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    Windsor County, VT Hotels for Sale

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    Burlington, VT Bennington, VT Brattleboro, VT
    Historic Inn Near Ski Resorts
    $2,400,000

    Historic Inn Near Ski Resorts

    2 Dublin Road, Plymouth, VT 05149

    Full-service Vermont inn near Okemo and Killington ski resorts.

    • Prime location on Route 100, between Okemo Mountain Resort (±4 miles) and Killington Resort (±12 miles).
    • Historic, full‑service Vermont inn with a longstanding operating history.
    • Striking lakeside setting.
    • Benefits from year‑round tourism: skiing, lake recreation, weddings, and destination travel.
    • Scalable business model with potential for revenue growth.
    Updated: Apr 3
    View details
    Iconic Fullerton Inn For Sale
    $1,495,000
    18,896 SF

    Iconic Fullerton Inn For Sale

    40 The Common, Chester, VT 5143

    Southern Vermont hospitality landmark in historic downtown Chester.

    • Iconic, fully established turnkey inn business in historic downtown Chester.
    • Prime location on 2.28 acres with Williams River access.
    • 20 guest rooms/suites plus two owner/manager apartments.
    • Multiple dining areas (main dining room, secondary dining area, tavern/bar) and large rear deck.
    • Professional commercial kitchen for full restaurant operation and catered events.
    Updated: Apr 26
    View details
    Based on your search, we've compiled 35 Potential Opportunities for your consideration. Besides 2 Active listings in Windsor County, VT, we suggest exploring several alternatives: similar 29 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.

    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 Street, Ludlow, VT 05149
    View details
    Grantham Commercial Land Opportunity
    $875,000
    13.43 Acres

    Grantham Commercial Land Opportunity

    13.4-acre commercial parcel at high-traffic intersection near I-89.

    0 Rt 10, Grantham, NH 03753
    View details
    Prime Commercial Land Opportunity
    $650,000
    13.37 Acres

    Prime Commercial Land Opportunity

    Visible commercial land near major highway with diverse development potential.

    75 Rockingham Road, Londonderry, NH 03053
    View details
    Highway Visible Development Opportunity, Littleton
    $1,800,000
    6.94 Acres

    Highway Visible Development Opportunity, Littleton

    6.94 AC commercial land parcel with highway visibility.

    337 Cottage Street, Littleton, NH 03561
    View details

    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.

    287 Rte 100

    287 Rte 100

    HOTEL-RESORT • 8,882 SF
    Value Estimation
    $845,000
    287 Rte 100, Weston, VT 05161-5402
    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
    121 Ballardvale Dr

    121 Ballardvale Dr

    HOTEL • 54,350 SF
    Value Estimation
    $8,250,000
    121 Ballardvale Dr, White River Junction, VT 05001-7175
    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
    3 Church St

    3 Church St

    HOTEL-RESORT • 9,558 SF
    Value Estimation
    $3,015,000
    3 Church St, Woodstock, VT 05091-1214
    View details
    26 Main St

    26 Main St

    HOTEL-RESORT • 6,232 SF
    Value Estimation
    $710,000
    26 Main St, Windsor, VT 05089-1308
    View details
    102 Ballardvale Dr

    102 Ballardvale Dr

    HOTEL • 35,034 SF
    Value Estimation
    $5,605,000
    102 Ballardvale Dr, White River Junction, VT 05001-7008
    View details
    2206 Grn Mtn Tpke

    2206 Grn Mtn Tpke

    HOTEL-RESORT • 6,976 SF
    Value Estimation by Request
    2206 Grn Mtn Tpke, Chester, VT 05143-8525
    View details
    81 Happy Vly Rd

    81 Happy Vly Rd

    HOTEL-RESORT • 4,754 SF
    Value Estimation
    $700,000
    81 Happy Vly Rd, Woodstock, VT 05091
    View details
    362 Uppr Rd

    362 Uppr Rd

    HOTEL-RESORT • 5,653 SF
    Value Estimation
    $660,000
    362 Uppr Rd, Bridgewater Corners, VT 05035-4207
    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
    633 Main St

    633 Main St

    HOTEL-RESORT • 2,610 SF
    Value Estimation by Request
    633 Main St, Weston, VT 05161-5503
    View details
    41 Pleasant St

    41 Pleasant St

    HOTEL-RESORT • 5,993 SF
    Value Estimation
    $1,490,000
    41 Pleasant St, Woodstock, VT 05091-1146
    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
    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
    153 Pembroke Rd

    153 Pembroke Rd

    HOTEL-RESORT • 15,002 SF
    Value Estimation
    $690,000
    153 Pembroke Rd, Windsor, VT 05089-9029
    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
    2940 Rte 103

    2940 Rte 103

    HOTEL • 46,352 SF
    Value Estimation
    $1,505,000
    2940 Rte 103, Proctorsville, VT 05153-9100
    View details
    4771 Rte 100a

    4771 Rte 100a

    HOTEL-RESORT • 3,720 SF
    Value Estimation by Request
    4771 Rte 100a, Plymouth, VT 05056-9471
    View details
    52 Uppr Rd

    52 Uppr Rd

    HOTEL-RESORT • 5,028 SF
    Value Estimation by Request
    52 Uppr Rd, Bridgewater, VT 05034
    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

    Windsor County, VT Hotels Investment Opportunities Market Analysis

    Explore 31 hotels for sale in Windsor County, VT on our real estate platform. These investment opportunities span a total of 18,896 square feet of properties for sale, with an estimated market value of $1,495,000.

    Sale prices for resorts in Windsor County, VT start at $1,495,000, averaging $1,495,000, and reaching up to $1,495,000 — 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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