Top 6 Maryland Markets for Real Estate Investors in 2027

Maryland packs a lot of strategies into a small footprint: a state capital on the Chesapeake, a planned community between Baltimore and Washington, a western-Maryland value market, a Frederick rental hub, an Eastern Shore rent story and the state's biggest beach destination. Home prices run from about $255,000 in Salisbury to about $670,000 in Annapolis (Redfin, 2026), and the “rent-to-price ratios” here are thin, between roughly 0.38% and 0.53% a month on the figures below, which can make clearing 1.00x harder on a DSCR deal, so the underwriting matters. Investors buying here typically finance with Maryland DSCR loans, which are qualified primarily based on the property rather than the borrower's personal income.

This breakdown uses market data collected as of October 2026, the most current snapshot available heading into next year's buying season. If you're evaluating a purchase in the final months of 2026, keep in mind that your first full year of rental income, appreciation, or short-term rental revenue lands in 2027 regardless of when you close. A deal you underwrite today is already a 2027 investing decision, just one made with the freshest data available right now.

Maryland administers no single statewide short-term rental license, according to Awning's 2026 Maryland guide, so the rules are set by each city and county: Annapolis requires a short-term rental permit through its Planning and Zoning office, Ocean City requires a city rental license, Frederick doesn't ban short-term rentals but may require a business license and a basic safety inspection, and combined taxes in Ocean City can reach 10% to 12%.

One pattern shows up in Redfin's “Compete Scores”: Columbia scores 86 out of 100 (“very competitive”) and Annapolis 71, while Salisbury sits at 44 and Ocean City at 29 (“not very competitive”), so the most competitive market in the state is a suburb and the least competitive is a resort.

Below, we break down six Maryland markets worth watching, using current data from Zillow, Redfin, BiggerPockets, and AirDNA.

Note: Home price appreciation and rent-growth figures below come from Zillow's Home Value Index (ZHVI), Redfin's median sale price data, and BiggerPockets' Market Finder, which use different methodologies and can vary from one another. Annapolis, Columbia and Frederick have no BiggerPockets figures here and rely on Zillow and Redfin, and BiggerPockets figures for Hagerstown and Salisbury cover the wider Hagerstown–Martinsburg (MD–WV) and Salisbury (MD–DE) metros. Redfin's search-data tables repeat across several of these cities, so they're treated as regional, not city-specific.

Annapolis, MD

Premium prices, premium STR revenue

Annapolis is the state capital and a sailing town on the Chesapeake, and it is the most expensive market on this list – with a short-term rental market that earns more per listing than the state's beach resort.

Pricing & Rent

• Zillow typical home value is $633,333, up 2.0% year-over-year, and homes go to pending in around 10 days, with 37.3% of sales above list price. Average rent is $2,398, up 2.1%, a rent-to-price ratio of roughly 0.38% a month.
  ‍Zillow · June 2026
• Redfin's median sale price was $669,557, up 1.2% year-over-year, and the median price per square foot is up 11.2% to $362. Homes took a median of 40 days to sell (unchanged) and closed at about 99.4% of list price, 29.9% sold above list, and Annapolis's Compete Score is 71, i.e. “very competitive.”
  ‍Redfin · August 2026

Why Investors Are Watching Annapolis

Redfin search data, which tracks home searches rather than actual moves, shows New York buyers looking at Annapolis more than any other metro, with a net inflow of 1,396, while Annapolis buyers themselves most often search Salisbury. First Street data on Redfin flags real climate exposure, with 12% of properties at risk of severe flooding over the next 30 years and 99% at major risk from severe wind, so insurance belongs in the underwriting. On the STR side, Awning reports that Annapolis requires a short-term rental permit through Planning and Zoning for hosts who rent out whole units.

Short-Term Rental Performance (AirDNA)

The AirDNA submarket for Annapolis posts a score of 46/100, with Investability (62) and Rental Demand (61) leading and the other subscores in the high 50s. Annual revenue per listing averages $52,258 (up 5.3% year-over-year), the highest of the six markets, with an average daily rate of $369.64 (up 3.4%) and occupancy of 48% (up 2.1%). Total active listings sit at 738, down 1.1% over the past year, and the top listings, historic Annapolis houses earning roughly $239K a year, show where the “premium” sits.

Financing note: Harpoon Capital offers industry leading DSCR Loans for properties in Annapolis and all throughout the market area. Check out our full DSCR Loans Program here, or if you want a quote on what terms look like today, fill out this two-minute form!

Sources: Zillow Home Value Index↗ · Redfin Housing Market↗ · Awning Maryland STR Guide↗ · AirDNA↗

Investor Takeaway: Annapolis combines the highest prices on the list with the highest STR revenue per listing and a rent-to-price ratio near 0.4%. Investors should generally underwrite it as a premium STR play, confirm the permit before they offer, and price flood and wind insurance into the deal.

Columbia, MD

Bidding wars and a thin STR field

Columbia is a planned community between Baltimore and Washington, and it is the most competitive buyer market in the state, i.e. homes average about 1% above list price and four offers on a typical home.

Pricing & Rent

• Zillow typical home value is $518,039, up 0.1% year-over-year, and homes go to pending in around 6 days, with 55.0% of sales above list price. Average rent is $2,304, up 2.8%, a rent-to-price ratio of roughly 0.44% a month.
  ‍Zillow · June 2026
• Redfin's median sale price was $509,663, up 0.5% year-over-year, with sales up 9.3% and homes taking a median of 25 days to sell (20 a year ago). Homes closed at about 101.2% of list price, 48.5% sold above list, only 21.6% saw price drops, and Columbia's Compete Score is 86, i.e. “very competitive.”
  ‍Redfin · August 2026

Why Investors Are Watching Columbia

Redfin reports that “hot homes” in Columbia sell for about 4% above list price and go pending in around 6 days, which is the fastest pace on this list, and its search data, which tracks home searches rather than actual moves, shows New York buyers looking at Columbia more than any other metro. However, a market that clears above asking price leaves little room for a discount, and a price per square foot that is down 7.1% suggests that the “sales mix,” not appreciation, is carrying the median. Flood risk is minor (2% of properties), and no STR rules were confirmed for Columbia.

Short-Term Rental Performance (AirDNA)

The AirDNA submarket for Columbia posts a score of 59/100, with Seasonality (94) at the top, Revenue Growth (69) and Rental Demand (67) in the middle, and Investability (46) the “soft spot.” Annual revenue per listing averages $24,946 (up 5.0% year-over-year), with an average daily rate of $123.80 (up 3.1%) and occupancy of 61% (up 4.4%), the strongest occupancy of the six markets. Total active listings sit at just 122, down 3.2%, so this is a thin field where a few standout listings, such as a farmhouse retreat earning $159K, carry the averages.

Financing note: Harpoon Capital offers industry leading DSCR Loans for properties in Columbia and all throughout the market area. Check out our full DSCR Loans Program here, or if you want a quote on what terms look like today, fill out this two-minute form!

Sources: Zillow Home Value Index↗ · Redfin Housing Market↗ · AirDNA↗

Investor Takeaway: Columbia is a fast, competitive long-term rental market with rising rents and a small STR field. Investors should generally expect to bid at or above list, underwrite the rent first, and treat the STR income as a “bonus” that depends on a few top listings.

Hagerstown, MD

Top STR score and soaring sales

Hagerstown sits in the Cumberland Valley of western Maryland, and it pairs the lowest prices in the Washington corridor with the highest AirDNA score on the list and the fastest sales growth.

Pricing & Rent

• Redfin's median sale price was $279,815, up 13.3% year-over-year, on sales that rose 30.6%, though homes took a median of 56 days to sell (45 a year ago). Homes closed at about 99.3% of list price, 30.1% sold above list, and Hagerstown's Compete Score is 57, i.e. “somewhat competitive.”
  ‍Redfin · August 2026
• BiggerPockets shows median rental income of $1,159, a median home price of $278,100, a rent-to-price ratio of 0.42%, and an affordability score of 29.10%. Growth Stats show 7.67% appreciation and 2.57% year-over-year rent growth, with population growing 1.38%, the fastest on this list.
  ‍BiggerPockets · 2026

Why Investors Are Watching Hagerstown

BiggerPockets points to a diverse economy built on healthcare, education and manufacturing, with Meritus Health among the major employers, and the city's historic properties and strategic location along major transportation routes support the rental pool. However, First Street data on Redfin rates the flood risk as “severe”, with 10% of properties exposed over the next 30 years, and a 56-day median time to sell, up from 45, shows that the price surge has slowed buyers down. No STR rules were confirmed for Hagerstown.

Short-Term Rental Performance (AirDNA)

The AirDNA submarket for Hagerstown posts a score of 87/100, with Seasonality (93) leading, Revenue Growth (81) and Rental Demand (73) in good shape, and Investability (67) and Regulation (61) the softer subscores. Annual revenue per listing averages $25,904 (up 4.3% year-over-year), with an average daily rate of $135.90 (up 3.1%) and occupancy of 58% (up 0.8%). Total active listings sit at 168, up 14.3% over the past year, the fastest supply growth on the list, so the opportunity is real but the field is filling, and leaders such as a 4-bedroom with an indoor pool ($145K a year) set a high bar.

Financing note: Harpoon Capital offers industry leading DSCR Loans for properties in Hagerstown and all throughout the market area. Check out our full DSCR Loans Program here, or if you want a quote on what terms look like today, fill out this two-minute form!

Sources: Redfin Housing Market↗ · BiggerPockets Market Finder↗ · AirDNA↗

Investor Takeaway: Hagerstown offers the most affordable entry in the Washington corridor with strong population growth and the highest STR score on the list. Investors should generally underwrite the long-term rent first, watch the 14.3% jump in STR listings, and price flood insurance into every deal.

Thinking About One of These Markets?

Get a same-day DSCR Loan quote for a specific deal, or browse the full Harpoon Capital DSCR Loan Program to see rates, LTV, and qualification details before you keep reading.

Frederick, MD

Steady demand and shrinking STR supply

Frederick is a historic city in central Maryland near Sugarloaf Mountain, and it offers steady rents, a mid-priced entry point and a short-term rental market where supply is shrinking while rates rise.

Pricing & Rent

• Zillow typical home value is $469,711, down 1.1% year-over-year, and homes go to pending in around 11 days, with 36.7% of sales above list price. Average rent is $2,205, up 2.0%, a rent-to-price ratio of roughly 0.47% a month.
  ‍Zillow · June 2026
• Redfin's median sale price was $444,706, up 2.2% year-over-year, with sales up 8.5% and homes taking a median of 44 days to sell (40 a year ago). Homes closed at about 99.8% of list price, 33.9% sold above list, and Frederick's Compete Score is 63, i.e. “somewhat competitive.”
  ‍Redfin · August 2026

Why Investors Are Watching Frederick

Zillow's index is down 1.1% while Redfin's median is up 2.2%, i.e. a reminder that a smoothed index and actual closings can point in different directions in the same month, and a price per square foot that is down 6.8% suggests a changing sales mix. First Street data on Redfin rates flood risk as “moderate”, with 11% of properties exposed and the risk increasing faster than the national average. On the STR side, Awning reports that Frederick doesn't ban short-term rentals but may require a general business license and a basic safety inspection, and Frederick County adds a hotel rental tax on top of the state tax.

Short-Term Rental Performance (AirDNA)

The AirDNA submarket for Frederick posts a score of 76/100, with Seasonality (89) and Rental Demand (88) leading, Regulation (66) in the middle, and Investability (57) and Revenue Growth (55) the softer subscores. Annual revenue per listing averages $32,354 (up 1.6% year-over-year), with an average daily rate of $166.12 (up 5.2%) and occupancy of 58% (down 2.4%), so the revenue gain is “rate-led.” Total active listings sit at 447, down 5.3%, and mountain-lodge listings such as Zigbone Farm Retreat ($306K a year) pull the top end well above the average.

Financing note: Harpoon Capital offers industry leading DSCR Loans for properties in Frederick and all throughout the market area. Check out our full DSCR Loans Program here, or if you want a quote on what terms look like today, fill out this two-minute form!

Sources: Zillow Home Value Index↗ · Redfin Housing Market↗ · Awning Maryland STR Guide↗ · AirDNA↗

Investor Takeaway: Frederick offers steady rents and mid-range prices in a market where STR supply is shrinking and rates are rising. Investors should generally underwrite the long-term rent as the base case, confirm the business license and inspection, and treat the STR side as rate-driven upside.

Salisbury, MD

Strong rents and slumping STR revenue

Salisbury is the hub of Maryland's Eastern Shore, with a healthcare and education economy – the best rent-to-price ratio on the list – and a short-term rental market that is currently moving the wrong way.

Pricing & Rent

• Redfin's median sale price was $255,111, up 2.0% year-over-year, the lowest on this list, though homes took a median of 66 days to sell (53 a year ago). Homes closed at about 97.1% of list price (down 1.6 points), 21.9% sold above list, and Salisbury's Compete Score is 44, i.e. “somewhat competitive.”
  ‍Redfin · June 2026
• BiggerPockets shows median rental income of $1,274, a median home price of $241,200, a rent-to-price ratio of 0.53%, the highest on this list, and an affordability score of 17.42%. Growth Stats show 5.65% appreciation and 6.17% year-over-year rent growth, with population growing 0.73%.
  ‍BiggerPockets · 2026

Why Investors Are Watching Salisbury

BiggerPockets points to healthcare, education and retail, with Peninsula Regional Medical Center among the major employers, and Redfin search data, which tracks home searches rather than actual moves, shows Washington buyers looking at Salisbury more than any other metro, with a net inflow of 2,556, followed by Philadelphia and New York. In the same data, Salisbury is the top destination for buyers in Annapolis, Columbia, Hagerstown and Frederick, though Redfin's Salisbury area includes the Ocean City coast, so some of that interest likely points at the beaches. However, a 66-day time to sell and a sale-to-list ratio that fell 1.6 points suggest that buyers have the upper hand, i.e. room to negotiate. No STR rules were confirmed for Salisbury.

Short-Term Rental Performance (AirDNA)

The AirDNA submarket for Salisbury posts a score of 48/100, with Investability (78) the high point, Revenue Growth (60) and Seasonality (59) in the middle, and Rental Demand (53) the soft spot. Annual revenue per listing averages $28,892 (down 4.5% year-over-year), with an average daily rate of $201.27 (up 1.7%) and occupancy of 48% (down 6.6%), the steepest occupancy drop on the list. Total active listings sit at 251, up 7.3%, so supply is growing while demand falls.

Financing note: Harpoon Capital offers industry leading DSCR Loans for properties in Salisbury and all throughout the market area. Check out our full DSCR Loans Program here, or if you want a quote on what terms look like today, fill out this two-minute form!

Sources: Redfin Housing Market↗ · BiggerPockets Market Finder↗ · AirDNA↗

Investor Takeaway: Salisbury offers the best rent-to-price ratio and the fastest rent growth on the list, with the weakest STR trend. Investors should generally buy it for the long-term rent and treat STR income as unproven until occupancy stabilizes.

Ocean City, MD

Boardwalk revenue and extreme flood risk

Ocean City is Maryland's beach market, with nearly 7,000 short-term rental listings, a boardwalk economy and the least competitive buyer market on the list, and it carries the most serious climate risk of the six markets!

Pricing & Rent

• Redfin's median sale price was $449,701, up 7.1% year-over-year, with the median price per square foot at $443, up 2.0%. Homes took a median of 80 days to sell (84 a year ago) and closed at about 97.1% of list price, only 12.4% sold above list, and Ocean City's Compete Score is 29, i.e. “not very competitive,” with multiple offers rare.
  ‍Redfin · August 2026

Why Investors Are Watching Ocean City

Redfin groups Ocean City with Salisbury for search data, which tracks home searches rather than actual moves, and shows Washington buyers looking at the area more than any other metro (2,556), ahead of Philadelphia and New York. Awning reports that Ocean City requires a city rental license, enforces noise, occupancy and parking standards, and that combined lodging and sales taxes can reach 10% to 12%. The risk story is just as important: First Street data on Redfin rates the flood risk in Ocean City as “extreme”, with 94% of properties exposed to severe flooding over the next 30 years, plus severe wind and extreme heat risk, so get flood and wind insurance quotes before you make an offer.

Short-Term Rental Performance (AirDNA)

The Ocean City submarket posts an AirDNA score of 42/100, with Investability (66) at the top, Regulation (58) and Rental Demand (54) in the middle, and Seasonality (43) the “soft spot,” which is what a “summer-peaked” market looks like. Annual revenue per listing averages $41,766 (up 0.8% year-over-year), with an average daily rate of $365.75 (up 2.6%) and occupancy of 53% (down 2.2%). Total active listings sit at 6,994, down 0.7%, so this is a large, mature market, and top listings such as Endless Summer Villas ($411K a year) show how much the best oceanfront properties can earn.

Financing note: Ocean City deals often qualify on TTM actuals or STR revenue projections given the seasonal revenue base, and Harpoon Capital offers industry leading DSCR Loans for properties throughout the market area. Check out our full DSCR Loans Program here, or if you want a quote on what terms look like today, fill out this two-minute form!

Sources: Redfin Housing Market↗ · Awning Maryland STR Guide↗ · AirDNA↗

Investor Takeaway: Ocean City offers beach revenue in a large, mature market with long selling times and extreme flood risk. Investors should generally underwrite on trailing twelve-month actuals, model the off-season, and treat insurance as a “make-or-break” line item.

Short-Term Rental Snapshot: All Six Markets at a Glance

_{Source: AirDNA, current as of 2026. Scores and figures reflect each market or submarket as defined by AirDNA and may not correspond 1:1 with city or county boundaries. As of October 2026}

A few patterns stand out. Annapolis out-earns Ocean City per listing ($52,258 versus $41,766), because its rate of $369.64 holds on 48% occupancy and its supply is shrinking, and Annapolis and Columbia both grew revenue, rates and occupancy while listings fell. Hagerstown has the highest score but also the fastest supply growth (+14.3%), while Salisbury is the only market where revenue and occupancy both fell by more than 4%. Ocean City's 6,994 listings are roughly nine times Annapolis's, which is why its per-listing figure sits below the capital's.

Which Maryland Market Fits Your Strategy?

Maryland's real estate landscape offers a strategy for nearly every type of investor:

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Market-level data is a starting point, not a substitute for underwriting the specific property, neighborhood, and rental strategy in front of you. Maryland leaves short-term rental regulation to its cities and counties, so confirm what's legal at your specific address before you close, and get flood and wind insurance quotes early in coastal and low-lying areas.

If you are ready to invest in one of these markets, start with our Maryland DSCR loans page.

‍_{Sources: Zillow Home Value Index & Rental data, Redfin housing market data, BiggerPockets Market Finder, AirDNA market and submarket data (airdna.co) and Awning Maryland STR regulations. Data collected as of October 2026, ahead of the 2027 investing season.}

Frequently Asked Questions

Do I need a statewide license to run a short-term rental in Maryland?

According to Awning, Maryland has no single statewide short-term rental license, so licensing is handled by the county or city. Maryland applies a 6% sales tax plus a county hotel rental tax to short-term rental income, and Ocean City adds a local room tax, with combined rates that can reach 10% to 12%. Confirm current rules with the local jurisdiction before you close.

Do I need a Maryland real estate license to buy an investment property there?

No. Out-of-state and first-time investors can buy investment property in Maryland without any license. A DSCR loan qualifies you primarily based on the property itself rather than your personal income or professional credentials, which is part of why it's such a common financing tool for out-of-state buyers.

What is a DSCR loan and how does it work for a Maryland rental property?

A DSCR (Debt Service Coverage Ratio) loan qualifies a property primarily based on the property (its value, value and location) relative to its mortgage payment, rather than the borrower's personal income or tax returns. If the property's projected or actual rent covers the mortgage payment (a DSCR of 1.00x or higher), it's generally easier to qualify, and Harpoon Capital also offers options for deals below 1.00x.

How risky is flooding in Ocean City for an investor?

First Street data on Redfin rates the flood risk in Ocean City as “extreme,” with 94% of properties at risk of severe flooding over the next 30 years, and its wind and heat risk as “severe” and “extreme.” A deal is still possible with that profile, but flood and wind insurance quotes should be in hand before you make an offer.

How much down payment do I need for a DSCR loan in Maryland?

Harpoon Capital's DSCR loan program allows as little as 15% down on qualifying purchases, up to 85% LTV, with cash-out refinances available up to 80% LTV. Exact terms depend on the property, credit profile, and DSCR ratio. Fill out our DSCR Loan Application to see specific numbers for your deal.

Ready to Run the Numbers on a Maryland Deal?

Whether you're eyeing Hagerstown's value entry or beach revenue in Ocean City, get a same-day rate and terms with our two-minute DSCR quote form, or explore the full Maryland DSCR Loans Program to see how we qualify the property, not just the borrower.

This article is for informational purposes only and does not constitute investment, legal, or financial advice. Harpoon Capital encourages investors to conduct independent due diligence before making any real estate investment decision.

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