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Set Your Course for Summer Fun – Two Big Rendezvous Events in Virginia and Annapolis!!

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used pre owned boats for sale southern bay annapolis

74 Listings

2016 Layton Bay 22

  • Condition: Used
  • Length: 22.17'
  • Hours: 1534 hrs

DESCRIPTION

 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
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1985 Pearson 530

  • Condition: Used
  • Length: 53.58'
  • Hours: 4370 hrs

DESCRIPTION

"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
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1991 J Boats J/40

  • Condition: Used
  • Length: 40'
  • Hours: 1300 hrs

DESCRIPTION

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.

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2019 Grady-White Freedom 255

  • Condition: Used
  • Length: 24.75'
  • Hours: 284 hrs

DESCRIPTION

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.

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1999 Gemini 105M

  • Condition: Used
  • Length: 34'
  • Hours: 1495 hrs

DESCRIPTION

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.

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2023 J Boats J/99

  • Condition: Used
  • Length: 32.5'
  • Hours: 59 hrs

DESCRIPTION

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.

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1996 Tiara Yachts 4300 Open

  • Condition: Used
  • Length: 43'
  • Hours: 2 hrs

DESCRIPTION

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 
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2019 Tiara Yachts C39 Coupe

  • Condition: Used
  • Length: 40.83'
  • Hours: 465 hrs

DESCRIPTION

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.

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2005 Catalina 320

  • Condition: Used
  • Length: 32.5'
  • Hours: 700 hrs

DESCRIPTION

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.

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2006 MJM 34z Express HT

  • Condition: Used
  • Length: 34'
  • Hours: 1562 hrs

DESCRIPTION

ZEST is a well maintained Express HT version of the innovative MJM 34z. Her downeast blue Awlgrip hull is stunning and looks especially nice with the express hardtop. The Express HT is a sleeker profile than the standard downeast version, and offers additional protection for wind and waves.  Northern Lights Genset, air conditioning (on deck and down below), Bow and Stern Thrusters,  teak deck in the cockpit, electrically opening windshield windows (for great breeze when running) , Cold Plate Refrigeration, and all the right gear. Zest is a great offering and is seriously for sale. All reasonable offers will be considered.  

 Yanmar 6LY3M-ETP engine 480 horsepower -  1562 hours, regularly serviced  Straight Shaft Inboard

Northern Lights M673D3 Generator - 447 hours

Sidepower Bow and Stern Thrusters - all the maneuverability of pods/stern drives/outboards with a much less complex and more reliable drivetrain

Marine Air HVAC - two units

Electrically operated Opening Front Windshields

Guest Spotlight

Muir Windlass

Fusion Stereo

Large Refrigerator/Freezer in Galley

Samsung TV

Garmin 12 inch MFD/Chartplotter 8212

Garmin HD Radar and Radardome

Garmin AIS600

Garmin GHP Reactor and GHC20 Autopilot

Standard Horizon Explorer VHF with Remote Mic at Helm

Rear Bimini top

Sea Frost Model BD Cold Plate refrigeration in Ice box 

She is easy to see, located in the water just outside of Annapolis, MD

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2018 Jeanneau Sun Odyssey 419

  • Condition: Used
  • Length: 41.83'
  • Hours: 787 hrs

DESCRIPTION

Celtic Rose is a gorgeous example of the Jeanneau Sun Odyssey 419. Her meticulous ownership to date shows off her exellent condition, the investsments in equipment provide unparalleled capability, the desireable two cabin/two head layout is ideal for extended cruising, while her elegantly drawn Philippe Briand hull makes her a fun day sailor as well. This boat has it all!


With sail controls lead to the helm, short handed sailing the Jeanneau 419 is easy, while guests will enjoy a comfortable cockpit experience free of line clutter. The generous swim platform, spacious cockpit seating, and wide side decks further enhance the enjoyment of being aboard!


Down below, the two cabin two head layout boasts a luxurious owners stateroom with an en-suite head, while the VIP stateroom aft has an offset bulkhead which enlarges the sleeping berth. The main salon offers plentiful natural light, which enhances the beauty of the leather appointments and teak wood paneling throughout the interior. A c-shaped dinette served from a dedicated galley space ensures that all meals at sea are cozy and comfortable, while the large sofa on the port side allows for another sea berth or lounge area. 


A large storage locker aft on the port side with both interior and on deck access ensures plenty of space for all your gear.


The pride of ownership is obvious throughout the boat- significant investments have been made along side the rigorous maintenance schdule. 


The long list of investments, specifications, and upgrades includes:

  • 2025 Bottom Paint
  • 2021 Rainmain MK2 Reverse Osmosis Watermaker
  • Ocean Safety 4 Person Liferaft
  • Renogy 2000 Pure Sine Inverter
  • 4x 100a AGM house batteries
  • Bow Thruster
  • Reverse Cycle Heat and Air Conditioning
  • Smart Plug Shore Power System
  • Raymarine Electronics
    • 2x i70 Displays
    • i70 Autopilot
    • Axiom Pro 16" on Cockpit Table Pod
    • Autopilot Remote Control
    • Raymarine VHF with RAM
  • Fusion RA70n Stereo
  • Electric Cabintop Winch
  • In Mast Mainsail Furling
  • Performance Genoa
  • Asymmetric Spinnaker with lines and blocks
  • Electric heads
  • Rocna 25 KG Anchor
  • Electric Windlass
  • Takacat T340LX Inflatable dinghy
  • 2021 Tohatsu 15HP Outboard
  • 2021 Torqueedo Travel 603 Electric Outboard
  • Folding Three Blade Propellor
  • Streaming TV

The list of upgrades goes on and on, this one has to be seen to be believed! Call the listing broker today for your private tour of this fine yacht.

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2019 Azimut Atlantis 51

  • Condition: Used
  • Length: 53.08'
  • Hours: 353 hrs

DESCRIPTION

If you are looking for a Sports Cruiser with a great layout, generous cabins and has been well maintained, you are in luck. The Azimut 51 Atlantis "Amici" offers all of this and all under $1million.  "Amici" has lived in the Brackish waters of the upper Chesapeake Bay. Pride of ownership beams throughout the boat. Don't miss the opportunity to own this Italian Classic.

  • Seakeeper
  • Generator
  • FLIR Camera
  • Hydraulic Swim Platform
  • Beautiful "Miami Silver" hull paint
  • Captain Maintained

Manufacturer's Description:

Sporty, high-performing and dynamic, to experience the sea in a truly unique way. Atlantis is a versatile sports cruiser for those who love chasing the waves and seeking the true trill of life at sea. Great cruising ease, the ideal balance between quality and safety, the perfect alchemy of beauty and functionality: and all in large, welcoming spaces and meticulously planned interiors in line the best Italian design.

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2016 Layton Bay 22

  • $47,500
  • Used
  • 22.17'
  • 1534 hrs

1985 Pearson 530

  • $199,900
  • Used
  • 53.58'
  • 4370 hrs

1991 J Boats J/40

  • $58,000
  • Used
  • 40'
  • 1300 hrs

2019 Grady-White Freedom 255

  • $110,000
  • Used
  • 24.75'
  • 284 hrs

1999 Gemini 105M

  • $61,000
  • Used
  • 34'
  • 1495 hrs

2023 J Boats J/99

  • $239,000
  • Used
  • 32.5'
  • 59 hrs

1996 Tiara Yachts 4300 Open

  • $164,000
  • Used
  • 43'
  • 2 hrs

2019 Tiara Yachts C39 Coupe

  • $575,000
  • Used
  • 40.83'
  • 465 hrs

2005 Catalina 320

  • $75,000
  • Used
  • 32.5'
  • 700 hrs

2006 MJM 34z Express HT

  • $315,000
  • Used
  • 34'
  • 1562 hrs

2018 Jeanneau Sun Odyssey 419

  • $265,000
  • Used
  • 41.83'
  • 787 hrs

2019 Azimut Atlantis 51

  • $975,000
  • Used
  • 53.08'
  • 353 hrs