New Listing! Cavendish VT Home for sale $379,000 $253 per sq.ft.

$379,000 $253 per sq.ft. Cavendish VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1496  |  Acres: 0.16
Listed on Thursday May 1, 2025
Description: This home has served as a primary residence and also as an income-producing rental and can be sold furnished. While the upper level of this home has three bedrooms, the walk-out lower level of the home has such potential as well. It is currently partially finished and is being used as a family room and for storage. The large deck on the end of the house is perfect for taking in some fresh Vermont air or grilling for friends and family. Perhaps this is the reasonably-priced property not needing a lot of work that you have been waiting for? Become part of the Cavendish Community and have access to many ski mountains including Okemo. This property is a quick drive from Rt 91. OPEN HOUSE Saturday May 3 from 11am-1pm. See Listing Details & 19 images.

New Listing! Chelsea VT Home for sale $299,000 $155 per sq.ft.

$299,000 $155 per sq.ft. Chelsea VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1932  |  Acres: 2
Listed on Monday Apr 28, 2025
Description: Welcome to your dream Vermont retreat! This beautifully maintained, two-story gambrel-style farmhouse offers the perfect blend of classic charm and modern updates. Set on 2 acres and surrounded by open farmland, this spacious home features 4 bedrooms plus 2 bonus rooms, ideal for family, guests, or a home office. The sunny, south-facing kitchen offers peaceful views of the surrounding fields and a gentle stream--perfect for morning coffee or sunset dinners. With 2 large bathrooms featuring walk-in showers, there's plenty of room for comfort and convenience. Enjoy the outdoors from the covered porch, or take advantage of the woodshed and two-car garage for all your storage needs. Recent updates include a metal roof, vinyl siding, replacement windows, and modern interior finishes throughout--making this home truly move-in ready. Nestled on a quiet country road, every window in this home frames picturesque Vermont scenery. Whether you're looking for a full-time residence or a countryside getaway, this cozy and spacious farmhouse is a must-see! See Listing Details & 52 images.

Under Contract Chester VT Home for sale $260,000 $250 per sq.ft.

$260,000 $250 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1040  |  Acres: 4.12
Listed on Friday Feb 28, 2025
Description: Newly remodeled manufactured home with a full basement/foundation, nestled on 4.12 +/- private acres! This beautifully updated home boasts a modern kitchen featuring maple cabinets, a subway tile backsplash, a gas range with hood, and ample space for a dining table or kitchen island. Just off the kitchen, a laundry/pantry area offers plenty of storage for food and cleaning supplies. A unique dividing wall with tall windows separates the kitchen from the open-concept living area, adding a touch of modern design while maintaining a spacious feel. The primary suite includes its own full bathroom with a sliding barn door, while two additional bedrooms and another full bath are located on the opposite side of the home, ensuring privacy for all. The spray-foamed basement remains unfinished, housing all utilities and a previously existing full bathroom that could be restored if desired. Outside, a concrete slab with electricity remains where a two-car garage once stood, providing the perfect foundation to rebuild. All of this is tucked away behind woods and trees, yet conveniently located right off Rt. 10, with easy access to Chester and Springfield. See Listing Details & 26 images.

Under Contract Chester VT Home for sale $319,000 $118 per sq.ft.

$319,000 $118 per sq.ft. Chester VT Home »


Price Change! Reduced by $160,000 down 50% on March 11th 2025
4 Beds | 2 Baths |   Total Sq. Ft. 2702  |  Acres: 0.89
Listed on Wednesday May 8, 2024
Description: Fully furnished! Thoughtfully upgraded home on .89 acres located in the beautiful area of Gassetts in Chester, Vermont. Easy access to I-91, 10 minutes to Okemo, 20 minutes to Magic Mountain, 30 minutes to Bromley, 40 minutes to Killington and under an hour drive to Stratton ski resort. This three bedroom, two bathroom home has an open concept. Two bedrooms on the second floor and one bedroom on the third floor. One bedroom on the second floor is a primary bedroom with a full bathroom. Large open area kitchen and dining room with plenty of room for storage, cooking and entertaining. Recent upgrades to the home include a brand new roof, siding, all new flooring, new kitchen cabinets and quartz countertops, new sheetrock and paint throughout, new sub flooring in the living room, laundry area, and mudroom, new window sills, new mini split, removal of all previous knob and tube wiring, replaced windows, new french door in the living room, new patio and fire pit area, freshly leveled and graveled driveway, two-car carport, refinished front deck, and freshly leveled backyard. Hiking, mountain biking, and snowmobiling trails surround the town, making this home ideal for anyone who enjoys the natural beauty of Vermont. High speed internet is available (currently VTEL). See Listing Details & 26 images.

Under Contract Chester VT Home for sale $329,000 $113 per sq.ft.

$329,000 $113 per sq.ft. Chester VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2904  |  Acres: 0.25
Listed on Thursday Apr 3, 2025
Description: Imagine a home so inviting and comfortable, you'd never want to leave. Welcome to this practical and low-maintenance ranch-style home, perfectly designed for both relaxation and entertainment. Step inside and be greeted by the beautifully updated living room, bathed in natural light and warmed by a cozy wood stove--a haven during those chilly Vermont winters.This house isn't just a place to live; it's a space to thrive. The open concept kitchen and dining area, complete with a breakfast bar and ample cabinet space, serves as the heart of the home. Whether you're whipping up a family meal or hosting a casual brunch, this kitchen handles it all with ease.The practicality continues with three comfortable bedrooms on the main level alongside a full bathroom and primary ensuite. Venture downstairs to the fully finished basement, a dynamic space featuring an additional bedroom, a 1/2 bathroom, a media room, and a sizable office space currently set up as a gym.  There is so much space you imagination can run wild with ideas for new uses.Maintenance is a breeze both inside and out, letting you spend more time enjoying your home and less on upkeep. The yard is just as manageable, ideal for those who appreciate outdoor space without the hassle.This clean, streamlined home is ready for you to make it your own. Don't miss out on this charming, expansive ranch--call today to schedule your viewing and start imagining your life here, where every day feels like a retreat. See Listing Details & 29 images.

Under Contract Chester VT Home for sale $425,000 $144 per sq.ft.

$425,000 $144 per sq.ft. Chester VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2960  |  Acres: 0.7
Listed on Wednesday Dec 4, 2024
Description: The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer leads to the second floor which features 3 bedrooms, 2 baths and a sitting room. An addition added by the author and named the Queen's Room during the current owners bnb tenure features built-ins, a partition wall with transom window and a wood stove insert flanked by cozy built-in seats. The primary bath features gold-plated fixtures, a skylight and soaking tub. The first floor also has a heated, retail space for a home business with a separate entrance and office above that has served as an antique shop. The two-car attached, garage has unfinished, overhead space. The exterior needs some sprucing up and a new owner will want to add cosmetic upgrades. The property on .70 acres has a lovely yard with a hydrangea bush, charming bridge, small pond and stone bench overlooking the picturesque village. See Listing Details & 60 images.

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

4 Beds | 3 Baths |   Total Sq. Ft. 2868  |  Acres: 3.21
Listed on Monday Apr 21, 2025
Description: This charming multi-level home provides 4 bedrooms and a variety of places to find private space for quiet. Also a large open recreation room which includes a full size pool table/table tennis table and dry bar. Located just 3 miles from the charming Town of Chester. An easy drive to Bromley Mt, Magic Mt and Okemo, this makes a great home for an active family. Beautiful views from the deck provide a great place for morning coffee and an evening watching the stars. There is plenty of space for gardens and outdoor activities as well as wooded land to spend relaxing time in. House has automatic whole house propane generator. There are two firemen that live on the road, so it is always well plowed and maintained. See Listing Details & 44 images.

$469,000 $121 per sq.ft. Chester VT Home »

4 Beds | 5 Baths |   Total Sq. Ft. 3888  |  Acres: 0.53
Listed on Saturday Dec 14, 2024
Description: This spacious 1800's home is filled with Vermont charm and located in the heart of Chester. Filled with natural light from newly installed windows, the home boasts beautiful wood floors throughout and antique door handles that capture the essence of the era. Spacious bedrooms provide ample comfort, while smart thermostats ensure modern convenience. A newly built, covered front porch welcomes you into the home, and a deck off the kitchen leads to an open, level backyard--perfect for gardening or outdoor activities. One of the standout features of this property is the versatile studio space. Accessible via its own entrance from Main Street, this expansive area features vaulted ceilings and two half baths, offering endless possibilities. Whether you're looking to create a storefront, set up an at-home business, or convert the space into a private apartment, the potential is limitless. This property offers a unique opportunity to live in a quintessential Vermont town while having the flexibility to tailor the space to your needs. It's a must-see for anyone seeking a charming, functional home with potential for growth! See Listing Details & 53 images.

New Listing! Chester VT Home for sale $489,000 $375 per sq.ft.

$489,000 $375 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1304  |  Acres: 1
Listed on Saturday Apr 26, 2025
Description: Experience the warmth of history with the ease of modern living at 663 Depot Street. This fully renovated 3-bedroom, 2-bath home offers historic charm with today's updates. Since 2022, insulation, drywall, electrical, plumbing, HVAC, furnace, water heater, fixtures, countertops, cabinets, and appliances have all been replaced. The home's original wood flooring has been carefully refinished to honor its roots. Period-appropriate paint colors and thoughtful details like exposed beams and original woodwork add to the timeless feel. The attached 2-story post-and-beam barn--larger than the house--offers incredible potential to expand your living space or create a dream workshop. Set on 1 acre with a sprawling lawn, fire pit, and a prime location near Chester's Stone Village, Grist Mill, Smitty's Market, and more. Just 15 min to Okemo and the lakes, 30 min to Bromley, and under an hour to Killington, Stratton, and Mount Snow, it's ideal for year-round fun. Currently enjoyed as both a family getaway and a successful Airbnb, it offers strong income potential. Whether you're looking for a primary home or investment, this timeless property is not to be missed. See Listing Details & 44 images.

$500,000 $289 per sq.ft. Chester VT Home »


Price Change! Reduced by $175,000 down 35% on March 22nd 2025
4 Beds | 2 Baths |   Total Sq. Ft. 1728  |  Acres: 1.12
Listed on Friday Mar 1, 2024
Description: Looking for the perfect ready to move in home in Vermont? Look no further than this French Provincial meets Vermont cabin centrally located in the quiet town of Chester, Vermont on Route 103. Within an hour drive to 5+ great ski mountains, within 10 minutes to Okemo mountain. House features so many great amenities and improvements--new black/grey roof just installed June 2024, new egress windows, beautiful indoor and outdoor fireplace, outside hot tub, beautiful stone patio, large private deck, 2 car garage, 4 bedrooms (but lots of room for more people), 2 bathrooms, a bonus bunk room, 2 extra lofts for an office or library, extra recreation room, and paved driveway. The house is a short distance to several beautiful lakes and state parks, mountains to hike, near the VAST trails, and interstate 91. Very spacious and also currently a great short term rental income property. And if you happen to lose power there is a 20kw stand-by propane generator ready to go. Call for a showing today! See Listing Details & 44 images.

New Listing! Clarendon VT Home for sale $280,000 $267 per sq.ft.

$280,000 $267 per sq.ft. Clarendon VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1048  |  Acres: 0.37
Listed on Tuesday Apr 22, 2025
Description: Nestled in a fantastic North Clarendon neighborhood, this neat and inviting home offers comfortable living with appealing features both inside and out. You'll appreciate the charm of the hardwood floors that flow throughout the main living areas and into the three well-proportioned bedrooms. Situated towards the end of a peaceful dead-end street, a private back deck connects the house to the detached garage, offering extra storage or workspace. Outside, you'll find a big, flat backyard, perfect for outdoor activities, gardening, or simply enjoying the Vermont seasons. The recent addition of new siding enhances the home's curb appeal and provides added protection. This lovely residence presents a wonderful opportunity to embrace a desirable Vermont lifestyle in a sought-after location. See Listing Details & 17 images.

$289,900 $133 per sq.ft. Clarendon VT Home »


Price Change! Reduced by $83,100 down 29% on April 25th 2025
2 Beds | 2 Baths |   Total Sq. Ft. 2172  |  Acres: 0.71
Listed on Tuesday Jul 23, 2024
Description: Come see this newly renovated bilevel home that features 2 bedrooms and 2 full bathrooms on a 0.71 acre lot. The extensive updates include new kitchen cabinets, countertops and appliances. Both bathrooms have new tubs, showers, fixtures, vanities, sinks, faucets, and toilets. All new windows, interior and exterior doors, trim, heat registers, light fixtures. The entire home has been freshly painted in a gray scale and new laminate flooring throughout. The exterior updates include a new roof, soffit, fascia, siding, a new overhead garage door, and the driveway has been refreshed with new stone. A new furnace completes the extensive renovations. This property is in a rural location with a running stream out back but within a short distance to all that Rutland has to offer. See Listing Details & 40 images.

Under Contract Clarendon VT Home for sale $325,000 $171 per sq.ft.

$325,000 $171 per sq.ft. Clarendon VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1901  |  Acres: 1.3
Listed on Friday Mar 7, 2025
Description: Nestled on a spacious 1.3 acre lot, this three bedroom, 1 1/2 bath home offers a perfect blend of comfort, convenience, and natural beauty. Boasting mountain views, this property provides a serene retreat while remaining close to local amenities and outdoor activities. As you enter the home, you're greeted by a bright and inviting living area that is perfect for both relaxation and entertaining. The functional kitchen, complete with modern appliances and ample counter space, flows seamlessly into the dining area, offering space for family meals or dinner parties. The finished basement areas add incredible versatility to the home, offering additional living space that can be customized to suit your needs - whether it's a cozy family room, home office or recreation area. The home features three bedrooms with easy access to the full bathroom. An attached 3-car garage provides plenty of storage space for vehicles, tools, or outdoor gear, while the 1.3 acre lot offers room for gardening, play or future expansions. Mountain views provide a tranquil backdrop. Don't miss out on the chance to view this charming home! See Listing Details & 22 images.

Under Contract Clarendon VT Home for sale $399,900 $221 per sq.ft.

$399,900 $221 per sq.ft. Clarendon VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1806  |  Acres: 1.04
Listed on Wednesday Mar 5, 2025
Description: Location! Location! Location! Nestled in a serene country setting, this updated 3-bedroom 2-bath ranch, with an in-ground pool, offers the perfect retreat for a new home buyer eager to embrace Vermont living and life-style. Enjoy the tranquility of nature while being just minutes from downtown Rutland's work, shopping, entertainment and dining options. Situated less than 30 minutes between Killington/Pico and Okemo Ski Resorts, and 30 to 40 minutes to either Lake Saint Catherine or Bomoseen, outdoor enthusiasts will find skiing, biking, boating, fishing or hiking opportunities almost at their doorstep. Inside, the updated kitchen and baths, complemented by hardwood floors, modern appliances, and central air conditioning, creates a warm, comfortable and inviting atmosphere. There's additional comfort, security, and reliability in the whole house LP gas generator. The spacious 2 car garage and full basement offer ample space for cars, trucks, hobbies, extra storage, or future expansion. The home's maintenance-free vinyl siding and windows ensure easy upkeep, allowing more time to relax by the in-ground pool, gardening, or simply soak in the picturesque mountain views. Here is your opportunity to embrace a lifestyle where convenience meets serenity in this tastefully appointed home, surrounded by Vermont's natural beauty, located only minutes from all the places you care to be. Check out the 3D video provided with this listing information. Call for an appointment. A must see See Listing Details & 46 images. Includes a Virtual Tour

$415,000 $159 per sq.ft. Clarendon VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2614  |  Acres: 3.7
Listed on Thursday Apr 17, 2025
Description: Nestled on over 3 acres, this beautifully maintained 3-bedroom, 2-bathroom raised ranch offers the perfect blend of comfort, functionality, and natural beauty. Step out onto either the front or rear deck to take in the dramatic mountain views, ideal for morning coffee or evening sunsets. Inside, the main level features an open floor plan between the updated custom eat-in kitchen, the large living room and the dining room. The entire space is bright, inviting and spacious for a large or growing family. Downstairs, the finished walkout lower level includes a fully equipped in-law apartment perfect for extended family, guests, or potential rental income. Outside, a detached two-story, 2-car garage provides abundant storage or workshop space. The property is a nature lover's dream, with a large, picturesque distributary of the Otter Creek meandering through the landscape makes this area ideal for wading, wildlife watching, or simply relaxing to the sounds of flowing water. Whether you're seeking a year-round residence, a multigenerational home, or a peaceful retreat, this property delivers on privacy, views, and versatility. Welcome home! See Listing Details & 57 images.

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