Farmhouse Homes for Sale in Windsor County VT

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

Gary Coger Four Seasons Sotheby's Int'l Realty

Enjoy country living and views of rolling hills from this spacious farmhouse set on 5.33 acres in North Hartland, VT with a large detached 2-level barn. Private rural setting with a level, landscaped yard and southern exposure. The home features a formal dining room, first-floor full bath, first-floor laundry, and a mix of hardwood and softwood flooring. All bedrooms are situated on the upper

Carol Shepherd C.G. Shepherd Realty, LLC

Set along the storied banks of the White River, the historic WA Dunham Farm—also known as the Hungerford Farm—offers a rare blend of Vermont heritage, natural beauty, and modern comfort on 92.6 conserved acres. Originally built circa 1867, this extensively restored estate features nearly one mile of private river frontage with a secluded beach, perennial streams, protected woodlands, open

Evan Russell Real Broker LLC

Exceptional mixed-use opportunity with strong visibility on South Main Street in downtown Chester. This versatile property features two residentialapartments—a 2-bedroom, 1-bath unit and a 1-bedroom, 1-bath unit—alongside two commercial spaces, creating a diverse and stable income stream. A large barn addstremendous upside with the potential for additional units or expanded uses, subject to local

The Nancy Jenkins Team Nancy Jenkins Real Estate

Hartland Hill Farm unfolds across rolling meadows in one of the Upper Valley's most picturesque settings. Sited to embrace the surrounding landscape, the property enjoys sweeping pastoral views east to New Hampshire's White Mountains and south over open fields to the iconic silhouette of Mount Ascutney. Mature maples, stone walls, an apple orchard, two ponds, productive farmland, and a classic

Dia Jenks LandVest, Inc/Woodstock

Tucked away from the road in a beautiful country setting, this charming 1920s Cape offers character, privacy, and exceptional flexibility, all just a short drive from Okemo Mountain, Ludlow Village, and the quintessential Vermont village of Weston. The main home features three bedrooms and three bathrooms, along with a large office or den and comfortable living spaces that retain the home's

Sarah Sheehan William Raveis Real Estate Vermont Properties

Charming 1800s farmhouse on 1.5 open, level acres with plenty potential! This 2-bedroom, 1-bath home is a great opportunity for first-time homebuyers, those looking to downsize, or investors. Recent updates include a roof replacement with new sheathing, water barrier, 30-year shingles on the front, and metal roofing on the back. The bathroom was updated in February 2026 with a new shower and

Amy Vashaw Twin State Realty LLC

They say land remembers. On Rush Meadow Road—where rolling fields meet the quiet rhythm of the seasons—there is a place that has been held, cared for, and passed down for over a century. This 103-acre estate is not something that was assembled. It was lived. Worked. Protected. For generations, it operated as a dairy farm, and the land still reflects that stewardship—lush hayfields, a ready-to-tap

Katie Ladue Gilbert BHHS Verani Upper Valley

Hart’s Crossing is a home and a haven featuring a custom 21st-century residence and a comprehensively restored Civil War-era guest house, set on 418 acres of private land. The property provides a refuge in nature, with a kingdom-sized backyard to explore and adventures that change with the seasons. Located at the end of a town-maintained road, the property is a 10-minute drive from either

Laird Bradley Williamson Group Sothebys Intl. Realty

This classic old farmhouse radiates charm and captures the timeless spirit of Vermont living. Lovingly held by one family for over a century, this historic property perfectly balances privacy with exceptional convenience, sitting just over a mile from Main Street in Ludlow. The original home dates back to the pre-1900s, while a thoughtfully integrated 1970s addition introduces rich,

Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

Sheep Run Farm takes its name from the stone-walled lanes where a prosperous 19th-century farmer once moved his sheep between the barn and upper meadows. Nearly two centuries later, those walls still trace the landscape, framing a beautifully reimagined Vermont farmstead on 21± acres in West Windsor, 3 miles from South Woodstock and 8 miles from Woodstock Village.Drawing on the

Dia Jenks LandVest, Inc/Woodstock

From location to layout, this home offers the best of Vermont living. Set along scenic Route 100 in the heart of the lakes region, you’ll enjoy year-round recreation just minutes from Okemo Mountain Resort, Killington Resort, and Plymouth State Park. This thoughtfully remodeled farmhouse blends classic charm with modern updates. Offering 3 bedrooms and 4 bathrooms, the home features generous

Sarah Sheehan William Raveis Real Estate Vermont Properties

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used

John Snyder Snyder Donegan Real Estate Group

Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances,

Franchesca Collins Hall Collins Real Estate Group

Step into timeless New England charm with this historic circa-1760s expanded Cape, offering a wonderful blend of early craftsmanship, character, and modern-day livability. The home showcases classic timber frame construction with hand hewn beams, beautiful wide plank floors, and preserved period details that create warmth and authenticity throughout every room. With three bedrooms and two full

Thaddeus Abare Barrett and Valley Associates Inc.

Beautifully renovated farmhouse offering the perfect blend of timeless New England charm and modern convenience. Situated on a private, low-maintenance lot with both town water and sewer, this inviting home is just a short stroll to Main Street's shops and restaurants and only three minutes from Okemo Mountain Resort.The heart of the home is the spectacular oversized great room, filled with

Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

MOTIVATED SELLER - PRICE REDUCTION - GREAT LOCATION - Check out this Circa 1840's Farmhouse with attached Garage and Shed on 1.98 acres with open meadows and woods. First floor features an Eat-In Kitchen, Full Bathroom, Laundry Room, Living Room, Bedroom and Den/Dining Room with Pellet Stove. Upstairs you'll find 4 Bedrooms that need some cosmetic work. Just 3/4 mile from Exit 8 for easy commute

Don Chabot Town and Country Realty

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

No words describe this property better than peaceful, rural, convenient and historic. Throughout its long life, the top of Elm Hill exudes country. The rugged stone walls, lower barn, tool shed and upper barn reveal an agricultural past. The upper barn has been converted to a 2-car garage and workshop, complete with a half-ton hoist. The upstairs hayloft (attic type storage) is easily accessible

Carol Cole BHG Masiello Brattleboro

Privately sited on 42 pastoral acres, this gracious Vermont country retreat offers approximately 4,000 square feet surrounded by expansive lawns, perennial gardens and two picturesque ponds. The four-bedroom, four-bath residence is ideal for comfortable living and entertaining, with red birch floors, nine-foot ceilings and wonderful connections to the outdoors through multiple screened porches, a

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

Property being sold "AS IS". New State approved septic system is scheduled to be installed within the next month.Located in quaint E. Bethel Village, this 1825 farmhouse offers an opportunity to finish to your taste.

Dean Goulet Dunrovin Real Estate

If you are a skier, this is your hop-on-the shuttle to Okemo location. If you want to park your car and walk to restaurants and shops, this is a great home base to scoot out from. If you want to generate rental income, this is a property that can allow you to have your cake and eat it too. An easy keeper, without a lot of landscape to take care of, this large residence has hardwood floors and

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

Older farmhouse looking for someone to bring it back to what it once was currently has 3-4 bedrooms, two baths, two kitchens, level lot, shed in the front yard area and a brook in the back yard area.

April Shepard Twin State Realty LLC

Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors

Carol Wood Williamson Group Sothebys Intl. Realty

Historic Rowen Farm offers a rare blend of authentic Vermont character, privacy and turnkey ease. Set on 77+ acres of meadow and woodland, the circa-1812 Federal farmhouse has been extensively restored while preserving its soul: original wide-plank floors and exposed beams, original doors and period details, and four wood-burning fireplaces.Inside, approx 3,860 square feet of light-filled

Kim Prins Four Seasons Sotheby's Int'l Realty

Discover the possibilities at Wise Pines, an extraordinary 40± acre property in the heart of Hartland, Vermont, ideally located between Woodstock and Quechee. Surrounded by rolling hills, mature forests, and tranquil walking trails, this unique property was thoughtfully created as a sustainable wellness retreat and offers an exceptional opportunity for its next owner. Wise Pines began its journey

Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover