Windsor County VT Homes for Sale

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  /16

  $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
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  /14

  $374,000

  • 3 Beds
  • 2 Baths
  • 1,134 Sq Ft

  32 Route 103 S Unit B5, Ludlow, VT 05149

  Recently refreshed 3BR/2Bath Condo, 5 minutes to Okemo Mountain Resort, 30 minutes to Killington Skyeship. Seasonal swimming pool.

  Robert Balewicz Evergreen Realty of Vermont

  32 Route 103 S Unit B5, Ludlow, VT 05149
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  /60

  $1,200,000

  • 4 Beds
  • 4.5 Baths
  • 4,352 Sq Ft

  884 Bridgewater Center Rd, Bridgewater Corners, VT 05035

  Tucked on 13.68 private acres near the north branch of the Ottauquechee River, this one-owner Bridgewater estate was built from the ground up with uncommon care — and it shows in every detail. With 4,300 square feet of living space (6,700 total), the home is heated by radiant flooring throughout and served by a new furnace/boiler, a private septic system, and a private well known for its

  Tucker Adirondack Lange Lange & Lange

  884 Bridgewater Center Rd, Bridgewater Corners, VT 05035
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  /59

  $14,900,000

  $3M PRICE DROP

  • 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
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  /40

  $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
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  /53

  $1,490,000

  $200K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 5,400 Sq Ft

  1302 Popple Dungeon Rd, Chester, VT 05143

  Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details—wide-plank wood floors, paneled walls,

  Gary Coger Four Seasons Sotheby's Int'l Realty

  1302 Popple Dungeon Rd, Chester, VT 05143
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  /46

  $795,000

  $130K PRICE DROP

  • 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
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  /60

  $495,000

  Open Sat 9:30AM - 11AM

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  3078 Vt Route 10, Chester, VT 05143

  This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached

  Tyleen Murray Kelley Real Estate, Inc.

  3078 Vt Route 10, Chester, VT 05143
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  /29

  $360,000

  New Construction $55K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  696 Vermont Route 100, Ludlow, VT 05149

  LUDLOW: Lake Pauline Waterfront with Existing Footprint and Permit in Place.Opportunity to own a unique lakefront property on Lake Pauline with approximately 600 feet of shoreline and over an acre of land just minutes from Okemo Mountain Resort.The existing home is positioned close to the water within an established footprint that could not be replicated under current regulations. This

  Melissa Loughan Westside Real Estate

  696 Vermont Route 100, Ludlow, VT 05149
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  /10

  $465,000

  $14K PRICE DROP

  • 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
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  /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 mature trees and natural beauty—perfect for building your dream home, creating your own private trail system, or simply enjoying the quiet serenity of the outdoors. Includes a recent topographic and boundary survey, providing valuable insight and a strong starting point for your future plans.

  Heather Ashline BHHS Verani Upper Valley

  0 Jericho St Unit 5062382, Hartford, VT 05001
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  /40

  $1,400,000

  • Land
  • 250.7 Acres
  • $5,584 per Acre

  00 Route 100n, Plymouth, VT 05056

  Imagine owning 250 acres of unspoiled land in Vermont's coveted Lake Region, featuring five separate access points to the crystal-clear waters of Echo Lake. Whether you're envisioning a private family retreat, a recreational paradise, a conservation property, or a future development opportunity, this remarkable offering offers endless possibilities. Miles of established trails wind through the

  Kevin Barnes William Raveis Real Estate Vermont Properties

  00 Route 100n, Plymouth, VT 05056
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  /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
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  /21

  $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
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  /9

  $300,000

  • Land
  • 9.8 Acres
  • $30,612 per Acre

  00 Stagecoach Rd, Norwich, VT 05055

  Discover peace and privacy on this 9-acre wooded lot situated near the end of a quiet private road. This natural haven offers excellent seclusion while remaining just 10 minutes from town amenities. With a mix of hardwood and softwood, the property features a significant stand of hemlock and oak —potentially providing enough timber to build your own custom timber-frame home right from the

  Linda White EXP Realty

  00 Stagecoach Rd, Norwich, VT 05055
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  /22

  $140,000

  • Land
  • 12.9 Acres
  • $10,853 per Acre

  0 Woods Rd W Unit 5081865, Ludlow, VT 05149

  Can't find the right house, nor the right location? This coveted Farm Ridge Lot could solve all your problems. This 12.9 acre lot has various terrain and private wooded views. This lot is on a quiet cul-de-sac named Woods Road West. You can decide how much land to clear - it's begging to have the land opened up to reveal the stunning views that neighboring houses enjoy. The lot was previously

  Joseph Karl William Raveis Real Estate Vermont Properties

  0 Woods Rd W Unit 5081865, Ludlow, VT 05149
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  /35

  $895,000

  • 5 Beds
  • 3.5 Baths
  • 3,631 Sq Ft

  193 Chester Arthur Rd, Hartford, VT 05001

  Perched on 2.7 private acres with a stunning westerly exposure, this exceptional contemporary Cape captures sweeping views of Vermont’s rolling hills, including the slopes of the Quechee Ski Hill. Framed by mature birch trees and towering pines, the setting is both peaceful and picturesque, offering spectacular sunsets and year-round beauty.Designed for comfort and gathering, the home

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  193 Chester Arthur Rd, Hartford, VT 05001
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  /19

  $345,000

  • Land
  • 6.48 Acres
  • $53,241 per Acre

  0 Oakridge Way, Woodstock, VT 05091

  Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires

  Nancy Greenwood Watson Realty & Associates

  0 Oakridge Way, Woodstock, VT 05091
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  /38

  $2,999,000

  • 6 Beds
  • 8 Baths
  • 5,142 Sq Ft

  18 The Green, Woodstock, VT 05091

  Centrally located on the southwest side of the historic Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication and functionality. The first level of

  Danny Kogut Williamson Group Sothebys Intl. Realty

  18 The Green, Woodstock, VT 05091
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  /14

  $1,560,000

  New Construction $65K PRICE INCREASE

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

  4070 Tichenor Rd, Hartford, VT 05059

  The Thistle at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Thistle offers 3,120 square feet of contemporary living across two levels, paired with a single-bay tuck-under garage, separate heated storage with optional rec-room conversion, and a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic

  Richard Higgerson Higgerson & Company

  4070 Tichenor Rd, Hartford, VT 05059
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  /43

  $309,000

  • 3 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  147 Park St, Springfield, VT 05156

  Welcome to 147 Park Street! Situated on a 0.31-acre lot with a fully fenced yard, perennial flower gardens, and attractive landscaping, this home offers plenty of space both inside and out.Full of character and style, this spacious home features a thoughtful floor plan designed for everyday living. The large kitchen includes updated appliances, a generous dining area, and plenty of room for

  Mary Paino Coldwell Banker LIFESTYLES - Quechee

  147 Park St, Springfield, VT 05156
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  /14

  $239,000

  • Land
  • 10.1 Acres
  • $23,663 per Acre

  0 Christian St Unit 5084994, Hartford, VT 05001

  Beautiful, in town location. A very rare opportunity to own an in town Christian Street parcel of land. If you've been having a hard time finding the right home in this very tight housing market Or if you've been dreaming about new construction in the Hartford / Upper Valley area than look no further. This land parcel is conveniently located only minutes from Downtown White River Junction, VT. .

  Alex DeFelice The Clerkin Agency, P.C.

  0 Christian St Unit 5084994, Hartford, VT 05001
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  /56

  $1,395,000

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  683 Reservoir Rd, White River Junction, VT 05001

  Welcome to Trail’s End - an oasis of peace and tranquility suffused with the restorative power of nature. Set amidst lush gardens and rolling lawns, this gorgeous timber frame house blends traditional looks with modern sensibilities and amenities, offering comfortable, light-filled, and highly functional spaces throughout. The beautifully appointed main floor primary bedroom features a spacious

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  683 Reservoir Rd, White River Junction, VT 05001
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  /45

  $1,299,000

  $151K PRICE DROP

  • 8 Beds
  • 5 Baths
  • 3,814 Sq Ft

  7030 U S 4, Bridgewater, VT 05034

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

  Eric Benvenuti

  7030 U S 4, Bridgewater, VT 05034
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  /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
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  /58

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,697 Sq Ft

  1641 W Hill Rd, Rochester, VT 05767

  Welcome to The Birches — a peaceful end-of-road retreat where serenity, privacy, and Vermont’s natural beauty come together. Surrounded by more than 7,000 acres of conserved national forest land, this exceptional property offers unmatched tranquility, abundant wildlife, and direct access to outdoor adventure in every season.Set in a quiet mountain setting, this thoughtfully designed

  Brandon Fowler RE/MAX North Professionals

  1641 W Hill Rd, Rochester, VT 05767
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  /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
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  /34

  $489,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,626 Sq Ft

  3208 Green Mountain Turnpike, Chester, VT 05143

  Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  3208 Green Mountain Turnpike, Chester, VT 05143
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  /12

  $120,000

  • Land
  • 3.24 Acres
  • $37,037 per Acre

  508 Mattson Rd, Chester, VT 05143

  This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded

  Jessica Citera Cummings & Co

  508 Mattson Rd, Chester, VT 05143
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  /48

  $395,000

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft

  38 Northshore Dr, Ludlow, VT 05149

  Lake Rescue Retreat.Embrace the lakeside lifestyle in this quintessential Vermont cottage on Lake Rescue. Nestled on a spacious lot, this property perfectly blends historic character with future opportunity. You can choose to use the existing structure as your ultimate summer escape, remodel it to your exact taste, or build your brand-new dream lakeside home from the ground up.A fully

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

  38 Northshore Dr, Ludlow, VT 05149
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  /58

  $790,000

  $105K PRICE DROP

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

  1607 Massey Rd, Springfield, VT 05156

  MOTIVATED SELLER!!! 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

  Jessica Citera Cummings & Co

  1607 Massey Rd, Springfield, VT 05156
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  /26

  $110,000

  $9K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 240 Sq Ft

  505 Back Mountain Rd Unit 14, Windsor, VT 05089

  This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built

  Jenna Luce RE/MAX Upper Valley

  505 Back Mountain Rd Unit 14, Windsor, VT 05089
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  /40

  $795,000

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

  28 Fowler Rd Unit N103, Ludlow, VT 05149

  Winterplace at Okemo Mountain Resort! Welcome to Unit N103, a beautifully appointed first-floor condominium offering the perfect balance of comfort, convenience, and alpine charm. With 3 spacious bedrooms and 2 bathrooms, this residence features a bright, open-concept layout designed for effortless entertaining and relaxing after a day on the slopes. Enjoy true slopeside access with direct entry

  Katherine Burns William Raveis Real Estate Vermont Properties

  28 Fowler Rd Unit N103, Ludlow, VT 05149
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  /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
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  /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
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  /60

  $835,000

  $20K PRICE DROP

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

  233 Okemo Trailside Extension Unit 45A, Ludlow, VT 05149

  Trailside on Okemo Mountain. Experience mountain living at its finest in this spacious 4-bedroom, 3-bathroom condo on Okemo Mountain, perfectly positioned at the top of the complex with enormous easterly views toward Ascutney Mountain. The entire unit has been completely renovated, including sliders and windows! Enter through a welcoming mudroom—ideal for ski gear and all four seasons—before

  Joseph Karl William Raveis Real Estate Vermont Properties

  233 Okemo Trailside Extension Unit 45A, Ludlow, VT 05149
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  /24

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft

  37 Dee Haven, Sharon, VT 05065

  Looking to start your investment portfolio? This property is a great place to start. In a quiet Sharon cul-de-sac, this property has two 2-bedroom units, one on each floor. Newer roof, newer shared septic, poured concrete foundation. The lot includes 10.5 acres of land, majority of which abuts land owned by the Vermont Department of Fish & Wildlife, which connects to the White River.

  Devin Josler Black House Real Estate

  37 Dee Haven, Sharon, VT 05065
• 

  

  /60

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 4,111 Sq Ft

  39 Wallis View Ln, Ludlow, VT 05149

  Set in the highly desirable South Hill Estates, this exceptional property pairs privacy with an unbeatable location just minutes from Okemo Mountain. Surrounded by nearly five acres, the home enjoys sweeping mountain views and a beautifully open landscape that invites year-round enjoyment. The yard is a true highlight—offering plenty of space to relax, entertain, and play. A picturesque pond

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  39 Wallis View Ln, Ludlow, VT 05149
• 

  

  /60

  $625,000

  $25K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,482 Sq Ft

  33 Acorn St, White River Junction, VT 05001

  Set in a peaceful neighborhood with scenic views and large backyard, this expansive home offers the perfect balance of space, comfort, and flexibility. With 5 bedrooms and several bonus living areas throughout, there is plenty of room to fit a variety of lifestyles and needs. Inside, you’ll find spacious living areas filled with natural light, along with a finished basement that adds even more

  The Malley Group KW Vermont

  33 Acorn St, White River Junction, VT 05001
• 

  

  /60

  $3,350,000

  • 5 Beds
  • 5 Baths
  • 3,212 Sq Ft

  166 Jewett Rd, Brownsville, VT 05037

  Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

  Dana Waters Dark Horse Realty

  166 Jewett Rd, Brownsville, VT 05037

Showing Results 361 - 400, Page 10 of 12