2018 Catalina 275 SportSold
$59,900
Boat in Annapolis, MD 21403 US
275 Sport
1 Engine (Yanmar)
27.5 feet
Diesel
Fiberglass/Reinforced
The Catalina 275 was the 2014 winner of the both the Cruising World Magazine "Best Pocket Cruiser" & Sailing World Magazine "Best Recreational Racer" - First time a boat had one both awards in 33 years.
Offered for sale by the original owner. Located on Back Creek her whole life and always stored on land for the winters. Locally maintained & serviced.
The Catalina 275 is a nice short handed sailing vessel, that can take you around the race course. Has a real marine toilet with holding tank and manual fresh water system! Easy to clean and maintain.
5' Performance Keel, inboard diesel, furling headsail, & self-tacking jib setup.
"Lensman" has only been lightly used and her original Doyle sail complement includes: Dacron Full Batten Mainsail - Dacron 106% Furling Genoa - Dacron Self-tacking Jib - 1.5oz Asymmetrical Spinnaker w/Code 0 Furler
5K Price reduction 9/5/2025 $59,900
Seller needs her sold now!
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- Private Enclosed Head
- Solid Maple Interior Trim
- Storage Lockers under Berths
- Convertible Main Cabin Table with Pedestal
- Filler Cushion to Convert Salon to Large Berth
- LED Lighting
- Teak and Holly Textured High Pressure Laminate Sole
- Opening Forward Hatch with Light Diffusing Lens and Screen
- Mid-Deck Deadlight with light Diffusing Lens
- ( 4 ) Removable Zippered Gear Bags - Color Coordinated
- Sunbrella Cushion and Berth Covers with Contrasting Piping
- GALLEY
- 12V Plug in Galley
- Storage Cabinet in Galley with Cutlery Drawer
- Polished Stainless Sink with Overboard Drain & Seacock
- Removable Cooler Stores in Drawer with Ball Bearing Guides
- Fresh Water Pump Self Contained Water System
HEAD
- Opening Port with Screen
- Sink and Vanity with Fresh Water Manual Pump and thru Hull Drain & Seacock
- Hooks and Hanging Area
- Marine Head with Holding Tank including Deck Pump Out Plate Wet Locker for Foul Weather Gear
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- Standard Draft Lead Keel - 5’ Draft
- Self Tacking Jib Hardware
- Comfortable Cockpit with Contoured Coamings
- ( 2 ) Large Cockpit Seat Lockers
- Two Mooring Cleats, Fore and Aft
- Molded in Anchor Locker with Rode Securing Point
- Stainless Steel Bow Pulpit
- Stainless Steel Stern Ladder
- Manual Bilge Pump with Thru Deck Handle
- Self Bailing Cockpit
- Storage Pockets for Halyards Lines in Cockpit
- Walk-through Transom w/Swim Ladder
- Carbon Fiber Tiller with Hiking Stick
- Low Friction Rudder Bearings
- Lifelines: Stern Looks and Stern Gates with Pelican Hooks
- Cunningham Adjuster for Mainsail
- Jib Track and Cars Mounted on Cabin Top
- Removable Bow Sprit
- Doyle FB Main with Square Top
- Doyle ST Jib 82% w/Vertical Battens (in Bag)
- Doyle 106% Furling Genoa (on furler)
- Doyle APC Asymmetrical Spinnaker w/Code 0 Furler (Dk Blue & Green)
- ( 2 ) Cabin Top – Winches, Port & Starboard
- Ball Bearing Mainsheet System with 3:1 Gross Purchase, 6:1 Fine Purchase
- ( 4 ) Sheet Stopper
- Halyards Led Aft to Cockpit
- Single Line Mainsail Reefing System Led to the Cockpit
- Rigid Adjustable Boom Vang with 4:1 System
- Mainsheet Traveler located in Cockpit, 4:1 System
- Vectran Line Main Halyard
- Ball Bearing Headsail Furling Gear
- Retractable Bow Sprit and Deck Hardware
- 24:1 Back Stay Adjuster w/Mainsail Flicker at Masthead
- Raymarine i70 Color Display On Port Bulkhead
- Speed / Depth Triducer
- Inclinometer
- Yanmar Digital Engine Control Panel
- Winch Covers (4) (Cadet Grey)
- Tiller Cover (Cadet Grey)
- Beverage Holders in Cockpit
- Fortress Aluminum Anchor w/Chain & Rode (used 1x)
- Misc. USCG Safety Gear
- Horseshoe Buoy w/Bracket
- Assorted Padded Lifeline Covers
The Catalina 275 Sport is a 5 Series’ design from Catalina. It reflects what many sailors have told us – they no longer need that big boat, but don’t want to give up racing or day sailing. They are spending fewer nights aboard, but still want the ability to overnight, even if it’s an occasional trip with kids or grandkids.
The 275 Sport was designed to meet these desires and exceed expectations. We started with a modern, long waterline, and kept the beam modest to allow trailering. The handsome hull is coupled with a powerful rig with large main and self-tacking jib, which makes the 275 not only fast, but also super-easy to sail. The cockpit is what the 275 is all about. The helmsman will become reacquainted with the simple pleasure of steering a well-balanced responsive boat with a tiller from the comfortable, ergonomically designed outboard coamings.
Accommodations below are adequate for weekending or just getting out of the weather, and an enclosed head is always appreciated, even on day sails.
Sail Area
Actual: 380 sq.ft.
100% Foretriangle: 318 sq.ft.
I : 34' 5"
J : 8' 9"
P : 31' 6"
E : 11' 6"
The Company offers the details of this vessel in good faith but cannot guarantee or warrant the accuracy of this information nor warrant the condition of the vessel. A buyer should instruct his agents, or his surveyors, to investigate such details as the buyer desires validated. This vessel is offered subject to prior sale, price change, or withdrawal without notice.
Price History
| Date | Event | Price |
|---|---|---|
| 2/27/26 | Initial price | $59,900 |
2018 Catalina 275 Sport Video Tours
Overview from around the web 2018 Catalina 275 Sport
Customers praise the 2018 Catalina 275 Sport for its exceptional balance of performance, comfort, and style
Many highlight its responsive handling and solid construction, making it an ideal choice for both casual day sailing and more spirited adventures. Owners appreciate the spacious and thoughtfully designed cockpit, which offers plenty of room for friends and family to relax. The interior receives positive remarks for its clever use of space, providing comfortable accommodations without feeling cramped. Additionally, sailors often mention the boat’s ease of handling, making it accessible for both beginners and experienced sailors alike. Overall, the 2018 Catalina 275 Sport is celebrated for delivering a versatile and enjoyable sailing experience.
The Biggest Pros and Cons
The 2018 Catalina 275 Sport offers a compelling blend of performance, comfort, and style, making it a popular choice among sailing enthusiasts. Here are some of the key pros and cons of this model:
Pros
Performance-Oriented Design: The 275 Sport features a sleek hull and a well-balanced sail plan, providing responsive handling and good speed, ideal for both casual cruising and club racing.
Spacious Cockpit: Its roomy cockpit layout offers comfortable seating for family and guests, making it perfect for day sailing and entertaining.
Modern Amenities: The boat comes equipped with updated features such as a comfortable cabin with standing headroom, a functional galley, and a private head compartment.
Easy Handling: With features like a self-tacking jib and in-mast furling options, the Catalina 275 Sport is manageable by a small crew or even single-handed sailors.
Quality Build: Catalina Yachts is known for solid construction and reliable craftsmanship, and the 275 Sport maintains this reputation with durable materials and attention to detail.
Cons
Limited Cabin Space: While comfortable for day trips and short overnight stays, the cabin may feel cramped for extended cruising or larger groups.
Performance Trade-offs: Compared to more racing-oriented boats, the 275 Sport sacrifices some speed potential in favor of comfort and ease of use.
Optional Upgrades: Some desirable features, such as advanced electronics or certain rigging options, may only be available as add-ons, increasing the overall cost.
Weight Considerations: The boat’s build, while sturdy, results in a heavier displacement that can affect light wind performance.
Made For
The 2018 Catalina 275 Sport is designed for sailing enthusiasts seeking a versatile and performance-oriented day sailer. Ideal for those who enjoy both casual cruising and spirited sailing, it appeals to individuals or small groups looking for a manageable, trailerable boat that combines modern design with comfortable accommodations. Whether you're a weekend sailor, a coastal explorer, or someone new to the sport eager to learn and grow, the Catalina 275 Sport offers an excellent balance of ease, speed, and style.
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Meet the Broker

Address
Boat Location
Contact Sail Annapolis, Inc. about 2018 Catalina 275 Sport
303 Second Street, Suite C, Annapolis, MD, 21403
Contact Sail Annapolis, Inc.
303 Second Street, Suite C, Annapolis, MD, 21403

















































