$249,500 $130 per sq.ft. Chester VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 1922  |  Acres: 2
Wednesday Jul 1, 2026
Description: Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits. The home is currently configured as two charming apartments, each showcasing timeless character with features such as stained-glass windows, soaring ceilings, and abundant natural light. The first-floor apartment boasts a beautiful brick fireplace with a classic hearth in the kitchen and opens directly onto a private patio, creating a warm and inviting living space. The impressive barn includes a heated workshop area, making it ideal for artisans, contractors, mechanics, or anyone needing year-round workspace. Whether you're looking to establish a small business, expand your existing operation, or simply enjoy the flexibility of extensive storage and workspace, this property offers endless possibilities. Conveniently located on Route 103 between Chester, Springfield, and Ludlow, the property provides excellent visibility, easy access, and ample parking for customers, clients, and guests. See MLS Property & Listing Details & 38 images.

$460,000 $119 per sq.ft. Chester VT Home »

Price Change! Reduced by $15,000 down 3% on July 14th 2026
5 Beds | 4 Baths |   Total Sq. Ft. 3865  |  Acres: 0.44
Thursday Jun 18, 2026
Description: Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning fireplace and a large entertainment room complete with a wet bar, creating an ideal setting for gatherings, celebrations, or relaxing at home. The thoughtfully designed primary suite features a beautiful en-suite bathroom, while first-floor laundry adds everyday convenience. The flexible floor plan provides abundant space for family, guests, remote work, hobbies, or multi-generational living. Outside, a paved driveway leads to a detached one-car garage, and the level backyard offers plenty of room for recreation, gardening, pets, or outdoor entertaining. Mature trees and established landscaping create a natural buffer from the road, providing a sense of privacy while remaining just moments from Chester's village amenities, shops, restaurants, and community events. Combining historic character, generous living space, and a highly desirable location, this is a rare opportunity to own one of Chester's classic homes. Conveniently located just minutes from I-91 and within easy reach of Okemo Mountain Resort, Magic Mountain, Bromley Mountain, Stratton Mountain, and other Southern Vermont outdoor destinations, this property offers year-round access to skiing, hiking, recreation, and travel throughout the region. See MLS Property & Listing Details & 58 images. Includes a Virtual Tour

$489,000 $301 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1626  |  Acres: 0.33
Thursday Jun 18, 2026
Description: Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with butcher block counters, attractive center island with Vermont marble counter, stainless steel sink and dishwasher framed by a wall of windows with a picturesque valley view. A spacious first-floor bedroom, full bath and convenient laundry area provide easy one-level living. Upstairs, two additional bedrooms with generous closets share a stylish full bath finished with classic subway tile. Recent upgrades include energy efficient systems and a new four-bedroom leach field, offering peace of mind for full-time residents, second-home owners, or investors. Offered fully furnished, this turnkey Vermont property has a proven history as a successful seasonal rental. Experience the vibrant community of Chester, with its charming village shops and restaurants, town pool, recreation area, premier disc golf course, pickleball and tennis courts, snowmobile club, and thriving artisan culture. Ideally located near Okemo Mountain Resort and Magic Mountain ski areas. This quintessential Vermont home is equally suited as a primary residence, ski getaway, vacation home, or income-producing investment property. See MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$495,000 $275 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1800  |  Acres: 2
Wednesday Jun 17, 2026
Description: This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached garage. This light-filled home with two floors of living (plus a multi-room lower-level walkout ready to finish) has great open space on the main level. The kitchen with updated granite counters is open to the dining area which has a sliding door to the large back deck. This is the perfect space to have dinner overlooking the landscaped back yard. Try your green thumb in the vegetable garden that is ready for planting. The living room is also connected to the dining area making this space perfect for friends and family to gather. A convenient bedroom and bathroom complete this level. Upstairs are two generous bedrooms, a bonus room for a home office or more plus space above the garage that is currently being used as an amazing walk-in closet. Come and take a look at this low-maintenance home in a park-like setting with berry bushes, fruit trees, a gazebo, and a combination garden and wood shed. The stone firepit could be a favorite spot for relaxing by the fire after a day on the slopes. There is a third bay workshop next to the attached garage and an additional detached garage that has a vent pipe for a wood stove and can be of multiple uses. This property will check boxes that you didn't even know you had! See MLS Property & Listing Details & 60 images.

$649,000 $294 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2204  |  Acres: 1
Wednesday Jul 1, 2026
Description: Joins us for a gallant OPEN HOUSE Friday, July 17th from 3-6PM...serving cold drinks and shrimp cocktails! Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and quiet reflection. Step inside to discover warm, curated interiors where a matching floor-to-ceiling indoor fireplace anchors a cozy great room...an ideal focal point for gatherings and quiet nights in. The custom kitchen is a chef's and designer's showcase making meal prep effortless and stylish. Cute, artful decor and exceptional millwork accentuate every room..every little detail has been considered and executed with eye-popping precision. Natural light pours through thoughtfully placed windows, highlighting textures, finishes, and curated vignettes around nearly every corner. In addition to the four private bedrooms, the special loft above the second-floor den offers a "fun" sleeping area and great retreat for the "kids". Unique sightlines and charming nooks reveal something special at every turn.unexpected architectural details, refined accents, and cozy gathering spots create a home rich in personality and comfort. The floorplan flows intuitively while offering distinct spaces for entertaining and everyday living. Practicality meets luxury with a spacious second garage providing room for toys, workshop space, or secure storage perfect for multi-vehicle households or hobbyists. The gated setting ensures peace of mind and exclusivity, while the manicured wooded grounds offer a serene backdrop and a strong connection to nature. Only 10 miles from world-class skiing at Okemo and golf at Fox Run...then enjoy the 5 lakes of Okemo Valley and the nearby VAST trails! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$750,000 $442 per sq.ft. Chester VT Home »

Waterfront on River Williams River
3 Beds | 2 Baths |   Total Sq. Ft. 1695  |  Acres: 6.03
Wednesday Jul 1, 2026
Description: Tucked away on a quiet country road in one of Chester's most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle, just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside, the main level centers around a commanding, floor-to-ceiling fieldstone wood-burning fireplace, beautifully complemented by rich hardwood floors and a bespoke custom kitchen. Designed for privacy, the primary suite features a spa-like ensuite bath, while two additional guest bedrooms and a 3/4 bath provide plenty of space for family or weekend visitors. Intelligently designed for flexible living, the upper-level loft serves as an inspiring home office or studio, while the bright, walk-out lower level offers incredible potential for a game room, home gym, or ski lounge. Transition effortlessly outdoors to the oversized front deck for morning coffee, or unwind in the expansive screened porch out back listening to the sound of the river. The detached, insulated, oversized, 2-bay, 2-level barn has full electrical service, electric garage doors, and a workshop with extra storage space. There is a greenhouse perfect for gardening. With direct access to nearby VAST trails for winter recreation, this is a true four-season retreat. Visit the Okemo real estate today. Taxes are based on the current town assessment. See MLS Property & Listing Details & 59 images.

$849,000 $231 per sq.ft. Chester VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 4388  |  Acres: 11.24
Wednesday Jul 1, 2026
Description: Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to detail create a residence as enduring as it is beautiful. A flexible floor plan offers five bedrooms and three baths, including an elegant first-floor primary suite with ensuite bath, complemented by additional main-level bedroom options ideal for guests, multi-generational living, or a dedicated home office. Upstairs, two spacious bedrooms each feature adjoining bonus rooms perfectly suited as executive offices, dressing rooms, studios, or generous walk-in closets, while additional unfinished space presents exciting opportunities for future expansion. Designed for effortless entertaining and comfortable everyday living, the heart of the home is an open-concept kitchen, dining, and living area filled with natural light. A handsome library offers a quiet retreat, while integrated whole-home audio enhances the experience throughout. An oversized laundry and mudroom connects seamlessly to the attached two-car garage, delivering exceptional convenience without compromising design. Outside, mature gardens, specimen trees, and thoughtfully curated outdoor living spaces create a setting of remarkable beauty and privacy. Relax beneath the covered porch, entertain with family and friends, or simply enjoy the peaceful surroundings. Ideally located just minutes from Okemo, Stratton, Magic, and endless four-season recreation, yet within walking distance of Chester's vibrant village, this exceptional property offers a rare combination of privacy, convenience, and refined Vermont living. A home of lasting quality, exceptional versatility, and unmistakable character! See MLS Property & Listing Details & 44 images.

$925,000 $397 per sq.ft. Chester VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2328  |  Acres: 14.1
Tuesday Jul 14, 2026
Description: Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Upstairs, you'll find three additional bedrooms, a full bath, a comfortable den, and a loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment. See MLS Property & Listing Details & 58 images.

$649,000 $256 per sq.ft. Chittenden VT Home »

Price Change! Reduced by $10,000 down 2% on July 8th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2532  |  Acres: 1.2
Thursday Jun 18, 2026
Description: New Price! Must see! Welcome to 275 Chittenden Road, a classic Vermont Farmhouse fully refinished set on 1.2 level acres with frontage along East Creek. Offering 4 bedrooms, 2 full baths, and 2,532 finished square feet, this 1850 home blends historic charm with warm, updated living spaces and flexible options for today's lifestyle. This fully remodeled home from the studs must be seen in person to fully enjoy. Featuring exposed beams, refinished wide plank wood flooring, tiling in the kitchen and all baths no detail was missed. The additional rec room with vaulted ceilings offers the space for all of your entertaining needs. The kitchen is well appointed with marble countertops and attached dining. Step onto the screened in seasonal porch to enjoy the sound of the East Creek rolling by. Enjoy single level living with a bedroom, bath and laundry on the main floor. The property also includes a versatile accessory unit with one bedroom, its own kitchen, and a living room, offering excellent flexibility for guests, extended household needs, a private work-from-home setup, or other uses subject to local approvals. Outdoor living is just as inviting, with a covered porch, screened porch, open yard space, and the sights and sounds of the creek. Located in scenic Chittenden, Vermont, this Rutland County setting is known for its peaceful rural character and access to year-round recreation. Enjoy proximity to hiking, fishing, snowshoeing, within 30 minutes of skiing, Chittenden Reservoir, Chittenden Brook, and the broader Green Mountain region, while still having local conveniences and nearby Rutland-area amenities within reach. This home has it all, nice finishes, low maintenance with heating systems and electrical all updated, beautiful landscaping, porches and decks to enjoy, a beautiful flowing creek in the back yard and flexibility in living accommodations. The property is offered fully furnished less a few personal items. This is a must see to fully appreciate! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$300,000 $234 per sq.ft. Clarendon VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1280  |  Acres: 1
Thursday Jul 9, 2026
Description: Wait until you see this view....Unbelievable, long distant view over meadow to hillside to mountains beyond. Every day would be different and remarkable and the sunsets can't be beat. You will appreciate the screen porch in the front. You will undoubtably spend hours there. This 16x80 foot mobile home has 3 bedrooms, 1 with a private bath. The home was built in 2007 and is in nice condition. The kitchen is handsome, and there is a private deck off the back. Steps away from the house is a 32x24 garage with 10-foot ceiling. There's a woodstove out there. If you have any handy men in the family, you know where they will be. Upstairs above the garage is an accessory dwelling unit with a private deck off the back. There is a kitchen/living room, a bedroom, a small office and a 3/4 bath. There's a pellet stove as well. The back of the property is a gently sloping lawn area. It could definitely be home to chickens or four-legged creatures or a giant garden spot. The location is super convenient. It's just a 1/2 mile off Route 7 so it's an easy commute to anyone that works in the area as well as shopping or medical. But being a part of a small town has great benefits..community, neighborhood, local school and more. It's not far from Killington or Okemo. Plenty of outdoor opportunities nearby. Don't wait. Come have a look at all that is offered here. See MLS Property & Listing Details & 40 images.

$300,000 $216 per sq.ft. Clarendon VT Home »

Waterfront on River Mill River
3 Beds | 1 Baths |   Total Sq. Ft. 1388  |  Acres: 1
Tuesday Jun 30, 2026
Description: Step into the timeless charm of this picture-perfect 1925 Vermont country cottage, where character, comfort, and a lifetime of love come together. Offering 3 bedrooms, 1 full bath, and convenient first-floor laundry, this home is as inviting as it is functional. From the moment you arrive, you'll be captivated by the large screened-in front porch--the perfect place to enjoy your morning coffee or unwind while taking in the peaceful surroundings. Situated on a spacious corner lot, the property offers endless opportunities for gardening, raising chickens, or simply enjoying the outdoors. Complete with a charming chicken coop, gardening shed, oversized 2-car garage, and bonus storage space off the back of the garage, there's room for all your hobbies and projects. The backyard is truly something special, backing up to the Mill River and the picturesque Kingsley Mill Covered Bridge, creating a quintessential Vermont setting that's hard to find. Lovingly cared for by the same owners for the past 67 years, this home radiates warmth and pride of ownership. Their hearts and souls have been poured into every corner, creating a welcoming atmosphere you can feel the moment you walk through the door. Cute as can be and ready for its next chapter, this beloved cottage is waiting for someone new to make it home. See MLS Property & Listing Details & 31 images.

$355,000 $205 per sq.ft. Clarendon VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1735  |  Acres: 5.5
Wednesday Jun 17, 2026
Description: Classic Vermont Farmhouse on 5.5 picturesque acres in Clarendon. Enjoy country living with a covered front porch, beautiful stone wood-burning fireplace, detached garage, and workshop. The open land has a history of agricultural use, including Christmas trees, horses, and livestock, offering excellent hobby farm potential. Conveniently located just 10 minutes to downtown Rutland and 5 minutes to Rutland Southern Vermont Regional Airport, combining rural charm with easy access to town amenities. Open House this Saturday June 20th from 10:30 to noon. See MLS Property & Listing Details & 36 images.

$429,000 $195 per sq.ft. Clarendon VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2200  |  Acres: 2.13
Thursday Jun 25, 2026
Description: Set on 2.13 private acres in North Clarendon, this unique "as is" property offers a rare opportunity for buyers seeking space, versatility, and potential. The property includes a ranch style single family home, and a two-stall barn with two one-bedroom apartments, along with two outbuildings, creating a variety of possibilities for owner-occupants, investors, hobby farmers, or those looking for a multi-generational living arrangement. Surrounded by the natural beauty of Vermont's Green Mountains, the setting is peaceful and private while remaining conveniently located near Rutland, outdoor recreation, shopping, dining, and regional air travel. The open meadow provides room for horses, small livestock, gardening, or simply enjoying the country landscape. Outdoor enthusiasts will appreciate easy access to Clarendon Gorge, the Long Trail, and nearby skiing at Killington and Pico. The property is being offered in as-is condition and presents an excellent opportunity for buyers willing to make improvements and unlock its full potential. With a desirable location, usable acreage, existing rental units, and solid underlying value, this property offers a chance to create something truly special. Come to the Public Open House this Friday June 26th from 1pm to 3pm; or schedule your own private showing today and explore the possibilities. See MLS Property & Listing Details & 47 images.

$599,000 $358 per sq.ft. Clarendon VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1672  |  Acres: 17
Friday Jul 3, 2026
Description: Some properties simply have to be experienced in person to be fully appreciated, and this is one of them. This charming 3-bedroom, 2.5-bath Cape sits on 17 breathtaking acres where sweeping views, a spring fed pond, mature fruit trees, blueberry bushes, and beautifully maintained grounds create an exceptional setting. The property also includes two outbuildings, including a classic barn with hayloft and stalls. A second outbuilding features upper- and lower-level garage bays, ideal for equipment, ATVs, tractors, workshop space, or additional storage. Inside, the eat-in kitchen features a large picture window overlooking western views and stunning sunsets. It flows into the living room with a cozy wood-burning fireplace and sliding glass doors leading to the back porch, the perfect spot to enjoy the sunrise. A half bath with laundry is located just off the kitchen, while the first-floor primary suite offers a walk-in closet and private en suite bath. Upstairs are two generously sized bedrooms, each with a closet, and an additional full bath. The walk-out basement offers excellent potential for future expansion and already includes a roughed-in bathroom. A two-car attached garage completes the home. Enjoy the tranquility of country living without sacrificing convenience. Located just outside of Rutland, the property is close to shopping, dining, and healthcare, and only 30 minutes from Okemo and Killington/Pico for year-round recreation. See MLS Property & Listing Details & 42 images.

$799,000 $179 per sq.ft. Clarendon VT Home »

Price Change! Reduced by $40,000 down 5% on July 15th 2026
5 Beds | 6 Baths |   Total Sq. Ft. 5975  |  Acres: 3.72
Wednesday Jun 24, 2026
Description: Sweeping Mountain Views provides a stunning backdrop for this spacious 6,000+ square foot home, offering 4 bedrooms, 4.5 baths, a flexible floor plan, and a private one-bedroom in-law apartment on 3.7 picturesque acres. Designed for both everyday living and entertainment, the main level features soaring cathedral ceilings, expansive windows, and an open-concept layout that fills the home with natural light while showcasing the surrounding Green Mountain scenery. Formal and casual living spaces flow effortlessly together, including a welcoming family room, dining area, and spacious kitchen with granite countertops and breakfast nook. The loft overlooking the main living area provides ideal space for a home office, reading area, or additional gathering space. The primary suite offers a private retreat complete with an ensuite bath, walk-in closet, private balcony, and dedicated laundry room. The recently refreshed lower-level apartment features new flooring, fresh paint, a full bath, and its own living space--perfect for extended family, guests, multigenerational living, a home business, or supplemental income potential. Additional highlights include comfortable radiant floor heat, central vac, hardwood flooring, multiple outdoor living spaces, including a brand-new composite deck and private balconies, an attached two-car garage, dedicated workshop space, abundant storage, and an energy-saving solar array. Located just minutes from world-class skiing, lakes, hiking trails, golf, and all the amenities of the Rutland Region, this property offers the perfect balance of space, comfort, flexibility, and Vermont living. Join us at the Public Open House on Friday, June 26, from 4:00 PM to 6:00 PM and experience the views, space, and possibilities for yourself. See the Youtube walk-through video in this listing's branded video URL. See MLS Property & Listing Details & 60 images.