boats for sale southern bay annapolis

 The Layton Bay 22 is a custom built center console by Layton Custom Boatworks Edenton NC, This infused construction makes for a safe, smooth and dry ride.

The Layton Bay 22 is a perfect center console for fishing the Bay. The lack of a T-top is great for light tackle and top water fishing. These boats do not come up very often, so don't miss this rare opportunity to get one of the coolest center consoles out there. Call the listing broker today to schedule an appointment to check it out.

• Garmin 8612 MFD
• Transducer
• ICOM IC-M324 VHF
• Fusion MS-RA70NSX
• 2 - 8" Speakers
• ROKK Cell Phone Charger
• Leaning Post and Center Console Covers
• Aluminum double axel trailer with surge breaks, trailer box, spare tire and guide poles
• Livewell to port
• Macerated in-floor fish box
• Raw Water Washdown

"Dalmation" is a rare opportunity for an excellent blue water cruiser as the only Pearson 530 built with a sloop/cutter rig. Several upgrades have been made along with meticulous maintenance by a professional service yard. The boat is very clean inside and out, very bright with natural light.  Electronics have been upgraded and many features added for extended time on the hook with large solar panels, wind generator and a recently replaced Northern Lights generator time away from the dock is made easy. With no open items to be addressed before sailing this boat is ready to cruise at very short notice.  Call to arrange a private showing today! 

• New Northern Lights Generator (2021)
• Furuno Electronics Upgrade
• Solar Panels
• Air Conditioning w/ Reverse Cycle Heat
• Full Cockpit Enclosure

COME EXPERIENCE CAYMAS! AVAILABLE FOR SEA TRIAL AND DEMO USE. GIVE US A CALL TO SET UP YOUR SEA TRIAL NOW!

Demos are available at our Gloucester Point, Virginia office at York River Yacht Haven as well as our Annapolis, Maryland office in Bert Jabin Yacht Yard.

Meet the 291, the latest addition to the highly acclaimed Hybrid Series from Caymas Boats. This stunning offshore hybrid model is designed for those who demand both performance and versatility, making it the largest and most robust member of the family.

Unmatched Performance for the Serious Angler

Crafted with the hardcore angler in mind, the 291 delivers exceptional stability and handling in offshore conditions. Its innovative design features an open bow and higher freeboard, ensuring you can navigate the toughest waters with confidence. Experience the thrill of the catch without compromising on comfort or safety.

Versatility for Family Adventures

While the 291 excels in performance, it also embraces the needs of the entire family. With spacious seating and thoughtful amenities, it’s perfect for everything from an afternoon of fishing to an elegant evening dinner cruise. Enjoy a day at the sandbar with loved ones, knowing that the 291 has you covered.

Key Features

• Open Bow Design: Maximize space and accessibility for anglers and families alike.
• Higher Freeboard: Enhanced safety and stability for offshore adventures.
• Family-Friendly Amenities: Thoughtfully designed features for comfortable cruising and relaxation.
• Superior Craftsmanship: Built with high-quality materials for durability and performance.
• Hybrid Versatility: A true blend of fishing and leisure, perfect for all your boating needs.

Join the Caymas Community

With the launch of the 291, you’re not just investing in a boat; you’re joining a community of passionate boaters who value quality and performance. Share your experiences, connect with fellow enthusiasts, and embark on unforgettable adventures.

Step aboard the S 248 and have your expectations shattered with feature-packed amenities and luxurious fit and finish. With abundant storage throughout, in-floor fish boxes and a spacious aft cockpit, your pros list for buying the Pursuit S 248 just got a lot longer.

With a single Yamaha® 350 HP engine, this 25' 8" entry-level Pursuit is the definition of class-leading. Designed to cater to anglers, the in-floor fishboxes, ample storage bays and spacious aft cockpit are sure to impress. The generous over-sized fiberglass hardtop with full windshield over the center console will protect from the weather when you are running and the sun when you are anchored. Even details like our patented folding aft seat and easy-pull slide out for your cooler demonstrate that nothing was left to chance.

• Pursuit® Protection Plan:
  5 Year Hull and Deck Structural Warranty
  5 Year Blister Free Warranty
  2 Year Limited Warrant
• Pursuit Fresh White Gelcoat
• Hand Laminated Hull with Vinyl Ester Resin and Engineered Fabrics
• Infused Fiberglass Structural Grid System with Molded Finish and Integrated Bilge Water Management System
• Foam Filled Structural Grid
• 3 Ply Resin Infused Composite Transom System
• Integrated Transom Platform Extensions Outboard of Engine
• Boarding Ladder, 3 Step Telescopic, Mounted in Hull Platform
• Trim Tabs, Lenco Electric with Auto-Retract
• Rope Locker, Self-Draining
• Anchor Scuff Plate
• Horn, Electric with Oval Stainless Steel Cover
• Bow Eye, 1/2" 316L Stainless Steel
• Stern Eyes (2), 1/2" 316L Stainless Steel
• Bronze Thru Hull Fittings Below Water Line
• Chrome over Bronze Thru Hull Fittings Below 7 Degree Heel Line
• Stainless Clad Composite Thru Hull Fittings Above the 7 Degree Heel Line
• Bronze Garboard Drain
• Dedicated Transducer Location

Nicely Upgraded J/40  - Outfitted for Extended cruising

Experienced J/boat couple upgraded the boat and then spent 8 months cruising the Caribbean.   They are moving back to land and are  offering the boat up for sale

5' 8"  Shoal Draft version (UFO/wing keel) for easy cruising on the Chesapeake bay and the Bahamas. 

58' air draft to safely navigate the ICW 

Hull professionally painted with Awlgrip Sky Blue (2 primer/2 finish) in 2024.

Bottom sanded, finished 3 coats CSC Interlux bottom paint 2024, single coat in 5/2025

Comprehensive Lithium Ion Phosphate house battery upgrade

-(2) 200 watt Renogy Lithium House batteries(400 ampH), new 2024

-(2) 100 watt Renogy AMG starter/ windlass batteries, new 2024

-(2) 200 watt Bougie flexible solar panels mounted on SS bimini frame over helm station, 100 watt Bougie flexible solar on cabin top, all new 2024

-Victron Smart Solor Controller 100/50 to house lithium batteries, new 2024

-Victron DC to DC Charger, new 2024

-Renogy 2000 watt Inverter, new 2024

-Bulbs or light futures changed to LED’s.

Dometic CFX3 top loading fridge, 12volt, 55 liter 

Garmin Chartplotter 943sxv, touchscreen, shows AIS, new in 2024

Garmin 215 AIS Radio, connected via nmea -2000 to chartplotter, new in 2025

Raymarine p70 autopilot head, to hydraulic ram below deck

Raymarine I60 depth,

All Halyards and most running rigging replaced 1 year ago

2002 Yanmar 4JH3E 4 Cylinder 50Hp - 1300 hours -

Cutlass bearing & 3 bladed bronze propeller, new 2024

New impeller, oil & fuel filters, starter replaced, new 2024

Standing Rigging replaced 2017

 North Laminate roller furling Genoa 2017

Pro furl replaced in 2016 

Dacron Main in 2016

Asymmetrical spin in sock

Hull and deck surveyed 1 year ago.   all moisture Issues addressed

Rocna 20 Anchor w/ swivel, 20 feet of 5/16 anchor chain & 200’ of Maxwell 5/8, 8 strand anchor line, new 2024

Maxwell RC 10-8 windlass, including fuse system, & up/down deck controls, all new 2024

Stainless anchor roller for Rocna, new 2024

Propane remote shut-off valve, regulator & fiberglass propane tank installed 2024.

compostable toilet - can switch to a normal head/holding tank without much effort

Dinghy davits (Dinghy not included) 

Mainsheet upgraded to 4:1 purchase.

Runs 100% on solar  - currently no shorepower hookup, but easy install.

Manual galley sink that could be converted to electric water pressure pump

Small bimini over companion-way.   Solar cells act as a bimini over steering station.

Floors and companionway and could be re-varnished easily to make the boat really shine. 

Very clean - -It's definitely worth a look.   a lot of value here

Easy to see in Bert Jabin's yacht Yard.

As is the J/Boats standard, this J/40 is a true sailor’s sailboat, sails to 6.5 to 7.5 knots, even under head sail alone, travels under motor well @ 6.75 to 7.25 knots, takes offshore seas well and feels solid with 18,000 weight, balancing speed & comfort. Have seen 200kn miles motor-sailing up the coast with crew of two (St Augustine to Beaufort NC in 52 hours, 440kn miles). Boat layout is uncluttered functional deck, large wheel, oversized winches & comfortable seating for crew. Easy to sail or cruise with just two folks (or one). Boat is cruiser ready but designed for racing as well.

Electrical – all new in 2024: (Two) 200watt Bougie flexible solar panels mounted on SS bimini frame over helm station plus 100 watt bougie solar on cabin top, to Victron Smart Solor Controller 100/50 that charges (two) 200 watt Renology Lithium House batteries(400 watts lithium total). Lithium also runs the 2000 watt Renalogy inverter for plenty of 120volt power including running Starlink(not included) and Dometic CFX3, 55 liter top loading fridge(included). All bulbs or light futures changed to LED’s. We ran two laptops; running remote business & teaching college courses from boat.

When engine is running the Victron DC to DC 30amp Charger, charges the Two 100amp Renology AMG Starter batteries, then it charges the 400amp of lithium house batteries that charge at a higher level. Systems feed into a central distribution panel/fuse box, a Victron Lynx.

House lithium batteries are monitored by Smart Victron 712 battery monitor w/ stint that connects to a phone. AMG Starter batteries have a small 50 watt solar set up, separate solar controller & battery monitor w/ stint. The AMG’s also run the windlass flawlessly. NO 110 plug system is currently set up as it seemed three systems to charge house batteries was not needed. Would not be difficult to reinstall 110 system & air, if that is a priority. But with 4 top hatches, 13 opening portlights, 4 dorade vents and 5 new scirocco fans, boat had excellent cross ventilation & was very comfortable in Florida & Bahamas during our cruise.

Water, system was simplified in 2024: 200 plus feet of old water lines removed, old water heater removed, pressure water removed. Tanks cleaned, lines replaced w/ PEX, foot pump at kitchen and at shower, all water lines feed to central distribution. Both 30 gallon water tanks have fuel gauges. Average water use is only 6 gallons per day for two people including: drinking, cooking & cleaning dishes. With foot pumps -No need for a water-maker if cruising East Coast, Bahamas or Caribbean.

Head system updated in 2024: Removed old head & hoses & replaced with an OGE 12 volt compost toilet. Simple system, no smell, lightweight & easy to use. 12 volt fan vent to outside, press button to spin. Once every 5-7 days(two folks) empty the compost (no smell) into a small trash bag & toss into trash. Uses Coco core which is easy to find and is basically ground coconut husk. Would be easy to reinstall conventional marine head, as black water tank is still installed.

The Grady-White Freedom 255 DC is intended to be a versatile, Trailerable boat that can operate in the kind of choppy conditions one often finds in bigger bodies of water such as Pamlico Sound, the Chesapeake, Tampa Bay, Long Island Sound, and even in the ocean on the right kind of day......The major feature of the Freedom 255 is its SeaV2 hull designed by C. Raymond Hunt and Associates and its distinctive sheer line. This is a styling and design characteristic that Grady-White has had for years and it has always set them apart from most everything else on the water in its class.

7/21/2025 - Price reduction to $61K.   Owner wants it sold.

Cruising comfort on the water is what this Gemini Cat is all about. Everything is plain and simple. From the roller furling jib in the bow to the inboard Westerbeke with outdrive (1495 hours)  and dinghy davits aft, it's all there for you to use and enjoy. Comfortable living/dining space, galley, sleeping accommodations (3 separate double beds), and the single head with pull-out shower.  Go into shallow waters other sailboats can't. She's in decent shape due to responsible owners who know how to take care of their boat

Raytheon Autopilot

Raytheon Windspeed, direction, depth

JRC Radar

Uniden VHF

The centerboards were replaced with asymmetric centerboards found on the newer MC model from Chesapeake Light craft in 2018.    The new board shape improves windward performance by generating lift.  They are coated in a barrier coat and 5 coats of bottom paint.  They are new construction

The boat is easy to see just outside of Annapolis, MD.

COME EXPERIENCE CAYMAS! AVAILABLE FOR SEA TRIAL AND DEMO USE. GIVE US A CALL TO SET UP YOUR SEA TRIAL NOW!

Demos are available at our Gloucester Point, Virginia office at York River Yacht Haven as well as our Annapolis, Maryland office in Bert Jabin Yacht Yard.

The Caymas 26 HB does it all for the serious fisherman and for family fun. Performance starts with a Michael Peters patented Stepped-Vee Ventilated Tunnel Hull. This hull delivers speed, fuel efficiency and a precise, dry and velvet-smooth ride with a 9-foot beam. Serious fishing starts with Oversized 35 gallon livewells, maximum storage tackle, large bow/stern fishing decks and a 90-gallon fuel tank to get you to the farthest fishing grounds and back.

The Caymas 26 HB is designed for family fun and a day’s comfort with cushioned bow and stern seating, bow and stern cooler options, up to 8 speaker stereo, extra elbow room beam and a standard Porta Potti in the console when nature or a change of clothes is called for. See for yourself how the Caymas 26 HB enjoys the best in marine fit and finish utilizing the highest quality marine hardware and craftsmanship. The Caymas 26 HB can be rigged with a Yamaha, Mercury, or Suzuki outboard up to 400 horsepower. Our stock boat comes equipped with a 300 HP Mercury V8. The boat will provide great memories and a phenomenal ride.

The J/99 does it all - combining great sailing performance and stability with belowdecks comfort in a boat that can be sailed by just one or two people. The deck layout and sailplan are optimized for easy handling, while the roomy cockpit accommodates 8+ for fun daysailing. Want to jump into the next adventure-style overnight race or cruise rally and can’t find crew?  No problem. The J/99 will reward you with easy, high speed sailing whether solo, twin, or with the whole gang.

This extremely clean, well equipped, and meticulously maintained 2023 J/99 shows like a new boat. With barely any use on the boat, the owner has made other plans, and the 99 unfortunately has to go. 

 Her extensive list of equipment includes:

• North 3Di Main and Jib
• North A2 Spinnaker
• Jefa Direct Drive Auto Pilot
• 12v DC Refrigeration 
• Harken Roller Furling
• 110 Shore Power Cristec Charger
• B&G Triton Instrumentation
• 3 B&G 20/20 Mast Mounted Displays
• B&G Vulcan 9 Display in Cockpit and Nav Station
• B&G Autopilot Controller w/ Keyfob Remote
• Bottom Faired for Club Racing, with Anti Fouling

The J/99 has a versatile cockpit for both cruising and racing. The deck layout has several optimized features including a floating jib lead system, inhauler system, cockpit-led outhaul, cunningham, and double-ended boomvang. The 48:1 cascading backstay system leads to both sides of the cockpit. The two self-tailing primary winches are located within reach of the driver.  

The J/99 interior is roomy with clean lines and uncluttered spaces. The main cabin features two full length settee berths. The L-shaped galley has everything for the weekend cruise including a stove, a 12 volt refridgerator, and an onboard sink with a pressure water system. There’s a proper sit-down, forward-facing, nav station to starboard. The drop-leaf main cabin table is a nice extra, as well.  There are matching double aft cabins with privacy doors. The forepeak is dedicated for the head and sail storage, and otherwise kept as light as possible. 

J/99 Recognition and AwardsThe J/99's performance and capabilities have been widely recognized by the world's yachting press as a truly fun, fast, evolutionary boat from the J/Design and J/Composites build teams. Recent awards include the SAIL's Best Boats- Performance Award, SAILING WORLD's Boat of the Year- Best Crossover Boat, and the British Yachting Awards - Performance Yacht award.

All Reasonable Offers and Trades Considered! 

This Tiara 4300 Open is ready for cruising with comfortable accommodations and a recent mechanical overhaul.  An excellent platform for fishing and extensive cruising with a large cockpit, live-well and fish-boxes.  The bridge-deck offers ample seating for guests when underway with the protection of a full enclosure.  Below decks features a large galley, spacious salon and a master stateroom forward with a queen island bed.  Call to arrange a private showing today! 

The Tiara 4300 Open offers the luxury of space and comfort for whatever water adventure boaters want to pursue. With a lower cockpit area of 84 square feet, and an additional 83 square feet on the step-up command deck, the 4300 Open has the largest social area in its size class. The spacious interior is an awesome living environment, highlighted by an open floor plan and head room that starts at 6 feet, 10 inches and is never less than 6 feet, 2 inches. The 4300 Open is a powerful, smooth and dry-riding yacht with a 15-foot, 2-inch beam.

• Detroit Diesel 6V92 Engines (Rebuilt in 2022)
• New Kohler Generator (118 hours)
• LED Lighting
• Garmin Chartplotter w/ AIS
• Lewmar Bow Thruster 

Price Reduced $10,000.00 July 2025

The 39 Coupe has proven to be a very popular boat for Tiara. Some of the reasons include an amenities list usually only found on bigger boats. And once you try the Volvo IPS Joystick you will never want to go back to boating without it.

• Onan 7.5 kW Genset
• Reverse Cycle Heat and Air Conditioning
• Makefast Marine Powered Sunshade
• Manual Jetski/Dinghy Launch and Storage

Please call the listing broker for more information or to schedule a showing.

Continuing the success and enthusiasm of the Tiara Coupe series is the 39 Coupe. Classic Tiara styling and quality components highlight the exterior; modern interiors and architectural appointments await inside. With open and spacious floor plans that keep galley and cockpit engaged, every detail has been thoughtfully attended to. Ultraleather upholstery compliments the comfortable seating perfect for entertaining or dining. The airy atrium opens to the lower level and provides easy access to the utility room and VIP head.

Tiara’s uncompromised quality and luxury combined with the latest in navigation and operating technologies make the Tiara 39 coupe a perfectly sized and powerful package. Twin Volvo Penta IPS drives, paired with the dependable, sweet-riding Tiara hull, deliver an exceptional driving experience. The ergonomic helm with seating for two compliments the joystick controls and glass cockpit instrumentation with two displays that provide easy navigation and increase the enjoyment of your yachting experience. Settle in to a comfortable cruise at 30 mph, or turn it up and enjoy that last dash into the inlet at a get to your destination faster at a wot speed of 40 mph.

Catalina 320 "Windshadow" is an excellent cruising boat well cared for and well equipped for sailing the Chesapeake.  Sailed in fresh water through 2021 before moving to the current location on the York River.  An excellent sail inventory includes many recent sails with light use.  The large cockpit offers a great social space while below decks provide comfortable accommodations for extended cruises.  All maintenance is up to date, ready for a new owner.  Call today to arrange a private showing! 

• Raymarine Electronics
• Air Conditioning w/ reverse Cycle Heat 
• Yanmar 27hp Engine (700 hours) 
• North Sails Main (2020)
• North Sails 135 Genoa
• North Sails 155 Genoa (2018)
• 2 x Genneker w/ Sock

Manufacturer Description:

The Catalina 320 is an exciting design that successfully combines the best modern features and construction with Catalina's hallmark comfort and value. Based on a high-performance and high-volume computer-optimized hull design, the 320 is light on the helm and tracks well under sail or power. Motion and heeling are gentle and predictable. The 320 performs well in a variety of conditions, with either the available wing or fin keels. Racing skippers will enjoy the turn of speed and cruisers will appreciate the additional distance covered in a day's passage. Carrying the deck beam well aft created space for an exceptionally large cockpit. The wide coamings and ergonomically correct seats and backs are important features, considering the cockpit is where we all spend the most time when aboard. The weather decks are wide with molded-in non-skid and bulwarks, giving easy, sure access to the foredeck and standard below deck electric anchor windlass. Other important quality features of the deck include the stout aluminum framed opening deck hatches and ball bearing mainsheet traveler system. The rigging and spar systems are engineered for performance and durability. The fore and aft lowers with intermediate and upper shrouds make the rig very secure and easy to keep in tune. A rigid adjustable boom vang is standard. The unique interior is beautifully finished in a rich combination of teak, ash and maple hardwoods, complementing the beige textured fiberglass overhead and full hull liner. Attention to details like the custom molded galley counters with integral backsplashes, three separate lighting circuits in the main cabin, removable panels in the forward bulkhead, and a cedar paneled hanging locker set the 320 apart from the ordinary. The one-piece, integral molded fiberglass subsole grid system is rigid, strong and requires no maintenance.