Properties Near 514 First Avenue Chester, VT

Charming Renovated Farmhouse in the Heart of Chester This beautifully renovated farmhouse sits on a level half-acre lot just steps from Chester’s Village Green, shops, and local amenities. Offering the perfect blend of historic charm and modern updates, this 4-bedroom, 3-bath home is ideal for year-round living or a Vermont getaway. Inside, enjoy a spacious kitchen with custom pantry shelving, a convenient first-floor laundry room and cozy mudroom. Two main-floor bedrooms provide flexible living options. The second level has a cozy 3rd bedroom and 3/4 bath plus the luxurious primary suite boasting a brand-new custom bathroom with a soaking tub, oversized steam shower, walk-in closet, and a peaceful sitting area. Outdoor living is equally inviting, with a covered wrap-around porch, screened porch opening to a stone patio, and a tranquil Zen garden. A vegetable garden awaits your green thumb, and the small attached barn offers extra storage or workshop potential. A newly added one-car garage and whole-house generator completes the package. Conveniently situated within 15 minutes of Okemo or Magic Mountain, and under 30 minutes to Bromley and Stratton—this is Vermont living at its best!

You have got to see this stunning, fully renovated home, rebuilt from the studs up with meticulous attention to detail while maintaining its classic New England charm! Perfectly perched on the picturesque rolling hills of desirable Chester, this 4bdrm, 3bath beauty offers the ideal balance of comfort, elegance, and modern functionality. Set on 6 private acres overlooking open fields and peaceful pastures, this home is designed to take full advantage of its breathtaking surroundings. Step inside and you’re greeted by a spacious, sun-filled kitchen and dining area where large windows frame panoramic views of the countryside. The easy flow and layout blends seamlessly, perfect for entertaining friends, hosting family gatherings, or simply relaxing by the warmth of the Vermont seasons. The 1st floor primary bedroom, 3/4 bath, and laundry room offer an ideal layout for aging in place. Upstairs, you’ll find a primary en suite, 2 addtl bdrms, and a full bath, giving everyone their own space and privacy. A full basement provides excellent storage, hobby, or workshop space. Every aspect of this home has been thoughtfully reimagined, from the quality craftsmanship to the modern finishes, offering a true turn-key living experience in one of Vermont’s most desirable locations. Outside, enjoy six acres of serene land with plenty of room for gardens or outdoor recreation. Easy access to skiing, hiking, biking, and endless outdoor adventures, I-91, Dartmouth Hospital and more.

Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal dining room for holiday dinners, 2 connecting living spaces with fireplace, a bedroom and a full bath. Upstairs are 3 more bedrooms and a full and half bath. The character and antique doors and trim make this house a home. The carriage house unit has 3 bedrooms, a kitchen and full bath and a large open great room and is perfect for guests. There are also more areas with potential - two more levels of barn space plus the attic. Outside you will find a large covered porch, a level back yard for games, and the Williams River down at the back of the property. Sold turnkey. Be the 4th family to own this home since 1868 and see why Chester has been voted one of the top 10 most beautiful towns in Vermont! Discover the tasty food options, pubs, antique shops, art galleries, yoga & pottery studios, and a country market with great sandwiches, fresh meats and produce. Experience Vermont - hiking trails, world class skiing, farms, refreshing rivers, restaurants, breweries and more. Be close to the best of Vermont's ski resorts! (Okemo, Killington, Stratton, Bromley, and Magic Mountains).

Discover the perfect balance of privacy, convenience, and sustainable living in this artisan-designed post and beam home. Thoughtfully sited on 10 acres at the end of a country road, this 3 bedroom, 3.5 bath farmhouse offers a rare sanctuary just a short stroll from the charming village center. Designed for today's lifestyle, the home is equipped with solar power and battery backup, ensuring energy efficiency and seamless functionality. The inviting open-concept layout features a modern/rustic kitchen with concrete counters and butcher block island and a free standing brick hearth that warms the living and dining areas. A first floor bedroom/study has a large, private bath with walk-in tiled shower steps away from the studio/exercise room with concrete flooring and a cozy loft. Upstairs, you’ll find playful architectural details such as a whimsical, window-paned hallway partition that leads to the chic primary ensuite bedroom with laundry, 2 additional bedrooms, custom built-ins and an additional full bath. Enjoy the beauty of Vermont from the large screened porch with tiled floor overlooking wildlife and natural surroundings. The garden has a frost free pump, raised beds, pear and peach trees and nearby are two unique vernal, seasonal pools. Modern conveniences include high-speed fiber optics for remote work and a handicap ramp for easy accessibility. This one-of-a-kind residence offers privacy, craftsmanship and connection to nature all within minutes to town.

Tucked along a quiet country road, 197 Baker Road stands as a living piece of Vermont’s history. A sturdy 1835 home that has weathered time with grace and care, set on over 80 acres of fields, woods, and pastures, this property opens like a storybook of rural life: a large pond mirrors the changing sky, trails wind toward the hilltop with sweeping views, and smaller ponds shimmer between trees where deer and other wildlife pass. Inside, light pours into the spacious living room and sunlit kitchen, where a center island invites conversation and comfort. The home’s craftsmanship endures, strengthened by thoughtful updates, including 200-amp electrical service, a renovated mudroom, and spaces ready to evolve with your vision. Off the basement, a hidden tunnel and fallout shelter whisper of the home’s storied past, adding intrigue to its enduring charm. There is room here for homesteading, gardening, hiking, or snowmobiling across your own land. An outbuilding waits to store tools or fuel creative pursuits, and a flex space offers potential for a workshop or studio. Despite its privacy, you are only minutes from town conveniences, the Upper Valley, and world-class ski areas. This is a home where Vermont’s beauty and history meet in everyday life.

Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports both daily living and gathering. The large living room, anchored by two fireplaces, is a natural place to slow down. A formal dining room is ideal for hosting, and a generous room off the kitchen easily accommodates larger meals and celebrations. Original wood floors, exposed beams, and durable early craftsmanship add character throughout. A separate rental unit, currently occupied, provides steady income or flexible use for guests, family, or workspace. The barn offers storage, workshop potential, or agricultural use, expanding what the property can support. Chester’s shops and everyday conveniences are close by, and skiing, rivers, and trails are within easy reach. Okemo is just minutes away, with Stratton, Magic, and Bromley all within a short drive of 20-30 minutes. Several AT access point within similar distance. The Okemo Valley is on your doorstep, and it's magical! This is a historic home ready for its next chapter—solid, adaptable, and full of possibility. Come See Today!!