229

Windsor County VT Homes for Sale with Acreage

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  • /60

    $1,395,000

    • 5 Beds
    • 3.5 Baths
    • 4,214 Sq Ft

    28 Mountain View Dr, Ludlow, VT 05149

    This stunning contemporary home blends timeless Vermont charm with exceptional versatility—just moments from Okemo Mountain. Offering 5 bedrooms, 3.5 baths, and over 4,000 square feet across three light-filled levels, the home is thoughtfully designed for both relaxed living and effortless entertaining. The beautifully renovated oversized kitchen serves as the heart of the home, ideal for

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    28 Mountain View Dr, Ludlow, VT 05149
  • /7

    $650,000

    • Land
    • 105.46 Acres
    • $6,163 per Acre

    0 Vermont 131, Ascutney, VT 05030

    Views of the surrounding hills including Mount Ascutney, Little Ascutney and Hawks Mountain. A large parcel with great variety. 35 acres of level cropland. Other fields, forest and transitional areas. Streams running through the land.20 minutes to skiing at Okemos. On the VAST trail system and only a short distance to I91 Exit 8.

    Matthew Spittle Vermont Horse Country Real Estate

    0 Vermont 131, Ascutney, VT 05030
  • /3

    $175,000

    • Land
    • 12.51 Acres
    • $13,989 per Acre

    377 Coach Rd, Chester, VT 05143

    Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    377 Coach Rd, Chester, VT 05143
  • /10

    $450,000

    • Land
    • 69 Acres
    • $6,522 per Acre

    00 Vermont 12, Barnard, VT 05031

    A 69 acre mountaintop building lot with dramatic views of distant mountains in an area of Barnard populated with estate properties. The road is in to a potential building site at the height of the land. Soil testing for septic will be completed as soon as snow clears. Subdivision pending. This parcel is currently comprised of two parcels, one being 40+/- acres and the second being 29+/- which can

    Stan Butler Four Seasons Sotheby's Int'l Realty

    00 Vermont 12, Barnard, VT 05031
  • /3

    $199,000

    • Land
    • 29 Acres
    • $6,862 per Acre

    00 Vermont 12, Barnard, VT 05031

    A beautiful and private 29 acre building lot on a mountainside in an area of Barnard populated by estate properties. A road to the potential building site is in and soil testing for septic will be completed as soon as snow clears. Views of the valley and local mountains currently cleared and can be expanded with additional clearing. The location is a short drive to Woodstock, a shorter drive to

    Stan Butler Four Seasons Sotheby's Int'l Realty

    00 Vermont 12, Barnard, VT 05031
  • /39

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,635 Sq Ft

    1821 Chateauguay Rd, Bethel, VT 05032

    This sunny residence has been a beloved home to several generations of the same Vermont family. The location invites recreational activities! A snowmobile trail passes nearby, for winter excursions and the property is bounded by the cascading waters of Locust Creek, for cooling off in the Summer! The country road that passes by leads to the extraordinary Chateauguay-No Town conservation region,

    John Wetmore Wetmore Real Estate

    1821 Chateauguay Rd, Bethel, VT 05032
  • /15

    $299,000

    • Land
    • 40 Acres
    • $7,475 per Acre

    00 Vermont 12, Barnard, VT 05031

    A perfect opportunity to build in this dramatic and private mountaintop location with long range views to the east and south. An excellent Barnard location in an area of estate properties. Being sold as 40 +/- acres with an additional 29 acres available. Road to building site in and septic soil tests will be performed after snow melt. Subdivision pending. A short drive to Woodstock and an even

    Stan Butler Four Seasons Sotheby's Int'l Realty

    00 Vermont 12, Barnard, VT 05031
  • /17

    $279,000

    • 5 Beds
    • 3 Baths
    • 1,812 Sq Ft

    2100 Baltimore Rd, Chester, VT 05143

    COUNTRY LIVING ON 4.97 ACRES, JUST 6 MILES TO SPRINGFIELD SHOPPING PLAZA. 9 ROOM HOME OFFERS GROUND FLOOR WITH APPLIANCED KITCHEN W/ DINING AREA, LIVING ROOM, SUNROOM, FULL BATH, FRONT BEDROOM, & ANOTHER BEDROOM W/ FULL BATH. THE SECOND FLOOR HAS 2 BEDROOMS PLUS ANOTHER BEDROOM W/ 3/4 BATH AND WALK-IN CLOSET. SEVCA RECENTLY INSULATED ENTIRE HOUSE AND ADDED A NEW FHA OIL FURNACE IN THE SUMMER OF

    Don Chabot Town and Country Realty

    2100 Baltimore Rd, Chester, VT 05143
  • /42

    $725,000

    • 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
  • /58

    $4,999,000

    • 5 Beds
    • 4.5 Baths
    • 9,170 Sq Ft

    62 Moonshadow Dr Unit M4 & M5, Ludlow, VT 05149

    Welcome to one of Okemo’s most distinctive properites, an iconic SKI-ON, SKI-OFF Tennessee log-style home set directly on the Moon Shadow ski trail within Solitude Village. This home offers the ultimate slopeside lifestyle with panoramic mountain views stretching across the Okemo Valley. Crafted with authentic log construction, showcasing broad hewn timbers, wide chinking, reclaimed wood floors,

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    62 Moonshadow Dr Unit M4 & M5, Ludlow, VT 05149
  • /43

    $250,000

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft

    64 County Rd, North Springfield, VT 05150

    Enjoy the ease of single-level living in this 2008 single-wide home set on 2.5 peaceful Vermont acres. The open-concept kitchen and living area is filled with natural light, creating a warm and inviting atmosphere. Offering three bedrooms, one full bath, and a convenient laundry area. Recent improvements include new carpeting and fresh interior paint, making this home truly move-in ready. The

    Carol Slocum Keller Williams Realty Metro-Keene

    64 County Rd, North Springfield, VT 05150
  • /57

    $699,000

    • 2.5 Baths
    • 5,104 Sq Ft

    66 Duttonsville School Dr, Cavendish, VT 05142

    Where History Meets Possibility — An 1862 Schoolhouse Reimagined. Step back in time and into opportunity. Built in 1862, this remarkable historic schoolhouse has been lovingly preserved, its character and craftsmanship thoughtfully maintained while seamlessly supporting modern use.Since 1973, the building has served as the home of a thriving distribution business—proof of its adaptability,

    Gail Engel & Völkers Okemo

    66 Duttonsville School Dr, Cavendish, VT 05142
  • /33

    $195,000

    • Land
    • 3.41 Acres
    • $57,185 per Acre

    119 Advent Hill Rd, Hartland, VT 05048

    Perched high in the scenic hills of Hartland, this exceptional 3.41 acre parcel offers the perfect balance of privacy, sunshine, and sweeping Vermont beauty. Fully surveyed, the property features a selectively cleared and thoughtfully laid out open house site, positioned to capture big vistas overlooking abutting fields and pastureland. In a neighborhood with multi-million dollar homes nearby,

    John Bassette Bassette Real Estate Group

    119 Advent Hill Rd, Hartland, VT 05048
  • /26

    $495,000

    • 2 Beds
    • 3 Baths
    • 2,091 Sq Ft

    85 Townhouse Way Unit 14, Woodstock, VT 05091

    Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    85 Townhouse Way Unit 14, Woodstock, VT 05091
  • /18

    $284,500

    • Land
    • 10.01 Acres
    • $28,422 per Acre

    713 S Hill Rd, Ludlow, VT 05149

    This is not your typical 10 acre parcel! The critical infrastructure elements: a new fully installed 5-bedroom septic system, a drilled well and underground electricity already on the property. Plus, there's a gravel driveway that makes accessing your future home a breeze. This 10 acre parcel is just waiting for your home plans. Approx. 3 miles from Ludlow's Main St. via a year round maintained

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

    713 S Hill Rd, Ludlow, VT 05149
  • /60

    $925,000

    • 6 Beds
    • 7.5 Baths
    • 5,588 Sq Ft

    726 E Ash Rd, Plymouth, VT 05056

    Nestled on a 3-acre private lot at Hawk Resort in Vermont’s Lakes Region, this expansive custom residence offers an exceptional mountain retreat. Thoughtfully designed across four levels--each accessible by elevator--the home provides outstanding separation of space, perfect for hosting family and guests.Designed by architect Robert Carl Williams, the home showcases signature craftsmanship,

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    726 E Ash Rd, Plymouth, VT 05056
  • /32

    $445,000

    • 3 Beds
    • 3 Baths
    • 2,074 Sq Ft

    259 Jay Hill Rd, Hartford, VT 05001

    Bright, easy to maintain and furnished 3 bedroom, 3 bath house with all that Quechee Lakes has to offer. This home includes newer floors. kitchen appliances, 2 remodeled bathrooms, a whole house generator, and a garage with an electric car charger. Enjoy the outdoors with a large deck and an electric dog fence around the whole house.

    Sandra Dell KW Coastal and Lakes & Mountains Realty/Hanover

    259 Jay Hill Rd, Hartford, VT 05001
  • /8

    $275,000

    • Land
    • 1.95 Acres
    • $141,026 per Acre

    3186 South Rd, Woodstock, VT 05091

    1.95 Acre lot minutes from Woodstock Village, South Woodstock, and Green Mountain Horse Association. Kidder Brook runs along the North property boundary, and a sunny lawn area has multiple small gardens. There is a large clearing, and a well-cared for 1973 mobile home on a concrete slab on the property. This lot has tremendous potential in a fantastic location. House is being sold As-is.

    Andrew Hubbell Vermont Real Estate Company

    3186 South Rd, Woodstock, VT 05091
  • /45

    $675,000

    • 4 Beds
    • 3 Baths
    • 3,190 Sq Ft

    598 E Woodstock Rd, Woodstock, VT 05091

    Historic Woodstock, Vermont – Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont’s most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local

    Erika Smith Coldwell Banker LIFESTYLES - Hanover

    598 E Woodstock Rd, Woodstock, VT 05091
  • /14

    $789,000

    • 8 Beds
    • 7 Baths
    • 5,003 Sq Ft

    65 Giddings St, North Springfield, VT 05150

    Check out the Cash flow in this unique 7-unit property. Consisting of six 1-bedroom units, and one 2-bedroom units, this fully rented multi is perfect for the new investor or to simply add to your current portfolio. This building is conveniently located to town close to food, shops and much more! Text for showing requests. Need at least 72 hrs. for tenant notice. Pictures are from before tenants

    Henry Vashaw Twin State Realty LLC

    65 Giddings St, North Springfield, VT 05150
  • /19

    $595,000

    • Land
    • 220.11 Acres
    • $2,703 per Acre

    0 Markham Mountain Rd, Andover, VT 05143

    Discover 220± acres of pristine woodland offering the ultimate blend of privacy, recreation, and opportunity. With a mix of gently level terrain and elevated ridgelines that may offer sweeping mountain views, this remarkable parcel provides endless possibilities — from a private estate setting to potential subdivision. The VAST snowmobile trail runs directly through a portion of the property,

    Kevin Barnes William Raveis Real Estate Vermont Properties

    0 Markham Mountain Rd, Andover, VT 05143
  • /40

    $799,000

    • 7 Beds
    • 9 Baths
    • 7,428 Sq Ft

    52 Upper, Bridgewater, VT 05035

    The ideal property for a SKI CLUB! 7 bedrooms! 6 bathrooms! An immaculate, professionally appointed commercial kitchen! Spacious common rooms and dining areas! A classic and inviting bar/lounge area! An interior with the true Vermont style appeal of exposed beams, wood floors and a stone faced fireplace! This inviting New England style building is perfectly situated midway between world class

    John Wetmore Wetmore Real Estate

    52 Upper, Bridgewater, VT 05035
  • /57

    $1,195,000

    • 4 Beds
    • 2.5 Baths
    • 2,668 Sq Ft

    513 Deer Brook Way, Woodstock, VT 05091

    Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions,

    Keri Cole Williamson Group Sothebys Intl. Realty

    513 Deer Brook Way, Woodstock, VT 05091
  • /48

    $1,600,000

    • 3 Beds
    • 3.5 Baths
    • 3,294 Sq Ft

    39 Elm St Unit B, Woodstock, VT 05091

    The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three

    Derek Cosentino Four Seasons Sotheby's Int'l Realty

    39 Elm St Unit B, Woodstock, VT 05091
  • /22

    $284,500

    • 2 Beds
    • 1.5 Baths
    • 1,063 Sq Ft

    1299 Quechee Main St Unit 2E, Hartford, VT 05001

    Great end-unit condominium in Mill Run across from the Ottauquechee River, offering a bright, open floor plan with cathedral ceilings and a wood-burning stove. The first level features an updated, fully applianced kitchen with a breakfast bar and a half bath. A private deck provides outdoor space with seasonal river views. The lower level hosts two generously sized bedrooms, an updated full bath,

    Linda Hicks Quechee Lakes Real Estate Center

    1299 Quechee Main St Unit 2E, Hartford, VT 05001
  • /23

    $136,000

    • Land
    • 2.85 Acres
    • $47,719 per Acre

    0 Quechee Main St Unit 5076706, Hartford, VT 05059

    Rare opportunity to build in the heart of Quechee Village without a Club membership. This exceptional 2.5-acre lot is beautifully sited overlooking Lake Pinneo, with seasonal views of the Quechee Ski Hill, offering a quintessential Vermont setting in a highly desirable location. Tucked in at the center of the village, the property combines privacy, scenery, and walkable convenience, an

    Brooks Reavill

    0 Quechee Main St Unit 5076706, Hartford, VT 05059
  • /60

    $895,000

    • 4 Beds
    • 2 Baths
    • 4,144 Sq Ft

    1607 Massey Rd, Springfield, VT 05156

    Nestled in the rolling countryside of Springfield, this 1810 Federal-style brick farmhouse stands proudly on 44 breathtaking acres—an offering rich in history, character, and Vermont lifestyle.Open fields stretch out from the home, ideal for gardens, small-scale farming, or simply soaking in the pastoral beauty. Wooded acreage invites exploration, wildlife watching, and the opportunity to tap

    Jessica Citera Cummings & Co

    1607 Massey Rd, Springfield, VT 05156
  • /23

    $750,000

    • Land
    • 2.07 Acres
    • $362,319 per Acre

    Lot 1 Timber Creek Rd, Ludlow, VT 05149

    Timber Creek on Okemo offers a rare opportunity to build in one of Okemo’s premier on-mountain communities. This residential lot is ideally located with easy access to SouthFace Village, giving owners the ability to enjoy the sunny side of the mountain with convenient slope access and year-round resort-style amenities.Ownership includes access to SouthFace Village amenities, including a ski

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    Lot 1 Timber Creek Rd, Ludlow, VT 05149
  • /60

    $4,775,000

    • 7 Beds
    • 6.5 Baths
    • 6,624 Sq Ft

    924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149

    Perched in Solitude, one of Okemo’s most sought-after on-mountain neighborhoods, 924 Okemo Ridge Road offers exceptional slope access, sweeping long-range views, and the scale to comfortably bring generations together under one roof. With 7 bedrooms and 6.5 bathrooms, this is a true ski home—designed for gathering, hosting, and making memories year after year. The home delivers classic ski lodge

    Katherine Burns William Raveis Real Estate Vermont Properties

    924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149
  • /25

    $470,000

    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft

    133 Stagecoach Rd, Norwich, VT 05055

    Situated on a private 4.6 acre lot this unfinished home is awaiting your vision to compete it. Currently a 2-bedroom 1 bath in a lower-level walkout, awaiting the second story. You can live in the home and complete it in your own time frame or bring a builder and finish it now to your specifications. The home is a 44 ft x 26 ft base and can be a single or two story above. It has a 4-bedroom

    Linda White EXP Realty

    133 Stagecoach Rd, Norwich, VT 05055
  • /11

    $150,000

    • Land
    • 1.79 Acres
    • $83,799 per Acre

    83 Coaching Ln, West Windsor, VT 05037

    Shovel ready project in Brownsville Vt.Fully permitted and ready to go for a timber-frame plan up to 5 bedrooms. 1.79 acre vacant lot only for asking price, or built to suit option. Proven aquifer for high production well. Gorgeous views of Mt. Ascutney, minutes to the ski mountain and outdoor recreation center. The area is known for kind welcoming people and local farms. The Ascutney outdoor

    Jason Saphire www.HomeZu.com

    83 Coaching Ln, West Windsor, VT 05037
  • /60

    $1,425,000 Open Sat 10AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    411 Wood Rd, Hartford, VT 05001

    Open House 10 to 1, Saturday April 4th - 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

    Brooks Reavill

    411 Wood Rd, Hartford, VT 05001
  • /35

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,208 Sq Ft

    3078 N Hollow Rd, Rochester, VT 05767

    Nestled in the picturesque hollows of Rochester, Vermont, this charming and fully updated home offers the ease of one-level living in a modest yet wonderfully comfortable package. Antique softwood floors, knotty pine ceilings, and a large bay window framing beautiful North Hollow views create a warm and inviting atmosphere, while the open floor plan is equally suited for entertaining and intimate

    Kyle Kershner Killington Pico Realty

    3078 N Hollow Rd, Rochester, VT 05767
  • /17

    $485,000

    • Land
    • 26.99 Acres
    • $17,970 per Acre

    00 Valley View Dr, Andover, VT 05143

    A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    00 Valley View Dr, Andover, VT 05143
  • /6

    $560,000

    • Land
    • 50 Acres
    • $11,200 per Acre

    90 Reading Farms Rd, Reading, VT 05062

    Exceptional Private Land Offering with Southern Views. A rare opportunity to acquire a private parcel of land located directly off a paved, State maintained road. The property features beautiful southern exposure with multiple potential pond sites and a gently varied landscape ideal for estate development. Surrounded by large, protected, multi-million-dollar estates, the setting offers

    Derek Eisenberg Continental Real Estate Group, Inc.

    90 Reading Farms Rd, Reading, VT 05062
  • /47

    $490,000

    • 3 Beds
    • 2 Baths
    • 1,819 Sq Ft

    400 E Lake Rd, Ludlow, VT 05149

    Versatile Ludlow retreat on 9 acres with proven short-term rental history, offering flexible living options ideal for owner-occupants or investors seeking income near Okemo Mountain. This property is configured as a single-family residence with two distinct living levels, each featuring private entrances and amenities that allow for multiple use scenarios. The ground floor living area includes a

    Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

    400 E Lake Rd, Ludlow, VT 05149
  • /60

    $900,000

    • 5 Beds
    • 3 Baths
    • 3,278 Sq Ft

    114 Mountain View Dr, Ludlow, VT 05149

    A Peaceful Haven on Okemo Mountain. Tucked away at the end of a private road, this sophisticated five-bedroom retreat offers the perfect balance of mountain luxury and quiet seclusion. The heart of the home is a gorgeous great room featuring soaring ceilings, warm hardwood floors, and a majestic masonry fireplace. The open-concept design flows seamlessly into the kitchen and dining areas, making

    Katherine Burns William Raveis Real Estate Vermont Properties

    114 Mountain View Dr, Ludlow, VT 05149
  • /22

    $210,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    2095 Vermont Route 14, Sharon, VT 05065

    1995, 3 bedroom, 2 bath, double wide manufactured home situated on 1.6 acres with 450' of frontage along the White River. The land is open with plenty of room to garden, includes a large shed, and an enclosed porch overlooking the river and surrounding hills.

    Dean Goulet Dunrovin Real Estate

    2095 Vermont Route 14, Sharon, VT 05065
  • /17

    $229,000

    • Land
    • 11.8 Acres
    • $19,407 per Acre

    00 Wildlife Rd, Hartford, VT 05001

    All the things you’re looking for in a housesite: Mountain View of Killington all year, Mountain View of Ascutney seasonally with the potential for all year with some clearing, Sure-Pack driveway installed with a turn around large enough for a fire truck, fully surveyed, septic design and permit in place, cleared housesite, power poles brought to the site for easy electric and internet hookups,

    Franchesca Collins Hall Collins Real Estate Group

    00 Wildlife Rd, Hartford, VT 05001
  • /16

    $229,000

    • 4 Beds
    • 1.5 Baths
    • 2,214 Sq Ft

    2404 Tarbell Hill Rd, Cavendish, VT 05142

    This new to the market home is a must see for location alone: 15 minutes to Okemo gets you skiing all day, or hiking and camping in the state forests. With over 2200 square feet and 3-4 bedrooms, (town has 4 bedrooms, one is accessed by 2 other bedrooms or mudroom could be a bedroom for the count of 4) there is plenty of room for everyone. The living space on the first level is incredible with a

    Christine Lewis Brattleboro Area Realty

    2404 Tarbell Hill Rd, Cavendish, VT 05142

Showing Results 41 - 80, Page 2 of 6

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