Chester VT Real Estate

MLS Number 5024631

• Residential Single Family
• Full Bath 1
• Address 96 S. Main Street
• Construction Existing
• Bedrooms 4

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 backyard-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!

Listed by Jessica Citera of Cummings & Co

MLS Number 5024539

• Residential Single Family
• Address 663 Depot Street
• Construction Existing
• Bedrooms 3
• Bathroom 2

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 barn-larger than the house itself-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 Snow-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 you're searching for a primary home or an investment, this timeless home is not one to miss.

Listed by Betsy Adamovich of Real Broker LLC

MLS Number 5024148

• Residential Single Family
• Full Bath 1
• Address 102 Church Street
• Construction Existing
• Bedrooms 4

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.

Listed by Geralyn Donohue of Engel & Volkers Okemo

MLS Number 5023780

• Residential Single Family
• Full Bath 3
• Address 196 North Street
• Construction Existing
• Bedrooms 3

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.

Listed by Geralyn Donohue of Engel & Volkers Okemo

MLS Number 5021066

• Multifamily
• Address 17 Grafton Street
• Units 2
• Acreage 0.17
• Square Feet 1,824

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 won't last long. Come take a look today!

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

MLS Number 5017745

• Multifamily
• Address 3630 Vt Route 103 N
• Units 2
• Bathroom 3
• Acreage 2

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, it's conveniently located near the vibrant shops, dining options, and recreational activities of Chester and Ludlow. This versatile property allows for multiple avenues of income-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.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

MLS Number 5017587

• Residential Single Family
• Full Bath 2
• Address 354 Miner Road
• Construction Existing
• Bedrooms 3

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 caretaker's house with a 3-bay garage, and fiber optic internet. Showings begin October 11.

Listed by Dia Jenks and T Story Jenks of LandVest,Inc/Woodstock

MLS Number 5012763

• Multifamily
• Address 1377 Vtrt 103
• Units 3
• Bathroom 3
• Acreage 3

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.

Listed by Michael England of Michael England Real Estate

MLS Number 5005884

• Residential Single Family
• Full Bath 1
• Construction Existing
• Bedrooms 3
• Bathroom 2

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.

Listed by Geralyn Donohue of Engel & Volkers Okemo

MLS Number 5002063

• Residential Single Family
• Full Bath 2
• Address 1328 Chandler Road
• Construction Existing
• Bedrooms 4

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.

Listed by Suzanne Garvey and Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

MLS Number 5000207

• Residential Single Family
• Full Bath 2
• Address 157 Thompson Road
• Construction Existing
• Bedrooms 4

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!

Listed by Glenn Olney and Chelsea Cary of Barrett and Valley Associates Inc.

MLS Number 5000203

• Residential Single Family
• Full Bath 2
• Address 491 Farrar Road
• Construction Existing
• Bedrooms 4

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.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

MLS Number 4996384

• Residential Single Family
• Full Bath 2
• Construction Existing
• Bedrooms 4
• Bathroom 4

Luxurious contemporary home in a naturalized setting. Beautiful mountain views from family room and expansive deck. This home is a unique blend of country charm and modern convenience. Everyone will gather round the large center island in this amazing kitchen designed for cooking and entertaining. Open concept floor plan flows from kitchen to dining area and into the family room where you can set and take in the mountain views beyond. Slider leads to the deck combining indoor and outdoor living space. A private den is connected to the family room with French doors and can be opened up for addition living space or closed off for a quiet retreat. Second floor has three generous sized bedrooms, two of which are en suites. There is also a bonus room on the second floor that can be used for crafts, or additional den, home office or playroom. Wired for generator as well. Currently used as a family getaway and Airbnb. Home is located within minutes from year-round outdoor fun. Chester Recreation Center has a beautiful pool and lots of play area too. There are also local swimming holes, lots of hiking trails with lots to do. Just 18 minutes to the ski lifts at Okemo.

Listed by Julie Buffum of Buffum Realty

MLS Number 4996225

• Multifamily
• Units 3
• Bathroom 3
• Acreage 0.75
• Square Feet 2,008

Opportunity awaits! This three-unit property has been very well maintained with 2 long term tenants and 1 Vacant unit that has just been painted and is ready to be owner occupied or rented out. This investment features an in-town location within walking distance to shopping, restaurants and local conveniences. This property also includes additional unfinished square footage in the barn, currently used as 2 rented storage units with great potential for new ideas. Even the basement is impressive as it has all been gone through. The outside of this home was just painted last year. All units are in good shape and fully applianced. This property also has a large in town open lot.

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

MLS Number 4995602

• Residential Single Family
• Full Bath 1
• Construction Existing
• Bedrooms 2
• Bathroom 2

This charming home in Chester combines Vermont's rural charm with modern amenities. Surrounded by the serene beauty of Fox Chair Mountain, it offers an enchanting escape from daily life's hustle and bustle. Within the home, you'll find cozy spaces perfect for relaxation. From the inviting great room that opens onto a beautiful stone patio to the tranquil library, or the large private deck off the primary suite, and even the attached horse barn, there are several private areas to unwind and rejuvenate in this retreat. With two fireplaces and a wood stove, this home ensures comfort year-round. The modern kitchen is central to the flowing home and the porches and stone patio make gathering with friends and family a breeze whether it be an intimate dinner or a large crowd. The home's southern exposure over a stunning alpine valley provides endless opportunities to appreciate Vermont's natural beauty. With a rich history as a working farm, this property is ready for its next chapter. Additionally, beyond the 3-acre home site being offered is the opportunity to own a further 90+/- acres of stunning land with an outdoor riding arena, and perhaps an opportunity to create additional building lots. Whichever you choose you will find yourself poised for the enriching experience of living in this captivating haven. Don't miss the chance to create your sanctuary in Vermont. Schedule a viewing today and explore the possibilities of this pastoral paradise.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

MLS Number 4994539

• Residential Single Family
• Full Bath 2
• Address 3590 Vt 103 North
• Construction Existing
• Bedrooms 4

Fully furnished! This home on .89 acres is located in the beautiful area of Gassetts in Chester, Vermont. Zoning is versatile and provides a wide range of options for commercial, retail, residential, or industrial use. Whether you're seeking a year-round vacation home or a weekend getaway, this beautiful mountain retreat offers the ideal combination of luxury, location, and outdoor adventure. 10 minutes to Okemo, 20 minutes to Magic Mountain, 30 minutes to Bromley, 40 minutes to Killington and under an hour drive to Stratton ski resort. Recent upgrades to the home include a brand new roof, siding, all new flooring, new kitchen cabinets and quarts countertops, new sheetrock and paint in the majority of the house, new sub flooring in the living room, laundry area, and mudroom, new window sills, new mini split, removal of all previous knob and tube wiring, replaced windows, new french door in the living room, new patio and fire pit area, freshly leveled and graveled driveway, two-car carport, refinished front deck, and freshly leveled backyard. This three bedroom, two bathroom home has an open concept. The three bedrooms are located on the second floor, with one bathroom being on the first floor as well as the second. Hiking, mountain biking, and snowmobiling trails surround the town, making this home ideal for anyone who enjoys the natural beauty of Vermont. High speed internet is available (currently VTEL).

Listed by Jessica Samples of BHG Masiello Keene

MLS Number 4986618

• Residential Single Family
• Full Bath 2
• Address 4877 Vt Route 103
• Construction Existing
• Bedrooms 4

Looking for the perfect ready to move in home in Vermont? Look no further than this French Provincial meets Vermont cabin centrally located in the quiet town of Chester, Vermont on Route 103. Within an hour drive to 5+ great ski mountains, within 10 minutes to Okemo mountain. House features so many great amenities and improvements--new black/grey roof just installed June 2024, new egress windows, beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes and state parks, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today! Added bonus is owner is willing to offer financing with 30% down payment to approved buyer.

Listed by Erin Kendall of EXP Realty