Windsor County VT Homes for Sale

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  $3,250,000

  • 5 Beds
  • 6.5 Baths
  • 5,728 Sq Ft

  191 Moon Shadow Dr Unit M19, Ludlow, VT 05149

  Solitude home at the top of the hill awaits! Solitude on Okemo Mountain, where this exceptional five-bedroom home captures the ultimate ski location, breathtaking long-range views, and unparalleled privacy. Perfectly positioned to embrace the beauty of the surrounding mountains, this residence offers a rare opportunity to enjoy true slope-side living in one of Vermont’s most sought-after resort

  Katherine Burns William Raveis Real Estate Vermont Properties

  191 Moon Shadow Dr Unit M19, Ludlow, VT 05149
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  $70,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  434 Qtr. I Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn, Unit 434 Q I. Quarter Ownership. This top floor residence has beautiful valley facing views. Unit B Features: one bedroom with king bed, queen sleep sofa and queen wall bed, full kitchen, jetted tub, fireplace, entertainment center. This unit sleeps six and includes 1 locker for year round use. Other features include a large master bath offering his and her sinks, gas fireplace

  Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

  434 Qtr. I Jackson Gore Inn, Ludlow, VT 05149
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  /2

  $269,000

  • Land
  • 13.9 Acres
  • $19,353 per Acre

  1 Barbara Lee Ln, Norwich, VT 05055

  Tucked off a quiet country lane in desirable Norwich, this 13.9 acre parcel offers a beautiful blend of privacy, convenience, and thoughtfully advanced planning. Just 10 minutes to center village and Dan & Whit’s, the land features a mostly level, roughed-in driveway approach and a peaceful setting ideal for a serene Vermont lifestyle. EC Fiber is available at the road for modern connectivity. A

  Kris Lippi Get Listed Realty

  1 Barbara Lee Ln, Norwich, VT 05055
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  $1,245,000

  • 3 Beds
  • 4 Baths
  • 2,971 Sq Ft

  42 Deerfield Dr, Ludlow, VT 05149

  Welcome to South Hill Overlook on Deerfield Drive. This perfectly situated, idyllic country home boasts a beautifully appointed interior and sweeping views of Okemo and the surrounding mountains, with a sophisticated three-bedroom, four-bath contemporary design that blends luxury and comfort-ideal as either a primary residence or a vacation retreat. This sun-filled home was built by one of the

  Kevin Barnes William Raveis Real Estate Vermont Properties

  42 Deerfield Dr, Ludlow, VT 05149
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  $115,000

  • Land
  • 5 Acres
  • $23,000 per Acre

  3200 Baltimore Rd, Chester, VT 05143

  This lovely open lot offers many possibilities for future use. Facing South, the land is 80% open and bordered by beautiful stonewalls and mature Maple trees. The long range Mountain views are visible from many different locations on the land. A wonderful opportunity to own a piece of Vermont, nestled in the Green Mountains.

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  3200 Baltimore Rd, Chester, VT 05143
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  $500,000

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

  M-17 Moonshadow Dr, Ludlow, VT 05149

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

  Katherine Burns William Raveis Real Estate Vermont Properties

  M-17 Moonshadow Dr, Ludlow, VT 05149
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  $495,000

  • 2 Beds
  • 3 Baths
  • 2,091 Sq Ft

  85 Townhouse Way Unit 14, Woodstock, VT 05091

  Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  85 Townhouse Way Unit 14, Woodstock, VT 05091
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  /13

  $1,625,000 New Construction

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

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001

  To be built at Mountain Stream in Quechee Lakes, the 3,079-square-foot Aspen model offers three levels of flexible living space. The main level features double-height living, dining, and kitchen areas with fireplace, terrace access, mudroom, mechanical room, half bath, one bedroom with walk-in closet, and a primary suite. The second level includes a family room, full bathroom, and an additional

  Richard Higgerson Higgerson & Company

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001
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  $96,232 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  11 Cubb Ct, Windsor, VT 05089

  Welcome to 11 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

  Kate Barry EXP Realty

  11 Cubb Ct, Windsor, VT 05089
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  $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. Presently, all three units are vacant. Easy to show! There is good

  Glenn Olney Barrett and Valley Associates Inc.

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

  $175,000

  • 3 Beds
  • 3 Baths
  • 1,854 Sq Ft

  705/707 Qtr I V Adams House, Ludlow, VT 05149

  Adams 705/707 Quarter IV: Quarter ownership. This top floor, 3 bedroom unit is in a wonderful location with magical mountain views up the Jackson Gore Peak! This is a lockout condominium with two bedrooms on one side and one bedroom on the lockout side with incredible ski access. The large Primary Bedroom boasts a King sized Bed, a fireplace and beautiful en-suite bathroom. The second bedroom has

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

  705/707 Qtr I V Adams House, Ludlow, VT 05149
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  $136,000

  • Land
  • 2.85 Acres
  • $47,719 per Acre

  0 Quechee Main St Unit 5076706, Hartford, VT 05059

  Rare opportunity to build in the heart of Quechee Village without a Club membership. This exceptional 2.5-acre lot is beautifully sited overlooking Lake Pinneo, with seasonal views of the Quechee Ski Hill, offering a quintessential Vermont setting in a highly desirable location. Tucked in at the center of the village, the property combines privacy, scenery, and walkable convenience, an

  Brooks Reavill

  0 Quechee Main St Unit 5076706, Hartford, VT 05059
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  /2

  $89,500

  • Land
  • 0.98 Acre
  • $91,327 per Acre

  430 Jay Hill Rd, Hartford, VT 05001

  This is the place where your Vermont story begins. 0.98 wooded acres on Jay Hill Road in Quechee—not just land, but an invitation into one of New England's most thoughtful communities. What makes this different? Property ownership includes membership in the Quechee Club. That means 36 holes of championship golf across the Lakeland and Highland courses. It means Ski Quechee (13 trails, free for

  Richard Higgerson Higgerson & Company

  430 Jay Hill Rd, Hartford, VT 05001
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  $800,000

  • 7 Beds
  • 4.5 Baths
  • 4,733 Sq Ft

  107 Baker Rd, Springfield, VT 05156

  Welcome to this spacious and beautifully expanded Gambrel-style home, nestled on a breathtaking 9.55-acre property with sweeping mountain views in the heart of Springfield, Vermont. Combining classic New England charm with thoughtful modern upgrades, this property is more than just a home; it's a vibrant lifestyle. The main house, built in 1955, was thoughtfully enhanced with a large addition in

  Jeremy Collins Ridgeline Real Estate

  107 Baker Rd, Springfield, VT 05156
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  $229,000

  • 4 Beds
  • 1.5 Baths
  • 2,214 Sq Ft

  2404 Tarbell Hill Rd, Cavendish, VT 05142

  This new to the market home is a must see for location alone: 15 minutes to Okemo gets you skiing all day, or hiking and camping in the state forests. With over 2200 square feet and 3-4 bedrooms, (town has 4 bedrooms, one is accessed by 2 other bedrooms or mudroom could be a bedroom for the count of 4) there is plenty of room for everyone. The living space on the first level is incredible with a

  Christine Lewis Brattleboro Area Realty

  2404 Tarbell Hill Rd, Cavendish, VT 05142
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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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  $545,000

  • 3 Beds
  • 3 Baths
  • 3,062 Sq Ft

  32 Plumley Ave, Ludlow, VT 05149

  This is a neat spot. Close enough to the village that you can walk to shops and restaurants but just far enough out that you enjoy the peace and quiet of a dead-end road. The house sits up from the road which means that you get to enjoy some views of Okemo. If you would rather not drive up to the mountain, you can walk to the end of the street and hop on Okemo's shuttle. Built in 1993, this home

  Betty McEnaney Diamond Realty

  32 Plumley Ave, Ludlow, VT 05149
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  $485,000

  • 4 Beds
  • 4 Baths
  • 2,977 Sq Ft

  7471 US Route 4, Bridgewater, VT 05034

  This property is conveniently located in Bridgewater Village, situated midway between Woodstock and the Killington Ski Area. While currently configured as three income-producing units, it offers an outstanding opportunity for a creative conversion back into a single-family residence, with the detached rear unit available to supplement the cost of ownership. Recent updates include a new roof,

  Bonnie Bergeron Snyder Donegan Real Estate Group

  7471 US Route 4, Bridgewater, VT 05034
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  $1,395,000

  • 5 Beds
  • 3.5 Baths
  • 4,214 Sq Ft

  28 Mountain View Dr, Ludlow, VT 05149

  Stunning contemporary home with a Vermont feel. This five-bedroom, three-and-a-half-bath home offers ample living space for all your guests. Three levels feature bright, beautiful rooms and an amazingly spacious, totally renovated kitchen with room for all of the chefs. The living room's focal point is the floor-to-ceiling stone fireplace, featuring a cathedral ceiling, sliders to the deck (with

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

  28 Mountain View Dr, Ludlow, VT 05149
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  $1,075,000

  • 4 Beds
  • 3 Baths
  • 2,892 Sq Ft

  145 Russell Rd, Cavendish, VT 05142

  Thinking of building your dream home, finding a perfect contractor & designer? Well skip the headaches. Move right in - Here are the keys! Tucked on 12.9 serene acres, custom built in 2024, this 4-bedroom, 3-bathroom amazing home combines expert craftsmanship and design with modern comfort and sweeping mountain VIEWS. Start your mornings with breathtaking vistas and end your evenings with family

  Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

  145 Russell Rd, Cavendish, VT 05142
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  $119,000

  • Land
  • 10.66 Acres
  • $11,163 per Acre

  00 Norrie Davies Rd, Cavendish, VT 05142

  This property is in two parcels, see survey. The 5.82 acre parcel with the pond sets between Tarbell Hill Rd and Norrie Davies Rd. The 4.84 acre building lot parcel is directly across and is entirely on Norrie Davies Rd. The building lot is wooded with 1200+ feet of road frontage and has a state permit for a 4 bedroom septic system. The lovely pond offer a pleasant place to relax and enjoy.

  Frank Ellison Ellison Real Estate, Inc.

  00 Norrie Davies Rd, Cavendish, VT 05142
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  $125,000

  • Land
  • 0.07 Acre
  • $1,785,714 per Acre

  83 Main St, Ludlow, VT 05149

  Prime downtown location! Once home to one of the few stone houses in Ludlow. Walk to everything on Main St. The lot is in the preservation district and may be deemed unbuildable do diligence will be required to determine properties usability. Town Planners suggested a public charging station? First of it's kind in Ludlow!

  Frank Provance Diamond Realty

  83 Main St, Ludlow, VT 05149
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  $1,195,000

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

  513 Deer Brook Way, Woodstock, VT 05091

  Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions,

  Keri Cole Williamson Group Sothebys Intl. Realty

  513 Deer Brook Way, Woodstock, VT 05091
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  $775,000

  • 7 Beds
  • 7 Baths
  • 4,581 Sq Ft

  7137 US Route 4, Bridgewater, VT 05034

  Welcome to the historic Bridgewater Inn — a rare, turn-key Vermont property perfectly positioned between Woodstock Village, Killington Resort, and Okemo Mountain. This unique offering features a spacious 3-bedroom, 3-bath main home along with four fully equipped guest suites, creating exceptional flexibility for full-time living, multi-generational use, or continued short-term rental success. The

  Benjamin Cote EXP Realty

  7137 US Route 4, Bridgewater, VT 05034
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  /31

  $219,000

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

  107 Litchfield St, Springfield, VT 05156

  Welcome to this charming home on Litchfield Street. Offering convenient in-town living but with a country feel with privacy in the back and side yard! Sitting high above a scenic stream, you can enjoy the water view as you sit on the spacious back deck! More room than you might think, with two nice bedrooms down and a third bedroom upstairs with a half bath. The full bath is on the first floor

  Glenn Olney Barrett and Valley Associates Inc.

  107 Litchfield St, Springfield, VT 05156
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  $65,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  264/266 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

  Experience the ultimate blend of convenience and flexibility with this rare one-bedroom lockout at the prestigious Jackson Gore Inn. Offering the space and amenities of a larger suite with the strategic layout of two separate units, this property is a powerhouse for both personal retreats and rental potential.Designed to maximize every square foot, this unit comfortably sleeps 8 guests—an

  Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

  264/266 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
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  $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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  $750,000

  • 2 Beds
  • 3 Baths
  • 1,364 Sq Ft

  193 Jackson Gore Unit 739/741, Ludlow, VT 05149

  Come and experience Vermont at its best! This condo is located in Jackson Gore on Okemo Mountain in Ludlow. This slope side condo unit has stunning views of the mountain and trails. This unit would serve well as a family retreat or rental investment property. It boasts a gas fireplace for cold winter nights. It has 2 bedrooms and 3 bathrooms and offers lock-out capability for separate rental

  John Napier TPW Real Estate

  193 Jackson Gore Unit 739/741, Ludlow, VT 05149
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  $67,500

  • 1 Bed
  • 2 Baths
  • 1,011 Sq Ft

  714/716 QIII Jackson Gore Adams House Rd Unit 714/716 QIII, Ludlow, VT 05149

  Experience the ultimate in mountain living with this top-floor one-bedroom, two-bathroom Jackson Gore Adams House condominium on Okemo Mountain. This quartershare ownership offers you a carefree, luxury resort lifestyle with direct ski-on/ski-off access and all the amenities of Jackson Gore Village. The spacious condo comfortably sleeps eight, featuring two fixed queen beds, a queen wall bed, and

  Kevin Barnes William Raveis Real Estate Vermont Properties

  714/716 QIII Jackson Gore Adams House Rd Unit 714/716 QIII, Ludlow, VT 05149

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