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661 Wright Orchard Rd, Grafton
$669,000
3 Beds ⋅ 2 Baths ⋅ 5097782 MLS
* **Seller offering $10,000 towards closing costs** Short term rental ready turnkey 20-acre Vermont estate Turnkey, beautifully furnished and ready to enjoy. Set on 20 private acres in Grafton, this beautifully maintained 3-bedroom, 2-bath home with a custom office offers the perfect blend of comfort, versatility, and modern convenience. Tucked against the mountains with beautiful long-range views, the property also includes a separate cottage and a young vineyard sold with equipment that is ready for someone to take it to the next stage. High-speed fiber internet and whole house backup tesla battery makes working remotely effortless. The home has been thoughtfully updated throughout, featuring a renovated kitchen with custom Amish cabinetry and stainless-steel appliances, an updated bathroom, modern lighting and electrical upgrades, and fresh interior and exterior paint. A spacious Trex deck provides the perfect place to relax and take in the peaceful surroundings. One of the property's standout features is the attached two-car garage with automatic door openers a rare convenience for a Vermont country home. Outside, you'll find approximately 20 acres of open fields and woodland, a picturesque ½-acre pond, a producing vineyard, and a classic two-story barn, creating an incredible setting for recreation, entertaining, or simply enjoying the beauty of Vermont. Additional highlights include a beautiful fireplace and private dead end road location while remaining within easy reach of Okemo, Stratton, and year-round recreation.

661 Wright Orchard Rd, Grafton

258 Chester Rd, Grafton
$734,000
3 Beds ⋅ 5 Baths ⋅ 5097081 MLS
Set on a beautifully landscaped parcel just minutes from the heart of historic Grafton, this meticulously maintained residence offers timeless New England charm, exceptional craftsmanship, and inviting spaces. Surrounded by mature trees, perennial gardens, and lush lawns, the property provides a peaceful setting with the perfect balance of privacy and convenience. Inside, warm hardwood floors, abundant natural light, and classic architectural details create a welcoming atmosphere. The spacious living room is anchored by a wood-burning fireplace, creating a warm and inviting gathering space for family and friends. Just beyond, the library/den offers a quiet retreat to unwind with a favorite book in front of the home's second wood-burning fireplace, making it one of the home's most inviting spaces. The kitchen blends timeless character with everyday functionality. Rich cabinetry, generous workspace and a spacious walk-in pantry that provides abundant storage along with additional prep space ideal for entertaining. The screened porch offers a peaceful place to enjoy morning coffee, summer dinners, or a quiet afternoon while overlooking the beautifully landscaped grounds. Protected from the elements yet open to the fresh Vermont air, it becomes a favorite gathering place throughout the warmer months. Each bedroom features its own private en-suite bath, providing exceptional comfort and privacy for family and guests. The primary suite serves as a relaxing retreat with hardwood floors, abundant natural light, and a well-appointed bath. Outside, perennial gardens frame the home with colorful blooms throughout the growing season, complementing the stone walkways and classic Vermont landscaping. An attached two-car garage provides convenience and additional storage. Located just minutes from the charming village of Grafton, you'll enjoy one of Vermont's most treasured communities.

258 Chester Rd, Grafton

874 Middletown Rd, Grafton
$1,350,000
5 Beds ⋅ 3 Baths ⋅ 5094211 MLS
Set along picturesque Middletown Road, just beyond the historic village of Grafton, this elegant five-bedroom residence enjoys a setting that feels both timeless and deeply peaceful. Perhaps it is the pleasing symmetry and classic proportions of the c.1815 brick Federal home with its Georgian floor plan. Perhaps it is the views of rolling meadows and rounded hills that unfold in both directions. Or perhaps it is simply the feeling of being here--a quiet sense of belonging that is difficult to explain and impossible to forget. Filled with natural light, the property has a welcoming spirit. A pond, apple orchard, perennial gardens, blueberry bushes, ancient maple trees, and historic stone walls create a landscape rich in beauty. The home sits along a quiet gravel road that forms part of one of Grafton's favorite four-mile walking loops, while trails meander through the property's 66 acres of fields and woodland. The Saxtons River traces one edge of the property. In the early nineteenth century, Major Benjamin Dwinell and his wife, Mehitable, built this home and raised eleven children here. The family prospered from the land, tending a large flock of sheep and cultivating one of the most productive apple orchards in town. By the late 1800s, Grouse Hill had begun a new chapter as a country retreat for a New York family. Over the years it has served as a boarding house, an inn, a full-time residence, and a cherished second home. Through each chapter, it has remained what it is today: a gracious and welcoming place that draws people in, encourages them to linger, and leaves a lasting impression. 22 miles from Okemo. 2 hours 44 minutes from Boston and 4 hours 19 minutes from New York.

874 Middletown Rd, Grafton

170 Townshend Rd, Grafton
$699,000
4 Beds ⋅ 2 Baths ⋅ 5093465 MLS
This handsome turn-key property is available sooner than one might expect! Due to changing life developments, the owners are offering their beloved Vermont home for sale. Not long ago, the 19th century Chapman House underwent a full renovation, including a stunning new kitchen and updated baths. The kitchen features marble countertops, glass-front backlit cabinetry, a deep farmhouse sink, Sub-Zero refrigerator and freezer, and a built-in high-end coffee machine. Blending timeless charm with modern convenience, this space is ideal for both everyday living and entertaining. The kitchen and lovely dining area are bookended by a comfortable den and a formal front parlor, creating a warm and flexible main living space. A first-floor bedroom and full bath complete the main level. Upstairs, you'll find two generously sized bedrooms, each with double closets, along with a beautifully finished bath and two separate office spaces. Combined with fiber optic internet, this home is perfectly suited for working remotely, streaming, or gaming with ease. Additional conveniences include an attached two-car garage with abundant storage space above, as well as a potting area behind. Just off the kitchen is an enclosed porch - the perfect place to enjoy the outdoors in comfort. The setting is equally impressive, a lush lawn, old stone walls, mature trees & this property offers something truly rare - a field in the village! Located near Grafton's infamous Inn & Tavern and only a quarter mile from the Outdoor Recreation Center, the setting is hard to beat. AND-this offering is being sold fully furnished. The current owners have thoughtfully assembled antique furnishings and decor that perfectly complement the character and charm of this antique country village home. Standing seam roof, upgraded electric, 2 fireplace inserts, 2 heat pumps, central air and automatic generator - this house has it all. Just pack your suitcase and come fall in love with this one!

170 Townshend Rd, Grafton

2060 Townshend Rd, Grafton
$2,895,000
6 Beds ⋅ 4 Baths ⋅ 5092853 MLS
A rare opportunity to own one of Southern Vermont's most remarkable private estates, Riverledge Farm encompasses more than 300 acres in the historic village of Grafton. Nestled in the Green Mountains, this exceptional property combines natural beauty, recreation, and a large homestead. A winding approach framed by mature maple trees and classic stone walls leads to the elegant white farmhouse, where timeless Vermont character meets modern comfort. The residence features six bedrooms, four bathrooms, and two kitchens, complemented by an impressive collection of outbuildings, including a 4,000+ square foot timber frame barn for events, five-bay garage with workshop and offices, seven-bay pole barn, and a three-stall horse barn with heated tack room. Additional accommodations include a separate guest or caretaker residence and two rustic cottages. The substantial acreage includes timberland and open pastures, a half-acre aerated pond, more than two miles of streams, and 6.7 miles of private roads and trails throughout the property. Bordering Mollie Beattie State Forest and the South Branch of the Saxtons River, the land offers opportunities for outdoor recreation, forestry, conservation, maple sugaring, and agricultural pursuits. Three access points to the VAST trail network add to the property's recreational appeal. Meticulously maintained grounds, diverse natural features, and a location near the village of Grafton complete this rare Vermont offering.

2060 Townshend Rd, Grafton

54 Main St, Grafton
$639,000
4 Beds ⋅ 3 Baths ⋅ 5090286 MLS
This home IS quintessential Grafton Vermont! Built c. 1850 this stately 4 over 4 colonial served as the Parsonage for the Grafton Church as it is still referred to this day. Privately owned for nearly 30 years this handsome home is ready for new stewardship. Spacious and sturdy, this vintage gem offers plenty of space and has been updated for today’s lifestyle. The first floor offers open concept living space including a renovated kitchen, the heart of the home, with soapstone countertops and custom sink that is within speaking reach of the dining area and comfortable living room space with a wood burning fireplace. A second living room or ‘den’ and a laundry room with half bath completes the comfort and convenience. Upstairs, four generous bedrooms and two full baths create ample space for family and guests. The walk-up attic is easily accessible and offers great storage space. The basement is simple as older homes often are but offers ready access to utilities as needed. A sweet quarter acre with a private grassy area behind the house offers space to unwind or walk to the neighboring ballfield. The driveway is shared but the well and septic were updated to be individual to this home. The detached 2-car garage offers space to get out of New England winters or to store that antique car or two while the screened porch gives protected space for morning coffee or a glass of wine from nearby MKT. Find gourmet meals and live music two doors down at the infamous Grafton Inn. Well set to enjoy all that southern Vermont offers in its rolling hills, open fields, and meandering rivers this home puts you close to its best from skiing to farmers markets, antique shops, and festivals. The Parsonage embodies the best of what Grafton offers - historic and classic blended with comfortable lifestyle.

54 Main St, Grafton

148 Townshend Rd, Grafton
$679,000
3 Beds ⋅ 2 Baths ⋅ 5089886 MLS
This circa 1860 Greek Revival home is one of Grafton Village’s gems, blending historic character with recent, thoughtful renovations. A sweeping backyard framed by rugged stone walls adds to the property’s appeal, while established perennials and a welcoming side porch create an inviting entrance. The delightful country kitchen flows into the formal dining room and living room, where a propane fireplace adds warmth and charm. Wood floors run through most rooms, complemented by high ceilings and a welcoming front entry, leads to side-hall and elegant stairway. Convenient Direct entry from the attached garage/barn, or driveway to mudroom with laundry. On the second floor, 3 bedrooms, a full bath, and a cozy office accessible from the back stairway, along with storage space above the garage. Upgrades include, solar panels, Tesla Powerwall, boiler, and more. The location offers exceptional access to outdoor activities and village conveniences. Grafton Village Park, just behind the house, features hiking and snowshoe trails. Nearby Grafton Ponds offers additional hiking, cross-country skiing, and snow tubing. A snowmobile trail connecting to the inn also links to the wider VAST trail network. Dining at the inn, Takeout and groceries at MKT, Nearby skiing at Stratton, Okemo, and Magic Mountain, Healthcare close by at Grace Cottage Hospital, Community events including Fourth of July fireworks with the VSO and the VSO holiday concert in December.

148 Townshend Rd, Grafton

587 Vt Route 121 E, Grafton
$715,000
4 Beds ⋅ 3 Baths ⋅ 5081734 MLS
Built in 1818 for early woolen mill owner John Woolley, the Woolley House is a rare and beautifully preserved Federal-style brick residence that blends historic character with the demands of contemporary life. Listed on the National Register of Historic Places within the Mechanicsville Historic District, this exceptional property offers unique architectural significance. Classic period details are evident throughout: antique brick walkway, a side-hall layout, blind-arch entryway, fanlight transom, wide pine floors, 12-over-12 windows, and an original central cooking hearth complete with an iron crane and concealed baking ovens. What truly distinguishes the Woolley House is its remarkable versatility for today's professional lifestyle. A converted carriage barn offers three separate private office suites with garden views and exterior access, creating an ideal environment for remote professionals, entrepreneurs, consultants, creatives, or anyone operating a home-based business. Whether you need dedicated workspace for multiple household members, private client meeting areas, or room to grow, the flexibility is exceptional. Paired with fiber-optic internet service, the property delivers the connectivity modern professionals demand while offering comfort and character impossible to find in any conventional office setting. The main residence is equally impressive. The lower level features a custom marble kitchen, formal dining room, three-quarter bath, laundry, and two gracious sitting rooms. Upstairs, four bedrooms, two updated bathrooms, a lounge, a finished loft, and a library retreat offer generous, well-appointed living space. Porches at the back of the house offer three-season enjoyment. A large attic provides significant storage space or potential additional use. Outside, mature perennial gardens, a bank of beautiful rhododendrons, and one of Windham County's most admired hosta collections create a peaceful and private setting.

587 Vt Route 121 E, Grafton

628 Townshend Rd, Grafton
$549,000
3 Beds ⋅ 3 Baths ⋅ 5060321 MLS
One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful stone hearth, and a wood-burning fireplace the perfect winter centerpiece. Bright eat-in kitchen with ample space for a breakfast table move-in ready or a canvas for your personal updates. A cozy, four-season sunroom offers additional living space and opens to a charming patio ideal for morning coffee or evening relaxation. Practical main-level features include a half bath, pantry with laundry, and a versatile dining area with room to entertain. Upstairs, the character continues: Three generously sized bedrooms, office space, and two full bathrooms. Deep windowsills, exposed brick features, and abundant natural light throughout. Additional highlights include wood and tile floors, replacement windows, and a fantastic floor plan. A large, plateau-style backyard with a sweet trail leading to a spacious open field ideal for gardening, recreation, or simply enjoying nature. A one-car garage is tucked under the sunroom for added convenience. This rare stone gem blends timeless charm with modern comfort don’t miss your chance to own a piece of Grafton history.

628 Townshend Rd, Grafton

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