484

Windsor County VT Homes for Sale

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  • /59

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,695 Sq Ft

    955 Smokeshire Rd, Chester, VT 05143

    Tucked away on a quiet country road in one of Chester’s most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle, just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside,

    Katherine Burns William Raveis Real Estate Vermont Properties

    955 Smokeshire Rd, Chester, VT 05143
  • /39

    $385,000

    • 1 Bed
    • 1 Bath
    • 656 Sq Ft

    318 Mountain Rd Unit A302, Ludlow, VT 05149

    Experience true slopeside convenience at Okemo Mountain Lodge A302, a remodeled and turnkey one-bedroom, one-bath condominium located at the Clock Tower base area. This top-floor end unit is one of only six residences in the highly desirable Tower section, offering a more private setting and a rare opportunity within the development. The open kitchen, living, and dining area is designed for easy

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    318 Mountain Rd Unit A302, Ludlow, VT 05149
  • /16

    $650,000

    • Land
    • 10.03 Acres
    • $64,806 per Acre

    00 Little Pond Rd, Andover, VT 05143

    Located in the town of Andover, VT, this 10.4 acre parcel, showcasing an amazing long range mountain view, awaits the home of your dreams. The approach to the property is gorgeous with dramatic views and large neighboring parcels. The house site is tucked in the forest, with a roughed-in driveway already in place. This property has been thoughtfully composed, setting the stage for your custom

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Little Pond Rd, Andover, VT 05143
  • /36

    $465,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    233 Landgrove Rd, Weston, VT 05161

    This Weston gem, expanded and rebuilt by the seller in 2003, has been loved and cared for and is now ready for its next lucky owner. Set on a south facing hill on a quiet country road, it promises sunlight and mountain views all year long. Protected on 10 wooded acres, it borders the National Forest while benefitting from a rolling lawn, small pond and decorative gardens. Designed for one floor

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    233 Landgrove Rd, Weston, VT 05161
  • /40

    $800,000

    • 3 Beds
    • 2 Baths
    • 1,649 Sq Ft

    58 Harrison Ln Unit K-102, Ludlow, VT 05149

    Winterplace at Okemo Mountain—where comfort, convenience, and year-round adventure come together for your slopeside retreat. Step inside to a welcoming mudroom, perfectly designed to keep all your ski gear organized after a day on the mountain. From there, the home opens into a bright and inviting living space, ideal for gathering with family and friends. The open-concept layout features a

    Joseph Karl William Raveis Real Estate Vermont Properties

    58 Harrison Ln Unit K-102, Ludlow, VT 05149
  • /34

    $100,000

    • 2 Beds
    • 3 Baths
    • 1,367 Sq Ft

    506/508 Qtr I Adams House, Ludlow, VT 05149

    Adams House Unit 506/508 QII: Quarter ownership. This 2 Bedroom, 3 Bathroom lock-out style unit that sleeps 8 in Adams House is in an excellent location. When you park in the heated garage, you find yourself only steps away from the unit which is located on the first floor. A very short walk down the hall and you pass the owners locker location. The gas fireplace will warm your spirits and make

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

    506/508 Qtr I Adams House, Ludlow, VT 05149
  • /38

    $249,500

    • 1,922 Sq Ft

    3668 Vt Route 103 N, Chester, VT 05143

    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.

    3668 Vt Route 103 N, Chester, VT 05143
  • /28

    $429,000

    • 1,856 Sq Ft

    185 N Windsor St, South Royalton, VT 05068

    Investment opportunity in the heart of South Royalton! Just steps from Vermont Law & Graduate School, this fully occupied three-unit property offers immediate rental income with a strong history of consistent occupancy. Situated on a level 0.66-acre lot, the property includes a wraparound porch, spacious deck, off-street parking, and a detached barn providing valuable storage or workshop space.

    Wendie Wright Coldwell Banker LIFESTYLES - Hanover

    185 N Windsor St, South Royalton, VT 05068
  • /44

    $849,000

    • 5 Beds
    • 3 Baths
    • 4,388 Sq Ft

    223 Coach Rd, Chester, VT 05143

    Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to

    Daire Gibney Barrett and Valley Associates Inc.

    223 Coach Rd, Chester, VT 05143
  • /36

    $549,000

    $26K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,148 Sq Ft

    38 Stony Brook Rd, Stockbridge, VT 05772

    Beautifully maintained and thoughtfully updated, this classic Vermont Cape is nestled on five private, sun-drenched acres in the heart of the Green Mountains. Whether you're searching for a centrally located primary residence or a peaceful mountain retreat, this inviting property offers comfort, privacy, and year-round recreation. Surrounded by forest, the open homesite enjoys abundant sunshine,

    Kyle Kershner Killington Pico Realty

    38 Stony Brook Rd, Stockbridge, VT 05772
  • /36

    $730,000

    • 3 Beds
    • 5 Baths
    • 3,590 Sq Ft

    1104 Main St, Cavendish, VT 05142

    Back on the market and drastically reduced! Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuites, 5 bath log home. The Great Room boasts a local stone floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor

    Frank Provance Diamond Realty

    1104 Main St, Cavendish, VT 05142
  • /60

    $625,000

    • 4 Beds
    • 3.5 Baths
    • 2,656 Sq Ft

    758 Weston-Andover Rd, Chester, VT 05143

    A rare opportunity to own two well-maintained homes on one beautiful country property! The main residence offers 3 bedrooms and 3 baths with a warm, inviting interior featuring hardwood floors, abundant built-ins, and thoughtfully designed living spaces that blend character with everyday comfort. Step outside to the back deck overlooking beautifully landscaped gardens and a spacious lawn—an ideal

    Kevin Barnes William Raveis Real Estate Vermont Properties

    758 Weston-Andover Rd, Chester, VT 05143
  • /52

    $12,950,000

    • 5 Beds
    • 10 Baths
    • 8,827 Sq Ft

    3147 Mount Hunger Rd, Barnard, VT 05031

    Offered as a fully curated legacy estate, Honey Hill Farm encompasses 264.4 extraordinary acres of pastoral beauty, panoramic mountain views, and an unrivaled network of private trails, with an additional contiguous 42.6-acre parcel available for purchase. More than a luxury property, Honey Hill offers the experience of a private park, with nearly 10 miles of trails winding through forests, open

    Keri Cole Williamson Group Sothebys Intl. Realty

    3147 Mount Hunger Rd, Barnard, VT 05031
  • /60

    $4,450,000

    • 7 Beds
    • 6.5 Baths
    • 6,245 Sq Ft

    53 Moon Shadow Dr, Ludlow, VT 05149

    Perched in an unrivaled location on the Moonshadow Trail, this spectacular mountain residence has been thoughtfully and extensively renovated to offer the perfect blend of luxury, comfort, and year-round recreation. Featuring 7 bedrooms and 61⁄2 baths, this exceptional home is designed to accommodate large gatherings while maintaining an inviting atmosphere throughout. The heart of the home is

    Kevin Barnes William Raveis Real Estate Vermont Properties

    53 Moon Shadow Dr, Ludlow, VT 05149
  • /9

    $299,000

    • Land
    • 10.1 Acres
    • $29,604 per Acre

    0 Safford Rd Unit 5097462, Hartford, VT 05059

    Discover the beauty and privacy of Vermont on this exceptional 10.1+/- acre parcel located on Safford Road in Quechee. Situated within the sought-after Quechee Lakes Landowners Association, this property offers a rare opportunity to build your dream home surrounded by mature woods, natural beauty, and abundant wildlife. Enjoy access to Quechee Lakes' extensive amenities, including two

    Heather Ashline BHHS Verani Upper Valley

    0 Safford Rd Unit 5097462, Hartford, VT 05059
  • /10

    $700,000

    • 3,526 Sq Ft

    754 Hartford Ave, Hartford, VT 05001

    Opportunity is in the spin cycle at the White River Junction Laundromat! This turnkey, established business offers a rare chance to own a laundromat in a highly visible location with excellent accessibility and steady customer traffic. Adding to its appeal are two spacious, updated one-bedroom apartments, both fully occupied, providing reliable rental income alongside the business. Positioned in

    Samuel Roberts

    754 Hartford Ave, Hartford, VT 05001
  • /54

    $1,300,000

    • 5 Beds
    • 4 Baths
    • 2,893 Sq Ft

    2141 Twenty Mile Stream Rd, Proctorsville, VT 05153

    Exceptional Vermont Log Home on 23.13 Acres with Horse Property & Mountain Living Appeal.Meticulously maintained and beautifully landscaped, this stunning five-bedroom, four-bath log home offers the perfect blend of rustic charm, modern comfort, and exceptional amenities. Set on 23+ private acres, the property features covered porches, a relaxing hot tub deck, stone patio, and expansive

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    2141 Twenty Mile Stream Rd, Proctorsville, VT 05153
  • /11

    $699,000

    • 4,252 Sq Ft

    62 Twenty Mile Stream Rd, Cavendish, VT 05142

    Turnkey and meticulously maintained, this 4-unit multifamily property offers strong cash flow and peace of mind for the next investor. Listed at just over an 8% cap rate, the property features three 2-bedroom, 1-bath units and one spacious 4-bedroom, 2-bath unit, providing an attractive mix for a variety of tenants. Significant recent improvements include two new heating systems and a partial

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    62 Twenty Mile Stream Rd, Cavendish, VT 05142
  • /24

    $399,000

    • 2,370 Sq Ft

    51 Andover St, Ludlow, VT 05149

    Minutes from Okemo Mountain and the heart of Ludlow, this well-maintained triplex offers the perfect blend of Vermont lifestyle and strong investment performance. Listed at just over an 8.5% cap rate, the property features three units consisting of two 2-bedroom, 1-bath apartments and one 1-bedroom, 1-bath apartment. Residents enjoy easy access to skiing, hiking, restaurants, shops, and the

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    51 Andover St, Ludlow, VT 05149
  • /37

    $815,000

    • 4,723 Sq Ft

    2003 Main St, Cavendish, VT 05142

    Strong cash flow and future upside come together in this well-maintained 7-unit multifamily opportunity. Offered at an attractive 10% cap rate, the property features a diverse unit mix with four 2-bedroom, 1-bath apartments, two 1-bedroom, 1-bath apartments, and a spacious 4-bedroom, 2-bath unit. Recent exterior painting enhances curb appeal while helping to minimize near-term maintenance. The

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    2003 Main St, Cavendish, VT 05142
  • /34

    $311,000

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    223 Eureka Rd, Springfield, VT 05156

    Tucked away in privacy yet perfectly positioned for Vermont living, this fresh, clean 2-bedroom home delivers far more than first glance suggests. A 3-bedroom septic system means room to grow — add that third bedroom when you're ready. The finished basement expands your living space well beyond the footprint. And the crown jewel: a 640-square-foot structure that once served as a sugar house, full

    Allison Griep BHHS Verani Upper Valley

    223 Eureka Rd, Springfield, VT 05156
  • /30

    $799,000

    • 3 Beds
    • 3 Baths
    • 2,004 Sq Ft

    1326 Curtis Hollow Rd, Woodstock, VT 05091

    If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends,

    Mandolyn McIntyre Crow Real Broker LLC

    1326 Curtis Hollow Rd, Woodstock, VT 05091
  • /58

    $950,000

    • 3 Beds
    • 3 Baths
    • 5,164 Sq Ft

    27 Johnson Loop, Ludlow, VT 05149

    Situated on a peaceful street just moments from the Okemo Base Lodge, this exceptional residence masterfully combines premium craftsmanship with the ultimate ski-town convenience. A short walk from the Okemo Mountain Shuttle. Designed for effortless mountain living, the location offers unparalleled flexibility for your ski days: hop on the neighborhood shuttle, take a short stroll, or make the

    Katherine Burns William Raveis Real Estate Vermont Properties

    27 Johnson Loop, Ludlow, VT 05149
  • /24

    $495,000

    • 3 Beds
    • 1.5 Baths
    • 2,052 Sq Ft

    531 Route 12, Hartland, VT 05048

    Nestled on a serene 3.3-acre parcel, this charming 1990s Cape offers privacy and elevated views, just minutes from town. With three spacious bedrooms, two dedicated offices, and a welcoming country kitchen, it’s ideal for work and relaxation. Enjoy the full walk-out basement, oversized two-car garage with a workshop, and a handy shed for your hobbies. A lovely garden area completes this peaceful

    Susanne Pacilio Martha E. Diebold/Hanover

    531 Route 12, Hartland, VT 05048
  • /39

    $649,000

    • 5 Beds
    • 2.5 Baths
    • 4,306 Sq Ft

    88 Summer St, Springfield, VT 05156

    Stepping onto the grounds, it becomes immediately clear that they simply do not make homes like this anymore. This magnificent 1897 Victorian mansion, recently painted in a crisp white exterior, stands as a remarkable testament to an era of unmatched craftsmanship. Yet, for all its grand presence, it remains a well-kept secret. The entry is so subtle off the paved road that a passerby would never

    Franchesca Collins Hall Collins Real Estate Group

    88 Summer St, Springfield, VT 05156
  • /3

    $130,000

    • Land
    • 56.9 Acres
    • $2,285 per Acre

    0 Gird Lot Rd Unit 5097118, Weathersfield, VT 05030

    On an abandoned road running along Blood Brook, this 56 acre parcel of land, rising to 1000 feet-with potential views of New Hampshire, is a perfect property for all sorts of uses, from simple walks to possible development. Seize this opportunity to own land in Vermont that is also only minutes to Route 91 and the rest of the Upper Valley.

    John MacGovern Dark Horse Realty

    0 Gird Lot Rd Unit 5097118, Weathersfield, VT 05030
  • /57

    $839,500

    • 3 Beds
    • 3 Baths
    • 2,667 Sq Ft

    217 S Perry Rd, Woodstock, VT 05091

    This spacious, well-maintained Gambrel-style home is designed for gracious country living, with a post-and-beam frame that creates large gathering spaces accented by two fireplaces, thoughtful features, and abundant natural light. The private parcel, landscaped with perennials and flowering shrubs, is positioned on a rise overlooking the Barnard Valley towards Woodstock, a few miles south. The

    Laird Bradley Williamson Group Sothebys Intl. Realty

    217 S Perry Rd, Woodstock, VT 05091
  • /60

    $1,695,000

    • 4 Beds
    • 3.5 Baths
    • 4,800 Sq Ft

    2706 E Woodstock Rd, Woodstock, VT 05091

    Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former

    Agent Photo

    John Bassette

    Bassette Real Estate Group

    2706 E Woodstock Rd, Woodstock, VT 05091
  • /32

    $1,650,000

    • 7,226 Sq Ft

    533 N Main St, White River Junction, VT 05001

    CASH COW! Here's your opportunity to own a premier 9-unit multifamily investment in the heart of White River Junction! This stunning Victorian is boasting fine architecture, curb appeal, and strong income potential, offering immediate cash flow with the property substantially occupied and generating market rents. Investors will appreciate the estimated 7.5% cap rate, making this an exceptional

    Samuel Roberts

    533 N Main St, White River Junction, VT 05001
  • /28

    $889,000

    • 3 Beds
    • 3.5 Baths
    • 2,383 Sq Ft

    5723 Vt Rt 12 Route, Barnard, VT 05031

    Beautifully renovated, this Barnard Village Cape seamlessly blends modern energy- efficient upgrades with the timeless charm of a classic New England home. A spacious slate-floored mudroom welcomes you into a bright, inviting interior featuring all-new Renewal by Andersen windows and beautifully restored original maple floors. The thoughtfully designed main level includes a stylish kitchen with

    Mary Mayhew Snyder Donegan Real Estate Group

    5723 Vt Rt 12 Route, Barnard, VT 05031
  • /60

    $1,400,000

    • 5 Beds
    • 4.5 Baths
    • 3,224 Sq Ft

    81 Town Farm Rd, Ludlow, VT 05149

    Experience the essence of Vermont mountain living in this exceptional five-bedroom, four-and-a-half-bath retreat, ideally located just minutes from Okemo Mountain Resort and offering partial winter views of the mountain. Nestled on approximately one acre and boasting over 3,300 square feet of beautifully finished living space, this inviting home combines timeless mountain character with the

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

    81 Town Farm Rd, Ludlow, VT 05149
  • /13

    $349,000

    • Land
    • 47 Acres
    • $7,426 per Acre

    0 Tiger Town Rd Unit 2, Norwich, VT 05055

    Discover this 47 acre parcel offering and ideal location for your future home. Enjoy the peace and seclusion of a large acreage property with plenty of room for hiking, exploring, recreation, and outdoor enjoyment. A wonderful opportunity to own a sizable tract of land with endless potential in a beautiful natural setting.

    Peter Roberts Roger J. Roberts Real Estate

    0 Tiger Town Rd Unit 2, Norwich, VT 05055
  • /37

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    62 Pullman Ln, Hartford, VT 05001

    A great opportunity to own a nearly brand new, (2020), Net Zero home in a lovely area of Wilder. The hard working solar panels on the roof provide all the power needed to run this home, and then some. With a lovely open floor plan on the first floor, including a great kitchen living room/dining room, a bedroom and bath, and 2 bedrooms and a bath plus a huge office upstairs, there's a ton of

    Jane Darrach Martha E. Diebold/Hanover

    62 Pullman Ln, Hartford, VT 05001
  • /20

    $500,000

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

    406 Mt View Loop, Rochester, VT 05767

    Well-built and well-situated home in a family neighborhood. One bedroom and one loft bedroom with open concept living room, dining and kitchen open to a covered deck inviting year-round space for enjoying the well-groomed yard and countryside character. Walking down into the walk out basement you find a finished space to expand living area for entertaining or watching sports. A Tesla battery wall

    Patricia Harvey Xsell Realty LLC

    406 Mt View Loop, Rochester, VT 05767
  • /23

    $299,000

    • Land
    • 45 Acres
    • $6,644 per Acre

    1376 Kingdom Rd, Plymouth, VT 05056

    Rare offering of forty-five beautiful acres in the lakes region between Killington and Okemo. You know what they say..."They don't make more land". More photos coming soon or come and take a look yourself and hike around the property. Potential views of Okemo with clearing. Subdivision is possible and has been started at the State level (along with wastewater permitting), but needs to be

    Tyleen Murray Kelley Real Estate, Inc.

    1376 Kingdom Rd, Plymouth, VT 05056
  • /53

    $1,350,000

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

    42 Cedar Dr, Ludlow, VT 05149

    Welcome to Okemo Pines! Tucked away just moments from the slopes, 42 Cedar Drive stands as a premier example of elegant timber frame architecture. This luxurious 4-bedroom, 3.5-bath residence combines rustic Vermont character with modern, high-end finishes. Step inside to an open-concept main level adorned with premium white oak floors. The breathtaking great room serves as the heart of the home,

    Katherine Burns William Raveis Real Estate Vermont Properties

    42 Cedar Dr, Ludlow, VT 05149
  • /52

    $1,350,000

    • 4 Beds
    • 3 Baths
    • 2,138 Sq Ft

    24 Ledgewood Rd Unit B2/B6 GR, Ludlow, VT 05149

    Ledgewood on Okemo. Enjoy a ski on ski off community at Okemo Mountain Resort. This modern, multi-level condo balances contemporary convenience with cozy charm. Ideal for entertaining or a serene ski retreat, the layout features a bright, open-concept main level and an attached one-car garage. The main level boasts light hardwood flooring, a dramatic stone fireplace, and massive windows that

    Katherine Burns William Raveis Real Estate Vermont Properties

    24 Ledgewood Rd Unit B2/B6 GR, Ludlow, VT 05149
  • /50

    $625,000

    • 3 Beds
    • 3 Baths
    • 1,376 Sq Ft

    97 Okemo Trailside Extension Unit 15 C, Ludlow, VT 05149

    Welcome home to Trailside 15C on Okemo. Fully renovated and sold turn-key furnished, this 3-bedroom, 3-bath Trailside condominium is designed for effortless mountain living. The well-thought-out floor plan maximizes space and comfort, featuring a sun-filled main level with vaulted ceilings, exposed beams, and an open-concept kitchen, living, and dining area that captures a classic Vermont vibe.

    Sarah Sheehan William Raveis Real Estate Vermont Properties

    97 Okemo Trailside Extension Unit 15 C, Ludlow, VT 05149
  • /50

    $1,200,000

    • 4 Beds
    • 4.5 Baths
    • 4,636 Sq Ft

    328 Gravelin Rd, Perkinsville, VT 05151

    High Shelter Farm offers the ultimate Vermont lifestyle on 64.64 extraordinary acres of fields, forests, and breathtaking views.. Direct access to Vermont's VAST trail network makes this a true outdoor enthusiast's paradise.The meticulously maintained 4,500+ sq. ft. home is perfectly positioned to capture spectacular views of Mount Ascutney and the White Mountains of New Hampshire.

    Gary Coger Four Seasons Sotheby's Int'l Realty

    328 Gravelin Rd, Perkinsville, VT 05151
  • /50

    $1,600,000

    • 4 Beds
    • 4.5 Baths
    • 4,636 Sq Ft

    328 Gravelin Rd, Perkinsville, VT 05151

    High Shelter Farm offers the ultimate Vermont lifestyle on 271 extraordinary acres of fields, forests, and breathtaking views. Once a working farm, this remarkable property features over six miles of professionally designed trails by John Morton of Morton Trails, providing year-round recreation for cross-country skiing, snowmobiling, ATV adventures, hiking, and exploration. Direct access to

    Gary Coger Four Seasons Sotheby's Int'l Realty

    328 Gravelin Rd, Perkinsville, VT 05151

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