Properties Near 725 Flamstead Road Chester, VT

Once a tavern for travelers and a stagecoach stop in the early 1800s, 1607 Massey Road stands as a testament to Vermont’s enduring spirit. This distinguished 1810 Federal style home rests gracefully on over 48 acres of rolling meadow, woodland, and quiet pasture, offering a rare blend of seclusion, scale, and story. With more than 4,100 square feet of living space, the home welcomes you with generous rooms, wide fireplaces in the living room and bedrooms, and a sense of history in every beam and board. A classic kitchen with a center island opens to a breakfast nook bathed in morning light. Upstairs, a vast attic space invites conversion into a workshop, studio, or retreat beneath the eaves. Outside, a wide entertaining deck overlooks a tranquil pond and dock, where summer reflections stretch long into the evening. Beyond the main home, an old sugar house and barn wait patiently for revival and a return to their maple-making roots or transformation into event or creative spaces. A cabin at the summit offers income potential as a short-term rental or a quiet guest escape. From the hilltop, the views roll endlessly across the Vermont valleys below, a scene unchanged for generations. Private. Peaceful. Poised between past and possibility, this is a property that doesn’t just hold land and history, but the promise of legacy.

Beautifully maintained 2005 Contemporary Cape nestled on 6.7 private acres with sweeping long-range Vermont views. Owned and cherished by just one family, this move-in-ready home offers the best of country living with modern updates. The completely renovated kitchen boasts a Wolf range, Sub-Zero refrigerator, Bosch dishwasher, and quartz countertops, seamlessly flowing into the dining area—perfect for entertaining. The cozy living room features a wood-burning fireplace insert and opens via sliding doors to a multi-level deck with panoramic views. Enjoy peaceful mornings on the wraparound covered porch surrounded by nature. With 4 spacious bedrooms, including a serene primary ensuite, there's room for everyone. The finished walkout basement includes a large exercise room, office with wood stove, full bath, and guest bedroom. Recent upgrades include Brazilian rosewood flooring upstairs and a whole-house Kohler generator. The extended one-car garage includes a full workshop space. Paved driveway for easy maintenance. Outside, explore walking trails, tap 14 mature maple trees, or harvest blueberries and strawberries from your own garden. Only minutes from Chester’s charming town green—this is Vermont living at its finest. OPEN HOUSE SATURDAY OCT 11TH 11:00AM TO 2:00PM

Welcome to this spacious and beautifully expanded Gambrel-style home, set on a stunning 9.55-acre property with mountain views in the heart of Springfield, Vermont. Offering classic New England charm with thoughtful modern upgrades, this property is not just a home, but a contemporary and comfortable living space. The main home, built in 1955, was expanded with a large addition in 2009, including an upstairs luxurious primary suite featuring a private bath and a generous walk-in closet that walks out to balconies on either side of the oversized loft with wall to wall windows to capture every bit of natural light into the livingroom and kitchen space below. The vaulted ceilings and oversized windows welcome you, showcasing beautiful views of the surrounding mountains and area. The heart of the home is the comprehensive kitchen—perfect for cooking, entertaining, and everyday living—with expansive counter space, abundant cabinetry, and an immense island; there's room for everyone! The land itself is a dream for nature lovers and hobby farmers alike. A full 1-acre section is dedicated to a pick-your-own blueberry patch, offering a charming seasonal activity and potential for small-scale agricultural income. The property includes a second modular home with a full foundation and a basement, adding even more value. Currently rented, no photos at this time. Other things to note are the hook-ups for a whole-house generator and a quaint barn for storing farming equipment.