Investing in Annapolis, MD — Market Analysis
Annapolis prices in the middle of the Maryland market, with a median home price around $600,000. Annapolis is a coastal market, which changes the underwriting in two specific ways: insurance is a far larger line item than an inland comp, and windstorm or flood coverage may be written separately from the hazard policy. Both flow directly into your DSCR ratio.
Buying a rental property in Annapolis on a DSCR loan means putting a minimum of $120,000 down (20% of purchase price), leaving a loan amount of $480,000 at 80% LTV. At current DSCR investor pricing near 7.50%, principal and interest on that loan runs about $3,356 per month. Add Anne Arundel County property taxes of roughly $530/month, landlord insurance of about $460/month, and an HOA/master-association allowance of $180/month, and your all-in PITIA lands near $4,526/month. That PITIA figure — not the P&I — is what the lender divides your rent into.
A long-term lease in Annapolis should generate roughly $2,575/month in gross rent. Against a PITIA of $4,526, that produces an estimated DSCR ratio of 0.57x. That is well below the 1.0 threshold on a long-term lease, which is typical for a market at this price point. Financing here generally works one of three ways — a larger down payment, a no-ratio DSCR product, or qualifying on short-term rental revenue instead of long-term rent.
If you intend to operate the property as a short-term rental, estimated gross nightly revenue in Annapolis is around $5,525/month across a full year. Lenders do not credit gross STR revenue dollar-for-dollar — they typically haircut it 25%–30% for vacancy, cleaning, platform fees, and management. Applying a 28% haircut gives an effective $3,978/month, or a DSCR ratio of 0.88x. Even on short-term revenue this is a tight file, so plan on a larger down payment or a no-ratio structure.
Two Maryland-specific items to build into your model: Maryland charges a state transfer and recordation tax at closing that varies by county and can add over 1% to acquisition cost, and Baltimore City requires rental licensing and lead certification on most pre-1978 stock. Ocean City and Deep Creek Lake drive the state's short-term rental revenue. In Annapolis specifically, effective property tax on investment property runs around 1.06% of value annually — about $6,360 a year at the median price — and landlord insurance near $5,520 a year.
On return metrics, Annapolis pencils to an estimated cap rate of 3.19% using a 62% NOI margin, and a gross rent multiplier of 19.4. Monthly cash flow on a long-term lease at 20% down is estimated at $1,951 negative. Negative cash flow at 20% down is common in appreciation-led markets; investors here typically increase the down payment, buy below median, add a unit, or run the property short-term to close the gap.

