$749,900 $259 per sq.ft. Castleton VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2890  |  Acres: 0.9
Listed on Tuesday Nov 25, 2025
Description: Discover this charming 3-bedroom, 3-bathroom home overlooking beautiful Lake Bomoseen, complete with deeded lake access, two docks, and a deck with space for a grill--perfect for waterfront dining and relaxation. Enjoy summer boating and winter recreation, including ice skating, ice fishing, cross-country skiing, and snowshoeing right on the lake. The remodeled kitchen opens to a bright dining area, which flows into a sunken living room featuring a cozy wood-burning stove for chilly evenings. The first floor also includes an office, a ¾ bath, and a convenient laundry area. Upstairs, you'll find three bedrooms, including a primary suite with stunning lake views and direct access to the full bathroom, which is shared with the additional two bedrooms. A spacious bonus room with its own full bathroom completes the second floor--ideal for a playroom, guest suite, hobby room, or flexible living space. Outside, enjoy a large deck perfect for entertaining, a relaxing hot tub, a generous yard, and a peaceful, private setting. A 3-bay garage provides ample room for parking, storage, and all your recreational toys. Since 2020, the owners have completed numerous updates, including a fully remodeled kitchen, new garage doors, a new roof with skylights, fresh exterior paint, and many additional cosmetic improvements throughout. See Listing Details & 52 images.

Under Contract Village of Proctorsville in Town of Cavendish VT Home for sale $289,000 $235 per sq.ft.

$289,000 $235 per sq.ft. Village of Proctorsville in Town of Cavendish VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1232  |  Acres: 0.26
Listed on Thursday Jul 10, 2025
Description: This property must be seen in person to be appreciated. Very clean and move-in ready Vermont 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on .26± acres features a new roof and combines comfort and convenience in one of the most desirable areas of the Okemo Valley. Enjoy a spacious living room and bright eat-in kitchen with breakfast nook, and a wonderful enclosed breezeway--the perfect spot to relax or entertain in 3 seasons. The living room offers generous space with picture windows creating plenty of light. The second floor spacious, primary bedroom is equipped with many outlets for charging devices. Two additional bedrooms and a 3/4 bath complete the second floor. House re-built in 70's. The two-car attached garage provides workshop and storage space off the paved driveway. A very neat, clean and dry basement with up newer oil tank, Thermopride furnace and bulkhead doors that open to the breezeway. Enjoy mountain views and a deep yard with space for gardening and winter fun tubing or sledding. Walk to Proctorsville Village for local dining, Singleton's General Store, or the elementary school. Whether you're hitting the slopes at Okemo, golfing at Fox Run Golf Course, or simply enjoying Vermont's four-season beauty, this is rare opportunity to own an affordable home in one of Southern Vermont's most popular destinations. Motivated sellers encouraging offers. See Listing Details & 34 images. Includes a Virtual Tour

$650,000 $195 per sq.ft. Cavendish VT Home »

Waterfront on Pond _Unnamed
3 Beds | 4 Baths |   Total Sq. Ft. 3336  |  Acres: 13.4
Listed on Sunday Apr 12, 2026
Description: Beautiful Cape-style home set in picturesque Cavendish, Vermont, offering a seamless blend of modern design and Craftsman-quality finishes. This thoughtfully designed home features a striking dual fireplace and a unique dual-access kitchen with counters on both sides--ideal for entertaining. The kitchen is equipped with stainless steel appliances, including a gas stove, perfect for the home chef. Set on a property that borders a budding state forest, this home offers privacy and direct access to nature. Enjoy your own private pond, ideal for fishing, swimming, or simply relaxing in a serene setting. Whether you're looking for a full-time residence or the perfect Vermont getaway, this property delivers. Conveniently located in the heart of ski country, with easy access to Okemo Mountain and a short drive to scenic river views, this location is a dream for outdoor enthusiasts year-round. A rare opportunity to own a property that combines comfort, craftsmanship, and the best of Vermont living See Listing Details & 50 images. Includes a Virtual Tour

$795,000 $374 per sq.ft. Cavendish VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2128  |  Acres: 19.06
Listed on Monday Oct 27, 2025
Description: Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral ceiling. Enjoy the warmth of the all-natural wood surroundings while sitting beside the cozy fire from the wood burning stove. There are 3 large bedrooms and 2 1/2 baths. The floors are nicely finished hard and soft wood, with slate tiled floors in the entryway and kitchen. SNOWMOBILE ENTHUSIASTS! The VAST trail is right here, so hop on your sled from your house and go! See Listing Details & 41 images.

$219,000 $174 per sq.ft. Chelsea VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1256  |  Acres: 0.32
Listed on Monday Mar 23, 2026
Description: Step into timeless New England charm with this classic farmhouse rich in character. Beautiful wide pine floors, beam ceilings, and a cozy wood stove that creates the perfect gathering space on crisp days. Offering four bedrooms, one full and one half bath, there's plenty of room for family, guests, or flexible living arrangements. The inviting covered front porch is ideal for morning coffee or unwinding at the end of the day. Outside, the property continues with a three-stall barn complete with a hayloft--perfect for animals, hobbies, or storage. Full of warmth, charm, and opportunity, this is a property where you can truly feel at home. See Listing Details & 31 images.

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

3 Beds | 1 Baths |   Total Sq. Ft. 1327  |  Acres: 0.13
Listed on Wednesday Jun 18, 2025
Description: Don't miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer, which is a great space to store the skis, poles and helmets from a great day of skiing. The main level features a generous living room anchored by a classic wood-burning fireplace ideal for cozy winter evenings. The sunny eat-in kitchen provides ample space for meals and gatherings, while the full bath with laundry adds everyday practicality. All windows were replaced in 2019, offering energy efficiency and bright natural light throughout. Upstairs, you'll find three spacious bedrooms, including a stunning turret space that creates a bright and airy nook perfect for reading or relaxing under the sun-drenched windows. The original woodwork and architectural details throughout highlight the craftsmanship of a bygone era. Outside, the covered wrap-around porch invites you to unwind and enjoy the peaceful sounds of the nearby babbling brook. Take a short stroll to the local market or explore the picturesque village with its shops, restaurants, and small-town charm. This home is more than just a place to stay it's a place to create lasting memories. All only 15 miles from Okemo Mountain! See Listing Details & 26 images.

Under Contract Chester VT Home for sale $269,000 $230 per sq.ft.

$269,000 $230 per sq.ft. Chester VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1168  |  Acres: 0.5
Listed on Monday Apr 6, 2026
Description: This cozy gambrel style home tucked away on a nice level 1/2-acre lot just on the outskirts of Chester village offers lots of yard space, lots of storage space and is an easy keeper. This cute home offers hardwood floors on the first floor, has lots of natural light, an enclosed porch that could work as a home office, dining area, mud room or just a place to hang out. 2nd floor features three bedrooms with the primary leading out to a deck overlooking the yard. Nice high ceilings on the second floor make the rooms very open and bright. There's an attached storage room allowing room for freezers, storage or a second mud/entry room. Large 2 bay garage with second floor storage, a side shed that would be perfect for a garden shed and a separate space for lawn and snow blowers. The owners have done lots of upgrades, including a full house generator. So, if you are looking, be sure to add this home to your list. See Listing Details & 34 images.

Under Contract Chester VT Home for sale $340,000 $162 per sq.ft.

$340,000 $162 per sq.ft. Chester VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 2096  |  Acres: 1.69
Listed on Friday Mar 20, 2026
Description: Welcome to a charming village retreat in the heart of Chester, perfectly situated on Main Street in the historic Chester Stone Village. This inviting home blends classic Vermont character with comfortable, year-round living. Enter through a practical mudroom with ample space for all your seasonal gear--ideal for embracing Vermont's four-season lifestyle. To the right, at the front of the home, you'll find a bright and open living space featuring a spacious kitchen with a large island, seamlessly connected to the dining area and living room. A glass door leads to a covered porch, creating the perfect spot for morning coffee or relaxing evenings. The main level also offers a dedicated office, a full bathroom, and a convenient laundry room. Toward the back of the home, two bedrooms provide comfortable accommodations, and a stunning family room showcases vaulted ceilings, exposed beams, and walls of windows that fill the space with natural light. A glass slider opens to the back deck, where you'll find an above-ground pool--perfect for summer enjoyment. Experience the charm of Vermont living in this village home, just moments from local shops, dining, and all that Chester has to offer. Visit the Okemo real estate community today. Taxes are based on town assessment. See Listing Details & 55 images.

$349,000 $235 per sq.ft. Chester VT Home »


Price Change! Reduced by $50,000 down 14% on March 19th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1488  |  Acres: 0.25
Listed on Saturday Sep 13, 2025
Description: Welcome to your dream home - This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the gorgeous hardwood floors that add warmth and character to every room. Bask in the great natural light that fills every corner of this lovely abode, making every day feel bright and inviting. This home includes a main level bedroom, dining room and family room. In addition there is an attached garage and a barn for all your hobbies. This home is perfect for families and outdoor enthusiasts alike. Imagine being just a short stroll away from the village store for all your essentials and enjoying nearby skiing adventures in winter, along with shopping and restaurants year-round! Don't miss out on this incredible opportunity to own a piece of paradise in the heart of it all! Schedule your visit today and get ready to fall in love - your perfect home awaits! See Listing Details & 29 images.

Under Contract Chester VT Home for sale $359,900 $224 per sq.ft.

$359,900 $224 per sq.ft. Chester VT Home »


Price Change! Reduced by $65,100 down 18% on March 19th 2026
3 Beds | 1 Baths |   Total Sq. Ft. 1608  |  Acres: 0.25
Listed on Wednesday Nov 26, 2025
Description: Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area -- a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you'll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potential for additional living space, a workshop, or studio. Outside, enjoy your private fenced backyard with garden space, a fire pit, and even a bar area -- perfect for entertaining family and friends. This inviting village home combines charm, functionality, and opportunity -- come experience all that Chester has to offer! Visit the Okemo real estate community today. Taxes are based on current town assessment. See Listing Details & 53 images.

New Listing! Chester VT Home for sale $390,000 $299 per sq.ft.

$390,000 $299 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1304  |  Acres: 1
Listed on Thursday Apr 30, 2026
Description: Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that's hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester's Stone Village, the Grist Mill, and Smitty's Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals. See Listing Details & 51 images.

$399,000 $223 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1788  |  Acres: 3.3
Listed on Wednesday Jan 14, 2026
Description: Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for--flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below--perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there's room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery--rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont's natural beauty. A property that offers privacy, water frontage, land, and mountain access--without giving up convenience. See Listing Details & 31 images.

New Listing! Chester VT Home for sale $499,000 $378 per sq.ft.

$499,000 $378 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1320  |  Acres: 10.86
Listed on Thursday Apr 23, 2026
Description: Welcome to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, yet close to skiing, VAST and amenities. So many updates in the past two years, modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is a true move in ready beauty. The owners are leaving this home furnished, making this a true turnkey property. The rooms are nicely sized and in close proximity to bathrooms. This has been used as a vacation property and has a history of successful Airbnb. The wood burning fireplace brings a feeling of serenity on those chilly days. Fiber internet on site for those that work remotely. Town records state two bedrooms, however, the loft area has a sleeping quarter with a bathroom! Plenty of storage, full walkout basement gives ample space. This is one of those properties you won't want to miss on your home buying adventure! Truly a stunning property with so much to offer! See Listing Details & 60 images.

$595,000 $201 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2966  |  Acres: 3.08
Listed on Monday Apr 20, 2026
Description: Tucked away at the end of a quiet lane on three scenic acres, this well-maintained home offers a rare blend of privacy, versatility, and proximity to town. Set against the backdrop of the Williams River, the property delivers a peaceful setting with year-round interest: mature apple trees, open lawn, and seasonal views best enjoyed from the expansive back deck. Inside, over 2,500 square feet of living space is designed to adapt to a variety of needs. The vaulted-ceiling living area is filled with natural light from custom windows and anchored by a wood-burning stove, creating a warm and inviting central gathering space. Sliding doors connect seamlessly to the outdoors, making indoor-outdoor living effortless. The spacious kitchen features a generous pantry and flexible dining area with picturesque views of the property. The main level also includes a mudroom entry, laundry, a bedroom, and a three-quarter bath, ideal for single-level living, guest space, or a private office setup. Upstairs, additional bedrooms and a full bath provide comfortable separation of space, including a large primary bedroom. The finished lower level expands the home's functionality with a rec or media room, ample storage, and a walkout room well-suited for a workspace, studio, or fitness area. A two-car garage with breezeway access adds convenience, while the partially finished upper level offers even more potential for creative or practical use. A unique opportunity to enjoy a tranquil setting with flexible spaces to live, work, and unwind, just minutes from the heart of Chester. See Listing Details & 53 images.

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

3 Beds | 2 Baths |   Total Sq. Ft. 2205  |  Acres: 1.71
Listed on Thursday Jan 15, 2026
Description: Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the day sunlight. A bedroom and 3/4 bath round out the main floor. Upstairs you'll find two large bedrooms and a full bath. All good homes should have a family room and this doesn't disappoint. The lower walk out had a cozy spot with a large sectional to watch movies and is perfect for "hanging out" with friends. There is a work out area and a bonus room located on the lower level. This is definitely more than a ski home as there is plenty of outside living space. There is a shady front porch with begs for a rocking chair and a good book. Sun seekers will enjoy the rear deck which faces west and gets plenty of sunshine. Perennial gardens abound and offer color and character all summer long. There is a garage barn that can be used in a myriad of ways... park a car, use the workshop, store your toys... There is also an upstairs mostly finished room that can be your blank canvas. Visit the Okemo real estate community today. Taxes are based on current town assessment. See Listing Details & 60 images.

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