The median home value in Chester, VT is $295,000.
This is
lower 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 $295,000.
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!
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.
Welcome to this beautifully maintained 3-bedroom, 2-bathroom ranch-style home nestled in the serene town of Chester, Vermont. This property combines comfort, convenience, and a unique connection to the great outdoors, making it a great retreat or year-round residence. Step inside to discover a bright and inviting living space with a large, combined living room, dining area, and kitchen. The home's layout offers both functionality and warmth, with ample natural light and high ceilings. The three bedrooms provide plenty of room for family, guests, or a home office, while the two full bathrooms offer modern comfort and convenience as well as one of those being attached to the primary bedroom. This home has been lovingly cared for and is in excellent condition, ready for you to move in and make it your own. Outdoor enthusiasts will adore the location! You'll find yourself just steps away from the renowned Vast snowmobile trails, offering endless adventures in every season. Additionally, a short stroll up the class IV portion of Wyman falls road takes you to the wonderful Wyman Falls, where you can enjoy the calming sounds of cascading water and the beauty of nature. Located in charming Chester, this home offers the perfect blend of small-town charm and easy access to Vermontâ??s outdoor treasures. This is your opportunity to own a slice of Vermont paradise.
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 2-bedroom, 1-bath unit on the upper level and a cozy 1-bedroom, 1-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 longâ??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!
Are you looking for a bright & sunny office space? Enjoy this 2nd floor office space available. Convenient location on Main Street adjacent to an active law office. Space renting at $375 per month. Unit include heat, lights, rubbish removal and plowing with plenty of off street parking. Shared powder room. Tenant pays only phone/internet. Easy access, appointment necessary with agent.
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.
Discover this extraordinary property, available for the first time! Nestled on 26 pristine, private acres at the end of a serene road, this 3-bedroom contemporary home is a true gem. Impeccably maintained by its original owners, every detail of this residence has been thoughtfully designed. The home features a welcoming entryway mudroom, a cozy sitting area leading into the dining space, and a spacious kitchen with a granite island, ample cabinets, and extensive counter space. The inviting living room boasts a wood-burning stove, while the main floor includes two large bedrooms, including an ensuite primary. The oversized loft provides the third bedroom and additional office space. Enjoy the expansive, covered wrap-around deck that seamlessly extends your living area outdoors. The property itself is a visual masterpiece with open spaces, exquisite stonework, and several matching outbuildings: an animal barn, an octagon chicken coop, a 2-car garage, and a large storage barn that could easily be transformed into a workshop. Conveniently located just a few miles from town, major ski resorts, and Rt 91, this property offers everything Vermont has to offer. This is truly one of Chesterâ??s finest properties â?? don't miss this rare opportunity!
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 and currently rented as a wonderful Tea Shop. 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 Saltbox 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.
This four lot subdivision is a builders dream. The abutting house took two of the lots for a buffer. Two remaining subdivided lots come complete with state permits for waste water and septic designs. Come take a look and bring your plans. These lots average less than $35k per lot.
This quintessential 4 bedroom (with a septic permit for up to 5 bedrooms)/2.5 bathroom farmhouse, fully renovated and absolutely gorgeous, is perched on a grassy knoll overlooking 32 acres of rolling meadow, hardwood forest and private pond. The modern touches that are essential for today's style of living pair perfectly with the warmth and charm of an old farmhouse. The house was renovated in 2017, including new roof, insulation, pine flooring as well as all plumbing, electrical and heating systems. The open kitchen/living area features a beautiful fieldstone fireplace and there's a main level family room with a side office. Upstairs are the 4 current bedrooms and 2 full bathrooms, including the principal bedroom with its en-suite bath. The large mudroom can handle all your clothes and gear. Sun or Shade? You have choices of two elevated stone patios to enjoy outdoor living in total privacy. The large majestic barn offers plenty of options for events or storage, so bring your dancing boots and have an old fashioned barn dance! The fields, pond and apple trees attract all sorts of wildlife and there couldn't be a more perfect hill for wintertime sledding, snow-shoeing or skating! The expansive fields are currently mowed by a local farmer in exchange for the hay, and Gunderson Road is maintained and plowed by the town. Visit the Okemo real estate community today. Taxes are based on current town assessment.
Discover a unique turnkey opportunity with this beautifully updated 1800's farmhouse, perfect for an inn, B&B, short-term rental or wedding venue. Recently renovated, the stunning home combines modern comforts with timeless charm, making it an ideal choice for both private and commercial ventures. As you enter, a grand staircase warmly welcomes you, leading to spacious interiors with original wide board floors. The property has been meticulously insulated and painted, giving it a fresh, contemporary feel. The serene landscape offers a perfect setting for a retreat, ski trip, or wedding. This property is offering 9 large bedrooms, most with ensuite bathrooms. The commercial kitchen, dining room, and separate ownerâ??s quarters enhance its functionality. Additionally, the Speak Easy, cozy library, and inviting sitting room offer numerous possibilities for creating a welcoming environment. Outside, the large 2000 sqft barn is ideal for a workshop, studio or event space. The property also features a large parking area, a tranquil pond, and open areas for tents to host weddings, all set on over 10 beautiful acres. The pond is surrounded by tranquil areas to sit and relax and nature watch. Whether you're looking to create a large family home, a thriving B&B, a ski club, or an artist retreat, this versatile property is just 10 minutes from Okemo Mountain and less than 10 minutes from the stunning Victorian village of Chester. Motivated Seller is offering Owner Financing.
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.
In Southern Vermont's Green Mountains, Owl Hill Reserve is a sanctuary spanning 1,928 acres, an expanse over twice the size of New York Cityâ??s Central Park. Assembled over half a century, this land has united generations in the celebration of the great outdoors. At the heart of the reserve stands an 1800s brick farmhouse, a testament to earlier days of farming, complemented by two historic barns, a two-bedroom barn apartment and guest house. Surrounding the farmstead are apple trees, stonewalls and a spring fed two-acre swimming pond, creating a quiet retreat or jubilant family gatherings. A 3.5-mile private, gravel road meanders with the brook, unwinding through a carefully managed northern hardwood forest, predominantly Sugar Maple, home to a rich ecosystem including bear, moose, coyote, bobcat, and deer. The changing landscape includes exceptional mountain views and rolling meadows either cut for hay or used for grazing cattle. The clear waters of the brook beckon fly fisherman to cast lines. Cross country skiing, snowshoeing, biking, hiking and equestrian pursuits are all out the backdoor with endless trails to explore. A remote cabin near an apple orchard offers a place to immerse in nature or a place to write. Owl Hill Reserve is a legacy offering. It offers the luxury of simplicity, the wealth of nature, and the bond of family heritage. Less than 3 miles from the village center and skiing nearby: 25 mins to Okemo, 33 mins to Bromley. 2.5 hrs to Boston, 4.5 hrs to NY.
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.
