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    Windsor County, VT Hospitality Properties 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
    Woodstock Village Inn Opportunity
    $2,599,000
    0.46 Acres

    Woodstock Village Inn Opportunity

    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: Aug 12, 2025
    View details
    Turnkey Village Inn and Restaurant
    $1,350,000
    6,069 SF

    Turnkey Village Inn and Restaurant

    Fully furnished inn and restaurant near Okemo Mountain Ski Resort.

    86 Main Street, Ludlow, VT 5149
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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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    Barnard Inn: Event and Wedding Venue
    $2,675,000

    Barnard Inn: Event and Wedding Venue

    Charming inn and event venue near Woodstock, Vermont.

    West Woodstock, VT 05091
    View details
    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.

    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
    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, Ludlow, VT 05149
    View details
    50-Acre Commercial Land Opportunity
    $995,000
    50.60 Acres

    50-Acre Commercial Land Opportunity

    50 acres near Dartmouth Medical Center with development potential.

    24 Labombard Road, Lebanon, NH 03766
    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

    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.

    4189 Stony Brk Rd

    4189 Stony Brk Rd

    CAMPGROUND, RV PARK • 1,248 SF
    Value Estimation by Request
    4189 Stony Brk Rd, Stockbridge, VT 05772-4431
    View details
    288 Graves Rd

    288 Graves Rd

    CAMPGROUND, RV PARK • 43.70 Acres
    Value Estimation by Request
    288 Graves Rd, Baltimore, VT 05143
    View details
    687 Maple St

    687 Maple St

    MOTEL • 12,992 SF
    Value Estimation
    $1,475,000
    687 Maple St, White River Junction, VT 05001-8129
    View details
    1653 Woodstock Rd

    1653 Woodstock Rd

    MOTEL • 6.05 Acres
    Value Estimation
    $8,275,000
    1653 Woodstock Rd, Woodstock, VT 05091-3128
    View details
    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
    290 Densmore Hl Rd

    290 Densmore Hl Rd

    CAMPGROUND, RV PARK • 943 SF
    Value Estimation by Request
    290 Densmore Hl Rd, Windsor, VT 05089
    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
    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
    4324 Woodstock Rd

    4324 Woodstock Rd

    MOTEL • 1.04 Acres
    Value Estimation
    $965,000
    4324 Woodstock Rd, Woodstock, VT 05091-3313
    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
    172 Birch Tree Cir

    172 Birch Tree Cir

    CAMPGROUND, RV PARK • 2.03 Acres
    Value Estimation by Request
    172 Birch Tree Cir, Woodstock, VT 05091-7927
    View details
    908 Woodstock Rd

    908 Woodstock Rd

    MOTEL • 1.51 Acres
    Value Estimation
    $1,155,000
    908 Woodstock Rd, Woodstock, VT 05091-3645
    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
    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
    6739 Pomfret Rd

    6739 Pomfret Rd

    CAMPGROUND, RV PARK • 762.95 Acres
    Value Estimation by Request
    6739 Pomfret Rd, North Pomfret, VT 05053-5076
    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 6,069 square feet of properties for sale, with an estimated market value of $1,350,000.

    Sale prices for hospitality properties in Windsor County, VT start at $1,350,000, averaging $1,350,000, and reaching up to $1,350,000 — 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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