Boats for Sale in Chester, MD
27+ new and used boats from dealers in Chester, Maryland. Updated daily.
27 boats available
Used
2006 Regulator 29FS
$124,990
353' LOA 500 HP Center Console
Chester, MD
Used
2019 Sea Chaser 24 HFC
$68,900
285' LOA 280 HP Center Console
Chester, MD
Used
2020 Everglades 435CC
$399,000
512' LOA 1275 HP Center Console
Chester, MD
New
2026 Steiger Craft 255 Miami
Price N/A
306' LOA 300 HP Boat
Chester, MD
Used
2017 Everglades 355 Center Console
$299,900
424' LOA 900 HP Center Console
Chester, MD
New
2026 Steiger Craft 28 Annapolis
Price N/A
336' LOA 500 HP Boat
Chester, MD
Used
1997 Formula 382 FASTech
$99,999
458' LOA 1000 HP Bowrider
Chester, MD
Used
2013 Everglades 295CC
$149,900
371' LOA 600 HP Center Console
Chester, MD
Used
2013 EdgeWater 318CC
$119,900
387' LOA 600 HP Center Console
Chester, MD
Used
2015 Everglades 243CC
$89,000
291' LOA 300 HP Center Console
Chester, MD
Used
2018 Regulator 31
$299,900
372' LOA 300 HP Center Console
Chester, MD
Used
2019 Apex A-24
$56,900
288' LOA 300 HP Boat
Chester, MD
Used
2020 Everglades 273CC
$169,900
327' LOA 500 HP Center Console
Chester, MD
Used
2021 Sea Ray SDX 270 Outboard
$117,990
324' LOA 300 HP Bowrider
Chester, MD
Used
2023 Steiger Craft 31 Chesapeake
$319,900
372' LOA 600 HP Boat
Chester, MD
Used
2023 Everglades 395CC
$799,900
468' LOA 1275 HP Center Console
Chester, MD
New
2025 Monterey M-45
$99,999
288' LOA 250 HP Bowrider
Chester, MD
New
2025 Everglades 253CC
Price N/A
322' LOA 400 HP Center Console
Chester, MD
New
2026 Steiger Craft 28 Fisherman
Price N/A
336' LOA 600 HP Center Console
Chester, MD
New
2026 Key West Boats 291 FS
Price N/A
349' LOA 700 HP Center Console
Chester, MD
New
2026 Key West Boats 263 FS
Price N/A
315' LOA 600 HP Center Console
Chester, MD
New
2026 Key West Boats 239 FS
Price N/A
285' LOA 300 HP Center Console
Chester, MD
New
2026 Key West Boats 239 FS
Price N/A
285' LOA 300 HP Center Console
Chester, MD
New
2026 Key West Boats 239 DFS
Price N/A
285' LOA 300 HP Center Console
Chester, MD
New
2026 Key West Boats 219 FS
Price N/A
261' LOA 200 HP Center Console
Chester, MD
New
2026 Everglades 375CC
Price N/A
481' LOA 1050 HP Center Console
Chester, MD
New
2026 Everglades 315cc
Price N/A
378' LOA 800 HP Center Console
Chester, MD
Boat Prices in Chester, MD
Starting From
$56,900
Average Price
$214,405
Up To
$799,900
Boat Types in Chester
Boat Dealers in Chester, MD
Boats in Chester, Maryland — FAQ
How many boats are for sale in Chester, MD?
There are currently 27 boats for sale in Chester, Maryland from 1 local dealer. Inventory is updated daily with new listings from trusted dealers. Prices range from $56,900 to $799,900, with an average of $214,405.
What types of boats are available in Chester?
Dealers in Chester currently have center consoles, bowriders available. The most popular types are Center Console (20 listings) and Bowrider (3 listings). Browse all listings to find the right boat for your needs.
Do I need a boating license in Maryland?
Maryland requires all boaters to have a Boating Safety Certificate to operate a motorized vessel. This applies to all ages. The Maryland DNR offers approved courses online and in person. A temporary certificate is available for visitors from other states.
Where are the best boating spots in Maryland?
The Chesapeake Bay is Maryland's crown jewel for boating, offering world-class sailing, crabbing, and fishing. Annapolis is the sailing capital of the US. Deep Creek Lake in western Maryland is popular for freshwater boating. The Eastern Shore creeks and rivers are perfect for exploring.
How much does boat registration cost in Maryland?
Maryland charges an excise tax of 5% on boat purchases (with a $15,000 cap on the tax) instead of sales tax. Annual registration fees are based on length and range from $10 for boats under 16 feet to $100+ for larger vessels. Titles are required for all boats.
Boat Buying Guides
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Boat Insurance Cost Estimator
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Try it free →How to Inspect a Used Boat
Step-by-step inspection checklist covering hull, engine, electrical, and trailer before you buy.
Read guide →Used vs New Boats: Cost Comparison
Compare the true cost of buying used vs new: depreciation, insurance, maintenance, and financing rates.
Read guide →Best Time to Buy a Boat
When to buy a boat to save 10-20%: seasonal pricing trends, boat show deals, and end-of-year clearance.
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