Boats for Sale in Chester, MD
32+ new and used boats from dealers in Chester, Maryland. Updated daily.
32 boats available
Used
2004 Regal Commodore 3860
$84,900
481' LOA 840 HP Bowrider
Chester, MD
Used
2010 Composite Yacht 36
$199,900
432' LOA 480 HP Yacht
Chester, MD
Used
2016 Buddy Davis 28 CC
$182,900
336' LOA 500 HP Center Console
Chester, MD
Used
2021 Cobia Boats 280CC
$162,500
331' LOA 500 HP Center Console
Chester, MD
Used
2022 Everglades 273CC
$199,900
327' LOA 600 HP Center Console
Chester, MD
Used
2023 Reef Runner 34CC
$349,900
408' LOA 900 HP Boat
Chester, MD
Used
2023 Everglades 273CC
$219,900
327' LOA 600 HP Center Console
Chester, MD
New
2027 Solara Boats S-310 SB
Price N/A
406' LOA 600 HP Boat
Chester, MD
New
2027 Solara Boats S-250 DC
Price N/A
350' LOA 300 HP Boat
Chester, MD
New
2027 Key West Boats 249FS
Price N/A
297' LOA 300 HP Center Console
Chester, MD
New
2027 Key West Boats 239 FS
Price N/A
285' LOA 300 HP Center Console
Chester, MD
New
2027 Key West Boats 239 DFS
Price N/A
285' LOA 300 HP Center Console
Chester, MD
New
2027 Key West Boats 219 FS
Price N/A
261' LOA 200 HP Center Console
Chester, MD
New
2027 Key West Boats 203 DFS
Price N/A
243' LOA 150 HP Center Console
Chester, MD
New
2027 Key West Boats 1720 CC
Price N/A
206' LOA 70 HP Center Console
Chester, MD
Used
2019 Cobia Boats 344CC
$259,900
412' LOA 900 HP Center Console
Chester, MD
New
2027 Solara Boats S-310 CW
Price N/A
380' LOA 600 HP Boat
Chester, MD
New
2026 Everglades 367CX
Price N/A
447' LOA 850 HP Center Console
Chester, MD
Used
2021 Pursuit Boats DC 365
$484,000
467' LOA 900 HP Center Console
Chester, MD
Used
2021 Sea Lion 34 TE
$239,900
408' LOA 700 HP Boat
Chester, MD
New
2026 Solara Boats S-250 C
Price N/A
374' LOA 300 HP Boat
Chester, MD
Used
2014 Steiger Craft 21 Tournament
$49,900
252' LOA 200 HP Boat
Chester, MD
New
2027 Solara Boats S-250 CW
Price N/A
350' LOA 300 HP Boat
Chester, MD
New
2027 Solara Boats S-310 SC
Price N/A
370' LOA 600 HP Boat
Chester, MD
New
2027 Solara Boats S-250 C
Price N/A
374' LOA 300 HP Boat
Chester, MD
Used
2017 Everglades 355 Center Console
$249,900
424' LOA 900 HP Center Console
Chester, MD
Used
1997 Formula 382 FASTech
$99,999
458' LOA 1000 HP Bowrider
Chester, MD
Used
2023 Everglades 395CC
$749,000
468' LOA 1275 HP Center Console
Chester, MD
New
2026 Steiger Craft 28 Fisherman
$221,700
336' LOA 600 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
$49,900
Average Price
$250,280
Up To
$749,000
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 32 boats for sale in Chester, Maryland from 1 local dealer. Inventory is updated daily with new listings from trusted dealers. Prices range from $49,900 to $749,000, with an average of $250,280.
What types of boats are available in Chester?
Dealers in Chester currently have center consoles, bowriders, yachts available. The most popular types are Center Console (19 listings) and Bowrider (2 listings) and Yacht (1 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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Try it free →How to Inspect a Used Boat
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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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