Properties Near 195 Stimpson Hill Road Whitingham, VT

Welcome to Bailey Hill Road in Readsboro, Vermont. This farmhouse architecture style home with wood siding has 2400 square feet of finished living space. The interior features warm wood accents throughout, including exposed beams, wide plank and oak floors, and even a stained glass window created by a Vermont artisan. This home sits on a beautiful, private parcel of land that offers plenty of room to explore, garden, or simply soak in the peace and quiet of Vermont countryside. The kitchen flows into a light-filled dining area, while the expansive living spaces provide endless flexibility for gathering, hobbies, or a home office. The sunroom takes advantage of the home’s southern exposure, a wonderful place to keep houseplants or to sit and enjoy the surrounding nature. It’s common to see a wildlife in this rural setting. Upstairs, you’ll find additional bedrooms and bonus rooms, perfect for family, guests or creating your ideal retreat. A full, unfinished basement offers abundant storage or potential to expand, while outside you’ll appreciate the large three-bay detached garage/barn ideal for vehicles, equipment, or a workshop. Geothermal heating. Large outdoor generator. This property is perfectly positioned for four-season enjoyment. Whether you’re seeking an outdoor lifestyle or easy access to recreation, you’ll love being just a short drive from ski areas, hiking trails, and the Massachusetts border. A true Vermont getaway with the space and setting to make it your own.

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 gardens, open land, and multiple outbuildings. The primary barn offers large box stalls, a tack room, and attached equipment storage, while an additional barn provides added utility and flexibility. An oversized two-car garage includes workshop space and a second-story area suitable for storage, hobby use, or workspace needs. Suitable for a variety of uses, including hobby farming, animal use, home business, recreational enjoyment, and primary or second-home ownership. Located in Southern Vermont with convenient access to lakes, skiing, hiking, snowmobiling, and four-season recreation.

OPEN HOUSE SUNDAY, MAY 17th, 11AM to 1PM Set on 3 peaceful acres near Lake Whitingham and Lake Sadawga, this spacious 4+ bedroom, 2.5 bath Colonial-style home offers a comfortable and versatile floor plan with room for everyone. Pull into your attached 2-car garage and enter through the mudroom with closets and storage for gear, or enter through the front formal entrance looking into the main living areas with high ceilings, wood floors, and great natural light.The comfortable living room with a wood stove flows into the open kitchen, which features a great workspace and a breakfast bar. The dining area accesses the new back deck overlooking the manicured lawn. Catch a glimpse of Harriman Reservoir from the deck and watch epic sunsets to the west over the lake and mountains. The family room for informal fun or media space is also located on the first floor.The second floor offers generously sized bedrooms, including a spacious primary suite with a full bath, along with three additional bedrooms and a 2nd large shared bathroom with double sinks. Laundry is conveniently located on the same level as the bedrooms for added everyday ease.The third floor adds even more flexibility with a bonus sleeping room and expansive overflow space ideal for recreation, office use, home gym, media room, hobbies, guests, or additional hangout space, depending on your needs.Outside, enjoy mature perennial gardens, stone walls, and usable lawn space in a peaceful setting on a paved dead-end road shared by only a few homes. A 1-year-old above-ground pool is included in the sale, a perfect summer setup to complement Vermont’s warm-weather season with boating ( boat launch just down the road), swimming, hiking, and recreation around lakes just moments away. Space, location, acreage, ample bedrooms and baths, garage, and well-maintained…don’t miss it!

Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's craftsmanship. The open living and dining area features a brick fireplace with woodstove insert, creating a warm and welcoming setting on cold winter nights. The second floor offers five bedrooms, two baths, a cozy den, and a tucked-away upper-level retreat—ideal for reading, writing, or quiet reflection. Set on 12.80 acres, the land offers endless possibilities, ideal for a hobby farm, pastures for horses or cows, or growing your own vegetables. A vintage barn and storage shed, ready for restoration, adds to the property’s timeless rural appeal.

Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level, where you’ll find three restful bedrooms and a spacious bathroom featuring a jetted tub, tiled floors, and a glass-enclosed shower—perfect for unwinding after a day in the mountains. Head upstairs to the main level and enjoy the wide-open floor plan, where the kitchen, dining area, and living room flow together seamlessly. A cozy wood burning fireplace anchors the space, while a door opens to a sunny deck ideal for morning coffee, evening gatherings, or simply soaking in the peaceful surroundings. This turnkey home is fully furnished and ready for you to move right in. Whether you’re here for adventure or relaxation, the location offers it all—ski or hike at Mount Snow or Berkshire East, explore the VAST snowmobile trails, golf at Haystack or Mount Snow, or take in the dining and cultural scene of the Berkshires, all just minutes away. Whether you’re looking for a vacation retreat or a year-round sanctuary, this property delivers the quintessential Vermont four-season lifestyle. Don’t miss this rare opportunity, schedule your private showing today!

New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three levels. Planned for a stone fireplace. Prepped for decks on the east and west sides of the House. Septic plan is designed by a Vermont Licensed Engineer to be built, area is cleared for the system. There is Timber on the property estimated at 15,000 board feet of volume. Close to Wilmington and Dover, Lake Whitingham, Burrington Brook. Deerfield River, North River, Burrington Brook, Haystack Club Golf and Ski and Mount Snow Resort.

This recently updated 1920s Vermont farmhouse features 4 bedrooms, 2 full bathrooms, and a versatile loft space on just over 8 acres! Large, updated windows showcase mountain views and allow natural light to fill every room, highlighting the home's charming original details alongside modern updates. The first floor has two bedrooms, both full bathrooms, first floor laundry, as well as TWO spacious living rooms! One living room showcases exposed beams, a vaulted wood ceiling, a cozy wood stove, and loft space above which could be perfect for a reading nook, office, or additional guest area. Updates in this home are tasteful, modern and add substantial rustic character. Furnishings are included in the sale. With two convenient points of entry, the home easily accommodates a dedicated mudroom or simple access directly through the kitchen. This versatile layout allows for one floor living with the expansive space of two bedrooms on the second floor! The property includes a spacious 52' x 35' barn that offers excellent storage, workshop space, or room for hobbies and equipment. The outdoor setting has a small apple orchard and a former smokehouse once used for curing meats, adding unique character and history! Outdoor enthusiasts will appreciate many local hiking trails, direct snowmobile and ATV trail access, along with the convenience of an EV charger hookup. Just 22 miles to Mount Snow Ski Resort, 14 miles to Wilmington Village, 15 miles to Berkshire East in Charlemont and 18 miles to MASSMoCA in North Adams, you are centrally located to all forms of enjoyment!

Historic 1876 church, formerly known as the Union Church of Heartwellville, offering a rare blend of preserved character and updated functionality. Original architectural elements remain, including the bell and belfry, while the interior has been renovated to provide an open-concept layout that still reflects the traditional church design. With its unique layout and destination-worthy setting, this property presents exciting potential as a one-of-a-kind short-term rental or Airbnb opportunity. Conveniently positioned near MASS MoCA and the shops and dining of North Adams, with easy access to year-round recreation. A portion of the land is located across the road with views to the Deerfield River and it cannot be developed.