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!
Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for buyers looking to create their dream space. Whether you're a car enthusiast, need extra room for tools, toys, and equipment, or just want the flexibility of additional secure space, these garages add both value and versatility to the home. If you're an investor or a homeowner with vision, this is your chance to transform a fixer-upper into something truly special. This property is an ideal location to Okemo Mountain Resort (under 10 miles) as well as Magic Mountain (11 miles), Bromley Mountain (20 miles) and Stratton Mountain Resort (24 miles) where you can enjoy skiing and all of Vermonts seasonal activities alternating year round. Schedule your private showing today!
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!
This Charming, well appointed home has much to offer! This turn key home is tucked away in a great location and neighborhood in walking distance to shops, food options and schools. The home itself has been updated and features many positives like almost all double pane windows, a recently redone paved driveway, an updated mudroom area, a metal standing seam roof, and much more. With a good size back yard and deck it is a perfect place to have family and friends over and enjoy!
This lovingly maintained manufactured home is just waiting for its new owner to enjoy! Located less than 10 mins from North Springfield and just 20 mins to Ludlow on a quiet dirt road. Enter through the large multi-purpose room with views of the pond and perennial gardens. Laundry is conveniently located in the hallway off the kitchen. A wood stove in the living room adds charm and warmth. Enjoy a meal at either the dining room table or bar seating that overlooks the kitchen. Ample counter space and cabinets make cooking a breeze. Portable generator hookup ensures uninterrupted enjoyment no matter the weather. The generator is even included! Windows and furnace were all replaced in 2018/19. Three included outbuildings have room for car, toy or tool storage! Watch wildlife across the rolling lawn or install a fence in the field for your own animals to enjoy. Live the Vermont life in an idyllic location!
Simplify your life and reconnect with nature in this peaceful Chester home. Set on over 5 private acres, this 3-bedroom ranch offers easy, one-level living surrounded by Vermont’s natural beauty. Whether you're seeking a low-maintenance primary residence, a country getaway, or a downsizing opportunity, this home delivers comfort without complication. From the wheelchair-accessible ramp to the hardwood floors and one-level layout, this home blends style with everyday ease and comfort. The layout is practical and inviting, with an open living and dining area that flows easily into the kitchen. Large windows bring in natural light and woodland views, creating a calm and cozy atmosphere. Step outside to enjoy a generous yard with plenty of space for gardening, bonfires, or just breathing in the quiet. With simple systems and room to grow, this property offers the kind of freedom that only Vermont living can provide—space to stretch out, slow down, and savor the seasons. Just a short drive to Chester village shops, farmers markets, and hiking trails, and 16 minutes to skiing at Okemo and World Class Golf at Fox Run and all Ludlow has to offer.
Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep. Inside, the home is open and inviting, with plenty of room to relax or entertain. The large finished basement provides valuable living space, ideal for a game room, media area, or accommodating guests. Recent improvements include a brand-new roof and a high-efficiency propane furnace, both installed just last year, offering modern comfort and peace of mind. Ideally located close to Okemo, plus Stratton, and Magic Mountain are just a short hop away; this property offers the perfect balance of privacy and accessibility. With Vast trails, dirt roads to roam on this is a heavenly location. Whether you're seeking a full-time residence or a weekend escape, this home welcomes you to experience the best of Vermont living.
Nestled in one of Vermont’s historic locations, Chester’s Stone Village offers timeless charm and rich character. This classic Federal-style home—featuring brick ends and a clapboard front—could be your next residence or vacation retreat. While this brick sided inviting 4-bedroom, 2-bath home isn’t built of stone, it belongs to a rare collection of nine homes and a church constructed in the 1830s and 1840s by local masons using stone from nearby Mount Flamstead. The home maintains many of its original features while offering thoughtful updates including new roofing, upgraded electrical systems, and improved plumbing. The updated kitchen provides ample counter space and includes a charming breakfast nook or office area. You'll also find a formal dining room, a living room, and two additional spacious rooms. Upstairs, a beautifully crafted staircase leads to three bedrooms, a full bath, and a half bath. Highlights include wide board flooring, built-ins, and custom woodwork. Step outside to enjoy established gardens, blooming perennials, a hidden stone garden, a patio, and a fire pit—perfect for relaxing or entertaining. Located 12 miles from Okemo Resort, you’ll have easy access to year-round activities including skiing, golfing, hiking, and snowmobiling. This unique Stone Village home is a 5 minute walk to a great local store known as Smitty's. Don’t miss it—come explore Chester and the Okemo Valley community today. Taxes are based on town assessment.
Tucked along the scenic curves of Route 103 & surrounded by the rolling beauty of Chester, Vermont, this unique French Provincial–meets–Vermont cabin is more than just a house—it’s an invitation to breathe deeper, slow down, & reconnect with the rhythm of nature. Wake each morning to the soothing sound of a nearby creek & the scent of fresh mountain air drifting through the trees. Step outside with your coffee & feel the day begin gently, with birdsong & the promise of adventure all around you. Inside, the home blends rustic charm with modern comfort. A spacious living room welcomes you with its wood-burning fireplace—the perfect gathering place after a day on the slopes or exploring the nearby trails. The main floor also features a private master bedroom & a three-piece bath, creating a quiet corner for rest & retreat. Upstairs, three cozy bedrooms offer peaceful views of the surrounding woods, while two inviting lofts provide just the right nooks for curling up with a book or watching your favorite films. A separate recreation room gives everyone space to spread out & make their own memories. Outside, life continues in every season: soak under the stars in the outdoor hot tub, grill with friends on warm summer evenings, or toast marshmallows at the dual fire pit. Recent upgrades- a brand-new roof (June 2024), A/C, a 20kW standby propane generator, & new egress windows, you can settle in with comfort & confidence. This home is ready to be the backdrop for your next chapter!
Experience the warmth of history with the ease of modern living at 663 Depot Street. This fully renovated 3-bedroom, 2-bath home offers historic charm with today’s updates. Since 2022, insulation, drywall, electrical, plumbing, HVAC, furnace, water heater, fixtures, countertops, cabinets, and appliances have all been replaced. The home's original wood flooring has been carefully refinished to honor its roots. Period-appropriate paint colors and thoughtful details like exposed beams and original woodwork add to the timeless feel. The attached 2-story post-and-beam barn—larger than the house—offers incredible potential to expand your living space or create a dream workshop. Set on 1 acre with a sprawling lawn, fire pit, and a prime location near Chester’s Stone Village, Grist Mill, Smitty’s Market, and more. Just 15 min to Okemo and the lakes, 30 min to Bromley, and under an hour to Killington, Stratton, and Mount Snow, it’s ideal for year-round fun. Currently enjoyed as both a family getaway and a successful Airbnb, it offers strong income potential. Whether you’re looking for a primary home or investment, this timeless property is not to be missed.
The Laurin Whiting House, circa 1850, is a Greek Revival style home with 5 bedrooms and 7 baths on 1 +/- acre. The curved, multi-bay veranda wraps around the front of the house with neo-classical columns and an oculus that punctuates the front gable end. A light-filled living room has French doors that open to the lovely porch and adjoin a large bedroom and full bath. The formal dining room connects with the eat-in kitchen with side entrance. An elegant foyer staircase leads to the large landing area on the second floor and a large, ensuite primary bedroom. A third bedroom adjoins a full bath and connects to a back stairway and two additional bedrooms and a bath. The convenient mudroom with adjoining half bath and laundry room connects the house to the barn/event space. The original barn is redesigned to function as a conference center. The meeting space has a separate bar area, two half baths, a tv/game room with exposed beams and a second floor billiard room. The potential uses for this multi-faceted property are many- a spacious full-time home with a business, a duplex, vacation home, ski club or an investment property with rental potential. A large, level yard offers space for gardening, badminton or croquet and a back deck for enjoying summer evenings. Walk to the Town Green for Summer Concerts, shopping and festivals and to the Town Rec area around the corner for year-round exercise and fun!
The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some love, and this property is looking for that person who can bring it back to its former glory days. As they say, the buildings have good bones, so consider this a blank canvas to do whatever you please for renovations. Since it's very original, you can update without having to tear out former "improvements" that might have taken away the antique charm. Since it was a working farm at one time, it still has the old silo. Years ago, this was made into a 4-level living unit. You can bring this back to life and use it as a very unique vacation rental or keep it as a very cool place for your kids and grandkids - much cooler than a treehouse! The attached barn is huge and for years it was used as a barn antique store. You could do that again, or you could use it for animals. With the open land which supplies a big supply of hay each year, this property would be great for horses, cows, and other large animals. There is also a sugar house, plus a separate building out front that was also used for the antique business. Several apple trees, a huge rhubarb patch, and more! Don't wait on this one!
Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal dining room for holiday dinners, 2 connecting living spaces with fireplace, a bedroom and a full bath. Upstairs are 3 more bedrooms and a full and half bath. The character and antique doors and trim make this house a home. The carriage house unit has 3 bedrooms, a kitchen and full bath and a large open great room and is perfect for guests. There are also more areas with potential - two more levels of barn space plus the attic. Outside you will find a large covered porch, a level back yard for games, and the Williams River down at the back of the property. Sold turnkey. Be the 4th family to own this home since 1868 and see why Chester has been voted one of the top 10 most beautiful towns in Vermont! Discover the tasty food options, pubs, antique shops, art galleries, yoga & pottery studios, and a country market with great sandwiches, fresh meats and produce. Experience Vermont - hiking trails, world class skiing, farms, refreshing rivers, restaurants, breweries and more. Be close to the best of Vermont's ski resorts! (Okemo, Killington, Stratton, Bromley, and Magic Mountains).
Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside, you’ll find an open-concept kitchen, dining, and living area that flows effortlessly onto a large deck—ideal for hosting gatherings or enjoying the quiet outdoors. Two oversized primary suites with private ensuites provide luxurious comfort for guests or multigenerational living. A standout feature is the expansive bonus room, currently outfitted as a professional recording studio with soundproofing—ideal for musicians, podcasters, or anyone in need of a creative or quiet workspace. Step outside to a private, tree-lined backyard with multiple decks perfect for relaxing or entertaining. A two-car garage adds convenience, while the whole-house Tesla battery ensures seamless comfort and peace of mind year-round. Whether you're entertaining a crowd or enjoying a peaceful evening at home, this one-of-a-kind Chester retreat offers space, versatility, and thoughtful features throughout. A wonderful value as a primary home or as a vacation home 2 families could share and still have privacy.
Magnificent Queen Ann Style Victorian with 3 bedrooms, 2.5 baths on .37 acres in Chester Village. The remarkable front porch has a beautiful archway and intricate, colorful ornamentation. A tiled entryway/coatroom leads to the elegant foyer with dramatic stairway and beautiful glass Art Nouveau Newel post light. The living room features a marble fireplace, pocket doors and original stained glass picture window. A formal dining room is ready for entertaining as is the well-appointed timeless kitchen with breakfast bar and a large picture window. The elegant great room is a wonderful living space and features skylights, radiant flooring and a dramatic Venetian window overlooking a lovely view in all seasons. Full length glass sliders lead to a side deck with automatic awning for evening sunset meals. An oversized swim spa/hot tub overlooks the meadow beyond and is a great place to unwind! The second floor has 3 bedrooms, a large bath with a clawfoot soaking tub, walk-in shower and a laundry room with half bath. A finished third floor provides office space, storage or room for overflow guests. The house has been thoughtfully outfitted with a dual heating system. In 2000 a barn/garage was constructed with a second floor for hobbies or additional office space. The lovely fenced in yard has garden space and perennial gardens and a lovely maple tree with a perfectly shaped crown. Walk to the Chester Commons, town recreation area and enjoy all that Chester has to offer!
This is not your typical Vermont farmhouse—it’s far better. Surrounded by rolling fields and pastoral views, this beautifully updated home combines classic country charm with modern ease. Inside, you’ll find a warm, sunlit layout anchored by a stunning chef’s kitchen featuring high-end Viking appliances, granite counters, and custom cabinetry. The spacious primary suite is a luxurious retreat, offering peace, comfort, and incredible storage. A flexible floor plan adds to the home's appeal, with a first-floor bonus room—currently a playroom—offering potential as a guest suite or private bedroom, complete with its own covered deck overlooking the fields. Outside, the property is built for both lifestyle and purpose. A 4-stall horse barn with run-in, large cattle barn, oversized workshop, and detached 2-car garage make it ready for your dreams—be it hobby farming, equestrian living, or simply room to roam. A charming one-room cabin tucked in the treeline is perfect for guests, creative space, or glamping. All located in the heart of Vermont ski country—just minutes from Okemo, with easy access to Stratton, Bromley, and Magic. Whether you're looking for a forever home, a modern homestead, or a lifestyle upgrade, this one-of-a-kind property offers beauty, function, and endless inspiration.
Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a wood burning fireplace in the living room, and walls of windows that frame the landscape. The family chef will happily welcome opportunities to prepare meals in this delightful and beautiful kitchen with quartz countertops, Wolf Range, Sub Zero refrigerator and Bosch dishwasher. The upper level includes three bedrooms, with a serene primary suite featuring an ensuite bath. The lower-level family room with wood stove provides a cozy gathering space, perfect for guests or quiet evenings. Outside, enjoy thoughtfully designed perennial gardens, a covered wrap around porch, and a multi-tiered deck with separate dining and lounge areas—ideal for entertaining or simply soaking in the Vermont beauty this home delivers. An oversized detached- garage and large garden shed offer ample storage and functionality. This is a rare opportunity to own a home where form and function live in harmony—designed for those who appreciate timeless architecture, nature, and Vermont living at its finest.
With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous green lawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel Solar Array, extensive drainage & excavation work for a drier basement. Radiant floor heat in 3 bathrooms, kitchen & great room. An open, sunny, 750sf apartment w/separate entrance, new kitchen, windows, cork floor, laundry hook-ups, is ready for family, guests, renters. BA w/clawfoot tub has been added between first floor BR & serene spare room which could be easily expanded to create a larger bath, dressing room, nursery, office. Attached 2 car garage has a new metal roof, drywall ceiling, EV charger. The home has delicious well water, beautiful views from every window, and because of the thick stone wall construction, stays cool in the summer, warm in the winter, incredibly quiet and draft-free. A newer, solidly built 8-stall horse barn w/wonderful hay loft, sits surrounded by fields atop a nearby knoll dotted with daffodils in springtime. An alpaca barn and chicken coop need TLC. Also includes: Fiber optic internet, professional landscaping including many new trees & native perennials, new boiler, buried propane tank, new electric service & some new plumbing. *Can be sold furnished*
Welcome to paradise! Enjoy all four seasons in this handsome colonial-style home with modern amenities. From the covered porch, relax and take in views of the front gardens and your land across the road with apple trees and brook frontage. A large solar array is tucked out of sight producing all the power you would need. Behind the house is a fenced-in garden and greenhouse, a couple of useful sheds and a large, fenced pasture bordered by a brook. Off to the side are two livestock barns and a new 24’ x 48’ equipment shed. If you have use for a large studio space, you are in luck. Above the 2-car garage is a suite outfitted with a kitchen, ¾ bath, and a large open room with fiber internet, perfect for working, writing, creating art, or exercising. Saving the best for last, the home is just lovely. The dream country kitchen with high end appliances and custom tile is open to the sitting room with fireplace. The dining room enjoys the wall of windows overlooking the back acreage. There is a den with closets and ¾ bath, and second living room with French doors to the porch. There is a large, functional mudroom for all your gear. Upstairs is the primary suite with steam shower and two very generous bedrooms and another renovated bath. Located 3.5 from the town green on a paved road, and close to 3 ski resorts, this unique property provides a wonderful place for living, working, or vacationing. View the video tour and look at the attachments for all the recent improvements.
Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system, updated electrical wiring, windows designed to match the original style, and solar panels that make the home largely self-sufficient. Inside, the home features large, inviting rooms, including a country kitchen with a working Glenwood stove, a spacious living room, and a generous dining room perfect for entertaining. The first floor offers one bedroom and a half bath, while the second floor includes three additional bedrooms and a 3/4 bath. Set on 33 stunning acres, the land includes a serene pond and river ideal for swimming or fishing, five outbuildings, and a magnificent 30x80 19thcentury barn. The property is dotted with apple trees with boundless possibilities—whether you envision a horse farm, a dairy operation, an Airbnb retreat, or simply a peaceful and charming home in the countryside. The driveway and the bridge to the property are going to be moved and changed by the state the time frame uncertain at this time train runs twice a day at lower end of the property
Discover a truly exceptional, custom-built contemporary home nestled on approximately 79 breathtaking acres with panoramic views, offering the ultimate Vermont lifestyle. This versatile 4-bedroom residence features a flexible floor plan that includes a private in-law suite, perfect for extended family, guests, or additional living options. The setting is nothing short of spectacular. Enjoy two spring-fed ponds ideal for swimming and fishing, a charming sugar house, and an enchanting treehouse tucked among the trees. Sports enthusiasts will love the full-size tennis court, while hobbyists and makers will appreciate the oversized detached garage, perfect as a workshop or studio space. Recent updates add comfort and peace of mind, including a brand-new septic system, a whole-house generator, updated appliances, new flooring and carpeting, and a freshly painted entryway. The expansive wrap-around deck invites you to relax and soak in the stunning scenery year-round. Located just minutes from Okemo Mountain and the vibrant village of Chester, this rare property is the perfect blend of seclusion, recreation, and convenience. Whether you are looking for a family compound, private retreat, or year-round residence, this one-of-a-kind estate has it all.
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