Windsor County VT Homes for Sale

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  /60

  $1,150,000

  • 5 Beds
  • 3.5 Baths
  • 3,652 Sq Ft

  53 Ponus Rd, Ludlow, VT 05149

  Welcome to this Okemo Mountain home located just a short walk to the slopes! Thoughtfully designed and lovingly maintained by its original owners, this 5-bedroom home offers space, comfort, and the perfect location for year-round enjoyment. Step inside to an open foyer with a convenient half bath and office area, leading into a bright main living space. The open-concept kitchen, dining, and

  Katherine Burns William Raveis Real Estate Vermont Properties

  53 Ponus Rd, Ludlow, VT 05149
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  /20

  $250,000

  • Land
  • 28.5 Acres
  • $8,772 per Acre

  00 Chapel Hill Rd, Sharon, VT 05065

  Located on a class IV road, right after the end of the publicly maintained section of Chapel Hill Road, this 28.5 acre parcel has potential for a camp, off-grid home, or as a recreational getaway. The Seller has roughed in a driveway to a level spot about 600 feet from the town maintained road. Build here or clear at the top of the land for incredible views of Mt. Ascutney, Killington, and

  Tami Sullivan Snyder Donegan Real Estate Group

  00 Chapel Hill Rd, Sharon, VT 05065
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  /42

  $399,800

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056

  Perched at 1,600 feet elevation between Okemo and Killington, this beautifully furnished 3-bedroom, 2-bath condo at Hawk Resort offers the perfect mountain escape--complete with everything you need to move right in.Step into an open-concept living and dining area that flows onto a private deck through glass sliders--perfect for enjoying the sunsets. The living room features soaring cathedral

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056
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  /60

  $1,499,000

  • 4 Beds
  • 3.5 Baths
  • 3,560 Sq Ft

  652 Tierney Rd, Cavendish, VT 05142

  Tucked discretely off a meandering country road you will find this charming 4 bedroom, 3 and 1/2 bath contemporary home sited on 40 acres of land with miles of groomed trails that include a picnic area on Twenty Mile Stream. The grand living room , anchored by a wood-burning fireplace and lined by a wall of windows , frames views of the giant swimming pond and long range mountain views that

  Carol Wood Williamson Group Sothebys Intl. Realty

  652 Tierney Rd, Cavendish, VT 05142
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  /43

  $299,000

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

  436 Mount View Loop, Rochester, VT 05767

  Located on the back side of Mt View Loop is this comfy home, furnished and ready to move right in. Very open concept living space on top floor with woodstove and large dining room set up to enjoy gatherings of any size. Lower floor bedrooms and full bath. Community swim or fishing pond is a deeded right with garden space available and cross country skiing terrain. North Hollow is a

  Patricia Harvey Xsell Realty LLC

  436 Mount View Loop, Rochester, VT 05767
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  /41

  $399,000

  • 5 Beds
  • 3.5 Baths
  • 2,200 Sq Ft

  109 Park Row, Rochester, VT 05767

  The Richard Steele Hubbard home, ideally situated just off the park in the charming village of Rochester, Vermont, is a fine example of the American Foursquare style popular in the late 19th and early 20th centuries. This five-bedroom residence retains many period details, including handcrafted woodwork, hardwood floors, coffered ceilings, stamped tin, and decorative moldings. Thoughtful updates

  Kyle Kershner Killington Pico Realty

  109 Park Row, Rochester, VT 05767
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  /48

  $165,000

  • 3 Beds
  • 1 Bath
  • 1,704 Sq Ft

  3 Chester Rd, Springfield, VT 05156

  Ready for new owners! This 3 bedroom, 1 bath home on .18 acres in Springfield, VT has a kitchen, living room, dining room, and bonus room on the first floor plus 3 bedrooms and a full bathroom on the second floor. There is a walk up attic with lots of room for storage. The house has had a fresh new paint job and the state just completed the culvert project in the backyard. The house was built in

  Amy Hill EXP Realty

  3 Chester Rd, Springfield, VT 05156
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  /60

  $1,375,000

  • 3 Beds
  • 3.5 Baths
  • 3,670 Sq Ft

  170 Scott's Landing, Ludlow, VT 05149

  Welcome to your year-round Vermont retreat at 170 Scott’s Landing, Ludlow. A rare opportunity to enjoy privacy, views, and four-season recreation overlooking Lake Rescue. Tucked away in a serene hilltop setting, this 3-bed, 4-bath home offers the perfect balance of seclusion and convenience, with Okemo Mountain views and a private shared dock on Lake Rescue for your powerboat and effortless

  Joseph Karl William Raveis Real Estate Vermont Properties

  170 Scott's Landing, Ludlow, VT 05149
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  /24

  $675,000

  • Land
  • 41.9 Acres
  • $16,110 per Acre

  8 Grout Rd, Hartland, VT 05048

  Rare, one-of-a-kind land offering with close proximity to Quechee and Hartland.Beautiful building site with Western exposure and exceptional views to the West and North. Pastureland and open meadows for any farming and cultivation needs. Easy construction for additional out buildings or subdivision is possible.Road frontage on Grout Road and the Quechee Hartland road.Private, with

  Charles Bacon Quechee Lakes Real Estate Center

  8 Grout Rd, Hartland, VT 05048
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  /60

  $529,000

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

  74 Spaulding Rd Unit I-4, Proctorsville, VT 05153

  Welcome to the Castle Hill Resort and Spa community! This well-maintained 3 bedroom plus loft upper-level end unit has over 2200 square feet of space and is just a short drive to skiing and Okemo Mountain Resort amenities. The tiled mudroom entry leads to bright open spaces including the kitchen with breakfast bar, as well as the dining and living areas accented by a cathedral ceiling and

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

  74 Spaulding Rd Unit I-4, Proctorsville, VT 05153
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  /41

  $614,000

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

  530 West Rd, Barnard, VT 05031

  Conveniently located less than a mile from Barnard General Store and Silver Lake, this charming 3 bedroom cape sits on just over 3 acres of land with tiered stone walls and green lawn circling the house. Mature trees surround the yard and there is view potential with minor clearing and thinning. The full length back deck offers private outdoor space including a covered grilling area just steps

  Dan Noble Snyder Donegan Real Estate Group

  530 West Rd, Barnard, VT 05031
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  /13

  $489,000

  • 8 Beds
  • 4 Baths
  • 3,483 Sq Ft

  13 Hawthorn St, Hartford, VT 05001

  Strong Cash Flow! Profitable Investment Opportunity! This four unit multifamily property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an on site owner occupancy and the extra rents to pay for your housing.Located in charming Wilder village on a generous .25 +/- acre in town lot. The units consist of three bedroom, two bedrooms and a

  Alex DeFelice The Clerkin Agency, P.C.

  13 Hawthorn St, Hartford, VT 05001
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  /60

  $2,499,000

  • 4 Beds
  • 3.5 Baths
  • 5,079 Sq Ft

  254 Town Line Rd, Plymouth, VT 05056

  First time offered on market! Stunning VT private estate on over 22 +/- acres w/mountain views, gorgeous gardens & 2 ponds one of which is a 7-feet-deep spring fed glacial pond. This exquisite property has been meticulously designed & custom crafted by the owner who is a well-known respected master builder. As you enter this gem you will experience the thoughtful care everywhere you look.

  Marni Rieger KW Vermont-Killington

  254 Town Line Rd, Plymouth, VT 05056
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  /51

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft

  228 Cavendish Gulf Rd, Cavendish, VT 05142

  Brand new custom renovated 3bedroom/2bath home in the charming and desirable town of Cavendish, close to Okemo and four-season recreation. From the outside, this home exudes classic New England charm, but step inside through the mudroom to witness a breathtaking, top-to-bottom modern renovation. Inside, discover a bright, open floor plan with gleaming variegated hardwood floors, and recessed

  Michael Gilman 3GEN Real Estate Inc

  228 Cavendish Gulf Rd, Cavendish, VT 05142
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  /11

  $2,200,000

  • Land
  • 153.73 Acres
  • $14,311 per Acre

  0 Vermont 106, Reading, VT 05062

  Tucked away near the sought-after communities of Woodstock, West Windsor, and Ludlow, this untouched parcel invites endless possibilities. From its elevated perch, it offers sweeping views of Mt. Ascutney and the Connecticut River Valley in every direction. The Northern New England forested landscape is crisscrossed with trails, old roads, and natural springs, perfect for exploration. There are

  Laird Bradley Williamson Group Sothebys Intl. Realty

  0 Vermont 106, Reading, VT 05062
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  /2

  $149,999

  • Land
  • 56.5 Acres
  • $2,655 per Acre

  00 Blackmer Blvd, Stockbridge, VT 05772

  An affordable 56.5 acres of desirable woodland! Pathways heading towards elevated destinations meander up through this tranquil hillside of trees. While some marketable timber has been identified, for many people these classic Vermont woods could be the setting for the construction of a rustic cabin. The property has been "perc tested" by the owners and it has been determined that the property

  John Wetmore Wetmore Real Estate

  00 Blackmer Blvd, Stockbridge, VT 05772
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  /36

  $369,000

  • 5 Beds
  • 1 Bath
  • 2,243 Sq Ft

  2029 N Hill Rd, Chester, VT 05143

  Come, enjoy the quiet charm of Andover in this inviting, private Vermont home—perfect for year-round living or a peaceful getaway. Nestled among evergreens with beautiful snowy views, this property offers easy access to Okemo Mountain, and is also close to Stratton, Magic, and Bromley for skiing, riding, and four-season adventure. Snowmobile enthusiasts will love the nearby VAST trails, and the

  Daire Gibney Barrett and Valley Associates Inc.

  2029 N Hill Rd, Chester, VT 05143
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  /46

  $215,000

  • 3 Beds
  • 2 Baths
  • 2,121 Sq Ft

  222 River St, Bethel, VT 05032

  Nestled on over an acre of serene countryside, this 3-bedroom, 2-bathroom home offers endless potential for those seeking a peaceful retreat with room to make it their own. Enjoy the beauty of nature with direct river frontage, perfect for fishing, kayaking, or simply relaxing to the soothing sounds of the water. The home features a spacious layout with abundant natural light, offering a cozy

  Flex Realty Group Flex Realty

  222 River St, Bethel, VT 05032
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  /28

  $5,500,000

  • Land
  • 127 Acres
  • $43,307 per Acre

  85 Pallottas Hill Rd, Ludlow, VT 05149

  Live, Build, Develop - 127 Acres at Okemo's Doorstep. ~Prime Development Opportunity at the Base of Okemo Mountain. A rare and highly developable 127-acre parcel located just 2 minutes from downtown Ludlow at the foot of world-renowned Okemo Mountain. ~Preliminary engineering, structural work and surveys are complete making this a premier opportunity for a luxury mountain development — luxury

  Frank Provance Diamond Realty

  85 Pallottas Hill Rd, Ludlow, VT 05149
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  /2

  $221,000

  • Land
  • 8.52 Acres
  • $25,939 per Acre

  0 Barrister Dr Unit 3, Hartford, VT 05001

  In-town building lot opportunity! Don't miss this chance to build your single family home or possibly a multifamily project in the Barrister Drive area of Wider, VT. A nice 8.52 +/- acre in-town lot located at the end of Palmer Court or Barrister Drive. This property is adjacent to an additional 25 +/- acre Norwich, VT. lot that is also for sale at $159,000. and could possibly be used for an

  Alex DeFelice The Clerkin Agency, P.C.

  0 Barrister Dr Unit 3, Hartford, VT 05001
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  /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
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  /16

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  9 Walnut St, Hartford, VT 05001

  Welcome to 9 Walnut Street, Wilder, VT, where modern comfort meets affordability in Olcott Falls MHP! This brand-new Redman 25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  9 Walnut St, Hartford, VT 05001
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  /15

  $85,000

  • Land
  • 4.05 Acres
  • $20,988 per Acre

  00 Hillcrest Dr, Andover, VT 05143

  Ready to Build in Southern Vermont! Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for remote work

  Daire Gibney Barrett and Valley Associates Inc.

  00 Hillcrest Dr, Andover, VT 05143
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  /19

  $295,000

  • Land
  • 10.01 Acres
  • $29,471 per Acre

  713 S Hill Rd, Ludlow, VT 05149

  Dear future homeowner! Imagine your dream property just waiting for you and this 10-acre slice of paradise on South Hill Road is exactly that! This isn't just land; it's your blank canvas, totally prepped and ready to bring your vision to life.Critical infrastructure elements already done for you! We're talking a new fully installed 5-bedroom septic system that's good to go, an awesome

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

  713 S Hill Rd, Ludlow, VT 05149
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  /11

  $779,000

  • Land
  • 6.46 Acres
  • $120,588 per Acre

  0 Barnard Rd Unit 20.002, Woodstock, VT 05091

  A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

  John Wetmore Wetmore Real Estate

  0 Barnard Rd Unit 20.002, Woodstock, VT 05091
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  /41

  $999,500

  • 3,218 Sq Ft

  1 Depot St, Hartford, VT 05001

  Excellent Upper Valley investment opportunity! This well-maintained six-unit multifamily property features a desirable mix of 3 one-bedroom apartments and 3 two-bedroom apartments, ideally situated in the heart of Wilder. The property sits directly across from the bus stop and offers convenient access to major employers and amenities — just 9 minutes (4.2 miles) from Dartmouth College and 17

  Loren Wehmeyer Tesla Realty Group, LLC

  1 Depot St, Hartford, VT 05001
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  /50

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  95 Union St, Springfield, VT 05156

  This well-priced home is full of potential and ready for your cosmetic upgrades and a bit of sweat equity. Offering three bedrooms and two baths on a generous lot, it’s conveniently located near the hospital, shopping, and essential amenities. The spacious master bedroom features an ensuite bath, while the additional partially finished attic provides room for expansion or storage. Enjoy relaxing

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  95 Union St, Springfield, VT 05156
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  /60

  $799,000

  • 11 Beds
  • 12 Baths
  • 5,102 Sq Ft

  329 Main St, Cavendish, VT 05153

  Step into history with this beautifully maintained property in the heart of Proctorsville — formerly the Okemo Lantern Lodge and now a thriving short-term rental and family vacation retreat. Rich with character, this historic home showcases timeless woodwork, period details, and plenty of charm, while offering all the updates needed for today’s modern use.Located directly along the Okemo

  Benjamin Cote EXP Realty

  329 Main St, Cavendish, VT 05153
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  /38

  $2,650,000

  • 5 Beds
  • 5.5 Baths
  • 6,188 Sq Ft

  113 N Village Rd, Ludlow, VT 05149

  This beautiful and very spacious newly constructed home, with energy efficient upgrades, has over 6,000 square feet of living space on three levels. Within walking distance to the slopes, located close to the Base Lodge area, this home has everything a ski home needs. Enter through the carefully crafted front door into one of the two mudrooms, or through the two car garage or by the side mudroom

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

  113 N Village Rd, Ludlow, VT 05149
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  /2

  $650,000

  • 5 Beds
  • 2 Baths
  • 2,947 Sq Ft

  108 Main St, Ludlow, VT 05149

  Wonderful investment opportunity in the Ludlow village. 2 unit multi-family with great rental history. Units are in excellent shape. First floor features a spacious 3 bedroom with hardwood floors. The second unit has 2 bedrooms also with Hardwood floors, both in move in ready condition. Units are currently rented and producing income. Just a mile from the Okemo access road and right in the

  Gary Coger Four Seasons Sotheby's Int'l Realty

  108 Main St, Ludlow, VT 05149
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  /40

  $715,000

  • 4 Beds
  • 3.5 Baths
  • 2,654 Sq Ft

  760 E Ash Rd, Plymouth, VT 05056

  Spacious Hawk Resort Home with Scenic Views Enjoy the perfect blend of comfort, space, and mountain charm in this inviting Hawk home. Designed for family gatherings and entertaining, the generous open-concept living area features a beautiful fieldstone fireplace and updated greenhouse windows that bring in natural light and picturesque views. The primary suite offers a cozy fireplace, private

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  760 E Ash Rd, Plymouth, VT 05056
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  /58

  $1,499,000

  • 5 Beds
  • 5 Baths
  • 5,074 Sq Ft

  423 Taft Family Rd, Hartford, VT 05001

  RARE OPPORTUNITY to own a fully renovated luxury home in Quechee Lakes with spectacular mountain views and over 5,000 sq ft of versatile living space on a 4.3-acre double lot. Updated throughout in 2023–2024 and now back on the market due to a professional relocation. This 5-bedroom, 5-bath luxury home offers substance and versatility to suit any new owners’ needs. A private studio apartment with

  Marco Day BHHS Verani Upper Valley

  423 Taft Family Rd, Hartford, VT 05001
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  /17

  $835,000

  • Land
  • 150 Acres
  • $5,567 per Acre

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091

  150 acres of recreational paradise! Absolute and total privacy! Enjoy long views of mountain peaks showing criss crossed ski trails, pristine cascading streams with mesmerizing waterfalls over large rock outcroppings, mature woodland which hasn't been logged in over 50 years, a fully equipped camper trailer with propane fired generator for off grid living and even a 4 wheeler outfitted with

  John Wetmore Wetmore Real Estate

  0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091
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  /51

  $215,000

  • 2 Beds
  • 1 Bath
  • 892 Sq Ft

  145 Main St Unit 210, Ludlow, VT 05149

  Downtown Ludlow Convenience - Welcome to Mill #210, a beautifully updated condo in the heart of Ludlow. Just minutes to Okemo Mountain and directly on the shuttle route, this furnished unit combines comfort with convenience. Inside, you’ll find exposed beams, modern updates throughout, and an open living space that flows seamlessly to a private deck overlooking the Black River. Enjoy the ease of

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  145 Main St Unit 210, Ludlow, VT 05149
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  /59

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,800 Sq Ft

  248 Gird Lot Rd, Weathersfield, VT 05151

  This meticulously maintained five-bedroom, four-and-a-half-bath home offers sweeping views of the Connecticut River Valley and New Hampshire mountains. Thoughtfully designed for comfort and flexibility, the open-concept layout includes a main-level living option, hardwood floors, and tall ceilings with abundant and expansive windows that flood the home with natural light. The spacious kitchen is

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  248 Gird Lot Rd, Weathersfield, VT 05151
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  /60

  $1,675,000 New Construction

  • 4 Beds
  • 3 Baths
  • 1,884 Sq Ft

  37 Village Center Rd Unit 1, Ludlow, VT 05149

  Welcome to SouthFace Village, Okemo Mountain’s newest slope-side community. This fully furnished, end-unit condo offers the ideal blend of modern comfort and mountain charm, ready for immediate occupancy. With four bedrooms and three bathrooms, this spacious unit boasts natural light and unrivaled access to the slopes, including the on-site Sunshine Quad chairlift for SouthFace owners. Key

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  37 Village Center Rd Unit 1, Ludlow, VT 05149
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  /56

  $3,100,000

  • 5 Beds
  • 4.5 Baths
  • 7,634 Sq Ft

  165 Moonshadow Dr Unit M-15, Ludlow, VT 05149

  Welcome to your mountain sanctuary in the heart of Solitude Village—Okemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great

  Joseph Karl William Raveis Real Estate Vermont Properties

  165 Moonshadow Dr Unit M-15, Ludlow, VT 05149
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  /11

  $149,000

  • Land
  • 3.54 Acres
  • $42,090 per Acre

  00 Carlton Hill Rd Unit 27, Woodstock, VT 05091

  Discover the beauty of Vermont from this diverse 3.5-acre parcel along Carlton Hill Road, set in a peaceful rural location amid a neighborhood of substantial properties. With level access from a well-maintained town road, this land offers an inviting blend of convenience and natural charm. Just minutes from the vibrant shops, dining, and cultural attractions of Woodstock Village, the property

  Sandy Reavill Real Broker LLC

  00 Carlton Hill Rd Unit 27, Woodstock, VT 05091
• 

  

  /26

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,349 Sq Ft

  19 Kettlebrook Rd Unit D-5, Ludlow, VT 05149

  Direct ski-on, ski-off two-bedroom top-floor unit in the Kettlebrook community. Nicely updated throughout. Enclosed mudroom entrance with built-ins, laundry, and exterior ski closet. The main level includes a well-designed kitchen and a separate dining area with a newly installed slider leading out to the deck, which looks out to the slopes; a living room with a wood burning fireplace and

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

  19 Kettlebrook Rd Unit D-5, Ludlow, VT 05149
• 

  

  /58

  $3,150,000

  • 5 Beds
  • 5.5 Baths
  • 3,460 Sq Ft

  48 Alpine Way Unit D-1, Ludlow, VT 05149

  Show Stopper—this five-bedroom slopeside townhouse sits just steps from the trails and offers three private suites across three levels of beautifully curated living space. Completely reimagined by a talented local designer, it features an organic palette, thoughtful details, and a true move-in-ready feel—just hang your artwork and your skis. The chef’s kitchen showcases a Dekton waterfall

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

  48 Alpine Way Unit D-1, Ludlow, VT 05149

Showing Results 81 - 120, Page 3 of 11