The median home value in Chester, VT is $608,000.
This is
higher than
the county median home value of $334,800.
The national median home value is $338,100.
The average price of homes sold in Chester, VT is $608,000.
Approximately 55.38% of Chester homes are owned,
compared to 14.63% rented, while
29.98% are vacant.
Chester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Chester real estate agent to arrange a tour today!
Escape to this charming log cabin, tucked away on a quiet dead-end road. With an attached two-car garage and a small horse barn, this property is perfect for those seeking a blend of rustic charm and practicality. Inside, youâ??ll find a thoughtfully designed two-bedroom, one-bathroom layout with an airy open floor plan. The kitchen and living room flow seamlessly together, centered around a wood stove that creates a warm and inviting atmosphere during the winter months. The main living area features classic wide board pine flooring, while the bedrooms boast updated vinyl plank floors for a modern touch. A spacious entryway doubles as a den, providing versatility to suit your lifestyle. The full basement includes a finished bonus room for additional living space and offers potential for further expansion. Step outside to enjoy summer evenings on the covered front porch. This peaceful retreat is just minutes from Chesterâ??s charming village center, where youâ??ll find dining and shopping options. Plus, itâ??s a short drive to Okemo Mountain for year-round recreation. Whether youâ??re looking for a cozy home or a weekend getaway, this property has it all! Donâ??t miss your chance to own this log cabin in an ideal location within close proximity to ski mountains, lakes, shopping, and dining! Visit the Okemo real estate community today. Taxes are based on current town assessment.
This spacious 1800's home is filled with Vermont charm and located in the heart of Chester. Filled with natural light from newly installed windows, the home boasts beautiful wood floors throughout and antique door handles that capture the essence of the era. Spacious bedrooms provide ample comfort, while smart thermostats ensure modern convenience. A newly built, covered front porch welcomes you into the home, and a deck off the kitchen leads to an open, level backyardâ??perfect for gardening or outdoor activities. One of the standout features of this property is the versatile studio space. Accessible via its own entrance from Main Street, this expansive area features vaulted ceilings and two half baths, offering endless possibilities. Whether you're looking to create a storefront, set up an at-home business, or convert the space into a private apartment, the potential is limitless. This property offers a unique opportunity to live in a quintessential Vermont town while having the flexibility to tailor the space to your needs. It's a must-see for anyone seeking a charming, functional home with potential for growth!
Step into the charm of yesteryear with all the comforts of today at 663 Depot Street. This completely renovated 3-bedroom, 2-bathroom home combines historic character with modern convenience. Since 2022, everything from the insulation, drywall, electrical, plumbing, & HVAC has been updated, including a new furnace, water heater, fixtures, countertops, cabinets & appliances. The only original feature left untouched is the flooring- beautifully refinished original wood. The owners thoughtfully chose period-appropriate paint colors & preserved unique touches like exposed beams & original woodwork. You'll love the Victorian martini pedestal sink in the upper bathroom! There is also a 2-story attached post-and-beam barnâ??larger than the house itselfâ??with a powered overhead door. Keep it as a garage or workshop, or explore the incredible potential to double your livable space by finishing it. Sited on 1 acre, the property has a sprawling lawn, fire pit for evenings under the stars & an unbeatable location near Chester's Stone Village, Grist Mill, Smitty's Market, & other local amenities. Just 15 min to Okemo Mtn & the lakes, 30 min to Bromley, & under an hr to Killington, Stratton, & Mt Snowâ??a prime spot for skiing, hiking, & year-round fun. Currently used as both a family getaway & a successful Airbnb, this property has serious income potential for those looking to maximize its use. Whether youâ??re searching for a primary home or an investment, this timeless home is not one to miss.
A classic, easy maintenance four bedroom, two bath home in Chester village on .12 acres +/-, within walking distance to the Village Green for summer concerts, restaurants and shopping. The front porch is a focal point and a great way to meet your neighbors and passersby on the walking loop. The first floor features a large foyer, spacious living room, large dining room with corner built-in and elegant lighting, a country kitchen with marble tile flooring, first floor bath with tiled shower and an adjoining bedroom with a lovely reading/entertainment nook that connects with the dining room. The second floor has a large landing with two adjoining bedrooms, a full bath with radiant heat in the floor and a cool, private back bedroom. The basement has foam insulation and the windows, water heater and oil tank have been replaced. Ready for your enjoyment as primary, secondary or investment property. Close to Magic, Okemo, Bromley and Stratton Resorts, and year year-round recreational activities.
The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer leads to the second floor which features 3 bedrooms, 2 baths and a sitting room. An addition added by the author and named the Queen's Room during the current owners bnb tenure features built-ins, a partition wall with transom window and a wood stove insert flanked by cozy built-in seats. The primary bath features gold-plated fixtures, a skylight and soaking tub. The first floor also has a heated, retail space for a home business with a separate entrance and office above that has served as an antique shop. The two-car attached, garage has unfinished, overhead space. The exterior needs some sprucing up and a new owner will want to add cosmetic upgrades. The property on .70 acres has a lovely yard with a hydrangea bush, charming bridge, small pond and stone bench overlooking the picturesque village.
Unlock the potential of this exceptional mixed-use property, offering a solid income stream and tremendous future upside. Ideally situated in the heart of town, this well-maintained building spans over 6,800 sq. ft. and is currently home to 5 residential units and 6 office units, with potential for retail conversion. Located in the center of town, providing excellent visibility and foot traffic, with easy access to amenities, and major roadways. The property currently generates solid monthly rental income from the residential and office units, with significant potential for increased rents after updates and improvements. The 5 residential units are in good condition but could benefit from updates, offering an opportunity to increase rental rates and enhance value through renovations. The 6 office units offer flexibility for a variety of businesses, with the added benefit of retail potential on the ground floor. Spanning over 6,800 sq. ft., this property offers ample space for both residential and commercial tenants, with room for potential expansion or redevelopment.
Discover this beautifully maintained 1852 Colonial home situated on a prime corner lot in the heart of downtown Chester. Currently configured as a two-unit apartment, this property features a spacious two-bedroom, one-bath unit on the upper level and a cozy one-bedroom, one-bath unit on the first floor. With its versatile layout, you can easily convert it back to a single-family residence or live in one unit while renting out the other to help cover expenses. This home has seen many recent updates, including electrical and plumbing, water heaters, and a newer furnace, ensuring comfort and peace of mind. The roof has also just been replaced, making this property move-in ready. Take advantage of the wonderful opportunity for in-town living, with shops, restaurants, and parks just a stroll away. Showings require at least 48 hours notice as both units are currently occupied. Priced to sell, this Colonial gem wonâ??t last long. Come take a look today!
Private and secluded 46.77 acre wooded lot in Chester, VT. Property is in the current use program. The east side of the property runs along the Chester/Springfield line. 15 minutes to I-91 and within driving distance to Okemo, Stratton, Magic & Bromley Ski Mountains. There is a slight view on the north east side of the property. There is a deeded ROW that is not maintained. This lot is perfect for hunting, recreation and timber agriculture.
91± Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property embodies the best of quintessential Vermont countryside living. A perfect horse property with an outdoor arena and lots of dirt roads for trail riding. The land includes several open meadows, perfect for future development, homesteading, or recreation. Enrolled in Vermontâ??s Current Use Program, the property is both environmentally and financially sustainable. A section of the land was selectively logged, creating a network of trails and plateaus, ideal for hiking, wildlife exploration, or building opportunities. This property offers unparalleled potential for dream homes, private retreats, or as an investment in Vermont real estate. Donâ??t miss the chance to own this unique Vermont land with its stunning mountain views and incredible development possibilities.
Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic. In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors or entrepreneurs. With prominent visibility and high traffic flow, the commercial space is well-suited for a variety of ventures, from retail to office use. Situated just a short drive from Okemo Mountain, this property offers year-round appeal for outdoor enthusiasts and tourists alike. Plus, itâ??s conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow. This versatile property allows for multiple avenues of incomeâ??whether you choose to occupy one of the residential units, rent both out, or utilize the commercial space, the possibilities are endless. Don't miss your chance to own a piece of this thriving community.
Chase Brook Farm is at the end of a quiet country road, offering complete privacy on 53 acres and yet just 10 miles from Okemo Ski Resort, fine dining, and shopping. The views are punctuated by bucolic vistas of the Green Mtns including Steadman Hill, the highest peak in Chester. At the center of this property is a 2,941 s.f. farmhouse, built in 2008 and inspired by countless visits to Sturbridge Village. Thoughtfully designed to evoke the charm of a historic home, it features hand-planed boards, painted wide pine floors, wrought iron latches, and soapstone countertops while providing the comfort of modern amenities, including new mechanicals, updated wiring, and a large, dry basement. This property invites year-round enjoyment. In winter, sled down hills out back, or clear the pond for skating parties. Snowmobilers, skiers, and snowshoers will appreciate the room to roam and easy access to the VAST trail. After a day in the snow, warm up by one of the two cozy fireplaces or take a soak in the hot tub. In summer, enjoy a swim or cast a line in the stocked pond, or gather berries from the 80+ blueberry bushes and raspberry patch. The fall season brings apple picking and the land is suitable for livestock, offering versatility for a variety of uses. Chase Brook weaves in and out along the border to the East. Additional features include an attached 1-bay garage, a 3-bedroom caretakerâ??s house with a 3-bay garage, and fiber optic internet. Showings begin October 11.
This Property features a mostly level lot with a cottage situated above the road in a private, yet easily accessed and convenient location. It is just walking distance from Chester Depot and the Chester Village Green. Currently there is no septic or well, it may appeal as a great camping spot in the beginning. It might just become the perfect location to develop, as a full time place to be!
71 Acres of Prime Wooded Land in Chester, Vermont Discover an exceptional opportunity with this 71-acre wooded parcel, located near the town forest in Chester, Vermont. This unique property features a 6-acre hay field field, offering breathtaking 360-degree views that include the majestic Ascutney Mountain and the stunning Monadnock in New Hampshire. Enrolled in the current use program, you can simply sit back and enjoy the beauty of nature while benefiting from reduced property taxes. Nestled in a Conservation/Residential district, this land is perfect for loggers, or conservationists seeking sustainable harvesting & agriculture options while conserving Vermont's natural beauty. Imagine the possibilities: maintain the integrity of this stunning landscape while earning periodic income from your forest management practices. The diverse ecosystem supports a variety of wildlife, making it an ideal setting for nature enthusiasts and conservationists alike. Whether you're looking to develop a timber investment or preserve a piece of Vermont's wilderness, this property provides a unique blend of potential and beauty. Donâ??t miss your chance to own this slice of paradise!
Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business. There are 2 separate buildings. One needs to be finished, main building 3 floor could be finished for more living space.
Introducing the cultural and commercial centerpiece of one of Vermontâ??s classic small towns: The Fullerton Inn of Chester! In addition to being the anchor go-to Bar & 120-seat Restaurant for locals & tourists (be it indoor or outdoor dining), the venerable, well established Inn boasts 20 guest suites & rooms. Heated outdoor tables on back patio extend the season & Village camaraderie as does the classic front Porch overlooking the Town Green and Gazebo. More Meeting & Event rooms along w/ versatile room/suite configurations open the event venue market for weddings & more amid year-round attractions within ski country, fall foliage, etc... As a nicely profitable going concern, the Fullerton Inn beckons its next owner to seize the reins & fulfill their dreams of operating a country Inn, or adding it to their hospitality portfolio. Professionally managed & maintained, the Inn offers seamless transfer w/ transition assistance, dedicated Executive Chef & staff. Additional features & equipment: large fully equipped 20â?? x 40â?? professional kitchen w/ walk-in coolerâ??kitchen freezerâ??large utility spaceâ??convection oven and fryerâ??2 double coolersâ??ice machineâ??fully sprinklered whole buildingâ??2 owner apartments (1 is 1200â??)â??5YO Peerless furnace w/ backup furnace in full basement w/ separate heating & cooling for barâ??basement chillersâ??bank vaultâ??workshopâ??laundry roomâ??paint roomâ??delivery access. Stroll to the Innâ??s flower gardens, 2 outbuildings & river flowing behind 2.4 flat usable acres.
Come and invest in Main Street America with this exceptional village center location! Are you seeking a state-of-the-art building with excellent revenue opportunities? Look no further. This property has been meticulously updated from top to bottom, offering a prime investment opportunity. The first floor features an expansive open space, formerly an art and presentation gallery, equipped with a portable stage, media room, fully equipped kitchen, LED lighting, skylights, decorative walls, and black walnut flooring. The second floor includes two fully renovated apartments: a one-bedroom and a two-bedroom, both generating approximately $2,800/month . The lower level is climate-controlled with artist stalls, providing additional storage options. Outside, you'll find a handicap ramp for accessibility and and ADA bathrooms; additionally, a large 1850 barn currently used for storage, adds unique character and potential for further utilization. This one-of-a-kind property is a must-see for investors looking to capitalize on a versatile and modern space with substantial income potential.
Unique Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high ceilings and huge amount of work space will be appreciated. Set back from the road with plenty of parking area, there is room to add more outbuildings for business needs. The efficient house features a cozy living room, first floor bedroom, full bath and kitchen/dining that opens to the back deck overlooking the private pond. The second floor has a large common area adjoined by two bedrooms and a half bath with laundry. The whole house generator and Fiber Optic internet service will keep your systems and business running during power outages. Commutable to the Upper Valley, convenient to Springfield, skiing, shopping, Chester Village and all the area has to offer.
Located at the head of the Village Green, it has been home to many successful businesses! The beautiful post and beam interior is warm and inviting. Enjoy the high foot and vehicle traffic in a very desirable area which has long benefitted owners and their businesses. There are 3 units with much potential for more units. The first being the business store front with great road visibility and rustic features like the two sided fireplace chimney, the second is a space in the back which could easily be turned into a long term rental with a kitchen and separate bathroom, the third is a second floor 2bedroom 1 bathroom which has recently been updated and rented with a freshly painted interior as well as new flooring and other updates. Along with the many benefits of this property's location comes parking right on the Green and behind the building with an owned park area. Some recent updates are the back portion on the building has a new roof and $80,000.00 worth of solar was added to the whole building making the electric bill extremely low.
OPPORTUNITY KNOCKS! This full-scale restaurant is a deli and bakery with catering business with 20 years cliental of loyal patronage. This is a turn-key operation that comes fully equipped and has a beer & wine license for the restaurant and an outside under the tent. Sales includes real estate with 1.8 acres with frontage on Rte. 103 which is the second busiest tourist route in Vermont,
Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside a wide-open main living area and great room overlooks the 10 foot deep swimming pond, and the nearby stream can be heard from the deck or kitchen with the windows open. Step into the luxurious primary suite, a sanctuary with large windows and a spa inspired bath with a free-standing tub that boasts one of the best views from the house. Enjoy the newly renovated lower level with additional bedrooms and expansive family room. This area is ready for your touch and enjoys walkout access to the yard and pond. The 2nd level of the barn is currently a wood shop with wood-stove and a 2nd access from the road allows for storing large pieces or equipment on this upper level. The ground level of the barn has traditional sliding barn doors and extensive parking in front. Underground power and water lines travel from the house to a nearby site where another barn or horse arena could be built. A unique home treasure and like its organic architectural design the land has its own special quality of character and beauty. 191 acres are in the VT Land Use program. There is a 6 bedroom septic.
Just minutes from the Chester Green. The largest available lot in the subdivision with end of the road privacy. This almost 10 acre parcel will afford long distance mountain views with clearing. Underground power is at the lot and the permitted septic is an inground system. All of the heavy lifting is done. Bring your plans and your builder or have the seller build your dream home! PLEASE NOTE THERE IS A MINIMUM OF 1,800 Sq Ft Of Finished Living Space.
A very rare find! Here is your chance to own 2+/- acres of beautiful "action ready" land in the town of Chester. Situated in a woodsy setting, your new home will feel intimate and private, yet only a 15 minute walk into the town of Chester. Best of all, the under ground electric, well, septic, cable and gravel pad are existing and ready to be built on!  There is a flat upper pad for your home site with a flat lower grass backyard or walkout basement. In addition, enjoy the sound of the babbling brook that is set safely below the home site. This is truly a one of a kind opportunity for your dream home with all your utilities and pad ready to go! A huge money and time saver! This land is ideally located for skiing! Just 18 minutes to Okemo, 30 minutes to Bromley and 45 minutes to Stratton. Grafton is 10 minutes by car, I-91 is just 15 minutes, and Lebanon/Hanover NH is 1 hour.  The road has been newly renamed so there is no sign post yet. Use the Directions provided here on MLS.
Nestled on a serene, quiet town maintained dirt road, this spacious home offers the perfect blend of tranquility and comfort. As you approach, you'll be captivated by the stunning long-range views that greet you from the expansive deck, a haven for relaxation and outdoor enjoyment. The deck overlooks a picturesque pond, not on the property but offering a beautiful, calming view that enhances the natural charm of the setting all the same. Step inside to discover a thoughtfully designed interior where ample space meets cozy. The large, finished basement is a true bonus, featuring a cozy and convientent propane stove and serving as an ideal games room or entertainment space for family and friends. Featureing 4 large bedrooms, 3.5 bathrooms, with large primary ensuite, large living room with views and that all enticing party or craft space in the below. This is equally a perfect vacation retreat or spacious family home. Conveniently located close to the popular ski areas of Okemo, Stratton, and Magic this home is perfect for winter sports enthusiasts. Whether you're seeking a peaceful year-round residence or a seasonal getaway, this property promises a lifestyle of serene beauty and endless recreational opportunities. Welcome home to your personal oasis.
Welcome to this beautiful historic farm dating back to 1825. At one time known as the Thompson Farm, in 1995 it was purchased by the current owner who lovingly restored it to its former glory. In 1999 it became the "Jersey Girls Farm". Attention was given to retain all of the antique charm, including keeping the original slate roof on main house, all original doors and original wide board floors. The house was also modernized with conveniences such as a new heating system, new wiring, new windows (retaining the original design), and a full array of solar panels to make the house fully self-sufficient. You will find plenty of room and charm inside, beginning with the large country kitchen which includes a working antique Glenwood stove. There's a huge pantry which doubles as a laundry room. The dining room, living room, library, one bedroom, and spacious 1/2 bath complete the downstairs living area. On the second level are 3 large bedrooms and a full bath in the main structure. The expansive master suite even has a spa tub! This room has a 2nd stairway which leads you back to the kitchen. On almost 33 acres of open and wooded land, all of which sits at the end of a town-maintained road. There's a large pond for swimming, fishing, or even kayaking. 5 outbuildings including a nice 1800's 30 x 80 barn! Endless possibilities: small dairy or horse farm, Airbnb, or bed and breakfast. Just 5 minutes to Chester. Shopping, hospital, skiing at Okemo, I-91 - all within 15 - 20 minutes!
If you are looking to build a new vacation or primary home in Chester, this wooded 10.4+/- acre parcel within short driving distance to Okemo and town awaits your plans. The surveyed parcel offers 244 feet of road frontage and gently rolling land with a mix of hardwoods and pine. If you are interested in privacy, there is potential for a secluded home site set back from the road. Possible view with some cutting at 1,000 ft plateau. Utility pole is at the road and the location is just 10 minutes from town and centrally located to conveniences. Explore this acreage for your cabin in the woods, primary home setting or recreational fun. Town maintained road.
