Windsor County VT Homes for Sale

• 

  

  

  /12

  $1,495,000

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

  4070 Tichnor Rd Unit 4070, Hartford, VT 05001

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  4070 Tichnor Rd Unit 4070, Hartford, VT 05001
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  /10

  $1,625,000

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

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001
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  /33

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,446 Sq Ft

  158 MacIntosh Hill Rd, Randolph, VT 05060

  Charming 1820's antique farmhouse with handcrafted cabinets and wide board floors. The home has updated systems including Viessmann on demand water heater, holding tank, pressure tank, newer electrical. Fabulous upgraded bathroom. There is a space of many uses that could be a studio, master suite, in law/guest suite. Also the most lovely screened in back sitting porch overlooking the pastures.

  Sherri McPhetres Vermont Heritage Real Estate

  158 MacIntosh Hill Rd, Randolph, VT 05060
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  /33

  $1,900,000

  • 2 Beds
  • 2.5 Baths
  • 2,944 Sq Ft

  2394 Fletcher Hill Rd, Woodstock, VT 05091

  Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

  John Snyder Snyder Donegan Real Estate Group

  2394 Fletcher Hill Rd, Woodstock, VT 05091
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  /52

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,177 Sq Ft

  166 Woods Rd W, Ludlow, VT 05149

  Perched high on the hillside, this home offers expansive views of the lakes and mountains. Located at the end of a quiet road in the Farm Ridge Community just under 5 miles from the base of Okemo Mountain and 4 miles to Plymouth State Park for boating and swimming in the warmer months. The maintained trails on it's 16.15 acres makes it easy to explore, while the deck is a perfect place to relax,

  Jessica Citera Cummings & Co

  166 Woods Rd W, Ludlow, VT 05149
• 

  

  /36

  $139,000

  • 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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  /18

  $199,000

  • 1 Bed
  • 1 Bath
  • 708 Sq Ft

  221A Southridge St, Springfield, VT 05156

  This sweet little bungalow is a true work in progress — and it’s almost ready to welcome its next owner! Whether you’re searching for your very first home, looking to downsize, or dreaming of a Vermont retreat, this property is full of charm and possibility. Thoughtful updates are well underway, including a new roof, electrical, plumbing, heating, insulation, windows, flooring, and sheetrock, so

  Linda Benoit Highland Realty

  221A Southridge St, Springfield, VT 05156
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  /37

  $585,000

  • 4 Beds
  • 4 Baths
  • 3,934 Sq Ft

  46 Runnals Rd, White River Junction, VT 05001

  Step into timeless character and modern comfort in this unique 4-bedroom, 4-bathroom home. A thoughtful 1984 expansion preserved the original home's historic core featuring a rare early American beehive oven and three-hearth fireplace, while adding over 3,200 sq. ft. of spacious living and a 1,000 sq. ft. in-law apartment. There’s room for everyone here. The sun-drenched kitchen and dining area

  Cheryl Herrmann RE/MAX Group One Realtors

  46 Runnals Rd, White River Junction, VT 05001
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  /60

  $869,000

  • 5 Beds
  • 5 Baths
  • 3,886 Sq Ft

  3961 Hartland Hill Rd, Woodstock, VT 05091

  This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a

  Tambrey Vutech KW Vermont Woodstock

  3961 Hartland Hill Rd, Woodstock, VT 05091
• 

  

  /21

  $110,000

  • Land
  • 1.13 Acres
  • $97,345 per Acre

  00 Evergreen Acres, Ludlow, VT 05149

  Located just 3.5 miles from Okemo Mountain, this prime parcel offers endless potential for your dream home. With selective clearing, enjoy breathtaking views of Okemo Mountain. The property comes with an existing Vermont Wastewater permit for a 3-bedroom residence, making it ready for your plans. Whether you're looking to build your perfect retreat or a year-round residence, this location is

  Kevin Barnes William Raveis Real Estate Vermont Properties

  00 Evergreen Acres, Ludlow, VT 05149
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  /33

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 1,555 Sq Ft

  35 Mountain Ave, Woodstock, VT 05091

  Prime In-Village location on Mountain Avenue just steps to Faulkner Park, The Mt Tom trail system and Woodstock Rec Center. This classic New England duplex (eastern side) home serves perfectly as a full time residence, or an easy keep as a second home. Through a classic covered porch enter the foyer with gleaming hardwood floors and high ceilings. The spacious living room has a propane stove, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  35 Mountain Ave, Woodstock, VT 05091
• 

  

  /22

  $279,000

  • Land
  • 10.2 Acres
  • $27,353 per Acre

  00 Parker Ln, Weston, VT 05161

  Great 10.2 Acre Building Lot with state approved 5 bedroom septic! Ready to bring your vision to life - this property has already had the hard work done for you and features a large 4 acre newly created meadow with spring fed pond. Architectural renderings of a potential home design are available to help you imagine the possibilities. With southern exposure, views of the Green Mountains, and

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  00 Parker Ln, Weston, VT 05161
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  /12

  $245,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  891 Vermont Route 100, Weston, VT 05161

  Charming and efficient, this 2-bedroom, 1-bath home offers a cozy retreat in the heart of Weston, Vermont. Designed for single-level living and low maintenance, the layout makes the most of its space. The main living area features an open flow between the living room and eat-in kitchen, leading to a deck that is perfect for morning coffee or outdoor grilling. Two bedrooms and a full bath complete

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  891 Vermont Route 100, Weston, VT 05161
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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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  /14

  $69,000

  • Land
  • 1.05 Acres
  • $65,714 per Acre

  Lot 49 Spring St, Stockbridge, VT 05772

  Attractive building lot in the desirable Highwood community. This lot offers potential long-range views and includes sewer rights in the Highwood community sewer system, sufficient for a three-bedroom residence. Architectural review and protective covenants ensure that the quality of life in this small community is always preserved. Highwood is adjacent to the Green Mountain Trail network for

  Kyle Kershner Killington Pico Realty

  Lot 49 Spring St, Stockbridge, VT 05772
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  /50

  $295,000

  • 3 Beds
  • 3 Baths
  • 864 Sq Ft

  143 Vermont Route 100, Ludlow, VT 05149

  Welcome to Miner's Knoll, a 3 bedroom, 2 bath home on .95 +/- acres with large deck overlooking the Jewell Brook with a full size, detached two car garage and paved driveway. This turn key property is being sold with furniture and dishware, utensils, etc. and has been used as a successful short-term rental by previous owner and also occupied as a full-time residence. Vt state approved septic

  Geralyn Donohue Engel & Völkers Okemo

  143 Vermont Route 100, Ludlow, VT 05149
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  /35

  $399,000

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

  60 Fletcher Ln, Hartford, VT 05001

  Why go on vacation when you can live the lifestyle every day?Updated Quechee Lakes home is just a quick 7-minute ride to the clubhouse, with year-round resort living right at your doorstep.Step inside to a new kitchen outfitted with Wolf appliances, an updated above code wiring, complemented by tile and wood flooring, and a partially replaced roof for peace of mind. With a newer on-demand

  Gerry Stark RE/MAX Upper Valley

  60 Fletcher Ln, Hartford, VT 05001
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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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  /58

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,146 Sq Ft

  615 Old County Rd, Cavendish, VT 05142

  In need of the perfect ski cabin just 15 minutes from Okemo Mountain? Set on over ten private acres, this home offers the perfect mix of comfort and country charm. The main living room features cathedral ceilings, a propane stove, and access to the deck with a hot tub—ideal for relaxing after a day on the slopes. The kitchen, finished with Vermont soapstone counters and updated appliances, opens

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  615 Old County Rd, Cavendish, VT 05142
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  /24

  $1,495,000

  • 7 Beds
  • 6 Baths
  • 5,774 Sq Ft

  310 Pierce Hill Rd, West Windsor, VT 05089

  Unique Two-Home Property with Stunning Mountain Views.Discover this exceptional property featuring two connected homes, seamlessly blending contemporary design with functionality. Originally built in 1975 and expanded in 2000, this unique residence offers a total of 7 bedrooms, perfect for multi-generational living or as a rental opportunity.The newer side of the home showcases beautiful

  Gary Coger Four Seasons Sotheby's Int'l Realty

  310 Pierce Hill Rd, West Windsor, VT 05089
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  /8

  $247,000

  • 5 Beds
  • 3 Baths
  • 3,100 Sq Ft

  99 Depot St, Hartford, VT 05001

  Prime investment opportunity in Wilder, one of Hartford’s five thriving villages. This early-1900s multifamily, minutes from Upper Valley amenities, is ready for redevelopment with significant upside potential.The property features three units offering multiple strategies: renovate and lease all for strong cash flow, or occupy one while offsetting costs with rental income. Its location

  Ralph Harvey Listwithfreedom.com

  99 Depot St, Hartford, VT 05001
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  /21

  $145,000

  • Land
  • 22.23 Acres
  • $6,523 per Acre

  918 Lovers Lane Rd, Chester, VT 05143

  Located only 2 miles from the picturesque Chester Green you will encounter this newly created 22 acre building parcel on scenic Lover's Lane. This property consists of a 2 acre meadow ideal for building and a 20 acre woodlot consisting of pine, hemlock, oak and maple for sugaring. Beautiful fieldstone walls border most of the boundary lines. The surveyed parcel has an approved 4 bedroom State

  Alan Gombosi Northland Real Estate

  918 Lovers Lane Rd, Chester, VT 05143
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  /12

  $79,000

  • Land
  • 2.53 Acres
  • $31,225 per Acre

  Lot #4 Meadow Rd, Ludlow, VT 05149

  Private 2.53+/- acre state approved building lot located at the end of a dead-end, private road. Positioned at the south end of Ludlow off East Hill Road, this lot offers easy access to town amenities and the Okemo Ski Area. Possible views of Okemo with clearing.

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

  Lot #4 Meadow Rd, Ludlow, VT 05149
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  /22

  $300,000

  • Land
  • 75 Acres
  • $4,000 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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  /55

  $747,000

  • 6 Beds
  • 5 Baths
  • 3,000 Sq Ft

  221 Grout Rd, Perkinsville, VT 05151

  Price reduced! The VT property that you have been waiting for! 49 acres with mature sugar maples and stone walls, a substantial converted barn and a lovely updated and expanded C. 1790 residence. Former home of the Weathersfield Rod and Gun Club, it has been thoroughly renovated into a grand residence. Five bedrooms and five baths, including a guest space with separate entry. Gracious country

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  221 Grout Rd, Perkinsville, VT 05151
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  /21

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  226 N Main St, Bethel, VT 05032

  This 3-bedroom, 1-bathroom home sits on a manageable .10-acre lot and offers the charm of a classic craftsman style. With upgraded electrical and a new water heater, the home is move-in ready while still leaving room for your finishing touches. It needs a little TLC, but the major systems are already in place. Conveniently located close to shopping, dining, and everyday amenities, a great

  Evan Russell Real Broker LLC

  226 N Main St, Bethel, VT 05032
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  /60

  $210,000

  • 3 Beds
  • 3 Baths
  • 2,011 Sq Ft

  625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149

  Jackson Gore area of Okemo– Adams House Quarter Share Ownership, Unit 625/627 Quarter III. Enjoy slopeside living with mountain views in this three-bedroom, three-bathroom condominium with just over 2000 square feet of living space. Located within The Adams House at Jackson Gore on Okemo, offering direct slope access. Enjoy luxury living with full access to The Spring House, which offers an

  Kevin Barnes William Raveis Real Estate Vermont Properties

  625/627 Q3 Jackson Gore Adams House Unit 625/627 Q3, Ludlow, VT 05149
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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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  /39

  $139,900

  • 2 Beds
  • 3 Baths
  • 1,190 Sq Ft

  225/227 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn 225/227; Quarter II: Great Location with Deck off the living area with spectacular views of Jackson Gore slopes, overlooking the fire pit and courtyard! Two bedroom lockout design with plenty of room sleeping 10. Cozy and Comfortable open concept living, dining and kitchen. The lockout gives you flexibility for renting and privacy. Convenient elevator access to the pool,

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

  225/227 Qtr I Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /19

  $374,900

  • 1 Bed
  • 1 Bath
  • 425 Sq Ft

  1441 Jerusalem Hill, Rochester, VT 05767

  Escape to Serenity: Your Off-Grid Vermont Retreat Awaits...Discover 36.9 acres of pure Vermont bliss at 1441 Jerusalem Hill Rd, Rochester. This unique property offers the ultimate off-grid lifestyle, blending rustic charm with endless possibilities.Imagine waking up in a cozy 1-bed/1-bath cabin (approx. 425 sq ft), nestled amidst nature's embrace. This property offers the potential

  Renae Bouchard KW Vermont

  1441 Jerusalem Hill, Rochester, VT 05767
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  /58

  $550,000

  • 3 Beds
  • 1.5 Baths
  • 1,755 Sq Ft

  2295 Quechee Main St, Hartford, VT 05047

  Charming New Englander in the Heart of Quechee! Owned by the same family for more than 30 years, this classic New Englander is set on a spacious double lot in Quechee’s Historic Mill District. The home offers practical living spaces inside, while outside you’ll find ample room for gardening, play, or simply relaxing by the shade trees and small water feature. Being sold “As Is,” this is a

  Jill Harlow Coldwell Banker LIFESTYLES - Hanover

  2295 Quechee Main St, Hartford, VT 05047
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  /55

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  3619 Baltimore Rd, Chester, VT 05143

  5 Minutes from North Springfield and 22 minutes to Ludlow sits the peaceful hamlet of Baltimore, VT. Within the town is a 6 acre lot complimented with fruit trees, a stream, and an ample barn/garage with some roughly finished area above perfect for overflow guests, a home based business or perhaps even additional living space as your needs grow. There's also a storage shed! The house is sizable

  Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

  3619 Baltimore Rd, Chester, VT 05143
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  /25

  $207,000

  • 3 Beds
  • 3 Baths
  • 1,604 Sq Ft

  295 Hotel Rd Unit 10/10A, Brownsville, VT 05037

  This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the property.This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including mountain biking, hiking, cross-country skiing,

  Allison Griep KW Vermont Woodstock

  295 Hotel Rd Unit 10/10A, Brownsville, VT 05037
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  /28

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  25 Felton Rd, Weston, VT 05161

  Beautiful Weston! Just 2 miles from the town center, this 3 Bedroom, 2 Bath Ranch style home on 1.5 Acres offers easy access, just off Route 100, with single level living. Enter into a large Sunroom surrounded with windows, giving the feeling of being outdoors year round and enjoy the wonderful Pellet stove. The eat-in Kitchen, with granite counter tops, offers plenty of cabinet space. The

  Brian Gehlich RE/MAX Four Seasons

  25 Felton Rd, Weston, VT 05161
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  /38

  $1,995,000

  • 4 Beds
  • 5 Baths
  • 3,500 Sq Ft

  2391 Music Mountain Rd, Stockbridge, VT 05772

  TIMBERS IN THE SKY – Featured in Log and Timber Home Living magazine, this one-of-a-kind Vermont timber frame retreat, built in 2022, blends dramatic architecture with refined comfort. Fully furnished with luxury pieces, the open floor plan showcases a soaring great room with vaulted ceilings, walls of glass framing breathtaking mountain views, exposed beams, and a striking tile gas fireplace.

  Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

  2391 Music Mountain Rd, Stockbridge, VT 05772
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  /60

  $1,325,000

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

  332 Cushing Rd, Hartford, VT 05001

  Perched at 1,700 feet on 40 private acres, this Vermont retreat captures sweeping views across the Connecticut River Valley to New Hampshire’s Presidential Range. Despite its sense of seclusion, it’s only minutes to Quechee Village, Woodstock, and Dartmouth College in Hanover.Part of a 10-home association, the property includes access to 52 acres of meadows, woodlands, and a spring-fed

  Keri Cole Williamson Group Sothebys Intl. Realty

  332 Cushing Rd, 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
• 

  

  /5

  $75,000

  • Land
  • 0.5 Acre
  • $150,000 per Acre

  1015 Maple St, White River Junction, VT 05001

  Nice IN-town building lot! Don't miss this opportunity to build a home, business or garage / storage space along Route 14 / Maple Street. Situated just above the White River and Watson Park in Hartford village! This .50+/- acre in town lot has town water, sewer and power available at the street. Just minutes to I 89 & I 91, Dartmouth College, Dartmouth Hitchcock Medical Center, the VA Hospital,

  Alex DeFelice The Clerkin Agency, P.C.

  1015 Maple St, White River Junction, VT 05001
• 

  

  /40

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 3,089 Sq Ft

  16 Church St, Woodstock, VT 05091

  16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village,

  John Snyder Snyder Donegan Real Estate Group

  16 Church St, Woodstock, VT 05091
• 

  

  /27

  $500,000

  • Land
  • 0.94 Acre
  • $531,915 per Acre

  M-17 Moonshadow Dr, Ludlow, VT 05149

  Solitude Village on Okemo Mountain - a fantastic building lot located on Okemo Mountain, within one of its most desirable communities. This is one of the last remaining lots available, offering the unique opportunity to build your dream home in the tranquil Solitude Village. The property boasts direct ski-to-door access, and you can easily walk down to the community pool. Rest assured, the

  Katherine Burns William Raveis Real Estate Vermont Properties

  M-17 Moonshadow Dr, Ludlow, VT 05149

Showing Results 201 - 240, Page 6 of 13