463
Roads: Paved, Public Maintained Road
Sewer: Septic
Sq. Ft. Above Grade Finished: 3000
Sq. Ft. Below Grade Finished: 600
Sq. Ft. Total Finished: 3600
Total Stories: 2
Water: Drilled Well
Zoning: Residential

Room Sizes

Kitchen/Dining: 22X13 Level - 1
Living Room: 17X17 Level - 1
Family Room: 22X22 Irregular Level - 1
Den: 8X13 Level - 1
Rec Room: 35X17.5 Level - Basement
Foyer: 21X17 Level - 1
Mudroom: 7X8 Level - 1
Bedroom: 14.5X17.5 Level - 2
Bedroom: 10X13.5 Level - 2
Bedroom: 11X19.5 Level - 2
Bedroom: 11X11.5 Level - 2
Bathroom Full: 16.5X11 Level - 2
Bathroom Three Quarter: 6X10 Irreg Level - 2
Bathroom Half: 13.5X5 &W&D Level - 1
Bathroom Half: 4.5X5 Level - Basement

Local Schools

School District: Windham Southeast

Listed By / Shown By

Listed By

Agency Name: Berkley Veller Greenwood Country
Agency Contact: Off: 802-254-6400
Agent Name: Robert Doyle

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Estimated Payment

$ 3,299.20 per month $1,769.33 Principal & Interest $1,298.00 Property Tax $231.88 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/17/2026. The listing information on this page last changed on 04/17/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 04/17/2026 5:02:47 AM EST) or MLSPIN MLS (last updated Thu 04/16/2026 11:38:34 PM EST) or Prime MLS (last updated Thu 04/16/2026 11:33:24 PM EST) or MREIS (last updated Fri 04/17/2026 2:05:22 AM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) copyright © 2026 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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data Last Updated 2026-04-16 23:33:24

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