Windsor County, VT Hospitality properties for sale

$549,900

960 SF

Mountain Cabin Compound

544 Vulture Mountain Road, Stockbridge, VT 05772

Seasonal short-term rental compound with multiple cabins and a restored travel trailer, set on 1.2 acres in Vermont.

1.2‑acre VT mountain retreat with proven seasonal short‑term rental operation from May through October
Includes main cottage built in 1964 plus 2 guest cabins and a restored 21‑foot Sunset travel trailer
Communal gathering setup with a large deck and outdoor kitchen for entertaining and guest use
Heating/cooling includes electric heat, ductless systems, zoned cooling, a wood stove, natural gas, and propane
Utilities and services: propane available, well water, and on‑demand water heater

Updated: May 13

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$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

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$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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$2,675,000

10.00 Acres

Barnard Inn: Event and Wedding Venue

Charming inn and event venue near Woodstock, Vermont.

West Woodstock, VT 05091

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Based on your search, we've compiled 72 Potential Opportunities for your consideration. Besides 4 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.

$4,500,000

127.00 Acres

Mountain-Adjacent Development Land

127-acre Ludlow parcel with a move-in-ready 4-bedroom home, supporting residential development and year-round recreation access.

85 Pallottas Hill, Ludlow, VT 05149

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$875,000

13.43 Acres

Business District Development Land

Commercially zoned land at a high-traffic intersection, well suited for a range of business development concepts.

Rt 10, Grantham, NH 03753

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$815,000

13.00 Acres

Airbnb Investment Property in Vermont

13-acre property with rental cabins and yurts near I-89.

429 Community Drive, Randolph, VT 05061

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$195,000

52,272 SF

Vermont Land Near Pikes Falls

1.2-acre parcel near Pikes Falls with development potential.

4769 Pikes Falls Road, Jamaica, VT 5343

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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.

CAMPGROUND, RV PARK

1,248 SF Lot: 0.94 Acres

Value Estimation by Request

4189 Stony Brk Rd, Stockbridge, VT 05772-4431

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CAMPGROUND, RV PARK

Lot: 43.70 Acres

Value Estimation by Request

288 Graves Rd, Baltimore, VT 05143

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MOTEL

12,992 SF Lot: 1.00 Acre

Estimated value

$1,475,000

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

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MOTEL

Lot: 6.05 Acres

Estimated value

$8,275,000

1653 Woodstock Rd, Woodstock, VT 05091-3128

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HOTEL-RESORT

8,882 SF Lot: 5.10 Acres

Estimated value

$845,000

287 Rte 100, Weston, VT 05161-5402

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HOTEL

96,364 SF Lot: 4.65 Acres

Estimated value

$5,900,000

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

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HOTEL

54,350 SF

Estimated value

$8,250,000

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

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CAMPGROUND, RV PARK

943 SF Lot: 10.01 Acres

Value Estimation by Request

290 Densmore Hl Rd, Windsor, VT 05089

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HOTEL-RESORT

6,848 SF Lot: 5.63 Acres

Value Estimation by Request

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

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HOTEL-RESORT

9,558 SF Lot: 1.95 Acres

Estimated value

$3,015,000

3 Church St, Woodstock, VT 05091-1214

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HOTEL-RESORT

6,232 SF Lot: 1.10 Acres

Estimated value

$710,000

26 Main St, Windsor, VT 05089-1308

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CAMPGROUND, RV PARK

Lot: 1.50 Acres

Value Estimation by Request

1092 Sessions Mdw, Woodstock, VT 05091-7928

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MOTEL

Lot: 1.04 Acres

Estimated value

$965,000

4324 Woodstock Rd, Woodstock, VT 05091-3313

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HOTEL

35,034 SF Lot: 1.58 Acres

Estimated value

$5,605,000

102 Ballardvale Dr, White River Junction, VT 05001-7008

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CAMPGROUND, RV PARK

Lot: 2.03 Acres

Value Estimation by Request

172 Birch Tree Cir, Woodstock, VT 05091-7927

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MOTEL

Lot: 1.51 Acres

Estimated value

$1,155,000

908 Woodstock Rd, Woodstock, VT 05091-3645

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CAMPGROUND, RV PARK

Lot: 97.10 Acres

Value Estimation by Request

2999 Baltimore Rd, Baltimore, VT 05143-9575

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HOTEL-RESORT

6,976 SF Lot: 35.00 Acres

Value Estimation by Request

2206 Grn Mtn Tpke, Chester, VT 05143-8525

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CAMPGROUND, RV PARK

Lot: 762.95 Acres

Value Estimation by Request

6739 Pomfret Rd, North Pomfret, VT 05053-5076

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HOTEL-RESORT

4,754 SF Lot: 0.73 Acres

Estimated value

$700,000

81 Happy Vly Rd, Woodstock, VT 05091

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Windsor County, VT Hospitality Properties Investment Opportunities Market Analysis

Explore 68 hospitality properties for sale in Windsor County, VT, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 25,925 square feet of properties for sale, with an estimated market value of $3,394,900.

Sale prices for hospitality properties in Windsor County, VT start at $549,900, averaging $1,131,633, 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.