Windsor County VT Homes for Sale

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  /60

  $1,450,000

  • 6 Beds
  • 5.5 Baths
  • 4,225 Sq Ft

  515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062

  Nestled in the tranquil hills of West Windsor, Vermont, Rock Haven Estate is a remarkable 33.49-acre country sanctuary offering three separate luxury homes, set along a private drive & surrounded by nature’s beauty. Whether you're looking for a full-time residence with income-generating opportunities or a private family compound, Rock Haven Estate is a rare find! The Rock House - Hilltop Elegance

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  515 Shattuck Hill Rd Unit 515, 513 & 511, Reading, VT 05062
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  /47

  $625,000

  • 2 Beds
  • 3 Baths
  • 1,369 Sq Ft

  193 Jackson Gore Unit 640/642, Ludlow, VT 05149

  Bixby House 640/642 Whole Ownership. This luxury two-bedroom, valley side home features fully-equipped kitchen with stainless steel appliances, tiled back splash, farm sink and granite counters. The cozy living room includes a dining area and gas fireplace. The tiled foyer entry provides storage for outdoor gear. Primary bedroom has a king bed and a spacious master bath with his and her sinks.

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

  193 Jackson Gore Unit 640/642, Ludlow, VT 05149
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  /44

  $95,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149

  Jackson Gore on Okemo Mountain with this slopeside two-bedroom, two-bathroom corner condominium offering spectacular valley views. Thoughtfully designed for comfort and convenience, this residence features a open-concept living room with a gas fireplace, dining area, and a fully equipped kitchen—perfect for relaxing after a day on the mountain. The primary bedroom offers a king bed, while the

  Joseph Karl William Raveis Real Estate Vermont Properties

  238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149
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  /42

  $3,500,000

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

  18 The Green, Woodstock, VT 05091

  Conveniently located on the southwest side of the picturesque 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, functionality, modern comfort

  Danny Kogut Williamson Group Sothebys Intl. Realty

  18 The Green, Woodstock, VT 05091
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  /58

  $695,000

  • 6 Beds
  • 7 Baths
  • 3,880 Sq Ft

  815 Vermont Route 100, Weston, VT 05161

  Escape to this enchanting circa 1830 Colonial, a quintessential Vermont country retreat perfectly positioned at the edge of Weston Village with breathtaking Green Mountain views. Embrace the beauty of nature with nearby XC ski trails, snowmobiling, and snowshoeing, plus five renowned ski mountains just a short drive away. In summer, Weston comes alive with concerts on the village green, summer

  Lee Brown Four Seasons Sotheby's Int'l Realty

  815 Vermont Route 100, Weston, VT 05161
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  /25

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,800 Sq Ft

  50 Bates Rd, Cavendish, VT 05142

  Bring your vision to this charming 3-bedroom, 1-bath farmhouse in the heart of Cavendish, a true opportunity for those looking to restore or reimagine a home with character. Set on a generous 1.6-acre lot, the property offers endless potential with plenty of space to expand, garden, or create your dream outdoor retreat. Inside, you’ll find original hardwood floors throughout and good bones that

  Daniel Preston KW Vermont Woodstock

  50 Bates Rd, Cavendish, VT 05142
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  /10

  $45,000

  • Land
  • 5.6 Acres
  • $8,036 per Acre

  0 Va Cutoff Rd, Hartford, VT 05001

  A unique property for imaginative business owners with commercial or industrial uses in mind. The property is a narrow strip in between I-89 and the Hartford Fire Department, very close to the VA Hospital, where both town water and sewer are available. The southern 3.5 acres (approximately) are covered by class 3 wetlands and cannot be used. The remaining 2 acres also have wet areas, however

  David White OwnerEntry.com

  0 Va Cutoff Rd, Hartford, VT 05001
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  /18

  $235,995

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft

  2359 Vermont 107, Bethel, VT 05032

  Charming 2-Bedroom, 1 - "Office" VT Route 107 Home — High Ceilings, Hardwood Floors, Garage with Office, and Prime Location Just minutes from Exit 3, this versatile Royalton property blends comfort, convenience, and flexibility—perfect for home living, a small business, or both. Bright, Spacious Living – Soaring high ceilings and beautiful hardwood floors create a warm, open, and inviting

  Nathan Wright Century 21 The One

  2359 Vermont 107, Bethel, VT 05032
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  /49

  $675,000

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

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

  Welcome to Trailside 15-C. This recently renovated condo is ready for the next loving family. The natural light filled well appointed condo is turn key and just steps from the slopes. Step into the spacious mudroom with ample hooks, and cubbies to store your gear neatly and a live edge bench to put on your boots. You'll feel right at home when you walk into the light filled open living concept. A

  Frank Provance Diamond Realty

  97 Okemo Trailside Extension Unit 15 C, Ludlow, VT 05149
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  /60

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 5,000 Sq Ft

  2706 E Woodstock Rd, Woodstock, VT 05091

  INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, café, or retail store), Post Office (with current

  John Bassette Bassette Real Estate Group

  2706 E Woodstock Rd, Woodstock, VT 05091
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  /2

  $168,000

  • Land
  • 56.9 Acres
  • $2,953 per Acre

  0 Gird Lot Rd Unit 5066640, 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. Subject to to right of first refusal. Currently going

  John MacGovern Dark Horse Realty

  0 Gird Lot Rd Unit 5066640, Weathersfield, VT 05030
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  /19

  $825,000

  • Land
  • 0.9 Acre
  • $916,667 per Acre

  1049 N Main St, Hartford, VT 05001

  Among last of retail sites at this high demand and very limited commercial zoned properties at this intersection of I-89 and I-91. Just off ramp, visible to travelers at exit. Adjacent to new roundabout. Frontage on I-91 northbound. (sign restrictions to 25ft height, 150 sf). Underserved market for highway travelers into VT & NH. 40,000 VPD combined for I-89 and I-91. 10,000 VPD curbside. Lack of

  James Ward GRI Equity Group Real Estate Broker Inc.

  1049 N Main St, Hartford, VT 05001
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  /21

  $15,000

  • Land
  • 1.05 Acres
  • $14,286 per Acre

  0 Vermont Route 100, Plymouth, VT 05056

  Discover one of the most affordable ways to get into the Hawk Mountain Resort community. This parcel is located off scenic byway Route 100 and is only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and permits must be approved by the Hawk Architectural Review Board. No trailers, yurts, RV's

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Vermont Route 100, Plymouth, VT 05056
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  /45

  $519,000

  • 3 Beds
  • 3 Baths
  • 2,736 Sq Ft

  185 Beans Bridge Rd, Rochester, VT 05767

  Set on three peaceful acres just minutes from the historic village of Rochester, this expanded ranch offers generous living space in a lovely private setting. Amble past a historic farm along a quiet country road to the inviting homesite, perched above the White River valley. The sunny, level lot provides an ideal backdrop for gardening, recreation, and outdoor gatherings. Inside, a large open

  Kyle Kershner Killington Pico Realty

  185 Beans Bridge Rd, Rochester, VT 05767
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  /9

  $175,000

  • Land
  • 5.01 Acres
  • $34,930 per Acre

  476 Missing Link Rd, Springfield, VT 05156

  5 acres of magical Ct River frontage. This site boasts 2 wide open fields. The septic design for a 5 bdrm septic is in the first field. The seller has obtained permission from the state for a driveway curb cut (Missing Link Rd, is State Rte 5) The land sits 80 ft above the river, so flooding is not an issue but you'll have the most peaceful, private views of the water. There are 2 steep walking

  Victoria Woods Brattleboro Area Realty

  476 Missing Link Rd, Springfield, VT 05156
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  /42

  $749,000

  • 3 Beds
  • 1.5 Baths
  • 1,938 Sq Ft

  4205 Vt Route 131, Perkinsville, VT 05151

  Step into timeless New England charm with this historic circa 1760's expanded Cape, offering a great blend of early craftsmanship and character. The home showcases classic timber-frame construction with hand-hewn beams, beautiful plank floors, and period details that create warmth and authenticity throughout. With three bedrooms and two full bathrooms the layout includes a highly desirable first

  Thaddeus Abare Barrett and Valley Associates Inc.

  4205 Vt Route 131, Perkinsville, VT 05151
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  /34

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  842 Main St, Proctorsville, VT 05153

  This property must be seen in person to be appreciated and is not a drive by. Very clean and move-in ready Vermont 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on .26± acres features a new roof and combines comfort and convenience in one of the most desirable areas

  Geralyn Donohue Engel & Völkers Okemo

  842 Main St, Proctorsville, VT 05153
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  /57

  $795,000

  • 5 Beds
  • 2 Baths
  • 2,500 Sq Ft

  1312 MacIntosh Hill Rd, Randolph, VT 05060

  Now offered at $795,000 – A Vermont farmhouse with a historic orchard, mountain views, and income potential. Set amid rolling hills and breathtaking mountain vistas, this classic Vermont farmhouse sits on one of the first Macintosh apple orchards in the country. Rich with history and surrounded by natural beauty, the property offers a rare blend of character, comfort, and opportunity. A

  Jason Saphire www.HomeZu.com

  1312 MacIntosh Hill Rd, Randolph, VT 05060
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  /18

  $50,000

  • Land
  • 2.07 Acres
  • $24,155 per Acre

  0 E Ash Rd, Plymouth, VT 05056

  Welcome to Hawk East lot 2-20. This 2.07 acres lot is one of the closest lots to the Hawk Mountain Resort. There is a nice level area in the middle of the property that would make a nice building site. Easy access to Route 100 and only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 E Ash Rd, Plymouth, VT 05056
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  /46

  $1,425,000

  • 5 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  4946 South Rd, South Woodstock, VT 05071

  Iconic 1854 Gothic Revival home, known as the Lilac Cottage is located in the heart of South Woodstock Village, just a short stroll to The Ransom Tavern at Kedron Valley Inn, The South Woodstock Store, and Kedron Pond. Many new state of the art updates and improvements throughout this versatile, turn-key home, all honoring and highlighting the period detail. The rooms are spacious, bright and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  4946 South Rd, South Woodstock, VT 05071
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  /9

  $249,000

  • 8 Beds
  • 4 Baths
  • 3,312 Sq Ft

  715 Giddings St, Springfield, VT 05150

  This Unique property features a large 3 unit building all featuring 2 bedrooms and 1 bathroom, with an additional carriage house with 2 bedrooms and 1 bathroom aswell. With a new heating system replaced in 2023 and many other key updates.

  Thaddeus Abare Barrett and Valley Associates Inc.

  715 Giddings St, Springfield, VT 05150
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  /43

  $445,000

  • 3 Beds
  • 3 Baths
  • 1,918 Sq Ft

  11 Blueberry Ledge Ridge Unit L3, Plymouth, VT 05056

  Ledges 3--This updated 3-bedroom, 3-bath townhouse offers a welcoming retreat in the lakes region, midway between Killington and Okemo. Renovated in 2013, the home features a stylish kitchen with new cabinetry, quartz countertops, tiled backsplash, cork flooring, and quality appliances including a gas range. The main level is warm and inviting with random-width pine floors and a wood-burning

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  11 Blueberry Ledge Ridge Unit L3, Plymouth, VT 05056
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  /36

  $129,000

  • 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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  /45

  $924,900

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

  307 Remick Rd, White River Junction, VT 05001

  Nestled at the end of a quiet dead-end road, this 14.2 acre private homestead offers exceptional privacy, timeless New England charm, and direct access to over 560 acres of town-owned land—the Hurricane Forest and Wildlife Refuge. This property is a rare blend of seclusion, natural beauty, and convenience—a one mile drive to the intersection of RT 89 and 91, just 20 minutes from Woodstock and

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  307 Remick Rd, White River Junction, VT 05001
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  /19

  $695,000

  • Land
  • 60.57 Acres
  • $11,474 per Acre

  0 Noah Wood Rd, Woodstock, VT 05071

  Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

  Dan Noble Snyder Donegan Real Estate Group

  0 Noah Wood Rd, Woodstock, VT 05071
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  /11

  $39,999

  • Land
  • 1 Acre
  • $39,999 per Acre

  341 Seavers Brook Rd, Springfield, VT 05156

  Easy building lot in a nice neighborhood in Springfield. Near the road roughly half of the property is flat with some clearing. This was actually a former home site, however the building was lost in a fire. Beyond the flat area (about 90 feet in) the topography rises up steeply and it would be difficult to build beyond this point. There is an old septic system on the property however it would

  David White OwnerEntry.com

  341 Seavers Brook Rd, Springfield, VT 05156
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  /7

  $249,000

  • 7 Beds
  • 4 Baths
  • 3,294 Sq Ft

  57 River St, Springfield, VT 05156

  This great property has a great central location in walking distance to downtown Springfield featuring all of the local amenities. The property overlooks the Black River and with good maintenance history on all systems this has the potential to be a great investment.

  Thaddeus Abare Barrett and Valley Associates Inc.

  57 River St, Springfield, VT 05156
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  /30

  $375,000

  • 1 Bed
  • 1 Bath
  • 884 Sq Ft

  162 Okemo Trailside Extension Unit 22C-L, Ludlow, VT 05149

  Okemo Trailside 22-CL is a spacious one-bedroom with a bunk room, ideally located just a minute's walk from the Upper Sachem Trail. This ski-in/ski-out condo, which has seen significant renovations, offers flat, easy access to the slopes and community amenities. Inside, you'll find an open 884-square-foot layout. The entry features a mudroom with rustic pine accents, perfect for storing gear. The

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

  162 Okemo Trailside Extension Unit 22C-L, Ludlow, VT 05149
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  /25

  $1,465,950 New Construction

  • 4 Beds
  • 3 Baths
  • 2,709 Sq Ft

  470 Bentley Rd Unit 7-5443, Hartford, VT 05059

  Mountain Stream at Quechee Lakes seamlessly integrates new construction with the natural beauty of Vermont's premier four-season resort community. Offering over 200 homesites and five distinct home styles, Mountain Stream’s residences feature modern, open layouts, abundant natural light, and soaring ceilings. The exclusive designs establish a commitment to sustainable, energy-efficient living

  Richard Higgerson Higgerson & Company

  470 Bentley Rd Unit 7-5443, Hartford, VT 05059
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  /7

  $54,900

  • Land
  • 29 Acres
  • $1,893 per Acre

  0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464

  These 29 acres, per PVA map, are located in southern Magoffin County in Royalton, Kentucky, with the acreage running along both sides of RT 7. The property is located in the Salt Lick area outside Royalton and includes property on both sides of Salt Lick Road as well. The property is undeveloped but electric and public water are available. For those with visions of homesteading, the Licking River

  Doug Wireman First Choice Realty & Assoc.

  0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464
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  /54

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  405 Soaring Hawk Rd, Plymouth, VT 05056

  Tucked into the beautiful mountains of Vermont, this charming three-bedroom home in Hawk Resort offers a peaceful retreat surrounded by nature. Travel up a country road to find this inviting home nestled among the trees, complete with a detached single-car garage with bonus storage space. Step onto the spacious front deck or relax on the covered screened-in porch, perfect for enjoying the quiet

  Kevin Barnes William Raveis Real Estate Vermont Properties

  405 Soaring Hawk Rd, Plymouth, VT 05056
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  /60

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,658 Sq Ft

  141 Upper Crossroad, Ludlow, VT 05149

  Welcome to Okemo's iconic roundhouse. While not completely round, this distinctive home is only about 1,200' from the main base area - an easy walk even in ski boots. It is all about location! You will find 3+ bedrooms, 2 full baths, a sauna, and hardwood floors in the common areas. The wrap-around deck provides views of Okemo ski trails and is great for outdoor entertaining. The mudroom has a

  Kevin Barnes William Raveis Real Estate Vermont Properties

  141 Upper Crossroad, Ludlow, VT 05149
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  /19

  $224,000

  • Land
  • 68.5 Acres
  • $3,270 per Acre

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156

  Behold this rare opportunity to own 68 acres of pristine Vermont land located on a quiet, town-maintained dirt road in the peaceful hills of Springfield. This expansive parcel is a dream for outdoor enthusiasts—offering direct access to nature with miles of established trails, a diverse and healthy forest, and abundant wildlife.Bordering the beloved Muckross State Park—over 200 acres of

  Daire Gibney Barrett and Valley Associates Inc.

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156
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  /37

  $529,000

  • 5 Beds
  • 5 Baths
  • 3,880 Sq Ft

  514 1st Ave, Chester, VT 05143

  Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals,

  Daire Gibney Barrett and Valley Associates Inc.

  514 1st Ave, Chester, VT 05143
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  /60

  $4,850,000

  • 5 Beds
  • 6 Baths
  • 9,153 Sq Ft

  476 Salt Ash Rd, Plymouth, VT 05056

  Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondacks, known as The Point, and thoughtfully designed to reflect its inviting look and warm, rustic elegance. This 9,000+ square foot residence sits atop a knoll beside a lively creek with small waterfalls, creating a peaceful, natural soundtrack.The Great Room is the centerpiece of the home, with a soaring

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  476 Salt Ash Rd, Plymouth, VT 05056
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  /16

  $400,000

  • Land
  • 13.94 Acres
  • $28,694 per Acre

  0 Gill Terrace Unit 5050286, Ludlow, VT 05149

  In Ludlow Village! 13+ acre wooded lot boasts a direct view of Okemo Mountain! Power and shared driveway on the lot. Old ATV trails run through. Some seasonal drainages but mostly rolling, walkable terrain. It drops off severely on the west side above the cemmetary. A simple WALKING TRAIL FROM the DRIVEWAY on the right follows "dotted flagging" and gets one into the best areas of the land. The

  Don Eatmon Kelley Real Estate, Inc.

  0 Gill Terrace Unit 5050286, Ludlow, VT 05149
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  /33

  $69,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  318/320 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Welcome to this 1 BR lockout with a secluded, private and wooded view with a slight glimpse of the pool off your deck! This unit is located in the south wing with close proximity to the outdoor pool and owners lockers. Unit C Features: 1 bedroom, sleeps eight, lock-out capabilities, 2 fixed Queen beds, Queen sleep sofa, Queen wall bed, full kitchen, 2 full bathrooms, jetted bath tub, fireplace,

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

  318/320 Qtr I Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /25

  $899,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  3773 Woodstock Rd, White River Junction, VT 05001

  **Sales Price includes MLS#5072395 & MLS#5072396 Spacious 3-bedroom single-family home with an additional office/laundry room, 1.5 baths, and 1,296 sq. ft. of living space. Features include a heated enclosed porch, two-car garage, and a private backyard. Situated on a .65± acre property with excellent Route 4 frontage and visibility, just seconds to Interstate 89. The sale also includes a 3,020

  Cheryl Herrmann RE/MAX Group One Realtors

  3773 Woodstock Rd, White River Junction, VT 05001
• 

  

  /30

  $650,000

  • 3 Beds
  • 3 Baths
  • 4,324 Sq Ft

  3630 Vt Route 103 N, Chester, VT 05143

  Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3630 Vt Route 103 N, Chester, VT 05143
• 

  

  /43

  $565,000

  • 5 Beds
  • 3 Baths
  • 2,400 Sq Ft

  68 Passumpsic Ave, Hartford, VT 05047

  This lovely colonial has 5 bedrooms, 3 baths and overlooks the beautiful Connecticut River. Featuring hardwood floors downstairs, a 2-way propane fireplace in the living room and dining room, plus beautiful new carpet throughout the upstairs 4 bedrooms. There is a ground floor bedroom and full bath with the second floor featuring 4 more bedrooms and 2 full baths. The detached garage/barn has

  Nan Carroll Coldwell Banker LIFESTYLES - Hanover

  68 Passumpsic Ave, Hartford, VT 05047

Showing Results 281 - 320, Page 8 of 11