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    Windsor County, VT Hospitality Properties for Sale

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    Woodstock Village Inn Opportunity
    $2,599,000
    0.46 Acres

    Woodstock Village Inn Opportunity

    41 Pleasant St, Wood Stock, VT 05091

    Charming 8-room Inn with owner's quarters in Woodstock, Vermont.

    • Established 8‑room Inn with a strong reputation and impressive revenue growth.
    • Includes a separate 1‑bedroom owner's quarters for convenient on‑site living.
    • Located in Woodstock, VT, recognized as one of America's most charming small towns and a popular tourist destination.
    • Features a cozy tavern and well‑regarded restaurant, enhancing guest experience and revenue potential.
    • Combines historic charm (built in 1899) with modern amenities.
    Updated: Jan 14
    View details
    Victorian Multi-Family Home
    $599,000
    3,850 SF

    Victorian Multi-Family Home

    534 Elm St, Chester, VT 05143

    Impressive Victorian home with carriage house in Chester, Vermont.

    • Main house features 4 bedrooms and a 3‑bedroom carriage house, offering flexibility.
    • Turnkey sale for immediate occupancy.
    • Located in Chester, Vermont, one of the top 10 most beautiful towns in Vermont.
    • Proximity to multiple Vermont ski resorts: Okemo, Killington, Stratton, Bromley, and Magic Mountains.
    • Historic Victorian home (built in 1868) with original character.
    Updated: Dec 2, 2025
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    Historic Vermont Inn - Ludlow
    $1,690,000
    6,069 SF

    Historic Vermont Inn - Ludlow

    Charming 9-room Inn, high ROI

    86 Main St, Ludlow, VT 05149
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    Historic Vermont Inn - $3.2M
    $3,200,000

    Historic Vermont Inn - $3.2M

    Charming Vermont Inn, Event Venue, Estate Potential

    5518 Vt-12, Woodstock, VT 05091
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    Turnkey Restaurant and Hotel Opportunity
    $1,500,000
    5,000 SF

    Turnkey Restaurant and Hotel Opportunity

    Four-season business in Okemo Mountain area, ready for new owner.

    119 Main St, Ludlow, VT 05149
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    Based on your search, we've compiled 73 Potential Opportunities for your consideration. Besides 5 Active listings in Windsor County, VT, we suggest exploring several alternatives: similar 64 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Killington Historic Sunrise Base Lodge
    $4,200,000
    309.24 Acres

    Killington Historic Sunrise Base Lodge

    Rare opportunity in Killington, Vermont's premier four-season resort town.

    170 Vt Route 100, Bridgewater, VT 05035
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    Main Street Commercial Opportunity, Ludlow
    $465,000
    1.43 Acres

    Main Street Commercial Opportunity, Ludlow

    Blank canvas with business, residential, and retail potential on Main Street.

    8 Main St, Ludlow, VT 05149
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    127 Acres Near Okemo Mountain
    $5,500,000
    127.00 Acres

    127 Acres Near Okemo Mountain

    Rare 127-acre development opportunity near Okemo Mountain in Ludlow, VT.

    85 Pallottas Hill Rd, Ludlow, VT 05149
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    Hartford Land with Drive-Thru Potential
    $825,000
    0.90 Acres

    Hartford Land with Drive-Thru Potential

    Commercial land suitable for retail, restaurant, or automotive businesses.

    1049 North Main St, White River Junction, VT 05001
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    Explore Off-Market Properties in Windsor County, VT

    Consider similar Off-Market properties in Windsor County, VT. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    86 Main St

    86 Main St

    Hospitality properties • 6,069 SF
    Value Estimation by Request
    86 Main St, Ludlow, VT 05149
    View details
    5518 Vt-12

    5518 Vt-12

    Hotels
    Value Estimation by Request
    5518 Vt-12, Woodstock, VT 05091
    View details
    5518 Barnard Vt 05031

    5518 Barnard Vt 05031

    Hotels • 7,619 SF
    Value Estimation by Request
    5518 Barnard Vt 05031, Woodstock, VT 05091
    View details
    52 Upper Rd

    52 Upper Rd

    Hotels • 1.50 Acres
    Value Estimation by Request
    52 Upper Rd, Bridgewater, VT 05035
    View details
    4189 Stony Brk Rd

    4189 Stony Brk Rd

    CAMPGROUND, RV PARK • 1,248 SF
    Value Estimation
    $265,000
    4189 Stony Brk Rd, Stockbridge, VT 05772-4431
    View details
    41 Pleasant St

    41 Pleasant St

    HOTEL-RESORT • 5,993 SF
    Value Estimation
    $1,445,000
    41 Pleasant St, Woodstock, VT 05091-1146
    View details
    362 Uppr Rd

    362 Uppr Rd

    HOTEL-RESORT • 5,653 SF
    Value Estimation
    $650,000
    362 Uppr Rd, Bridgewater Corners, VT 05035-4207
    View details
    1092 Sessions Mdw

    1092 Sessions Mdw

    CAMPGROUND, RV PARK • 1.50 Acres
    Value Estimation
    $55,000
    1092 Sessions Mdw, Woodstock, VT 05091-7928
    View details
    908 Woodstock Rd

    908 Woodstock Rd

    MOTEL • 1.51 Acres
    Value Estimation
    $1,250,000
    908 Woodstock Rd, Woodstock, VT 05091-3645
    View details
    270200 Old Shincracker

    270200 Old Shincracker

    CAMPGROUND, RV PARK • 47.00 Acres
    Value Estimation
    $240,000
    270200 Old Shincracker, Chester, VT 05143
    View details
    3196 Rte 5th 5

    3196 Rte 5th 5

    CAMPGROUND, RV PARK • 2,082 SF
    Value Estimation
    $270,000
    3196 Rte 5th 5, Springfield, VT 05156-9537
    View details
    5391 Rte 100

    5391 Rte 100

    CAMPGROUND, RV PARK • 6.40 Acres
    Value Estimation
    $240,000
    5391 Rte 100, Plymouth, VT 05056
    View details
    75 Mtn Vw

    75 Mtn Vw

    CAMPGROUND, RV PARK • 5.00 Acres
    Value Estimation
    $225,000
    75 Mtn Vw, Baltimore, VT 05143
    View details
    982 High St

    982 High St

    CAMPGROUND, RV PARK • 952 SF
    Value Estimation
    $280,000
    982 High St, Chester, VT 05143
    View details
    26 Main St

    26 Main St

    HOTEL-RESORT • 6,232 SF
    Value Estimation
    $695,000
    26 Main St, Windsor, VT 05089-1308
    View details
    52 Uppr Rd

    52 Uppr Rd

    HOTEL-RESORT • 5,028 SF
    Value Estimation
    $265,000
    52 Uppr Rd, Bridgewater, VT 05034
    View details
    2940 Rte 103

    2940 Rte 103

    HOTEL • 46,352 SF
    Value Estimation
    $1,015,000
    2940 Rte 103, Proctorsville, VT 05153-9100
    View details
    430 Old Piper Rd

    430 Old Piper Rd

    CAMPGROUND, RV PARK • 60.00 Acres
    Value Estimation
    $110,000
    430 Old Piper Rd, Baltimore, VT 05143
    View details
    104 Ballardvale Dr

    104 Ballardvale Dr

    HOTEL • 52,120 SF
    Value Estimation by Request
    104 Ballardvale Dr, White River Junction, VT 05001-7008
    View details

    Windsor County, VT Hospitality Properties Investment Opportunities Market Analysis

    Explore 69 hospitality properties for sale in Windsor County, VT, showcased through 5 active listings on our real estate platform. These investment opportunities span a total of 44,169,403 square feet of properties for sale, with an estimated market value of $51,808,000.

    Prices for hospitality properties in Windsor County, VT start at $55,000, averaging $1,036,160, and reaching up to $8,275,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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