West Windsor, VT | 33 Highfield Drive

They say land remembers. On Rush Meadow Road-where rolling fields meet the quiet rhythm of the seasons-there is a place that has been held, cared for, and passed down for over a century. This 103-acre estate is not something that was assembled. It was lived. Worked. Protected. For generations, it operated as a dairy farm, and the land still reflects that stewardship—lush hayfields, a ready-to-tap sugarbush, rich soil for gardening and beautiful solar exposure across every acre. It’s the kind of property that continues to give, year after year. At its heart sits a classic Vermont farmhouse with 3 bedrooms and 1.5 baths, grounded by its traditional woodshed ell and surrounded by substantial garage and equipment space. It’s practical, authentic, and full of quiet character, equally suited as a full-time residence or a welcoming guest house. To the west, the land opens into sweeping fields with one of the most compelling building sites in the region with long-range views stretching to Mt. Ascutney, expansive and uninterrupted. Whether you envision a private compound, a retreat, or preserving the land as it has been for generations, the setting invites something meaningful. Consider your dream home resting at the height of the land, the beginning to your own heritage. Moments from Brownsville, with easy access to trails across Ascutney Mountain, coffee at local favorites like the Butcher & Pantry, and the culture of Woodstock just 25 minutes down the road, this property offers both connection and complete escape. This is not simply a farm. It is a legacy......waiting for its next chapter!

Sited on a knoll with lovely views in every direction, this spacious, sun filled Contemporary home was built to last! Using the finest materials, commercial grade mechanics, and custom millwork, this home imbues quality throughout. An impressive fireplace with a wood burning insert anchors the Great Room with sweeping walls of windows integrating indoor and outdoor spaces, and French doors stepping out to a massive deck for entertaining. The kitchen is well suited with top quality appliances, granite counters and maple cabinetry. There is a primary bedroom ensuite, and a guest bedroom, and a study on the main level. Moving downstairs, the expansive spaces offer a variety of options as extended family space, or an in-law accommodation. There's a family room with fireplace, a large area for home gym, or play space. Two additional rooms for guest accommodation, a cedar closet, full bathroom, potential for a second kitchen. Outdoors, the property is magical with terraced perennial beds, mature trees and shrubs all selected to attract birds and butterflies. The oversized barn has three bays, a heated workshop/studio with bathroom, and ample loft space for hay/storage. Commercial grade generator, solar array. Lovely trail network lacing through the property. Easy access to Interstate, Woodstock, Hanover NH, skiing, golf and recreation.

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.

Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide pine and maple floors run throughout, adding classic farmhouse character. The equestrian amenities are outstanding: a 3,024-square-foot stable with seven spacious stalls, a heated tack room, wash stall, bathroom, and laundry area. The 100' x 200' riding arena features a state-of-the-art, eco-friendly footing made from recycled sneakers, offering outstanding drainage, low dust, and excellent footing. Outdoor facilities also included are a round pen, four grass paddocks, and one dirt paddock. Quiet gravel roads invite walking and riding, with access to the Green Mountain Horse Association trail system. A stream winds along the property's West border, while apple and pear trees provide seasonal bounty. High-speed internet ensures fast connectivity. Ascutney Outdoors, with 40 miles of trails for horseback riding, mountain biking, skiing, and hiking, is nearby, and the popular Brownsville Butcher and Pantry is less than two miles away. (Horses not included)

Constructed in 2025, and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic floating staircase leading to the loft area. Red oak flooring runs throughout. The open concept kitchen is suited with top quality appliances, and a center island with a rich walnut edged yellow birch countertop. The first level Primary ensuite has a dressing room with laundry, and bathroom with a walk in shower and soaking tub. Up the stairs, there's a spacious area for TV Room, or office and a guest bedroom. The walk-out lower basement level is spacious with high ceilings- perfect opportunity for future expansion. The home connects seamlessly to exterior spaces with a stone terrace and a screened porch, both situated to highlight the lovely pastoral views to Mt Ascutney, and beyond. State of the art mechanicals with central AC. Convenient to trail network, all recreation, Woodstock, Hanover NH and Interstate.

With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone. The newer addition features an open concept kitchen, dining, and living area anchored by a custom stone fireplace and dramatic floor to ceiling windows framing the mountain views. A sun-filled deck invites morning coffee, summer entertaining, or cozy après ski evenings. The primary suite is a private retreat with its own deck, ensuite bath, walk in closet, and dedicated office. The original wing offers four additional bedrooms, a kitchen, living area, and its own deck, creating an ideal space for guests or extended family. Whether enjoyed as one expansive residence, configured for private guest accommodations, or explored for its income-producing rental potential, the flexible layout adapts to a variety of lifestyles. Located in the heart of Brownsville. Just minutes from Mount Ascutney's trails and outdoor recreation, and within easy reach of Woodstock, Okemo, Killington, and the Upper Valley, this is a rare opportunity to own a true Vermont retreat where unforgettable memories are made all year long, with the added flexibility of potential rental income when you're away.