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    Windsor County, VT Hospitality Properties for Sale

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    12 properties
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    Historic Bed & Breakfast Estate
    Updated: Jul 31
    Historic Bed & Breakfast Estate

    1589 Main Street, Cavendish, VT 05142

    $1,400,000
    2.40 AC lot
    2.4+/- landscaped acres in Cavendish, Vermont
    10‑bedroom mansion dating to 1860
    Five bedrooms with ensuite baths plus a private owner’s apartment
    Renovated 3,000‑square‑foot barn for events of up to 125 guests
    Listed on the National Historic Register
    View details
    8-Room Bed & Breakfast Inn
    Updated: Aug 12, 2025
    8-Room Bed & Breakfast Inn

    Wood Stock, VT 05091

    $2,599,000
    0.46 AC lot
    Eight‑room inn with an additional one‑bedroom owner’s quarters
    Built in 1899 on 0.46 acres
    Post‑and‑beam and wood‑frame construction
    Non‑residential zoning with public water and propane utility service
    Metal roof and basement space
    View details
    Resort Property with Lodging
    Resort Property with Lodging

    184 Hartland Hill Road, Hartland, VT 05048

    $1,699,000
    40.00 AC lot

    Wooded Vermont retreat property with guest accommodations, a lodge, walking trails, and infrastructure for hosted stays.

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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    Historic Bed And Breakfast Estate
    Historic Bed And Breakfast Estate

    1589 Main St, Cavendish, VT 05142

    $1,400,000
    5,500 sqft 2.40 AC lot

    Historic hospitality property with an event barn, chef’s kitchen, and multiple spaces for guest gatherings and celebrations.

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    Historic Lakeside Hotel
    Historic Lakeside Hotel

    2 Dublin Road, Plymouth, VT 05149

    $2,400,000

    Full-service Vermont inn along Route 100 near Okemo Mountain Resort and Killington Resort.

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    Furnished Short-Term Rental Retreat
    Furnished Short-Term Rental Retreat

    544 Vulture Mountain Road, Stockbridge, VT 05772

    $500,000
    960 sqft 1.20 AC lot

    Turnkey mountain retreat with multiple guest accommodations, furnished interiors, and established short-term rental operations.

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    Renovated Mixed-Use Property with Guest Rooms
    Renovated Mixed-Use Property with Guest Rooms

    52 Upper Road, Bridgewater, VT 05035

    $749,000
    1.50 AC lot

    Classic Vermont property combines restaurant infrastructure, lodging accommodations, outdoor seating, and separate living quarters.

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    Iconic Fullerton Inn For Sale
    Iconic Fullerton Inn For Sale

    40 The Common, Chester, VT 05143

    $1,495,000
    18,896 sqft 2.28 AC lot

    Southern Vermont hospitality landmark in historic downtown Chester.

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    Historic Bed And Breakfast
    Historic Bed And Breakfast

    505 Deweys Mills Road, Hartford, VT 05047

    $1,275,000
    0.90 AC lot

    Antique lodging property with updated interiors, water views, and access to nearby trails.

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    Killington Sunrise Base Lodge & Mountain
    Killington Sunrise Base Lodge & Mountain

    170 VT Route 100, Bridgewater, VT 05035

    $4,200,000
    8,841 sqft

    Historic Killington property with recreational business and development potential.

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    Charming Inn in Woodstock, VT
    Charming Inn in Woodstock, VT

    Wood Stock, VT 05091

    $2,599,000
    0.46 AC lot

    8-room Inn with owner's quarters in vibrant Woodstock, VT.

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    Glamping Campground with Farm Buildings
    Glamping Campground with Farm Buildings

    481 Parker Hill Rd, Springfield, VT 05156

    $985,000
    10.00 AC lot

    Fully permitted glamping grounds on 10 acres with a restored farmhouse, bath house, and multiple on-site structures.

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    Based on your search, we've compiled 72 Potential Opportunities for your consideration. Besides 12 Active listings in Windsor County, VT, we suggest exploring several alternatives: similar 60 Off-Market properties to explore as potential leads

    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
    CAMPGROUND, RV PARK

    4189 Stony Brk Rd, Stockbridge, VT 05772-4431

    Estimated value:
    $265,000
    1,248 sqft 0.94 AC lot
    View details
    288 Graves Rd
    CAMPGROUND, RV PARK

    288 Graves Rd, Baltimore, VT 05143

    Estimated value:
    $230,000
    43.70 AC lot
    View details
    687 Maple St
    MOTEL

    687 Maple St, White River Junction, VT 05001-8129

    Estimated value:
    $1,475,000
    12,992 sqft 1.00 AC lot
    View details
    1653 Woodstock Rd
    MOTEL

    1653 Woodstock Rd, Woodstock, VT 05091-3128

    Estimated value:
    $8,275,000
    6.05 AC lot
    View details
    287 Rte 100
    HOTEL-RESORT

    287 Rte 100, Weston, VT 05161-5402

    Estimated value:
    $845,000
    8,882 sqft 5.10 AC lot
    View details
    91 Ballardvale Dr
    HOTEL

    91 Ballardvale Dr, White River Junction, VT 05001-7176

    Estimated value:
    $5,900,000
    96,364 sqft 4.65 AC lot
    View details
    121 Ballardvale Dr
    HOTEL

    121 Ballardvale Dr, White River Junction, VT 05001-7175

    Estimated value:
    $8,250,000
    54,350 sqft
    View details
    290 Densmore Hl Rd
    CAMPGROUND, RV PARK

    290 Densmore Hl Rd, Windsor, VT 05089

    Estimated value:
    $250,000
    943 sqft 10.01 AC lot
    View details
    698 Vt Rte 11th W
    HOTEL-RESORT

    698 Vt Rte 11th W, Chester, VT 05143-8975

    Estimated value:
    $395,000
    6,848 sqft 5.63 AC lot
    View details
    3 Church St
    HOTEL-RESORT

    3 Church St, Woodstock, VT 05091-1214

    Estimated value:
    $2,925,000
    9,558 sqft 1.95 AC lot
    View details
    26 Main St
    HOTEL-RESORT

    26 Main St, Windsor, VT 05089-1308

    Estimated value:
    $695,000
    6,232 sqft 1.10 AC lot
    View details
    1092 Sessions Mdw
    CAMPGROUND, RV PARK

    1092 Sessions Mdw, Woodstock, VT 05091-7928

    Estimated value:
    $55,000
    1.50 AC lot
    View details

    Windsor County, VT Hospitality Properties Market Trends and Statistics

    Explore 72 hospitality properties for sale in Windsor County, VT, showcased through 12 active listings on our real estate platform. These investment opportunities span a total of 34,197 square feet of properties for sale, with an estimated market value of $21,301,000.

    Sale prices for hospitality properties in Windsor County, VT start at $500,000, averaging $1,775,083, and reaching up to $4,200,000 — 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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    Featured Windsor County Real Estate Agencies

    Realmo connects you with licensed Windsor County CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Dunrovin Real Estate
    PO Box 450 Royalton, VT 05068
    Phone: 18027637177
    dunrovincountryvermont.com
    Snyder Donegan Real Estate Group
    PO Box 161, 5 The Green West Woodstock, VT 05091
    Phone: 18024572600
    www.snyderdonegan.com
    Bassette Real Estate Group
    611 Route 12 Hartland, VT 05048
    Phone: 18024572244
    www.vermontcountryrealestate.com

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