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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

417

# of Listings

2

Avg # of Bedrooms

$828

Avg. $ / Sq.Ft.

$1,409,238

Med. List Price

Browse Long Boat Key Real Estate Listings

$250,000 - $500,000

42 Properties Found. Page 1 of 3.

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

Gulf Views | Move-In Ready | Gated Community
Welcome to Seaplace, one of Longboat Key’s most desirable Gulf-front communities! This charming 2-bedroom, 1-bath residence is located on the 3rd floor of Building G5 (Unit 304) and offers sweeping southwest-facing views of the Gulf of Mexico from your private, screened-in lanai.
Enjoy morning coffee or evening sunsets while soaking in the turquoise waters just beyond your doorstep. Inside, the open-concept layout connects the living and dining areas with a bright, functional kitchen—perfect for relaxing or entertaining.
Whether you’re searching for a vacation getaway, income-producing investment, or full-time coastal retreat, this condo checks every box.
Seaplace is more than a community—it’s a resort-style experience, offering:
• Gated entry with 24-hour guard service
• Two sparkling swimming pools and two hot tubs
• A shallow kiddie pool for the little ones
• Three tennis courts
• A beautifully updated clubhouse for social gatherings
• Walking trails through lush tropical grounds
• Beach chairs & umbrellas provided for residents
Best of all—you’re just steps away from the sand. With unbeatable Gulf views, modern comforts, and a strong community feel, this property offers the best of Longboat Key living.
Don’t just dream about the beach—live it. Schedule your private showing today and discover why Seaplace is one of Longboat Key’s most beloved communities.

LONGBOAT KEY

1965 GULF OF MEXICO DRIVE G5-304

2 Beds

1 Baths

1,023 Sq.Ft.

$499,900

MLS#: A4660599

#O6326464

LONGBOAT KEY

779 SAINT JUDES DRIVE N

2 Beds

1 Baths

882 Sq.Ft.

$499,000

MLS#: O6326464

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!!! SELLER will pay up to $20,000 of Buyers closing cost. 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

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. Some online platforms may display inflated tax estimates—actual taxes will depend on exemptions and ownership details. 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.

$469,000

MLS#: A4657888

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

Serene water views of tranquil Bishops Bayou greet you as you enter this immaculate 2nd floor island retreat located in this charming Gulf-to-Bay community. Recently completely updated including impact resistant sliding doors, this lovely hideaway offers nearly 1000 sq. ft. of remodeled living space in peaceful tropical surroundings. Nature lovers will be delighted with the everchanging sunrise views and watching manatees, dolphins & other wildlife at play. When you’re ready to explore, take a short walk to the private beachside “playground” for a round of tennis, shuffleboard, swimming, shelling, paddle boarding, kayaking, or a nice seaside stroll along miles of powder sand beaches. Finish your day by relaxing in your provided beach lounges and enjoying spectacular sunsets while sipping your favorite cocktail. Whitney Beach welcomes large pets, allows 6 monthly rentals per year, and boats up to 33’ can be accommodated when docks are available. After a fun-filled day on the water or at the beach, first-class Restaurants and Eateries are located within a short walk, bike or boat ride, and a Shopping Plaza with a Café, Beauty Salon, Coffee & Smoothie Shop, Pizza, Pilates Studio, 24 hour Gym & a Liquor store etc. are just one block away. Don't delay, start living your dream on Longboat Key today.

LONGBOAT KEY

6800 GULF OF MEXICO DRIVE 203

1 Beds

1 Baths

936 Sq.Ft.

$449,000

MLS#: A4661980

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

Imagine living with these breathtaking water views from the early morning magnificent sunrises to the afternoons with Manatees and Dolphins swimming by your own slice of paradise. Untouched by the recent storms, this one bedroom one bath unit is one the most affordable options on Longboat Key. Tastefully decorated and fully furnished with Luxury Vinyl Laminate floors, Impact Sliders and Windows, Granite Countertops, beautiful premium cabinets and newer appliances in the kitchen. All you need to bring is your clothes and toothbrush.
Located in the amenity rich Longboat Harbour Gated Condominium complex which offers private gated beach access including a pavilion with bathrooms, 4 heated swimming pools, grills, extra storage, shuffle board, putting green, tennis and pickle ball courts, a club house with a billiard and card room, dining hall, wood shop and even an art and craft room. Deep Water Marina to accommodate power or sailboats up to 34 feet, available on a first come first serve basis for under $400 per year. Great rental opportunity. Located mid key with easy access to St Armand’s and Sarasota. Truly a resort lifestyle with an affordable price.

LONGBOAT KEY

4310 FALMOUTH DRIVE 105

1 Beds

1 Baths

747 Sq.Ft.

$429,900

MLS#: A4652643

Ask an L-dock boater, they will tell you its the best dock in the marina. Slip is near the seawall with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, 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. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 63 LOA, usable beam is 23 ft at the head of the slip.

LONGBOAT KEY

2600 HARBOURSIDE DRIVE L-03

None Beds

None Baths

N/A

$425,000

MLS#: A4648812

Charming, rarely available beach-to-bay short term vacation rental. This fully furnished 1bedroom/1bath has an open kitchen, dining and living room combo with a sofa sleeper and a screened porch accommodating four guests comfortably. Assigned parking, storage and laundry facility on site. Great owner/investment opportunity to generate income renting nightly, weekly and monthly. The owner has the option to manage the unit themselves, choose a management company of choice or use the management team on site. It is perfectly situated with access to both a private beach and the bay for a tranquil tropical get away. Enjoy kayaking, heated pool, hot tub, BBQ grill on spacious grounds right off the boat dock which includes a fish cleaning station. The Beach Castle Resort is a short drive from Anna Maria Island, St Armand Circle, and downtown Sarasota loaded with fine dining, entertainment, parks, clubs, marinas, endless shopping and all that the tropical environment offers. Longboat Key offers a tropical lifestyle defined by pristine beaches, world-class golf, and a relaxed atmosphere which is where you will find this one-of-a-kind unit.

LONGBOAT KEY

5310 GULF OF MEXICO DRIVE 18

1 Beds

1 Baths

831 Sq.Ft.

$425,000

MLS#: A4661148

Chic and immaculate 2-bedroom townhome in sought-after Sutton Place, offered turnkey furnished and move-in ready. Thoughtful designer updates include beautifully tiled first floor, quartz kitchen countertops with custom cabinetry and backsplash, updated baths with modern fixtures, smart recessed lighting, and an enclosed lanai for office or family space. Upstairs features elegant dark engineered wood flooring with tiled bath. Spacious bedrooms provide ample closet space, plus a rare private garage with extra storage. The A/C includes an iWave-R ionization generator for enhanced comfort. Sutton Place offers resort-style amenities: two heated pools, marina with boat docks, kayak storage with electric kayak lift (rare and great to have) , BBQ grills, fishing dock, lovely community room with library and kitchen. On-site management. Private, deeded, Gulf-side beach pavilion with parking, restrooms, showers, and car wash. Sutton Place is a pet-friendly community. Bayfront Park is minutes away offering tennis, pickleball, basketball, and dog park. Two tandem kayaks are included.

LONGBOAT KEY

527 SUTTON PLACE T-12

2 Beds

1 Baths

1,448 Sq.Ft.

$425,000

MLS#: A4639006

1 2 3

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