Longboat Key Listings

Some or all of the listings below are provided by the Longboat Key office.
$4,795,000 (USD)
Active

Nokomis Area Single Family Home

Active

2417 Casey Key Road Nokomis, FL 34275

2 Bed
2 Baths
1484 sqft
MLS# A4705426
Virtual Tour
A rare Gulf-to-Bay opportunity on Casey Key, where nearly an acre of land stretches from the turquoise waters of the Gulf of Mexico to the protected waters of the bay. With just over 100 feet of water frontage on both the Gulf and bay sides (and more than 400-feet of depth), this exceptional property presents an opportunity to create a custom waterfront retreat tailored entirely to your vision. Set along one of Sarasota’s most coveted barrier islands, the expansive homesite offers the extraordinary combination of a private Gulf beach, spectacular sunset views and direct boating access—all from one property.
On the beach side, step directly onto your own stretch of walkable sandy shoreline and enjoy unobstructed views across the Gulf of Mexico. Approximately 104 feet of Gulf frontage and a newer seawall, completed in 2004, establish an impressive setting for a future coastal residence designed around the water, sunsets and relaxed Casey Key lifestyle. Mature tropical landscaping and the parcel’s generous proportions create a wonderful sense of privacy rarely found along the coast.
Across the property, approximately 104 feet of bay frontage opens another dimension of waterfront living. The dock and boat lift, both added in 2022, provide convenient access to the Intracoastal Waterway and the exceptional boating, fishing and cruising opportunities of Southwest Florida. Spend the morning on the boat, return home by water and finish the day watching the sun disappear into the Gulf from your own backyard.
The nearly one-acre parcel provides remarkable flexibility for designing a custom residence that takes full advantage of its Gulf-to-Bay orientation, with the potential to capture water views in both directions. Imagine expansive indoor-outdoor living spaces, elevated terraces, a resort-style pool environment and private gathering areas framed by tropical landscaping—all designed specifically around this extraordinary coastal setting.
Casey Key remains one of the Gulf Coast’s most distinctive residential enclaves, prized for its natural beauty, privacy and laid-back character. Yet this secluded island setting is remarkably convenient to the restaurants, boutiques and waterfront charm of Nokomis and Venice, as well as nearby Nokomis Beach, the North Jetty, Venice Island and the Legacy Trail. Downtown Sarasota’s cultural attractions, dining and shopping are also within comfortable reach, while the Intracoastal and Gulf of Mexico are quite literally at your doorstep.
2417 Casey Key Road is more than a waterfront homesite—it is an opportunity to create a legacy property on one of Southwest Florida’s most treasured barrier islands, with the Gulf at one door and the bay at the other.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Roger Pettingell, Coldwell Banker Realty
$4,495,000 (USD)
Active

Bradenton Area Single Family Home

Active

332 Harbour Sound Court Bradenton, FL 34209

4 Bed
5 Baths
3384 sqft
MLS# A4686408
Virtual Tour
RARE LUXURY WATERFRONT OPPORTUNITY IN HARBOUR ISLE! Enjoy unobstructed, panoramic views of Anna Maria Island and Tampa Bay from this recently completed (2024) luxury waterfront home. Perfectly positioned within the master-planned community of Harbour Isle, this three-level coastal retreat blends modern elegance with breathtaking scenery—offering a front-row seat to spectacular sunsets and frequent dolphin sightings.
An elevated pool and outdoor kitchen overlook the tranquil waters of Anna Maria Sound, delivering an exceptional indoor-outdoor living experience. Every detail reflects superior craftsmanship, from architectural precision and custom millwork to designer finishes, premium appliances, and bespoke cabinetry.
A spacious multi-car garage offers room for three vehicles plus a golf cart, enhanced by a converted storage area to a third-car garage, overhead storage, air conditioning in both the garage and gym area, and a fenced and turfed space behind the garage with added access door (in process). The extended paver driveway accommodates up to three vehicles with ease.
The home is further upgraded with a whole-home generator, remote-controlled window shades, mounted TVs with in-wall electrical, and thoughtful modern conveniences throughout.
The main living area is easily accessed via a private elevator or a sunlit staircase with scenic views. The expansive great room and chef’s kitchen are designed to maximize sweeping water views, while the primary suite offers a serene retreat with a spa-inspired bath, soaking tub, and generous walk-in closet. Open-concept living and dining areas flow seamlessly to a large outdoor entertaining space overlooking the water.
The upper level includes a luxurious junior suite and two additional guest bedrooms, each with ensuite baths and abundant closet space. A versatile bonus area provides flexibility for a media room, office, or wellness space.
Located within the highly sought-after Harbour Isle community, residents enjoy exclusive access to a private clubhouse featuring a resort-style pool, state-of-the-art fitness center, Sky Bar & Restaurant, jacuzzi, private beach, and outdoor pavilion. Additional amenities include miles of walking and biking trails, kayak launches, multiple pools, and scenic gathering spaces.
Just minutes from Anna Maria Island’s renowned beaches and a short ride to Robinson Preserve’s nature trails, this home offers both tranquility and convenience. Nearby airports in Sarasota and Tampa/St. Petersburg provide easy access for travel. This is a rare opportunity to own a truly exceptional coastal residence in one of Florida’s most desirable waterfront settings.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Charles Buky, Coldwell Banker Realty
$4,350,000 (USD)
Active

Sarasota Area Condominium

Active

2052 Benjamin Franklin Drive D702 Sarasota, FL 34236

3 Bed
4 Baths
3654 sqft
MLS# A4672832
Located within Orchid Beach Club, the premier direct-beachfront building on the south end of Lido Beach, this expansive 3BR/3.5BA, 3,654-square-foot residence offers an exceptional blend of luxury, privacy, and coastal elegance. A private elevator lobby and double-door entry open to a light-filled floor plan designed for both everyday living and effortless entertaining. Main living areas feature soaring 10-foot ceilings, clean architectural lines, and generous wall space ideal for displaying artwork, all flowing seamlessly to the outdoors. The expansive beachfront terrace is a standout feature, showcasing unobstructed Gulf & sunset views and a built-in grill, perfect for al fresco dining, hosting guests, or just relaxing to the sound of the waves cascading on the shoreline. The gourmet kitchen is thoughtfully designed for culinary enthusiasts, offering a five-burner gas range, warming drawer, and spacious walk-in pantry. The primary suite serves as a peaceful retreat with a sitting area, wet bar, and sweeping panoramic views from Siesta Key to Longboat Key. Its spa-inspired bath includes dual vanities, a soaking tub with city views, an oversized walk-in shower with dual shower heads, and two private water closets. Two guest suites, each with en-suite baths, share access to a private terrace overlooking South Lido Park, with scenic vistas toward downtown Sarasota and St. Armands Circle, providing comfort, privacy, and memorable scenery. A rare and highly desirable offering, this residence includes a private two-car under-building garage just steps from the elevator with direct access to the unit, offering unmatched convenience, security, and ease of access rarely found in beachfront condominiums. Orchid Beach Club residents enjoy world-class amenities, including a 24-hour manned security gate, concierge services, and two elegant guest suites. Additional features include a heated beachfront pool and spa with private cabanas, a state-of-the-art fitness center with steam room and sauna, dedicated massage and treatment rooms, a social lounge with bar, fireside library, game room, and even an on-site dog run for that special pet. Just outside your door, you are moments from the sand and within walkable distance of South Lido Park and the Ted Sperling Nature Trail, while downtown Sarasota’s vibrant dining, arts, and culture are just around the bend. This exceptional residence offers a front-row Gulf Coast lifestyle, blending resort-style luxury with the tranquility of a private island enclave at one of Lido Beach’s most coveted addresses.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Ryan Ackerman, Coldwell Banker Realty
$4,245,000 (USD)
Pending

Sarasota Area Condominium

Pending

464 Golden Gate Point 702 Sarasota, FL 34236

3 Bed
5 Baths
3377 sqft
MLS# A4704663
Virtual Tour
FOREVER UNOBSTRUCTED BAY & DOWNTOWN SARASOTA VIEWS! Experience luxury waterfront living at La Bellasara, a gated boutique community on Golden Gate Point. This exceptional 7th-floor residence is furnished and move-in ready, offering 3 full bedrooms plus a den, 4.5 baths, a private 2-car garage and breathtaking panoramic views of Sarasota Bay & downtown City skyline from nearly every room. Thoughtfully reimagined architectural modifications and strategically reconfigured furnishings create a flowing, functional and beautifully balanced living environment. The elevator opens to a private lobby and double-door foyer entry. 3,200+ square feet of spacious living and entertaining areas with varying 9–11 ft. ceiling heights and custom built-ins. An updated gourmet kitchen features custom white cabinetry, top-tier appliances, a 6-burner gas range, center island, and walk-in pantry. The open layout effortlessly combines the kitchen, dining, breakfast and gathering areas, all oriented toward picturesque Bay and City views. The impressive 42-foot bayfront terrace, complete with a built-in gas grill, sink and food-prep area is ideal for casual outdoor celebrations. A separate library with custom built-in desk and bookcases provides flexible space for a home office or overflow guest accommodations. The primary suite features a separate entrance, two luxurious baths, one with a water view spa tub, dual walk-in closets, a morning coffee bar with refrigerator & sink and direct terrace access with Bay views. Two guest bedrooms with full en-suite baths, custom walk-in closets, and separate terraces, are thoughtfully positioned for privacy. Adding to its appeal, La Bellasara is undergoing an exciting renovation of the common areas - including the main lobby, fitness center, spa, conference room and social room, enhancing the building’s already exceptional lifestyle and creating a fresh, contemporary experience for residents. The private 2-car garage with storage space is conveniently located near the elevator. Concierge services are provided 7-days a week. Additional amenities include a heated pool and spa and a courtesy day dock. This pet-friendly downtown enclave on Golden Gate Point offers the feel of a private home with the convenience of luxury condominium living just moments from Sarasota’s dining, shopping, arts, and entertainment.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Ryan Ackerman, Coldwell Banker Realty
$4,165,000 (USD)
Active

Sarasota Area Condominium

Active

65 S Palm Avenue 702 Sarasota, FL 34236

3 Bed
4 Baths
3302 sqft
MLS# A4670076
Pre-Construction. To be built. Introducing the West Coast of Florida’s most distinctive and extraordinary new condominium offering. For the first time in over a century, the legendary Mira Mar is being reimagined. Originally established in 1922, this iconic South Palm Avenue landmark—home to Sarasota’s first hotel, graceful residences, and refined boutiques—was once the city’s most coveted address. Today, Seaward Development, Sarasota’s premier luxury developer, is breathing new life into this cherished property, blending its storied past with modern elegance to create a timeless residential masterpiece.
The all-new Mira Mar will showcase two sophisticated condominium towers that unite classic architecture with contemporary refinement. A limited collection of expansive residences—each designed to live like a private home—will offer breathtaking bayfront and city views, world-class design, and the ultimate in urban coastal living. Perfectly positioned along nearly 400 feet of South Palm Avenue frontage, residents will enjoy walkable access to Sarasota’s cultural destinations, fine dining, upscale shopping, and waterfront experiences—all just steps from their front door. Experience the perfect blend of space, style, and sophistication in this exceptional three-bedroom residence. The expansive primary suite features a luxurious en-suite bath with dual vanities, double water closets, and a generous walk-in shower with dual showerheads. A custom-designed walk-in closet offers elegant built-in cabinetry for refined organization. Two private terraces, including a remarkable 20' x 12' west-facing terrace, provide an inviting retreat for outdoor living and entertaining—all in the vibrant heart of downtown. Mira Mar residents will enjoy a collection of exceptional amenities designed for the most discerning lifestyles. These include 24-hour concierge, complimentary valet service, a resort-style pool and hot tub, and spa-inspired locker rooms featuring steam, sauna, and a therapy pool. The Sports Lounge offers a golf simulator and putting green, while the Garden Room and Terrace provide serene spaces for relaxation and social gatherings. Crowning it all is the exclusive Sky Speakeasy Lounge—a resident-only retreat located on the Penthouse level with captivating bay and sunset views, perfect for unwinding or entertaining in style.
A true expression of coastal luxury and downtown sophistication, Mira Mar represents a once-in-a-lifetime opportunity to live in a reimagined piece of Sarasota history—that began in 1922 where timeless architecture, impeccable craftsmanship, and an unmatched Palm Avenue location create the city’s most distinguished new address for a select few.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Nicholle McKiernan, Coldwell Banker Realty
$4,100,000 (USD)
Active

Sarasota Area Single Family Home

Active

1829 Bougainvillea Street Sarasota, FL 34239

4 Bed
4 Baths
4857 sqft
MLS# A4695800
Virtual Tour
Experience the timeless charm and distinctive elegance of this West of Trail luxury cottage, with modern finishes that remain true to its original allure, at 1829 Bougainvillea Street. Occupying three lots, it is nestled gracefully in Sarasota's most cherished neighborhood. Set on a tranquil, tree-lined avenue, moments from vibrant Southside Village, Sarasota Memorial Hospital, and the renowned sands of Siesta Key, this thoughtfully enhanced residence exudes a rare character and allure that newer homes simply cannot replicate.

From the moment you step inside, you're captivated by a refined blend of historic charm and contemporary luxury. Rich hardwood flooring, detailed crown moldings, and designer lighting create a warm and refined ambiance throughout the spacious, open-concept layout. Anchoring this home is a beautifully reimagined gourmet chef's kitchen, showcasing high-end stainless steel appliances, luminous granite countertops, bespoke cabinetry, and an expansive island—ideally suited for gatherings both grand and intimate. The luxurious master suite is a serene retreat, illuminated by abundant natural light and offering generous closet space alongside a spa-inspired ensuite with a sumptuous walk-in shower and dual vanities. Additional bedrooms and versatile living areas effortlessly accommodate family, guests, or a tailored home office. Unique to this remarkable residence is the thoughtfully designed separate living quarters, complete with a private entrance, an inviting bedroom, a fully equipped kitchen, and a full bathroom. Ideal for hosting guests, housing extended family, or offering privacy to long-term visitors, these quarters are unique.

Outside, the magic only continues—enchanting gardens burst with colorful bougainvillea, and mature greenery surrounds an inviting patio that effortlessly extends the living space outdoors, perfect for sunlit gatherings or quiet moments beneath Sarasota's famous skies. With meticulous care and modern upgrades, including a newer roof, advanced HVAC systems with two newly installed air conditioning units, recently replaced front-facing windows, and fully updated plumbing and electrical infrastructure, this home blends historic character with contemporary convenience, ensuring comfort, efficiency, and peace of mind.

1829 Bougainvillea Street represents more than just a renowned address; it offers a rare opportunity to own a property rich in Sarasota history and charm, distinctively set apart from uniformity and infused with authentic character.

Welcome home to an extraordinary residence awaiting your personal story. Its roots run deep into our community. The prior owners have all remained friends to this day, and the resurgence of the modern cottage is now at the forefront of interior design and architecture. This property embodies that trend in a way no other home can. A true one-of-a-kind that will never be replicated.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Ryan Skrzypkowski, Coldwell Banker Realty
$3,999,990 (USD)
Active

Longboat Key Area Single Family Home

Active

560 Chipping Lane Longboat Key, FL 34228

5 Bed
5 Baths
4315 sqft
MLS# A4702902
Virtual Tour
Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible living spaces and deeded beach access create a home designed for the Florida lifestyle. From the moment you enter, the water takes center stage and you know you're home. Generous living and dining spaces give the interior a sophisticated yet relaxed coastal feel. Inside, enjoy the high ceilings, Italian tile floors and a fireplace - and be transported through the wall of windows to blue waters of your pool and dock. The beautifully appointed kitchen is designed for both entertaining and everyday living with Sub-Zero French-door refrigeration and Wolf double ovens and cooktop, Asko dishwasher, new quartz countertops and a floating island with seating. Separate dining areas provide plenty of room for everything from casual mornings to entertaining a crowd. The primary suite offers a private retreat with a balcony and long-range water views - complete with a spacious bath featuring dual sinks and a walk-in shower. Additional oversized suites both upstairs and downstairs offer flexibility for a study or gym. Even more unique is the home's ability to accommodate extended family and guests. A separate entrance opens to its own living area and full bath, while upstairs are two additional bedrooms, a full bath and private sauna—creating a wonderfully versatile space for guests, multigenerational living or extended stays. Outside is where this property truly distinguishes itself. A generous pavered waterfront deck surrounds the Pebble-finish pool and spa, creating multiple areas for lounging, dining and entertaining. The fenced backyard leads to an impressive boating setup with two boat lifts—approximately 24,000 lbs. and 20,000 lbs.— newer seawall and composite dock plus a fish-cleaning station - making it exceptionally well equipped for the boating enthusiast. You're only four homes from the open waters of Sarasota Bay - providing immediate water access and minutes to the open Gulf. And if beach is more your style - enjoy the neighborhood's deeded access to the Gulf of Mexico- right across the street! Significant improvements add another level of value and peace of mind - including a newer roof (2020), all impact windows and doors, updated seawall and dock infrastructure (including plumbing and electrical service to the dock), extensive paver patio, pool resurfacing, interior and exterior painting, tankless hot water heater, landscaping and gas service ready to go for the next owner. And there's room for the toys with a two-car garage with workshop area and storage. You're only five minutes to vibrant St. Armand's Circle for shopping and dining - and a short drive to downtown Sarasota's cultural and entertainment venues. A special home to enjoy everything that makes Longboat Key living so special.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Monica Verinder, Coldwell Banker Realty
$3,995,000 (USD)
Active

Longboat Key Area Land

Active

1600 Harbor Sound Drive Longboat Key, FL 34228

Bed
0 Baths
sqft
MLS# A4698387
Virtual Tour
Discover the rare opportunity to create a legacy waterfront estate in the prestigious Harbor Section of Bay Isles, one of Longboat Key's most coveted boating communities. Tucked behind double gated, guard-secured entry, this exceptional 0.41-acre homesite boasts an impressive 135 feet of deep-water frontage, offering effortless access to Sarasota Bay and the Gulf of Mexico. Designed for those who embrace the waterfront lifestyle, the expansive canal frontage provides possibilities for multiple vessels and seamless days on the water. As a Bay Isles resident, you'll also enjoy deeded private access to the Bay Isles Beach Club, where miles of pristine Gulf beaches await. Perfectly positioned directly across from the world-renowned St. Regis Longboat Key Resort, this premier location places luxury amenities at your doorstep while maintaining the privacy and exclusivity of a gated waterfront enclave. Championship golf, marinas, waterfront dining, boutique shopping at St. Armands Circle, and the arts, culture, and fine dining of downtown Sarasota are all just minutes away. Whether you envision a contemporary coastal masterpiece or a timeless waterfront retreat, this remarkable homesite offers the ideal canvas to build the custom residence you've always imagined in one of Southwest Florida's most distinguished waterfront communities. Architectural plans are available upon request, with engineering complete. Capitalize on the extensive development work already completed, saving valuable time and expense while accelerating the path toward permitting and construction. An existing residence is situated on the property; however, the property is being marketed for its exceptional homesite and development potential.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Rinat Sikdar, Coldwell Banker Realty
$3,950,000 (USD)
Active

Sarasota Area Single Family Home

Active

541 S Washington Drive Sarasota, FL 34236

4 Bed
5 Baths
3395 sqft
MLS# A4695620
Virtual Tour
For Those Who See Home as an Expression of Art. 541 S Washington offers a rare blend of architectural character, quality craftsmanship, and waterfront living. Beautifully renovated to reflect the enduring principles of Mid-Century Modern design, where clean lines, natural light, and a connection to the outdoors shape the living experience. Set on 75 feet of canal frontage along prestigious South Washington Drive, just moments from St. Armands Circle, Lido Beach, and downtown Sarasota. From the moment you enter, expansive folding glass doors frame the water beyond. A striking gas fireplace anchors the main living spaces, while thoughtfully proportioned rooms balance openness with comfort. Offering four bedrooms, four-and-a-half baths, and a flexible bonus space, the 3,395-square-foot floor plan was designed for easy every day living. At the center of the home, a custom Poliform kitchen with premium Miele appliances combines clean design with exceptional functionality. The primary suite serves as a private retreat, complete with a spa-inspired bath and outdoor shower. Throughout the residence, the current owners have also enhanced the property with Control4 home automation, security system, new HVAC system, instant-on hot water heaters, whole-home water treatment, Icynene insulation, and a reinforced roof with tiedowns. Outside, curated tropical landscaping creates privacy around the heated saltwater pool. Multiple outdoor living spaces, including an expansive balcony and rooftop deck, provide beautiful settings for sunset views, while a private kayak launch offers direct access to Sarasota's waterways. A distinctive waterfront residence in one of Sarasota's most sought-after island neighborhoods, inspired by timeless design and a connection to the water. Inquire with the listing agents for a complete list of updates and to schedule your private showing.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Keith Kleppinger, Coldwell Banker Realty