Whitingham, VT | 292 Deer Hill Road

This charming chalet on one acre is surrounded by enchanting gardens, with a peaceful stream providing a soothing natural backdrop. Over the years, the seller has lovingly planted thousands of daffodils and day lilies, along with a beautiful mix of perennials, annuals, flowering shrubs, and potted plants that line the walkways, gazebo, and hillside below the home. The original chalet has been expanded with two substantial additions, creating a flexible floor plan featuring a spacious main-level living room with a woodstove and a private primary bedroom or study above, plus a separate dining nook (good for expanding the kitchen). Enter through the welcoming kitchen and dining area, where oak flooring and a wood-burning fireplace create warmth and character. Glass patio doors fill the space with natural light and open to an expansive deck overlooking the lush gardens and is an ideal setting for relaxing or entertaining. Located on a town-maintained gravel road, Chapel Hill Road is home to a mix of year-round residences and vacation getaways. Enjoy nearby Lake Sadawga for kayaking, canoeing, and fishing, or head to Lake Whitingham for swimming, sailing, waterskiing, and more. Conveniently located within easy driving distance of MASS MoCA.

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.

Tucked amongst trees with a great deck. This rural location is not far from great skiing, shopping and all kinds of great dining and entertainment. Over an acre of mostly wooded lot. Property is occupied. No drive by's please..

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.

Enjoy the relaxed pace of Vermont country living in this bright and inviting 3-bedroom, 1-bath home set on 2+/- mostly wooded, level acres just off Route 100. With plenty of room to relax, garden, play, and enjoy the outdoors, this property offers a wonderful setting for a year-round home, vacation getaway, or Vermont retreat. A covered front porch welcomes you home, while the private deck and hot tub off the spacious primary bedroom provide a great place to unwind and enjoy the peaceful surroundings. Inside, the open kitchen, living, and dining area creates a comfortable gathering space, complemented by two additional bedrooms and a full basement with abundant storage. Recent improvements include fresh interior paint and basement waterproofing and insulation by Northern Basement Systems. Outdoor recreation is right at your doorstep, with nearby VAST snowmobile trails and Lake Whitingham/Harriman Reservoir just minutes away for boating and fishing. Mount Snow is approximately 20 minutes away for skiing, snowboarding, hiking, mountain biking, and golf. Downtown Wilmington, with its shops, restaurants, and local amenities, is about 10 minutes away, and MASS MoCA is approximately 30 minutes away. The oversized detached 2-car garage provides plenty of space for vehicles, recreational equipment, and all your Vermont toys, with a full upper level offering additional storage or potential for future use. Conveniently located for an easy getaway from Massachusetts, Connecticut, New York, and southern Vermont, this property offers the space, location, and flexibility to enjoy all that the Deerfield Valley has to offer. Come take a look, you may find this is the Vermont getaway you've been waiting for!

Discover the perfect Vermont four-season retreat in this architecturally unique round home, set on a picturesque 1-acre corner lot in Southern Vermont. Offered fully furnished and move-in ready, this 1,840-square-foot, 3-bedroom, 2-full-bath property is ideal as a year-round residence, vacation home, or turnkey getaway. The welcoming lower level features three comfortable bedrooms, a spacious full bath with a jetted soaking tub, tiled floors, and a glass-enclosed shower, along with a convenient utility room. Upstairs, abundant natural light fills the open-concept living area where the kitchen, dining, and living spaces flow seamlessly together. A cozy wood-burning fireplace creates the perfect gathering place after a day of skiing, hiking, snowmobiling, or exploring the surrounding lakes and trails. A second full bath on the main level adds convenience for both everyday living and entertaining guests. Step outside to enjoy multiple outdoor living spaces, including a sunny second-floor deck, covered patio, established perennial gardens, and a storage shed. The mostly open lot offers space to relax, entertain, and enjoy the peaceful surroundings. Ideally located just 8 minutes from Jacksonville Village, 10 minutes from Harriman Reservoir (Lake Whitingham), 8 minutes from Lake Sadawga, and 17 minutes from Wilmington, this property provides convenient access to some of Southern Vermont's most sought-after recreation destinations. Enjoy skiing at Mount Snow and Berkshire East, boating and fishing on nearby lakes, hiking the Catamount Trail, paddling the Deerfield River, and exploring the VAST snowmobile trail network. With high-speed fiber internet available and all furnishings included, this distinctive home offers the perfect combination of comfort, character, and year-round adventure. Whether you're seeking a mountain getaway, recreational base camp, investment opportunity, or full-time residence, this turnkey Vermont property is ready to enjoy from day one.

Set at the end of a paved, town-maintained road near the village in Readsboro, this 3-bedroom home offers much more space than the bedroom count might suggest, with multiple living areas, bonus rooms and flexible spaces spread throughout the house.The main level starts with a large working kitchen offering plenty of cabinet and counter space, a breakfast bar and an open connection to a good-sized dining area with room for a full table. From there, the floor plan continues into a formal living room, separate den and additional office or flex space, giving you plenty of options for gathering, working from home or simply spreading out. A half bath completes this level.Upstairs are three bedrooms, a full bath and notably generous closet space, while the finished attic adds yet another bonus area that works especially well as a home office, hangout space, den, hobby room or additional flex space.The lower level is unfinished but practical, with a large laundry area, an additional 3/4 bath and a door directly out to the backyard and garden. It is an especially useful setup after working outside or spending an afternoon in the river, with a place to come in, shower off and leave the wet and muddy gear downstairs. Adding to the practical side of the property, the home is served by public water and sewer and has a brand-new 40-year roof. Outside, a large covered farmer’s porch and additional covered side porch give you plenty of room to sit and enjoy the sound and view of the West Branch of the Deerfield River behind the house. Head down to the water to explore the boulders, natural pools and swimming holes, or access the trail directly from the property and follow the old railroad bed toward the recreation area. With room to spread out inside and the river and trail system just outside the door, this is a property that makes it easy to enjoy Readsboro in every season.

4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.