Longboat Key Homes for Sale and Rent by Zip Code

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Newest Longboat Key Homes by Zip Code

  • 2525 GULF OF MEXICO DR #3D, LONGBOAT KEY, FL - MLS# A4696213

    34228 - A4696213 - 2525 GULF OF MEXICO DR #3D, LONGBOAT KEY, FL 34228
    1 Day on yellowkey

    $1,650,000 | Condo | 2 beds | 2.0 baths | 1 car

    Professional Photo's coming soon. Wake up to breathtaking, direct panoramic views of the Gulf of Mexico from this stunning third-floor beachfront residence on Longboat Key. Perfectly positioned to capture endless turquoise waters and spectacular sunsets, this coastal retreat offers unobstructed Gulf views, creating a serene backdrop for everyday living. The completely updated condo features two bedrooms, two baths, a spacious great room, dining area, and a kitchen with a charming breakfast nook. Walls of impact glass flood the interior with natural light, while floor-to-ceiling windows in both bedrooms showcase the ever-changing beauty of the shoreline. A wraparound balcony provides the perfect setting to enjoy morning coffee, coastal breezes, and mesmerizing sunsets over the Gulf. Ideally located mid-island, this residence offers the perfect balance of tranquility and convenience. Bay Isles Shoppes is just across the street, offering Publix, CVS, banking, dining, the Longboat Key Tennis Center, and Bayfront Park. World-renowned St. Armands Circle is only four miles away, while downtown Sarasota's acclaimed dining, shopping, arts, and entertainment are within a short seven-mile drive. Residents of Islands West enjoy an exceptional Gulf-front lifestyle with an impressive collection of resort-style amenities. The 15-story community features secure key-fob entry, a heated beachfront pool and spa, outdoor grilling and lounge areas, tennis and pickleball courts, and dedicated storage for bicycles, kayaks, and paddleboards. The clubhouse is currently being transformed to include a stylish social room with library, state-of-the-art fitness center, and catering kitchen. Pet lovers will appreciate the welcoming two-pet policy. Experience the ultimate beachfront lifestyle where spectacular views, resort-inspired amenities, and an unbeatable Longboat Key location come together in one extraordinary residence.

    Contact Yellowkey Agent

    Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
    Listing Agent: Midge Mccarthy (941-809-3800)

  • 528 FOREST WAY, LONGBOAT KEY, FL - MLS# A4695863

    34228 - A4695863 - 528 FOREST WAY, LONGBOAT KEY, FL 34228
    4 Days on yellowkey

    $585,000 | Condo | 2 beds | 2.5 baths | 1 gar

    Elevated, renovated, fully furnished, pet friendly, close to the beach AND a short term rental opportunity on Longboat Key?! This is the one you've been looking for! You don't have to be a tennis player to understand the value of this fabulous townhome in Cedars Tennis Club. This 2 bedroom, 2 and a half bath condo is the perfect island escape. Beautifully updated and furnished, all you’ll need to bring is your bathing suit and a toothbrush to start enjoying island life to the fullest. Add to it a short term two week rental policy, this could also be your perfect investment property. Current annual income has been around $50,000, but that also includes a lot of family enjoyment in between. New impact windows, a new roof, 2021 air conditioning units and a private garage make this condo even more appealing. Spend your days in the sun with just a short walk to the beach or the Bay. Enjoy the community swimming pool, with a fabulous tiki bar. Join the club to enjoy the fitness center and tennis privileges. Take a bike ride on 11 miles of bike paths down the island or a walk to Joan Durante Park. The cultural mecca of downtown Sarasota is just a short drive away. And don’t forget to make time to see the stunning evening sunsets. The Longboat Key lifestyle is waiting for you!

    Contact Yellowkey Agent

    Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
    Listing Agent: Jodene Moneuse, Pa (941-302-4913)

  • 3271 BAYOU RD, LONGBOAT KEY, FL - MLS# TB8515918

    34228 - TB8515918 - 3271 BAYOU RD, LONGBOAT KEY, FL 34228
    5 Days on yellowkey

    $1,995,000 | Single Family Home | 4 beds | 4.0 baths | 3 gar

    Nestled behind the gates of prestigious Bay Isles on Longboat Key, this exceptional residence offers over 3,000 square feet of thoughtfully designed living space surrounded by lush tropical landscaping and just moments from the Gulf of Mexico. Combining timeless architecture, spacious interiors, and resort-style outdoor living, this home delivers the privacy and elegance that define the Longboat Key lifestyle. A grand entry welcomes you into an open and inviting floor plan featuring soaring ceilings, abundant natural light, and generous living and entertaining spaces. The expansive great room flows seamlessly into the dining area and well-appointed kitchen, complete with ample cabinetry, extensive counter space, and a convenient wet bar for effortless entertaining. The first-floor primary suite serves as a private retreat with a spacious bedroom, large walk-in closet, and luxurious en-suite bath. Additional guest bedrooms are thoughtfully positioned for privacy and comfort, while the second floor offers a private guest suite with balcony access—perfect for visitors seeking their own space and enjoying tropical views. Designed for year-round enjoyment, the screened outdoor living area is a true highlight. Relax poolside in the sparkling heated pool and spa, entertain under the covered lanai, or unwind amidst the lush tropical surroundings that create a secluded backyard oasis. Located within the highly sought-after Bay Isles community, residents enjoy 24-hour gated security, beautifully maintained grounds, and exclusive access to the private Bay Isles Beach Club on the Gulf of Mexico. Just minutes away are the Longboat Key Club's championship golf courses, tennis facilities, marina, waterfront dining, boutique shopping, and renowned St. Armands Circle. Offering the perfect blend of luxury, privacy, and coastal convenience, this exceptional Longboat Key residence presents a rare opportunity to enjoy one of Sarasota's most desirable island lifestyles.

    Contact Yellowkey Agent

    Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
    Listing Agent: Robert Johnson (813-364-2250)

  • 2301 GULF OF MEXICO DR #12N, LONGBOAT KEY, FL - MLS# A4695851

    34228 - A4695851 - 2301 GULF OF MEXICO DR #12N, LONGBOAT KEY, FL 34228
    7 Days on yellowkey

    $1,225,277 | Condo | 2 beds | 2.0 baths | 1 car

    A rare opportunity to own a beautifully reimagined Gulf-front residence at the prestigious Islander Club on South Longboat Key. Completely renovated with sophisticated coastal elegance, this exceptional beachfront condominium offers the convenience of first-floor walk-out living with direct access to the resort-style beachfront pool and the pristine white sands of the Gulf of Mexico. Walls of glass frame breathtaking panoramic Gulf views while filling the residence with natural light and spectacular sunsets. Thoughtfully redesigned with high-end finishes, the residence features a luxurious open-concept floor plan, a stunning chef's kitchen, beautifully appointed baths, and seamless indoor-outdoor living. The private beachfront terrace serves as an extension of the living space, creating the perfect setting for morning coffee, sunset cocktails, and effortless entertaining. Ideally positioned on the coveted south end of Longboat Key, this residence offers the privacy and comfort of a beachfront home with the convenience of luxury condominium living. Residents enjoy an impressive collection of amenities including 400 feet of private beachfront, an Olympic-size beachfront pool, a newly renovated fitness and community center, Har-Tru tennis courts with planned pickleball additions, on-site management, gated entry, and a highly desirable owner-to-owner rental program. Located just minutes from St. Armands Circle and vibrant downtown Sarasota, this exceptional residence places world-class dining, boutique shopping, cultural attractions, and marina amenities within easy reach. An extraordinary opportunity to experience refined Gulf-front living at one of Longboat Key's most sought-after beachfront addresses.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
    Listing Agent: Leah George (941-780-0597)

  • 2301 GULF OF MEXICO DR #11N, LONGBOAT KEY, FL - MLS# A4695843

    34228 - A4695843 - 2301 GULF OF MEXICO DR #11N, LONGBOAT KEY, FL 34228
    7 Days on yellowkey

    $1,225,277 | Condo | 2 beds | 2.0 baths | 1 car

    Experience the tranquility of Gulf-front living from this beautifully updated residence at the prestigious Islander Club on South Longboat Key. Ideally positioned on the highly desirable north side of the building, this exceptional beachfront condominium enjoys a uniquely private setting with expansive views, abundant natural light, and a peaceful atmosphere rarely found in condominium living. Offering the convenience of first-floor walk-out access, the residence lives much like a private beachfront home, with direct access from the terrace to the lush grounds, beachfront pool, and the pristine white sands of the Gulf of Mexico. Floor-to-ceiling glass showcases sparkling Gulf views, breathtaking sunsets, and refreshing coastal breezes throughout the day. Thoughtfully updated and impeccably maintained, the residence offers comfortable and elegant living spaces ready to be enjoyed immediately . The open layout seamlessly connects indoor and outdoor living, creating an ideal setting for both relaxing and entertaining. Residents of The Islander Club enjoy an exceptional collection of amenities, including 400 feet of private beachfront, an Olympic-size beachfront pool, a newly renovated fitness and community center, Har-Tru tennis courts with planned pickleball additions, on-site management, gated entry, library, conference facilities, and a highly desirable owner-to-owner rental program. Located just minutes from St. Armands Circle and downtown Sarasota, this residence offers convenient access to world-class dining, boutique shopping, cultural attractions, marinas, and the very best of Florida's Gulf Coast lifestyle. A rare opportunity to enjoy privacy, beachfront living, and the unmatched beauty of Longboat Key at one of the island's most sought-after addresses.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
    Listing Agent: Leah George (941-780-0597)

  • 1591 GULF OF MEXICO DR #619, LONGBOAT KEY, FL - MLS# A4695816

    34228 - A4695816 - 1591 GULF OF MEXICO DR #619, LONGBOAT KEY, FL 34228
    7 Days on yellowkey

    $78,000 | Condo | 4 beds | 4.5 baths | 3 gar

    An exceptionally rare opportunity to lease one of the most exclusive waterfront residences ever offered on Florida’s Gulf Coast. Positioned within the iconic St. Regis Residences on Longboat Key, this extraordinary four-bedroom, four-and-a-half-bath condominium redefines annual luxury living with an unrivaled level of privacy, sophistication, and world-class service. Arrive via private elevator entry that opens directly into your personal residence, where breathtaking panoramic Gulf and Sarasota Bay views unfold from nearly every room. Designed for the most discerning resident, this one-of-a-kind home seamlessly blends contemporary elegance with resort-inspired comfort across expansive indoor and outdoor living spaces. A spectacular wraparound terrace serves as a true extension of the residence, complete with a private pool overlooking turquoise Gulf waters, dramatic sunsets, and sparkling bay vistas — creating an unparalleled setting for entertaining or quiet relaxation. Inside, every detail has been thoughtfully curated to deliver an uncompromising luxury experience. A state-of-the-art integrated sound system flows throughout the residence, while a hidden speakeasy and private wine room offer an unforgettable level of exclusivity rarely found in condominium living. The grand primary suite is a private sanctuary featuring floor-to-ceiling windows with sweeping water views, a spa-inspired ensuite bath, and an extraordinary dressing room designed to function as a dedicated walk-in closet suite unto itself. Residents enjoy full-time concierge and butler service, delivering the legendary St. Regis standard directly to your door. In addition to exclusive resident amenities, tenants also enjoy access to the world-renowned hotel amenities, creating a seamless five-star lifestyle unlike anything else available on the market today. Close Proximity to IMG Academy. This is more than a residence — it is a statement of prestige, privacy, and elevated waterfront living. Opportunities of this caliber are exceedingly rare. There is simply no comparable product currently available on Longboat Key. Experience the absolute pinnacle of luxury coastal living at the St. Regis Residences Longboat Key.

    Contact Yellowkey Agent

    Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)
    Listing Agent: Jaime Barcelo (941-275-3233)

  • 2301 GULF OF MEXICO DR #33N, LONGBOAT KEY, FL - MLS# A4695318

    34228 - A4695318 - 2301 GULF OF MEXICO DR #33N, LONGBOAT KEY, FL 34228
    7 Days on yellowkey

    $1,199,000 | Condo | 2 beds | 2.0 baths | 1 car

    Experience breathtaking beachfront living in this rare direct Gulf-front residence at the prestigious Islander Club on Longboat Key. This two-bedroom, two-bath condominium showcases panoramic Gulf of Mexico views from every room, including the living room, primary suite and guest bedroom, creating a spectacular coastal backdrop throughout the home. One of the exceptional features of this residence is its oversized deeded beachfront terrace, a rare offering within the community. Only a select few residences at the Islander Club enjoy this expansive outdoor space, which enhances the home's connection to the beach and provides an unparalleled vantage point for taking in sweeping Gulf views and spectacular sunsets. Wake up to the sound of the waves, enjoy stunning water views from nearly every location and embrace the relaxed luxury of Longboat Key beachfront living. The Islander Club is a sought-after community with 400 feet of private beach frontage. Islander Club offers residents on-site management, a heated pool, renovated clubhouse, billiards and table tennis room, fitness center, saunas and two Har-Tru tennis courts. The shopping, dining and cultural attractions of St. Armands Circle and downtown Sarasota are just a short drive away.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
    Listing Agent: Chris Wetzig (941-350-8083)

  • 1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL - MLS# A4694983

    34228 - A4694983 - 1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL 34228
    8 Days on yellowkey

    $2,125,000 | Condo | 3 beds | 3.0 baths | 1 gar

    Sweeping sunrise to sunset views define this beautifully reimagined 7th floor residence at the Promenade on Longboat Key. Fully renovated in 2026, this three-bedroom, three full bath home offers floor to ceiling windows, abundant natural light, and 180- degree views of both the Gulf of Mexico and Sarasota Bay. The double door entry opens to a freshly painted residence with new luxury plank flooring, nine-foot ceilings and modern lighting throughout. This residence is designed for entertaining with a large open living area and a full wet bar and wine refrigerator. The kitchen features quartz countertops and full quartz backsplash, Sub-Zero refrigerator, Cafe stove and double convection oven, and matching panel dishwasher. The custom modern white soft closed cabinetry with polished nickel hardware provides a stylish look as well as large amounts of storage and pantry space. A reimagined kitchen layout allows for a separate island that can be used for morning coffee, workspace or meal preparation all while enjoying gorgeous bay views. The primary suite features a spa-like oasis with new enlarged glass enclosed shower featuring waterfall and wall shower-heads, all quartz countertops, dual sinks, polished nickel faucets, fully backlit electric mirrors, separate water closet, linen storage and a custom designed walk-in closet. The two additional bedrooms each offer private bathrooms, one with a dazzling walk-in shower and the other with a new bathtub/shower. The renovations included removing all popcorn ceilings, updates to electrical and plumbing systems, all new fire sprinkler hardware and base boards. The full-sized laundry room includes new storage cabinetry, full sized washer/dryer and a wash-sink. All new interior doors fitted with Emtek polished nickel door hardware. The residence includes a private storage locker that is humidity and temperature controlled and a deeded underground parking space. The Promenade has undergone significant renovation over the past few years and features elegant marble foyer, 24-hour gate security, manned concierge desk, his and hers fitness rooms with shower and sauna, luxurious party rooms, EV charging station, a well-maintained pool deck and hot tub, verdant tropical landscaping and dual BBQ areas. The beach is located directly behind the building and features a secure entrance and beach chairs. There are also 4 Har-Tru tennis courts to complete the Longboat Key lifestyle. The Promenade is located near the south end of Longboat Key, minutes from St. Armand's Circle and the restaurants and arts offerings of downtown Sarasota. The Longboat Key Club and its golf, tennis and marina offerings is available for membership and just outside the property.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
    Listing Agent: Maggie Hicks (941-321-1759)

  • 3460 WINDING OAKS DR #38, LONGBOAT KEY, FL - MLS# A4695005

    34228 - A4695005 - 3460 WINDING OAKS DR #38, LONGBOAT KEY, FL 34228
    8 Days on yellowkey

    $1,150,000 | Condo | 3 beds | 3.5 baths | 2 gar

    Tucked within Winding Oaks, one of Longboat Key’s most sought-after villa communities, this 3BR/3BA residence offers the scale and comfort of a single-family home paired with the simplicity of maintenance-free living. From the paver drive and walkway to the stepped front entry, the residence creates an inviting first impression before opening into a home defined by volume, light and connection to the outdoors. Step inside and soaring ceilings immediately create a sense of openness, while high-set windows invite natural light to move throughout the living spaces. Tile flooring and soft neutral tones create a clean backdrop that complements the peaceful setting just beyond the glass. Renovated in November 2025, the kitchen has been thoughtfully opened and redesigned into a true centerpiece for gathering and everyday living. A substantial island with seating anchors the space, along with stone countertops, white cabinetry, stainless steel appliances, a range hood, wine refrigerator and tile backsplash. An abundance of windows and an adjoining sitting area create a bright, welcoming space whether hosting guests or enjoying a quiet morning. The dining area transitions naturally into the living room, where cathedral ceilings, a corner fireplace and sliding glass doors connect the interior to the outdoors. Beyond, an expansive screened deck overlooks the community lake and fountain, creating a peaceful setting with multiple areas for dining, relaxing or entertaining. Privacy walls on either side enhance the feeling of seclusion while keeping the water views front and center. The primary suite is spacious and calming, featuring vaulted ceilings, engineered wood floors, a wall of sliding glass doors opening to the deck and a large walk-in closet with extensive built-ins. Also renovated in November 2025, the primary bath offers dual vanities, a walk-in shower, dressing area and separate water closet. Guest accommodations are equally well planned. One bedroom includes an en suite bath and walk-in closet, while another is currently configured as an office space with sliding glass doors opening to a private patio. Updated baths throughout, an in-residence laundry room and a 2-car garage add convenience. Set within the Harbourside golf course community, Winding Oaks offers a serene environment with a gated entrance, community pool and spa, and access to the full range of Bay Isles amenities, including deeded beach access through the private Bay Isles Beach Club.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
    Listing Agent: Bruce Myer (941-376-5311)

  • 546 SPANISH DR S, LONGBOAT KEY, FL - MLS# A4694824

    34228 - A4694824 - 546 SPANISH DR S, LONGBOAT KEY, FL 34228
    9 Days on yellowkey

    $509,000 | Condo | 2 beds | 2.0 baths | 1 car

    Tucked within the waterfront community of Spanish Main Yacht Club on the north end of Longboat Key, this fully renovated detached villa offers a timeless coastal flair just steps from the beach. A true hidden gem and slice of paradise, residents enjoy private deeded beach access to the Gulf of America, a deep water marina with affordable boat slips, and the ultimate boating lifestyle with easy access to waterfront restaurants and open waters. This light and bright 2-bedroom, 2-bath residence is being offered turnkey furnished. Featuring an open floorplan with luxury vinyl plank flooring, impact windows and doors, custom window shades throughout, and a spacious Florida room ideal for additional living or entertaining space. The beautifully updated kitchen showcases quartz countertops, stainless steel appliances, abundant custom cabinetry with soft-close drawers, and a large seating island perfect for gathering. Additional highlights include an interior laundry room with stackable washer and dryer, water softener system, stone paver patio, covered parking, and private driveway. Spanish Main Yacht Club is a vibrant and active 55+ community offering a heated waterfront pool, shuffleboard, social events, pet-friendly policies, maintenance-free living, and one of the most desirable 40-slip marinas on Longboat Key. Ideally located just minutes from St. Armands Circle, Sarasota, and Anna Maria Island, this exceptional Longboat Key retreat is ready for immediate enjoyment.

    Contact Yellowkey Agent

    Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
    Listing Agent: Jackie Griese (941-718-0045)

  • 820 SPANISH DR S #., LONGBOAT KEY, FL - MLS# A4695386

    34228 - A4695386 - 820 SPANISH DR S #., LONGBOAT KEY, FL 34228
    9 Days on yellowkey

    $3,000 | Condo | 2 beds | 2.0 baths | 1 car

    Coastal Living at Its Finest in the Spanish Main Yacht Club! Discover your perfect Florida retreat in this beautifully maintained, free-standing 2-bedroom, 2-bathroom villa located on the highly coveted southern end of Longboat Key at 820 Spanish Dr S. Offering 1,390 square feet of bright, open living space, this single-story residence perfectly blends maintenance-free comfort with an active, coastal-resort lifestyle in a premier 55+ community.Step inside to find a spacious layout featuring a generous living area centered around a cozy fireplace, a classic split-bedroom design for optimal privacy, and a wonderful enclosed porch perfect for morning coffee or unwinding after a day in the sun. The property also features a durable concrete tile roof, central A/C, a dedicated utility space, and an open porch area to soak in the Gulf breezes. Please note this is a strictly no-smoking and no-pets property.Available in-season for $6,000 per month turnkey, and off-season for $3,000 per month turnkey. Situated in Manatee County’s renowned Spanish Main Yacht Club, an established and highly desirable waterfront community zoned LBK_R-3MX, residents enjoy unparalleled amenities including a private marina (with boat slips available for a nominal fee), a heated community pool overlooking the active harbor, a lively clubhouse, shuffleboard, and deeded private beach access just steps across the street to the pristine sands of Longboat Key. Located within easy reach of local island dining, area attractions, and the highly-rated Anna Maria Elementary school district, this waterfront gem offers the ultimate island lifestyle.

    Contact Yellowkey Agent

    Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
    Listing Agent: Geoff Scalera (941-321-4158)

  • 408 GULF OF MEXICO DR #2112, LONGBOAT KEY, FL - MLS# A4695317

    34228 - A4695317 - 408 GULF OF MEXICO DR #2112, LONGBOAT KEY, FL 34228
    9 Days on yellowkey

    $39,500 | Dock-Rackominium

    Welcome to Slip #2112 at The Boathouse on Longboat, rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This slip accommodates boats up to 23'6"Lx8'6"Wx7'2"H (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and even the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

    Contact Yellowkey Agent

    Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
    Listing Agent: Daniel Treiman (917-657-7495)

  • 450 GULF OF MEXICO DR #303, LONGBOAT KEY, FL - MLS# A4695053

    34228 - A4695053 - 450 GULF OF MEXICO DR #303, LONGBOAT KEY, FL 34228
    11 Days on yellowkey

    $2,400 | Condo | 2 beds | 2.0 baths | 1 car

    Annual furnished rental: Discover the ultimate island lifestyle in this comfortably furnished 2-bedroom, 2 bath, unit located in the highly sought-after community of Bay Harbour on the southern end of Longboat Key. Just minutes from St. Armands Circle, downtown Sarasota, restaurants, shopping, county tennis and pickleball courts, walking trails, parks and of course – Longboat Key public beach accesses along Gulf of Mexico Drive. Doesn’t get much better than this! Entering the condo you immediately feel the spaciousness and inviting interior. Just bring your personal possessions for an easy move-in! The updated kitchen offers granite counter tops, stainless appliances and both an eat-in space to share a meal along with full-size laundry closet. The kitchen also overlooks the dining and living areas, which are great for entertaining friends and family. From most rooms you’ll have a lovely view of the pool and partial view of the Bay. This split-plan layout provides privacy for both you and your guests. Master suite features a large bedroom, plenty of closet space and generous size private bath. Guest bedroom offers a full and day bed for your guests and family with nice size closet. Second bath is conveniently located next to the guest bedroom. Perfect for unwinding after a day of sunbathing or beachcombing you can relax with your favorite beverage overlooking the pool and water views. If you’re actively inclined, step outside and immerse yourself in the beauty of Sarasota Bay, where you'll enjoy direct access to a kayak launch or a work out in the fitness area – or just lounge by the pool.Bay Harbour is a true gem which offers a wealth of amenities, including a heated waterfront pool, kayak storage, a floating kayak launch, a fitness center, assigned covered parking, and inside locked bike storage. Take advantage of excellent fishing on property, or simply relax and take in the views. Bay Harbour offers the perfect combination of location and lifestyle. Don’t miss your chance to call this home! Background Check required, along with First, last and Security deposit. Sorry, but no smoking nor pets are allowed.

    Contact Yellowkey Agent

    Listing is courtesy of: GULF COAST RENTAL HOMES&CONDOS (941-212-1972)
    Listing Agent: Diann Thelen (941-920-0758)

  • 3563 FAIR OAKS LN, LONGBOAT KEY, FL - MLS# A4695291

    34228 - A4695291 - 3563 FAIR OAKS LN, LONGBOAT KEY, FL 34228
    11 Days on yellowkey

    $2,650,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar

    Behind the private gates of Bay Isles, this exquisitely renovated four-bedroom, four-and-a-half-bath residence in Queens Harbour presents a refined interpretation of coastal living, where timeless elegance, thoughtful design, and relaxed Longboat Key luxury come together seamlessly. Beautifully appointed and move-in ready, the home welcomes you with an open, light-filled floor plan enhanced by hardwood flooring throughout, fresh interior paint, new baseboards, plantation shutters, new hurricane-impact windows throughout, and vaulted ceiling in the great room. Designer details elevate the interiors, including Philip Jeffries grasscloth in the foyer and Serena & Lily wallpaper in the powder bath, adding texture, warmth, and sophistication. At the heart of the home, the newly redesigned chef’s kitchen blends classic style with everyday functionality. Features include custom shaker-style cabinetry, an oversized island, honed marble countertops, a Viking Professional Series gas cooktop, new built-in refrigerator, all new appliances, extended upper and lower cabinetry, and a charming breakfast area. The kitchen opens gracefully to the main living spaces, creating an elegant yet comfortable setting for entertaining and daily living. The desirable floor plan offers a spacious first-floor primary suite, an additional first-level guest suite with en-suite bath, a private office, formal dining room, and expansive great room. Each space has been thoughtfully updated to feel polished, inviting, and effortlessly livable. Outdoors, a tranquil private retreat awaits with a covered patio, pool and spa, fenced yard, and lush tropical landscaping, offering the ideal backdrop for quiet relaxation or intimate gatherings. Queens Harbour residents enjoy the coveted Bay Isles lifestyle, including private access to the Bay Isles Beach Club on the Gulf of Mexico. Optional membership at the Longboat Key Club provides additional access to golf, tennis, boating, dining, and resort-style amenities. Elegant, beautifully updated, and perfectly positioned within one of Longboat Key’s most desirable gated communities, this Queens Harbour residence captures the essence of refined island living.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
    Listing Agent: Kelly Gettel (941-315-2525)

  • 2185 GULF OF MEXICO DR #212, LONGBOAT KEY, FL - MLS# A4694656

    34228 - A4694656 - 2185 GULF OF MEXICO DR #212, LONGBOAT KEY, FL 34228
    12 Days on yellowkey

    $1,995,000 | Condo | 3 beds | 2.0 baths | 2 gar

    Discover elevated Gulf-front living in this rarely available 3BR/3BA residence spanning 2,448 square feet in the prestigious Villa Di Lancia on Longboat Key. Perfectly positioned to capture panoramic Gulf views, this spacious condominium offers the ideal blend of privacy, security, and effortless coastal luxury. Expansive glass sliders, transom windows, and high ceilings fill the interiors with natural light, enhancing open living spaces designed for both relaxed living and entertaining. The great room flows seamlessly to a generous covered terrace, creating a year-round indoor-outdoor lifestyle. A unique private walk-out with spiral staircase provides direct access to the lush grounds, resort-style pool, and the pristine Gulf beach just steps away—an exceptional feature rarely found in condominium living. The well-appointed kitchen features a center island, solid surface countertops, and a casual dining area, perfectly suited for hosting family and guests. The primary suite serves as a tranquil retreat with terrace access, a sitting area, and a spacious bath with dual vanities, soaking tub, and glass-enclosed shower. Two additional guest bedrooms offer comfort and privacy. Villa Di Lancia is one of Longboat Key’s most sought-after beachfront communities, offering 440 feet of private beach, gated security, a beachfront lap pool and spa, fitness center, clubhouse, Har-Tru tennis courts, and pet-friendly living. The residence includes two climate-controlled garage parking spaces. Turnkey furnishings are available. Enjoy a lifestyle defined by convenience and sophistication—just minutes to the Longboat Key Club’s golf, tennis, and marina, the world-class shopping and dining of St. Armands Circle, and the vibrant cultural scene of downtown Sarasota, including fine dining, theaters, opera, ballet, and art galleries. Schedule your private showing today and experience the best of Longboat Key Gulf-front living.

    Contact Yellowkey Agent

    Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
    Listing Agent: Steve Walter (941-809-0907)

  • 2020 HARBOURSIDE DR #446, LONGBOAT KEY, FL - MLS# A4695127

    34228 - A4695127 - 2020 HARBOURSIDE DR #446, LONGBOAT KEY, FL 34228
    13 Days on yellowkey

    $5,950 | Condo | 2 beds | 2.0 baths | 1 gar

    Experience luxury island living in this beautifully remodeled 2-bedroom, 2-bath residence located in the highly sought-after Fairway Bay community within Bay Isles on Longboat Key. Available for immediate occupancy, this turnkey furnished coastal retreat offers flexible lease terms from 6 to 12 months. Step inside to discover a bright and open floor plan featuring upscale contemporary finishes, , updated flooring, a stunning modern kitchen with premium appliances, and elegantly renovated bathrooms. The spacious primary suite provides a peaceful retreat, while the second bedroom offers comfortable accommodations for guests or an ideal home office. Expansive living spaces and a private balcony create the perfect setting to relax and enjoy the Florida lifestyle. Residents of Fairway Bay enjoy an exceptional array of resort-style amenities, including a heated community pool, a beautifully maintained clubhouse, and a fully equipped fitness center. Tennis and pickleball enthusiasts will appreciate access to two regulation tennis courts that can also be configured into four pickleball courts, offering year-round recreation just steps from home. As part of the exclusive Bay Isles community, residents also enjoy access to the private Bay Isles Beach Club, featuring deeded Gulf-front beach access with some of Longboat Key's most beautiful sand beaches. The Beach Club offers gated parking, picnic areas, grills, restrooms, and the perfect setting to enjoy spectacular Gulf sunsets. Outdoor enthusiasts will also appreciate access to the Bay Isles marina area and kayak launch with direct access to Sarasota Bay. Ideally situated on Longboat Key, this residence is just minutes from St. Armands Circle, Longboat Key Club, championship golf courses, waterfront dining, marinas, boutique shopping, and the cultural attractions of downtown Sarasota. Whether you're seeking a seasonal retreat or an extended island stay, this residence offers the perfect combination of luxury, convenience, and coastal living. Available immediately with lease terms ranging from 6 to 12 months.

    Contact Yellowkey Agent

    Listing is courtesy of: VIVE REALTY (941-600-8162)
    Listing Agent: Jeffrey Swanson (248-938-1775)

  • 7143 LA LENAIRE DR, LONGBOAT KEY, FL - MLS# A4694196

    34228 - A4694196 - 7143 LA LENAIRE DR, LONGBOAT KEY, FL 34228
    14 Days on yellowkey

    $5,995,000 | Single Family Home | 4 beds | 4.0 baths | 4 car

    Private island living on Jewfish Key, one of eight homes, accessible by boat only. This rare offering presents a lifestyle few will ever experience: a secluded island sanctuary surrounded by the turquoise waters of Longboat Pass and the Gulf Coast’s natural beauty. An address like this comes up for sale about once a generation. 7143 La Lenaire is on the market for the first time in more than two decades. The home is a custom built, over 2,700 square feet of living space designed to embrace panoramic water views and effortless indoor-outdoor living, four bedrooms and four baths, finished in 2011 on a 1.24-acre titled lot with roughly 300 feet of water frontage. From the island you are minutes by water to Longboat Key, St Armands Circle, and Anna Maria Island. Every room captures breathtaking western-facing vistas, creating a constant backdrop of sparkling water, coastal breezes, and unforgettable sunsets. The main living areas open onto covered outdoor space and frame the sunset over the intercoastal waters, and the evening light fills the rooms. It was built to handle a quiet weekend or a full house of guests. The private deep-water dock provides immediate boating access to Sarasota Bay, the Intracoastal Waterway, Longboat Key Pass, and the Gulf of Mexico, making this a true boater’s paradise. Jewfish Key is a hidden gem spanning approximately 38 acres, offering a level of privacy and tranquility rarely found along Florida’s Gulf Coast. Surrounded by pristine shoreline, sandbars, native wildlife, and crystal-clear waters, the island delivers an unmatched blend of exclusivity and natural beauty while still being conveniently located near Longboat Key, Anna Maria Island, and Sarasota’s world-class dining, shopping, and entertainment. Whether used as a private family compound, luxury waterfront getaway, or one-of-a-kind investment opportunity, 7143 La Lenaire Drive represents a truly irreplaceable island lifestyle. Turn Key - Furnished.

    Contact Yellowkey Agent

    Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
    Listing Agent: Michelle Ward (941-920-2460)

  • 1211 GULF OF MEXICO DR #105, LONGBOAT KEY, FL - MLS# A4694733

    34228 - A4694733 - 1211 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
    15 Days on yellowkey

    $1,648,000 | Condo | 2 beds | 2.0 baths

    Exceptional opportunity to own this beautifully reimagined first-floor residence at The Promenade on Longboat Key, where luxury coastal living meets sophisticated modern design. Completely gutted and renovated from top to bottom, this stunning condominium offers nearly 400 feet of private beach frontage and partial Gulf of Mexico views from almost every room. This spacious two-bedroom, two-bath split floor plan showcases a bright, open-concept design ideal for both entertaining and relaxed everyday living. The designer kitchen flows seamlessly into the expansive living and dining areas and features custom cabinetry, premium countertops with full-height backsplash, and top-tier appliances. A custom dry bar with built-in wine cooler and under-shelf lighting adds an elegant touch for effortless entertaining. Enjoy breathtaking northwest sunset views from the great room or unwind on the private balcony overlooking the Gulf. The luxurious primary suite offers direct balcony access, a large custom walk-in closet, and a spa-inspired en-suite bath complete with a soaking tub, rain shower system, and large-format designer tile creating a true retreat-like atmosphere. The generously sized guest bedroom provides comfort and flexibility for visitors. Every inch of this residence has been thoughtfully curated with exceptional craftsmanship and attention to detail, balancing modern sophistication with everyday comfort. The Promenade offers a true resort-style lifestyle with a 24-hour staffed gatehouse, concierge services, secure under-building assigned parking, heated Gulf-front pool and spa, expansive sundeck with gazebo and grilling area, four Har-Tru tennis courts, fitness center, craft room, and inviting social spaces. Private beach access lined with charming tiki huts completes this extraordinary Longboat Key experience. Rarely does a completely renovated residence of this caliber become available in one of Longboat Key’s most desirable Gulf-front communities. Experience the ultimate in beachfront living, where every day feels like a vacation.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
    Listing Agent: Leah George (941-780-0597)

  • 3606 FAIR OAKS PL, LONGBOAT KEY, FL - MLS# A4694394

    34228 - A4694394 - 3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228
    15 Days on yellowkey

    $4,999,000 | Single Family Home | 5 beds | 3.0 baths | 2 gar

    Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living spaces, and direct boating access, all within one of Longboat Key’s most sought-after neighborhoods. From the moment you arrive, the home’s meticulous maintenance and thoughtful renovations are immediately apparent. A roof just two years old, hurricane shutters on all windows and doors, and multiple updated mechanical systems provide exceptional value and confidence for years to come. Inside, the residence has been extensively renovated in 2026 with stunning new engineered wood flooring flowing throughout the home, creating a warm and welcoming coastal aesthetic. The spacious floor plan offers five generously sized bedrooms, ideal for accommodating family and guests while maintaining privacy and flexibility for today’s lifestyle needs. The heart of the home is the beautifully refreshed kitchen, complete with brand-new KitchenAid appliances installed in 2026, blending modern functionality with timeless design. Adjacent living and dining areas are filled with natural light and seamlessly connect to the outdoor entertaining spaces, creating an inviting atmosphere perfect for both everyday living and hosting gatherings. Every bathroom in the home was completely renovated in 2026 with stylish finishes and contemporary details that elevate the home’s overall elegance. Extensive system upgrades include three HVAC systems replaced in 2022, 2023, and 2026, along with a new hot water heater installed in 2026, ensuring maximum efficiency and comfort throughout the property. Outdoor living is equally impressive and designed to embrace the Florida waterfront lifestyle. The pool area underwent a significant transformation in 2025 with new pool decking, a resurfaced pool finish, updated waterline tile, and a new gas pool heater, creating a true private resort setting. In 2026, the addition of a fully equipped outdoor kitchen elevated the entertaining experience even further, offering the perfect backdrop for waterfront dining and sunset gatherings. Boating enthusiasts will appreciate the new 10,000-pound boat lift installed in 2025 along with a beautifully updated dock and deck, providing quick and convenient access to Sarasota Bay and the Gulf waters beyond. Combining luxury updates, exceptional outdoor amenities, and a premier location within the coveted Bay Isles community, with private beach club access, this extraordinary Longboat Key residence presents a rare opportunity to enjoy refined waterfront living with every major improvement already completed.

    Contact Yellowkey Agent

    Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
    Listing Agent: Renee Preininger (941-400-4235)

  • 2600 HARBOURSIDE DR #H-05, LONGBOAT KEY, FL - MLS# A4694769

    34228 - A4694769 - 2600 HARBOURSIDE DR #H-05, LONGBOAT KEY, FL 34228
    16 Days on yellowkey

    $300,000 | Dock-Rackominium

    The most convenient dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Nicely manicured lawn fronts the area at the slip. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much as a resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina 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. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!

    Contact Yellowkey Agent

    Listing is courtesy of: LBRE LLC (941-383-8383)
    Listing Agent: Jennifer Wilson (941-809-7592)

  • 1050 LONGBOAT CLUB RD #901, LONGBOAT KEY, FL - MLS# A4694717

    34228 - A4694717 - 1050 LONGBOAT CLUB RD #901, LONGBOAT KEY, FL 34228
    18 Days on yellowkey

    $1,400,000 | Condo | 2 beds | 2.0 baths | 1 car

    Welcome to your beachfront retreat in the sky. Perched on the 9th floor of the highly desirable Privateer North community on Longboat Key, this beautifully furnished 2-bedroom, 2-bath residence offers 1,409 square feet of coastal elegance and breathtaking panoramic Gulf views from every room. Wake each morning to the sound of waves and endless turquoise water, and end each day with spectacular sunsets from the comfort of your living room, primary suite, or private balcony. The light-filled open floor plan is designed to showcase the stunning waterfront setting, featuring spacious living and dining areas that flow seamlessly to the balcony overlooking the Gulf of Mexico. The well-appointed kitchen offers quartz countertops, modern appliances, ample cabinetry, and everything needed for effortless entertaining. The spacious primary suite features direct balcony access, a king-sized sleeping area, and an updated en-suite bath, while the guest bedroom provides generous accommodations for family and friends. Both bathrooms have been tastefully updated with elegant finishes and walk-in showers. Just steps from the building, residents enjoy a secluded stretch of pristine private beach complete with beach chairs and umbrellas, as well as a large heated beachfront pool and spa with unobstructed Gulf views. Privateer North offers an exceptional resort-style lifestyle with a newly renovated fitness center, pickleball courts, shuffleboard, outdoor grilling and picnic areas, covered parking, secure entry, on-site management, and beautifully maintained grounds. Ideally located on the southern end of Longboat Key, this residence is only minutes from the upscale shopping, dining, and entertainment of St. Armands Circle and a short drive to downtown Sarasota, renowned for its arts, culture, waterfront parks, and world-class restaurants. Offering unmatched views, exceptional amenities, and one of the area’s most sought-after beachfront locations, this is coastal living at its finest. ** Seller is a licensed Florida Real Estate Agent

    Contact Yellowkey Agent

    Listing is courtesy of: NINE LINE REALTY LLC (407-924-6353)
    Listing Agent: Jamie Tillman (417-224-1917)

  • 523 JUAN ANASCO DR, LONGBOAT KEY, FL - MLS# A4694601

    34228 - A4694601 - 523 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
    18 Days on yellowkey

    $1,895,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar

    This beautifully reimagined John Cannon home, in the tranquil north end of Longboat Key, blends luxury with island living. The custom, Spanish-style design offers four bedrooms and a complete top-to-bottom renovation. New hurricane-rated windows and doors ensure safety, and two brand-new air conditioning units—still under warranty—keep you cool. A tankless water heater, just three years old, provides endless hot water. In the garage, there’s a Mitsubishi AC dehumidifier, and the roof was replaced in 2026, giving you peace of mind. The kitchen is fully outfitted with Wolf and Sub-Zero appliances, and every bathroom has been completely remodeled. You’ll find extra storage in the garage, and deeded beach access means the sand is just moments away. Beyond the home, the location is unbeatable. You’re right across from the island’s pristine white sand beaches and close to golf, tennis, and the Longboat Key Club. You’re also a short drive from Anna Maria’s restaurants and bars. And if you love the outdoors, you can paddleboard, boat, kayak, and enjoy the island’s abundant wildlife—all right at your doorstep. This home offers both elegance and adventure, all in one stunning package.

    Contact Yellowkey Agent

    Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
    Listing Agent: Reid Murphy (941-232-3304)

  • 1045 GULF OF MEXICO DR #301, LONGBOAT KEY, FL - MLS# A4694202

    34228 - A4694202 - 1045 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
    18 Days on yellowkey

    $950,000 | Condo | 2 beds | 2.0 baths

    Coastal living at its finest and the perfect beach front retreat. This third floor corner residence is ready for your creative spirit. It offers views of the beach, the sparkling Gulf of Mexico, and breath taking sunsets year round. The new impact windows and sliding glass doors where installed in 2020 and the new HVAC system was replaced in March of 2026. This property is in very good condition and has been well maintained. Beachplace offers a Jr. Olympic sized swimming pool with swim lanes, a splash pool, hot tub, fitness center, grilling area, tennis, pickle ball, EV charger and a 24 hour guard gated entrance. All furnishings are included and this would make a great rental. New Roof in 2025

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
    Listing Agent: Maggie Hicks (941-321-1759)

  • 2675 GULF OF MEXICO DR #303, LONGBOAT KEY, FL - MLS# A4693865

    34228 - A4693865 - 2675 GULF OF MEXICO DR #303, LONGBOAT KEY, FL 34228
    18 Days on yellowkey

    $1,295,000 | Condo | 2 beds | 2.0 baths | 1 gar

    Under contract-accepting backup offers. Experience the ultimate in coastal luxury in this strikingly beautiful 1,900 sq. ft., furnished, direct Gulf-front residence, where breathtaking turquoise water panoramas and beach views surround you from every room. New A/C April 2026. Fridge & Hot water 2024. Thoughtfully designed with an open-concept kitchen, elegant plank wood-style porcelain flooring throughout, and an ideal split floor plan, this exceptional condominium offers two spacious en-suite bedrooms plus a versatile den or home office that easily functions as a third bedroom or study, comfortably accommodating up to 10 guests. Including 3 new sets of hurricane rated sliding doors at a cost of over $40,000. Secure key fab entry at the front Lobby or garage. Enjoy the convenience of an in-unit laundry room, generous walk-in closets, private under-building garage parking, bicycle storage, abundant guest parking, and resort-style amenities including a beachside pool, tennis and pickleball courts, and BBQ area. Perfectly positioned on Longboat Key, you can stroll next door to Maison Blanche for renowned Zagat and Golden Spoon award-winning dining, while Publix, CVS, Longboat Key Fitness personal trainers, and J.McLaughlin are all conveniently located just across the street.

    Contact Yellowkey Agent

    Listing is courtesy of: SARASOTA BEACH TO BAY INC (941-350-7104)
    Listing Agent: Debra Lichter (941-350-7104)

  • 1965 GULF OF MEXICO DR #G5-103, LONGBOAT KEY, FL - MLS# A4694695

    34228 - A4694695 - 1965 GULF OF MEXICO DR #G5-103, LONGBOAT KEY, FL 34228
    18 Days on yellowkey

    $649,000 | Condo | 2 beds | 2.5 baths

    Experience coastal living at its finest in this beautifully updated ground-floor residence at Seaplace on Longboat Key. This 2-bedroom, 2.5-bath condominium in the desirable G5 building offers northwest Gulf views and stunning sunset skies from the screened lanai, just steps from the beach. The bright, open-concept floor plan features a sleek modern kitchen with glossy cabinetry, quartz countertops, stainless steel appliances, and a spacious breakfast bar perfect for entertaining. Floor-to-ceiling mirrors enhance the natural light and create a spacious, contemporary feel throughout the living and dining areas. The primary suite offers a peaceful retreat with an updated en-suite bath, while the guest bedroom provides comfort and privacy for family and visitors. Hurricane-impact sliding glass doors and windows provide peace of mind and energy efficiency. Whether you are seeking a vacation getaway, seasonal retreat, investment property, or full-time residence, this move-in-ready condo checks every box. Seaplace is a gated Gulf-front community situated on 42 beautifully landscaped acres spanning from the Gulf to the Bay. Residents enjoy resort-style amenities including 24-hour guard-gated security, a newly remodeled clubhouse, two heated swimming pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, walking trails, fitness center, and private beach access with beach chairs and umbrellas provided. Conveniently located near the Longboat Key Club, St. Armands Circle, and Sarasota’s dining and cultural attractions. Schedule your private showing today and start enjoying the Longboat Key lifestyle!

    Contact Yellowkey Agent

    Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
    Listing Agent: Michael Renick Pllc (941-400-8735)

  • 1135 GULF OF MEXICO DR #505, LONGBOAT KEY, FL - MLS# A4694362

    34228 - A4694362 - 1135 GULF OF MEXICO DR #505, LONGBOAT KEY, FL 34228
    19 Days on yellowkey

    $1,175,000 Reduced | Condo | 2 beds | 2.0 baths | 1 gar

    DIRECT BEACH FRONT VIEWS AND FIFTH FLOOR EXTRORDINARY PANORAMA! Come visit this property soon, as it boasts Two Parking spots, one in garage, near the elevator and one outside near the front door. Reimagined kitchen with lots of cupboard space, all KITCHEN AID appliances, 2019 Air Handler, never rented and barely occupied. Furnished with exquisite taste and comfortable living space! Beachplace is unique from other communities due to its high rental appeal for returning families! Enjoy the great Olympic size pool located in the center of the complex, plus the oversized hot tub, workout facilities, tennis courts, pickle ball and more! Not to forget the covered baby pool for ages 3 and under! The highest and most sought after units are always BEACHFRONT, holding the best value!

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
    Listing Agent: James Weingart (440-623-9068)

  • 2600 HARBOURSIDE DR #H06, LONGBOAT KEY, FL - MLS# A4694669

    34228 - A4694669 - 2600 HARBOURSIDE DR #H06, LONGBOAT KEY, FL 34228
    19 Days on yellowkey

    $250,000 | Dock-Rackominium

    An exceptional 55-by-21-foot boat slip is ideally positioned in one of the most desirable locations within the Longboat Key Moorings Marina. Offering deep-water access with no bridges to Sarasota Bay and the Intracoastal Waterway, this premium slip provides effortless access to the Gulf and beyond. Longboat Key Moorings is a world-class marina offering individually owned slips, full-service concierge and maintenance services, and dockside electric, water and wireless internet. Residents enjoy the convenience of the adjacent Mediterranean-style village with waterfront dining, boutique shopping and nearby everyday conveniences, including Publix and CVS. A complimentary shuttle service to St. Armands Circle is also available. Membership to the Longboat Key Club is required, granting access to an exclusive private clubhouse featuring elegant gathering spaces, conference facilities, a television lounge and a variety of social events. Outdoor amenities include a private waterfront pool, grilling area, teak chaise lounges, dining tables and luxurious bathhouse facilities. Additional membership privileges include access to championship golf courses, tennis facilities, private beach access, a fitness center, a spa and wellness programs. Club members also enjoy reciprocity privileges with more than 700 yacht clubs nationwide. Experience luxury boating at one of Florida's premier marina destinations.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
    Listing Agent: Mike Warm, Llc (941-525-2740)

  • 3030 GRAND BAY BLVD #312, LONGBOAT KEY, FL - MLS# A4694200

    34228 - A4694200 - 3030 GRAND BAY BLVD #312, LONGBOAT KEY, FL 34228
    19 Days on yellowkey

    $995,000 | Condo | 3 beds | 3.5 baths | 2 gar

    Located in the Grand Bay community on Longboat Key, this spacious 3BR residence offers stunning views and desirable extras, including 2 conveniently located parking spaces. The pet friendly community allows up to 2 large dogs. The home features luxury vinyl flooring and neutral tones throughout, with floor-to-ceiling windows and plantation shutters that let in natural light. Elevated ceilings and accent lighting create an open, airy feel, while you enjoy views of Harbourside Golf Course, Sarasota Bay, and the downtown skyline from the expansive wraparound terrace that is perfect for entertaining or relaxing. The updated kitchen includes white cabinetry, Corian countertops, tile backsplash, stainless steel appliances, including a Sub-Zero refrigerator, and a central island. The living room/dining room offers ample space for a formal dining room table and large seating area. The primary suite is a private retreat, with access to the terrace and newly enhanced sightlines from the bedroom showcasing beautiful views of the Longboat Key Club golf course and Sarasota Bay. The primary bath features dual vanities, a walk-in shower, and a spa tub. The large custom closet is thoughtfully designed for ample storage. A full-size laundry room adds convenience. Grand Bay offers resort-style amenities including 24-hour gated security, a clubhouse with a library and game room, fitness center, 2 Har-Tru tennis courts, 2 heated pools, and a spa. Residents also enjoy deeded beach access through the Bay Isles Beach Club, just a short bike ride away. This private beach offers a peaceful, uncrowded environment, with a beachside pavilion, restrooms, and showers. Additionally, for those seeking more exclusive amenities, the optional Longboat Key Club provides access to luxury services, including golf, fine dining, a full-service spa, and fitness facilities.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
    Listing Agent: Bruce Myer (941-376-5311)

  • 2600 HARBOURSIDE DR #B-13, LONGBOAT KEY, FL - MLS# A4694623

    34228 - A4694623 - 2600 HARBOURSIDE DR #B-13, LONGBOAT KEY, FL 34228
    19 Days on yellowkey

    $500,000 | Dock-Rackominium

    A 100 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, extra wide finger pier, and deep water. Huge turning radius, with easy access slip with the views to match the superb amenity package, Slip B-13 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 100 x 28, and a usable beam of 25 feet and a long and extra wide finger pier. This location provides close proximity to the hospitality room and Pool. This is a Yacht Club slip. 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, 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. Buyer must join the Longboat Key Club on or before the closing date. Longest vessel this slip will accommodate is 95 feet LOA, with the beam depends on the make of the vessel. All vessels must be approved by the BOD prior to entering the Marina. A current photo and specs of the vessel must be submitted for review.

    Contact Yellowkey Agent

    Listing is courtesy of: LBRE LLC (941-383-8383)
    Listing Agent: Jennifer Wilson (941-809-7592)

  • 210 SANDS POINT RD #2101, LONGBOAT KEY, FL - MLS# A4694354

    34228 - A4694354 - 210 SANDS POINT RD #2101, LONGBOAT KEY, FL 34228
    19 Days on yellowkey

    $1,950,000 | Condo | 2 beds | 2.0 baths

    Rare 2BR First-Floor Lockout Unit | Resort at Longboat Key Club Experience the perfect blend of luxury vacationing and rental income with this rare, first-floor lockout suite overlooking the resort pool and just steps from the beach. • Versatile Rental Options: Lockout design allows you to rent as a full 2-bedroom suite or a 1-bedroom unit to maximize revenue. • Prime Location: First-floor convenience with an oversized deck, steps away from the beach, pool bar, and restaurants. • World-Class Amenities: Access to 45 holes of golf, 21 tennis courts, 5 restaurants, a luxury spa, fitness center, and a bayside marina. Perfect for families seeking a premium getaway with built-in investment potential.

    Contact Yellowkey Agent

    Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
    Listing Agent: Tom Cinquegrano (941-284-5049)

  • 240 SANDS POINT RD #4104, LONGBOAT KEY, FL - MLS# A4694224

    34228 - A4694224 - 240 SANDS POINT RD #4104, LONGBOAT KEY, FL 34228
    19 Days on yellowkey

    $1,025,000 | Condo | 1 beds | 1.0 baths

    Introducing a highly sought-after first-floor Junior Suite in Building 4, boasting stunning Gulf views and now available for purchase. This fully renovated unit is part of the hotel program, generating over $118K in gross income for 2025, with more than $79K already booked through April 2026, indicating the potential for even greater earnings this year. Enjoy an expanded deck alongside a covered terrace that offers direct beach access. Positioned at the northern end of the gulf side, Building 4 provides owners with a sense of privacy from pool activities while still being close to all amenities. As an owner, you gain access to the exclusive offerings of the 410-acre Longboat Key Club, including five fine dining options, 45 holes of championship golf, the award-winning Tennis Gardens, a spa and wellness center, a pristine white sand beach with umbrellas and waitstaff, and a full-service marina. The renovated rooms, main dining area, pool, and guest services enhance the experience at this award-winning property, recognized with accolades such as the AAA Four-Diamond Award and Condé Nast Travelers' Top Florida Resorts. Embrace the Longboat Life today!

    Contact Yellowkey Agent

    Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
    Listing Agent: Ian Addy, Pa (941-961-8850)

  • 3527 FAIR OAKS LN, LONGBOAT KEY, FL - MLS# A4694532

    34228 - A4694532 - 3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
    19 Days on yellowkey

    $2,550,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar

    Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent enhancements include a newer roof (2021), new panoramic pool cage with picture-frame screening (2025), new hurricane Armor Screen shutters protecting every opening (2025), and a custom two-person Pneumatic Vacuum elevator, along with numerous additional upgrades and improvements. Dramatic two-story windows fill the expansive great room and chef’s kitchen with natural light while showcasing breathtaking views of the sparkling pool, serene lake, lush landscaping, majestic oak trees, and the manicured fairway. Designed for both everyday living and entertaining, the gourmet kitchen is a culinary masterpiece, complete with a large gas range, dual ovens, solid wood cabinetry, abundant counter space, and a charming breakfast nook framed by bay windows overlooking the pool and golf course. The luxurious first-floor owner’s retreat offers Brazilian cherry wood flooring, vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bathroom. Two additional guest bedrooms on the main level are connected by a beautifully appointed Jack-and-Jill bathroom. Outdoor living is equally exceptional, with an oversized pool and spa set within a spacious private lanai designed for relaxation and entertaining while enjoying tranquil sunsets over the lake and golf course. Residents of Queens Harbour enjoy maintenance-free living, a private community pool, and exclusive access to the Bay Isles Beach Club with deeded Gulf beach access. Ideally located near the Longboat Key Club Harbourside golf course, tennis facilities, and the Moorings Yacht Club, this residence embodies the finest in Longboat Key luxury living.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
    Listing Agent: Miriam Pearson (941-726-4687)

  • 3806 GULF OF MEXICO DR #C209, LONGBOAT KEY, FL - MLS# A4693850

    34228 - A4693850 - 3806 GULF OF MEXICO DR #C209, LONGBOAT KEY, FL 34228
    20 Days on yellowkey

    $335,000 | Condo | 2 beds | 2.0 baths | 1 car

    Discover Your Slice of Paradise! This charming turnkey 2-bedroom, 2-bath condo is perfectly positioned between the Gulf of Mexico and Sarasota Bay, offering breathtaking sunrise and sunset views. Enjoy deeded beach access complete with lounge chairs, picnic tables, charcoal grills, and outdoor showers. On the bayside, recent upgrades include a new dock with first-come boat slips, community kayaks, an electric kayak launch, and a fishing pier with a cleaning station. Host a BBQ at the tiki hut or relax by the heated pool featuring gas grills, indoor restrooms, and an outdoor shower. The newly renovated clubhouse offers an upgraded fitness center, card room, large bar, full kitchen, and plenty of gathering space for entertaining.During season, this vibrant and friendly community comes alive with Wednesday night happy hours and festive celebrations including St. Patrick’s Day, Mardi Gras, Cinco de Mayo, and more.

    Contact Yellowkey Agent

    Listing is courtesy of: FLORIDA GALLERY REAL ESTATE (941-315-6678)
    Listing Agent: Kathleen Magnus (941-281-5539)

  • 6664 & 6660 & 6670 GULF OF MEXICO DR, LONGBOAT KEY, FL - MLS# A4694502

    34228 - A4694502 - 6664 & 6660 & 6670 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
    20 Days on yellowkey

    $18,500,000 | Single Family Home | 2 beds | 2.0 baths | 2 gar

    This house is a part of a 5.5 Property and will be sold together as one parcel. The house can be used as a guest house, caretaker home or removed for development.

    Contact Yellowkey Agent

    Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
    Listing Agent: Mark Huber (941-356-2435)

  • 2600 HARBOURSIDE DRIVE #H-04, LONGBOAT KEY, FL - MLS# A4694327

    34228 - A4694327 - 2600 HARBOURSIDE DRIVE #H-04, LONGBOAT KEY, FL 34228
    20 Days on yellowkey

    $275,000 | Dock-Rackominium

    A favorite dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Easy access on and off the water to this H-dock slip. Club membership is not 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, a Mediterranean style marina 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. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!

    Contact Yellowkey Agent

    Listing is courtesy of: LBRE LLC (941-383-8383)
    Listing Agent: Jennifer Wilson (941-809-7592)

  • 909 SPANISH DR N, LONGBOAT KEY, FL - MLS# A4694346

    34228 - A4694346 - 909 SPANISH DR N, LONGBOAT KEY, FL 34228
    20 Days on yellowkey

    $2,950 | Villa | 2 beds | 2.0 baths | 1 car

    One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. This beautifully updated/unfurnished two-bedroom, two-bath Spanish Main standalone villa with beach access is available for annual lease! The fully remodeled home features neutral tile plank flooring throughout, a spacious chef’s kitchen with 42-inch wood cabinets, quartz island that seats seven, slow-close drawers, and new appliances—all opening to a bright living area. The primary suite offers an en-suite bath with frameless glass shower and double sinks, plus a large walk-in closet. Step through new double doors to a generous screened lanai overlooking lush wetlands and Bay views, perfect for relaxing, dining, or using as a flexible third space, complete with retractable awning, brick paver patio, hurricane-rated windows and doors, motion lights, and electric blinds. In the vibrant 55+ Spanish Main Yacht Club community enjoy a pool, shuffleboard, private deeded beach access on Longboat Key, and easy boating, fishing, and cycling, all just minutes from St. Armands Circle, downtown Sarasota, dining, shopping, and the airport. Basic cable and water included. Move-in ready and waiting—call for details on this piece of paradise.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (239-262-4242)
    Listing Agent: Alex Lane (941-960-3080)

  • 791 BROADWAY ST, LONGBOAT KEY, FL - MLS# A4694059

    34228 - A4694059 - 791 BROADWAY ST, LONGBOAT KEY, FL 34228
    21 Days on yellowkey

    $1,625,000 | Single Family Home | 2 beds | 2.0 baths | 4 gar

    Welcome home to 791 Broadway, nestled in the heart of historic Longbeach Village on the North end of prestigious Longboat Key. This elevated island-style residence offers the perfect blend of coastal charm, comfort, and relaxed island living. Thoughtfully designed across multiple levels including a large 11x30 third floor FLEX SPACE that could easily be converted into a 3RD BEDROOM. This home captures beautiful morning sunrises, colorful sunsets, and stunning views of Sarasota Bay and the intracoastal waterway. From the moment you step inside, you are greeted by an abundance of natural light, soaring ceilings, plantation shutters, and inviting open spaces that are ideal for both everyday living and entertaining. The property offers wonderful flexibility, including an oversized garage with plenty of room for golf carts, kayaks, bicycles, beach gear, and more. The outdoor living areas are equally inviting, with several unique spaces to relax and enjoy the surroundings — from the covered front porch to the rear deck overlooking the water, along with the peaceful sound of multiple water features throughout the property. Recent updates add comfort and peace of mind, including new impact-resistant and energy-efficient windows, two AC units, updated flooring, and many additional improvements that make this home feel warm, welcoming, and move-in ready. Enjoy the charm and convenience of the Village, just a short stroll from community fishing piers, a boat launch, exceptional dining, and the white sandy beaches and turquoise waters of the Gulf of Mexico. This is a wonderful opportunity to experience the laid-back Longboat Key lifestyle in one of the island’s most beloved neighborhoods.

    Contact Yellowkey Agent

    Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
    Listing Agent: Matthew Voss (941-402-8799)

  • 840 BAYPORT WAY #840, LONGBOAT KEY, FL - MLS# A4694333

    34228 - A4694333 - 840 BAYPORT WAY #840, LONGBOAT KEY, FL 34228
    21 Days on yellowkey

    $4,200 | Condo | 2 beds | 2.0 baths | 1 car

    This stunningly appointed ground floor 2-bedroom 2 bath condo with lots of open living space is the ideal place to spend your summer vacation. Relax on screened lanai and enjoy the gentle breezes of this tropical oasis. Situated between Sarasota Bay and the Gulf of Mexico and surrounded by lush landscaping, you will truly find the private patio a great place to spend your afternoons. The beautiful upgrades to the kitchen and baths go hand in hand with the elegant decor of this property. Fully furnished and fully equipped and ready for your arrival, covered parking for one vehicle and guest parking is available as well. The clubhouse has a full kitchen facility and is large enough for meetings, private parties, and social functions, The exercise room is well equipped with machines and free weights. Classes in water Aerobics are held several times a week during the winter at a nominal cost, Available May to December at OFF Season rate of $4,200 per month plus 13% tourist tax. The property is a NO smoking/NO pet unit.

    Contact Yellowkey Agent

    Listing is courtesy of: REALTY SERVICES INC (941-954-4443)
    Listing Agent: Shirley Cuddy (941-321-1549)

  • 1211 GULF OF MEXICO DR #109, LONGBOAT KEY, FL - MLS# A4694082

    34228 - A4694082 - 1211 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228
    22 Days on yellowkey

    $1,000,000 | Condo | 2 beds | 2.0 baths | 1 gar

    One or more photo(s) has been virtually staged. Experience beachfront living at its finest at The Promenade on Longboat Key. This beautifully positioned residence showcases sweeping Gulf Views expansive terraces, and a seamless connection between indoor and outdoor living. Floor-to-ceiling windows fill the home with natural light while framing spectacular sunsets, pristine beaches and lush tropical surroundings. Thoughtfully designed with custom woodwork and an open , flowing layout, the residence offers exceptional comfort and flexibility. The kitchen enjoys water views and a unique connection to celebrated culinary icon, Marcella Hazan. Often called "the godmother of Italian cuisine', her award-winning documentary premiered at the Sarasota Film Festival! Residents enjoy resort-style amenities including concierge services, a staffed gatehouse, over-sized heated pool and spa, tennis courts, men's & women's fitness facilities, the Sunset and Sunrise club rooms, beachside gathering areas and direct access to the Gulf. Ideally located on the coveted south end of Longboat Key, The Promenade offers convenient access to St Armands Circle, downtown Sarasota , premier golf, dining, shopping, arts and cultural attractions. A rare opportunity to enjoy an exceptional beachfront lifestyle in one of Longboat's most sought after communities.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
    Listing Agent: Bill Blume (941-525-6257)

  • 1050 LONGBOAT CLUB RD #803, LONGBOAT KEY, FL - MLS# L4961980

    34228 - L4961980 - 1050 LONGBOAT CLUB RD #803, LONGBOAT KEY, FL 34228
    22 Days on yellowkey

    $6,000 | Condo | 2 beds | 2.0 baths | 1 car

    AVAILABLE 9/1/2026 to 12/31/2026. Oceanfront 2 bed/2 bath luxury condo on the 8th floor with beach and golf course views, two private balconies, and resort-style amenities just steps from the sand.The open-concept living and dining area features a custom bar and stylish decor, creating an inviting space to relax or entertain. A dedicated office makes working remotely effortless, while the sleek bar with wine refrigerator is perfect for evening cocktails at home. The fully equipped kitchen with built-in pantry offers everything you need, and the two serene bedrooms with King beds each enjoy convenient access to a full bath.This private, gated resort community offers a true coastal club experience. Host gatherings in the large community room, then move outdoors to the oceanfront pool, jacuzzi, fire pit, and grilling patio. Stay active with a swimming pool, workout room, pickleball, and shuffleboard courts on-site, then stroll directly onto the beach for a swim or sunset walk along the shoreline. 3 MONTH MINIMUM. Rental includes all furniture, appliances, dishes, cookware, and linens. Covered Parking spot #10 included with additional guest parking, seperate storage area for beach/pool items.

    Contact Yellowkey Agent

    Listing is courtesy of: XCELLENCE (866-595-6025)
    Listing Agent: Melissa Kontny (863-529-7465)

  • 3710 GULF OF MEXICO DR #G20, LONGBOAT KEY, FL - MLS# A4693944

    34228 - A4693944 - 3710 GULF OF MEXICO DR #G20, LONGBOAT KEY, FL 34228
    24 Days on yellowkey

    $349,900 | Manufactured Home | 2 beds | 2.0 baths

    WELCOME TO PARADISE! This unit epitomizes the perfect beach home. When you step through the front door, you will know that you have entered “House Beautiful”. The blend of colors and furnishings will make you feel that you are home. This home features a nice-sized living room, totally upgraded separate kitchen and dining room, two bathrooms and two bedrooms. This home has 1,052 sq. ft. of living area. This home is located just steps from Sarasota Bay. There are limited views of Sarasota Bay from the Living Room, Dining Room, Kitchen and the second bedroom. It has a new Mini Split A/C, and hot water heater. The roof is vinyl and has a brand new elastomeric coating with a 5 year warranty. This unit also has new skirting and new edging on the roof soffits. Gulfshore of Longboat Key is located on a perfect parcel of land. It has it all – private access to a pristine sand beach on the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large community pool, clubhouse with a commercial kitchen, a well-maintained and managed campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armand’s Circle. Gulfshore does not permit rentals or pets and it is a 55+ community. Please call now for an appointment to view your future home and relax in paradise.

    Contact Yellowkey Agent

    Listing is courtesy of: EDGEWATER REAL ESTATE, INC (941-778-8104)
    Listing Agent: Bill Shuttleworth (941-779-8877)

  • 2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL - MLS# A4693849

    34228 - A4693849 - 2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228
    25 Days on yellowkey

    $6,000 | Condo | 2 beds | 2.0 baths

    Now available FOR LEASE at The Islander Club on Longboat Key, this updated 2-bedroom, 2-bath residence offers exceptional value in a true beachfront community. Turnkey and move-in ready, the unit features an open layout with quality finishes, an updated kitchen with stainless steel appliances, wood flooring, refreshed bathrooms, and a spacious 38-foot terrace for outdoor living. The primary suite includes an ensuite bath and walk-in closet, while the guest bedroom offers comfort and privacy for visitors. Residents at THE ISLANDER on LONGBOAT KEY enjoy direct BEACHFRONT access along with resort-style amenities including a private beach, heated pool, fitness center, sauna, tennis, pickleball, and on-site management. Offered at $6,000/month May through December and $10,000/month January through April. AVAILABLE NOW for immediate occupancy. Contact listing agent for showing requests. OPEN FOR 2027 SEASON RESERVATIONS - 3 MONTH MINIMUM

    Contact Yellowkey Agent

    Listing is courtesy of: WAGNER REALTY (941-955-1500)
    Listing Agent: Richard Ivan (941-800-8891)

  • 3210 BAYOU SOUND, LONGBOAT KEY, FL - MLS# A4693846

    34228 - A4693846 - 3210 BAYOU SOUND, LONGBOAT KEY, FL 34228
    25 Days on yellowkey

    $7,500 | Single Family Home | 3 beds | 2.0 baths | 3 gar

    Experience the best of Longboat Key living in this beautifully updated Bay Isles pool home, offered turnkey furnished FOR LEASE and available for both short-term and long-term reservations. This furnished coastal retreat features an open floor plan with vaulted ceilings, 2 bedrooms plus an office, updated bathrooms, a spacious kitchen with premium appliances, and multiple indoor-outdoor living spaces designed for relaxed island living. Enjoy a private lap pool, screened upper-level deck, tropical landscaping, and a rare 3-car garage. Residents also have access to the exclusive BAY ISLE BEACH CLUB with private Gulf beach access. Publix, St. Armands Circle, and downtown Sarasota are all just minutes away. Available immediately for occupancy. Rates are $7,500/month May through December and $14,500/month January through April. 3 MONTH MINIMUM - Contact listing agent for availability and showing requests.

    Contact Yellowkey Agent

    Listing is courtesy of: WAGNER REALTY (941-955-1500)
    Listing Agent: Richard Ivan (941-800-8891)

  • 100 SANDS POINT RD #225, LONGBOAT KEY, FL - MLS# A4693834

    34228 - A4693834 - 100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228
    25 Days on yellowkey

    $899,000 | Condo | 2 beds | 2.0 baths | 1 car

    BACK ON THE MARKET with a New Price and Turn Key! Welcome to your slice of paradise, where coastal living reaches new heights of sophistication, and nestled inside the gates of the Longboat Key Club. This gorgeous 1492 sq. ft. water front residence underwent a total transformation in 2023, and the results are nothing short of spectacular. Step inside this bright second floor residence and discover a two bedroom and two baths, with a view that feels serene, luxurious, and unmistakably coastal. This condo comes with a view of the private marina tucked away in a quiet cove, where you can enjoy watching the dolphins at play. Towering palm trees frame the scene beautifully, with the curved waterfront drive adds a resort-style elegance to this one-of-a-kind property. This kitchen has a bright, modern, upscale feel with a clean coastal-inspired design. White shake-style cabinetry with sleek brushed nickel handles, extending all the way to the ceiling for extra storage. Exotic granite counters, matched with a sleek white Carrara marble back splash. Stainless steel appliances, and a deep undermount sink with a tall industrial-style spring faucet. The expansive great room steals the show, with a dramatic wall of windows, open concept and LVP flooring thru out. Both bathrooms feature quartz counter tops, tiled floors and walk in showers. HVAC 2020. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room with kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. With in walking distance to well renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.

    Contact Yellowkey Agent

    Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
    Listing Agent: Diane Smith (941-313-4957)

  • 2945 PYRULA DR, LONGBOAT KEY, FL - MLS# O6408404

    34228 - O6408404 - 2945 PYRULA DR, LONGBOAT KEY, FL 34228
    26 Days on yellowkey

    $3,125,000 | Single Family Home | 5 beds | 5.0 baths | 3 gar

    A contemporary masterpiece awaits Your going to love this house !, constructed in 2024 and completed in December of 2025 this newly built residence blends contemporary architecture with uncompromising craftsmanship. The craftsmanship, and finishing touches puts this property in a class by itself when making your buying comparisons. Worth repeating….Your going to love this house! Step into more than 3,800 square feet of modern design perfection ideally located in one of Longboat Keys most coveted neighborhoods. Just minutes on foot brings you to pristine beach access or a tee time at the prestigious Longboat Keys club. Seamless indoor- Outdoor living, a stunning floor to ceiling glass wall sets the tone from the moment you walk in revealing a private courtyard that feels like your own luxury resort, complete with an elegant pool, a relaxing spa, and a fully equipped outdoor kitchen and dining area. This harmonious flow creates an exceptional living experience where the outdoors becomes an extension of the home . Refined interiors inside , warm oak wood flooring runs throughout the home beautifully paired with stone accents , sleek cabinetry , and high end finishes. The chef designed kitchen is crafted for culinary excellence and features quartzite countertops prized for their durability, beauty, and unmistakably high end character. The primary suite is a serene retreat with glass walls overlooking the courtyard , a soaking tub , a separate shower, and generous storage. Spaces designed for comfort the home offers five bedrooms including An in law suite with a kitchenette, private laundry, spacious bedroom, and walk in shower. An additional bedroom on the main level with its own private balcony . Upstairs two guest suites connected by a bright relaxation area with courtyard views through the floor to ceiling glass. Striking modern architecture, the exterior showcases clean contemporary lines enhanced by rare hand selected stone and rich custom woodwork. Come visit this spectacular offering. ..

    Contact Yellowkey Agent

    Listing is courtesy of: PROPERTIO (888-817-3383)
    Listing Agent: Alin Zdroba (888-817-3383)

  • 4325 GULF OF MEXICO DR #103, LONGBOAT KEY, FL - MLS# A4693621

    34228 - A4693621 - 4325 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
    26 Days on yellowkey

    $1,100,000 | Condo | 2 beds | 2.0 baths | 1 car

    Experience coastal living in this two-bedroom, two-bath direct Gulf-front residence ideally on the main floor of a desirable mid-rise community on Longboat Key. Freshly painted and thoughtfully enhanced with quartz countertops in both the kitchen and laundry room, along with recently updated washer and dryer appliances, the residence also features crown molding, updated trim and plantation shutters throughout, as well as Gulf-side hurricane shutters. The covered Gulf-side lanai provides the perfect setting to relax and enjoy the coastal surroundings year-round. The primary bedroom offers a very large walk-in closet. This residence includes a designated covered parking space along with private exterior storage. Residents enjoy an impressive array of amenities, including a clubhouse with a sauna, a heated Gulf-front pool, an interlocking stone patio and barbecue, a covered area and direct beach access. Ideally in a sought-after mid-key location, the property is close to St. Armands Circle, with its renowned boutiques, dining and shopping, while downtown Sarasota is just over the bridge, offering arts, culture, dining and entertainment. Heading north, enjoy convenient access to Anna Maria Island, while heading south, you will find the many amenities of Longboat Key, including Publix, CVS, places of worship, banks, parks, town hall, Bayfront Park, public tennis courts, boat launches and more.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
    Listing Agent: Dennis Girard (941-809-0041)

  • 2410 HARBOURSIDE DR #131, LONGBOAT KEY, FL - MLS# A4693248

    34228 - A4693248 - 2410 HARBOURSIDE DR #131, LONGBOAT KEY, FL 34228
    26 Days on yellowkey

    $1,849,000 | Condo | 3 beds | 3.5 baths | 1 gar

    Dramatic Sarasota Bay views and a true “house-size” floor plan define this spacious 3BR/3.5BA residence in Marina Bay with 3,825 sq. ft. of living space. A private elevator lobby opens directly into the home, where generous living and dining areas, a formal foyer, powder room, separate family room, and two terraces create an easy flow for everyday living and entertaining. All three bedrooms feature en-suite baths and terrace access, while the primary suite enjoys panoramic bay and skyline views, separate bath areas, a large shared shower, jetted tub, and excellent closet space. The kitchen includes Sub-Zero refrigeration, solid-surface counters, breakfast area, and ample storage. A separate den with custom built-ins, bar area, and wine storage adds a comfortable office, media, or flex space. Marina Bay is a gated waterfront community in Bay Isles offering secured under-building parking, pool, spa, fitness center, tennis, pickle ball, storage, waterfront amenities, and beautifully maintained grounds. Residents also enjoy deeded access to the private Bay Isles Beach Club on the Gulf, with beach facilities, picnic areas, grills, and a relaxed residents-only setting. Optional membership to the Longboat Key Club is available separately, offering golf, tennis, dining, beach and pool amenities, spa, fitness, wellness programming, club events, and nearby marina access. Conveniently located close to Publix, CVS, restaurants, Longboat Key Club, St. Armands Circle, and downtown Sarasota.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
    Listing Agent: Bruce Myer (941-376-5311)

  • 1050 LONGBOAT CLUB RD #903, LONGBOAT KEY, FL - MLS# A4693486

    34228 - A4693486 - 1050 LONGBOAT CLUB RD #903, LONGBOAT KEY, FL 34228
    27 Days on yellowkey

    $995,000 | Condo | 2 beds | 2.0 baths | 1 car

    Set on the 9th floor at Privateer North, behind the gates of the Longboat Key Club, this beautifully renovated corner residence blends sweeping views, refined finishes and effortless coastal living. Offered TURNKEY FURNISHED, the 2-bedroom, 2-bath home looks out across the golf course, Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline, creating a view that shifts beautifully from morning light to evening sparkle. Inside, the renovation is immediately apparent. Clean neutral finishes, recessed lighting, crisp white trim and an open, comfortable floor plan keep the focus on the scenery beyond the glass. All glass is high-impact, hurricane-rated, and the residence also includes hurricane shutters for added peace of mind. The kitchen is designed for both everyday living and easy entertaining, with quartz countertops, custom cabinetry, high-end appliances, a wine refrigerator and detailed tilework. An inviting eat-in area frames bay views, bringing the water into daily life. The living and dining areas open to a terrace overlooking manicured grounds, the golf course and the bay beyond. Both bedroom suites are generously sized with walk-in closets, and the primary suite enjoys its own private terrace. The updated baths feature tasteful finishes, including a beautifully tiled walk-in shower in the primary bath. Privateer North offers a true beachfront lifestyle with a secure lobby, on-site management, heated pool and spa, fitness center, tennis and pickleball courts, social spaces and private beach access. For those seeking an even broader resort experience, optional membership at the Longboat Key Club offers access to 45 holes of golf, the Tennis Gardens with 20 Har-Tru courts, private dining, beach and pool facilities, spa, fitness, wellness programming, social events and marina amenities. Located on the sought-after south end of Longboat Key, the residence is just minutes from St. Armands Circle, downtown Sarasota, fine dining, shopping, arts venues and the area’s best coastal amenities.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
    Listing Agent: Bruce Myer (941-376-5311)

  • 3620 FAIR OAKS PL, LONGBOAT KEY, FL - MLS# A4693553

    34228 - A4693553 - 3620 FAIR OAKS PL, LONGBOAT KEY, FL 34228
    28 Days on yellowkey

    $3,150,000 | Single Family Home | 3 beds | 5.5 baths | 2 gar

    Under contract-accepting backup offers. Come for a visit and you will want to stay and make it yours! Strategically set back from the road, and appropriately positioned on this oversized lot, to allow for an abundance of private waterfront splendor. The expansive paver patio, with oversized pool, spa, outdoor kitchen, and fully equipped pool bath make this the prime setting for endless entertainment and fun with family and friends. Bay views expand over the mangroves to the rookeries and night lights of the Key as you take in the setting sun over Buttonwood Harbor. Get your fishing pole and binoculars ready because enjoyment is an every day event from your dock watching the beautiful Florida feather-life soar thru the skies or dropping a line to hook a surprise catch! Love the boating life? Great- your private dock awaits mooring of its next floating occupant! Upon entry you will be greeted with a customized deco- entry door offset with etched glass above. Inside this spacious home you will find three en-suite bedrooms with a highly possible 4th en-suite in the loft space. The interior space offers marble floors thru-out the entire residence, including the striking marble staircase, and ceilings that reach to great heights allowing for transom windows and a wall of glass to incorporate natural lighting and this amazing view. Like cocktails and eating? A home hi-lite is the wet bar which can serve multiple purposes- bar, buffet, or even a desk, centrally positioned between kitchen, living, dining and family room areas so that no one is too far from that beloved bartender or the delectable fare! Love art? These walls were meant for displaying the finest of your collection. This is a fabulous floorplan with a very separated bedroom layout providing plenty of space for all to spread out and make themselves comfortable. Located in Bay Isles, this home offers guarded, gated access and also deeded access to the Bay Isles Beach Club.

    Contact Yellowkey Agent

    Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
    Listing Agent: Cindy Schatzle (941-587-7556)

  • 3344 SABAL COVE LN, LONGBOAT KEY, FL - MLS# A4693445

    34228 - A4693445 - 3344 SABAL COVE LN, LONGBOAT KEY, FL 34228
    28 Days on yellowkey

    $1,699,000 | Single Family Home | 4 beds | 4.5 baths | 2 gar

    Behind the gates of Bay Isles in the private enclave of Sabal Cove, this spacious waterfront residence offers an exceptional opportunity to enjoy the desired Longboat Key lifestyle. Ideally positioned within proximity to the renowned amenities of the Longboat Key Club, with membership, residents can enjoy world-class tennis facilities, 45 holes of golf, a clubhouse, private dining venues and access to a marina. From the moment you enter the home, you are greeted by spectacular layered views of the water and golf course. Expansive glass doors draw your eye across the pool and spa, over the tranquil inland lagoon and beyond to the lush fairways of the golf course. Soaring ceilings and generously scaled rooms create an airy sense of openness throughout, while the flexible floor plan offers endless possibilities for customization and modern living. The eat-in kitchen is ideally situated to capture the stunning views and opens seamlessly to the living area, creating an inviting space for entertaining and everyday living. A formal dining space is also adjacent to the living room for special occasions. The first-floor primary suite is a peaceful retreat featuring dual walk-in closets, custom built-ins and large sliding glass doors framing serene water vistas. There is a dedicated office with a built-in desk and bookshelves. Also on the main level is an additional en-suite guest bedroom with a bath that conveniently serves as a pool bath. Upstairs, two additional en-suite bedrooms have privacy for family and guests, including one bedroom with a private lanai overlooking the water. There is new wood flooring on the first floor (living room, dining, entryway) and new wall-to-wall carpet upstairs. Additional features include a circular driveway and a two-car garage. This home offers outstanding space, views, and location with excellent bones and tremendous potential for updating and renovation to create a spectacular coastal estate that expresses your personal style. Residents of Sabal Cove enjoy deeded access to the gated Bay Isles Beach Club, featuring dedicated parking, beach chair storage, restrooms, picnic tables, outdoor grills, kitchen facilities and more than five acres of pristine Gulf-front beach on Longboat Key. Living here, you'll make memories that last a lifetime.

    Contact Yellowkey Agent

    Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
    Listing Agent: Judy Mitchell (941-275-6838)



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.