Chester, VT | 3713 Trebo Road

Check out this newly renovated colonial home located on a corner lot on Union Street. Sited on an almost 1.5-acre lot, there is plenty of room for extensive gardens. There is also an existing fenced in area for the family dog equipped with a private dog entrance. The House has had extensive work done to first two floors with new Kitchen and newly renovated bathrooms, featuring a Primary Suite with En Suite bath, featuring a walk-in shower and soaking tub. The other upstairs bathroom holds the Laundry. Off the kitchen there is a large space perfect for a pantry. The house also features a welcoming mudroom. In addition, the home offers mini-split heating units in most every room offering A/C for the summer months. The 3rd floor of the home is not renovated and offers a blank canvas for further space. It is presently divided into two spaces perfect for office space.

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, brand new LVL carrying beam and floor joists, new interior trap door basement access and stairs, and new laundry station 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.

BACK ON THE MARKET BECAUSE OF BUYER ISSUES, IT HAS NOTHING TO DO WITH THE PROPERTY! A COMPLETE NEW SEPTIC WITH A 1250 GALLON TANK AND NEW LEACHFIELD TO BE INSTALLED IN EARLY OCTOBER. 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 coop 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.

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.

Original 1800's cape style home situated conveniently between Springfield and Chester. Home has seen updates over the years but continues to show original charm of an 1800's period home, exposed beams in primary bedroom, mixed wood floors, post and beam shed/garage with usable and accessible second floor. The enclosed front porch leads you to the comfortable, sunlit eat in country kitchen which features a large island for cooking, a picture window onto the back deck and access to the garage. Good sized living room runs front to back taking advantage of views of the quiet back yard and the small neighborhood where the home is located. First floor bedroom with exposed beams has a bonus room attached that might be a great spot for a primary bath. Second floor has the standard layout of a bedroom on either side of the stairs one featuring a witch window, somewhat common in New England. The expansive grounds are landscaped with perennials, fruit trees, open and shaded areas and is bordered by a stream. While the home has seen updates over the years for comfort such as newer windows and updated kitchen, drilled well, it has retained its original charm, and the family is ready to move the home on to its new family for the next chapter of its life. This is an estate home and offer "AS IS"

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!

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.

Now offered at $229,900! If you're looking for a solid home with good bones and the opportunity to make it your own, this 4-bedroom home is worth a look. The house does need work and updating but offers a functional layout with four bedrooms and a half bath upstairs, a spacious full bath on the first floor, and a kitchen with pantry space opening to the dining room. A major bonus is the brand-new detached 2-car garage with electricity, set on a concrete slab. Bring your ideas and build on what's already here! Conveniently located for year-round Vermont living and recreation, approximately 30 minutes to Dartmouth Hospital, as well as Okemo and an hour to both Killington and Mount Snow. There's plenty of potential to make this property your own! The Seller is offering a $5,000 concession towards future repairs with a reasonable offer!!

MOTIVATED SELLERS! PRICE REDUCTION AND OFFERING UP TO 3% TOWARDS BUYER CLOSING COST. Delightful cape style home in a family friendly neighborhood. Large lot with detached single car garage, additional building for storage, lots of level space for a garden or to fence in. Home features a covered entry. This home has seen lots of updates thru its life including a newer roof, new wooden siding that has been freshly painted, interior of the home has also been freshly painted. Lots of natural light, home has a large open living/dining area, two bedrooms down and one large bedroom upstairs. This is a perfect home for buyers just starting, empty nesters and plenty in between. More photos are coming, please stay tuned and add this one to your list of must sees.

CONTINUE TO SHOW PLEASE!! Enjoy the ease of single-level living in this 2008 single-wide home set on 2.5 peaceful Vermont acres. The open concept kitchen and living area is filled with natural light, creating a warm and inviting atmosphere. Offering three bedrooms, one full bath, and a convenient laundry area. Recent improvements include new carpeting and fresh interior paint, making this home truly move in ready. The level 2.5 acre lot provides plenty of space for gardening, outdoor recreation, or simply enjoying the beauty of Vermont’s seasons. Two outbuildings offer great storage for tools, equipment, or outdoor gear. Conveniently located near several Southern Vermont ski destinations including Okemo Mountain Resort, Magic Mountain, Bromley Mountain, and Stratton Mountain Resort as well as Mount Sunapee in New Hampshire making this an excellent year-round home base. Immediate occupancy available.

Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An existing trailer on the property provides a convenient place to live or use as a base while planning and constructing your new home. With a blend of privacy, natural beauty, and existing improvements, this property is ready for you to bring your vision to life while remaining just minutes from shopping, dining, and year-round outdoor recreation. Selling as-is and needing at least 60 days to close. Also listed under MLS #5102143.

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests.

Welcome to the past with this 1928 timepiece, owned by the same family since 1937, when the gentleman owner's parents bought the place when he was two years old! He can tell you a lot of history from the neighborhood through the years. This is a very nice solid house loaded with charm! The beautiful natural and untouched woodwork is amazing! The eat-in kitchen is very cool too, with natural wood cabinets and the (non-working) dishwasher that was installed in 1953! Also on the first floor are the living room and dining room, again with the beautiful woodwork, and upstairs you will find 3 bedrooms and a full bath. There have been recent updates including a new roof and oil tank. Convenient location to shopping and the hospital. Enjoy summer evenings sitting on the spacious porch as the owners and their family have done for the past 79 years.