$199,000 $151 per sq.ft. Chester VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1322  |  Acres: 3.75
Tuesday May 20, 2025
Description: 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! See MLS Property & Listing Details & 35 images.

$225,000 $170 per sq.ft. Chester VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1327  |  Acres: 0.13
Wednesday Jun 18, 2025
Description: 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! See MLS Property & Listing Details & 26 images.

$230,000 $225 per sq.ft. Chester VT Home »

Price Change! Reduced by $10,000 down 4% on August 5th 2025
3 Beds | 1 Baths |   Total Sq. Ft. 1024  |  Acres: 0.25
Thursday Jul 17, 2025
Description: Adorable Village Home in the Heart of Chester, Vermont This charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage. Inside, you'll love the warm, inviting living space with wood accents, an open-concept kitchen and dining area, and cozy bedrooms filled with natural light. The updated bath has a fresh, modern feel, and the flexible layout offers space for guests, work-from-home, or hobbies. This is more than a house -- it's a home with heart, waiting for its next chapter. Located just minutes from Chester's historic village green -- shops, dining, and year-round recreation are all close by. Whether you're looking for a starter home, Vermont getaway, or a low-maintenance lifestyle, this adorable home checks all the boxes. See MLS Property & Listing Details & 60 images.

$249,000 $472 per sq.ft. Chester VT Home »

1 Beds | 1 Baths |   Total Sq. Ft. 528  |  Acres: 2.5
Thursday Sep 4, 2025
Description: Open House Thursday, September 11, 4:00 - 6:00 Welcome to your Vermont retreat, an inviting one bedroom, one bath home sat on 2.5 acres at the end of a dead end road in Chester. This 528 square-foot cottage has been thoughtfully updated for four season, comfort, featuring full insulation, a woodstove for cozy evenings, and efficient mini-splits providing both heating and air-conditioning. Recent upgrades include a brand new three bedroom septic system, making expansion a future option and a detached two car garage that offers excellent storage for vehicles, ski gear, or workshop space, along with an electric car charging station hookup. The property is dotted with mature sugar maples, already tapped, bringing an authentic Vermont sugaring tradition right to your doorstep. Just minutes from Chester's, charming Village center, and Springfield amenities, and a short drive to Okemo Mountain resort, this location is ideal for year-round, living, a ski getaway, or a weekend retreat. Whether you're seeking a low maintenance primary residence or a charming, second home, this property blends, rustic appeal with modern convenience in quintessential Vermont setting. See MLS Property & Listing Details & 27 images. Includes a Virtual Tour

$249,500 $175 per sq.ft. Chester VT Home »

Price Change! Reduced by $49,500 down 20% on September 5th 2025
1 Beds | 1 Baths |   Total Sq. Ft. 1424  |  Acres: 3.5
Monday Aug 25, 2025
Description: The view from the road does not give you the fact that behind the house is a beautiful and private backyard! This property has great possibilities for you to create your own vision of what it can become. You could either do some improvements to the existing gambrel structure which has been a comfortable residence for many years, or you could use it as some kind of allowed business or rental and turn the really nice barn into your new house. The barn sits in a really nice spot overlooking the open landscaped property, with a nice private woodsy area behind. Offered for sale for the first time in almost 40 years! See MLS Property & Listing Details & 38 images. Includes a Virtual Tour

$359,900 $400 per sq.ft. Chester VT Home »

Price Change! Reduced by $30,000 down 8% on September 6th 2025
2 Beds | 1 Baths |   Total Sq. Ft. 900  |  Acres: 11
Saturday Jul 12, 2025
Description: This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity to Okemo for downhill skiing and snowboarding in the winter as well as the Chester village and downtown Springfield being only about a 10 minute drive to the local shops, restaurants and more. In a quiet and serene setting this cozy cabin is well maintained, private and has so much to offer! See MLS Property & Listing Details & 19 images.

$375,000 $288 per sq.ft. Chester VT Home »

Price Change! Reduced by $14,000 down 4% on August 26th 2025
3 Beds | 2 Baths |   Total Sq. Ft. 1304  |  Acres: 8.5
Tuesday Aug 12, 2025
Description: This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also features a newly built timber frame sugar style shack perfect for many different uses. There is the possibility for single level living with the downstairs bedroom being right across from the full bathroom as well as the laundry hook up's being on the first floor. In a great location just a few minutes from the quaint town of Chester 13 minutes from Magic Mountain and just 25 minutes from Okemo Mountain where there are shops, restaurants, Skiing and so much more! See MLS Property & Listing Details & 35 images.

$399,000 $147 per sq.ft. Chester VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2710  |  Acres: 1.79
Wednesday Jun 4, 2025
Description: 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. See MLS Property & Listing Details & 29 images.

$410,000 $314 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1304  |  Acres: 1
Sunday Jul 27, 2025
Description: Everything you've been looking for in a Vermont home--completely renovated with care and character. Nearly every aspect of this Chester property is new: electrical, plumbing, heating, insulation, drywall, windows, and more--offering the low-maintenance peace of mind homeowners crave. The kitchen features a stylish farmhouse sink and stone countertops, while the upstairs bathroom includes a beautifully curated vintage Martini pedestal sink. Original wide plank wood floors have been lovingly refinished, preserving a sense of warmth and history. The standing seam metal roof offers long-term durability, and outside, the expansive level lawn and massive post-and-beam barn are overflowing with potential--whether for gardening, recreation, storage, or transforming into additional living space. A standout opportunity for anyone seeking a move-in-ready home with timeless charm and room to grow. This home is in 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. See MLS Property & Listing Details & 51 images.

$425,000 $166 per sq.ft. Chester VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2562  |  Acres: 0.75
Wednesday Aug 27, 2025
Description: Historically known as the Frank Harris House, this distinguished circa 1880 Queen Anne style Victorian commercial building on .75+/- acres has long been a landmark presence in the village of Chester. With its welcoming veranda and timeless charm, the property has served as a thriving office for many years and has many period architectural details throughout such as, a unique, colored transom window in the first floor meeting room, a white brick decorative fireplace with accent mirror in the large office/reception area, graceful bay windows, a mix of hardwood and softwood floors and a slate roof with diamond patterned bands. The heating system has recently been upgraded with a new direct vent boiler and efficient hydronic wall units to ensure comfort throughout the seasons. Additional features include a spacious kitchen area, 1.5 baths, a handicap access ramp and public water and sewer. The attached rustic two-story barn offers additional storage space and there is a large, second story three-season porch! Whether your vision involves refreshing the property for use as office space, transforming it to a multi-unit investment property or restoring it to a grand, single family home, the Harris House presents a rare opportunity--centrally located in the heart of Chester and within walking distance to the town green, shops, elementary school and recreation area. Also listed as under MLS #5058558. See MLS Property & Listing Details & 41 images. Includes a Virtual Tour

$450,000 $260 per sq.ft. Chester VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1728  |  Acres: 1.12
Friday Mar 1, 2024
Description: 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! See MLS Property & Listing Details & 53 images.

$495,000 $214 per sq.ft. Chester VT Home »

Price Change! Reduced by $100,000 down 20% on July 24th 2025
6 Beds | 1 Baths |   Total Sq. Ft. 2308  |  Acres: 34.9
Monday Jun 16, 2025
Description: 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! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$565,000 $312 per sq.ft. Chester VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1812  |  Acres: 0.81
Monday Sep 1, 2025
Description: The Stone Cottage began its long history as a schoolhouse built as the Civil War was nearing its conclusion in 1864. Scottish craftsmen from the Aberdeen region constructed the sturdy structure using a technique referred to as 'snecked ashlar' with hewn ashlar stones laid in horizontal and vertical courses with spaces filled with smaller 'snecks joined with mortar. The random patchwork yields a strong and handsome bond that endures the harsh climates of Scotland and Vermont. Comprehensively renovated 25 years ago the home centers around great room featuring a substantial stone fireplace with vaulted wood paneled ceiling and a wall of windows overlooking the Williams River below. The gracious country kitchen is accented with custom cherry cabinets, built-in dish hutch, granite topped island and expansive bay windows next to the kitchen table and a sliding glass doors opening out to a wide stone paved patio. The light and airy primary bedroom and ensuite bath is located on the second floor, and the private guest quarter bedroom is sited on the lower level with walk-out access to a sitting area above the scenic waterfront. The detached 3 level gambrel barn-garage offers potential for a variety of uses including a workshop and additional residential accommodation. Chester's famous 'Stone Village' is nearby and the Okemo Ski is a 20 minute drive away. See MLS Property & Listing Details & 53 images. Includes a Virtual Tour

$599,000 $156 per sq.ft. Chester VT Home »

7 Beds | 4 Baths |   Total Sq. Ft. 3850  |  Acres: 0.75
Wednesday Jun 18, 2025
Description: 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). See MLS Property & Listing Details & 60 images.

$599,900 $223 per sq.ft. Chester VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2689  |  Acres: 6
Wednesday Sep 10, 2025
Description: You have got to see this stunning, fully renovated home, rebuilt from the studs up with meticulous attention to detail while maintaining its classic New England charm! Perfectly perched on the picturesque rolling hills of desirable Chester, this 4bdrm, 3bath beauty offers the ideal balance of comfort, elegance, and modern functionality. Set on 6 private acres overlooking open fields and peaceful pastures, this home is designed to take full advantage of its breathtaking surroundings. Step inside and you're greeted by a spacious, sun-filled kitchen and dining area where large windows frame panoramic views of the countryside. The easy flow and layout blends seamlessly, perfect for entertaining friends, hosting family gatherings, or simply relaxing by the warmth of the Vermont seasons. The 1st floor primary bedroom, 3/4 bath, and laundry room offer an ideal layout for aging in place. Upstairs, you'll find a primary en suite, 2 addtl bdrms, and a full bath, giving everyone their own space and privacy. A full basement provides excellent storage, hobby, or workshop space. Every aspect of this home has been thoughtfully reimagined, from the quality craftsmanship to the modern finishes, offering a true turn-key living experience in one of Vermont's most desirable locations. Outside, enjoy six acres of serene land with plenty of room for gardens or outdoor recreation. Easy access to skiing, hiking, biking, and endless outdoor adventures, I-91, Dartmouth Hospital and more. See MLS Property & Listing Details & 39 images.