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Farmhouse Homes for Sale in Windsor County VT

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  • /39

    $349,000

    • 4 Beds
    • 3 Baths
    • 3,332 Sq Ft

    397 River St, Chester, VT 05143

    Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops

    Agent Photo

    Lisa Kelley

    Cummings & Co

    (802) 392-0114

    397 River St, Chester, VT 05143
  • /54

    $750,000

    • 3 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    207 Hartness Way, Hartford, VT 05001

    Are you looking for the ideal energy efficient property, perhaps perfect as a 2nd home or investment opportunity? The Sellers have paid less than $3,300 per year covering all utilities for this premium energy efficient home. Discover the perfect blend of comfort, efficiency, and adventure in this beautifully designed, sunny and bright newer-build home, nestled within Vermont's coveted Quechee

    Tyler Hall BHHS Verani Upper Valley

    207 Hartness Way, Hartford, VT 05001
  • /39

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    76 Goldthwaite Rd, Chester, VT 05143

    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

    76 Goldthwaite Rd, Chester, VT 05143
  • /59

    $1,150,000

    • 5 Beds
    • 4.5 Baths
    • 3,370 Sq Ft

    1036 N Main St, Bethel, VT 05032

    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

    1036 N Main St, Bethel, VT 05032
  • /42

    $4,500,000

    $1M PRICE DROP
    • 4 Beds
    • 2 Baths
    • 3,150 Sq Ft

    85 Pallottas Hill Rd, Ludlow, VT 05149

    MAJOR 7 FIGURE PRICE REDUCTION! Your Vermont Mountain Retreat Awaits Discover 127 acres of pure Vermont beauty at the foot of Okemo Mountain, just 2 minutes from downtown Ludlow. This rare property offers expansive meadows, forested trails, and panoramic views of Okemo, Mount Ascutney and beyond. Enjoy direct access to cross country skiing, hiking, snowshoeing, the VAST trail system, and

    Frank Provance Diamond Realty

    85 Pallottas Hill Rd, Ludlow, VT 05149
  • /37

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 3,839 Sq Ft

    198 Piper Hill Rd, Weston, VT 05161

    Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house

    Story Jenks LandVest, Inc/Woodstock

    198 Piper Hill Rd, Weston, VT 05161
  • /52

    $260,000

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    50 Bates Rd, Cavendish, VT 05142

    Welcome to 50 Bates Rd, a charming 1920s Vermont farmhouse perched above the village of Cavendish, offering a country setting with the convenience of being in town. The standout feature is the large covered porch — the kind of welcoming outdoor space that feels from another era and invites you to slow down and take in the setting. This home is ready for updating, but the character is already

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    50 Bates Rd, Cavendish, VT 05142
  • /46

    $718,500

    $31K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft

    37 South St, Woodstock, VT 05091

    Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk-to-all" lifestyle. Stepping inside, newly installed pine flooring guides you through an inviting main level designed for both daily living and effortless entertaining. The cozy living room anchors the home with its warm gas fireplace, while the spacious dining area

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    37 South St, Woodstock, VT 05091
  • /60

    $599,000

    $100K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    5100 Route 100, Plymouth, VT 05056

    (Das Grünebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

    Marni Rieger KW Vermont-Killington

    5100 Route 100, Plymouth, VT 05056
  • /47

    $550,000

    • 3 Beds
    • 4 Baths
    • 2,727 Sq Ft

    1787 Route 100 N, Ludlow, VT 05149

    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

    1787 Route 100 N, Ludlow, VT 05149
  • /33

    $695,000

    $55K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,285 Sq Ft

    47 Pleasant St, Woodstock, VT 05091

    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 spacce), 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

    47 Pleasant St, Woodstock, VT 05091
  • /60

    $1,300,000

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    366 Knapp Pond Rd, Cavendish, VT 05142

    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

    366 Knapp Pond Rd, Cavendish, VT 05142
  • /42

    $694,900

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,938 Sq Ft

    4205 Vermont 131, Weathersfield, VT 05151

    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.

    4205 Vermont 131, Weathersfield, VT 05151
  • /50

    $579,000

    • 3 Beds
    • 2 Baths
    • 2,280 Sq Ft

    353 Brockway Mills Rd, Springfield, VT 05156

    Steeped in historic character and seamlessly updated for modern luxury, this stunning 1875 home offers the perfect blend of old-world charm and contemporary convenience, making it an absolute dream for entertaining Nestled on 3.47+/- quiet acres, this property is a true private sanctuary designed for an elevated Vermont lifestyle. Step inside through the practical and stylish first-floor tiled

    Jill Lawrence The Real Estate Collaborative

    353 Brockway Mills Rd, Springfield, VT 05156
  • /60

    $730,000

    • 4 Beds
    • 3.5 Baths
    • 3,453 Sq Ft

    1432 Union Village Rd, Norwich, VT 05055

    Classic New England home with lots of space, historic charm, and beautiful light. A bright, practical mudroom entry welcomes you, leading to a flexible floor plan anchored by a homey kitchen with a large pantry and eat in space. The property enjoys a spacious family room, a big deck, and a level back yard - an ideal setting for effortless indoor-outdoor entertaining. Upstairs, retreat to a

    Heidi Ruth Coldwell Banker LIFESTYLES - Hanover

    1432 Union Village Rd, Norwich, VT 05055
  • /20

    $249,000

    $11K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,738 Sq Ft

    1009 Vermont 131, Weathersfield, VT 05156

    GREAT LOCATION - Check out this Circa 1840's Farmhouse with attached Garage and Shed on 3.98 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 to Upper Valley and Short drive to

    Don Chabot Town and Country Realty

    1009 Vermont 131, Weathersfield, VT 05156
  • /54

    $399,500

    $40K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,264 Sq Ft

    264 Elm Hill St, Springfield, VT 05156

    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

    264 Elm Hill St, Springfield, VT 05156
  • /56

    $455,000

    • 5 Beds
    • 1.5 Baths
    • 2,205 Sq Ft

    191 Route 100 N, Ludlow, VT 05149

    Nestled between Okemo Mountain and the lakes region, this inviting 5-bedroom home sits on 2 peaceful acres framed by mature trees and an expansive open yard. Filled with warmth and character, the home is a charming reminder of simpler times, offering large sun-filled rooms and generous gathering spaces throughout. At the heart of the home is the open kitchen and family room, where a cozy wood

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    191 Route 100 N, Ludlow, VT 05149
  • /13

    $172,900

    • 3 Beds
    • 2 Baths
    • 1,359 Sq Ft

    136 Store Hill Rd, Bethel, VT 05032

    Property being sold "AS IS".State septic permitting is in progress. Located in quaint E. Bethel Village, this 1825 farmhouse offers an opportunity to finish to your taste.

    Dean Goulet Dunrovin Real Estate

    136 Store Hill Rd, Bethel, VT 05032
  • /45

    $1,299,000

    $151K PRICE DROP
    • 8 Beds
    • 5 Baths
    • 3,814 Sq Ft

    7030 U S 4, Bridgewater, VT 05034

    Situated between historic Woodstock Vermont and the ski slopes of Killington, 7030 US Route 4 provides easy access to the best amenities of the area. The Property has two separate spaces, a standalone two-level garage with ample storage area below, and sits on 6 acres with direct river access. The "Apartment” first floor has an open design with a kitchen, living area, and tucked away bathroom.

    Eric Benvenuti

    7030 U S 4, Bridgewater, VT 05034
  • /45

    $599,999

    • 6 Beds
    • 5 Baths
    • 4,184 Sq Ft

    49 Pleasant St, Ludlow, VT 05149

    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

    49 Pleasant St, Ludlow, VT 05149
  • /16

    $129,900

    • 3 Beds
    • 2 Baths
    • 2,321 Sq Ft

    31 Amsden Hollow Rd, Perkinsville, VT 05151

    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

    31 Amsden Hollow Rd, Perkinsville, VT 05151
  • /37

    $985,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,785 Sq Ft

    1782 Randall Rd, Woodstock, VT 05091

    This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

    Wade Treadway Wade I Treadway Real Estate

    1782 Randall Rd, Woodstock, VT 05091
  • /53

    $525,000

    • 4 Beds
    • 2 Baths
    • 2,232 Sq Ft

    133 Baltimore Rd, North Springfield, VT 05150

    A true farm ready for its next chapter! These grounds have been lovingly tilled, gardened, sown, and harvested; the soil meticulously fed, and the pastures grazed by generations of animals. Hundreds of pounds of produce have been grown in and out of the greenhouse high tunnel. A massive, fixed-rack solar array covers the primary costs of electricity and feeds back into the grid. What is most

    Franchesca Collins Hall Collins Real Estate Group

    133 Baltimore Rd, North Springfield, VT 05150
  • /47

    $395,000

    $44K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,617 Sq Ft

    5798 W Woodstock Rd, Woodstock, VT 05091

    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

    5798 W Woodstock Rd, Woodstock, VT 05091
  • /33

    $295,000

    $4K PRICE DROP
    • 2,702 Sq Ft

    41 Vt Route 103 S, Chester, VT 05143

    Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. There is good road frontage for plenty of parking. Consider the

    Glenn Olney Barrett and Valley Associates Inc.

    41 Vt Route 103 S, Chester, VT 05143
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