Windsor County VT Homes for Sale

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  /19

  $359,000

  • 4 Beds
  • 3 Baths
  • 2,144 Sq Ft

  25 Independent Dr, Hartland, VT 05048

  Affordable, Large multi family building on 6.36+/- acres currently being used as 3 units but has a 4th unit which will need to be finished and updated. This property has lots of space and many options for rental revenue. Add this property to your rental portfolio and rent all four units or Live on site in one unit and have the other three units help pay for your living expenses. This property is

  Alex DeFelice The Clerkin Agency, P.C.

  25 Independent Dr, Hartland, VT 05048
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  /27

  $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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  /10

  $1,625,000

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

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001

  New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts,

  Richard Higgerson Higgerson & Company

  7074 Robert Frost Ln Unit 7074, Hartford, VT 05001
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  /16

  $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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  /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. 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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  /21

  $99,000

  • Land
  • 1.8 Acres
  • $55,000 per Acre

  142 Brooks Rd, Ludlow, VT 05149

  Discover the perfect setting for your dream home on this peaceful 1.8-acre parcel in Ludlow. This private, wooded lot offers a serene natural backdrop and features the calming presence of Grant Brook, adding both beauty and the soothing sounds of flowing water to your future homesite. With access to public water already available, much of the groundwork for development is simplified; a septic

  Daniel Preston KW Vermont Woodstock

  142 Brooks Rd, Ludlow, VT 05149
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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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  /47

  $650,000 Open Sun 10AM - 12PM

  • 4 Beds
  • 2 Baths
  • 2,496 Sq Ft

  2170 Wildlife Rd, White River Junction, VT 05001

  Additional photos forthcoming. Are you looking for your perfect Vermont family home, or a getaway with huge AirBnB potential? Located just outside the bustle of the Upper Valley and close to outdoor activities like ski mountains, hiking, and mountain biking, this house boasts an incredible turn-key value for buyers looking to move in right away or use it as an income-producing property. The

  Sal Cania BHHS Verani Upper Valley

  2170 Wildlife Rd, White River Junction, VT 05001
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  /60

  $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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  /36

  $699,900

  • 4 Beds
  • 4 Baths
  • 3,780 Sq Ft

  5 Malagash Rd, South Reading, VT 05153

  Set on a spacious and level lot in the scenic countryside of Reading, Vermont, this raised ranch offers room to spread out both inside and out. With 4 bedrooms and 4 bathrooms, the home provides flexible living options across two levels—perfect for larger households, multi-generational living, or hosting guests. The bright main floor features an open layout with a comfortable living area, an

  Katie Ladue Gilbert KW Vermont Woodstock

  5 Malagash Rd, South Reading, VT 05153
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  /37

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,092 Sq Ft

  1782 Blackmer Blvd, Stockbridge, VT 05772

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

  Kyle Kershner Killington Pico Realty

  1782 Blackmer Blvd, Stockbridge, VT 05772
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  /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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  /31

  $585,000

  • 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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  /25

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft

  724 S Windsor St, South Royalton, VT 05068

  Welcome to this beautifully updated Central Vermont home offering excellent potential as a primary residence or investment opportunity. This versatile property is ideally located less than 1 mile to Vermont Law School and just 0.5 miles to WRV Elementary and High Schools. Enjoy walking distance to the Village Green with year-round farmers markets and community events. The half-acre property

  Katie Ladue Gilbert KW Vermont Woodstock

  724 S Windsor St, South Royalton, VT 05068
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  /56

  $715,000

  • 3 Beds
  • 2 Baths
  • 2,542 Sq Ft

  333 Music Mountain Rd, Stockbridge, VT 05772

  Nestled on a hilltop above scenic Music Mountain Road, this exceptional architect-designed home offers a private, sunny setting with breathtaking long-range views. The open floor plan provides one-level living ideal for every lifestyle, with radiantly heated white oak floors, a striking carved-oak mantel fireplace, and French doors framing the mountain panorama. The chef’s kitchen features

  Kyle Kershner Killington Pico Realty

  333 Music Mountain Rd, Stockbridge, VT 05772
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  /46

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft

  55 Trickle Brook Dr, Cavendish, VT 05142

  Welcome to 55 Trickle Brook Drive, a charming and well-designed home offering three bedrooms and two full bathrooms, being sold fully furnished, and ideally located just about 10 minutes from Okemo Mountain and close to the Proctor-Piper State Forest. This inviting property blends comfort, functionality, and year-round recreation, with nearby access to hiking, mountain biking, and snowmobiling

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  55 Trickle Brook Dr, Cavendish, VT 05142
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  /57

  $1,175,000

  • 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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  /6

  $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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  /9

  $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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  /60

  $2,895,000

  • 5 Beds
  • 9 Baths
  • 8,249 Sq Ft

  1497 Bowman Rd, Barnard, VT 05068

  Upper Farm- Circa 1799, large antique cape nestled on 12 acres with stream, multiple ponds, stunning waterfalls overlooking a large meadow. Beautiful extensive gardens for all those perennial enthusiasts with multiple stone terraces overlooking an apple orchard with a variety of types of apples. A two level barn for equipment/storage/animals. A brand new expansive 3 bay heated garage with

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  1497 Bowman Rd, Barnard, VT 05068
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  /60

  $799,000

  • 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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  /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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  /43

  $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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  /45

  $895,000

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  72 Oakridge Way, Woodstock, VT 05091

  PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot.

  Nancy Greenwood Watson Realty & Associates

  72 Oakridge Way, Woodstock, VT 05091
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  /38

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 1,974 Sq Ft

  85 Rimrock Rd Unit 13A, Ludlow, VT 05149

  Excellent value priced to sell - Prime location, ski-on, ski-off with direct access to Sachem Trail, with just a few steps from your door, and you'll be on the slopes! This is a bright and sunny condo featuring 3 bedrooms, 2.5 bathrooms, and a loft. The living and dining area features a cathedral ceiling, a wood-burning fireplace, and a deck offering a long-distance view. Recent updates include

  Karen Wilson TPW Real Estate

  85 Rimrock Rd Unit 13A, Ludlow, VT 05149
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  /46

  $74,000

  • 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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