by RH Advisors

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Windham 05301
5 Hillwinds North
Listed by: Robert Doyle, Berkley & Veller Greenwood Country, Off: 802-254-6400, , Listing Courtesy of Prime MLS
$769,900
● House - In Contract

5 Hillwinds North

Brattleboro, VT 05301
bedrooms
4 Beds
bathrooms
1 Bath, 2 Half Baths
square feet
4,200 Ft²
$5,079
Est. Monthly

About This Property

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.
Unit Size
4,200 Ft²
Days on Market
-
Land Size
11.40 acres
Price per sqft
$183
Property Type
House
Property Taxes
$1,298
HOA Dues
-
Year Built
1985

Listed By

Robert Doyle
Berkley & Veller Greenwood Country

Payment Calculator (Computations Provided by RealtyHop)

Cap Rate Calculator

Last updated: 2 months ago (Prime MLS #5081610)

Price History

Date / Event Date Event Price
Aug 19, 2026 In contract -
In contract
Jul 14, 2026 Price Increased $769,900
↑ $21K (2.8%)
Price Increased
Jul 3, 2026 Relisted $749,000
Relisted
Jun 26, 2026 In contract -
In contract
Jun 9, 2026 Price Decreased $749,000
↓ $46K (5.8%)
Price Decreased
Show More

Property Highlights

Garage
Fireplace
Parking Details
Has Garage
Has Open Parking
Parking Features: Storage, Paved, Detached, Auto Open
Garage Spaces: 2
Interior Details
Half Bathrooms: 2
Full Bathrooms: 1
Interior Features: Cathedral Ceiling(s), Kitchen Island, Vaulted Ceiling(s), Wet Bar, Gas Fireplace, Wood Fireplace, 3+ Fireplaces, Kitchen/Dining, LED Lighting, Natural Light, Skylight
Appliances: Gas Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer, Water Heater, Wall Oven
Flooring Type: Carpet, Ceramic Tile, Hardwood, Marble, Other
Rooms: 11
Basement: Yes
Exterior Details
Square Footage: 4200
Architectural Style: Contemporary, Post and Beam
Year Built: 1986
Construction Materials: Wood Siding, Post and Beam
Lot Features: Corner Lot, Pasture, Landscaped, Near Golf Course, Country Setting, Major Road Frontage, Mountain View, Near Country Club, Near Paths
Lot Size Area: 496584
Lot Size Units: Square Feet
Lot Size Acres: 11.4
Lot Size Square Feet: 496584
Water Source: Drilled Well
Financial Details
Tax Annual Amount: $15,576
Utilities Details
Cooling Type: None
Heating Type: Oil, Electric, Hot Water, Radiant Floor
Sewer : Septic Tank

Building Info

Overview

    General

  • Year Built: 1985
  • Effective Year Built: 1985
  • Building Count: 1
  • Total Rooms: 9
  • Bedroom Count: 4
  • Bathroom Count: 3
  • Full Bathrooms: 2
  • Partial Bathrooms: 3
  • Building Condition: 6
  • Building Quality: 0
  • Construction Type: 6
  • Building Style: 21
  • Exterior Walls Type: 18
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 0
  • Floor Count: 200
  • Floor Cover: 0
  • Basement Type: 2
  • Basement Area: 0
  • Garage Type: 4
  • Parking Space Count: 0
  • Patio Type: 0
  • Porch Type: 0
  • Pool Type: 0

    Dimensions

  • Lot Size Square Feet: 496,584
  • Total Building Area: 2,841
  • Gross Building Area: 2,841
  • Building Area: 2,841
  • Building Area Measurement: L

    Heating and Cooling

  • Air Conditioning: 0
  • Heating: 0
  • Heated Square Feet: 2,841
  • Heating Fuel Type: 0

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Land Acres: 0000011400
  • Standard Land Use Code: 1001
  • County Land Use Code: 101
  • Legal Description 1: DWELLING/GARAGE/LAND

Neighborhood

  • School District Name: Windham Southeast Supervisory Union
  • Census Tract: 968400

Zoning

  • Zoning: RR / R

Geography

  • Parcel: (025) 00070106.000
  • Municipality: BRATTLEBORO
  • Latitude: 42.8928
  • Longitude: -72.5971

    Address

  • Full Address: 5 Hillwinds N
  • Address - House Number: 5
  • Street Segment Direction: N
  • Address - Street Name: Hillwinds
  • State: VT
  • City Name: Brattleboro
  • Carrier Code: R001
  • 4-Digit Zip Code: 9077
  • Zip Code: 05301

Valuation

    Tax

  • Tax Year: 2022
  • Tax Amount: $343,838
  • Tax Rate Code Area: 025

    Appraisal Valuation

  • Standard Deviation: 0.1868
  • Valuation Date: Apr 26, 2023
  • Confidence Score: 62
  • Final Value: 534,226
  • High Value: 634,045
  • Low Value: 434,406

    Assessments Valuation

  • Assessed Year: 2022
  • Assessed Total Value: $447,240
  • Assessed Land Value: $109,940
  • Assessed Improvements Value: $337,300

    Exemptions

  • Homeowner Exemption: Yes

    Sales

  • Current Sale Contract Date: Jul 09, 2001
  • Current Sale Recording Date: Jul 09, 2001
  • Current Sale Price:
  • Current Sale Document Type: 36
  • Current Sale Input Document Number: 371562
  • Previous Sale Recording Date: Apr 08, 1997
  • Previous Sale Contract Date: Apr 08, 1997
  • Previous Sale Amount: $35,000
  • Previous Sale Document Type: 36
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Windham


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Nearby Rentals

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$1,325 /mo

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Frequently Asked Questions

When was property at 5 Hillwinds North built and last sold?
The property at 5 Hillwinds North was built in 1985 and last sold on Jul 9, 2001 for $332,500.
How much is this home worth?
The estimated value of the home located at 5 Hillwinds North is $785,307.
What are some comparable homes to 5 Hillwinds North?
There are currently no comparable homes to 5 Hillwinds North.