Properties Near 2739 Route 11 Chester, VT

Restore Properties
Welcome to 34 Fox Chair Terrace, a peaceful, private three-bedroom, two-bath home set on a full acre just minutes from downtown Springfield and charming Chester, Vermont. Tucked away in a quiet rural setting, this spacious property offers the best of both worlds: privacy and nature, with easy access to shopping, schools, the local hospital, and other area amenities. Step inside to find a bright and comfortable layout. The partially finished basement adds valuable flexible space perfect for a home office, workout area, or playroom. The detached two-car garage keeps your vehicles and gear protected year-round. Whether looking for your forever home or a peaceful retreat, this property delivers comfort, space, and convenience in a beautiful Vermont setting.
Beautiful New Englander on two picturesque acres between Chester and Springfield, 5 minutes from local shopping and the hospital. The house sits on a quiet, paved and town-maintained road, with breathtaking views and wonderful privacy. Lots of flowers and berry bushes pepper an expansive and lovely lawn. Park your vehicles in a spacious 2-car electrified garage with an overhead storage area, and a new EV Charger! There's also a storage shed for lawn tools. Feel the charm as soon as you enter the enclosed sunroom, with a wall of windows overlooking scenic mountain vistas and wildlife. From here, step up into a cozy dining room, which flows into a quaint den looking out over the deck and onto an expansive and deep backyard. The dining room, den and kitchen ALL have heated floors, so feet stay warm on those winter night trips to the kitchen! A cozy living room sports new carpet (ALL carpeted surfaces have new carpet!). The kitchen boasts plenty of cabinet space and a small butler panty, as well as a brand new induction oven, safe for kids, as the stovetop does not get hot during cooking! Also on the first floor is a full bath, a laundry room, and an office. There are built-ins throughout the house. On the second level are 3 nice-sized bedrooms, a large, wide hallway, and another full bath, as well as a small area that has been used as another office. Recent electrical and exterior upgrades have brought this house to the next level. Bring your dreams to this well-loved home!
Beautifully set in total privacy, this cozy cabin is the perfect retreat! Nestled on a secluded, level lot, this charming home offers a peaceful escape surrounded by nature. Inside, you’ll find wide pine floors, granite countertops, and a freshly painted interior and exterior that give the space an updated feel. The spacious layout includes large rooms and a versatile loft ideal for guests, a small home office, or extra storage. Unwind in the large Jacuzzi jet tub after a long day, or step outside to enjoy the beautifully landscaped grounds. A serene, oversized pond adds to the tranquil setting, while a fenced-in garden area is perfect for growing your own vegetables or flowers. Relax or entertain under the covered stone patio, and enjoy the many thoughtful touches throughout the property that make it truly special. Whether you're looking for a weekend getaway or a full-time home, this private cabin has everything you need and more!
Off a peaceful road in the wonderful town of Springfield, VT sits a beautifully maintained 3-bedroom, 1.5-bath ranch nestled on a peaceful and private 2-acre lot. This easy-living home features freshly sanded hardwood floors throughout, offering a warm and timeless feel in every room. Enjoy the simplicity of single-level living with an efficient layout and low-maintenance design. The full walk-out basement provides excellent storage and future expansion potential, while the spacious shed/barn on the property offers endless possibilities for hobbies, animals, or additional storage. Conveniently located just minutes from Springfield Hospital, I-91, shopping, dining, and local schools, this home offers the perfect balance of rural charm and in-town accessibility. Outdoor enthusiasts will love the close proximity to Okemo Mountain, Mount Ascutney, snowmobiling, and trails/hiking. Whether you're starting out, downsizing, or seeking a peaceful Vermont retreat, this property blends comfort, convenience, and country character in one desirable package.
This bright and inviting Gambrel home sits on a corner lot and offers a lovely, fenced backyard, to grow your garden, or play toss with the kids. This home features a welcoming, large foyer, a generous living room and a formal dining room for those family dinners. The kitchen features an island to enjoy the morning coffee. With four bedrooms 1 full bathroom and one 1.4 baths, there is plenty of room for all. The basement offers space for a workshop, a hobby room and plenty of storage space in addition to a 1 car garage. The beautiful outdoor patio provides for outdoor entertaining and container gardening as well as looking to the tree house, perfect for the kids!! A must see.
Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect one level living on the first floor with all your needs in one space including a huge bath with step in shower and a utility room for washer and dryer. This is a must see for anyone who is looking for single or multi family with affordability.
The view from the road does not give you the fact that behind the house is a beautiful and private backyard! This property has great possibilities for you to create your own vision of what it can become. You could either do some improvements to the existing gambrel structure which has been a comfortable residence for many years, or you could use it as some kind of allowed business or rental and turn the really nice barn into your new house. The barn sits in a really nice spot overlooking the open landscaped property, with a nice private woodsy area behind. Offered for sale for the first time in almost 40 years!
Open House Thursday, September 11, 4:00 - 6:00 Welcome to your Vermont retreat, an inviting one bedroom, one bath home sat on 2.5 acres at the end of a dead end road in Chester. This 528 square-foot cottage has been thoughtfully updated for four season, comfort, featuring full insulation, a woodstove for cozy evenings, and efficient mini-splits providing both heating and air-conditioning. Recent upgrades include a brand new three bedroom septic system, making expansion a future option and a detached two car garage that offers excellent storage for vehicles, ski gear, or workshop space, along with an electric car charging station hookup. The property is dotted with mature sugar maples, already tapped, bringing an authentic Vermont sugaring tradition right to your doorstep. Just minutes from Chester‘s, charming Village center, and Springfield amenities, and a short drive to Okemo Mountain resort, this location is ideal for year-round, living, a ski getaway, or a weekend retreat. Whether you’re seeking a low maintenance primary residence or a charming, second home, this property blends, rustic appeal with modern convenience in quintessential Vermont setting.
Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.
Adorable Village Home in the Heart of Chester, Vermont This charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage. Inside, you’ll love the warm, inviting living space with wood accents, an open-concept kitchen and dining area, and cozy bedrooms filled with natural light. The updated bath has a fresh, modern feel, and the flexible layout offers space for guests, work-from-home, or hobbies. This is more than a house — it’s a home with heart, waiting for its next chapter. Located just minutes from Chester’s historic village green — shops, dining, and year-round recreation are all close by. Whether you’re looking for a starter home, Vermont getaway, or a low-maintenance lifestyle, this adorable home checks all the boxes.
Large home on generously sized lot with lots of room to romp this 3BR/2BA home has lots of space indoors and out. Roomy and sun filled kitchen flows right into the dining room. Living room is cozy with the pellet stove glowing. Good sized mud room could be used as a small office or reading room or a place to do homework. 1st floor full bath and laundry for your convenience. 2nd floor has a seriously large primary bed with full bath, along with 2 other bedrooms and if you need a little more space, there is an attic as well. Along with a 2-car garage this home should meet your needs.
Delightful light filled ranch home with a touch of whimsy and country mixed to make this home a happy spot to be. Walk into the large finished and heated breezeway, a great place to sit a spell or use as a mud room. Access to the breezeway from front, back and the garage to make this a very convenient and usable space. This home features a large kitchen with room for a table, stainless steel appliances, large pantry and a view to the front yard through the living room. Generously sized, this living room is bright and cheery with picture window, and happy colors. Large 3-piece bath with updated tile surround has a stackable washer/dryer and linen closet. Both bedrooms have lots of natural light and good-sized closets for storage. A nice full, dry basement gives plenty of room for storage or additional play or activity space. The back yard is a gardener's delight. Lots of perennial flowers fill the yard along with fruit trees, raised beds, outdoor storage and still lawn to mow. There's a covered porch to sit and watch the birds and bees and maybe with all the whimsy you might glimpse a fairy or two. Who Knows! This colorful cheery home is sure to lift your spirits.
Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer, which is a great space to store the skis, poles and helmets from a great day of skiing. The main level features a generous living room anchored by a classic wood-burning fireplace ideal for cozy winter evenings. The sunny eat-in kitchen provides ample space for meals and gatherings, while the full bath with laundry adds everyday practicality. All windows were replaced in 2019, offering energy efficiency and bright natural light throughout. Upstairs, you'll find three spacious bedrooms, including a stunning turret space that creates a bright and airy nook perfect for reading or relaxing under the sun-drenched windows. The original woodwork and architectural details throughout highlight the craftsmanship of a bygone era. Outside, the covered wrap-around porch invites you to unwind and enjoy the peaceful sounds of the nearby babbling brook. Take a short stroll to the local market or explore the picturesque village with its shops, restaurants, and small-town charm. This home is more than just a place to stay it’s a place to create lasting memories. All only 15 miles from Okemo Mountain!
Come visit this cozy 2-bedroom home on a very quiet street with very little traffic. This house has been owned by the same family since new in 1955! An ideal home for someone who wants easy access to living on one level, but if you need more room, there's a large open area in the basement that would make a great family room. You will love sitting in the peaceful back yard with a large screened in gazebo, plus there is a nice storage shed for garden equipment.
Come and take a look at this very inviting home that has been lovingly maintained by the current owner for 41 years! The yard is gorgeous with lots of flowers, berry bushes, rhubarb, ornamental trees and an apple tree, and there is good privacy to enjoy the quiet backyard. On the main level of the house to the nice roomy country kitchen, a dining room, and living room. Walk down the wide hallway and you will find a full bath and three comfortable bedrooms, one with a 1/4 bath. In the basement there is a one-car garage coming in from the frontage on Southridge Street. This property is unique in that it has frontage on two streets, so that you can drive in from White Street for very easy access into the main living area.
This sweet little bungalow is a true work in progress — and it’s almost ready to welcome its next owner! Whether you’re searching for your very first home, looking to downsize, or dreaming of a Vermont retreat, this property is full of charm and possibility. Thoughtful updates are well underway, including a new roof, electrical, plumbing, heating, insulation, windows, flooring, and sheetrock, so you can simply settle in and start enjoying the space. Tucked away in a lovely setting, it’s the perfect spot to relax and take in all that Vermont has to offer. Interior photos coming soon!
Back on Market and now listed BELOW appraised value! Charming Dutch Colonial just moments from the hospital! This adorable 2-bedroom, 1-bath home is perfect for first-time buyers or those looking to downsize. Located on a quiet side street, you’ll enjoy the peaceful setting with the convenience of nearby amenities. The main level offers a cozy living room and a combined kitchen/dining area, while both bedrooms and the full bath are tucked upstairs. A heated back porch lets you enjoy the outdoors year-round—ideal for morning coffee, a reading nook, or extra flex space. A one-car garage adds convenience and additional storage, and furnishings are negotiable, making your move even easier. Low-maintenance and move-in ready, this home is a must-see!
Tucked back from the paved road and surrounded by woods, this charming 3-bedroom, 1.5-bath home offers both privacy and convenience. With a little updating and personal touch, it has all the makings of a wonderful starter home or the perfect Vermont getaway. Ideally located near several major ski areas and the lakes region, you’ll enjoy year-round recreation — from winter skiing to summer days on the water. A true four-season retreat waiting for its next chapter! Best suited as cash or conventional purchase.
Welcome to easy one-level living at this well-maintained 2-bedroom, 1-bath home on a half-acre lot in a convenient Springfield location. With low-maintenance vinyl siding and a durable metal roof, this home is built for simplicity and comfort. Step inside from the freshly painted back deck, where you'll find a functional layout perfect for first-time buyers or those looking to downsize. The property features raised garden beds, an insulated shed for extra storage or hobbies, and a large garage with overhead storage. An adorable enclosed front porch offers a cozy spot to unwind, read, or enjoy the view. Located just minutes from town and local amenities, this is a smart and affordable option in a great setting.
One of the best home values in Springfield! Sure, this 4-bedroom home could use a little TLC, but it's on a quiet street in Springfield, not far from the hospital and shopping at either downtown or at the plaza, and only a half hour to Okemo for winter and summer activities! The opportunity is tremendous here to make this your lovely home at a great price! Nice sized rooms and there is plenty of room for storage in the attached barn. Pleasant backyard with a charming gazebo for the summer months. There are lots of nice old features with this property, and with a little love this colonial farmhouse can be a classic beauty! Make an appointment to take a look today!
Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building I believe that the highest and best use would be to return it to a single-family home with one accessory apartment in the back. The house is in need of renovation however, the style and location would lend well to that investment, or renovate the four units as your next venture, either way you will have a fine home near the center of all that Chester has to offer!
Cozy and Full of Potential! Tucked away in a quiet neighborhood yet close to all local amenities, this inviting home offers the ease of one-level living. With just a little finishing work, it can become the perfect retreat after a long day. Enjoy a spacious yard, a sunny setting, and the convenience of a one-car under garage. The home has already seen several updates, including a new kitchen, fully insulated walls, and some new windows. The property is being sold as-is and will require a few finishing touches—such as exterior painting and interior trim work. Please note: due to chipping and peeling exterior paint and some interior trim and drywall work needed, the home will not qualify for government financing. Cash, rehab loan, or conventional mortgage depending on the lender, is the best option. This home is a fantastic opportunity to add your personal touch and build equity. Don’t miss out—schedule your showing today!

© 2025 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.