Tucked away at the end of a quiet lane on three scenic acres, this well-maintained home offers a rare blend of privacy, versatility, and proximity to town. Set against the backdrop of the Williams River, the property delivers a peaceful setting with year-round interest: mature apple trees, open lawn, and seasonal views best enjoyed from the expansive back deck. Inside, over 2,500 square feet of living space is designed to adapt to a variety of needs. The vaulted-ceiling living area is filled with natural light from custom windows and anchored by a wood-burning stove, creating a warm and inviting central gathering space. Sliding doors connect seamlessly to the outdoors, making indoor-outdoor living effortless. The spacious kitchen features a generous pantry and flexible dining area with picturesque views of the property. The main level also includes a mudroom entry, laundry, a bedroom, and a three-quarter bath, ideal for single-level living, guest space, or a private office setup. Upstairs, additional bedrooms and a full bath provide comfortable separation of space, including a large primary bedroom. The finished lower level expands the home’s functionality with a rec or media room, ample storage, and a walkout room well-suited for a workspace, studio, or fitness area. A two-car garage with breezeway access adds convenience, while the partially finished upper level offers even more potential for creative or practical use. A unique opportunity to enjoy a tranquil setting with flexible spaces to live, work, and unwind, just minutes from the heart of Chester.
Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam board, and the foundation is sealed with full drainage installed around the perimeter. Step inside to a light-filled interior with new flooring, walls, and fixtures throughout. The spacious kitchen features Big Chill appliances and opens to a lovely front porch overlooking the old stone walls that border the property. A fenced-in yard makes this ideal for pets, and the water filtration system with UV light ensures clean living. You’ll also find a new washer and dryer, a new septic system, and thoughtful design throughout. Close to skiing at Magic (10 min), Bromley and Stratton (20–25 min), and just 15 minutes to downtown Londonderry. Hike, bike, or snowmobile with access to VAST trails and Timber Ridge nearby. Come see what makes this rare offering a great opportunity!
Mountain Escape with Multi-Generational Potential in Powder Mill Welcome to your mountain retreat in the heart of Vermont’s ski country! This spacious home in the desirable Powder Mill community has been thoughtfully updated with brand new kitchen cabinets, gleaming granite countertops, stainless steel appliances, and fresh carpet and flooring throughout. The flexible layout offers room for everyone: a fully furnished apartment on the first floor is ideal for guests, in-laws, or rental income, while the main living space upstairs features comfortable family areas, loft-style bedrooms, and a bonus bedroom over the garage. Whether you’re looking for a primary residence, vacation getaway, or investment opportunity, this home is perfectly positioned just minutes from Lowell Lake and Magic Mountain, with easy access to Stratton, Bromley, and Okemo resorts. Powder Mill is a unique community designed for outdoor enthusiasts, offering direct access to hiking trails, snowmobile routes, scenic ponds, and a welcoming neighborhood feel. Don’t miss the chance to tour this one-of-a-kind property and experience the lifestyle for yourself!
Welcome to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, yet close to skiing, VAST and amenities. So many updates in the past two years, modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is a true move in ready beauty. The owners are leaving this home furnished, making this a true turnkey property. The rooms are nicely sized and in close proximity to bathrooms. This has been used as a vacation property and has a history of successful Airbnb. The wood burning fireplace brings a feeling of serenity on those chilly days. Fiber internet on site for those that work remotely. Town records state two bedrooms, however, the loft area has a sleeping quarter with a bathroom! Plenty of storage, full walkout basement gives ample space. This is one of those properties you won’t want to miss on your home buying adventure! Truly a stunning property with so much to offer!
Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a town-maintained road and plowed right to your door, is ready for a complete restoration. Its form and orientation make it an ideal candidate for renovation, preserving the rural character that defines this part of Vermont. Several original outbuildings remain, including a tall silo, classic barns, and a sugarhouse—all reminders of the land’s agricultural roots. Power and utilities are in place, and the road frontage provides easy access in all seasons. This is a solid opportunity for someone looking to rebuild, reimagine, or create a homestead with scale and history. Located between Chester, Weston, Londonderry, and the Okemo Valley, it offers both privacy and proximity to year-round recreation.
The Best of Both Worlds: Modern Comfort Meets Village Charm! Discover the perfect blend of contemporary upgrades and serene neighborhood. This meticulously updated raised ranch offers an expansive layout designed for both effortless entertaining and comfortable daily living. Step inside to find a light-filled open-concept living and dining area, anchored by stunning hickory hardwood floors that flow throughout the main level. The heart of the home is the fully renovated kitchen, featuring modern finishes, apron front farmhouse sink and outfitted with stainless steel appliances. With 5 spacious bedrooms, 2 updated bathrooms, there is no shortage of space. Enjoy cozy evenings in the living room featuring a vaulted ceiling and exposed wood beams and a gas fireplace. The primary suite serves as a retreat complete with a private balcony, and an ensuite bath featuring a double vanity. On the lower level, a large bonus room provides the flexible space you’ve been looking for-ideal for a gym, playroom or office! Enjoy the fresh air without the bugs in your screened-in porch, or host summer gatherings in the peaceful yard. Located on a quiet dead-end street, this home offers privacy while remaining incredibly convenient. Additional highlights include an easy walk to the vibrant Chester Green, peace of mind with a new boiler in 2021, freshly painted interior in 2022, sump pump installed in 2023, a 1 car garage, a paved driveway done in 2024, and new windows installed throughout most of the house in 2025. Don't miss your chance to own this move-in-ready gem in a prime Chester location!
This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom.
Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below—perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there’s room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery—rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont’s natural beauty. A property that offers privacy, water frontage, land, and mountain access—without giving up convenience.
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