Properties Near 1342 Old Stage Road Chester, VT

Showings begin Monday 12/29 | Discover a truly one-of-a-kind Vermont retreat set on 10 acres of peaceful woodland and open meadow. Originally built as a family-run maple sugar shack, this architect-designed home has been thoughtfully reimagined and newly completed, seamlessly blending rustic charm with contemporary comfort to create a warm and inviting hideaway unlike anything else on the market. Post-and-beam construction, expansive views, and thoughtful design define the main residence, which offers two spacious bedrooms and cozy, character-filled living space inspired by its sugaring heritage. Complementing the main home is a charming one-bedroom Yurt—ideal for guests, a creative studio, or a quiet personal retreat. Wander the property to enjoy sun-dappled walking paths, open skies, and a tranquil pond that attracts abundant wildlife and enhances the sense of serenity. Efficiently designed with solar panels, this property offers both sustainability and comfort. Ideally located less than a quarter mile from access to the VAST snowmobile trail network and within easy reach of seven ski areas in southern Vermont as well as year-round recreation. A magical estate perfectly suited for a weekend sanctuary, creative escape, or distinctive Vermont homestead. A rare opportunity to slow down, reconnect with nature, and experience the extraordinary.

Welcome to your own private retreat—98 acres of Vermont beauty offering meadows, woods, two ponds, and eight versatile outbuildings. Thoughtfully maintained, this charming home is nestled in a park-like setting complete with long, historic rock walls, mature trees, and lovely perennial gardens. Nature lovers will appreciate the abundance of wildlife, from hummingbirds and ducks to deer and the occasional moose wandering past the apple trees and blueberry bushes. Step onto the screened porch overlooking the main pond, perfect for morning coffee or evening relaxation. Inside, warm wood floors and exposed beams enhance the home’s country elegance. The open-concept living and dining area flows into a light-filled kitchen with floor-to-ceiling windows framing views of a mountain you own. The home features two nice-sized bedrooms and two full baths, offering comfort and practicality. Additional amenities include a large pantry/laundry room and easy access to a full concrete basement, ideal for storage or workshop space. Beyond the home, wooded trails lead to the back acreage and a hidden, spring fed pond perfect for secluded swims. There's subdivision potential, with 14+ acres already surveyed across the Grafton line—an investment opportunity or space to expand your vision. Perfectly situated between the charming villages of Chester and Grafton, this is more than a home, it's a lifestyle.

Not quite 20 years young, this charming custom-built colonial sits on a private knoll, surveying its 77+/- acre parcel. Blending country comfort and eloquence, you'll find quality craftsmanship throughout, such as blue stone floors and a stone archway. Wide plank floors lead to the country kitchen with soapstone countertops. Enter the spacious dining room with tray-beamed ceilings and oversized windows. A beautifully ballastered central staircase separates the main level. The living room features a masonry brick fireplace and built-in cabinetry. The house has radiant heat on the main level to combat cold winter days. The second floor features a primary suite with a soaking tub and a double sink. Bedrooms two and three share a 3/4 bath. On the top floor, you'll find a large finished space ready for your creativity. Over the two-car garage is office space or a bonus room, which is also accessed by a second staircase. The exterior offers a stone patio ready for summer BBQs or a new firepit for the colder months, and trails that crisscross the 77 acres. There are long-range views that can be opened. Located near the historic Chester Village and a short drive to Okemo, Magic, or Bromley. (acreage is enrolled in the Current Use Program for tax benefits). If you're looking for acreage, plenty of space, and privacy, don't wait to view this unique property. Visit the Okemo real estate community today. Taxes are based on current town assessment.