Windsor County VT Homes for Sale

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  /59

  $379,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  1821 Chateauguay Rd, Bethel, VT 05032

  This sunny residence has been a beloved home to several generations of the same Vermont family. The location invites endless recreational activities! A snowmobile trail passes nearby, for winter excursions and the property is bounded by the cascading waters of Locust Creek, for cooling off in the Summer! The country road that passes by leads to the extraordinary Chateauguay-No Town conservation

  John Wetmore Wetmore Real Estate

  1821 Chateauguay Rd, Bethel, VT 05032
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  /47

  $895,000

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

  281 Okemo Trailside Extension Unit 30C, Ludlow, VT 05149

  Rare private location overlooking a lovely mountain stream and just steps from the Sachem ski trail. Four bedroom townhome on sunny south end of the building offers an open floor plan centered by a wood burning fireplace and accented by a wrap around deck. Kitchen includes updated flooring and appliances. Separate dining room adjoins a spacious living room with open beam cathedral ceiling.

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

  281 Okemo Trailside Extension Unit 30C, Ludlow, VT 05149
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  /44

  $800,000

  • 3 Beds
  • 1.5 Baths
  • 2,128 Sq Ft

  167 Limey Ln, Pomfret, VT 05053

  Welcome home to 167 Limey Lane, a wonderfully updated Cape style residence boasting the perfect mix of modern living with blissful privacy and natural beauty. Situated on a 5.24 acre parcel featuring a diversified landscape of level lawns giving way to open meadow, mature woodlands, and a cascading stream whose gentle rush provides a constant, soothing soundtrack, this is truly an oasis. Upon

  Connor Johnson KW Vermont

  167 Limey Ln, Pomfret, VT 05053
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  /49

  $1,250,000

  • 4 Beds
  • 4.5 Baths
  • 3,230 Sq Ft

  145 Stephen Day Ln, Hartford, VT 05001

  Unlike anything else in Quechee, this custom four-bedroom, four and a half bath Greek Revival farmhouse combines the fine craftsmanship of Connor Homes with exceptional custom finishes throughout. Generously proportioned spaces, superb lighting, radiant heat, and meticulous attention to detail create a home of remarkable elegance, warmth, and function. The beautifully designed kitchen features

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  145 Stephen Day Ln, Hartford, VT 05001
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  /38

  $249,500

  • 1,922 Sq Ft

  3668 Vt Route 103 N, Chester, VT 05143

  Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

  Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

  3668 Vt Route 103 N, Chester, VT 05143
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  /60

  $150,000

  • 4 Beds
  • 4 Baths
  • 2,838 Sq Ft

  6 Mill St, Ludlow, VT 05149

  Bring your vision and unlock the potential of this classic village property, ideally located on a quiet cul-de-sac within walking distance of Ludlow's restaurants, shops, parks, and year-round community events. Offering a 4-bedroom wastewater allocation, four bathrooms, and a top-floor apartment with its own private fire escape, this versatile property presents a variety of possibilities for

  Kevin Barnes William Raveis Real Estate Vermont Properties

  6 Mill St, Ludlow, VT 05149
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  /3

  $159,000

  • Land
  • 5 Acres
  • $31,800 per Acre

  00 Contro Rd, Chester, VT 05143

  There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town

  Christine Lewis Brattleboro Area Realty

  00 Contro Rd, Chester, VT 05143
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  /60

  $879,999

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,310 Sq Ft

  201 Spruce Dr, Chester, VT 05143

  Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermont’s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, it’s an ideal basecamp for

  Mendi Michael Engel & Völkers Okemo

  201 Spruce Dr, Chester, VT 05143
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  /12

  $125,000

  $10K PRICE DROP

  • Land
  • 16.9 Acres
  • $7,396 per Acre

  00 Day Rd, Sharon, VT 05065

  A wonderful opportunity to build in the quaint town of Sharon, VT. This unique acreage consists of a smaller open meadow that feeds into a picturesque and private roughed in logging road wrapping around a larger thinned out wooded area - offering a variety of potential locations to build your dream home. Potential for lovely views. The location is off a private dead-end road with I-89 only a few

  Bonnie Bergeron Snyder Donegan Real Estate Group

  00 Day Rd, Sharon, VT 05065
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  /47

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft

  343 Dublin Rd, Plymouth, VT 05149

  Looking for something a little different from the cookie-cutter floor plan? This inviting 3-bedroom Plymouth home has a fun, flexible layout, warm Vermont character, and a location that puts both mountain and lake adventures close at hand. Step inside through the welcoming foyer to an open, eat-in kitchen with warm wood details and plenty of room for casual meals, après-ski snacks, and gathering

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  343 Dublin Rd, Plymouth, VT 05149
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  /60

  $2,225,000

  • 4 Beds
  • 3 Baths
  • 3,867 Sq Ft

  473 Kendall Rd, Woodstock, VT 05091

  Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in

  Danny Kogut Williamson Group Sothebys Intl. Realty

  473 Kendall Rd, Woodstock, VT 05091
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  /5

  $75,000

  • Land
  • 21,780 Sq Ft
  • $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
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  /22

  $90,000

  • 0.5 Baths
  • 200 Sq Ft

  1093 Old Bow Rd, Springfield, VT 05156

  This welcoming 3-acre recreational getaway—with on-site power, a driveway entrance, and multiple sleeping quarters—offers the perfect retreat for anyone who loves hiking, biking, skiing, or simply relaxing in nature. Already set up for comfortable camping, the property includes a tiny house equipped with essential amenities and a trailer featuring its own private toilet room. Additional

  Christine Lavery North New England Real Estate Group

  1093 Old Bow Rd, Springfield, VT 05156
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  /41

  $1,200,000

  • 3 Beds
  • 3.5 Baths
  • 1,796 Sq Ft

  320 Okemo Trailside Extension Unit 36E, Ludlow, VT 05149

  Direct slopeside 3-bedroom plus family room townhome with numerous updates. Wonderful mountain location abuts Okemo State Forest and offers outstanding views. Expanded mudroom with built-ins leads out to private exterior ski closet and ski slopes. Kitchen updates include stainless steel appliances, tile floor and backsplash, and wood cabinetry. Open living room/dining room design with cathedral

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

  320 Okemo Trailside Extension Unit 36E, Ludlow, VT 05149
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  /36

  $525,000

  • 3 Beds
  • 3 Baths
  • 3,010 Sq Ft

  1545 E Hill Rd, Ludlow, VT 05149

  Welcome to your private country oasis. Nestled in a serene and peaceful setting, this pretty, two-level country home perfectly blends rustic charm with modern convenience. As you step inside, you are immediately greeted by an inviting open-concept living, dining, and kitchen area designed for seamless everyday living and effortless entertaining. This home features a magnificent stone wood-burning

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

  1545 E Hill Rd, Ludlow, VT 05149
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  /29

  $169,000

  $41K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  9 Stryhas Trailer Ct, Ludlow, VT 05149

  Charming and well-maintained 3-bedroom, 2-bathroom manufactured home on leased lot in a peaceful 55+ community. This inviting home features an open concept layout, high ceilings, and is filled with natural light pouring in through multiple skylights, creating a bright and airy atmosphere. Step outside to a new deck with an awning—perfect for enjoying warm summer days. The fenced yard is great for

  Gabrielle Turco Kelley Real Estate, Inc.

  9 Stryhas Trailer Ct, Ludlow, VT 05149
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  /24

  $452,600

  • 2,915 Sq Ft

  282 Skunk Hollow Rd, Hartland, VT 05048

  Two buildings on one parcel in desirable Hartland, Vermont! This flexible and well-maintained property includes a single-family home and a duplex, offering outstanding potential for owner occupancy, multi-generational living, or investment income. Ideally situated just 25 minutes from Hanover, NH, and 10 minutes from Woodstock, VT, this location provides the perfect balance of convenience and

  Loren Wehmeyer Tesla Realty Group, LLC

  282 Skunk Hollow Rd, Hartland, VT 05048
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  /35

  $69,900

  $2K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

  Desirable third-floor lockout unit in Jackson Gore, ideally positioned facing the valley with beautiful, expansive views. Located just steps from the Round House, this residence offers exceptional proximity to the lifts, pools, and dining, making it a perfect year-round getaway. Unit C features: A spacious one-bedroom layout with lockout capability, offering flexibility for personal use or rental

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

  368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
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  /36

  $649,000

  • 4 Beds
  • 3.5 Baths
  • 2,628 Sq Ft

  38 Rimrock Rd Unit 3A, Ludlow, VT 05149

  Four bedroom plus loft end unit just steps from the trail. Updated eat-in kitchen with wood cabinetry, farmer's sink, stainless steel appliances, tile backsplash, laminate floors, and quartz countertops. Sunken living room with exposed beam wood ceiling with fireplace leading out to an updated deck with long distance seasonal views, and updated half bath. A separate family room with fireplace and

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

  38 Rimrock Rd Unit 3A, Ludlow, VT 05149
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  /60

  $2,300,000

  • 6 Beds
  • 4.5 Baths
  • 8,656 Sq Ft

  55 Cherry Hill, Springfield, VT 05156

  Steeped in history and timeless elegance, this extraordinary circa-1860 Georgian Colonial estate offers over 8,000 square feet of refined living space where classic architecture meets remarkable craftsmanship. From the moment you enter, you are greeted by stunning period details including exquisite crown moldings, grand proportions, soaring ceilings, and beautifully preserved finishes that

  Joe Castaluccio Winhall Real Estate

  55 Cherry Hill, Springfield, VT 05156
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  /21

  $279,000

  • 2 Beds
  • 1 Bath
  • 783 Sq Ft

  15 US Route 5 N, Windsor, VT 05089

  Completely rebuilt in 2014 (except for the storage room) and set on 2.51 acres spanning both Windsor and Hartland, this 2-bedroom, 1-bath ranch offers comfortable one-level living with plenty of potential. The open-concept living, dining, and kitchen area creates a functional layout, while the attached direct-entry garage and unfinished attached space provide excellent storage or future expansion

  Karen DeMas Four Seasons Sotheby's Int'l Realty

  15 US Route 5 N, Windsor, VT 05089
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  /14

  $650,000

  • Land
  • 105.46 Acres
  • $6,163 per Acre

  0 Vermont 131, Ascutney, VT 05030

  Views of the surrounding hills including Mount Ascutney, Little Ascutney and Hawks Mountain. A large parcel with great variety. 35 acres of level cropland. Other fields, forest and transitional areas. Streams running through the land.20 minutes to skiing at Okemos. On the VAST trail system and only a short distance to I91 Exit 8. Ascutney Outdoors is nearby. Make your own farm or a family

  Matthew Spittle Vermont Horse Country Real Estate

  0 Vermont 131, Ascutney, VT 05030
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  /25

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft

  948 Wheelock Rd, Hartford, VT 05047

  This modern single-attached home combines contemporary design with practical living. Built to last, the residence features three bedrooms and two bathrooms arranged for comfortable daily living. Inside, the three-bedroom, two-bathroom layout provides functional space for residents. The home is protected by a new roof, new heating system, and many other upgrades, ensuring long-term durability and

  Mark Duchaine, Jr. BHHS Vermont Realty Group/S Burlington

  948 Wheelock Rd, Hartford, VT 05047
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  /16

  $650,000

  • Land
  • 10.03 Acres
  • $64,806 per Acre

  00 Little Pond Rd, Andover, VT 05143

  Located in the town of Andover, VT, this 10.4 acre parcel, showcasing an amazing long range mountain view, awaits the home of your dreams. The approach to the property is gorgeous with dramatic views and large neighboring parcels. The house site is tucked in the forest, with a roughed-in driveway already in place. This property has been thoughtfully composed, setting the stage for your custom

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Little Pond Rd, Andover, VT 05143
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  /14

  $74,000

  • Land
  • 15.5 Acres
  • $4,774 per Acre

  00 Remington Rd, Chester, VT 05143

  Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  00 Remington Rd, Chester, VT 05143
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  /51

  $599,000

  $125K PRICE DROP

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

  35 Stevens Rd, Cavendish, VT 05142

  Seller relocating....price reduced. Their loss is your find! Winter, Spring, Summer or Fall, this is a bit of heaven for the nature lover! Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know

  Betty McEnaney Diamond Realty

  35 Stevens Rd, Cavendish, VT 05142
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  /5

  $115,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  18 Tuckerville Pkwy, Ludlow, VT 05149

  Affordable home ownership in Ludlow, VT! This mobile home has two bedrooms, two bathrooms, a kitchen, a dining area, a living room with a stove, and a sunlit side porch/sunroom. It has a beautiful country setting in Tuckerville Parkway with a pretty and private yard, a double shed, a carport and additional parking on a paved driveway. The land is leased from the park, with a monthly fee of $359,

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

  18 Tuckerville Pkwy, Ludlow, VT 05149
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  /54

  $399,500

  $40K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,264 Sq Ft

  264 Elm Hill St, Springfield, VT 05156

  No words describe this property better than peaceful, rural, convenient and historic. Throughout its long life, the top of Elm Hill exudes country. The rugged stone walls, lower barn, tool shed and upper barn reveal an agricultural past. The upper barn has been converted to a 2-car garage and workshop, complete with a half-ton hoist. The upstairs hayloft (attic type storage) is easily accessible

  Carol Cole BHG Masiello Brattleboro

  264 Elm Hill St, Springfield, VT 05156
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  /21

  $135,000

  $130K PRICE DROP

  • Land
  • 13.96 Acres
  • $9,670 per Acre

  0 Valley View Dr Unit 5009431, Andover, VT 05143

  LOCATED ON THE LUDLOW BORDER OFFERS UNBELIEVABLE VALUE in a great setting ! Set at an elevation of 2,000+ feet, this exceptional parcel offers privacy, expansive long-range views, and an ideal setting for your Southern Vermont dream home. Located within a peaceful community of fine homes, this is one of the few remaining opportunities to build in this highly desirable area. The property includes

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  0 Valley View Dr Unit 5009431, Andover, VT 05143
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  /12

  $250,000

  $50K PRICE DROP

  • Land
  • 36.9 Acres
  • $6,775 per Acre

  1441 Jerusalem Hill, Rochester, VT 05767

  Set on 37± acres on the edge of Rochester’s wild landscape, this property offers a rare combination of immediate usability and long-term upside. Tucked just off the road for privacy, the land unfolds as a mix of rolling terrain, mature woods, and open pockets that invite exploration, recreation, and thoughtful development. At the center of it all is a rustic camp—simple, functional, and ready to

  William Brokhof Vermont Backcountry Real Estate

  1441 Jerusalem Hill, Rochester, VT 05767
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  /44

  $730,000

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

  46 Fowler Rd Unit O-205, Ludlow, VT 05149

  Winterplace at Okemo Mountain - Experience the ultimate in slopeside convenience, widely regarded as one of the most accessible locations on the mountain, with rare access to five chairlifts and nearby trail connections that bring you directly onto the slopes. This inviting three-bedroom, two-bathroom condo features an open-concept living area highlighted by a wood-burning fireplace—perfect for

  Katherine Burns William Raveis Real Estate Vermont Properties

  46 Fowler Rd Unit O-205, Ludlow, VT 05149
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  /45

  $599,000

  • 3 Beds
  • 3.5 Baths
  • 2,023 Sq Ft

  41 Parkhurst Unit L4, Cavendish, VT 05153

  Welcome to The Castle Hill Resort and Spa where you'll find this beautiful three bedroom, three and a half bath, condominium with loft and bonus room. The kitchen with custom cherry cabinetry, granite counters and stainless steel appliances that will satisfy any chef's needs is open to the living, dining area. Which have soaring cathedral ceilings and a wall of windows flooding in the natural

  Frank Provance Diamond Realty

  41 Parkhurst Unit L4, Cavendish, VT 05153
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  /59

  $1,249,000

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

  1355 Podunk Rd, Norwich, VT 05055

  The sun came first; everything else followed. Redesigned in 2010 by Smith & Vansant Architects, this south-facing contemporary in the hills of Norwich was shaped around light. Passive solar siting, 37 photovoltaic panels, and near-net-zero performance reflect an approach that values efficiency as much as design. At the center of the open living space, a Finnish Tulikivi soapstone woodstove

  Richard Higgerson Higgerson & Company

  1355 Podunk Rd, Norwich, VT 05055
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  /53

  $1,500,000

  • 6 Beds
  • 6 Baths
  • 6,240 Sq Ft

  817 Gulf Rd, Barnard, VT 05031

  One of the best opportunities our firm has ever presented. 192 acres, mountain views, pond, stream and waterfall - and three dwelling structures plus many outbuildings, in desirable Barnard VT, just 13 minutes drive to Woodstock village green. This is an estate sale of the late owner. This land with the Old Dean House (a cape house on a pond) was purchased and owned by a prominent family in

  John Snyder Snyder Donegan Real Estate Group

  817 Gulf Rd, Barnard, VT 05031
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  /34

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,276 Sq Ft

  232 Soaring Hawk Rd, Plymouth, VT 05056

  Tucked away on a quiet road in Hawk Resort, this charming 3-bedroom, 2-bath mountain retreat offers privacy, warmth, and easy access to Vermont's best four-season recreation. Just under 1,300 square feet, the home is thoughtfully designed to make the most of its inviting spaces, with random-width pine floors, a classic fieldstone fireplace, and abundant windows that bring in natural light and

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  232 Soaring Hawk Rd, Plymouth, VT 05056
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  /42

  $1,299,000

  • 4 Beds
  • 3 Baths
  • 4,372 Sq Ft

  278 Lawrence Hill Rd, Weston, VT 05161

  Experience the very best of Vermont living in the charming village of Weston, where every season offers something to enjoy. Spend winter days skiing at nearby Stratton, Magic, Bromley, or Okemo, and warmer months hiking scenic trails, horseback riding, swimming in lakes and ponds, or taking in a performance at the Weston Theater Company. Explore local shops, galleries, and restaurants while

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  278 Lawrence Hill Rd, Weston, VT 05161
• 

  

  /6

  $189,900

  • 3 Beds
  • 2 Baths
  • 980 Sq Ft

  28 Thetford Ln, Bethel, VT 05032

  On owned land 3 bedroom two bath mobile home on a concrete pad. 1.64 acres surveyed land. owner will consider owner financing with first mortgage. owner can help with qualifying. occupancy at closing. home has stand and seam metal roof, 2 sheds. estimated payment is 1,544.00 / month depending on rate, down payment etc.

  Derek Greene Derek Greene

  28 Thetford Ln, Bethel, VT 05032
• 

  

  /18

  $65,000

  $10K PRICE DROP

  • Land
  • 1.06 Acres
  • $61,321 per Acre

  0 Labbie Ln Unit 55, Hartford, VT 05001

  This +-1-acre undeveloped parcel on Labbie Lane offers an opportunity to build along a lovely paved cul-de-sac in Hartford. The location is highly practical for commuters, situated just ~2 miles from the shops and restaurants in White River Junction and approximately 15 minutes from Dartmouth-Hitchcock Medical Center. This is a straightforward opportunity to secure land in a very accessible Upper

  Holly Hall Hall Collins Real Estate Group

  0 Labbie Ln Unit 55, Hartford, VT 05001
• 

  

  /15

  $95,000

  • Land
  • 1.06 Acres
  • $89,623 per Acre

  00 Morrill Bend Unit 475, Hartford, VT 05001

  Build your dream home on this exceptional 1.06-acre parcel nestled along Morrill Bend, a quiet and scenic country lane within the desirable Quechee Lakes community. Offering both privacy and natural beauty, this lot is the perfect canvas for your Vermont retreat. Ownership includes membership to the renowned Quechee Club, providing access to an outstanding array of amenities. Enjoy paddling and

  Sandy Reavill

  00 Morrill Bend Unit 475, Hartford, VT 05001
• 

  

  /40

  $439,000

  • 2,496 Sq Ft

  2055 & 2071 Main and 28 Pleasant St, Cavendish, VT 05142

  Three properties are being sold together. Investors, Dreamers, Skiers, Business Owners, Anyone with Ideas and Support...Bring your ideas. Weddings in the barn? Indoor growing? A ski house? A cafe or store? With no zoning there are many possibilities.Pick up where the current owners left off with renovations and make it your own. In the past, the Okemo Shuttle has stopped across the street at

  Tyleen Murray Kelley Real Estate, Inc.

  2055 & 2071 Main and 28 Pleasant St, Cavendish, VT 05142

Showing Results 281 - 320, Page 8 of 14