Properties Near 292 Deer Hill Road Whitingham, VT

3 Bed, 3 Bath, 9+ Acres and exceptionally well cared for country retreat! Lovingly maintained & thoughtfully reimagined by the same owners for more than 20 years, every improvement has been made with care & purpose. The result is a home that feels warm, welcoming, effortlessly comfortable & beautifully connected to its surroundings. Set on 9± acres of rolling fields, mature woods & groomed walking trails, the property begins to tell its own story of Vermont living. Well manicured, planned perennial gardens, split rail fence, stonewalls and stonework, arbor, broad lawns, charming footpath, winding over natural stone & wooden bridges to your year-round brook! A converted barn with power and water is an inspiring studio, yoga retreat, or creative workspace, complete with an antique plunge sink, the perfect place to rinse vegetables gathered from the garden. Inside, 3 bedrooms, 3 baths, primary suite with a classic clawfoot soaking tub, a den, and thoughtfully updated living spaces. Four-zone mini-splits provide efficient heating, air conditioning & dehumidification. Wildlife is a regular visitor here, from deer, fox & wild turkey to soaring birds of prey. In the evening, gather something fresh from the garden, pick a bouquet, and head back to the house to linger over dinner on the deck and gaze at the mountain views! Welcome the next day with coffee as the sun rises over the surrounding hills. Take a stroll down the footpath to the brook or kick off your shoes and climb into a hammock with a book. This isn't simply a home; it's an invitation to slow down. It's the kind of home, property, and lifestyle that reminds you why you came to Vermont in the first place.

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.

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!

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—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.

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.

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.

Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary bedroom, 2 guest bedrooms, and a half bath. There is a full unfinished basement with great storage space, laundry, and a full walkup staircase. A tremendous primary home or Vermont retreat.

Escape to the beauty of Southern Vermont with this newly built chalet, offering comfort, flexibility, and year-round recreation. Situated just minutes from Lake Sadawga and Town Hill Park, this property is ideal as a full-time residence, vacation home, or investment getaway. The well and septic system were installed in Spring 2026, providing peace of mind and a strong foundation for future enjoyment. The interior is ready for your personal touch, with the opportunity to build a kitchen tailored to your lifestyle or utilize the thoughtfully designed kitchen plans already created by the builder. Enjoy the warmth and charm of chalet-style living, surrounded by the natural beauty of the area and endless outdoor activities throughout every season. Whether you're boating, fishing, hiking, snowmobiling, skiing, or simply relaxing in a peaceful setting, this property offers something for everyone. Being sold partially furnished, this move-in-ready retreat allows you to start enjoying Vermont living right away while adding your own finishing touches. A rare opportunity to own a newly constructed getaway with major infrastructure already in place and the flexibility to make it uniquely yours.

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.