$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.

$325,000 $98 per sq.ft. Chester VT Home »

Price Change! Reduced by $24,000 down 7% on June 14th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3332  |  Acres: 2
Friday May 8, 2026
Description: Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops and appliances. The main level offers a bedroom, dining room, office space and living room. All of the windows have been replaced (except in the attic), updated electric panel, insulation done by Efficiency VT, new stoves in the barn room and living room (see MLS docs for the complete list). This property is perfect for anyone looking for a TRUE Vermont home with loads of potential. Great natural light, large bedrooms, hardwood floors and attached garage. One of the features I personally love is the screened stone patio (barn room) off the back of the house. The rustic beams and barn boards with wood stove is a wonderful space to relax and entertain. Above is unfinished space ready for your ideas, work out space? yoga studio? game room? There are pretty perennials and gardens surrounding the home. The back yard is private with attached shed space and back deck. Chester is a wonderful community and this home is perfectly situated for easy access to I91, Grafton, ski resorts, shopping and walking to the village green. The sellers have loved owning this home and have created many many memories here. Don't miss your chance to be the next stewards of this truly special property. See MLS Property & Listing Details & 41 images.

$399,000 $186 per sq.ft. Chester VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2148  |  Acres: 1.5
Tuesday Jan 6, 2026
Description: This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of living space 4 bedrooms, 2.5 bathrooms. It sits on the banks of the Williams River on a dead end street and treed backyard area. First floor consists of a large kitchen and livng room and a half bath. The second floor has a beautiful sized primary bedroom with ensuite bathroom. There are also 3 bedrooms and a 3/4 hallway bathroom. See MLS Property & Listing Details & 37 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

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

Price Change! Reduced by $20,000 down 4% on May 22nd 2026
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.

$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 $325 per sq.ft. Chester VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2850  |  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. OPEN HOUSE SATURDAY JULY 11TH 10:00am to 12:00pm See MLS Property & Listing Details & 39 images. Includes a Virtual Tour

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

Price Change! Reduced by $200,000 down 13% on May 28th 2026
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. OPEN HOUSE SATURDAY JULY 11TH. 1:00PM to 3:00pm See MLS Property & Listing Details & 53 images. Includes a Virtual Tour

$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

$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.

$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. 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.

$895,000 $336 per sq.ft. Clarendon VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2660  |  Acres: 10.75
Wednesday Mar 25, 2026
Description: Welcome to Elm Hill, a fine residence situated atop a knoll to capture the mountain views and Vermont's natural beauty. Thoughtfully designed for both comfortable everyday living and effortless entertaining, this well-built and attractive home offers a flexible floor plan suited to a variety of lifestyles. Many of the home's thoughtful features make everyday living effortless, including an open-concept layout, a separate home office ideal for today's work-from-home lifestyle, and abundant closet and storage options throughout. A convenient mudroom entry, oversized three-car garage, and a highly usable basement further enhance functionality, offering excellent storage and potential for future expansion. Over the years, the property has been carefully updated and maintained, reflecting true pride of ownership. Highlights include a newly renovated bathroom with high-quality finishes, newer mechanical systems, and roof, and the recent addition of energy-efficient heat pumps providing year-round heating and cooling. A fully screened porch stretches across the front of the home, offering the perfect place to relax and unwind while extending your living space during the warmer months. Completing the property is a charming, professionally designed and built 273 sq ft guest house--ideal for visitors, extended family, or additional income potential. Set on over 10 acres, the property features a partially fenced yard, established perennials, natural landscaping, open field, a gentle stream, and a wooded lot--creating a perfect blend of beauty, privacy, and usable outdoor space. Located in Clarendon, this property offers the perfect blend of peaceful country living with convenient access to nearby amenities. Just a short drive to Rutland, with its shopping, dining, services, a regional airport, and an Amtrak station for easy travel. Outdoor enthusiasts will love the close proximity to skiing, hiking trails, and scenic cycling routes that showcase Vermont's beauty in every season. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$899,000 $290 per sq.ft. Clarendon VT Home »

Price Change! Reduced by $91,000 down 10% on June 12th 2026
5 Beds | 5 Baths |   Total Sq. Ft. 4300  |  Acres: 1.78
Monday Feb 23, 2026
Description: Welcome to 49 Sherri Lane in Clarendon, Vermont, a private mountain-view sanctuary set in a peaceful Rutland County neighborhood. This thoughtfully renovated home blends Vermont character, modern comfort, and generous living space with sweeping mountain views in every season. The main level features a foyer, living room, eat-in kitchen, dining room, and bedroom, offering flexible everyday living. Hardwood and softwood flooring, radiant heat, central air conditioning, and abundant natural light create a warm, inviting feel throughout. Upstairs, the second level showcases a vaulted ceiling, exposed beams, and a dramatic arched window framing the surrounding scenery. The second-level primary suite includes a jetted soaking tub, walk-in closet, and private balcony overlooking the views, with additional bedrooms and full baths nearby. The finished walkout lower level offers excellent flexibility for a family room, guest space, recreation area, home office, or media room, with one full bath and direct backyard access. Updated bathrooms, modern finishes, and an attached multi-bay garage with unfinished space above add function and future potential. Located near Rutland, Killington, Pico, Lake Bomoseen, hiking, skiing, dining, and year-round Southern Vermont recreation, this Clarendon VT home for sale offers privacy, comfort, views, and four-season Vermont lifestyle appeal. Welcome Home! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour