Skip To Content
Courtesy of Robert Doyle of Berkley & Veller Greenwood Country: Off: 802-254-6400.

5 Hillwinds North

Brattleboro, VT 05301
  • $749,000
  • STATUS: Active
  • ON SITE: 69 Days
  • MLS #: 5081610
Price Reduced
UPDATED: 67 min ago
$749,000
  • 4
    BEDS
  • 11.4
    ACRES
  • 2
    BATHS
  • 2
    1/2 BATHS
  • 3,600
    SQFT
  • $208
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1986
County:
Area:

School Ratings & Info

School District:

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 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.

Monthly Payment Calculator



© Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 2026-06-10T17:06:06.353.
www.livingvermont.com/homes/174724929
Print Image

5 Hillwinds North Brattleboro, VT 05301

  • Price: $749,000
  • Status: Active
  • On Site: 69 Days
  • Updated: 67 min ago
  • MLS #: 5081610
4
Beds
2
Baths
2
½ Baths
11.4
Acres
3,600
SQFT
$208
$/SQFT
1986
Built
Neighborhood:
Hillwinds
County:
Windham
Area:
Brattleboro
School District:
Windham Southeast
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 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.
Exterior Features

Architectural Style ContemporaryPost and Beam Color White Construction Materials Post and BeamWood Frame Driveway Paved Exterior Features DeckGarden SpacePatioCovered PorchShedDouble Pane Window(s)Handicap Modified Has Garage Yes Lot Features CornerCountry SettingField/PastureLandscapedMajor Road FrontageMountain ViewNear Country ClubNear Golf CourseNear Paths Parking Auto OpenStorage AbovePavedDetached Road Frontage Yes Road Frontage Length 2463 Roof Asphalt Shingle

Interior Features

Appliances Gas CooktopDishwasherDryerMicrowaveWall OvenRefrigeratorWasherDomestic Water HeaterTank Water Heater Basement Access Type Interior Basement Description ConcreteConcrete FloorPartialPartially FinishedStorage Space Cooling None Flooring CarpetCeramic TileHardwoodMarbleOther Foundation Poured Concrete Has Basement Yes Heating OilElectricHot WaterRadiant Floor Interior Features Cathedral CeilingGas FireplaceWood Fireplace3+ FireplacesKitchen IslandKitchen/DiningLED LightingNatural LightSkylightVaulted CeilingWet Bar Quarter Baths 0 Rooms Level B Level B: 1/2 BathroomLevel B: Rec Room Rooms Level1 Level 1: 1/2 BathroomLevel 1: DenLevel 1: Family RoomLevel 1: FoyerLevel 1: Kitchen/DiningLevel 1: Living RoomLevel 1: Mudroom Rooms Level2 Level 2: BedroomLevel 2: Full BathroomLevel 2: 3/4 Bathroom Rooms Total 11 Sq Ft Approx Fin Above Grade 3000 Sq Ft Approx Fin Below Grade 600

Property Features

Auction No Construction Status Existing Covenants Yes Electric 200+ Amp ServiceCircuit Breaker(s) Features Accessibility 1st Floor 1/2 Bathroom1st Floor 3 Ft. Doors Flood Zone No Foreclosed / Bank Owned / REO No Pre Construction No Property Type Single Family Road Frontage Type PavedPublic Maintained Road Seasonal No Sewer Septic Span Number 081-025-14521 Surveyed Unknown Tax Gross Amount 15576 Tax Year 2025 Taxes Tbd No Timeshare Fractional Own No Utilities Propane Water Source Drilled Well Zoning Residential

Courtesy of Robert Doyle of Berkley & Veller Greenwood Country: Off: 802-254-6400.


© Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 2026-06-10T17:06:06.353.
 
https://bt-photos.global.ssl.fastly.net/nneren/1280_boomver_2_5081610-2.jpg https://bt-photos.global.ssl.fastly.net/nneren/1280_boomver_2_5081610-2.jpg https://bt-photos.global.ssl.fastly.net/nneren/1280_boomver_2_5081610-2.jpg
Logo
RE/MAX North Professionals
553 Roosevelt highway suite 200
Colchester VT, 05446