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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: Feb 24
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    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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    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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    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
    View details
    Based on your search, we've compiled 72 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 3 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.

    Main Street Commercial Opportunity, Ludlow
    $450,000
    1.43 Acres

    Main Street Commercial Opportunity, Ludlow

    Blank canvas with Village/Residential zoning on Ludlow's Main Street.

    8 Main St, Ludlow, VT 05149
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    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
    View details
    127 Acres Near Okemo Mountain
    $4,500,000
    127.00 Acres

    127 Acres Near Okemo Mountain

    127-acre parcel near Okemo Mountain, suitable for development.

    85 Pallottas Hill Rd, Ludlow, VT 05149
    View details

    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.

    52 Upper Rd

    52 Upper Rd

    Hotels • 1.50 Acres
    Value Estimation by Request
    52 Upper Rd, Bridgewater, VT 05035
    View details
    583 Woodstock Rd

    583 Woodstock Rd

    MOTEL • 3,478 SF
    Value Estimation by Request
    583 Woodstock Rd, White River Junction, VT 05001-7015
    View details
    2458 Webster Hl Rd

    2458 Webster Hl Rd

    CAMPGROUND, RV PARK • 144.39 Acres
    Value Estimation by Request
    2458 Webster Hl Rd, Pomfret, VT 05068-9001
    View details
    W

    W

    CAMPGROUND, RV PARK • 0.26 Acres
    Value Estimation by Request
    W, Hartford, VT 05084
    View details
    1792 Quechee Main St

    1792 Quechee Main St

    HOTEL-RESORT • 6,681 SF
    Value Estimation
    $770,000
    1792 Quechee Main St, Quechee, VT 05059-3176
    View details
    171 Castle Hl Dr

    171 Castle Hl Dr

    HOTEL • 13,926 SF
    Value Estimation
    $845,000
    171 Castle Hl Dr, Cavendish, VT 05142
    View details
    Andover Rd

    Andover Rd

    CAMPGROUND, RV PARK • 6.62 Acres
    Value Estimation by Request
    Andover Rd, Chester, VT 05143
    View details
    1092 Sessions Mdw

    1092 Sessions Mdw

    CAMPGROUND, RV PARK • 1.50 Acres
    Value Estimation by Request
    1092 Sessions Mdw, Woodstock, VT 05091-7928
    View details
    91 Ballardvale Dr

    91 Ballardvale Dr

    HOTEL • 96,364 SF
    Value Estimation
    $5,900,000
    91 Ballardvale Dr, White River Junction, VT 05001-7176
    View details
    399 Depot St

    399 Depot St

    HOTEL-RESORT • 7,476 SF
    Value Estimation by Request
    399 Depot St, Proctorsville, VT 05153-9708
    View details
    75 Mtn Vw

    75 Mtn Vw

    CAMPGROUND, RV PARK • 5.00 Acres
    Value Estimation by Request
    75 Mtn Vw, Baltimore, VT 05143
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    104 Ballardvale Dr

    104 Ballardvale Dr

    HOTEL • 52,120 SF
    Value Estimation
    $4,560,000
    104 Ballardvale Dr, White River Junction, VT 05001-7008
    View details
    39 Main St

    39 Main St

    HOTEL • 51,950 SF
    Value Estimation
    $1,910,000
    39 Main St, White River Junction, VT 05001-7094
    View details
    696 Deweys Mls Rd

    696 Deweys Mls Rd

    HOTEL-RESORT • 5,932 SF
    Value Estimation
    $610,000
    696 Deweys Mls Rd, Hartford, VT 05047
    View details
    40 Cmn St

    40 Cmn St

    HOTEL-RESORT • 18,896 SF
    Value Estimation
    $900,000
    40 Cmn St, Chester, VT 05143
    View details
    2999 Baltimore Rd

    2999 Baltimore Rd

    CAMPGROUND, RV PARK • 97.10 Acres
    Value Estimation by Request
    2999 Baltimore Rd, Baltimore, VT 05143-9575
    View details
    430 Old Piper Rd

    430 Old Piper Rd

    CAMPGROUND, RV PARK • 60.00 Acres
    Value Estimation by Request
    430 Old Piper Rd, Baltimore, VT 05143
    View details
    698 Vt Rte 11th W

    698 Vt Rte 11th W

    HOTEL-RESORT • 6,848 SF
    Value Estimation by Request
    698 Vt Rte 11th W, Chester, VT 05143-8975
    View details
    106 Apothecary Ln

    106 Apothecary Ln

    HOTEL-RESORT • 5,041 SF
    Value Estimation by Request
    106 Apothecary Ln, Windsor, VT 05089-1326
    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.

    Sale 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 stay ahead with the latest data and market trends.

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