We want to share with you local real estate listings featuring properties that are located on the GMHA Trail Network.
We hope to facilitate interest—and ultimately sales—to keep these properties in the hands of horse people who will keep them open to share with riders. We also hope they will consider donating their trails to GMHA, so they will be protected…forever!
Brief property descriptions and direct links to the listings are provided for each property. Anyone interested—or if you know someone who may be interested—should contact the realtors directly.
Farm at Gaelic Crossing
325 Cemetery Rd, West Windsor, Vermont
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 rainbowsoften even double rainbowsacross the wide, open sky.
This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedroomstwo 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
Skyland Farm
412 Skyland Ln, Woodstock, Vermont
Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 65 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg.
Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace.
At the heart of the home is a chef’s kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, chicken coop, and a spacious barn perfect for guest quarters, workshop or a car collection.
Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter.
The farm is found near *Sanatoga Spring once a 19th-century destination for its healing mineral waters. Echoing the legacy of Sanatoga Spring, Skyland’s own mineral waters feed three pristine ponds, anchoring a landscape that brings both peace and clarity. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby.
John Arnold Cottle House
4945 S Rd, South Woodstock, Vermont
The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area’s earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 feet of frontage on Kedron Brook, along with a firepit, a barn, and a river meadow. The barncurrently used for storagecould easily be converted to accommodate a couple of horses or sheep.
The three-bedroom main house has elegant 12-over-12 windows, high ceilings, and beautifully preserved period details, including a second-floor ballroom with a coved ceiling and fiddler’s stagea nod to its past as a lively gathering space. The newer addition overlooking the brook has a magnificent great room with 17′ cathedral ceilings and a gourmet kitchen and wood burning brick fireplace.
The renovated Kingsley Barn guest house offers two bedrooms, a loft, and a deck overlooking the brook. Below there is a heated workshop, ideal for puttering, creating, and getting lost in a project. A timber bridge spans the waterway, connecting the property’s field, barn and trails.
With direct access to the Upwey Trail system and equestrian paths leading to the Green Mountain Horse Association, this property is ideal for outdoor enthusiasts. Located along South Road in the South Woodstock Historic District, the home is part of a landscape of preserved 19th-century architecture and pastoral beauty.
