New Listings for Sale in Chester, VT

New Listing for sale in Chester, VT:

Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom-built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one-acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Inside, the layout balan

New Listing for sale in Chester, VT:

Quintessential 1880s Vermont farmhouse in bucolic Weston. Nestled on 7 private acres, this 4 bedroom, 3 bath retreat offers authentic pine floors, historical charm throughout with a tranquil pond greeting you upon arrival. It is the perfect blend or timeless character and rural serenity. BRAND NEW DRILLED WELL & MOUND SEPTIC SYSTEM just installed in August 2026. Updated electric makes this house ready for the next steward. The kitchen is authentic and you may choose to update. Situated in the picturesque town of Weston, one of Southern Vermont's most coveted historic villages. The village is home to the iconic Vermont Country Store and the renowned Weston Theater Company. The large sw

New Listing for sale in Chester, VT:

Brand-new construction in Springfield, Vermont! Offering approximately 2,100 sq. ft. of bright, thoughtfully designed living space, this 3-bedroom, 2-bath home combines modern comfort, energy efficiency and low-maintenance living with an open, single-level floor plan. Large windows allow natural light to flood the home, while the spacious kitchen, dining and living areas come together in an inviting open-concept great room designed for both everyday living and entertaining. Built for today's lifestyle, the home features a high-efficiency propane boiler, 200-amp electrical service and fiber-optic internet for reliable high-speed connectivity. Three comfortable bedrooms provide flexibility fo

New Listing for sale in Chester, VT:

45 Trailside Road offers the ideal combination of mountain living, generous indoor space, and exceptional outdoor living on Okemo Mountain. This distinctive mountain home welcomes you through a spacious mudroom with barnboard details and ample space for four-season gear. Beyond, natural light fills the open kitchen, dining, and living areas, creating an inviting space for gathering. The well-appointed, custom kitchen features cherry cabinetry, stainless steel appliances, an oversized island, a cozy breakfast nook, and easy access to the expansive deck. Outdoor spaces are a highlight, including a large curved deck overlooking the private, wooded backyard, a covered porch perfect for grilling

New Listing for sale in Chester, VT:

Seller says please excuse the boxes, I'm busy moving! Well cared for 3BR/2BA home located on a quiet, mostly level country lot. Home features an eat-in kitchen, formal dining room, large living room with gas fireplace, large laundry area, first floor bedroom and bath so it could be one floor living. Second floor features two nice sized bedrooms and a full bath. Floors are a mixture of hard and softwood with vinyl in kitchen and baths. Newer windows, vinyl siding and a metal roof make for easy maintenance. One car attached/under garage for storage. Spend your summertime on the large deck. A reasonably priced home in a sought-after township. This home will be a busy one. Schedule your tour t

New Listing for sale in Chester, VT:

Stunning Contemporary on 7.6 acres - Sunny, Bright, and beautifully designed, this gorgeous home showcases exceptional quality workmanship, thoughtful details and wonderful connection to outdoors. A Gracious entrance lined with Pear and Cherry trees on this paved circular driveway with center planting beds with seasonal blooming plants ( roses, hosta lilies, sunflowers, hydrangeas) and beautiful stonework, creating an impressive first arrival. Inside the heart of the home is the spectacular kitchen, featuring custom cabinetry, granite countertops, country sink and gorgeous Elmira retro stove. The kitchen flows seamlessly into the dining and living ares with Oak floors, soaring vaulted ceili