Chester, VT | 302 Davidson Hill Road

$354,000
MLS#: 5102316
900
Sq Ft
11
Acres
1
Baths
2
Bedrooms
Restore Properties
Take a look at this gorgeous custom home, built by a well-known and respected contractor for his family about 10 years ago. A beautiful property that is waiting to welcome another owner to enjoy what this family has for several years. Now owning this wonderful property can be your opportunity. The house has lots of room for a large family, with 4 bedrooms and 3 baths! A kitchen to satisfy the most discriminating cook, with an open concept featuring a spacious dining room which can be extended into the living room for family gatherings. Off from the living room you'll find a full length farmer's porch with room for a table and chairs, giving you more room for entertaining, or just a nice quiet place to enjoy summer evenings! You'll be very happy with the custom woodwork and workmanship throughout this beautiful home. For anyone wanting a garage and even room for a small apartment, there is a huge garage that features a professional vehicle lift. A large stairway takes you up to an open area that could be made into space for a home office or even a guest apartment. This is a great opportunity to purchase your dream home at a reasonable price!
Tucked into the charming village of Perkinsville on 3.8 acres, this unique residential and commercial property offers the perfect balance of opportunity, lifestyle, and connection. You will be moments away from Stoughton Pond, hiking trails, and within driving distance to some of Vermont’s most sought-after ski resorts. For years, this property has been a gathering place—Saturday nights around the kitchen table, laughter filling the home, and a trusted shop where neighbors came not just for service, but for connection. Now, it’s ready for its next chapter. One level home of comfortable living, with an open-concept kitchen, dining, and living area designed for both everyday life and easy entertaining. 3 bedrooms and 2.5 baths provide flexibility, including a primary bedroom with an oversized closet. The enclosed, heated front porch offers additional living space and convenience, complete with a washer and dryer. The walk-out basement expands the possibilities. Ample ceiling height, workshop area, second laundry setup, ¾ bath, and a bonus room ideal for an office or creative space is a functional extension of the home. A classic Vermont touch—the built-in dumbwaiter—makes bringing firewood upstairs simple and efficient. The 2 story garage/shop stands ready for its next purpose, featuring multiple bays with car lifts, high ceilings, heat, and a half bath. Additional outbuildings with concrete floors and covered storage areas provide ample room for equipment, tools, recreational vehicles, and more. A property with this kind of flexibility, history, and heart doesn’t come along often. Bring your ideas and your creativity—and make it your own. Sellers are submitting elevation certificate to FEMA to be removed from flood plain map.
Welcome to a truly special Vermont property where craftsmanship, comfort, and the beauty of the outdoors come together. Offering over 3,000 square feet of beautifully renovated living space, this distinctive home is filled with custom features and exceptional woodworking throughout. The heart of the home is the custom kitchen, featuring rich cherry cabinetry and timeless soapstone countertops, complemented by numerous thoughtful updates. With four bedrooms, there is plenty of space for family and guests. The beautifully renovated primary bath offers a luxurious retreat with a stone and tile walk-in shower and a Jacuzzi soaking tub. Set on two picturesque acres, the property offers a peaceful Vermont setting complete with a babbling brook, mature perennial gardens, and ample space for additional gardening. Two fully functional workshops provide exceptional space for woodworking, hobbies, storage, or other creative pursuits. Located in a quiet neighborhood yet conveniently close to schools, the hospital, Route 91, and Okemo Mountain, this property puts year-round outdoor recreation and everything Vermont has to offer within easy reach. Whether you're looking for a beautifully crafted home, a gardener's haven, a workshop enthusiast's dream, or simply a peaceful place to call home, this one-of-a-kind property is ready to welcome you.
No words describe this property better than peaceful, rural, convenient and historic. Throughout its long life, the top of Elm Hill exudes country. The rugged stone walls, lower barn, tool shed and upper barn reveal an agricultural past. The upper barn has been converted to a 2-car garage and workshop, complete with a half-ton hoist. The upstairs hayloft (attic type storage) is easily accessible by stairs in the back and double doors on the front. The carriage port has been enclosed to store wood for the Defiant woodstove in the sitting room, adjoining the kitchen. On the south side are a five-tree apple orchard and a garden plot each producing for residents and neighbors alike. Sunshine and natural light define the yard, the views and interior, Foundation plantings thrive in the morning sun. The back hills and fields light up in midday and evening sun. During foliage, the hills across the valley blaze in the sunset. Multiple windows flood the house interior with natural light. Convenience doesn't negate peace. A mere mile from the town central square, where one will find a variety of unique shops, restaurants and even a movie theatre. The house is but a 1.1 mile from the shopping plaza and 1.5 miles from the hospital and with a golf course, ski areas and multiple hiking venues nearby, one can easily get back to nature. In the early morning and evening turkey and deer come from the back hill to feed in the adjoining meadows as well as a variety of colorful songbirds to enjoy. A classic post and beam 4 bedroom, 2 bath home on 1.2 acres was built by James Litchfield when he settled the top of Elm Hill. The original axe-cut post and sturdy beams exposed on the main floor living room, dining room and office attest to its structure and history. Since the first family made this their home in the early 1790s, it has sheltered and nurtured eight families of several generations each. Yours can be the next family to make history here. Come experience the peaceful setting.
If you're looking for your forever home or the perfect mountain getaway, take a peek at this locally built Green Mountain Log Home. Davidson Hill Road is home to many craftsman quality homes perched above Chester, overlooking Mt. Ascutney. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical wooden clad bedrooms make up the second floor. The home has a new roof, new on-demand hot water system, fresh stain on the log exterior, updated electrical, and brand new LVL carrying beam and floor joists in the basement. Many other practical upgrades and extensive landscaping has been made and this home is in mint condition. The sellers recently did a drinking water test, had the septic pumped, and did a home inspection, leaving no stone unturned. The 11 acre parcel transitions from a large sunny open yard to old stone walls and hemlock-hardwood forest and rises nearly to the humble summit of Davidson Hill (1053' elevation). The owners let a neighboring property tap most of the maple trees in exchange for maple syrup. The house is located just feet from Trail #5 of the Hawks Mountain Ridge Riders VAST trail network, and is minutes from downtown Springfield and Chester. Just 15 minutes from I-91 and Okemo. While surrounded by forest and situated for optimum privacy, this home does have seasonal views of Mt. Ascutney and there is a good possibility of spectacular views higher up on the property. The height of the property would make an awesome camping or gazebo spot. Many logging roads and four wheeler trails throughout the property. The dog on the couch does not convey.
Price improvement plus a new septic leach field! What a sweet historic home just waiting for the right person to give it some TLC to bring it back to its beautiful original state! The house is very straight and solid, so that anyone can easily live in it as they do the cosmetics to their personal taste. Attached to the main body of the house is a very nicely done and spacious in-law apartment with handicap ramp. The apartment has one bedroom; the main house has four bedrooms. They are seamlessly connected though so that if anyone needs all of the space for a large family, no problem! The grounds are really nice, very private with lots of flowers and garden areas. There are two outbuildings including an old chicken coup that was finished into three rooms years ago - with work the possibilities are many. There is also the original 2-car garage that was finished into a living area many years ago. Not really habitable now, but with work it would make a great rental unit, long or short-term. Or, you can turn it back into the garage. Plus, you will even find the kid's old playhouse. All of this with a private lot and yet located within a mile of the shopping plaza, schools, and Springfield Hospital.
Move-in ready and lovingly maintained, this charming Cape-style home offers 3 bedrooms, an office/laundry room, 1 full bathroom, a spacious eat-in kitchen, a 2-car garage, and a large back deck perfect for relaxing or entertaining. The backyard abuts the Springfield Dam, providing beautiful views of Hawks Mountain and Mount Ascutney while offering close access to nearby nature preserves and walking trails. Enjoy the flexibility of heating with either oil or the efficient pellet stove. Outside, you'll find a level, open yard with a fenced area for dogs, creating an ideal space for both pets and outdoor enjoyment. Conveniently located close to Springfield amenities, yet just a short drive to Weathersfield, Claremont, and I-91, this well-cared-for home offers the perfect balance of comfort, convenience, and natural beauty.
Perched on a hill in one of Springfield's most desirable neighborhoods, this well-maintained home offers a peaceful setting just minutes from downtown amenities. Tucked away from the hustle and bustle, 6 Juniper Hill Road has been lovingly cared for over the years and is ready for its next chapter. The flexible layout offers four bedrooms and two bathrooms, making it ideal for a variety of living arrangements. The lower level features a bedroom, a ¾ bath, laundry area, and direct access to the attached two-bay garage, creating an excellent setup for guests, extended family, or anyone seeking first-floor living options. Upstairs, you'll find three additional bedrooms, a full bath, along with comfortable living, dining, and kitchen spaces that flow nicely together. The recently renovated kitchen is a standout, featuring beautiful stone countertops and a fresh, updated feel that's ready for everything from busy weekday meals to holiday gatherings. The upstairs bathroom renovation has already been started, but the contractor was unable to complete the project. To help the next owner finish it to their taste, the seller is willing to work with buyers on mutually acceptable terms for completion after closing. One of the home's most inviting spaces is the spacious three-season screened porch with its gorgeous slate floor. Whether you're grilling dinner, enjoying your morning coffee, relaxing with an evening drink, listening to birdsong, or watching a summer thunderstorm roll through, this space is sure to become a favorite. Outside, the large lawn provides plenty of room for pets, games, gardening, or simply enjoying the outdoors. The attached two-bay garage keeps vehicles protected from Vermont's weather while adding valuable storage and convenience. If you've been looking for a home in a quiet, established neighborhood that offers space, thoughtful updates, and an outstanding location just outside the center of town, 6 Juniper Hill Road is one you won't want to miss.
A classic Vermont farmhouse with space, flexibility, and possibilities for the future. Currently enjoyed as a spacious single-family home, the layout offers clear potential to adapt for multi-generational living or a two-family configuration with modification. For those with a bigger vision, the substantial rear barn and workshop areas may offer further possibilities, subject to permitting and approvals. Inside, generous rooms and abundant natural light create a warm, comfortable feel throughout. The main level features inviting living and dining spaces and an updated eat-in kitchen. The home has benefited from numerous improvements, including a new roof, new wood and pellet stoves within the past two years, a whole-house dehumidifier, and a long list of cosmetic updates that have refreshed the property while preserving its traditional farmhouse character. Upstairs, additional living space provides flexibility for bedrooms, office space, guest quarters, or a more independent living arrangement. The attached workshop and rear barn spaces offer excellent room for hobbies, storage, a home-based workspace, or future reimagining. Outside, the level one-acre lot is a true highlight, with mature perennial gardens, open lawn, and a picturesque brook running along the property, complete with a small private beach area. Set in the heart of North Springfield, this is a property with room to live, work, create, and evolve.
Seller says please excuse the boxes, I'm busy moving! Well cared for 3BR/2BA home located on a quiet, mostly level country lot. Home features an eat-in kitchen, formal dining room, large living room with gas fireplace, large laundry area, first floor bedroom and bath so it could be one floor living. Second floor features two nice sized bedrooms and a full bath. Floors are a mixture of hard and softwood with vinyl in kitchen and baths. Newer windows, vinyl siding and a metal roof make for easy maintenance. One car attached/under garage for storage. Spend your summertime on the large deck. A reasonably priced home in a sought-after township. This home will be a busy one. Schedule your tour today.
Extremely well maintained and thoughtfully updated, this spacious three bedroom, two and a half bath home is privately nestled on 2.6 acres on a quiet dead end. Offering the convenience of single level living, the property has been meticulously cared for over the years, with numerous improvements that make it comfortable, efficient, and move in ready. Inside you’ll find generously sized rooms throughout, offering plenty of space for everyday living and entertaining. The home features a primary suite with its own private full bathroom with a soaking tub, two additional good sized bedrooms, another full bath, and a convenient half bath. The functional single level layout makes the home easy to enjoy, while the main living areas offer plenty of natural light and comfortable gathering space. The home has seen an impressive list of recent updates, including new kitchen flooring in 2021, a new roof and skylights in 2022, newer kitchen appliances, and a mini-split system installed in 2023. Additionally, a new hot water heater in 2025. Set on 2.6 acres, the property offers a peaceful and private setting while still providing convenient access to Chester and the surrounding area. With its spacious rooms, primary suite, 2.5 baths, single level living, extensive recent improvements, and exceptionally well-maintained condition, this is a home that has been cared for with attention to detail and is ready for its next owners to enjoy.
This recently refreshed property features a new roof, siding, electrical panel, furnace and oil tank as well as fresh paint, updated kitchen and bathroom. The convenient corner lot location is open and level for great lawn space and opportunities for maybe some gardens or play space. The detached 2 car garage provides additional storage space and a great place to get your vehicles out of the weather. Overall this is a great opportunity for the right buyer!
GOOD NEWS! A newly renovated, affordable, well maintained home for a reasonable price! Ask your agent for the list of improvements. It is expected that this home will EASILY MEET GOV'T LOAN FINANCING. This attractive home has easy access to downtown, shopping, parks, ski slopes, mountain hiking, river walks, interstate, and quiet living. The pleasantly comfortable yard offers reasonable privacy for outdoor gatherings, gardening, or just a place for peaceful thinking. The home has had many recent upgrades. The extensive list is available upon request. The utilities have been well maintained. The basement is partially finished, which could be added to the square footage of the home.
Charming, cozy and warm, this 1940 cape has a lot to offer you! With 3 comfortable bedrooms with good sized closets and a full bathroom on the second floor, and a large living room, dining room, kitchen and half bathroom with an enclosed porch/sunroom on the first floor, this home has beautiful natural woodwork throughout and hardwood floors through most of the home. There is a 10 year old standing seam roof and a 10 year old hot water heater. A pellet stove in the living room gives you an alternative heat source to the oil fueled forced hot air. The home is on town water and sewer adding to the ease of maintenance. The laundry is in the basement where there is also a workshop area and room for storage. There is a wooden deck off the back porch and a nice back yard with a shed. The 1 car garage needs some TLC. This neighborhood location near downtown Springfield, is just 5 minutes from I-91 getting you to your desired location quickly. Just 35 min to WRJ, 45 min to DHMC, 40 min to Brattleboro, 50 min to Keene. Less than 30 min to Okemo for skiing, 15 min to the VT Country Store in Rockingham, 25 min to Windsor's Harpoon Brewery and Simon Pearce Glass. This one is definitely worth a look! Come by the open house on Sunday, August 16 from 1-3pm!
This charming Craftsman-style home is full of original character, solid craftsmanship, and endless potential. With great bones and years of careful maintenance, it's ready for its next owner to restore it to its former glory. While some cosmetic updates and unfinished projects remain, the home's original details shine through, including beautiful woodwork and the signature central staircase. Currently listed with a ¾ bath and a ½ bath, the home is actually plumbed for three bathroom locations, with the beginnings of a full bathroom having been started on the 2nd floor. The flexible floor plan presents a variety of possibilities. A separate entrance provides the opportunity to create a private one-bedroom apartment complete with an eat-in kitchen and ¾ bath making it ideal for rental income, guests, or multi-generational living. Alternatively, the kitchen could be removed to create an additional second-floor bonus room while maintaining the home's single-family layout. The possibilities don't stop there. A full walk-up attic offers the potential for even more finished living space, while the full concrete basement with tall ceilings provides an excellent workshop area, hobby space, or abundant storage. Outside, you'll find a spacious, level yard that is a rare find for an in-town property. With plenty of room for gardening, outdoor entertaining, or simply enjoying the open space, the yard offers endless possibilities. A handy storage shed provides additional space for lawn equipment, gardening tools, or seasonal items. Whether you're looking for a restoration project, an investment opportunity, or a spacious home you can customize to your own style, this property is packed with potential.
More photos are coming! This home has been loved and cared for 50 plus years by the same family and now it is ready for a new chapter. Located in a nice family friendly neighborhood that is perfect for evening strolls around the block. Home features newer windows, hardwood floors, a heated sunroom, and a large dining room. The living room flows nicely into the heated sunroom for lots of entertaining space. The basement has built in storage and is a great spot for hobbies or workshop. The large open yard has garden space, but the sweet spot is the patio over the garage where one could easily enlarge the home. You won't want to miss taking a look at this one.

© 2026 Northern New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NNEREN. Subject to errors, omissions, prior sale, change or withdrawal without notice.