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Long Boat Key

One of the most popular communities provided by Michael Graf

Long Boat Key

About Long Boat Key

Longboat Key, Florida, is a tranquil paradise that offers the perfect blend of luxurious living and natural beauty. Nestled between the sparkling waters of the Gulf of Mexico and Sarasota Bay, residents enjoy stunning beaches, picturesque sunsets, and a laid-back, island lifestyle. The community is renowned for its upscale amenities, including gourmet dining, boutique shopping, and world-class golf courses, all while maintaining a quaint, small-town charm. With year-round warm weather, ample outdoor recreational activities, and a strong sense of community, Longboat Key is an ideal place for both relaxation and adventure, making it a highly desirable destination for those seeking a serene coastal retreat.

One of the most popular communities provided by Michael Graf

494

# of Listings

2

Avg # of Bedrooms

$947

Avg. $ / Sq.Ft.

$1,695,622

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

494 Properties Found. Page 22 of 33.

Wonderful opportunity is now yours! Welcome to 603 Cedars Ct, a lovely and very well kept townhome in the vibrant fitness and tennis community of Cedars East, ideally located between Sarasota Bay and the Gulf of Mexico on picturesque Longboat Key - just a short stroll to the island's sugary white sand beaches, and tranquil turquoise waters.
This turnkey furnished, three-level townhouse offers a spacious open floor plan with 2 bedrooms, 2 baths, and an oversized attached 2 car tandem garage. Thoughtfully maintained by its current owners, it features a new roof (2022) and newer HVAC (11/2022). With a 14-day minimum rental policy and on-site management, this property is perfect for generating rental income or enjoying as a full-time or seasonal residence. Excellent rental production ready to share with future bookings available to convey upon purchase.
Inside, you'll find a bright, open great room with balcony views of lush, tropical greenery, a well-equipped kitchen with stainless steel appliances, granite counters, wood cabinetry, and a glass tile backsplash.? Along with a convenient laundry closet featuring a stackable washer/dryer.
Upstairs, the large primary suite includes double closets, wood flooring, wooded views and a bath with dual sinks. A second bedroom and full bath are nearby, and ideal for guestes.
Additional highlights: tile and wood floors throughout (no carpet), ceiling fans, high ceilings, turn-Key furnished, neutral décor, garage storage, and a private balcony storage closet. Windows are double pane, hi-Impact and in good condition. Oversized garage with a large storage closet, perfect for all the hobbies and is a very rare asset on Longboat Key. Cedars East is a 66-acre village-like townhome setting, surrounded by nature & close access to both the beach and bay on the beautiful north end of Longboat Key. Spacious and tropical community w/ lit boardwalks leading through mangroves to amenities including heated Jr. Olympic Size Pool, 9 Har-Tru Tennis Courts, 3 Har-Tru Pickle Ball Courts, Club House w/ Pro-Shop, 24hr Fitness Center, Tiki bar, Restaurant, Fishing Pier & kayak launch. Some amenities require additional membership to the club for use. Walking distance to area attractions like Harry's Deli and Continental Kitchen, a true island gem in Joan Durante Park, Lo-Key Girll, and, of course, Longboat Key's world-famous sugary white sand beaches. Close to other main attractions and cultural events, e.g., St. Armand's Circle - famous for world-class shopping and dining, Mote Aquarium with marine exhibits and marine/kayaking excursions, the Asolo Repertory Theatre, Van Wezel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, Ringling Museum complex and numerous dining options on Longboat and in downtown Sarasota. If you are a golfer, there are a number of top-rated courses nearby. Spacious Condo Ownership, property w/ Townhome Design, perfect for year-round Island living? or perfect for seasonal and/or vacation rental or Can Ideally provide the perfect combination of both. Cedars is also a pet-friendly community!! Priced to Sell, Come see - today!!

LONGBOAT KEY

603 CEDARS COURT

2 Beds

2 Baths

2,268 Sq.Ft.

$525,000

MLS#: A4652969

#A4639404

LONGBOAT KEY

4400 EXETER DRIVE J-201

2 Beds

2 Baths

1,376 Sq.Ft.

$525,000

MLS#: A4639404

LOCATION! LOCATION! LOCATION! Looking for a Beach/Bay Getaway Villa? This cozy End Unit Beach/Bay 2-bedroom/2-bath Sunny Villa boasts 1084 square feet of Longboat Key Florida Fun! Single story living with a convenient covered carport only a few steps away from your front door. Villa 15 is located directly across the street from the tranquil Gulf with its crystal-clear turquoise blue waters and uncrowded soft sandy beaches that attract visitors from all over the world. (Take joy with 3 beach access points, one private deeded) Enjoy walks along the shore, kayaking on the bay or read a book, unwind and soak up the sun on your own private patio while taking in the beauty of this incredible location. The patio is an ideal spot for morning coffee, watching a game of shuffleboard, hosting friends for sunset libations, evening grilling, or simply relaxing in solitude. Your beach/bay lifestyle possibilities are endless. Worry free living with recent Hurricane Impact Windows/Sliding Doors, Roof, & Carport (2020). As an added bonus with the sale of this Villa, the longtime owner since 1976, former Canadian Navy-Man, and a wonderful Nonagenarian, will be leaving most of his nautical treasures gathered from lands around the world for you to enjoy. Set like a jewel on the barrier island of Longboat Key, the community of Windward Bay is a magical wildlife haven nestled mid-island, flourishing on 26 acres and graced with 1/2 a mile of waterfront trails to relish. A low-density residence and a nature lover’s delight to gaze both frolicking dolphins and manatees as they play. Bird enthusiasts jubilate with their front-row seat of the magnificent Florida birds that call Windward Bay their home. Witness the vibrant plumage and graceful flights of these majestic creatures as they effortlessly navigate the glorious skies above. Windward Bay offers numerous amenities that make it an exceptional value including: 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee, barbecue grills throughout, fishing piers, 2 fish cleaning stations, kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits throughout the property. Conveniently accessible to Downtown Sarasota, St. Armands Circle, Anna Maria Island, Historic Cortez Fishing Village, Championship Golf Courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Welcome home to “Pet Friendly” Windward Bay, where TWO pets are allowed. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced. This wonderful villa exemplifies “Florida Gulf to Bay Living” at its finest. Perfect for couples or individuals seeking paradise! Schedule your private tour today and make these experiences a reality.

LONGBOAT KEY

4840 GULF OF MEXICO DRIVE Villa 15

2 Beds

2 Baths

1,084 Sq.Ft.

$524,900

MLS#: A4652683

New on site 2 days ago

#O6326464

LONGBOAT KEY

779 SAINT JUDES DRIVE N

2 Beds

1 Baths

882 Sq.Ft.

$523,000

MLS#: O6326464

#A4631785

LONGBOAT KEY

2045 GULF OF MEXICO DRIVE M1-502

2 Beds

1 Baths

1,019 Sq.Ft.

$515,000

MLS#: A4631785

New on site 1 day ago

Discover coastal living at its finest in this beautifully furnished 2-bedroom, 2-bath condo featuring a recently remodeled kitchen, new carpet, and modern electric shades. This bright and welcoming unit offers comfort and convenience just seconds from your own deeded beach access—perfect for daily walks or sunset strolls.

Enjoy a resort-style lifestyle with incredible amenities including 4 swimming pools, tennis and pickleball courts, a clubhouse, fitness center, library, art studios, billiards, shuffleboard, kayak launch, and a woodshop. The community harbor offers boat slips for rent at just $350–$425 per year—an unbeatable value!

No hurricane water intrusion, and all current assessments have been paid. A rare opportunity for turnkey coastal living in a vibrant, amenity-rich community!

LONGBOAT KEY

4350 CHATHAM DRIVE E106

2 Beds

2 Baths

1,072 Sq.Ft.

$499,999

MLS#: A4657888

This well-appointed, fully furnished, two-bedroom, two-bath Portobello residence is so close with deeded access to Longboat Key's 10-mile beach. This impeccably maintained convenient ground-level home is in pristine condition, and a spaciously designed, coastal-inspired interior creates feelings of tranquility and hospitality. The primary living space enjoys abundant natural light from sliding glass doors opening onto a screened and covered lanai for your relaxation and added dining alfresco. The kitchen has all appliances and granite countertops with passageway to the dining area. The primary bedroom has sliding glass doors to the lanai with en-suite bath and generous walk-in closet, and a guest wing offers every comfort with its sliding glass door to the lanai too. Portobello gives support and comfort to owners with a full-time on-site maintenance crew. You and your family and friends will love the outdoor activities that are near such as LBK Town Center, the beach, miles of pedestrian walkways and more miles of designated bikeways, golf, fishing, Bayfront Park with pickleball, treed dog park and amenities for all ages, staffed USTA award-winning public 10 Har-Tru clay tennis courts and the renowned one-of-a-kind mecca for shopping and dining at St. Armands Circle. L-I-V-I-N the dream on Longboat Key. News Flash! Starbucks to open on LBK late Summer 2025 at midkey 3174 Gulf of Mexico Drive. We are walking distance away, and a $100 gift certificate will be given to Buyer.

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B104

2 Beds

2 Baths

1,432 Sq.Ft.

$499,900

MLS#: A4637105

PENTHOUSE UNIT!! No hurricane flooding or damage to the entire community from both hurricanes!! Only attached to one other unit!! SELLERS HAVE AN ASSUMABLE MORTGAGE AT 3.25 PERCENT AND A LARGE AMOUNT LEFT ON THE MORTGAGE TO ASSUME. Well updated 2 Bed and 2 full bathrooms. All of the floors are ceramic tile that looks like hardwood, and were installed in the last year. The appliances are new and they removed the wall between the kitchen and living room. The quartz counters are new. The unit has a partial view of the canal, and residents can have a boat dock for 495 per year. The community is gated and the unit has one assigned parking spot that is covered. There is a storage unit directly next to the unit. There is a beach access almost directly across the gulf of mexico drive. The swimming pools have beautiful views of the bay. The gym is located in the clubhouse . You are close to St Armand's and close to Anna Maria. The unit is bright and presents really well. If you are a boater or like to fish...this unit would be a great option.

LONGBOAT KEY

4380 EXETER DRIVE 303

2 Beds

2 Baths

1,152 Sq.Ft.

$499,000

MLS#: A4625662

DEEDED BEACH ACCESS - Discover this 3rd floor (with elevator access) 2 bed, 2 bath condominium located in Longboat Arms a well-maintained community on Longboat Key, Florida. Move-in ready with bay views on the veranda. Enjoy entertaining in the unit with open floor plan that has 9' ceilings and a generous sized great room and dining area. The primary bedroom is also oversized with a walk-in closet and en-suite bath provides a peaceful retreat. This condominium has an in-unit washer and dryer, as well as added storage throughout. The AC was replaced in 2023, and flooring replaced in 2021. Residents will enjoy access to the private boat ramp, which is excellent for kayaks, paddle boards, jet skis, and various watercraft. Boat docks are available first come, first served for an annual fee, providing convenient access to the water for boating enthusiasts. Longboat Arms is a community that has great amenities, including an upgraded heated swimming pool, clubhouse, tennis court, community grill area and deeded beach access. The assigned oversized carports that can even accommodate boat storage and ample guest parking.

LONGBOAT KEY

3320 GULF OF MEXICO DRIVE 307C

2 Beds

2 Baths

1,187 Sq.Ft.

$495,000

MLS#: A4652351

This beautiful corner unit is in excellent condition and has not experienced any storm damage, offering peace of mind for potential buyers. Additionally, being a two-story complex, association will not incur unexpected costs from new Milestone inspections providing buyers with one of the lowest quarterly fees on the island. Located just across the street from the turquoise, uncrowded public beaches of Longboat Key. You will enjoy captivating sunsets and partial Gulf of Mexico views in this lovely west facing 2 bedroom, 1 bath, upper level Longboat Key condominium. Conveniently located on the central portion of the key near the community park and tennis courts, Publix, library, CVS and various restaurants and amenities. Impact glass sliders and windows installed 12/2020 and new roof installed 4/2021. Pets and tenants allowed, see community details for restrictions.

LONGBOAT KEY

2850 GULF OF MEXICO DRIVE 2

2 Beds

1 Baths

791 Sq.Ft.

$489,000

MLS#: A4626210

REDUCED PRICE!!! Great investor or seasonal rental property - This charming turnkey short-term vacation rental one bedroom with two queen size beds, one bath and a queen size sofa sleeper, living-dining combo is a beach side end unit. It comfortably accommodates six individuals for an enjoyable stay. Including a screened in porch, plantation shutters, a walk-in storage/closet and kitchen with all the necessities. This unit is a few steps away from the heated pool, two BBQ grills, putting green, shuffleboard, coin laundry facility onsite and a short walk to the beach. There are two gazebos providing shade adding to your relaxation and protection from the sun and rain as you admire the beach scenery from sunset to sunrise. It is a great place for all to enjoy the tranquility of Longboat Key which offers quaint boutiques, fresh seafood restaurants, scenic bike paths creating a blend of relaxation and adventure. Turtle Crawl is ideally situated in a convenient location near Sarasota and St Armand Circle with access to dining, shopping, entertainment, golf courses, marinas and more. This short-term vacation rental presents a fantastic investment opportunity allowing daily, weekly and monthly rentals. There is a management team onsite that handles all bookings, cleaning, management and more. This on-site rental office ensures seamless bookings and assists with all guests needs. You may also use your own management crew of your choice if you prefer. Please Note Flood insurance is covered by the HOA for the unit it does not include personal items. This investment property is successfully rented as a vacation rental during the high season and is currently occupied by excellent annual renters with future bookings through the year 2025. The condo did not suffer any damages from the recent hurricanes or storms. Very rarely do you find a Turtle Crawl unit on the market. Come take a look at this attractive unit and start earning immediate income as you own a slice of paradise on the beach side of Longboat Key.

LONGBOAT KEY

4235 GULF OF MEXICO DRIVE G203

1 Beds

1 Baths

757 Sq.Ft.

$475,000

MLS#: A4646725

72 ft x 26 ft Boat Slip on L-dock at Longboat Key Moorings Marina for sale. Exceptional views of Sarasota Bay and the city skyline from atop your flybridge. LBK Club membership is required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes restaurant, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. All vessels must be approved prior to closing by the Association. Max length of vessel allowed is 67 LOA. Usable beam depends on vessel. Call to discuss the possibilities. A current photo of the vessel must be provided, and the vessel approved by the Association before entering the marina.

LONGBOAT KEY

2600 HARBOURSIDE DRIVE L-04

None Beds

None Baths

N/A

$450,000

MLS#: A4645494

Welcome to your cozy island townhome at the north end of Longboat Key. Perfect as a fulltime residence, seasonal retreat, or investment property, this one-bedroom, two-bath unit fits your needs. This two-story property weathered three hurricanes in 2024, sustaining only minor flooding in the garage during Hurricane Helene and a cracked top-floor window during Hurricane Milton. The HOA will cover and replace the window. On the ground floor, enjoy your private parking garage and storage space. The main living area on the first floor features an open-concept living room and kitchen, ideal for relaxing or entertaining. Step out onto the screened balcony to enjoy the natural beauty of Florida or unwind with your morning coffee. This floor also has a full bathroom and a pull-out sofa for
hosting guests.
The second floor boasts a spacious master bedroom with a king-sized bed and two walk-in closets, filled with natural light from large windows. This level includes a second bathroom and a sun deck with an outdoor shower, offering peaceful views of a natural reserve. It’s the perfect spot to soak up the sun or enjoy a good book in a hammock. Short-term rentals with a 14-day minimum stay are allowed, adding investment potential. From July 2024 - July 2025, the home already has booked rental income booked totaling $45,0000.
With some cosmetic upgrades, this could be even more! The unit is part of a top-notch tennis club that now includes two pickleball courts. You'll be close to the pool and the island’s beaches. Pet-friendly and welcoming, the community features a Junior Olympic-sized pool, a Tiki Bar, and a restaurant for a resort-like feel. Nature trails wind through the property, leading to a dock with stunning views of Sarasota Bay—
perfect for launching your kayak to explore mangrove tunnels or paddle alongside manatees and dolphins.
Whether you're into kayaking, tennis, pickleball, cycling, or jogging in nearby John Durante Community Park, this condo offers the perfect balance of luxury and leisure. Your island paradise is waiting—make it yours today!

LONGBOAT KEY

619 CEDARS COURT

1 Beds

2 Baths

2,376 Sq.Ft.

$450,000

MLS#: A4629084

This chic designer two-bedroom townhome is simply gorgeous throughout. Offered furnished and ready to move into. Each room has received a thoughtful and elegant design, from furnishings to color schemes. The first floor is beautifully tiled with many updates including the kitchen with Quartz counters and backsplash, custom cabinetry, custom sink and faucet, and convenient washing machine. Baths are beautifully updated with designer fixtures. Smart recessed lighting throughout the condominium. Spacious bedrooms have ample closet-storage space and great storage throughout. Ascend to the second floor where you'll find elegant dark engineered wood flooring paired with tile in the bathroom. The enclosed lanai offers an extra room for an office or family space. A/C system includes an iWave-R ionization generator. Also, a spacious private garage with storage. Sutton Place is an amenity packed community. 2 pools, marina, community room, private beach access with bathrooms/showers, kayak storage and electric kayak lift. Come take a look --you'll wish to make it your own! No water intrusions post-hurricanes 2024.

LONGBOAT KEY

527 SUTTON PLACE T-12

2 Beds

1 Baths

1,448 Sq.Ft.

$449,900

MLS#: A4639006

Major reduction again! A super opportunity to be the next owner! Immerse yourself in breathtaking panoramic bay views from this beautifully curated end-unit 2-bedroom coastal retreat. Filled with natural light and embraced by serene harbor waters, this radiant oasis perfectly captures the essence of relaxed seaside living. Enjoy the privilege of private deeded beach access, two sparkling resort-style pools, a friendly clubhouse, and marina—all nestled within a tranquil, pet-friendly community welcoming up to two furry companions. Convenience meets comfort with elevator access, a private storage bin, BBQ grill, and your own dedicated carport parking space. Just across the way, the exclusive Beach Club at 4415 GOM invites you to go barefoot along one of the region’s most pristine sandy beaches. Whether you're savoring your morning coffee with a harbor view, watching the sunrise from the poolside, or toasting to a sunset at your private beach—this is your coastal dream made real at an incredible value. Don't let this seaside sanctuary slip away—your dream lifestyle is waiting!

LONGBOAT KEY

600 SUTTON PLACE B305

2 Beds

2 Baths

1,360 Sq.Ft.

$448,000

MLS#: A4648433

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