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Single family home for sale at 33 Highfield Dr, Windsor, VT 05089 | MLS# 5114346 | Listing updated on 2026-10-16
Photo 1 of Single family home for sale at 33 Highfield Dr, Windsor, VT 05089 | MLS# 5114346 | Listing updated on 2026-10-16
Photo 2 of Single family home for sale at 33 Highfield Dr, Windsor, VT 05089 | MLS# 5114346 | Listing updated on 2026-10-16
Photo 3 of Single family home for sale at 33 Highfield Dr, Windsor, VT 05089 | MLS# 5114346 | Listing updated on 2026-10-16
Photo 4 of Single family home for sale at 33 Highfield Dr, Windsor, VT 05089 | MLS# 5114346 | Listing updated on 2026-10-16
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Listed by: Danny Kogut | Williamson Group Sothebys Intl. Realty (802) 457-2000

$1,350,000

Monthly Est:$6,719

  • Beds Icon4 Beds
  • Beds Icon
    4 Baths
  • Beds Icon2,650sqft

33 Highfield Dr, Windsor, VT 05089

$6,719/moEst:

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  • Single Family Residence

  • Built in 1988

  • $-- HOA

  • 13.01 acres lot

  • $509/sq.ft

Description

An exceptional 13.1-acre equestrian property with direct access to the GMHA trail system in sought-after West Windsor. This Lindal Cedar home features expansive windows, vaulted ceilings, and wide decks overlooking grassy pastures and distant views of Mt. Ascutney. The newly designed kitchen includes Crown Point cabinetry, granite countertops, and stainless-steel appliances. Upstairs, the primary bedroom has a wood-burning fireplace, while the ensuite bathroom offers a soaking tub and tiled shower. Two additional bedrooms on the main level each with a bathroom. First-floor laundry / powder room. Mudroom with custom cabinetry and direct access to a 2-car garage. Automatic generator. The stone patio includes a fire pit, and the property has electric dog fencing. A custom two-story barn offers five stalls with direct access, heated tack room, automatic heated waterers, large, fenced grass paddocks, an oversized riding ring and round pen, All-season recreational opportunities with easy access to VAST snowmobile trails. Hike and cycle on the dirt road system. 15 minutes to GMHA, 20 minutes to Woodstock. 30 minutes to Hanover, NH, 2.25 hours to Boston.

  • Houzeo last checked: 12 hours ago
  • Listing updated: October 16, 2026 at 3:19 pm
  • Source: NEREN/Prime MLS-NH | MLS#: 5114346 NEREN/Prime MLS-NH

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Vt Windsor County

  • City

    Windsor

  • Neighborhood

    --

  • Year Built

    1988

  • HOA Fees

    -

  • Finished Area

    2,650 sqft

  • Lot Size

    13.01 acres lot

  • Basement Area

    - sqft

  • MLS Name

    NEREN/Prime MLS

  • MLS Number

    5114346

  • MLS Status

    (10) Active - Active

  • Days on Market

    19

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 4

Interior

  • Heating

    Propane, Wood, Baseboard

  • Sewer

    Septic Tank

  • Cooling

    None

Construction

  • Year Built

    Year Built: 1988

  • Home type

    Single Family Residence

  • Roof

    Standing Seam

  • Construction Materials

    Wood Frame

  • Foundation Details

    Concrete

  • Architectural Style

    Contemporary

  • Property Condition

    Existing

Utilities & Energy

  • Electric

    Circuit Breakers

  • Basement

    Concrete, Daylight, Full, Interior Stairs, Unfinished, Walk Out Access

  • Water Source

    Drilled Well

  • Utilities

    Propane

Other Features

  • Lot Features

    Country Setting, Farm, Pasture, Level, Mountain View, Open Lot, Ski Area, Near Paths, Near Skiing, Near Snowmobile Trails

Price History

DateEventPrice

10/16/2026

Source: mls_logoNEREN/Prime MLS-NH #5114346

Listed for Sale

$1,350,000

$509/sqft

Nearby Homes

Based on information from PrimeMLS Inc. through Nov 02, 2026, 02:16PM. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information. The listing broker's offer of compensation is made only to other real estate licensees who are participant members of PrimeMLS. 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 Nov 02, 2026, 02:16PM. © 2026 PrimeMLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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