Windsor County VT Homes for Sale

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  $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

  • 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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  $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
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  /54

  $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
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  /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
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  /14

  $845,000

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  234 Randall Rd, Wood Stock, VT 05091

  Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm

  Wade Treadway Wade I Treadway Real Estate

  234 Randall Rd, Wood Stock, VT 05091
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  /38

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,423 Sq Ft

  441 Rhoades Hill Rd, Bethel, VT 05032

  Set within the scenic landscape of Barnard, this beautifully updated 3-bedroom, 3-bath home offers the perfect blend of Vermont charm and modern comfort. Surrounded by peaceful countryside and sweeping views, the property invites you to slow down and enjoy every season. Inside, the home is filled with warmth and character, featuring hardwood floors, natural woodwork, exposed beams, and an

  Daniel Preston KW Vermont Woodstock

  441 Rhoades Hill Rd, Bethel, VT 05032
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  /38

  $413,900

  • 4 Beds
  • 2.5 Baths
  • 2,888 Sq Ft

  273 Route 5 N, Windsor, VT 05089

  Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and

  Allison Griep BHHS Verani Upper Valley

  273 Route 5 N, Windsor, VT 05089
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  /6

  $25,000

  • Land
  • 5,662 Sq Ft
  • $192,308 per Acre

  262 Seavers Brook Rd, Springfield, VT 05156

  Don Chabot Town and Country Realty

  262 Seavers Brook Rd, Springfield, VT 05156
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  /4

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 2,334 Sq Ft

  72 Wood Rd, Hartford, VT 05001

  US Route 4 in Vermont - the east/west corridor from I-89 and the Killington Ski Area. Highway frontage between Quechee and Woodstock, VT. Minutes from Dartmouth College in Hanover, NH; near the intersection of I-89 and 91 at the Connecticut River; also close to Northern New England’s major DH Medical complex and Cancer Center in Lebanon, NH, as well as the VA Hospital in White River Junction. 1.5

  Terry Boone Bassette Real Estate Group

  72 Wood Rd, Hartford, VT 05001
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  /47

  $749,000

  • 4 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  36 Lower IV Unit 48B, Ludlow, VT 05149

  This popular Sachem floor plan at the Okemo Trailside community is ready for new owners. Four bedrooms and two and a half baths across three levels, with a very recent remodel. It features a light, bright open floor plan, a beautifully updated kitchen with plenty of counter space and new appliances, a breakfast bar, a dining area with sliders off the deck, and a living room with a cathedral

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

  36 Lower IV Unit 48B, Ludlow, VT 05149
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  /3

  $220,000

  • Land
  • 50.45 Acres
  • $4,361 per Acre

  0 Missing Link Rd, Springfield, VT 05156

  Sitting high above Rte 5, this large parcel has a prime view out over the Connecticut River. There's a septic permit in place for a 5 bedroom home. You'll need to improve the old logging road to gain access to the top but once you do, there are 50 acres to explore. Enroll in the Use Value Program to reduce your taxes!

  Victoria Woods Brattleboro Area Realty

  0 Missing Link Rd, Springfield, VT 05156
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  $589,000

  • 2 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  14 Sterling Springs Dr, White River Junction, VT 05001

  A prize location situated at the top of Sterling Springs Drive with views to the hills. This light filled home has an open floor plan allowing for creative use of spaces. Many features include a generous sized primary bedroom with two walk-in closets, and a recently renovated ensuite bathroom. New flooring was added in a section of the main level. The second floor provides a bedroom and full

  Berna Rexford Four Seasons Sotheby's Int'l Realty

  14 Sterling Springs Dr, White River Junction, VT 05001
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  /16

  $129,900

  • 3 Beds
  • 2 Baths
  • 2,321 Sq Ft

  31 Amsden Hollow Rd, Perkinsville, VT 05151

  Older farmhouse looking for someone to bring it back to what it once was currently has 3-4 bedrooms, two baths, two kitchens, level lot, shed in the front yard area and a brook in the back yard area.

  April Shepard Twin State Realty LLC

  31 Amsden Hollow Rd, Perkinsville, VT 05151
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  /22

  $1,490,950 New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,709 Sq Ft

  399 Bentley Rd Unit 7-5440, Hartford, VT 05059

  The Evergreen at Mountain Stream — Currently under construction at 399 Bentley Road, the Evergreen offers 2,709 square feet of contemporary living across two finished levels, paired with a detached two-car garage. A long, low silhouette under a standing-seam metal roof, composite board-and-batten siding, and oversized windows give the home a distinctly modern presence — clean architectural lines

  Richard Higgerson Higgerson & Company

  399 Bentley Rd Unit 7-5440, Hartford, VT 05059
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  $569,000

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  3341 Trebo Rd, Chester, VT 05143

  Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end. Step outside to a sunny, open lot with a

  Daire Gibney Barrett and Valley Associates Inc.

  3341 Trebo Rd, Chester, VT 05143
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  /2

  $28,900

  • Land
  • 1.9 Acres
  • $15,211 per Acre

  223 Falcon Loop Rd E, Rochester, VT 05767

  Build your Vermont retreat on this 1.90-acre wooded lot in thedesirable Great Hawk community in Rochester. Surrounded by natural beauty, this property offers a peaceful setting with access to hiking, skiing, and year-round outdoor recreation, plus nearby attractions like the Green Mountain National Forest and scenic Route 100. Rochester is loved for its quiet charm, local farms, and

  Derek Greene Derek Greene

  223 Falcon Loop Rd E, Rochester, VT 05767
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  /6

  $175,000

  • Land
  • 1.02 Acres
  • $171,569 per Acre

  Lot 51 Partridge Rd, Ludlow, VT 05149

  1.02+/- acres. Lot 51. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

  Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

  Lot 51 Partridge Rd, Ludlow, VT 05149
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  /13

  $50,000

  • Land
  • 1.5 Acres
  • $33,333 per Acre

  2-63 Goshawk Dr, Plymouth, VT 05056

  Affordable opportunity to build your dream home in a quiet neighborhood located between Okemo and Killington Mountain Resorts, with nearby access to Echo Lake, Hawk Resort hiking trails, and Plymouth State Park. With utilities close by and the ability to connect to the community wastewater system, this lot is ready for your new Vermont home. Community covenants and design standards help protect

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  2-63 Goshawk Dr, Plymouth, VT 05056
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  /48

  $6,750,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 5,087 Sq Ft

  412 Skyland Ln, Woodstock, VT 05091

  Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

  Story Jenks LandVest, Inc/Woodstock

  412 Skyland Ln, Woodstock, VT 05091
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  /2

  $450,000

  • Land
  • 119 Acres
  • $3,782 per Acre

  00 Bradley Hill Rd Unit 121, Norwich, VT 05055

  Unusually large parcel of land in Norwich. 119 +/- ac with over 2500' of road frontage on delightful Bradley Hill Road. Close to town yet calm and quiet. The land abuts conservation land and the "Bradley Hill Loop" - a maintained trail. Not yet in Current Use though the forestry plan is ready to be implemented. A great opportunity to build in the Dresden School District.

  Jane Darrach Martha E. Diebold/Hanover

  00 Bradley Hill Rd Unit 121, Norwich, VT 05055
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  /15

  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  108 Cubb Ct, Windsor, VT 05089

  Welcome to 132 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney 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

  108 Cubb Ct, Windsor, VT 05089
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  $985,000

  • 4 Beds
  • 3 Baths
  • 2,785 Sq Ft

  1782 Randall Rd, Woodstock, VT 05091

  This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

  Wade Treadway Wade I Treadway Real Estate

  1782 Randall Rd, Woodstock, VT 05091
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  /21

  $119,000

  • Land
  • 3.95 Acres
  • $30,127 per Acre

  00 Barber Ln, Hartland, VT 05048

  Discover the ideal backdrop for your next build on this peaceful slice of Vermont countryside. Positioned on a gentle rise, the land offers elevated views and a serene natural setting surrounded by mature landscape. A privately maintained road leads you in, providing a quiet approach and a sense of retreat. This location strikes a perfect balance—rural charm with quick access to daily

  Chelsea Bevis KW Vermont Woodstock

  00 Barber Ln, Hartland, VT 05048
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  /22

  $290,000

  • Land
  • 75 Acres
  • $3,867 per Acre

  1175 Quarry Rd, Chester, VT 05143

  An extraordinary potential homesite set in the hills of southern Vermont. This expansive 75-acre parcel offers the perfect blend of privacy, natural beauty, and endless potential. Whether you dream of building a secluded hilltop retreat or preserving land for recreation and conservation, this property invites endless possibilties. Improvements include a septic system, dug well, electricity and a

  Jessica Samples BHG Masiello Keene

  1175 Quarry Rd, Chester, VT 05143
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  /30

  $135,000

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft

  25 Wilder Ln, Bethel, VT 05032

  Welcome to this spacious 3-bedroom, 2-bath mobile home on .65 acres of owned land in the lovely town of Royalton, Vermont. Built in 1997, this place offers 1,140 square feet of comfortable, single-level living that perfectly blends convenience, affordability, and peaceful tranquility. Nestled on a quiet dead-end road, the home provides great privacy while still being close to local amenities and

  Jeremy Collins Ridgeline Real Estate

  25 Wilder Ln, Bethel, VT 05032
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  $100,000

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

  606/608 QII Jackson Gore Adams House Unit 606/608 QII, Ludlow, VT 05149

  Jackson Gore Village at Okemo Mountain Resort - Welcome to the Adams House at Jackson Gore, where mountainside living meets year-round adventure. This spacious, well-appointed condominium offers comfort and convenience in one of Okemo’s most sought-after slopeside communities. Step inside to find a generous open-concept living space with a cozy gas fireplace, ideal for relaxing after a day on the

  Katherine Burns William Raveis Real Estate Vermont Properties

  606/608 QII Jackson Gore Adams House Unit 606/608 QII, Ludlow, VT 05149
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  /47

  $395,000

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  5798 W Woodstock Rd, Woodstock, VT 05091

  Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors

  Carol Wood Williamson Group Sothebys Intl. Realty

  5798 W Woodstock Rd, Woodstock, VT 05091
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  /40

  $499,500

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  111 E Gilson Ave, White River Junction, VT 05001

  This is the type of property that doesn't come around very often! It is set on 2.5 private acres at the end of the road, abutting Vermont State Forest land. That said, it has terrific walkability to stores, Simon Pearce, the elementary school, Lake Pinneo, nearby hiking trails and Quechee Gorge. It's an easy drive to skiing, shopping in West Lebanon and hospitals. The land features level sunny

  Mary Paino Coldwell Banker LIFESTYLES - Quechee

  111 E Gilson Ave, White River Junction, VT 05001
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  /8

  $275,000

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

  3186 South Rd, Woodstock, VT 05091

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

  Andrew Hubbell Vermont Real Estate Company

  3186 South Rd, Woodstock, VT 05091
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  /21

  $299,000

  • Land
  • 8.1 Acres
  • $36,914 per Acre

  0 Fay Ln Unit 7226 and 7227, Hartford, VT 05059

  Discover the serene beauty of Vermont from this expansive 8.1-acre parcel along Fay Lane! The lot is located in the esteemed Quechee Lakes Landowners Association (QLLA). Quechee Lakes is a private, full-amenity resort with two championship golf courses, a private lake and beach, tennis and pickleball, indoor/outdoor pools, a fitness center, and a racquet sport complex. In winter, enjoy downhill

  Brooks Reavill

  0 Fay Ln Unit 7226 and 7227, Hartford, VT 05059
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  /4

  $130,000

  • 6 Beds
  • 4 Baths
  • 2,304 Sq Ft

  51 Merrill St, Springfield, VT 05156

  What a great opportunity! With a good mix of unit sizes, this would make a great investment property to round out your portfolio, or an owner occupied unit of your choice. Nice location in town with great views, there's some deferred maintenance that will be needed in the near term; but with some smart upgrades it could have great cash flow for the long term.

  Courtney Doubleday EXP Realty

  51 Merrill St, Springfield, VT 05156
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  /27

  $525,000

  • 6 Beds
  • 2 Baths
  • 2,304 Sq Ft

  81 High St, Cavendish, VT 05142

  Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the

  Tyleen Murray Kelley Real Estate, Inc.

  81 High St, Cavendish, VT 05142
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  /60

  $3,250,000

  • 5 Beds
  • 6.5 Baths
  • 5,728 Sq Ft

  191 Moon Shadow Dr Unit M19, Ludlow, VT 05149

  Solitude home at the top of the hill awaits! Solitude on Okemo Mountain, where this exceptional five-bedroom home captures the ultimate ski location, breathtaking long-range views, and unparalleled privacy. Perfectly positioned to embrace the beauty of the surrounding mountains, this residence offers a rare opportunity to enjoy true slope-side living in one of Vermont’s most sought-after resort

  Katherine Burns William Raveis Real Estate Vermont Properties

  191 Moon Shadow Dr Unit M19, Ludlow, VT 05149
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  /16

  $70,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  434 Qtr. I Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn, Unit 434 Q I. Quarter Ownership. This top floor residence has beautiful valley facing views. Unit B Features: one bedroom with king bed, queen sleep sofa and queen wall bed, full kitchen, jetted tub, fireplace, entertainment center. This unit sleeps six and includes 1 locker for year round use. Other features include a large master bath offering his and her sinks, gas fireplace

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

  434 Qtr. I Jackson Gore Inn, Ludlow, VT 05149
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  /2

  $269,000

  • Land
  • 13.9 Acres
  • $19,353 per Acre

  1 Barbara Lee Ln, Norwich, VT 05055

  Tucked off a quiet country lane in desirable Norwich, this 13.9 acre parcel offers a beautiful blend of privacy, convenience, and thoughtfully advanced planning. Just 10 minutes to center village and Dan & Whit’s, the land features a mostly level, roughed-in driveway approach and a peaceful setting ideal for a serene Vermont lifestyle. EC Fiber is available at the road for modern connectivity. A

  Kris Lippi Get Listed Realty

  1 Barbara Lee Ln, Norwich, VT 05055
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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. Extensive work has been done to the road leading to the lot including widening the road and adding culverts and the Seller has roughed in a driveway (Buyer would need to obtain a driveway permit prior

  Tami Sullivan Snyder Donegan Real Estate Group

  00 Chapel Hill Rd, Sharon, VT 05065
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  /50

  $1,245,000

  • 3 Beds
  • 4 Baths
  • 2,971 Sq Ft

  42 Deerfield Dr, Ludlow, VT 05149

  Perched on South Hill with sweeping views of Okemo Mountain, this thoughtfully built home captures everything you want in a Vermont mountain retreat—comfort, quality, and a setting that’s hard to beat. Just minutes from the slopes, downtown Ludlow shopping, and dining, it offers the perfect balance of country feel and everyday convenience. Inside, the layout is open and inviting, designed for

  Kevin Barnes William Raveis Real Estate Vermont Properties

  42 Deerfield Dr, Ludlow, VT 05149
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  /26

  $479,000

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

  85 Townhouse Way Unit 14, Woodstock, VT 05091

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

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  85 Townhouse Way Unit 14, Woodstock, VT 05091
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  /13

  $1,625,000 New Construction

  • 5 Beds
  • 4 Baths
  • 3,837 Sq Ft

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001

  The Aspen at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the 3,079-square-foot Aspen offers three levels of flexible, beautifully appointed living, with a single-bay tuck-under garage and a detached two-car garage. The main level centers on a great room that combines living, dining, and kitchen areas under double-height ceilings, anchored by a fireplace and opening to a

  Richard Higgerson Higgerson & Company

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001

Showing Results 361 - 400, Page 10 of 11