Chester, VT | 3781 Flamstead Road

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.

Welcome to 3 Lark Lane in Springfield, VT! This expanded 5-bedroom home offers flexible living space and many updates throughout. A spacious addition created a large bonus room along with an expansive kitchen and dining area perfect for everyday living and entertaining. The updated kitchen with granite countertops offers plenty of cabinet and counter space with an open flow into the dining area. The home features a private primary suite complete with a walk-in tiled shower, plus three additional bedrooms for family, guests, or home office needs as well as an additional full bathroom. Recent improvements include a newer roof and new furnace for added peace of mind. Conveniently located with a nice front yard-Great value for a one-level spacious home!

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.

Antique charm at its best! This vintage beauty dates back to the horse and buggy days, but you'd hardly know it once you step inside. Beautifully done hardware floors, newer windows, custom built hardwood cabinets in the kitchen with loads of storage, modern appliances, and lots of natural light gives you that warm and relaxing feeling. Large first floor living room, dining room and bedroom add to the convenience. The second floor has two more generously sized bedrooms. Additionally, there is an incredible amount of storage in the barn. All this, within walking distance to shopping, restaurants, town hall, and all of the basics you might need in the quintessential town of Chester, Vermont! This house is anxiously awaiting it's next lucky owner.

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!

OPEN HOUSE SATURDAY SEPT. 12, 10:00am to NOON. 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 requirements. 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.

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 Okemo and an hour to both Killington and Mount Snow. There's plenty of potential to make this property your own!

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.

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.

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.

Price Reduced after just 3 weeks on market! Priced to sell. Set on approximately 2.5 acres, the property includes a roughly 11,500 sq. ft. former school building with road access, municipal water and sewer, and Medium Density Residential zoning. This property offers significant potential for multifamily housing, residential development, or a mixed-use concept. Potential redevelopment paths include converting the building into 8 rental apartments, daycare or educational space, community space, or a mixed-use project. The larger site may also support additional development concepts, including approximately 12 small homes, subject to permitting. Springfield continues to benefit from 10G fiber availability, access to I-91, Springfield Hospital, and proximity to Okemo, and Woodstock. With existing residential zoning this property is well-suited for developers or investors. Floor plan and inspection available upon request.

This sweet Cape is the perfect place to start your homeownership journey or to simplify your lifestyle with comfortable, easy living. The main level features an inviting open-concept kitchen, dining, and living area, creating a bright and functional space for everyday living and entertaining. Upstairs, you'll find two cozy bedrooms that offer privacy away from the general living area. The full basement provides plenty of room for storage and has the potential to be finished for additional living space. Step outside to the spacious deck overlooking the fenced backyard, complete with a fire pit. It's an ideal setting for relaxing evenings, gatherings with friends, or outdoor play. A detached two-car garage provides plenty of room for vehicles, while the attached rear shed makes room for storing gardening tools, lawn equipment, or seasonal items. This well-maintained home combines comfort, functionality, and affordability. Come see if it's the one for you!

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.

Charming 1800s farmhouse on 1.5 open, level acres with plenty potential! This 2-bedroom, 1-bath home is a great opportunity for first-time homebuyers, those looking to downsize, or investors. Recent updates include a roof replacement with new sheathing, water barrier, 30-year shingles on the front, and metal roofing on the back. The bathroom was updated in February 2026 with a new shower and vanity. Additional improvements include new Andersen windows throughout (2019-2022), new living room sheetrock, and exterior updates with new vapor barrier and T1-11 siding (2019-2021). Enjoy the spacious flat yard and large attic with storage and potential for future living space. Bring your ideas and make this charming farmhouse your own!

Warm wood finishes, thoughtful updates, and a peaceful country setting come together in this inviting home that offers comfort, character, and practicality. Completely renovated in 2024/2025, this one-bedroom, one-bath home is set on 1.37± private acres just minutes from downtown Springfield. From the moment you arrive, the spacious covered carport provides sheltered parking, additional storage, and a welcoming entrance to the home, while the screened-in porch offers the perfect spot to enjoy your morning coffee, unwind after a long day, or simply take in the peaceful surroundings without the bugs. Inside, you'll find an open-concept living area with beautiful tongue-and-groove wood ceilings, durable flooring, and a cozy Jøtul wood stove that creates the perfect gathering space on chilly Vermont evenings. The efficient kitchen features custom butcher block countertops, ample cabinetry, and a comfortable dining area, while the mini-split offers efficient heating and cooling throughout the year. The home also includes an updated bathroom with a walk-in shower, stacked laundry, and quality finishes that maximize both style and functionality. An enclosed mudroom provides the perfect place to store coats, boots, and outdoor gear, while custom wood accents, built-in shelving, and handcrafted details throughout add warmth and personality that are difficult to replicate. Served by a private well and a state-approved three-bedroom septic system, the property also offers flexibility for future expansion. Whether you're looking for a full-time residence, a weekend getaway, or an investment opportunity, this property is move-in ready with a relaxed, low-maintenance lifestyle and room to grow.

Price improvement on this beautiful home! This is a tremendous value for a move in ready home! You will be amazed when you see the condition of this older 1986 mobile home. The owners have maintained it meticulously since they moved it to this location in 2006. Walking distance to the high school and downtown, and near the Springfield hospital as well. There is a large bedroom on each end of the structure, each with a full bath. FHA ready with a tie down certificate. This would be a perfect property for anyone needing one level living with no stairs to enter, since there is a nice long ramp on the front. In the back there is a nice fenced in area for small children or a dog. A nice 2-car garage will give the homeowner space for vehicles plus storage space since there is a second level. Take a look today!

Price improvement on this beautiful home! This is a tremendous value for such a nice move in ready home! You will be amazed when you see the condition! The owners have maintained it meticulously since they moved it to this location in 2006. Ready for bank financing with tie downs recently added with certificate. Walking distance to the high school and downtown, and near the Springfield hospital as well. There is a large bedroom on each end of the structure, each with a full bath. This would be a perfect property for anyone needing one level living with no stairs to enter, since there is a nice long ramp on the front. In the back there is a nice fenced in area for small children or a dog. A 2-car garage will give the homeowner space for two vehicles plus storage space since there is a second level. Take a look today - you won't be disappointed!