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    Chestertown, MD
    Bed & Breakfast

    Chestertown, MD Bed & Breakfasts for Sale

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    Turnkey Bed and Breakfast Inn
    Updated: Apr 11
    Turnkey Bed and Breakfast Inn

    25227 Chestertown Road, Chestertown, MD 21620

    Contact for pricing
    20.00 AC lot
    Brampton Bed and Breakfast on a 20‑acre property
    Beautifully restored 1860 Eastern Shore manor house
    13 ensuite refined lodgings
    Parking included in the list price
    Located about 2 miles from historic Chestertown
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    Turn Any Listing Into an Investment Snapshot Owner equity, real caprate, demand score for every listing. Go To Analytics Center
    Based on your search, we've compiled 9 Potential Opportunities for your consideration. Besides 1 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 4 Land Listings that present a potential for development.

    Opportunities in Nearby Cities

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

    Brick Bed and Breakfast Building
    Brick Bed and Breakfast Building

    343 CARLISLE STREET, Gettysburg, PA 17325

    $499,900
    13,532 sqft

    Two-story brick building with 17 bedrooms and multiple living and meeting spaces for hospitality or residential-style uses.

    View details
    Restaurant and Bed & Breakfast
    Restaurant and Bed & Breakfast

    900 Chambersburg Road, Gettysburg, PA 17325

    $1,495,000

    Full-service fine dining tavern with a 10-room B&B, banquet/wedding facility, and a full R liquor license.

    View details
    2.03 Acres on Route 340
    2.03 Acres on Route 340

    847 Berryville Pike, Charles Town, WV 25414

    $795,000

    2.03 acres with high visibility and commercial zoning.

    View details
    Inn and Spa with Restaurant
    Inn and Spa with Restaurant

    4490 Summit Point Rd, Charles Town, WV 25414

    Contact for pricing

    Inn and spa property with 19 suites, a full service spa, and a remodeled commercial kitchen restaurant in five buildings.

    View details

    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.

    Land with Rental Income Potential
    Land with Rental Income Potential

    1021-1025-1029 S 47 Route lot: 37,38,36, Rio Grande, NJ 08242

    $1,299,900

    Large parcel zoned for business with existing rental income.

    View details
    Waterfront Multifamily with Marina Slips
    Waterfront Multifamily with Marina Slips

    555 N Maryland Ave, Atlantic City, NJ 08401

    $1,200,000

    Waterfront multifamily with commercial marina zoning, 5 deep-water boat slips, and updated roof, boiler, and HVAC.

    View details
    Land on Route 3
    Land on Route 3

    Mary Ball Road, White Stone, VA 22578

    $45,000
    2.00 AC lot

    Two-acre lot with road frontage, potential for B&B.

    View details
    Pocono Lake Acreage Opportunity
    Pocono Lake Acreage Opportunity

    Oak Leaf Ln 25, Pocono Lake, PA 18347

    Contact for pricing
    1.06 AC lot

    1+ acre lot near Poconos attractions, short-term rental potential.

    View details

    Chestertown, MD Bed & Breakfasts Market Trends and Statistics

    Explore 1 bed & breakfasts for sale in Chestertown, MD on our real estate platform. These investment opportunities span a total of 0 square feet of properties for sale, with an estimated market value of $0.00.

    Sale prices for inns in Chestertown, MD start at $0.00, averaging $0.00, and reaching up to $0.00 — 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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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Bed & breakfasts 1

    Demographics Overview

    Population 14K
    Population Growth (5Y) +2.9%
    Median Household Income $76,094
    College Educated 32.4%

    Taxes & Financing

    Tax Rate (average for all types) 1.34%
    Property Tax per SF $23.81 per SF
    Tax Rate vs County Average 0.07 pp above county avg
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Kent County

    New Delisted

    Property Size Breakdown

    The majority of commercial real estate listings in Chestertown fall within the 10,000 to 25,000 square foot range.

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