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Chester, VT Hospitality Properties for Sale

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Victorian Multi-Family Home
$599,000
3,850 SF

Victorian Multi-Family Home

534 Elm St, Chester, VT 05143

Impressive Victorian home with carriage house in Chester, Vermont.

  • Main house features 4 bedrooms and a 3‑bedroom carriage house, offering flexibility.
  • Turnkey sale for immediate occupancy.
  • Located in Chester, Vermont, one of the top 10 most beautiful towns in Vermont.
  • Proximity to multiple Vermont ski resorts: Okemo, Killington, Stratton, Bromley, and Magic Mountains.
  • Historic Victorian home (built in 1868) with original character.
Updated: Dec 2, 2025
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Based on your search, we've compiled 15 Potential Opportunities for your consideration. Besides 1 Active listings in Chester, VT, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 10 Off-Market properties to explore as potential leads

Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Historic Vermont Inn - Ludlow
$1,690,000
6,069 SF

Historic Vermont Inn - Ludlow

Charming 9-room Inn, high ROI

86 Main St, Ludlow, VT 05149
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Turnkey Restaurant and Hotel Opportunity
$1,500,000
5,000 SF

Turnkey Restaurant and Hotel Opportunity

Four-season business in Okemo Mountain area, ready for new owner.

119 Main St, Ludlow, VT 05149
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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
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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
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Explore Off-Market Properties in Chester, VT

Consider similar Off-Market properties in Chester, 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.

270200 Old Shincracker

270200 Old Shincracker

CAMPGROUND, RV PARK • 47.00 Acres
Value Estimation
$240,000
270200 Old Shincracker, Chester, VT 05143
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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
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982 High St

982 High St

CAMPGROUND, RV PARK • 952 SF
Value Estimation
$280,000
982 High St, Chester, VT 05143
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40 Cmn St

40 Cmn St

HOTEL-RESORT • 18,896 SF
Value Estimation
$1,000,000
40 Cmn St, Chester, VT 05143
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2206 Grn Mtn Tpke

2206 Grn Mtn Tpke

HOTEL-RESORT • 6,976 SF
Value Estimation
$65,000
2206 Grn Mtn Tpke, Chester, VT 05143-8525
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698 Vt Rte 11th W

698 Vt Rte 11th W

HOTEL-RESORT • 6,848 SF
Value Estimation
$395,000
698 Vt Rte 11th W, Chester, VT 05143-8975
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Potash Brk Rd

Potash Brk Rd

CAMPGROUND, RV PARK • 10.50 Acres
Value Estimation
$235,000
Potash Brk Rd, Chester, VT 05143
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17 Pond Rd

17 Pond Rd

CAMPGROUND, RV PARK • 1.67 Acres
Value Estimation
$235,000
17 Pond Rd, Chester, VT 05143
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Andover Rd

Andover Rd

CAMPGROUND, RV PARK • 6.62 Acres
Value Estimation
$235,000
Andover Rd, Chester, VT 05143
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6558 Popple Dungeon Rd

6558 Popple Dungeon Rd

CAMPGROUND, RV PARK • 0.23 Acres
Value Estimation
$260,000
6558 Popple Dungeon Rd, Chester, VT 05143
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Chester, VT Hospitality Properties Investment Opportunities Market Analysis

Explore 11 hospitality properties for sale in Chester, VT on our real estate platform. These investment opportunities span a total of 5,869,710 square feet of properties for sale, with an estimated market value of $2,509,000.

Prices for hospitality properties in Chester, VT start at $235,000, averaging $501,800, and reaching up to $1,000,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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