$445,000 $115 per sq.ft. Chester VT Home »

Price Change! Reduced by $30,000 down 7% on August 23rd 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

$549,000 $223 per sq.ft. Chester VT Home »

Waterfront on Pond
4 Beds | 3 Baths |   Total Sq. Ft. 2464  |  Acres: 2.13
Wednesday Apr 29, 2026
Description: Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day's end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical. See MLS Property & Listing Details & 47 images.

$610,000 $320 per sq.ft. Chester VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1908  |  Acres: 12.86
Monday Aug 24, 2026
Description: Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for. Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide confidence and convenience for years to come. Inside, the practical floor plan includes a desirable first-floor primary bedroom and first-floor laundry, making everyday living comfortable and accessible. The remaining bedrooms offer flexibility for guests, a home office, hobbies, or creative space. Step outside to enjoy beautifully landscaped grounds, a spacious deck built around an above-ground pool, and the quiet surroundings that define rural Vermont living. Multiple barns and sheds provide exceptional versatility, whether you're looking for a workshop, tractor or recreational vehicle storage, equipment space, or even a former horse stall ready for new possibilities. Combining privacy, usable acreage, and a property that has been lovingly maintained over the years, this home offers the opportunity to enjoy country living without sacrificing comfort. Whether you're looking for room to spread out, space for projects, or simply a peaceful place to call home, this property is ready to welcome its next owners. See MLS Property & Listing Details & 47 images.

$789,000 $215 per sq.ft. Chester VT Home »

Price Change! Reduced by $60,000 down 8% on July 24th 2026
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.

$900,000 $321 per sq.ft. Chester VT Home »

Price Change! Reduced by $25,000 down 3% on August 13th 2026
5 Beds | 3 Baths |   Total Sq. Ft. 2800  |  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. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/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.

$1,200,000 $363 per sq.ft. Chester VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3308  |  Acres: 7.8
Monday May 11, 2026
Description: Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation. Inside, you'll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study. The screened front porch captures the essence of Vermont living perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the fire pit beneath star filled skies, surrounded by the natural beauty and privacy of the property. A standout feature is the remarkable multi-level 55' x 40' barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use. Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small town charm that make Vermont so special. See MLS Property & Listing Details & 39 images. Includes a Virtual Tour

$1,490,000 $276 per sq.ft. Chester VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 5400  |  Acres: 18
Friday May 8, 2026
Description: Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design. Inside, the home is defined by warm, handcrafted details wide plank wood floors, paneled walls, layered moldings, and reclaimed beams create a sense of comfort and authenticity throughout. The scale and layout offer a balance of inviting gathering spaces and quieter rooms, well suited for both everyday living and hosting. Originally operated as a bed and breakfast, the home was thoughtfully designed to welcome guests while maintaining a natural flow and sense of privacy. The surrounding land provides a peaceful and private setting, with stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch woven into the natural landscape. Open areas and wooded sections create a property that feels both curated and comfortably natural, offering space to explore, relax, and enjoy Vermont's changing seasons. A guest house and dedicated woodworking barn add to the property's appeal, offering flexibility for hosting, hobbies, or creative pursuits. Ideally located near the charming village of Chester, the property offers convenient access to year-round outdoor recreation, including skiing, hiking, biking, fishing, and scenic trails. Throughout the home, the builder's attention to detail is unmistakable, with thoughtfully crafted custom woodwork and timeless finishes that reflect a genuine commitment to quality and design. Quiet, private, and rooted in tradition, this is a property well suited for those seeking a classic Vermont retreat and lifestyle. See MLS Property & Listing Details & 53 images. Includes a Virtual Tour

$579,000 $229 per sq.ft. Chittenden VT Home »

Price Change! Reduced by $80,000 down 14% on August 26th 2026
Waterfront on River East Creek
4 Beds | 2 Baths |   Total Sq. Ft. 2532  |  Acres: 1.2
Thursday Jun 18, 2026
Description: Must see, new price! 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

$450,000 $157 per sq.ft. Clarendon VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2868  |  Acres: 2.75
Wednesday Aug 12, 2026
Description: Enjoy the space, privacy, and versatility of this 4-bedroom, 2-bathroom home set on a private 2.75-acre lot. The contemporary open-concept first floor offers a comfortable layout designed for both everyday living and entertaining, featuring a spacious kitchen, living area, and a convenient primary bedroom with its own bathroom. The lower level provides plenty of additional living space, with three bedrooms, an office, a bonus room, and a laundry room. The bonus room is perfect for children, a playroom, media space, or hobbies, while the office offers a quiet place to work from home. With room for a large family, visiting guests, or use as a ski home, this property offers flexibility to fit a variety of lifestyles. Step outside and enjoy the large front deck, perfect for relaxing, dining, or entertaining while taking in the peaceful surroundings. The three-bay garage provides abundant space for vehicles, recreational equipment, tools, and storage. The spacious backyard offers plenty of room for gardening, pets, children, outdoor activities, and gatherings. A private setting with generous indoor and outdoor space, this home offers the combination of comfort, functionality, and room to enjoy everything the property has to offer. See MLS Property & Listing Details & 32 images.

$659,000 $232 per sq.ft. Clarendon VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2840  |  Acres: 7.01
Monday Jun 1, 2026
Description: This lovely Craftsman-designed one-level, 2,800 square foot home feels as though it belongs in La Cottage magazine. Built in 1982 and lovingly maintained by the same family for 32 years, this special property has been the backdrop for a lifetime of memories. Set on seven beautiful acres in Clarendon, Vermont, the property offers privacy, perennial gardens, a large spring-fed pond, and a three-car garage. The pond has been the centerpiece of countless summers, with children spending endless hours swimming, fishing, and playing from the floating dock that has provided years of fun and laughter. Inside, the home features four bedrooms and four baths, including a primary suite with a private bath, a guest bedroom, and two bedrooms connected by a charming Jack-and-Jill bath. A dedicated home office provides the perfect space for today's lifestyle. The heart of the home is the expansive great room, where oversized windows bring the outdoors in and create a screened-porch feel during the warmer months. Oak hand-pegged flooring, a pellet stove, and a mini split system provide warmth, character, and comfort throughout the seasons. Thoughtful details and quality craftsmanship throughout reflect the timeless appeal of the Craftsman style. Step outside and you'll discover a setting that is truly one of a kind. A gazebo overlooking the pond offers the perfect place to relax, entertain, and create your own lasting family traditions. The perennial gardens are simply stunning, reminiscent of a Martha Stewart magazine, with colorful blooms and thoughtful landscaping at every turn. The full basement features high ceilings and offers tremendous potential for additional living space, recreation areas, or storage. Rarely does a property combine such charm, character, acreage, and recreational enjoyment in one beautiful package. Centrally located between Manchester and Rutland for shopping, dining, and minutes to both Killington and Okemo ski areas. LIVE VT. See MLS Property & Listing Details & 37 images. Includes a Virtual Tour

$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. See the Youtube walk-through video in this listing's branded video URL. See MLS Property & Listing Details & 60 images.

$859,000 $277 per sq.ft. Clarendon VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 4300  |  Acres: 1.78
Tuesday Aug 25, 2026
Description: Set against a backdrop of mountain views, this 4 bedroom, 5-bathroom Clarendon home delivers 4300 sq ft of finished beautifully crafted versatility, modern comfort and unmistakable Vermont Character. Natural woodwork and hardwood floors bring warmth throughout, while radiant floors on the first level keeps chilling mornings comfortable. The Eat-in kitchen offers cherry cupboards, a peninsula island, propane range and opens directly to the dining room enhanced by the wood stove. A large living room and a first floor office space could be used as a first floor bedroom. Second floor primary suite features a jetted tub and private balcony, while two additional bedrooms provide flexibility for guest and cathedral ceiling in the hallway creates the feeling of space. The lower level family room adds valuable space for casual entertaining with a wet bar, media room/gym or a huge office space. Outside, the generous lot offers room to unwind, garden space, while enjoying the scenery of mountain views or relax on the inviting front porch or entertain on the back deck. Clarendon Gorge, hiking, the Historic Kingsley Covered bridge and Rutland-Southern Regional airport are nearby. Killington Ski Area & Okemo are just a short drive away. See MLS Property & Listing Details & 60 images.

$650,000 $430 per sq.ft. Corinth VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1512  |  Acres: 135
Wednesday Nov 13, 2024
Description: Here is your opportunity to own a piece of Vermont and live the Vermont Lifestyle you've always wanted. This property offers acreage on both sides of Chelsea Road. About 32+/- acres on one side and the remaining 133+/- acres and single family residence on the opposite side. The exterior has recently been painted and some inside work has been completed. Keep it as is for that country living or bring your plans and ideas to make this home meet your needs. This property has so much to offer, open pasture land, wooded acreage, and a brook across the road to cool off in on those hot summer days. With this much acreage its a perfect chance to establish your own hiking or equestrian trail system, become the gardener you always wanted to be or just be at peace with nature and all it has to offer. Relax on the porch enjoying the wildlife, the beautiful distant mountain views or unwinding with a good book. What a great way to experience Vermont's beauty. Embrace the peace and tranquility this single family residence has to offer. Being sold "as is" "where is". All measurements are approximate. See MLS Property & Listing Details & 35 images.

$975,000 $501 per sq.ft. Corinth VT Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1948  |  Acres: 80
Monday Aug 24, 2026
Description: 1850 New England Farmhouse sitting with a commanding position on 80 acres of rolling, usable landscape with multiple connected outbuildings, detached barn/garage structure and in-ground pool with pool house. This is a once-in-a-lifetime opportunity, complete with a plug and play living space in the main house along with multiple opportunities throughout the structures and landscape for an entrepreneurial or enthusiastic party. This home has been loved and cared for as a family property with a large porch overlooking the in-ground pool and front yard, as well as a large, open kitchen with attached dining area adjacent to the spacious living room with built in shelving, as well as the laundry room and first floor full bathroom. The second level of the home has the four bedrooms, as well as access to the attic spaces of the attached barn structures with the removal of winterization behind a closed door. Each bedroom has adequate space for desks, furniture, or working space if additional bedrooms are not needed. The attached barn continues both above and below grade, with space to be used for agricultural endeavor, automotive endeavors, or whichever pursuits your imagination can create that fit within the space. The detached barn/garage structure has great potential as well. Modern electrical work has recently been performed in the barn structures, and the entirety of the primary residence is modern and upkept. Choose between burning wood or oil in the forced air unit for the home, use the rolling landscape for farming endeavors or for recreational pursuits. Come and see how your vision can apply to this unique property. See MLS Property & Listing Details & 38 images.

$1,795,000 $739 per sq.ft. Corinth VT Home »

Waterfront on Pond
4 Beds | 4 Baths |   Total Sq. Ft. 2430  |  Acres: 177.9
Monday Jun 15, 2026
Description: Taplin Hill Farm conveys a sense of quiet, privacy, and connection to the Vermont countryside. The 180± acres of rolling pasture, woodland, stone walls, trails, and open sky frame sweeping views to the White Mountains. From the ridge, the pond, and the farm's many lookout points, the landscape unfolds with a calm and natural beauty that feels both expansive and deeply peaceful. The property includes three distinct dwellings, each offering its own experience of the land. Cabin Hill is a secluded off-grid cabin high above the valley with a kitchenette, full bath, and expansive deck overlooking the mountains. The Modern Farmhouse blends antique and contemporary design with two comfortable bedrooms, large windows, and views across the fields and hills. The Cottage on Mulligan's Pond overlooks the pond with a full kitchen, screened porch, upper-level deck, and quiet spaces for work, rest, or guests. With miles of trails, open fields, wooded paths, a pond, and grazing Scottish Highland cattle and horses nearby, Taplin Hill Farm offers an inviting combination of privacy, simplicity, and Vermont hill country beauty. Located approximately 30 minutes from Hanover and 40 minutes from Montpelier, this thoughtfully maintained farm property is prepared for the next generation of owners to enjoy. See MLS Property & Listing Details & 31 images. Includes a Virtual Tour