Properties Near 292 Deer Hill Road Whitingham, VT

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!

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..

Classic Jacksonville Village farmhouse filled with warmth, character, and thoughtfully curated spaces that feel straight out of a charming country inn. Exposed beams, high ceilings, wide-plank wood flooring with period details, built-ins, and inviting gathering spaces create an atmosphere that immediately feels comfortable, relaxed, and lived in the very best way. Kick off your shoes, curl up with a book, and enjoy the historic and classic charm this home offers both inside and out. The flexible floor plan includes 4 bedrooms and 2 baths, with the current owners utilizing both second-floor bedrooms as a primary wing and an expansive suite-style retreat. A separate guest wing offers two additional bedrooms, bonus space for overflow, and a full bath, creating privacy and versatility for guests, extended family, or work-from-home needs. Mudroom entry and full laundry add everyday practicality to the home's timeless appeal. Formal dining room, formal sitting room, and expansive great room with skylights. Outside, enjoy a covered farmer’s porch, fire pit area, mature perennial gardens, ample parking on .60 acres, and the peaceful sounds of the East Branch of the North River flowing through the heart of Jacksonville Village. A large powered shed/outbuilding offers excellent storage and workshop space, while also presenting exciting potential for use as an artist studio, hobby space, or flexible bonus area. Standing seam metal roof, drilled well, and public sewer add important modern infrastructure to the historical and charming features. Conveniently located to Mount Snow , the Deerfield Valley, downtown Wilmington, lakes, hiking, skiing, and year-round recreation in beautiful Southern Vermont. Only 15 minutes to Massachusetts and 25 minutes to Interstate 91 for an easy commute to work, home, or play.

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.