Properties Near 176 Meadow Road Chester, VT

Welcome to your own peaceful, private homestead. Set on 7.5 acres of wooded and open land this property is truly a respite from the stresses of the world. This multi-level 3-bedroom, 3 bath home offers convenience and options. The spacious living room with hardwood floors leads to a large eat-in kitchen with ample storage and room for an island if desired. Step into the Family room or a large dining room with access to one of the decks overlooking the pond. The primary bedroom on the third level has a convenient 3/4 bathroom as well as a deck to again enjoy the views of wildlife and the pond. An additional bedroom also enjoys a deck to enjoy the view. A full bathroom is convenient on level 3. On the lower level a large family/game room awaits with a wood stove to keep you warm on those chilly nights and offers full access to the back acreage. In addition, a 3rd bedroom and full bath/laundry room make this a true family home. Wait, there is more, an oversize 2 car garage with an attached work shed for all the woodworking or hobbies one might enjoy. Over the garage an open concept apartment features living room, kitchen, 1 bedroom and bath. It has been used as a rental, which one could continue or use as a guesthouse. The property is located with easy access to Springfield and Chester for all shopping, medical and recreation needs,

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.

Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you’ll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potential for additional living space, a workshop, or studio. Outside, enjoy your private fenced backyard with garden space, a fire pit, and even a bar area — perfect for entertaining family and friends. This inviting village home combines charm, functionality, and opportunity — come experience all that Chester has to offer! Visit the Okemo real estate community today. Taxes are based on current town assessment.

Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the gorgeous hardwood floors that add warmth and character to every room. Bask in the great natural light that fills every corner of this lovely abode, making every day feel bright and inviting. This home includes a main level bedroom, dining room and family room. In addition there is an attached garage and a barn for all your hobbies. This home is perfect for families and outdoor enthusiasts alike. Imagine being just a short stroll away from the village store for all your essentials and enjoying nearby skiing adventures in winter, along with shopping and restaurants year-round! Don't miss out on this incredible opportunity to own a piece of paradise in the heart of it all! Schedule your visit today and get ready to fall in love – your perfect home awaits!

Welcome to a charming village retreat in the heart of Chester, perfectly situated on Main Street in the historic Chester Stone Village. This inviting home blends classic Vermont character with comfortable, year-round living. Enter through a practical mudroom with ample space for all your seasonal gear—ideal for embracing Vermont’s four-season lifestyle. To the right, at the front of the home, you’ll find a bright and open living space featuring a spacious kitchen with a large island, seamlessly connected to the dining area and living room. A glass door leads to a covered porch, creating the perfect spot for morning coffee or relaxing evenings. The main level also offers a dedicated office, a full bathroom, and a convenient laundry room. Toward the back of the home, two bedrooms provide comfortable accommodations, and a stunning family room showcases vaulted ceilings, exposed beams, and walls of windows that fill the space with natural light. A glass slider opens to the back deck, where you’ll find an above-ground pool—perfect for summer enjoyment. Experience the charm of Vermont living in this village home, just moments from local shops, dining, and all that Chester has to offer. Visit the Okemo real estate community today. Taxes are based on town assessment.