426

Windsor County VT Homes for Sale

Section Image
  • /41

    $5,950,000

    • 8 Beds
    • 7.5 Baths
    • 10,062 Sq Ft

    3800 Weston-Andover Rd, Andover, VT 05143

    The ultimate family compound, award nominated video tour. This fully furnished and equipped luxury property is located in Andover, Vermont, set on 384 acres in the iconic Green Mountains, offering a rare blend of nature’s bounty, seclusion, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3800 Weston-Andover Rd, Andover, VT 05143
  • /60

    $859,000

    • 2 Beds
    • 3 Baths
    • 2,250 Sq Ft

    60 Spencer Hollow Rd, Springfield, VT 05156

    Experience timeless elegance and rural charm at this meticulously crafted country estate, featuring a historical reproduction Shaker-style home designed by renowned architect McKee Wing Roth and built in 1991. Set on 15 deeded acres of rolling pastures, this unique estate blends traditional design with modern sustainability. Conveniently located 6.5 miles from the renowned Crown Point Country

    Kristen Breeden Southern Vermont Realty Group

    60 Spencer Hollow Rd, Springfield, VT 05156
  • /32

    $72,999

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft

    185 Riverbend Way, Woodstock, VT 05091

    Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

    Mendi Michael Engel & Völkers Okemo

    185 Riverbend Way, Woodstock, VT 05091
  • /60

    $2,750,000

    • 7 Beds
    • 10 Baths
    • 13,410 Sq Ft

    51 E Ash Rd, Plymouth, VT 05056

    Welcome to Eureka House. This 7 bedroom Robert Carl Williams designed home is the ultimate in Vermont luxury and privacy. Enjoy unparalleled amenities like a 14-seat theater with stage, drive-through portico entrance, 2 story living room with gallery, 2 laundries, bedrooms are all en suite, and a 2 1/2-story carriage house with 3-car garage as well as living space above. The property is framed

    Kevin Barnes William Raveis Real Estate Vermont Properties

    51 E Ash Rd, Plymouth, VT 05056
  • /37

    $399,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,148 Sq Ft

    40 Fenton Rd, Chester, VT 05143

    This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

    John Napier TPW Real Estate

    40 Fenton Rd, Chester, VT 05143
  • /45

    $1,100,000

    • 4 Beds
    • 4 Baths
    • 2,640 Sq Ft

    307 Remick Rd, White River Junction, VT 05001

    Nestled at the end of a quiet dead-end road, this 68-acre private homestead offers exceptional privacy, timeless New England charm, and direct access to over 560 acres of town-owned land—the Hurricane Forest and Hurricane Wildlife Refuge. With conservation land on two sides, this property is a rare blend of seclusion, natural beauty, and convenience—a one mile drive to the intersection of RT 89

    Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

    307 Remick Rd, White River Junction, VT 05001
  • /37

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    143 Spoonerville Rd, Springfield, VT 05150

    Are you looking for a home with a large open yard, a stream that runs along the property line, a treehouse, and a garage? If so, this updated home is waiting for you! The breezeway (also a finished mudroom) enables you to stay dry in the Vermont weather when you park in the garage. Power lines? Not here, as they are all buried. Many improvements have been made since purchasing, including new

    Heather Gleim CENTURY 21 North East

    143 Spoonerville Rd, Springfield, VT 05150
  • /11

    $135,000

    • Land
    • 1.19 Acres
    • $113,445 per Acre

    5417 Fletcher Ln, Hartford, VT 05059

    Located in the highly desirable Upper Willard Road neighborhood of Quechee Lakes, this 1.19-acre parcel offers an excellent opportunity to build your Vermont retreat in one of the region’s premier four-season communities. The gently sloping terrain provides flexibility for a homesite, either closer to Fletcher Lane or further back at a higher elevation toward the west end of the property. Recent

    Richard Higgerson Higgerson & Company

    5417 Fletcher Ln, Hartford, VT 05059
  • /46

    $1,400,000

    • 4 Beds
    • 3.5 Baths
    • 4,487 Sq Ft

    42 Cedar Dr, Ludlow, VT 05149

    Welcome to Okemo Pines! This luxurious four-bedroom, three-and-a-half-bath timber frame home offers an open-concept main floor with white oak floors and customizable bonus rooms. The great room features a cathedral ceiling, ample windows that frame the views, and a fieldstone fireplace.The chef's kitchen includes a farmer's sink, custom cherry cabinetry, and a walk-in pantry. The main level

    Katherine Burns William Raveis Real Estate Vermont Properties

    42 Cedar Dr, Ludlow, VT 05149
  • /40

    $280,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    818 Davidson Hill Rd, Chester, VT 05143

    Located on the Chester, N. Springfield town line, this cute house sited on just under 3 acres is move in ready. It offers It offers 3 bedrooms two full baths and a designated laundry room. The renovated kitchen featuring stone countertops and nicely styled cabinets. In addition, there is beautiful post and beam back porch that is perfect for morning coffee and late afternoon quiet. With a small

    John Tolosky Barrett and Valley Associates Inc.

    818 Davidson Hill Rd, Chester, VT 05143
  • /29

    $169,500

    • 2 Beds
    • 1 Bath
    • 1,500 Sq Ft

    1438 Gravelin Rd, Perkinsville, VT 05151

    Country Setting on a shared drive surrounded by 3 acres w/ a small pond. First floor has 1 BR, full bath, kitchen/dining area and living room. Lower level has 1 BR and laundry room. Heat is a propane Rannai direct vent, plus a lower-level pellet stove. Property is in need of repair but livable. This is an ideal candidate for a 203K loan.

    Don Chabot Town and Country Realty

    1438 Gravelin Rd, Perkinsville, VT 05151
  • /52

    $325,000

    • 5 Beds
    • 4 Baths
    • 2,963 Sq Ft

    513 Giddings St, Springfield, VT 05150

    Nestled on over an acre +/- of level land, this well-maintained home offers a wealth of space and potential for any lifestyle. With a large shed, a 3-car carport/workshop, and even a chicken coop, you'll have plenty of room to store, work, and play. The first floor features a generously-sized bedroom with bay windows, a beautifully refinished bathroom with a walk-in shower, a large kitchen,

    Chelsea Richardson Barrett and Valley Associates Inc.

    513 Giddings St, Springfield, VT 05150
  • /60

    $950,000

    • 3 Beds
    • 3 Baths
    • 2,794 Sq Ft

    34 Midsomer Meadows Ln, Woodstock, VT 05091

    Welcome to Starry Hill, a fully furnished and somewhat recent Airbnb rental. Handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock, built over 4 years by a family of loggers and master craftsmen. This exceptional home features Eastern white pine walls, hemlock structural beams, and pine ceilings/flooring sourced from the property. Warm,

    John Bassette Bassette Real Estate Group

    34 Midsomer Meadows Ln, Woodstock, VT 05091
  • /48

    $689,000

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

    598 E Woodstock Rd, Woodstock, VT 05091

    Discover the charm of historic Woodstock, Vermont in this spacious, light-filled home just minutes from the village green. Blending timeless New England character with modern comfort, this property offers an abundance of space and versatility — ideal as a full-time residence or a relaxing ski-season getaway.This inviting home features hardwood floors, custom cherry built-ins, and two fireplaces,

    Erika Smith RE/MAX Upper Valley

    598 E Woodstock Rd, Woodstock, VT 05091
  • /24

    $299,000

    • Land
    • 4.3 Acres
    • $69,535 per Acre

    00 Chateauguay Rd, Barnard, VT 05031

    A rare and beautiful parcel of land that is cleared, level and ready to be built upon with over 1200 feet of frontage along the North Branch of Locust Creek.Locust Creek runs year round with water falls and deep pools, not only pleasant to look at, but fun to play in.Site prep costs for a parcel like this will be considerably lower than wooded lots that require clearing and excavation.

    Stan Butler Four Seasons Sotheby's Int'l Realty

    00 Chateauguay Rd, Barnard, VT 05031
  • /59

    $18,000,000

    • 7 Beds
    • 10 Baths
    • 12,520 Sq Ft

    355 Greene Rd, Woodstock, VT 05071

    Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

    Chris Lang

    355 Greene Rd, Woodstock, VT 05071
  • /35

    $729,000

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft

    101 Okemo Trailside Extension Unit 41C, Ludlow, VT 05149

    This beautiful three bedroom plus family room townhome is quietly located bordering a woodland with long distance mountain views, and is serviced by a private shuttle that whisks you to and from the Upper Sachem ski trail to your door. An expansive mudroom with tile floor and cubbies leads out to your own exterior ski closet. The large custom kitchen includes wood cabinetry, stone countertops,

    Andre Menard Mary W. Davis Realtor & Assoc., Inc.

    101 Okemo Trailside Extension Unit 41C, Ludlow, VT 05149
  • /16

    $399,000

    • Land
    • 13.4 Acres
    • $29,776 per Acre

    00 N Hill Pent Rd, Ludlow, VT 05149

    Opportunity awaits with these two connected wooded building lots totaling 13.44 acres, offering easy access to the VAST snowmobile trail network. Located on a quiet, dead-end country road, this peaceful setting is ideal for those seeking a private getaway with four-season recreational opportunities right at your doorstep. Lot A is 4.67 acres and lot B is 8.77 acres. Both parcels include

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    00 N Hill Pent Rd, Ludlow, VT 05149
  • /21

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft

    111 Lakeland Dr Unit D, Quechee, VT 05059

    Experience the ultimate four-season lifestyle in this desirable end-unit condo at Quechee Lakes. Perfectly situated for both relaxation and adventure, this home offers ultimate convenience with both the Highland Golf Course and Lakeland Golf Courses just steps from your door, and the best of the Quechee Club just a short stroll away. Enjoy the ease of a first-floor primary bedroom and an open,

    Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    111 Lakeland Dr Unit D, Quechee, VT 05059
  • /43

    $850,000

    • 4 Beds
    • 3.5 Baths
    • 2,970 Sq Ft

    1877 Willard Rd, Hartford, VT 05047

    Stunning Deck House perfectly designed for light, views, and easy Vermont living. Soaring floor-to-ceiling glass in the entryway and stairwell connects all levels and creates a warm, treehouse-like feel, drenched in natural light. Honey-colored hardwood floors warm the main level, while wall-to-wall carpet and tile finish the rest of the spaces. The main level also features a striking stone

    Derek Cosentino Four Seasons Sotheby's Int'l Realty

    1877 Willard Rd, Hartford, VT 05047
  • /53

    $415,000 New Construction

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft

    696 Vermont Route 100, Ludlow, VT 05149

    LUDLOW: Minutes from Okemo Mountain Resort and Fox Run Golf Club. Approx. 600' of frontage on Lake Pauline with private dock. Permits are required to complete renovations. The property is private and level. There's an Artist Studio near the road that isn't currently used and needs to be rehabilitated. This unique property needs a new owner to complete it. Make this your dream property!

    Melissa Loughan Westside Real Estate

    696 Vermont Route 100, Ludlow, VT 05149
  • /10

    $479,000

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft

    13 Bullard St Unit 15, White River Junction, VT 05001

    Fully rented duplex with strong rental history. One side has been completely remodeled and updated with slate flooring. vinyl planking and carpet in the bedrooms. Tile shower and granite countertops and new windows. Both sides have a full basement with washer and dryers. one with a boiler and one with a hot air furnace. Nice private back yard. Both driveways have recently been black topped.

    David White OwnerEntry.com

    13 Bullard St Unit 15, White River Junction, VT 05001
  • /14

    $215,000

    • Land
    • 22.29 Acres
    • $9,646 per Acre

    0 Jericho St Unit 5062382, Hartford, VT 05001

    Discover 22.29+/- acres on Jericho Street in Hartford, VT. This wooded parcel offers a peaceful mix of trees and natural beauty—perfect for building your dream home, creating your own trail system, or simply enjoying the quiet serenity of the outdoors. Embrace the Vermont lifestyle surrounded by nature, while being just minutes from Quechee, Woodstock, Dartmouth, and all the shopping, dining, and

    Heather Ashline BHHS Verani Upper Valley

    0 Jericho St Unit 5062382, Hartford, VT 05001
  • /35

    $69,000

    • 1 Bed
    • 2 Baths
    • 775 Sq Ft

    416 Qtr I Jackson Gore Inn, Ludlow, VT 05149

    Jackson Gore Inn, Unit 416 Qtr. I Quarter Ownership - thirteen deeded weeks per year. This one-bedroom, top-floor location is awaiting your family! Its location faces east where you will watch spectacular morning sunrises while sipping on coffee from either your bedroom or living room. There are both hillside and valley views which lend to a peaceful and tranquil environment. With a sleeper sofa

    Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

    416 Qtr I Jackson Gore Inn, Ludlow, VT 05149
  • /13

    $399,900

    • Land
    • 108 Acres
    • $3,703 per Acre

    1928 Vermont 131, Ascutney, VT 05030

    This 108 Acres +/- boasts one of the most beautiful and plentiful sugarbush in the state, that can easily accommodate over 4500 sugar taps. Matured stately maple timber with enough cord word available for a lifetime. Well maintained wood trails traverse the acreage. Several building sites with spectacular Mt. Ascutney views with clearing. This secluded hillside is just 5 minutes to Exit 8, 30

    Don Chabot Town and Country Realty

    1928 Vermont 131, Ascutney, VT 05030
  • /26

    $3,300,000

    • 3 Beds
    • 4.5 Baths
    • 3,682 Sq Ft

    249 Sawyer Rd, Woodstock, VT 05091

    Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

    Andrew Bustin LandVest, Inc/Woodstock

    249 Sawyer Rd, Woodstock, VT 05091
  • /58

    $595,000

    • 6 Beds
    • 3 Baths
    • 3,325 Sq Ft

    29-31 High St, Ludlow, VT 05149

    Location, Location, Location! In the heart of the village, on the coveted, much sought after, quiet High St. is this three family beautiful property. A short stroll to downtown Ludlow and all it has to offer. Two beautiful units in the main house with hardwood flooring, updated kitchens and both with 3 season sun porches. A cozy two bedroom apartment above the three car garage with a covered

    Frank Provance Diamond Realty

    29-31 High St, Ludlow, VT 05149
  • /39

    $560,000

    • 3 Beds
    • 2 Baths
    • 1,552 Sq Ft

    368 Crimson Hawk Rd, Plymouth, VT 05056

    Set in a quiet location, this well-maintained home offers a comfortable and practical retreat with easy access to outdoor recreation. The property feels secluded while remaining conveniently close to the main road.The open floor plan connects the living, dining, and kitchen areas, creating a functional layout for everyday living and entertaining. The living room features a stone fireplace,

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    368 Crimson Hawk Rd, Plymouth, VT 05056
  • /60

    $230,000

    • 1 Bed
    • 1 Bath
    • 856 Sq Ft

    42 Heritage Condo Way Unit 14D, Woodstock, VT 05091

    Welcome to your Woodstock affordable retreat! This inviting, end-unit, two-level townhouse in the sought-after Heritage Condominium community is nestled on a dead-end road just minutes west of the historic village of Woodstock. This bright 856 sq/ft two-level home offers an open-concept first floor with a carpeted living/dining area warmed by Empire gas heat (plus electric backup). From this

    John Bassette Bassette Real Estate Group

    42 Heritage Condo Way Unit 14D, Woodstock, VT 05091
  • /12

    $1,495,000

    • 3 Beds
    • 4.5 Baths
    • 3,120 Sq Ft

    4070 Tichnor Rd Unit 4070, Hartford, VT 05001

    New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

    Richard Higgerson Higgerson & Company

    4070 Tichnor Rd Unit 4070, Hartford, VT 05001
  • /17

    $150,000

    • Land
    • 1.04 Acres
    • $144,231 per Acre

    00 Partridge Rd, Ludlow, VT 05149

    A great spot to build a home in the small subdivision of Partridge Road. Close to the Village of Ludlow with access to town sewer. Surrounded by fine properties on South Hill. Covenants and restrictions in place to protect your investment. Quiet and private location yet only minutes to Okemo Mountain Resort and the Village of Ludlow. Come build your dream home!

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    00 Partridge Rd, Ludlow, VT 05149
  • /57

    $1,249,000

    • 5 Beds
    • 4 Baths
    • 3,282 Sq Ft

    1873 North Rd, Bethel, VT 05032

    On the west-facing ridge of Barnard, Vermont’s fabled North Road, this ca. 1982 Cape enjoys panoramic long-range views of the Green Mountain Range to the west and North. With ten acres of fenced open pasture and a wood lot, a large, detached barn, and plenty of land to use, the property offers a range of possibilities. Expanded and improved by the current owners over the last 20 years, the house

    Richard Higgerson Higgerson & Company

    1873 North Rd, Bethel, VT 05032
  • /53

    $849,000

    • 5 Beds
    • 3.5 Baths
    • 2,890 Sq Ft

    222 Andover Rd, Ludlow, VT 05149

    Discover the perfect blend of comfort, efficiency, and mountain living in this spacious light filled 5-bedroom, 3.5-bath home, ideally located just 10 minutes from premier skiing and close to popular snowmobile trails. Step inside to a bright, open layout featuring a large gourmet kitchen equipped with an extra-large refrigerator, ample counter space, and room for effortless entertaining. Each

    Lisa Kelley Cummings & Co

    222 Andover Rd, Ludlow, VT 05149
  • /11

    $325,000

    • 4 Beds
    • 2.5 Baths
    • 1,589 Sq Ft

    286 Giddings St, Springfield, VT 05150

    This four-bedroom Cape sits on .5 acres of flat land, with a beautiful backyard for family entertainment. The house, also, features a large kitchen with breakfast bar and two car garage, with nice wooden deck.

    Gale Alger Alger Real Estate Agency

    286 Giddings St, Springfield, VT 05150
  • /17

    $49,000

    • Land
    • 1.31 Acres
    • $37,405 per Acre

    1-61 Hawk Spur Rd, Plymouth, VT 05056

    Affordable lot in a convenient Plymouth Lakes Region location, close to all area amenities including skiing and golf at nearby Okemo and Killington Mountain Resorts. Enjoy all four seasons in the quiet community of Hawk West. On-site septic system and drilled well will be needed. Hawk Resort covenants are in place to protect your investment. Come build your Vermont dream home!

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    1-61 Hawk Spur Rd, Plymouth, VT 05056
  • /32

    $2,300,000

    • 4 Beds
    • 4.5 Baths
    • 3,524 Sq Ft

    134 Chester Arthur Rd, Hartford, VT 05047

    A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

    John Wetmore Wetmore Real Estate

    134 Chester Arthur Rd, Hartford, VT 05047
  • /10

    $388,888

    • 1 Bed
    • 2 Baths
    • 884 Sq Ft

    807 Murphys Rd Unit 7D, Quechee, VT 05059

    Beautifully updated one-bedroom plus loft condo located in Fairway Village. Recent improvements include new AC mini-splits, updated bathrooms, new flooring, a redesigned staircase with banister, loft safety windows, wood shelving, new shades, and toilets. The condo is part of the Quechee Club, which offers a wide range of amenities (additional club fee applies along with HOA dues). Fairway

    Kris Lippi Get Listed Realty

    807 Murphys Rd Unit 7D, Quechee, VT 05059
  • /7

    $325,000

    • Land
    • 8 Acres
    • $40,625 per Acre

    1 Carlton Hill Rd, Woodstock, VT 05091

    Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at site. Wonderful opportunity to build your Vermont getaway or primary residence. Enjoy access to four season recreation, Marsh-Billings-Rockefeller National Park, theatre, arts, dining, shopping and a short commute to all

    Mary Mayhew Snyder Donegan Real Estate Group

    1 Carlton Hill Rd, Woodstock, VT 05091
  • /42

    $389,900

    • 3 Beds
    • 2 Baths
    • 2,776 Sq Ft

    64 Summer Hill St, Springfield, VT 05156

    Tucked in one of Springfield’s most sought-after neighborhoods, 64 Summer Hill St offers the perfect blend of comfort, charm, and convenience. This beautifully maintained 3-bedroom, 2-bath home nestled in one of Springfield’s most desirable neighborhoods. Located on a peaceful .28acre lot in the Cherry Hill district, this inviting property offers the perfect balance of comfort and convenience.

    Jamie Watson BHG Masiello Keene

    64 Summer Hill St, Springfield, VT 05156
  • /58

    $635,000

    • 3 Beds
    • 3.5 Baths
    • 2,203 Sq Ft

    44 Freeman Rd Unit B2, Cavendish, VT 05153

    The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This ground floor 3br +loft & den features 3.5 baths. This townhouse condo has floor to ceiling windows that provide natural light throughout. The open living room, dining room, and kitchen offer an inviting atmosphere for gatherings. The ground floor patio offers outdoor seating and has

    Joseph Karl William Raveis Real Estate Vermont Properties

    44 Freeman Rd Unit B2, Cavendish, VT 05153

Showing Results 321 - 360, Page 9 of 11

How to Buy a Home How to Finance a Home How to Sell a Home