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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

511

# of Listings

2

Avg # of Bedrooms

$858

Avg. $ / Sq.Ft.

$1,508,088

Med. List Price

Browse Long Boat Key Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

108 Properties Found. Page 1 of 8.

**Pirce Improvement ~ Motivated Seller** Step into the island lifestyle you’ve always imagined at Privateer North, located behind the gates of the Longboat Key Club. This CORNER residence with over 1,400 sq. ft. invites you to wake each morning to the sound of waves and natural light streaming through wide glass doors. Sip your coffee on the balcony as Gulf breezes drift in, and in the evening, watch the sky transform with unforgettable Longboat Key sunsets. Inside, thoughtful UPDATES create a fresh, welcoming home. The owners have recently installed a NEW ELECTRIC PANEL, added NEW LIGHTING, FRESH PAINT in areas where needed, and are offering the property FULLY TURN-KEY FURNISHED — so you can start enjoying it from day one. The OPEN LIVING AND DINING area flows easily for entertaining, while the SPLIT-BEDROOM design ensures privacy. The spacious primary suite features a WALK-IN CLOSET and SPA-STYLE BATH, while the guest suite provides a comfortable retreat for family and friends.
Privateer North has just completed a STUNNING MODERNIZATION of its common areas and elevators, complementing its prime beachfront setting. Amenities include a BEACHFRONT POOL AND SPA, FITNESS CENTER, SAUNA, TENNIS and PICKLEBALL courts, CONCIERGE service, and DIRECT BEACH ACCESS — everything you need for a true resort lifestyle. With the new St. Regis Resort just minutes away, and St. Armands Circle and downtown Sarasota within easy reach, this home blends relaxation and sophistication in one of the Gulf Coast’s most desirable locations. Whether a seasonal retreat or full-time residence, Unit 204 offers the perfect balance of LUXURY, LIFESTYLE, and ISLAND CHARM. Call the listing agent today for a V.I.P. tour!

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 204

2 Beds

2 Baths

1,409 Sq.Ft.

$874,900

MLS#: A4662463

Price reduced

Welcome to the perfect opportunity to build your dream home in the coveted Sleepy Lagoon Park on Longboat Key! This desirable lot is located on a saltwater canal with direct access to the Intracoastal Waterway, Sarasota Bay, and the Gulf of Mexico—perfect for boating enthusiasts. With the current structure on the property being removed in the coming weeks, this lot is ready for you to envision and create your ideal waterfront retreat. Two lots from the mouth of the canal, the property offers peekaboo views of the bay and the potential for even more breathtaking vistas with the right elevation and design. Imagine waking up to serene sunrises, taking morning walks along the nearby beach, and catching stunning sunsets every evening. All utilities are in place, making this lot a seamless canvas for your new construction. Enjoy the quintessential Longboat Key lifestyle with nearby amenities such as fine dining, shopping, tennis, fitness clubs, and community parks. This is your chance to own a prime piece of land in one of the most desirable locations on the island. Call today for more details and to schedule your private tour of this exceptional property. Don't miss this rare opportunity to bring your dream home to life!

LONGBOAT KEY

592 JUAN ANASCO DRIVE

None Beds

None Baths

0.23 acres

$999,900

MLS#: A4632452

Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42 villas in Harbour Circle with a community pool and spa and membership access to the deeded private beach club. This home boasts vaulted ceilings, multiple hurricane skylights, hurricane windows, sliders and front door, private atrium and new roof with trusses in 2025, coming completely furnished. Enjoy your morning coffee and dozens of magnificent sunsets on your large two level lanai. Enjoy a walk to Publix, CVS and several Banks close to your community. Only a short drive to Saint Armand's Circle and downtown Sarasota where you will find numerous options for shopping, dinning, theatres, ballet, opera and galleries.

LONGBOAT KEY

2367 HARBOUR OAKS DRIVE

3 Beds

2 Baths

2,219 Sq.Ft.

$999,500

MLS#: A4670055

Welcome to your dream beachfront retreat at The Promenade. This sunny, south-facing seventh-floor residence offers an open, spacious interior encompassing 1585 sq. ft. of living space. It’s waiting for you to make it your own and embrace the captivating views of the Gulf, Sarasota Bay, and downtown Sarasota from its wraparound terrace. With its ideal beachside location, this getaway provides an unparalleled coastal living experience. Wake up to the sights and sounds of the Gulf as it stretches from the beautiful white sandy beaches to the calming waters of Sarasota Bay. Enjoy breathtaking sunrises and sunset afterglows from just about any room, creating a cozy and inviting atmosphere. Step inside this meticulously maintained residence, featuring a spacious and thoughtfully designed layout, walls of glass sliders, plus high ceilings in the building. The eat-in kitchen has picture-perfect bay views and is steps from the dining room. The primary suite is a secluded getaway on the southeast with terrace access, walk-in closets, and an oversized en-suite bathroom. The second bedroom suite is arranged in a split layout for optimal privacy. Situated in a prime location on South Longboat Key, this residence provides easy access to pristine beaches, cultural attractions, and a wide range of recreational activities. The Promenade is a beautifully private, resort-style community that was recently updated. Residents enjoy the convenience of on-site management, a full-service concierge team (7 days/week), a secure lobby, ample under-building parking, security, and a 24-hour staffed guard gate. The options for relaxation are impressive, offering health club facilities with a fitness center, social rooms, four Har-Tru tennis courts, shuffleboard, a Gulfside sundeck featuring a gazebo with a barbecue grill, dining/lounge areas, as well as an oversized heated swimming pool and spa. The perfect finishing touch is the boardwalk leading down to the beach, where you can enjoy lovely Tiki huts.

LONGBOAT KEY

1211 GULF OF MEXICO DRIVE 704

2 Beds

2 Baths

1,585 Sq.Ft.

$999,000

MLS#: A4647136

Price reduced

WOW! The minute you open the front door of this first floor Coastal Retreat Seaside condo, you will be captivated by the shimmering, turquoise Gulf of Mexico Water View and the Panoramic Sandy White Beach in front of you. You'll be eager to get a closer look from the glassed in Florida Room, so you may overlook the beauty of this updated, attractively furnished & decorated first floor residence at Sea Pines, a small 28 unit beach front condo complex on the north end of Longboat Key, Florida. Since purchasing five years ago, these owners have lovingly transformed this almost 1400 square foot, corner unit with extra windows, open concept, two bedroom with En Suite baths & walk in closets to today's coastal contemporary style tastes. Improvements include light oak color Luxury Vinyl wide plank flooring throughout, Samsung stainless steel appliances including washer & dryer, new HVAC installed, updated the primary bedroom with a quartz counter vanity, tiled & glass door shower, and fitted out closet. The condo's interior was painted as well & new, high quality neutral colored living room, dining & bedroom furniture, rugs, lighting & drapery, artwork and a large entertainment center installed. A new tiled roof was installed on this building in 2024. Additional features include impact resistant windows in both bedrooms & the office adjacent to the
kitchen. Plantation shutters cover all these windows. This office area is fitted out with oak cabinetry, desk & drawers, perfect for working at home. The spacious 26-foot-long lanai (Florida Room) can be entered from either the primary bedroom or the living room via sliders. This may be your favorite room with mesmerizing Gulf & beach views over the sea grass pathways to the water. And of course, the magnificent Longboat Key Gulf of Mexico sunsets will thrill you whether watching from your lanai or enjoying on the beach while toasting your good fortune! This turnkey handsomely appointed & attractively furnished seaside retreat offers great rental income if you so wish. There is the potential of keeping on an existing three month (Jan., Feb. & March 2026) tenant. Currently these owners are using RVA Rentals, but a new owner can choose how or if to lease out this unit. Rental friendly Sea Pines can be leased out six times a year with a one month minimum time period. Two additional benefits to this first floor Unit 14 are that these owners have paid $5357 assessment for new landscaping for the complex plus new interior glass sliders will be installed in the living room & primary bedroom and sellers have paid for that as well. Sea Pines has an electronic gated entry for security & privacy. Amenities include a large, heated pool, is large pet friendly & offers excellent rental income possibilities. Charming Longboat Village is nearby with fabulous restaurants like The Shore, Mar Vista, Whitney's, Ventura's & the thriving Whitney Shopping Center. Anna Maria Island is just across the Longboat north end bridge for additional night life entertainment.

LONGBOAT KEY

6951 GULF OF MEXICO DRIVE 14

2 Beds

2 Baths

1,170 Sq.Ft.

$997,500

MLS#: A4648003

A corner A+ junior suite with a walk-down rarely becomes available. It offers quiet and private golf course views and was completely renovated, with the added benefit of being in the hotel program. A separate bedroom from the living room, with a pullout sofa, offers more flexible sleeping arrangements. The living room and bedroom open directly to your private balcony, with stairs leading to the additional open patio area, which is the advantage of the walk-down. There is also added luxury of in-unit laundry. The primary en-suite bath has double sinks and a full shower, with private access for your guests. There is also plenty of closet space. The resort at Inn on the Beach offers a variety of dining experiences, including a pool, a fitness center, a full-service spa, championship golf, tennis and more. Conveniently on southern Longboat Key, just minutes to St. Armands Circle, with its restaurants and shopping, along with Sarasota and all it offers.

LONGBOAT KEY

250 SANDS POINT ROAD 5101

1 Beds

1 Baths

716 Sq.Ft.

$995,000

MLS#: A4672352

Turnkey furnished and positioned directly on the sandy shores of the Gulf of Mexico, this first-floor, direct Gulf-front residence at Beach Castle Resort offers an exceptional blend of beachfront living and proven rental performance. Averaging six figures in annual gross income, this two-bedroom retreat is ideal for personal enjoyment, weekly rentals, or a combination of both—making it one of Longboat Key’s strongest investment opportunities.
The light-filled interior features oversized tile flooring, updated windows and sliders (2009), and a well-appointed kitchen with granite countertops, contemporary cabinetry, modern appliances, and plumbing and electrical upgrades completed in 2006. Designed for effortless coastal living, the open layout seamlessly connects the kitchen, dining, and living areas. Floor-to-ceiling sliders lead to a private patio and screened-in lanai, both just steps from the beach, allowing indoor and outdoor spaces to flow together naturally.
The split-bedroom plan enhances privacy for owners and guests. The primary suite enjoys beautiful Gulf views, private patio access, and a peaceful setting perfect for morning coffee or sunset unwinding. A comfortable second bedroom and full bath complete the guest wing.
Beach Castle Resort is one of the few communities on Longboat Key offering daily, weekly, or monthly rental flexibility, giving owners the freedom to maximize both personal use and rental income. The community’s beach-to-bay amenities include deeded beach access, a sundeck with heated swimming pool and spa, barbecue grilling areas, a fishing pier, and a day dock for boating enthusiasts (first-come basis, no overnight docking). Lush tropical landscaping and well-maintained grounds create a relaxing boutique-resort environment.
Perfectly located on the north end of Longboat Key, the property is minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic walking and biking routes. A short drive south leads to the Longboat Key Club, upscale dining, and the attractions of St. Armands Circle. Downtown Sarasota—home to world-class theater, museums, botanical gardens, professional events, and waterfront parks—is just across the bridge.
With direct Gulf-front views, strong rental history, and an unbeatable location, this Beach Castle residence offers the best of Longboat Key’s coastal lifestyle—whether you’re seeking an investment, a getaway, or both.

LONGBOAT KEY

5311 GULF OF MEXICO DRIVE 3

2 Beds

2 Baths

1,028 Sq.Ft.

$995,000

MLS#: A4672601

This lot is located in The Preserve at Longbeach with plans and design already to go, an exclusive enclave of 12 new homes, light filled and luxurious contemporary homes. Refinement meets relaxation at the north end of LBK in Longbeach Village - where beach-to-bay access with waterfront amenities, al fresco dining, multiple kayak launch points, a neighborhood boat dock and ramp, and a free-spirited lifestyle await. Exhale and enjoy a neighborhood where the waterfront is at your fingertips and peacocks walk the streets. All that makes Coastal Florida living so enchanting is yours to enjoy here - be one of only 12. Located a short distance from the public beach access, the tranquil beaches of Longboat Key are yours to enjoy whether going for a swim in warm, Gulf waters, walking the beach or enjoying the sunset. Whether by boat or car, you're only minutes from world-class dining and shopping, a host of cultural amenities, and nearby barrier islands.

LONGBOAT KEY

6800 LONGBOAT DRIVE S

None Beds

None Baths

0.16 acres

$995,000

MLS#: A4660982

#A4642701

LONGBOAT KEY

4835 GULF OF MEXICO DRIVE 302B

2 Beds

2 Baths

1,393 Sq.Ft.

$995,000

MLS#: A4642701

A TRUE FLORIDA DREAM HOME! WALKING DISTANCE TO ONE OF FLORIDA'S MOST BEAUTIFUL BEACH! This 4 bedroom, 3 bath and 2 car garage home is newly renovated thoughout. Step through the door into the spacious open kitchen and living area that expands into a back additional living area large enough for lounging and a pool table. 4 bedrooms and 3 bathrooms offers ample space for family and friends. The open backyard is great to relax and enjoy the Florida weather. The home is located close to wonderful dining and entertainment. The detached 2 car garage offers plenty of space for paddle boards, kayakes or a small boat storage.

LONGBOAT KEY

608 SAINT JUDES DRIVE

4 Beds

3 Baths

2,106 Sq.Ft.

$989,000

MLS#: D6142646

A one of a kind boat slip available for sale with fortified pilings that are plastic coated and an extended finger pier, deep water, protected, yet easy access to Sarasota Bay and the Gulf at Longboat Key Moorings Marina. This is a 154 ft. T-dock/face dock ready to accommodate a yacht; T of D-dock has 2 50s/100 service outlets. D-19 is 74.5 feet, and D-20 is 79.5 feet, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. This only deep water marina on the West Coast of Florida is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes bath house, laundry facilities, 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. Membership at the Longboat Key Club is available for an additional fee. This slip will accommodate one or two vessels total 149 feet. Usable beam is 25 feet.

LONGBOAT KEY

2800 HARBOURSIDE DRIVE DRIVE D-19 D-20

None Beds

None Baths

N/A

$985,000

MLS#: A4646560

Price reduced

This premier lot and midcentury property, with one of the nicest pools in the area, is ready for its next visionary owner seeking the best of island living on beautiful Longboat Key. It's an ideal opportunity to renovate or build your dream home in the heart of the pedestrian and golf-cart friendly historic Longbeach Village with numerous waterfront restaurants and shops nearby. Located on Longboat Key's north end, this charming midcentury cedar-framed residence is set back on an expansive elevated lot with a deep front yard. The property boasts a private oasis in the rear, complete with a generous resort pool & spa and low-maintenance lawn. Previously updated to blend modern convenience with vintage character, the home was featured in a 2022 Herald-Tribune article as A Sweet Spot on Longboat. Original details include terrazzo floors with flecks resembling green sea glass and distinctive jalousie and awning windows, preserving its unique charm. The open concept living room and kitchen areas showcase cathedral-height ceilings, enhancing the sense of space. Modern drop lighting accents the kitchen and the layout offers easy flow and a relaxed living experience. A vibrant orange exterior and the light-filled rooms contribute to the home’s bright, uplifting atmosphere. Additional spaces include a generous den, a bonus room and an office, offering versatility for various needs such as a fourth bedroom if desired. The outdoor deck is ideal for entertaining or relaxing, surrounded by lush tropical landscaping. This property is one of the neighborhood’s favorites and presents a unique opportunity to reimagine its full potential. Interior photos include images from before and after remediation. All exterior photos of the yard, pool, and spa are current. Enjoy the neighborhood’s Gulf-to-Bay access, perfect for beachcombing, boating, kayaking, and paddleboarding. Launch your kayak just 100 yards away! The neighborhood offers proximity to various waterfront dining, shops, fitness, and the ultimate Florida lifestyle. Longbeach Village uniquely features a convenient community boat ramp, bay access, two fishing piers, public beach access, and several restaurants, cafes, and fitness studios, all just a few blocks away from this sizeable standout property.

LONGBOAT KEY

711 RUSSELL STREET

3 Beds

2 Baths

1,862 Sq.Ft.

$975,000

MLS#: A4636733

Price reduced

#A4646346

LONGBOAT KEY

3235 GULF OF MEXICO DRIVE A305

2 Beds

2 Baths

1,260 Sq.Ft.

$975,000

MLS#: A4646346

Wonderful "Manhattan Style" beachfront Condo with sweeping views of Sarasota Bay and views of the Gulf now available at the popular Islander Club on LBK. This gorgeous beachfront renovation was completed 4 years ago and truly shows all the craftmanship that went into the process under the owner's direction. Open kitchen beings the morning light into the room for enjoying your coffee or tea as you gaze across the sparking blue waters of the bay. Large 38ft balcony also has views of bay and a bit of the Gulf of Mexico. The Primary suite is a comfortable 13X20 which accesses the balcony and has a large walk-in closet. It is light and bright and a restful haven away from the main living area. The Islander club has recently renovated their clubhouse. The gym overlooks the gulf and the pool. There is a conference room, library, and an Olympic size heated pool, not to mention their Har-Tru tennis courts. The Location is very convenient. The shops of Bay Isles with the Publix and CVS are just a couple of minutes away. It's only 10 minutes to World renown St Armand Circle. Make this your permanent home or your week-end getaway. Secured Building . At The Islander Club "Everyday is a Holiday and Life is an endless vacation.

LONGBOAT KEY

2295 GULF OF MEXICO DRIVE 115S

2 Beds

2 Baths

1,235 Sq.Ft.

$975,000

MLS#: A4670081

Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush landscaping and upscale tropical ambiance create an idyllic setting along the stunning Gulf of Mexico, perfect for both personal enjoyment and income generation. Amenities at Seagrape Inn include a private entrance to each condo, a private heated pool, a private beach area with lounge chairs and umbrellas, on-site laundry and ice machine, upgraded Wi-Fi throughout the resort, cable TV, a gazebo with a gas BBQ grill, and beach towels and linens. Unit 7, perched on the second floor, provides breathtaking views of the ocean and the inviting pool below. Upon entry, the condo exudes sophistication, with a thoughtfully designed living space that seamlessly connects the living room, dining area, and upgraded kitchen. The kitchen, recently renovated to perfection, features new cabinets, countertops, recessed lighting, plumbing fixtures, and state-of-the-art appliances. The entire unit has been enhanced with new waterproof LVP flooring, fresh interior paint, and modern light fixtures, ensuring a contemporary and elegant aesthetic throughout. Both bedrooms are tastefully furnished, offering serene retreats after a day at the beach. The bathrooms have been completely remodeled, showcasing new vanities, tile work, shower doors, and plumbing fixtures. Step onto the screened balcony to savor unparalleled views of the ocean, pool, and lush greenery a perfect spot to relax and soak in the tranquil surroundings. Beyond the condo's exquisite interior, significant exterior improvements have been made, including the installation of hurricane windows and doors, new deck waterproofing, and exterior painting. The convenience of a designated parking spot adds to the property’s appeal. Located in a prime area of Longboat Key, this condo provides easy access to the beach, Gulf, and nearby restaurants and shops. Whether you're seeking a lucrative investment or a luxurious personal retreat, this beachfront condo offers an extraordinary opportunity to experience the best of coastal living in an unparalleled location.

LONGBOAT KEY

5125 GULF OF MEXICO DRIVE 7

2 Beds

2 Baths

961 Sq.Ft.

$975,000

MLS#: N6141238

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