302 properties for sale in Jacksonville village, Whitingham town Windham County Vermont

Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and whimsical and yes it gets even better-this is waterfront property that offers substantial frontage on the North Branch of the Deerfield River, a haven for fly fishing and serenity. For the farmer in you, two livestock barns provide ample space for your animals or envision more-the potential to be certified organic or transform these barns into charming event spaces or the farm into a Bed and Breakfast to blend Vermont's rural allure with modern comfort. This property is an opportunity waiting to be realized. With 5 identified potential new home sites, you may consider creating a family compound or

Beautiful 4 bedroom, 3.5 bath townhouse just off the Hermitage Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club Ski Area and Mount Snow. The deck overlooks the 10th green and is beyond typical driving distance, so you can enjoy the sun while watching play. This unit has been updated including new carpet, new high efficiency wood stove in the stone hearth, gorgeous adirondack furnishings and fixtures, updated appliances throughout, a large dining area, mudroom, master suite with bright upgraded bath, additional guest suite, 2 guest rooms with a shared bath, and plenty of space to stretch your legs all 4 seasons. There is a large back deck for outdoor entertainment, covered front porch to escape the weather, and amenities including snow removal, landscaping, building maintenance, and trash. There is an ongoing project to replace windows and siding that will ultimately improve the overall exterior aesthetic. Easy access to and fr

Located just minutes from the slopes of Mount Snow, the pristine waters of Lake Raponda, and the expansive Harriman Reservoir, this property offers the ideal combination of convenience, recreation, and opportunity. With ample space and zoning flexibility, you have the unique chance to build an Accessory Dwelling Unit (ADU) on-site, perfect for generating rental income, hosting guests, or creating a private retreat. Whether you're a winter sports enthusiast, a lover of water activities like kayaking, paddleboarding, and fishing, or simply seeking a peaceful escape, this location is a gateway to year-round adventure. Explore skiing and snowboarding, hike and bike scenic trails, or enjoy the vibrant local food and arts scene in nearby downtown Wilmington. Imagine the possibilities: your dream home, an income-producing property, or a combination of both, all in a setting that perfectly captures the beauty and charm of Vermont

A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At the heart of the home is a chef's kitchen complete with marble countertops, an oversized center island, walk-in pantry, dual Sub-Zero wine refrigerators, a built-in pizza oven, and a impressive suite of Wolf and Sub-Zero appliances. Designed for year-round enjoyment, the grounds are simply unmatched. Bluestone patios surround the home and lead to a sunken hot tub, cold plunge, a massive BBQ, pergola, children's playscape, and a spectacular post-and-beam open-air pavilion. Gather around the oversized fire pit while enjoying panoramic western sunsets over Haystack Mountain. Private tennis and pick

AS-IS* Classic Chalet Near Mount Snow! Opportunity awaits with this classic chalet, ideally located just minutes from Mount Snow, The Hermitage Club, and the shops and restaurants of downtown Wilmington. Tucked among the trees, this charming retreat offers a peaceful setting with a spacious deck perfect for relaxing or entertaining. Inside, you'll find three bedrooms, one full bath, and nostalgic retro details that add to the home's vintage character. The property has remained in the same family for many years but has been unoccupied for over five years. The home is being sold *as is*. A pre-listing inspection has been completed and is available to help buyers better understand the property's condition and systems. Because the home has not been in use, the sellers have limited knowledge regarding the current functionality of the home's systems. Whether you're looking for a renovation project, a vacation getaway, or an investment opportunity in a desirable four-season location, close to

The Stable Lodge was built in 1969-1970. Located near Haystack Ski Area, The Golf Course and The Hermitage Club close to the Coldbrook. Built as a post and beam home. Features 1 acre with ample parking. Building will need an extensive rehab. Not safe to go into the structure

Outstanding contemporary farmhouse set on 5.3 acres of private, level acres, offering the perfect blend of comfort, space, and functionality. This well-maintained home features an open-concept first floor with a spacious great room highlighted by a cathedral ceiling and beautiful views. The main level also includes a bedroom and full bath, along with a convenient mudroom and laundry room. The custom maple cabinet kitchen boasts updated countertops and newer flooring runs throughout the home.The home's efficient Buderus boiler provides five heating zones for year-round comfort. The unfinished basement has separate rooms for potential finishing, along with a workspace for the handy or craft person. The oversized 30x30 two-car garage with loft provides exceptional storage space. A covered wraparound porch offers the perfect place to relax and enjoy the peaceful surroundings. Conveniently located near a local park with a ballfield and playground, and a short drive to wonderful Vermont skii

Approximately 10 years new, this well-maintained and recently refreshed home offers the perfect combination of modern construction and country charm in the Green Mountains. Set on 2.0+/- acres in Searsburg, Vermont, a one-lane dirt road separates you from thousands of acres of National Forest land to explore literally right outside your door. The lot offers plenty of mature plantings, a stonewall border, manageable yard and garden space, multiple outbuildings, and an adorable bonus cottage. Enter the main house through the screened-in porch, an excellent spot for morning coffee. Soak in the hot tub on the private back deck with your evening cocktail! Inside, find 1,302 square feet of living space with 2 bedrooms, 1.5 baths, open kitchen/dining/living with breakfast bar, coffee bar, and plenty of counter space. Offered mostly furnished, it is ready to enjoy from day one. Low-maintenance vinyl siding, architectural shingle roof, and gravel driveway. The property includes three versatile

Nestled in the woods at the end of a quiet road on 5 acres with picturesque hillside views overlooking Berkshire East Resort, this attractive post-and-beam home makes for the perfect year round escape. Beautiful stone patios create exceptional outdoor living spaces for relaxing, entertaining, or simply enjoying the natural surroundings. Inside, massive exposed beams, cathedral ceilings, warm wood floors, and an attractive fireplace create a welcoming and warm atmosphere. The custom kitchen is a cook's dream, featuring granite countertops, abundant workspace, propane heat stove, and an open layout flowing into the dining area and living room. The first floor also offers a bedroom, full bath, and flexible office or sitting room. Upstairs are two spacious bedrooms and another full bath. The walkout basement includes a finished hobby/exercise room, laundry, Viessmann boiler, and plumbing for a future bath. Min. Berkshire East, Shelburne Falls, the Berkshires - four seasons of adventure!

Welcome to The Roost! This charming Charlemont cottage offers the perfect blend of modern updates and cozy cabin living. Completely rebuilt in 2022, this home is move-in ready with cathedral knotty pine ceilings throughout,thoughtful design, and everything you need for a low maintenance retreat. Whether you're looking for a weekend getaway, vacation home, Airbnb opportunity, or a comfortable downsizing option, this property is ready to enjoy.Set along peaceful Pelham Brook, this property offers private brook access, beautiful water views, and the relaxing sounds of nature right outside your door. The spacious yard provides plenty of room for outdoor enjoyment and features established blueberry bushes, a large storage shed, and a private setting to unwind.Conveniently located just minutes from the scenic Deerfield River, Berkshire East Mountain Resort, Thunder Mountain Bike Park, and the many outdoor recreational opportunities Charlemont has to offer! Your dream getaway awaits, schedule

Breathtaking Lake and Vermont Forever Wild views from this 10 acre parcel overlooking Lake Whitingham, with deeded lake access. The premiere Old Mill Lane development is host to some of Wilmington's finest homes thanks to large private parcels, extended driveways, exclusive shared lake access and beach area with kayak rack, swimming cove, and easy access to the Village of Wilmington and nearby ski areas of Mount Snow and the Hermitage Club. This 2005 home sits on 10+ acres with tremendous exposure and a serene lake setting. This was a custom architect designed build which is being offered by the original owners. The home features a large open living space with high ceilings and custom mill work throughout, gorgeous wood floors and extensive wide wood moldings, a spacious area which leads to the large screened porch, chefs kitchen with breakfast bar and stainless appliances, all with breathtaking lake and sunset views. There is a main floor guest suite with gorgeous bath and walkin clos

Escape to this charming country home offering the perfect blend of comfort, character, and outdoor living. Surrounded by woods and hillside views, you'll enjoy beautiful gardens, inviting sitting areas, a relaxing wraparound porch, and a spacious deck. Inside, the warm wood interior creates a cozy lodge-like atmosphere. The open kitchen flows into the living room, highlighted by a cathedral ceiling, handsome stone facade chimney, loft, skylights, and abundant windows that fill the home with natural light and showcase the surrounding scenery. The main level also features a bedroom and a renovated full bath. The finished walkout lower level is ideal for guests, offering a spacious family room with a wood stove, an additional bedroom, a renovated full bath with laundry. A one-car garage and brand-new heating system complete the package. Ideally located just 5 minutes from Berkshire East Resort and the Deerfield River, 10 minutes to Shelburne Falls, and only 30 minutes to the Berkshires

NEW LOG HOME LISTING ON 5+ ACRES WITH BARN AND GARAGE! OPEN HOUSE MONDAY, MAY 25th, 11am to 1pm This true log home offers 3 beds and 2 baths, a garage, and barns in a setting designed for year-round enjoyment. Offering just over five acres with open fields, meadows, mature gardens, stone walls and stone gardens, perennial plantings, outbuildings, and charm! Inside, hardwood and tile floors, high ceilings, stylish updates, and natural wood finishes create a warm, comfortable, and functional living environment. The kitchen features maple cabinetry, granite countertops, stainless steel appliances, a pretty view of the back yard, and an open-concept layout flowing into a spacious dining area. A wood-burning stove serves as a focal point in the living room, while a mudroom and full unfinished basement adds everyday convenience. Enjoy the covered front porch or additional outdoor dining and gathering space on the deck. Outside, the property includes rock gardens, specimen trees, perennial ga

This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by the current owners, and features a lodge style quite unique in the area which offers warm charm and Vermont rustic styling perfect for a retreat. Inside you are treated to vaulted ceilings in the main living room with floor to ceiling stone fireplace. There are freshly painted walls and exposed woodwork throughout, a country kitchen with gas stove and basin vintage sink, great light from the many windows and updated lighting, a tremendous great room addition perfect for entertaining with wood stove for ambiance, two main floor suites including a large primary, an upstairs guest suite, a spacious

Roll up your sleeves! This property needs complete rehab but will be well worth the effort. Private location set back from the road, large yard ready to enjoy. Short drive to North Adams for shopping. Don't hesitate to take a look this may be the one for you

Rustic Hunting Cabin on 1+/- Acres. Several sleeping areas including a loft. One full bathroom. Kitchen with stove,,microwave, refrigerator, stove, pellet stove, wood stove, 2 mini splits, washer and dryer. Plan your weekend runaway now!

Enjoy Green Mountain views from this bright and spacious end-unit townhouse, perfectly sited on the 1st fairway at the Haystack Golf Course. An oversized deck invites outdoor dining and entertaining, with sunsets over Haystack Mountain as your backdrop. Inside, natural light pours through windows and skylights into the open floor plan featuring vaulted ceilings, a fieldstone wood-burning fireplace, and updated main-level flooring. The kitchen offers a breakfast bar and gas range, while the dining area flows seamlessly into the living space. Upstairs, the open loft bedroom includes a private updated bath with oversized shower. The lower level provides a generous primary suite with jetted tub, two additional bedrooms, full hall bath, and laundry area. A covered porch entry with mudroom keeps golf and ski gear organized. The association handles exterior maintenance, landscaping, snow removal, and even delivers firewood to your door for true ease of ownership. Located just steps from golf,

Presenting 144 Branch Hill Rd, Heath, MA - a rural ranch-style single-family residence built in 1988, offering approximately 1,832 square feet of living area on a scenic lot in the Hilltown community of Heath. The property features a functional layout, including a G-shaped kitchen with peninsula seating, vaulted/cathedral ceilings in the living room, and a bedroom with a walk-in closet. The home requires some repairs and updates and is being sold strictly AS IS. Buyers should perform their own due diligence regarding all systems and condition issues, including the well and septic systems. A Title V inspection has been completed and has received a Conditional Pass. Bonus, property has newer roof and new windows. This property presents an excellent opportunity for investors, contractors, or buyers seeking a renovation project in a private country setting with potential for sweat equity

Beautifully updated Country Club Village townhome overlooking the golf course! This move-in-ready property features a remodeled kitchen with granite countertops, stainless steel appliances, and an open-concept kitchen and dining area that's perfect for entertaining. All bathrooms have been tastefully renovated, and new flooring throughout gives the home a fresh, modern feel. Additional upgrades include a new furnace and hot water heater for added comfort and efficiency. The spacious loft provides flexible living space for guests, a home office, or a family room. Step outside to the back deck and enjoy peaceful golf course surroundings and seasonal winter views. Conveniently located near Mount Snow, The Hermitage Club, restaurants, shopping, and year-round recreational activities, this is an exceptional opportunity to enjoy Vermont living at its best

Set on 23 private acres with more than 2,000 feet of Green River frontage, this rare western Massachusetts retreat feels a world away yet sits minutes from downtown Greenfield. Follow your own drive to a crisp, modern home where maple floors run beneath soaring, vaulted shiplapped ceilings and walls of windows pull the surrounding woods inside. The open kitchen anchors a wide, light-filled main living space with a generous island, apron-front sink and custom cabinetry, opening to an airy, beam-lined great room with a linear fireplace and French doors to the outdoors. Custom built-ins, a spacious primary and clean, current baths complete the interiors. Outside, a fenced in-ground pool, private river beaches, and trails for hiking and four-wheeling stretch across land alive with eagles and deer. Room to fish, camp, swim and roam, all your own. Rooftop solar and gas heat keep it efficient and comfortable year-round. Wide open space, river and refined modern comfort, together at last

Your wait is over-an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach and boat rights to the lake. Set in a peaceful, nature-filled setting, this property is ready for your vision. The existing cottage requires significant foundation repair or replacement, presenting the perfect chance to restore the structure or start fresh and build your dream mountain lake retreat. A rare opportunity for investors, builders, or buyers looking to create something special in a truly desirable Vermont location. Being sold As-Is. This is a cash-only sale

A truly beautiful home offering a winning combination of original charm and character paired with thoughtful updates and additions. The first floor now offers a gorgeous kitchen open to the family room with lovely stone fireplace, formal dining room with beamed ceiling and wainscoting, and formal living room with another fireplace and original bow window. The living areas all feature beautiful wood floors and open through french doors to the huge screened porch, a space to enjoy. Also on the first floor are an office/den, which could serve as a first floor bedroom, a three quarter bath and laundry. The second floor was redesigned to incorporate a wonderful main bedroom suite, with bath and walk-in closet. There are three additional bedrooms and a third bath. Attached to the house are a bonus room, 2 car garage and storage shed. The 2 park-like acres feature beautiful gardens, flowering trees, stonewalls and frontage on Hinsdale Brook. A very special property in a wonderful location

Thoughtfully maintained 4-bedroom, 2-bath Chimney Hill chalet offering a warm, inviting feel with natural wood finishes, open-concept design, woodstove and features that capture the essence of Vermont living. The main living areas are bright, comfortable and welcoming, with easy flow to a deck overlooking surrounding mountain ridgelinesan ideal setting for both quiet mornings and relaxed entertaining. The home is designed for comfort and ease, featuring an oversized mudroom entry, full laundry area, and a layout that accommodates both everyday living and extended stays, of extended groups! A lower-level family room and additional overflow sleeping space provide flexibility for hosting and creating room for everyone without sacrificing privacy. Outdoor features include a fire pit area, large storage shed for recreational gear, and ample parking for vehicles, boats, or snowmobiles-making it easy to enjoy everything the area has to offer in every season. Located within the desirable Chimn

This is a farmhouse that is currently under construction. Selling as is, with the remaining materials included. It is off grid and was lived in up until last year. Construction started in November 2025. Large barn that used to be a dairy farm. House has 3 woodstoves for heat. 10 cords of wood are included. Very nice setting along side a beautiful brook. 16.5 acres of open and wooded land that is mostly level. The adjacent property of 279 acres is also listed by the owner. Call for pricing to purchase both. Blueprint and house plans are attached to show what the home would look like finished

Six oversized garage bays across two multi-level outbuildings, direct access to Green Mountain National Forest, backyard waterfalls, and 5.4 private acres make this gated Southern Vermont retreat unlike anything else near Wilmington. Just five miles from downtown Wilmington and less than 12 miles from Mount Snow, the property combines substantial space for living and entertaining with exceptional room for vehicles, boats, equipment, collections, creative pursuits, and outdoor recreation. The multi-level outbuildings expand the possibilities well beyond vehicle storage, with flexible finished and unfinished areas suitable for recreation, hobbies, collections, equipment, workshop use, or additional gathering space. Inside, post-and-beam warmth, hardwood floors, neutral finishes, a spacious kitchen with a large center island, updated baths with custom tile, and two oversized stone fireplaces create an inviting Vermont atmosphere. A private primary suite wing offers a well-appointed bath,