Windsor County VT Homes for Sale

• 

  

  

  /58

  $485,000

  • 8 Beds
  • 1 Bath
  • 3,500 Sq Ft

  1254 U S 5, Springfield, VT 05156

  Welcome to the former Danforth Inn! Take a trip back in time to 1780 as you look at this extremely original old building that was built in Weathersfield Bow in 1780 by Gideon Lyman. In 1789 Joseph Danforth moved to the Bow and he leased and then bought the Inn, changing the name to the Danforth Inn. This property will need some love, but it has never been spoiled in its originality, and it's just

  Glenn Olney Barrett and Valley Associates Inc.

  1254 U S 5, Springfield, VT 05156
• 

  

  

  /33

  $299,000

  • 2,702 Sq Ft

  41 Vt Route 103 S, Chester, VT 05143

  Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. There is good road frontage for plenty of parking. Consider the

  Glenn Olney Barrett and Valley Associates Inc.

  41 Vt Route 103 S, Chester, VT 05143
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  /58

  $2,950,000

  • 5 Beds
  • 5.5 Baths
  • 3,460 Sq Ft

  48 Alpine Way Unit D-1, Ludlow, VT 05149

  Show Stopper—this five-bedroom slopeside townhouse sits just steps from the trails and offers three private suites across three levels of beautifully curated living space. Completely reimagined by a talented local designer, it features an organic palette, thoughtful details, and a true move-in-ready feel—just hang your artwork and your skis. The chef’s kitchen showcases a Dekton waterfall

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

  48 Alpine Way Unit D-1, Ludlow, VT 05149
• 

  

  

  /14

  $289,000

  • 2 Beds
  • 2.5 Baths
  • 1,475 Sq Ft

  106 Contro Rd, Chester, VT 05143

  Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

  Christine Lewis Brattleboro Area Realty

  106 Contro Rd, Chester, VT 05143
• 

  

  

  /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
• 

  

  /41

  $399,000

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

  109 Park Row, Rochester, VT 05767

  The Richard Steele Hubbard home, ideally situated just off the park in the charming village of Rochester, Vermont, is a fine example of the American Foursquare style popular in the late 19th and early 20th centuries. This five-bedroom residence retains many period details, including handcrafted woodwork, hardwood floors, coffered ceilings, stamped tin, and decorative moldings. Thoughtful updates

  Kyle Kershner Killington Pico Realty

  109 Park Row, Rochester, VT 05767
• 

  

  /41

  $1,576,000

  • 9,455 Sq Ft

  14 Summarsell Dr Unit 16, Hartland, VT 05048

  This charming converted farmstead features two primary buildings on one parcel, combining classic Vermont character with solid investment returns. The property offers a diverse mix of one-, two-, and four-bedroom apartments, plus one commercial unit currently leased to a local bath and body company. Additional income comes from a three-bay garage, a shed, and a storage container — all fully

  Loren Wehmeyer Tesla Realty Group, LLC

  14 Summarsell Dr Unit 16, Hartland, VT 05048
• 

  

  /31

  $299,000

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft

  29 Markham Ln, Weston, VT 05161

  This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

  Catherine Cairns Maple Leaf Realty

  29 Markham Ln, Weston, VT 05161
• 

  

  /41

  $999,500

  • 3,218 Sq Ft

  1 Depot St, Hartford, VT 05001

  Excellent Upper Valley investment opportunity! This well-maintained six-unit multifamily property features a desirable mix of 3 one-bedroom apartments and 3 two-bedroom apartments, ideally situated in the heart of Wilder. The property sits directly across from the bus stop and offers convenient access to major employers and amenities — just 9 minutes (4.2 miles) from Dartmouth College and 17

  Loren Wehmeyer Tesla Realty Group, LLC

  1 Depot St, Hartford, VT 05001
• 

  

  /8

  $590,000

  • Land
  • 61.49 Acres
  • $9,595 per Acre

  00 Wild Apple Rd, Pomfret, VT 05067

  One of the most sought-after locations in the Woodstock area, this 61-acre property is accessed off of Wild Apple Road with a building site oriented to the south and east. At 1,600 feet in elevation, it enjoys sweeping views of Killington, Mount Ascutney, and the surrounding hills. The land offers complete privacy with a blend of woodlands, open fields, a stream, and a pond site. Bordering the

  Story Jenks LandVest, Inc/Woodstock

  00 Wild Apple Rd, Pomfret, VT 05067
• 

  

  /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
• 

  

  /40

  $795,000

  • 6 Beds
  • 9 Baths
  • 4,744 Sq Ft

  19 Huntington Place, Rochester, VT 05767

  Imagine living in an 1806 home on a Vermont green. Located in the heart of the Green Mountains in the quaint town of Rochester, along the scenic Route 100 corridor. The property is currently a classic Vermont Inn with a chef-owned restaurant and tavern with lovely accommodations. Easily refurnished for private use. The home sits atop the Rochester Green. The village features galleries, shops, and

  Kate Cassidy Four Seasons Sotheby's Int'l Realty

  19 Huntington Place, Rochester, VT 05767
• 

  

  /9

  $249,000

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

  715 Giddings St, Springfield, VT 05150

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

  Thaddeus Abare Barrett and Valley Associates Inc.

  715 Giddings St, Springfield, VT 05150
• 

  

  /5

  $249,000

  • 4 Beds
  • 4 Baths
  • 2,767 Sq Ft

  3 Wall St, Springfield, VT 05156

  This property is a great source of revenue, with a good sound structure and well maintained utilities this property can serve as a great investment. Within walking distance to down town Springfield where you can find groceries, shops, restaurants and more.

  Thaddeus Abare Barrett and Valley Associates Inc.

  3 Wall St, Springfield, VT 05156
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  /11

  $39,999

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

  341 Seavers Brook Rd, Springfield, VT 05156

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

  David White OwnerEntry.com

  341 Seavers Brook Rd, Springfield, VT 05156
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  /49

  $715,000

  • 4 Beds
  • 3.5 Baths
  • 2,654 Sq Ft

  760 E Ash Rd, Plymouth, VT 05056

  Spacious Hawk Resort Home with Scenic Views Enjoy the perfect blend of comfort, space, and mountain charm in this inviting Hawk home. Designed for family gatherings and entertaining, the generous open-concept living area features a beautiful fieldstone fireplace and updated greenhouse windows that bring in natural light and picturesque views. The primary suite offers a cozy fireplace, private

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  760 E Ash Rd, Plymouth, VT 05056
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  /10

  $35,000

  • Land
  • 5.6 Acres
  • $6,250 per Acre

  00 Va Cutoff Rd, Hartford, VT 05001

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

  David White OwnerEntry.com

  00 Va Cutoff Rd, Hartford, VT 05001
• 

  

  /37

  $102,000

  • 2 Beds
  • 3 Baths
  • 1,367 Sq Ft

  617/619 Qtr I Adams House, Ludlow, VT 05149

  Adams House Unit 617/619 Qtr.I : Quarter OwnershipExperience mountain comfort in this spacious 2-bedroom, 3-bath slope-facing condominium that sleeps eight. The primary bedroom features a king bed and ensuite bathroom. The main living area includes a full kitchen, a cozy gas fireplace, a sleep sofa, and a convenient guest bathroom. The lockout side offers two queen beds and a private

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

  617/619 Qtr I Adams House, Ludlow, VT 05149
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  /9

  $175,000

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

  476 Missing Link Rd, Springfield, VT 05156

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

  Victoria Woods Brattleboro Area Realty

  476 Missing Link Rd, Springfield, VT 05156
• 

  

  /3

  $220,000

  • Land
  • 50.45 Acres
  • $4,361 per Acre

  0 Missing Link Rd, Springfield, VT 05156

  Sitting high above Rte 5, this large parcel has a prime view out over the Connecticut River. There's a septic permit in place for a 5 bedroom home. You'll need to improve the old logging road to gain access to the top but once you do, there are 50 acres to explore. Enroll in the Use Value Program to reduce your taxes!

  Victoria Woods Brattleboro Area Realty

  0 Missing Link Rd, Springfield, VT 05156
• 

  

  /41

  $795,000

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

  115 Prior Rd, Cavendish, VT 05142

  Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral

  Glenn Olney Barrett and Valley Associates Inc.

  115 Prior Rd, Cavendish, VT 05142
• 

  

  /19

  $27,500

  • Land
  • 1.98 Acres
  • $13,889 per Acre

  2-47 E Ash Rd, Plymouth, VT 05056

  Nice building lot within Hawk Resort. Some flat areas with potential westerly views. Electric and high speed internet is at street and there is the option to hook into community septic. Nestled in the scenic lakes region, halfway between Killington and Okemo, Hawk offers a prime location for outdoor enthusiasts. Whether you're hitting the slopes, exploring the trails, or simply enjoying the

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  2-47 E Ash Rd, Plymouth, VT 05056
• 

  

  /45

  $519,000

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

  185 Beans Bridge Rd, Rochester, VT 05767

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

  Kyle Kershner Killington Pico Realty

  185 Beans Bridge Rd, Rochester, VT 05767
• 

  

  /10

  $349,000

  • Land
  • 60 Acres
  • $5,817 per Acre

  911 Waterman Rd, Royalton, VT 05068

  Explore the opportunity of this 60 Acre parcel which is beautifully wooded with awesome mountain view potential. Extensive walking trails throughout the land. Possible development options here or build your private dream retreat. VAST Snowmobile Trails run through the property and the backside of the land abuts the Second Branch of the White River. The land has never been percd for septic. Come

  Marni Rieger KW Vermont-Killington

  911 Waterman Rd, Royalton, VT 05068
• 

  

  /17

  $825,000

  • 4 Beds
  • 1.5 Baths
  • 2,200 Sq Ft

  1928 Vermont 131, Springfield, VT 05156

  COUNTRY LIVING ON 118 ACRES WITH FULLY APPLIANCED, 4 BR's, 1.5 BATH HOME WITH ATTACHED GARAGE WITH 2ND FLOOR, A STATE-OF-THE ART PELLET BOILER, ROOF TOP SOLAR SYSTEM, SMALL POND, BARN AND STORAGE BUILDINGS. THE LAND BOAST ONE OF THE MOST BEAUTIFUL AND PLENTIFUL SUGAR BUSH IN THE STATE THAT EASILY ACCOMADATES OVER 4500 TAPS. SEVERAL WELL-MAINTAINED WOOD-LAND TRAILS TRAVERSE THE ACREAGE AND THE

  Don Chabot Town and Country Realty

  1928 Vermont 131, Springfield, VT 05156
• 

  

  /58

  $390,000

  • 5 Beds
  • 3 Baths
  • 1,976 Sq Ft

  198 Depot St, Cavendish, VT 05153

  Welcome to this charming home nestled in a small neighborhood along the scenic Black River in Cavendish, Vermont. This inviting property combines classic Vermont character with versatile living spaces, all within walking distance of the town green, shops, restaurants, and more. Step inside through the mudroom. The kitchen offers a warm, welcoming space with a sunny dining area perfect for morning

  Katherine Burns William Raveis Real Estate Vermont Properties

  198 Depot St, Cavendish, VT 05153
• 

  /2

  $168,000

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

  0 Gird Lot Rd Unit 5066640, Weathersfield, VT 05030

  On an abandoned road running along Blood Brook, this 56 acre parcel of land, rising to 1000 feet-with potential views of New Hampshire, is a perfect property for all sorts of uses, from simple walks to possible development. Seize this opportunity to own land in Vermont that is also only minutes to Route 91 and the rest of the Upper Valley.

  John MacGovern Dark Horse Realty

  0 Gird Lot Rd Unit 5066640, Weathersfield, VT 05030
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  /59

  $14,900,000

  • 7 Beds
  • 10 Baths
  • 12,520 Sq Ft

  355 Greene Rd, Woodstock, VT 05071

  Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

  Chris Lang

  355 Greene Rd, Woodstock, VT 05071
• 

  

  /60

  $32,000,000

  • 2 Beds
  • 7 Baths
  • 9,950 Sq Ft

  650 Francis Rd, Barnard, VT 05031

  Set on 400+/- acres in Barnard, Vermont, Monsalvat Farm is a legacy estate where rolling pastures, stone walls, forests, and mountain views reflect the state’s timeless character. Settled in 1793, the land carries generations of stewardship, elevated by one of the finest residences in the country—an architectural masterpiece complemented by historic and companion structures that are carefully

  Chris Lang

  650 Francis Rd, Barnard, VT 05031
• 

  

  /24

  $299,000

  • Land
  • 4.3 Acres
  • $69,535 per Acre

  00 Chateauguay Rd, Barnard, VT 05031

  A rare and beautiful parcel of land that is cleared, level and ready to be built upon with over 1200 feet of frontage along the North Branch of Locust Creek.Locust Creek runs year round with water falls and deep pools, not only pleasant to look at, but fun to play in.Site prep costs for a parcel like this will be considerably lower than wooded lots that require clearing and excavation.

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Chateauguay Rd, Barnard, VT 05031
• 

  

  /58

  $789,000

  • 2 Beds
  • 3 Baths
  • 2,250 Sq Ft

  60 Spencer Hollow Rd, Springfield, VT 05156

  Experience timeless elegance and rural charm at this meticulously crafted country estate, featuring a historical reproduction Shaker-style home designed by renowned architect McKee Wing Roth and built in 1991. Set on 15 deeded acres of rolling pastures, this unique estate blends traditional design with modern sustainability. Conveniently located 6.5 miles from the renowned Crown Point Country

  Kristen Breeden Southern Vermont Realty Group

  60 Spencer Hollow Rd, Springfield, VT 05156
• 

  

  /17

  $49,000

  • Land
  • 1.31 Acres
  • $37,405 per Acre

  1-61 Hawk Spur Rd, Plymouth, VT 05056

  Affordable lot in a convenient Plymouth Lakes Region location, close to all area amenities including skiing and golf at nearby Okemo and Killington Mountain Resorts. Enjoy all four seasons in the quiet community of Hawk West. On-site septic system and drilled well will be needed. Hawk Resort covenants are in place to protect your investment. Come build your Vermont dream home!

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  1-61 Hawk Spur Rd, Plymouth, VT 05056
• 

  

  /13

  $50,000

  • Land
  • 1.5 Acres
  • $33,333 per Acre

  2-63 Goshawk Dr, Plymouth, VT 05056

  Affordable opportunity to build your dream home in a quiet neighborhood located between Okemo and Killington Mountain Resorts, with nearby access to Echo Lake, Hawk Resort hiking trails, and Plymouth State Park. With utilities close by and the ability to connect to the community wastewater system, this lot is ready for your new Vermont home. Community covenants and design standards help protect

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  2-63 Goshawk Dr, Plymouth, VT 05056
• 

  

  /44

  $95,000

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

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

  Jackson Gore Adams Hous at Okemo Mountain Resort. Quarter Share Ownership, Unit 238 QI is a true four-season destination offering a rare combination of slope-side convenience, year-round recreation, and resort-style amenities. With quarter-share ownership, you can enjoy the benefits of mountain living without the full-time commitment. This slopeside two-bedroom, two-bathroom corner condominium

  Joseph Karl William Raveis Real Estate Vermont Properties

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

  

  /17

  $53,000

  • Land
  • 1.5 Acres
  • $35,333 per Acre

  2-66 Goshawk Dr, Plymouth, VT 05056

  Dreaming of building your own Vermont-style home but hoping to find an affordable parcel? This lot at Hawk Resort is the perfect opportunity. With power and other utilities already on site and the ability to connect to the community septic system, you’ll be well on your way to breaking ground on your dream home. Tucked among the trees in a peaceful natural setting, this property offers privacy

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  2-66 Goshawk Dr, Plymouth, VT 05056
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  /31

  $995,000

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

  26 Mount Peg Rd Unit B, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit B, Woodstock, VT 05091
• 

  

  /28

  $995,000

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

  26 Mount Peg Rd Unit C, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit C, Woodstock, VT 05091
• 

  

  /32

  $1,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,592 Sq Ft

  26 Mount Peg Rd Unit A, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit A, Woodstock, VT 05091
• 

  

  /31

  $1,195,000

  • 3 Beds
  • 3.5 Baths
  • 2,385 Sq Ft

  26 Mount Peg Rd Unit D, Woodstock, VT 05091

  Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

  Mary Mayhew Snyder Donegan Real Estate Group

  26 Mount Peg Rd Unit D, Woodstock, VT 05091
• 

  

  /37

  $55,000

  • 1 Bath
  • 390 Sq Ft

  212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149

  Jackson Gore Inn at Okemo Mountain Resort. Quarter Share Ownership, Unit 212 Quarter III is a true four-season destination offering a rare combination of slope-side convenience, year-round recreation, and resort-style amenities. With quarter-share ownership, you can enjoy the benefits of mountain living without the full-time commitment. This studio condominium is located in the Jackson Gore Inn

  Kevin Barnes William Raveis Real Estate Vermont Properties

  212 QIII Jackson Gore Inn Unit 212 QIII, Ludlow, VT 05149

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