Windsor County VT Homes for Sale

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  /42

  $1,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft

  513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091

  This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chef’s kitchen and den. New Thor stainless steel 48" propane range installed October 2025.Privately set on over 8 acres, the property

  Chris Crowe Quechee Lakes Real Estate Center

  513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
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  /42

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  1079 Fletcher Hill Rd, Woodstock, VT 05071

  This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main living/dining area with a kitchen, all within a rural setting with ample natural light, local views, and a deck. Recent updates include a primary bedroom ensuite featuring a custom walk-in shower and double sinks, new flooring, a

  Terry Davis Williamson Group Sothebys Intl. Realty

  1079 Fletcher Hill Rd, Woodstock, VT 05071
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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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  /37

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,092 Sq Ft

  1782 Blackmer Blvd, Stockbridge, VT 05772

  Nestled on 18 private acres along picturesque Blackmer Boulevard, this traditional log home offers the perfect blend of rustic charm and modern comfort. The open floor plan features soaring vaulted ceilings, a classic woodstove for cozy winter nights, and a spacious kitchen with a gleaming live-edge breakfast bar and updated hickory cabinetry. The loft-style primary bedroom overlooks the main

  Kyle Kershner Killington Pico Realty

  1782 Blackmer Blvd, Stockbridge, VT 05772
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  /56

  $399,000

  • 4 Beds
  • 2 Baths
  • 2,554 Sq Ft

  1806 Vermont Route 100, Rochester, VT 05767

  This historic cape, circa 1785, is one of the oldest homes in Rochester, VT, blending timeless charm with modern updates. Centrally located to Sugarbush Resort along with Killington Resort and Pico Mountain. Its exposed beams, hand-built doors, and wide pine plank floors evoke classic New England architecture, while recent upgrades ensure comfort and convenience. Major enhancements include new

  Nathan Mastroeni

  1806 Vermont Route 100, Rochester, VT 05767
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  /47

  $379,900

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

  1001 Woodstock Rd, White River Junction, VT 05001

  Wonderful Ranch style home situated on a 2.5+/- acre in town lot and conveniently located only minutes from the bustling arts and theatre district of downtown White River Junction, VT. This home radiates warmth and hospitality and could be perfect for buyers looking for single level living! This two bedroom, (possible 3 bedroom,) two bath home is a rare opportunity to own a more affordable home

  Alex DeFelice The Clerkin Agency, P.C.

  1001 Woodstock Rd, White River Junction, VT 05001
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  /56

  $795,000

  • 3 Beds
  • 2 Baths
  • 1,940 Sq Ft

  211 Wood Rd, Hartford, VT 05001

  100 ACRE WOODS!! - Complete turn-key package for vacation rentals and a second home. Tucked away on 96+ protected acres spanning Hartford/Quechee, and a portion of Hartland, this fully furnished 3-bedroom, 2-bath log home offers exceptional privacy, quiet, & year-round recreation....Includes a robust (optional) rental program close to Woodstock. There is an existing subdivision in place if you

  John Bassette Bassette Real Estate Group

  211 Wood Rd, Hartford, VT 05001
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  /60

  $799,000

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

  329 Main St, Cavendish, VT 05153

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

  Benjamin Cote EXP Realty

  329 Main St, Cavendish, VT 05153
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  /45

  $439,000

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

  5798 W Woodstock Rd, Woodstock, VT 05091

  Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room

  Carol Wood Williamson Group Sothebys Intl. Realty

  5798 W Woodstock Rd, Woodstock, VT 05091
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  /28

  $5,500,000

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

  85 Pallottas Hill Rd, Ludlow, VT 05149

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

  Frank Provance Diamond Realty

  85 Pallottas Hill Rd, Ludlow, VT 05149
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  /37

  $165,000

  • 3 Beds
  • 1 Bath
  • 1,554 Sq Ft

  89 Route 12, Hartland, VT 05048

  Step into the charm of this antique home, offering an abundance of potential for restoration and customization. Highlights include beautiful wide board floors and a quiet, private backyard set on just under an acre. Ideal for buyers ready to take on a project and bring this special property back to life. Located in the desirable quaint town of Hartland, close to skiing, hiking, and Dartmouth,

  Erika Smith RE/MAX Upper Valley

  89 Route 12, Hartland, VT 05048
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  /48

  $165,000

  • 3 Beds
  • 1 Bath
  • 1,704 Sq Ft

  3 Chester Rd, Springfield, VT 05156

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

  Amy Hill EXP Realty

  3 Chester Rd, Springfield, VT 05156
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  /12

  $137,000

  • Land
  • 5.39 Acres
  • $25,417 per Acre

  0 Woodlawn Dr Unit 2 & 3 5063379, Hartford, VT 05001

  5.39+/- acre Parcels of land (when combined) in HARTFORD / WHITE RIVER JUNCTION, VT. located on Woodlawn Drive just off the VA Cut Off Road! 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. These building lots are conveniently located only 1 mile

  Alex DeFelice The Clerkin Agency, P.C.

  0 Woodlawn Dr Unit 2 & 3 5063379, Hartford, VT 05001
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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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  /26

  $149,000

  • Land
  • 0.23 Acre
  • $647,826 per Acre

  0 Prospect St Unit 5063213, Ludlow, VT 05149

  Here's your opportunity to purchase Ludlow's newest village lot offering. Lot 3 is located on the right side of the road and is the last lot on the street. Lot 3 is a nice level lot with endless possibilities. It has partial views of Okemo Mountain, and you'll see some spectacular sunsets. Ludlow's restaurants, shops, and parks are just a short walk away, and Okemo Mountain is about a mile away.

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Prospect St Unit 5063213, Ludlow, VT 05149
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  /24

  $374,000

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

  1163 Baker Turn Rd Unit 2E, Hartford, VT 05059

  Walk to the Quechee ski run from this spacious move in ready end unit. Open floor plan with high ceilings. A spacious living room that opens to a large new deck, new windows throughout. Granite counters in the kitchen, 1/2 bath on first floor. The second floor has two good sized bedrooms full bath and laundry. You have easy access to all the club amenities....skiing, golf, hiking trails, indoor

  Linda Hicks Quechee Lakes Real Estate Center

  1163 Baker Turn Rd Unit 2E, Hartford, VT 05059
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  /50

  $795,000 New Construction

  • 3 Beds
  • 3 Baths
  • 3,920 Sq Ft

  475 20 Mile Stream Rd, Reading, VT 05062

  Priced to reflect seller motivation--this nearly-complete, custom-designed sanctuary is a rare opportunity for the right buyer to add their finishing touch. Set on 12.69 pristine acres of rolling meadows, mature woods, and two peaceful streams just steps from the bedroom wing, this 3,800 sq ft home with 4-bedroom septic combines modern comfort with natural beauty. Central air, private well with

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  475 20 Mile Stream Rd, Reading, VT 05062
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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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  /50

  $1,100,000

  • 3 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  958 E Woodstock Rd, Woodstock, VT 05091

  Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive—every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air

  Keri Cole Williamson Group Sothebys Intl. Realty

  958 E Woodstock Rd, Woodstock, VT 05091
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  /19

  $115,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  1500 Brownsville-Hartland Rd, West Windsor, VT 05089

  Here's a chance to own your own property in West Windsor. This 3/4 +/- acre of land abuts one side up to Beaver Brook and you get views of Mt. Ascutney on the other side. This older mobile home with basement, offers the perfect opportunity for an investor. Restore the homes vintage charm or you could modernize the site with a new mobile unit. This was constructed as a 2-bedroom 1 bath home. One

  Ann Jacques Century 21 Highview Realty

  1500 Brownsville-Hartland Rd, West Windsor, VT 05089
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  /51

  $215,000

  • 2 Beds
  • 1 Bath
  • 892 Sq Ft

  145 Main St Unit 210, Ludlow, VT 05149

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

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  145 Main St Unit 210, Ludlow, VT 05149
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  /8

  $125,000

  • Land
  • 7.5 Acres
  • $16,667 per Acre

  00 Howe Hill Rd, Sharon, VT 05065

  Vermont Retreat Awaits. A 7.5 acre wooded parcel with spectacular mountain view potential and five bedroom state waste water permit is ready for your vision. Located off town-maintained Howe Hill Road in Sharon, Vermont, via right of way from lower parcel. Convenient access to power and ultra-high speed fiber optic (EC Fiber) internet at the street, just one mile from I-89. Enjoy easy access to

  Joanne Kent Four Seasons Sotheby's Int'l Realty

  00 Howe Hill Rd, Sharon, VT 05065
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  /8

  $225,000

  • Land
  • 15.4 Acres
  • $14,610 per Acre

  00 Howe Hill Rd, Sharon, VT 05065

  Pristine Wooded Parcel with easy access from a small clearing off town-maintained Howe Hill Road in Sharon, Vermont. Lot 1 has 15.4 acres, a three-bedroom approved waste water permit with plenty of room for gardens, trails, or your private retreat. Convenient access to power and ultra-high speed fiber optic (EC Fiber) internet at the street, just one mile from I-89 for easy drive to Upper Valley

  Joanne Kent Four Seasons Sotheby's Int'l Realty

  00 Howe Hill Rd, Sharon, VT 05065
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  /8

  $250,000

  • Land
  • 22.9 Acres
  • $10,917 per Acre

  00 Howe Hill Rd, Sharon, VT 05065

  Build Your Vermont Dream in Sharon. Nestled along scenic Howe Hill Road, these two building parcels offer the perfect mix of convenience, privacy, and possibility. The lower 15.4 acre parcel has three-bedroom waste water permit and direct access from a small clearing off Howe Hill Road. The upper 7.5 acre parcel has spectacular mountain view potential with five-bedroom waste water permit.

  Joanne Kent Four Seasons Sotheby's Int'l Realty

  00 Howe Hill Rd, Sharon, VT 05065
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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 trees and natural beauty—perfect for building your dream home, creating your own trail system, or simply enjoying the quiet serenity of the outdoors. Embrace the Vermont lifestyle surrounded by nature, while being just minutes from Quechee, Woodstock, Dartmouth, and all the shopping, dining, and

  Heather Ashline BHHS Verani Upper Valley

  0 Jericho St Unit 5062382, Hartford, VT 05001
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  /18

  $499,000

  • Land
  • 56.25 Acres
  • $8,871 per Acre

  0 Dothan Rd, White River Junction, VT 05001

  Discover ±56 acres at 0 Dothan Lane in Hartford, VT—an exceptional parcel offering unmatched flexibility, natural beauty, and convenience. Enjoy sweeping views over the White River Junction valley, multiple ideal building sites, and the option to subdivide into individual lots with a shared driveway access from Meadow Lane or Dorothy Road. A Right of Way will be granted at closing to provide

  Randy Snelling KW Coastal and Lakes & Mountains Realty/Hanover

  0 Dothan Rd, White River Junction, VT 05001
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  /54

  $2,599,000

  • 9 Beds
  • 11 Baths
  • 5,993 Sq Ft

  41 Pleasant St, Woodstock, VT 05091

  This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

  

  Jennifer Falvey

  KW Vermont Woodstock

  (802) 347-9544

  41 Pleasant St, Woodstock, VT 05091
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  /15

  $329,000

  • 4 Beds
  • 2 Baths
  • 1,373 Sq Ft

  40 Union St, White River Junction, VT 05001

  Good Cash Flow! Possibilty of Commercial business aspect exists with this property as its in the CB zone / Central Business district. This fully leased two unit property is an excellent chance for investors to add a consistent cash flowing building to their portfolio or for an onsite owner to occupy one unit and let the extra additional rent help pay for your housing. A fairly low maintenance

  Alex DeFelice The Clerkin Agency, P.C.

  40 Union St, White River Junction, VT 05001
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  /53

  $415,000 New Construction

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  696 Vermont Route 100, Ludlow, VT 05149

  LUDLOW: Minutes from Okemo Mountain Resort and Fox Run Golf Club. Approx. 600' of frontage on Lake Pauline with private dock. Permits are required to complete renovations. The property is private and level. There's an Artist Studio near the road that isn't currently used and needs to be rehabilitated. This unique property needs a new owner to complete it. Make this your dream property!

  Melissa Loughan Westside Real Estate

  696 Vermont Route 100, Ludlow, VT 05149
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  /9

  $1,050,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,390 Sq Ft

  8 Okemo Acres Rd, Ludlow, VT 05149

  Okemo Acres on Okemo Mountain – New Construction OpportunityLocated just off Okemo Ridge Access Road and only minutes from Okemo’s base lodge, this brand-new 3-bedroom home (with a septic permit for a 4th bedroom) is being built by a highly regarded local builder. The home will be completed within nine months of contract signing, with buyers having the opportunity to collaborate directly with

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

  8 Okemo Acres Rd, Ludlow, VT 05149
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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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  /27

  $379,000

  • 4 Beds
  • 2 Baths
  • 1,296 Sq Ft

  1668 Hartford Ave, Hartford, VT 05001

  Desirable Wilder location! Within walking distance to Kilowatt and Frost Parks, this charming home offers 4 bedrooms and 2 bathrooms with plenty of space for comfortable living. The recently remodeled kitchen opens seamlessly to the dining room, filling the main living area with natural light. Beautiful hardwood flooring runs throughout, and a spacious walk-up attic provides exciting potential

  Gerry Stark RE/MAX Upper Valley

  1668 Hartford Ave, Hartford, VT 05001
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  /42

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  1979 N Hill Rd, Chester, VT 05143

  Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting

  Geralyn Donohue Engel & Völkers Okemo

  1979 N Hill Rd, Chester, VT 05143
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  /29

  $299,000

  • Land
  • 3.05 Acres
  • $98,033 per Acre

  5268 Willard Rd, Hartford, VT 05059

  A stunning long-range view at the top of Willard Road in Quechee Lakes is what distinguishes this 3-acre parcel from many others. Cleared over a decade ago, the view is still available to the east and south, making this one unique for its location. Steeper topography will necessitate some creativity in access and construction details, but the location and neighborhood support the effort. A great

  Richard Higgerson Higgerson & Company

  5268 Willard Rd, Hartford, VT 05059
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  /29

  $299,000

  • 3 Beds
  • 3 Baths
  • 1,260 Sq Ft

  56 Grace Dr, Perkinsville, VT 05151

  3-bedroom, 3-bath Ranch-style home in a quiet North Springfield neighborhood with garage. This single-level rambler offers ease of living with a functional floor plan. Includes a partially finished basement with 3/4 bathroom. Set on a beautiful lot complete with sugar maples, pear, plum, and peach trees, a 21' round above ground pool with decking, and patio area with firepit to enjoy the open air

  Katie Ladue Gilbert KW Vermont Woodstock

  56 Grace Dr, Perkinsville, VT 05151
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  /58

  $925,000

  • 4 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  168 Okemo Trailside Extension Unit 21B, Ludlow, VT 05149

  Trailside 21B on Okemo Mountain. Discover the perfect balance of comfort, convenience, and mountain lifestyle in this completely renovated 4-bedroom, 3-bathroom trailside condominium located directly on the Sachem Trail. Offering true ski-in/ski-out access, this home makes it easy to enjoy your time on the slopes and retreat back to a warm, inviting space with quality finishes. The lower level

  Kevin Barnes William Raveis Real Estate Vermont Properties

  168 Okemo Trailside Extension Unit 21B, Ludlow, VT 05149
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  /3

  $59,000

  • Land
  • 3.15 Acres
  • $18,730 per Acre

  1003 Quarry Hill Rd, Rochester, VT 05767

  Undeveloped land parcel ready for you to utilize as a permanent home site or a camp spot. A blank canvas with access by truck or large SUV. Very near the Mountain Biking trail system and easy access onto paved town road. With tree clearing, this property can provide a great view of the Green Mt Range.

  Patricia Harvey Xsell Realty LLC

  1003 Quarry Hill Rd, Rochester, VT 05767
• 

  

  /29

  $530,000

  • 3 Beds
  • 2.5 Baths
  • 4,020 Sq Ft

  28 Fairview Terrace, Royalton, VT 05068

  This 3-bedroom, 2.5-bath home is full of potential, with the option to create an auxiliary dwelling for added flexibility. The current owner saw the promise in this gem and has already invested in the important updates: fresh exterior paint, a brand-new septic system, a new roof, upgraded electrical, and other quality improvements. With much of the essential work complete, the next owner has the

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  28 Fairview Terrace, Royalton, VT 05068
• 

  

  /50

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  187 Hopson Rd, Norwich, VT 05055

  This one-of-a-kind spacious home was designed by the architect, George T. Hathorn, and built by G.R. Porter and Sons - both of whom represent an era of home building quality unsurpassed to this day. As befits the climate, the centerpiece of this house is a woodstove, framed by a grand 3-story brick chimney and adjacent staircase – a unique layout that is both beautiful and wonderfully efficient

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  187 Hopson Rd, Norwich, VT 05055
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  /7

  $100,000

  • Land
  • 12.2 Acres
  • $8,197 per Acre

  00 Old Weston Mountain Rd, Ludlow, VT 05149

  Lot 9 - This 12.2-acre wooded lot offers potential for long-range mountain views with clearing. Easy access from a town-maintained gravel road.Located just 5 minutes from Ludlow and Okemo Mountain Resort, this property offers both privacy and proximity to year-round recreation and amenities.Two additional non-abutting lots are also available, presenting a great opportunity for a

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  00 Old Weston Mountain Rd, Ludlow, VT 05149

Showing Results 161 - 200, Page 5 of 11