Windsor County VT Homes for Sale

• 

  

  

  /46

  $599,000

  • 3 Beds
  • 3.5 Baths
  • 2,203 Sq Ft

  44 Freeman Rd Unit B2, Cavendish, VT 05153

  Unique opportunity to own a spacious three-bedroom townhouse at The Castle, one of the area's most sought-after luxury resort communities. Offering exceptional quality and amenities unlike any other in the region, residents enjoy year-round access to an Aveda spa, heated outdoor saltwater pool, tennis courts, a fully equipped fitness center with sauna and locker rooms, and an outdoor hot tub.

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  44 Freeman Rd Unit B2, Cavendish, VT 05153
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  /48

  $2,500,000

  • 6 Beds
  • 6 Baths
  • 7,019 Sq Ft

  5518 Vermont 12, Barnard, VT 05031

  This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family. Now, with children grown and off on their own paths, it is time to pass stewardship of the historic

  Laird Bradley Williamson Group Sothebys Intl. Realty

  5518 Vermont 12, Barnard, VT 05031
• 

  

  

  /43

  $1,249,000

  $246K PRICE DROP

  • Land
  • 48.11 Acres
  • $25,961 per Acre

  1 US Route 5 Rd, Hartland, VT 05048

  48.11 Acres of Spectacular Vermont Land with Panoramic Views!Discover a rare opportunity to own 48.11 acres of exceptional Vermont countryside in the heart of the Connecticut River Valley, often referred to as Vermont's "Shenandoah Valley" for its scenic beauty. This remarkable property offers breathtaking 180-degree views to the east and south, creating an unforgettable setting for a dream

  Charles Bacon Quechee Lakes Real Estate Center

  1 US Route 5 Rd, Hartland, VT 05048
• 

  

  

  /13

  $1,525,500

  New Construction

  • 4 Beds
  • 4 Baths
  • 2,752 Sq Ft

  5677 Hendee Way, Hartford, VT 05001

  The Jasper at Mountain Stream- To be built by Mountain Stream at Quechee Lakes, the Jasper offers 2,752 square feet of refined single-level living, paired with a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic central chimney give the home a distinctly modern presence- clean architectural lines softened by the

  Richard Higgerson Higgerson & Company

  5677 Hendee Way, Hartford, VT 05001
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  /57

  $1,650,000

  • 4 Beds
  • 4 Baths
  • 2,475 Sq Ft

  37 Village Center Rd Unit Blue Spruce 4, Ludlow, VT 05149

  SouthFace Village Blue Spruce #4 stands out as a truly hidden gem just waiting to be found.This nicely decorated 4-bedroom, 4-bath condominium has a unique blend of charm, natural beauty, modern amenities, and a warm, welcoming atmosphere that makes it more than just a place to live, it's a lifestyle. Blue Spruce #4 is a special ski-on/ski-off property with 2-level living, an open concept

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

  37 Village Center Rd Unit Blue Spruce 4, Ludlow, VT 05149
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  /27

  $425,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  100 Riverside Ln, Royalton, VT 05068

  Tucked away on a private drive just off Route 14, this thoughtfully designed three-bedroom, two-bath Ranch offers comfortable single-level living with room to grow. An open floor plan, hardwood floors, and abundant natural light create a warm and inviting atmosphere, while the southwest-facing orientation fills the home with sunshine throughout the day. The spacious primary bedroom suite provides

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  100 Riverside Ln, Royalton, VT 05068
• 

  

  /22

  $85,000

  • Land
  • 5 Acres
  • $17,000 per Acre

  0 Linden Way Unit 5093908, Chester, VT 05143

  Privacy doesn't have to mean isolation!!Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a

  Daire Gibney Barrett and Valley Associates Inc.

  0 Linden Way Unit 5093908, Chester, VT 05143
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  /42

  $750,000

  • 4 Beds
  • 3 Baths
  • 2,776 Sq Ft

  75 Upper Crossroad Unit C6, Ludlow, VT 05149

  Welcome to Okemo Village Condo C6, a rare opportunity to own one of the resort's most desirable four-bedroom, three-bath residences. Ideally located just steps from the Okemo Base Lodge and ski trails, this spacious condominium offers exceptional convenience for enjoying everything the mountain has to offer. Thoughtfully remodeled and tastefully decorated, the home is being offered furnished,

  Kevin Barnes William Raveis Real Estate Vermont Properties

  75 Upper Crossroad Unit C6, Ludlow, VT 05149
• 

  

  /10

  $700,000

  • 3,526 Sq Ft

  754 Hartford Ave, Hartford, VT 05001

  Opportunity is in the spin cycle at the White River Junction Laundromat! This turnkey, established business offers a rare chance to own a laundromat in a highly visible location with excellent accessibility and steady customer traffic. Adding to its appeal are two spacious, updated one-bedroom apartments, both fully occupied, providing reliable rental income alongside the business. Positioned in

  Samuel Roberts

  754 Hartford Ave, Hartford, VT 05001
• 

  

  /16

  $3,150,000

  • Land
  • 506 Acres
  • $6,225 per Acre

  00 Marsh Cross Rd, Andover, VT 05143

  Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence. This land's historical roots run deep, originally belonging to the Marsh

  Story Jenks LandVest, Inc/Woodstock

  00 Marsh Cross Rd, Andover, VT 05143
• 

  

  /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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  /58

  $1,250,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 3,363 Sq Ft

  30 Garcia Ln, Hartland, VT 05048

  This spacious, bright, impeccably maintained hilltop retreat checks all the boxes, with stunning long-range views to both the southeast and northwest. Open concept kitchen with granite counters, maple cabinetry, pantry, excellent quality stainless steel appliances, and mudroom entry. Private deck and porch for outdoor entertaining. The living room is anchored by a brick wood-burning fireplace,

  Danny Kogut Williamson Group Sothebys Intl. Realty

  30 Garcia Ln, Hartland, VT 05048
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  /44

  $789,000

  $60K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 4,388 Sq Ft

  223 Coach Rd, Chester, VT 05143

  Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to

  Daire Gibney Barrett and Valley Associates Inc.

  223 Coach Rd, Chester, VT 05143
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  /59

  $4,999,000

  • 5 Beds
  • 4.5 Baths
  • 9,170 Sq Ft

  62 Moon Shadow Dr, Ludlow, VT 05149

  Welcome to one of Okemo’s most distinctive properites, an iconic SKI-ON, SKI-OFF Tennessee log-style home set directly on the Moon Shadow ski trail within Solitude Village. This home offers the ultimate slopeside lifestyle with panoramic mountain views stretching across the Okemo Valley. Crafted with authentic log construction, showcasing broad hewn timbers, wide chinking, reclaimed wood floors,

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  62 Moon Shadow Dr, Ludlow, VT 05149
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  /39

  $424,500

  $25K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  339 Ranney Rd, Stockbridge, VT 05772

  EXTRA ACRE! EXTRA VALUE. PROPERTY NOW INCLUDES one more acre than previously listed. Take a look at this home in central Vermont- close to the premier Killington Mountain Ski Resort. This property is on an open 3 acre lot with plenty of sun and space for pets, gardens, greenhouses or farm animals. This Stockbridge home has an in-law apartment below- accessible by a separate driveway. It provides

  Risa Mornis Covered Bridge RE

  339 Ranney Rd, Stockbridge, VT 05772
• 

  

  /17

  $449,000

  • 1 Bed
  • 1 Bath
  • 920 Sq Ft

  35 Railroad Row Unit C3-1, Hartford, VT 05001

  A rare opportunity to own one of downtown White River Junction's sought after Railroad Row condominiums. Offered fully furnished, this stylish, urban residence combines contemporary design with industrial character. It features soaring ceilings, oversized windows, bamboo floors, an open concept layout filled with natural light and views over the park. Enjoy the convenience of elevator access,

  Linde McNamara LindeMac Real Estate

  35 Railroad Row Unit C3-1, Hartford, VT 05001
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  /12

  $225,000

  $25K PRICE DROP

  • Land
  • 16 Acres
  • $14,062 per Acre

  2840 Vt Route 14, Royalton, VT 05068

  Long White River frontage, high and dry house site offering pleasant view over Vermont Law School and level hay field. House site has utilities available and existing frontage on Route 14.

  Dean Goulet Dunrovin Real Estate

  2840 Vt Route 14, Royalton, VT 05068
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  /7

  $1,250,000

  • Land
  • 14,810 Sq Ft
  • $3,676,471 per Acre

  130 Main St, Ludlow, VT 05149

  For generations, the Pot Belly building was a familiar and beloved part of Ludlow Village—a place where locals and visitors gathered, stories were shared, and the energy of the village came to life. Today, the building may be gone, but the opportunity it created is just beginning.Now offered as a prime, cleared village lot, this property represents a rare chance to be part of Ludlow’s next

  Joseph Karl William Raveis Real Estate Vermont Properties

  130 Main St, Ludlow, VT 05149
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  /60

  $200,000

  $10K PRICE DROP

  • 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 (includes Christmas weeks for 2026). 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

  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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  /36

  $2,790,000

  • 4 Beds
  • 4.5 Baths
  • 2,894 Sq Ft

  1726 Skitchewaug Trail, Springfield, VT 05156

  Set on 157 private acres with sweeping long-range views of the Connecticut River, this meticulously restored circa 1735 Cape offers a rare blend of historic character, refined comfort, and estate-scale amenities. Completely dismantled and rebuilt with care, the post-and-beam residence displays exposed beams, wide-board floors and sheathing, gunstock corner posts, and classic brick fireplaces

  Scott Monahan Williamson Group Sothebys Intl. Realty

  1726 Skitchewaug Trail, Springfield, VT 05156
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  /45

  $442,999

  • 3 Beds
  • 2 Baths
  • 1,961 Sq Ft

  6 Pine St, Windsor, VT 05089

  Shown by Appointment Only! Single Family or Duplex! Live in it as a spacious 3 bedroom, 2 bath single family home, or take advantage of the current setup as two separate 1 bedroom units, each with its own utilities. That kind of flexibility is hard to find, whether you're thinking multigenerational living, rental income, or just extra breathing room. And then there's the view. Gorgeous lake views

  Rachael Lapp BHHS Verani Upper Valley

  6 Pine St, Windsor, VT 05089
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  /18

  $175,000

  • Land
  • 22.2 Acres
  • $7,883 per Acre

  00 Comstock Dr, Bethel, VT 05032

  Tucked just off Campbrook Road, this 22-acre parcel offers the perfect blend of privacy and convenience in the heart of Vermont's White River Valley. Already permitted for a 3-bedroom wastewater system, the property is ready for you to build the home you've been dreaming of. The land sits in a quiet, secluded setting while remaining just moments from a paved road, making year-round access a

  Lucas deSousa Vermont Real Estate Company

  00 Comstock Dr, Bethel, VT 05032
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  /59

  $1,150,000

  • 5 Beds
  • 4.5 Baths
  • 3,370 Sq Ft

  1036 N Main St, Bethel, VT 05032

  Set along the storied banks of the White River, the historic WA Dunham Farm—also known as the Hungerford Farm—offers a rare blend of Vermont heritage, natural beauty, and modern comfort on 92.6 conserved acres. Originally built circa 1867, this extensively restored estate features nearly one mile of private river frontage with a secluded beach, perennial streams, protected woodlands, open

  Evan Russell Real Broker LLC

  1036 N Main St, Bethel, VT 05032
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  /39

  $445,000

  $84K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,656 Sq Ft

  2140 Brandon Mountain Rd, Rochester, VT 05767

  Tucked away on a picturesque 3-acre lot, this classic three-bedroom expanded Cape offers privacy, seclusion, and wonderful views in a beautiful Rochester valley setting. Set nearly 700 feet back from the road and bordering the Green Mountain National Forest, the property enjoys a tranquil natural backdrop where a scenic pond at the edge of the land attracts birds and wildlife. The main level

  Kyle Kershner Killington Pico Realty

  2140 Brandon Mountain Rd, Rochester, VT 05767
• 

  

  /57

  $529,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  94 James St, Hartford, VT 05047

  PRICE REDUCED!! Wonderful ranch style home that has way more than meets the eye! This well built home is situated on a .65 +/- acre in town lot and is full of quality features inside and out and just a short walk to Frost Park in Wilder, VT.. This home features single level living with three bedrooms, two baths, eat in kitchen, dining area and a beautiful 3 season sunroom just off the kitchen

  Alex DeFelice The Clerkin Agency, P.C.

  94 James St, Hartford, VT 05047
• 

  

  /24

  $289,000

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft

  38 Okemo Trailside Extension Unit 8A, Ludlow, VT 05149

  Sun-drenched and thoughtfully designed, this one-bedroom condo is ideally located in the sought-after Trailside community, just moments from the Sachem Trail, the new in-ground swimming pool, tennis courts, and additional parking. Offering true four-season appeal, it provides effortless access to Okemo Mountain while also serving as a comfortable year-round retreat. The open-concept layout is

  Karen Wilson TPW Real Estate

  38 Okemo Trailside Extension Unit 8A, Ludlow, VT 05149
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  /28

  $599,500

  • 1 Bed
  • 1.5 Baths
  • 1,611 Sq Ft

  513 Shattuck Hill Rd, West Windsor, VT 05037

  Welcome to the Carriage House, a rustic chic hideaway set on 5.13 acres overlooking a private pond in the bucolic West Windsor countryside. The recent, complete renovation of this exceptional property is truly a work of art, blending refined design with effortless comfort. The open main level is thoughtfully designed for both entertaining and everyday living, with a gourmet kitchen featuring

  Mary Mayhew Snyder Donegan Real Estate Group

  513 Shattuck Hill Rd, West Windsor, VT 05037
• 

  

  /23

  $319,500

  $50K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 835 Sq Ft

  105 Williams Ln Unit 6C, Hartford, VT 05001

  Unit 6C is a well-positioned, three-level condominium in Kingswood Village at the top of Quechee Ski Hill, offering the convenience of immediate access to the slopes less than 500 ft away! This turnkey, fully furnished home provides a seamless entry into the Quechee Lakes lifestyle. Two bedrooms on the lower level provide privacy, while a large 17’ x 15’ loft on the third floor offers additional

  Richard Higgerson Higgerson & Company

  105 Williams Ln Unit 6C, Hartford, VT 05001
• 

  

  /34

  $449,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft

  6852 Us Route 4, Bridgewater, VT 05034

  This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

  Laird Bradley Williamson Group Sothebys Intl. Realty

  6852 Us Route 4, Bridgewater, VT 05034
• 

  

  /32

  $589,000

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  314 Dorman Rd, Andover, VT 05143

  Silence is the first thing you notice. Set on 10+/- peaceful acres in Andover, this comfortable and well-maintained three-bedroom, two-bath home offers the kind of Vermont setting that is getting harder to find. No traffic noise, no bustle, just woods, privacy and room to breathe. Inside, the home is warm and inviting, with an easy layout equally suited to full-time living or weekends in the

  Daire Gibney Barrett and Valley Associates Inc.

  314 Dorman Rd, Andover, VT 05143
• 

  

  /32

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,549 Sq Ft

  43 Hartness Way, Hartford, VT 05047

  Welcome to an inviting single-family retreat set in the highly desirable Quechee Lakes Association in Hartford, Vermont, offering a fabulous four-season lifestyle just minutes from Upper Valley employment hubs, Dartmouth Health, and local shopping. Featuring 3 bedrooms and 2 full baths, the home boasts a airy, open-concept floor plan that seamlessly connects the main living, dining, and kitchen

  Chelsea Bevis KW Vermont Woodstock

  43 Hartness Way, Hartford, VT 05047
• 

  

  /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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  /24

  $600,000

  $50K PRICE DROP

  • 2,674 Sq Ft

  5863 Vermont 14, Royalton, VT 05068

  Overlooking the magnificent White River and Second Branch, this attractive older home has been a labor of love for the past 30 years. The long list of upgrades, additions, improvements, etc. speak for themselves. The spacious first floor has been used as home occupation featuring a 350 sq. ft. impressive office space. The apartments can be opened up to be single family or collect a projected net

  Dean Goulet Dunrovin Real Estate

  5863 Vermont 14, Royalton, VT 05068
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  /51

  $399,800

  $29K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056

  Perched at 1,600 feet elevation between Okemo and Killington, this beautifully furnished 3-bedroom, 2-bath condo at Hawk Resort offers the perfect mountain escape--complete with everything you need to move right in.Step into an open-concept living and dining area that flows onto a private deck through glass sliders--perfect for enjoying the sunsets. The living room features soaring cathedral

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  107 Blueberry Ledge Ridge Unit 45, Plymouth, VT 05056
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  /52

  $724,900

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,049 Sq Ft

  65 Steele Hill Rd, Weathersfield, VT 05030

  Tucked among the trees with mountain views that stop you in your tracks, this 2-bedroom, 3-bath Cape pairs old New England charm with everything you'd want in a modern home. Even before you reach the door, the landscaping tells you something special is inside: ornamental plantings, natural boulder accents, manicured gardens, and a fire pit for cool evenings. There is beauty tucked into every

  Katie Ladue Gilbert BHHS Verani Upper Valley

  65 Steele Hill Rd, Weathersfield, VT 05030
• 

  

  /44

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  63 Best Rd, Windsor, VT 05089

  Experience the perfect blend of Vermont charm and modern comfort in this beautifully maintained 3-bedroom, 2-bath modern Craftsman-style home set on 3.75 scenic acres with sweeping eastern views of the New Hampshire mountains, including Mt. Cardigan on a clear day. Bathed in natural light, this move-in ready home features warm, inviting living spaces designed for everyday comfort and effortless

  Bonnie Bergeron Snyder Donegan Real Estate Group

  63 Best Rd, Windsor, VT 05089
• 

  

  /38

  $345,000

  • 7 Beds
  • 3.5 Baths
  • 3,555 Sq Ft

  114 Bethel Mtn Rd, Rochester, VT 05767

  Opportunity awaits in the heart of Rochester Village! Located just off the Village Green, this versatile property offers exceptional income-producing potential. The existing second-floor apartment, complete with its own bedroom and full bath, is ideal for rental income, guest accommodations, employee housing, or multi-generational living. With its generous layout and village location, the

  Kate Cassidy Four Seasons Sotheby's Int'l Realty

  114 Bethel Mtn Rd, Rochester, VT 05767
• 

  

  /35

  $350,000

  $3K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,225 Sq Ft

  99 Heather Dr Unit 8F, White River Junction, VT 05001

  Immaculately cared for Hemlock Ridge Condo. This two bedroom, two bath unit with dedicated parking is a rare find and has had many wonderful updates over the last several years. Updates include a new Viesman Boiler / heating unit, windows, Daiken mini split units on each floor, pantry, custom blinds and flooring. Interior features include a large open concept dining room and living room space

  Alex DeFelice The Clerkin Agency, P.C.

  99 Heather Dr Unit 8F, White River Junction, VT 05001
• 

  

  /49

  $5,250,000

  • 4 Beds
  • 7 Baths
  • 7,715 Sq Ft

  83 Town Farm Hill Rd, Hartland, VT 05048

  Hartland Hill Farm unfolds across rolling meadows in one of the Upper Valley's most picturesque settings. Sited to embrace the surrounding landscape, the property enjoys sweeping pastoral views east to New Hampshire's White Mountains and south over open fields to the iconic silhouette of Mount Ascutney. Mature maples, stone walls, an apple orchard, two ponds, productive farmland, and a classic

  Dia Jenks LandVest, Inc/Woodstock

  83 Town Farm Hill Rd, Hartland, VT 05048
• 

  

  /41

  $339,000

  $60K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 2,200 Sq Ft

  109 Park Row, Rochester, VT 05767

  Known locally for generations as The Old Richard Steele Hubbard Home, this circa-1902 village residence reflects Rochester’s prosperous early-20th-century era and retains many of its original architectural details. Ideally situated just off the park in the charming historic village of Rochester, Vermont, this special home is a fine example of the American Foursquare style popular in the late 19th

  Kyle Kershner Killington Pico Realty

  109 Park Row, Rochester, VT 05767

Showing Results 81 - 120, Page 3 of 13