Properties Near 955 Smokeshire Road Chester, VT

Charming Country Retreat in Ludlow – Minutes from Okemo Mountain Don’t miss this rare opportunity to enjoy the peace of country living in the heart of Ludlow, a quintessential Vermont ski town and home to Okemo Mountain Resort. This meticulously maintained home has been lovingly cared for by the same owner for over 30 years. Designed for easy living, this move-in-ready property features high-quality, low-maintenance materials including cement composite clapboard siding, Trex decking, and a standing seam metal roof—ideal for those who prefer play over projects. Enjoy the spacious, sun-filled interior with an updated kitchen, open floor plan, expansive windows, and a cozy wood-burning fireplace—perfect for entertaining year-round. With three levels of living space, there’s room for everyone, plus added flexibility.The finished walkout basement offers potential as a separate living area—an excellent opportunity for rental income or guest accommodations. An oversized two-car garage and a separate shed provide ample storage for gear, tools, and toys.Whether you're looking for a full-time residence, weekend getaway, or investment property, this home delivers comfort, convenience, and Vermont charm in every season.

Perched on South Hill with sweeping views of the surrounding Vermont landscape, this authentic timber frame home offers the quintessential Green Mountain lifestyle on 10+/- private acres. Soaring exposed post-and-beam construction, tongue-and-groove cathedral ceilings, and rich hardwood floors flow throughout, giving the home a warmth and character that simply can’t be replicated. The open main level is anchored by a stone hearth and wood stove — the heart of the home on a crisp Vermont evening. The living and dining areas open seamlessly beneath an impressive timber truss system, while the kitchen features stainless steel appliances and dark stone countertops. A first-floor bath adds convenience. Upstairs, the timber frame continues to impress with vaulted bedroom spaces, loft potential, and views that remind you why you came to Vermont in the first place. The unfinished basement offers a blank canvas — workshop, additional living space, or storage. Outside, a classic red barn with two-car garage bays provides exceptional storage or hobby space, and the expansive deck is made for summer evenings with a view of the sunrise. The grounds offer room to garden, roam, and breathe. Minutes to Okemo Mountain Resort, downtown Ludlow dining and shops, and the crown jewel of Vermont four-season living. Visit the Okemo real estate community today. Taxes are based on the town assessment.

Tucked away on a quiet country road in one of Chester’s most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle—just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside, the main level centers around a commanding, floor-to-ceiling fieldstone wood-burning fireplace, beautifully complemented by rich hardwood floors and a bespoke custom kitchen. Designed for privacy, the primary suite features a spa-like ensuite bath, while two additional guest bedrooms and a 3/4 bath provide plenty of space for family or weekend visitors. Intelligently designed for flexible living, the upper-level loft serves as an inspiring home office or studio, while the bright, walk-out lower level offers incredible potential for a game room, home gym, or ski lounge. Transition effortlessly outdoors to the oversized front deck for morning coffee, or unwind in the expansive screened porch out back listening to the sound of the river. The detached 2 bay, 2 level barn offers extra storage space. There is a greenhouse perfect for gardening. With direct access to nearby VAST trails for winter recreation, this is a true four-season retreat. Visit the Okemo real estate today. Taxes are based on current town assessment.

Back on the market and drastically reduced! Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuites, 5 bath log home. The Great Room boasts a local stone floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is the perfect spot to game, watch TV or just chillax. Two ensuite bedrooms with private decks to take in the view of Hawks Mountain Range and the Black River. The attached two car oversized garage has enough room for cars and toys. A little TLC and a couple finishing touches and this house will be dynamite.