Properties Near 176 Meadow Road Chester, VT

Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with butcher block counters, attractive center island with Vermont slate/stone counter, stainless steel sink and dishwasher framed by a wall of windows with a picturesque valley view. A spacious first-floor bedroom, full bath and convenient laundry area provide easy one-level living. Upstairs, two additional bedrooms with generous closets share a stylish full bath finished with classic subway tile. Recent upgrades include energy efficient systems and a new four-bedroom leach field, offering peace of mind for full-time residents, second-home owners, or investors. Offered fully furnished, this turnkey Vermont property has a proven history as a successful seasonal rental. Experience the vibrant community of Chester, with its charming village shops and restaurants, town pool, recreation area, premier disc golf course, pickleball and tennis courts, snowmobile club, and thriving artisan culture. Ideally located near Okemo Mountain Resort and Magic Mountain ski areas. This quintessential Vermont home is equally suited as a primary residence, ski getaway, vacation home, or income-producing investment property.

MOTIVATED SELLERS just adjusted the price significantly!!! Sweet property with 7.5 acres, great pond, quiet setting and private. This could be your escape to your own peaceful, 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 second floor bedroom also enjoys a deck to enjoy the view and wildlife. 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, heated, for those cool nights, and also an attached work shed, for all the woodworking or hobbies one might enjoy, as well as 1/4 bath for convenience. 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 perhaps use as a guesthouse or Air B&B. The pond is a bonus and ready for enjoyment during the summer months. The property is located with easy access to Springfield and Chester for all your shopping, medical and recreation needs. Hiking, golfing, skiing, entertainment, movie theatre, arts and more.

Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area that works just as well for casual dining as it does for a home office setup. The dining space flows easily into a sunken living room, where the pellet stove becomes a natural gathering spot. Two bedrooms on the main level, each with their own bath, make this a great fit for a variety of living situations. Upstairs, you’ll find a spacious bedroom, a separate flex room currently used as a movie room, and an unfinished bonus area ready for whatever you have in mind. Storage is not an issue here, between the closets and full basement, there’s plenty of space to keep things organized. The home is equipped with a new furnace and four heating zones, offering efficiency and control throughout. Outside, a wide back patio gives you a great place to relax, while the barn and oversized three-bay garage offer serious utility for storage, equipment, or hobbies. The detached garage is currently rented for $500 per month, and the tenant would be open to continuing that arrangement with the next owner. The property borders Lovers Lane Brook, adding to the natural setting and privacy, all just minutes to Chester’s shops, dining, and village amenities. If you’ve been looking for an in-town property with more space and versatility than most, this one is worth a look. Furnishings are negotiable for anyone looking for a truly turn-key property!

Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning fireplace and a large entertainment room complete with a wet bar, creating an ideal setting for gatherings, celebrations, or relaxing at home. The thoughtfully designed primary suite features a beautiful en-suite bathroom, while first-floor laundry adds everyday convenience. The flexible floor plan provides abundant space for family, guests, remote work, hobbies, or multi-generational living. Outside, a paved driveway leads to a detached one-car garage, and the level backyard offers plenty of room for recreation, gardening, pets, or outdoor entertaining. Mature trees and established landscaping create a natural buffer from the road, providing a sense of privacy while remaining just moments from Chester's village amenities, shops, restaurants, and community events. Combining historic character, generous living space, and a highly desirable location, this is a rare opportunity to own one of Chester's classic homes. Conveniently located just minutes from I-91 and within easy reach of Okemo Mountain Resort, Magic Mountain, Bromley Mountain, Stratton Mountain, and other Southern Vermont outdoor destinations, this property offers year-round access to skiing, hiking, recreation, and travel throughout the region.

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.

Welcome to this beautifully updated raised ranch, thoughtfully designed for both relaxed day-to-day living and effortless entertaining. Step inside to an open-concept main level bathed in natural light, anchored by rich hickory hardwood floors that flow throughout. At the heart of the home, the renovated kitchen shines with modern finishes, a classic apron-front farmhouse sink, and stainless steel appliances. Relax by the gas fireplace in the inviting living room, highlighted by soaring vaulted ceilings and rustic exposed wood beams. Accommodating family and guests with ease, the layout features 5 generous bedrooms and 2 updated baths. The primary suite acts as your own private sanctuary, complete with an ensuite bath featuring a double vanity, and a private balcony. The flexible lower-level bonus space easily adapts to your lifestyle - ideal for a home gym, media room, or private office. Outdoor living is a breeze while you're relaxing bug-free on the screened porch! Tucked away on a quiet dead-end street, this turn-key residence pairs privacy with convenience with an easy walk to the vibrant Chester Green. Additional highlights include the boiler replaced in 2021, the freshly painted interior in 2022, new windows installed throughout the house in 2021 and 2025, a new sump pump installed in 2023, and a newly paved driveway in 2024. Electrical updates and a full foundation restoration have been completed in 2026 for long-term structural integrity (inquire for more information or see under Attached Documents), providing peace of mind for years to come. 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.

Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester’s Stone Village, the Grist Mill, and Smitty’s Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals.