Properties Near 16 Church Street Woodstock, VT

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation center) since 1890. On long summer days, the sounds of children enjoying the swimming holes and tubing in the rapid runs below float up. The floor plan has been adapted to modern lifestyles across three levels. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The soothing music of the water rose to a crescendo in August 2011 as Hurricane Irene swept into Vermont as a tropical storm, resulting in a FEMA-designated 500-year flood event that inundated basements, as it did many homes in Woodstock and other river towns. Subsequently, the owners have replaced the lower-level sheetrock and boiler and have invested in an engineered barrier wall. The home is within walking distance of Village shops, restaurants, and resort amenities. A peaceful hideaway close to everything.

US Route 4 in Vermont - the east/west corridor from I-89 and the Killington Ski Area. Highway frontage between Quechee and Woodstock, VT. Minutes from Dartmouth College in Hanover, NH; near the intersection of I-89 and 91 at the Connecticut River; also close to Northern New England’s major DH Medical complex and Cancer Center in Lebanon, NH, as well as the VA Hospital in White River Junction. 1.5 story Cape (3 bedroom/2 bath - 2,334 sq ft) from 1850, with numerous outbuildings. The site of a very successful farmers market for many years, then Fool on the Hill, a gift/crafts/novelties business. In addition to the barn, 3 large sheds (1,440 sf - 810 sf - 500 sf) suitable for outdoor events. Silos with folk-art handmade metal roofs are part of the barn. Water views of the Ottauquechee River and a pond on the property. Tillable organic soil on 9.1 acres, paved driveway to farm stand sheds with ample parking. Plans for developing can be available to accepted BUYER w/agreement.

Open House 10-2 Saturday 6/13 - Commanding a spectacular position atop 35 pristine acres, this extraordinary contemporary estate offers sweeping, long-range panoramas of the Quechee Valley, the Woodstock hills, and the Quechee Ski Hill. Designed as a true sanctuary, the home spans over 4,000 square feet of impeccably curated living space, where architectural elegance and natural beauty exist in perfect harmony. Sliding doors invite the landscape indoors, while custom millwork, tile and wood floors, and radiant heat create a refined yet welcoming atmosphere throughout. The main level is an entertainer’s showpiece, anchored by a chef’s kitchen and enormous pantry flowing seamlessly into a dramatic great room defined by soaring ceilings and a gas fireplace, ideal for both intimate evenings and elevated gatherings. The primary suite is a private retreat of light and serenity, featuring dual walk-in closets and a spa-inspired ambiance. A beautifully appointed in-law suite, with both interior and private access, offers exceptional flexibility for guests or multi-generational living, all while preserving privacy and independence. In total, the residence includes four bedrooms, three full baths, and a half bath at the entry. The lower level extends the living experience with a generous media room perfect for cinematic evenings or game-day entertaining, accompanied by two additional bedrooms and a full bath. Beyond the home, rolling pastoral meadows transition into timeless Vermont woodland, creating a secluded four-season haven alive with wildlife and tranquility. A 26’ x 36’ barn offers versatile space for storage, studio, or workshop use, while a two-car garage and ample parking ensure effortless convenience. Ideally situated just minutes from golf courses and fine dining, near Woodstock’s shops and trails, and within easy reach of Dartmouth College, DHMC, and Killington, just 20 miles west. A rare offering delivers privacy and prestige - Not in QLLA.