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    Windham County, VT Hospitality Properties for Sale

    7 results
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    Historic Sitzmark Venue with Acreage
    $749,000
    38.40 Acres

    Historic Sitzmark Venue with Acreage

    54 East Dover Rd, Wilmington, VT 05363

    Restaurant, indoor/outdoor bars, tennis, pool, disc golf on 38.4 acres.

    • 46 acres of land offer development potential and space for various activities.
    • Includes restaurant setup, indoor and outdoor bars, tennis courts, and a pool.
    • Features disc golf (formerly a traditional golf course).
    • Historically a center of a thriving ski community and snowmobile hub.
    • Venue previously hosted bands and entertainment.
    Updated: Jan 14
    View details
    Turnkey Entertainment Destination on Route 100
    $859,800
    0.75 Acres

    Turnkey Entertainment Destination on Route 100

    179 Rte 100 North, Wilmington, VT 05363

    Established entertainment destination with bowling, mini golf, restaurant, and living quarters.

    • Turnkey commercial property with established business, multiple revenue streams, and strong community ties.
    • High‑visibility location on Route 100 with strong traffic counts and easy access.
    • Six candlepin bowling lanes with new lanes and updated equipment.
    • Year‑round 18‑hole mini golf course and arcade area.
    • Pizza restaurant with seating, delivery options, and a fully equipped bar with full liquor service.
    Updated: Jan 9
    View details
    Southern Vermont Lodge Near Skiing
    $1,590,000
    2.25 Acres

    Southern Vermont Lodge Near Skiing

    Family-friendly lodge with amenities near ski lifts.

    344 Vt Rte 100, West Dover, VT 05356
    View details
    Renovated Estate Near Mount Snow
    $1,150,000
    3.97 Acres

    Renovated Estate Near Mount Snow

    Renovated 8-bedroom estate near Mount Snow, ideal for retreats.

    5 Tannery Rd, West Dover, VT 05356
    View details
    Unique Vermont Property with Views
    $1,100,000
    35.00 Acres

    Unique Vermont Property with Views

    Versatile property near Mount Snow, Stratton, and Jamaica villages.

    35 Fawn Ledge Ln, Jamaica, VT 05343
    View details
    Vermont Multi-Family with Guest Cottage
    $899,000
    5,480 SF

    Vermont Multi-Family with Guest Cottage

    Historic property with two dwellings and a guest cottage.

    3732 Vt Route 30, Jamaica, VT 05343
    View details
    Vermont Inn & Farm for Sale
    $2,000,000
    8,278 SF

    Vermont Inn & Farm for Sale

    Luxury Vermont B&B, 7 bedrooms, 6.5 acres.

    251 Pratt Bridge Rd, Jamaica, VT 05343
    View details
    Based on your search, we've compiled 104 Potential Opportunities for your consideration. Besides 7 Active listings in Windham County, VT, we suggest exploring several alternatives: similar 94 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.

    Forested Land with Mountain Views
    $210,000
    30.10 Acres

    Forested Land with Mountain Views

    30.1-acre forested parcel in Jamaica, VT with mountain views.

    184 School House Rd, Jamaica, VT 05343
    View details
    Forested Land Parcel with Mountain Views
    $210,000
    30.10 Acres

    Forested Land Parcel with Mountain Views

    30.1+/- acre parcel in Jamaica, VT with mountain views.

    184 School House Rd, Jamaica, VT 05343
    View details
    Wooded Land in Jamaica, Vermont
    $98,000
    10.00 Acres

    Wooded Land in Jamaica, Vermont

    10.2-acre wooded lot with road frontage in Jamaica, VT.

    1105 South Hill Rd, Jamaica, VT 05343
    View details

    Explore Off-Market Properties in Windham County, VT

    Consider similar Off-Market properties in Windham 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.

    251 Pratt Bridge Rd

    251 Pratt Bridge Rd

    Bed & breakfasts • 8,278 SF
    Value Estimation by Request
    251 Pratt Bridge Rd, Jamaica, VT 05343
    View details
    441 Magic Mtn Access Rd

    441 Magic Mtn Access Rd

    Motels • 27,404 SF
    Value Estimation by Request
    441 Magic Mtn Access Rd, Londonderry, VT 05148
    View details
    872 Stonehouse Rd

    872 Stonehouse Rd

    CAMPGROUND, RV PARK • 2.00 Acres
    Value Estimation
    $255,000
    872 Stonehouse Rd, Jacksonville, VT 05342-9774
    View details
    53 Main St

    53 Main St

    HOTEL-RESORT • 3,168 SF
    Value Estimation
    $260,000
    53 Main St, Wilmington, VT 05363-9781
    View details
    195 Rte 9th W

    195 Rte 9th W

    MOTEL • 6,402 SF
    Value Estimation
    $455,000
    195 Rte 9th W, Wilmington, VT 05363
    View details
    10 Main St

    10 Main St

    HOTEL-RESORT • 21,033 SF
    Value Estimation
    $705,000
    10 Main St, Wilmington, VT 05363-9680
    View details
    508 Higley Hl Rd

    508 Higley Hl Rd

    HOTEL-RESORT • 5,704 SF
    Value Estimation
    $275,000
    508 Higley Hl Rd, Wilmington, VT 05363-9604
    View details
    34 Look Rd

    34 Look Rd

    MOTEL • 9,633 SF
    Value Estimation
    $500,000
    34 Look Rd, Wilmington, VT 05363-9625
    View details
    4071 Vt Rte 11

    4071 Vt Rte 11

    MOTEL • 4,066 SF
    Value Estimation
    $250,000
    4071 Vt Rte 11, Londonderry, VT 05148-9729
    View details
    6091 Westminster W Rd

    6091 Westminster W Rd

    CAMPGROUND, RV PARK • 6.00 Acres
    Value Estimation
    $265,000
    6091 Westminster W Rd, Westminster W, VT 05346-9349
    View details
    257 Stimpson Hl Rd

    257 Stimpson Hl Rd

    CAMPGROUND, RV PARK • 1.25 Acres
    Value Estimation
    $265,000
    257 Stimpson Hl Rd, Whitingham, VT 05361
    View details
    994 Fuller Hl Rd

    994 Fuller Hl Rd

    CAMPGROUND, RV PARK • 0.90 Acres
    Value Estimation
    $260,000
    994 Fuller Hl Rd, Whitingham, VT 05361-9793
    View details
    13 Walker Rd

    13 Walker Rd

    CAMPGROUND, RV PARK • 6.57 Acres
    Value Estimation
    $100,000
    13 Walker Rd, Athens, VT 05143-4458
    View details
    1254 Putney Rd

    1254 Putney Rd

    MOTEL • 10,296 SF
    Value Estimation
    $440,000
    1254 Putney Rd, Brattleboro, VT 05301-9062
    View details
    1235 Parsons Rd

    1235 Parsons Rd

    CAMPGROUND, RV PARK • 10.50 Acres
    Value Estimation
    $105,000
    1235 Parsons Rd, Jacksonville, VT 05342-9669
    View details
    Wilm Cross Rd

    Wilm Cross Rd

    CAMPGROUND, RV PARK • 1.75 Acres
    Value Estimation
    $230,000
    Wilm Cross Rd, Whitingham, VT 05361
    View details
    418 Howard Hl Rd

    418 Howard Hl Rd

    CAMPGROUND, RV PARK • 1.40 Acres
    Value Estimation
    $265,000
    418 Howard Hl Rd, Chester, VT 05143-4474
    View details

    Windham County, VT Hospitality Properties Investment Opportunities Market Analysis

    Explore 101 hospitality properties for sale in Windham County, VT, showcased through 7 active listings on our real estate platform. These investment opportunities span a total of 32,954,881 square feet of properties for sale, with an estimated market value of $33,358,800.

    Prices for hospitality properties in Windham County, VT start at $90,000, averaging $555,980, and reaching up to $2,090,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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