Longboat Key Listings

Some or all of the listings below are provided by the Longboat Key office.
$1,095,000 (USD)
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Longboat Key Area Condominium

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1000 Longboat Club Road 402 Longboat Key, FL 34228

2 Bed
2 Baths
1290 sqft
MLS# A4670053
Virtual Tour
Coastal Elegance at Privateer South, Longboat Key!
Set directly along the Gulf of Mexico, this beautifully renovated two-bedroom residence at Privateer South offers effortless beachfront living within the gates of the prestigious Longboat Key Club. Move-in ready, every detail of this turnkey fourth-floor getaway speaks to comfort, style, and sophistication, framed by sweeping Gulf views and warm coastal light.
Porcelain tile floors extend throughout, creating a seamless flow from room to room, while all-impact glass sliders and windows frame tranquil vistas and ensure peace of mind. The open-concept great room is spacious yet inviting, with defined living and dining areas that connect effortlessly to one of two private terraces—perfect for morning coffee or evening sunsets over the water.
The modern kitchen features solid wood, shaker style cabinetry (unified throughout the home), sleek granite countertops, stainless-steel appliances, wine refrigerator, and breakfast bar seating, offering the perfect blend of beauty and function. Built-in shelving adds both storage and architectural character, while subtle lighting and window treatments complete the refined aesthetic.
The primary suite serves as a private retreat with direct terrace access, a generous wall-to-wall custom-built closet, and a revamped en-suite bathroom featuring dual vanities, granite counters, and a spacious shower with multiple heads. The second bedroom is thoughtfully designed to function as a stylish office or guest suite, complete with a walk-in closet and custom Murphy bed concealed behind clean cabinetry—ideal for flexible use of space. A second full bath with tub/shower combination is equally well-appointed.
Two terraces—overlooking the shimmering Gulf and eastern sunrise views—extend the living experience outdoors. The residence also includes an assigned covered parking space, the convenience of interior laundry, and abundant storage throughout.
Privateer South is one of Longboat Key’s premier beachfront communities, offering resort-style amenities in a serene and secure setting. Residents enjoy a Gulf-front heated pool and spa, tennis and pickleball courts, fitness center, and clubhouse, all surrounded by lush tropical landscaping with direct access to one of Florida’s most pristine stretches of sand. Association fees include cable, water, waste collection, grounds care, and 24-hour gated security for a truly maintenance-free lifestyle.
Perfectly positioned within the Longboat Key Club gates, the location allows members to enjoy world-class golf, a full-service marina, and exceptional dining just moments away (membership options available separately). A short drive brings you to St. Armands Circle for boutique shopping and fine restaurants, or over the bridge to downtown Sarasota, where theater, art, and culture thrive.
Offering a rare combination of coastal tranquility, thoughtful design, and resort-style living, Privateer South #402 captures the best of Gulf-front Sarasota living—an inspired residence where every day feels like a retreat.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$1,095,000 (USD)
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Longboat Key Area Condominium

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5055 Gulf Of Mexico Drive 331 Longboat Key, FL 34228

2 Bed
2 Baths
1484 sqft
MLS# A4670624
Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Tennis, offering expansive Gulf views and one of the largest floor plans in the community. This exceptional 2-bedroom plus 3rd bedroom/study layout perfectly blends elegance, comfort, and functionality, ideal for full-time living or as a refined vacation escape. With 750 feet of pristine Gulf frontage, this home immerses you in the beauty and serenity of coastal living. Beautiful engineered white oak wood floors flow throughout the open, sun-filled living space, which seamlessly extends to your private balcony’s, the perfect spot to enjoy the tranquil sound of the waves and stunning sunsets. The updated kitchen features stone countertops, white cabinetry, and has been opened up to create a larger, more connected floor plan ideal for entertaining. The primary suite is a private sanctuary, boasting a remodeled marble bath with high-end fixtures and a spa-like ambiance. The guest suite provides equal comfort and privacy, featuring a beautifully appointed travertine-floored bathroom. A custom wall of California closets offers exceptional storage and style. The Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, eight professional har-tru tennis courts, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat is a pet-friendly community allowing up to two pets with fees that include exterior maintenance and insurance, cable, water, sewer and trash. Perfect as a full-time residence or an income-producing rental, with one-month minimum leases permitted up to 12 times per year. Only a short drive to many fine restaurants, boutiques, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Schedule your showing today and make resort style living a reality.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Ryan Heers
$1,090,000 (USD)
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Sarasota Area Condominium

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101 Benjamin Franklin Drive 63 Sarasota, FL 34236

2 Bed
2 Baths
1275 sqft
MLS# A4668335
Virtual Tour
Experience stunning, unobstructed views of the Gulf from this 2-bedroom, 2-bath condo located directly on the beach in highly sought-after Lido Key. Just a short walk to world-famous St. Armands Circle, you'll enjoy easy access to upscale shopping, dining, and entertainment—all while living steps from the sand and surf. This fully furnished, move-in-ready residence offers 1,275 sq ft of light-filled living space, with breathtaking water views from every room. Neutral tile flooring flows throughout, creating a clean, coastal feel. Step out onto your private 240 sq ft balcony to soak in nightly sunsets and the soothing sound of waves—there’s plenty of room for dining or lounging in style. Inside, enjoy the convenience of electric shades, ample closet space, and a separate storage locker located right in front of your assigned parking space. Hurricane shutters provide added peace of mind, and yes—your small pet (up to 25 lbs) is welcome too! The building has undergone significant renovations including updates to the lobby, community spaces, kitchen, library, gym, bathrooms, plumbing re-lining, and resurfaced heated pool. On-site maintenance management adds another layer of ease to your beachside lifestyle—and best of all, the building is fully funded. Live just minutes from Lido Beach's Tiki Bar and Pavilion, or explore the nearby nature preserve with kayaking, paddleboarding, and fishing. Downtown Sarasota—with its vibrant arts scene, fine dining, and cultural venues—is just a short drive away via the Ringling Bridge. This is more than a condo—it’s your gateway to the ultimate coastal lifestyle. Schedule your showing today and own a front-row seat to the Gulf of Mexico.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Nathalie Nolander
$1,074,000 (USD)
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Longboat Key Area Condominium

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5311 Gulf Of Mexico Drive 3 Longboat Key, FL 34228

2 Bed
2 Baths
1028 sqft
MLS# A4635657
Virtual Tour
Turnkey furnished and ready to enjoy or rent, this charming beachfront retreat on Longboat Key offers the perfect blend of coastal living and investment potential. Situated directly on the pristine shores of the Gulf of Mexico, this two-bedroom residence grosses an average of six figures in annual rental income, making it an exceptional opportunity for personal enjoyment or weekly rentals. Set within Beach Castle Resort, this first-floor, direct Gulf-front property boasts breathtaking water views and effortless beach access just steps from the outdoor entertaining spaces. Inside, the light-filled interior features oversized tile flooring, updated windows and sliders (2009), and a granite kitchen with modern cabinetry, appliances, and upgraded plumbing and electrical systems (2006). The open-concept layout seamlessly connects the kitchen, living, and dining areas, with sliders leading to an inviting patio and a screened-in space ideal for relaxation. The two-bedroom split layout ensures privacy for guests. The primary suite enjoys private patio access and serene Gulf views, creating a peaceful retreat for owners and visitors alike. Beach Castle Resort is one of the rare Longboat Key communities offering flexible daily, weekly, or monthly rental programs. Residents and guests appreciate the beach-to-bay amenities, including deeded beach access, barbecue grilling areas, a sundeck with a heated swimming pool and spa, a fishing pier, and a day dock for boating enthusiasts (no overnight docking, first-come basis). The north end of Longboat Key offers a relaxed, tropical lifestyle. Bayfront Park and Cedars Tennis Resort are minutes away, while the southern end of the island brings the liveliness of the Longboat Key Club, fine dining, boutique shopping at St. Armands Circle, and the cultural attractions of downtown Sarasota. This beachfront retreat is an ideal escape, combining Gulf-front tranquility with exceptional rental income potential.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$999,999 (USD)
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Sarasota Area Single Family Home

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2518 Dick Wilson Drive Sarasota, FL 34240

3 Bed
3 Baths
3023 sqft
MLS# A4672995
Virtual Tour
EMBRACE THE 3 L's IN LAUREL OAK: Location, Layout and Light! With its thoughtful floorplan, open-concept interiors, and seamless indoor-outdoor flow, this 3 bedroom, 3 bathroom home effortlessly combines luxury, function, and privacy — all within a captivating courtyard setting surrounded by over 3000 sf of living space. It is perfect for those who love to entertain thanks to its triple split floorplan and large common spaces. The moment you enter, you’re greeted by the serene centerpiece of the home — a sparkling heated pool and spa, outdoor kitchen with vented gas grill, and shaded al fresco dining space. The main house showcases soaring ceilings with crown molding, while French doors and transom windows flood the interiors with natural light. A sunroom in the back functions as a perfect playroom for little ones, or as an inspiring office, art studio, or library. The guest suite is thoughtfully designed with a custom Murphy bed and library shelves, and is ideal offering the independence and comfort of a true guest house within the property’s secluded courtyard embrace. ** The property offers peace of mind, inside and out, as it has a brand new AC and water heaters, was recently re-plumbed, and has a 2017 barrel tile roof. It has been beautifully maintained, with a recently updated pool heater and pump and a brand new well for irrigation. The oversized two-car garage with golf cart space includes a large air-conditioned storage room, is EV charging ready with a 40amp wall outlet, and there is additional parking space for all the guests who will be clamoring to come visit! ** Enjoy care-free living as this enclave of Laurel Oak includes lawn maintenance in your HOA fees. Laurel Oak Estates offers a lifestyle of distinction, featuring a 24 hour guarded gate and stunning manicured grounds. Membership to the club is optional, and has its privileges: 36 holes of championship golf, 12 tennis courts, 6 pickleball courts, a clubhouse that offers dining and social events, and an inviting heated and cooled junior Olympic pool. Live the Florida lifestyle you’ve been dreaming of, in the home and community that will make you feel like you’re on a permanent vacation!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Alison Stottlemyer
$999,000 (USD)
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Sarasota Area Single Family Home

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7031 Scrub Jay Drive Sarasota, FL 34241

4 Bed
3 Baths
3586 sqft
MLS# A4668056
Virtual Tour
Serenity, sophistication, and sweeping lakefront views converge in this exceptional estate, located within the prestigious gated community of Red Hawk Reserve. Set on a premium homesite and thoughtfully crafted for both elegant living and effortless entertaining, this 3,586 sq. ft. residence offers four bedrooms, three bathrooms, a dedicated office, a flexible studio or fifth bedroom, and an expansive 400+ sq. ft. bonus room. From the moment you step inside, you're welcomed by soaring ceilings, abundant natural light, and timeless architectural details that create a sense of openness and grandeur. At the heart of the home lies a gourmet kitchen, beautifully appointed with designer cabinetry, a custom wood range hood, granite countertops, under-cabinet lighting, a center island with breakfast bar, and high-end stainless steel appliances. Adjacent to the kitchen, a cozy dinette framed by a sweeping aquarium window offers the perfect setting to enjoy your morning coffee while overlooking the pool and tranquil lake. The primary suite is a private retreat, complete with serene views, dual custom walk-in closets with upgraded built-ins, and a spa-inspired en-suite bath featuring a Roman shower, soaking tub, and separate vanities. Step outside to your resort-style oasis—an expansive wrap-around lanai with brick pavers, a heated pool and spa, and lush tropical landscaping, all set against the backdrop of shimmering lake views. An oversized three-car garage offers generous built-in storage and overhead racks. At the same time, the community provides added peace of mind with a virtual guard gate, high-resolution security, and reclaimed water irrigation. Located within an A-rated school district and just minutes from the world-renowned Siesta Key Beach, this remarkable residence embodies the essence of Florida luxury living.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Ryan Skrzypkowski
$995,000 (USD)
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Longboat Key Area Condominium

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5311 Gulf Of Mexico Drive 3 Longboat Key, FL 34228

2 Bed
2 Baths
1028 sqft
MLS# A4672601
Virtual Tour
Turnkey furnished and positioned directly on the sandy shores of the Gulf of Mexico, this first-floor, direct Gulf-front residence at Beach Castle Resort offers an exceptional blend of beachfront living and proven rental performance. Averaging six figures in annual gross income, this two-bedroom retreat is ideal for personal enjoyment, weekly rentals, or a combination of both—making it one of Longboat Key’s strongest investment opportunities.
The light-filled interior features oversized tile flooring, updated windows and sliders (2009), and a well-appointed kitchen with granite countertops, contemporary cabinetry, modern appliances, and plumbing and electrical upgrades completed in 2006. Designed for effortless coastal living, the open layout seamlessly connects the kitchen, dining, and living areas. Floor-to-ceiling sliders lead to a private patio and screened-in lanai, both just steps from the beach, allowing indoor and outdoor spaces to flow together naturally.
The split-bedroom plan enhances privacy for owners and guests. The primary suite enjoys beautiful Gulf views, private patio access, and a peaceful setting perfect for morning coffee or sunset unwinding. A comfortable second bedroom and full bath complete the guest wing.
Beach Castle Resort is one of the few communities on Longboat Key offering daily, weekly, or monthly rental flexibility, giving owners the freedom to maximize both personal use and rental income. The community’s beach-to-bay amenities include deeded beach access, a sundeck with heated swimming pool and spa, barbecue grilling areas, a fishing pier, and a day dock for boating enthusiasts (first-come basis, no overnight docking). Lush tropical landscaping and well-maintained grounds create a relaxing boutique-resort environment.
Perfectly located on the north end of Longboat Key, the property is minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic walking and biking routes. A short drive south leads to the Longboat Key Club, upscale dining, and the attractions of St. Armands Circle. Downtown Sarasota—home to world-class theater, museums, botanical gardens, professional events, and waterfront parks—is just across the bridge.
With direct Gulf-front views, strong rental history, and an unbeatable location, this Beach Castle residence offers the best of Longboat Key’s coastal lifestyle—whether you’re seeking an investment, a getaway, or both.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$985,000 (USD)
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Sarasota Area Single Family Home

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3795 Eagle Hammock Drive Sarasota, FL 34240

3 Bed
3 Baths
2767 sqft
MLS# A4671537
Virtual Tour
This exquisite custom home, crafted by Tivoli Homes and built in 2014, sits gracefully behind the gates of The Hammocks—a community known for its manicured landscaping, brick-paved driveways, timeless tile roofs, and generously sized homesites. This home has customized landscaping both in front and in the back garden area. Inside, thoughtful upgrades bring warmth and elegance to every corner. Crown molding highlights the formal spaces, while tray ceilings add depth and character to the master suite, living room, and dining room. The gourmet kitchen is a true centerpiece: granite counters, a center island, rich cabinetry with soft-close features, top-tier appliances, a gas cooktop with pot filler, and a custom hood and backsplash—all coming together to create a space that’s as functional as it is beautiful. The master suite offers peaceful views of the pool and the nature preserve beyond, giving the room a sense of quiet retreat. The en-suite bath features dual granite vanities with abundant storage, a separate garden tub, a walk-in shower, and two custom walk-in closets designed to keep everything effortlessly organized. A versatile Den/Library features rich wood-look luxury vinyl planking—an ideal spot for work, reading, or overflow guest space. Two other guest bedrooms have the same luxury vinyl planking and custom closets. Three sets of glass doors open to an outdoor living area designed for year-round enjoyment. The custom saltwater heated pool and spa include a swim shelf and an awning with lighting that elevates the entertainment area, giving ample shade when needed. The outdoor kitchen—with its built-in grill and bar—anchors the extended paver lanai, creating an inviting space for gatherings large or small. Exterior painted in 2024, and the crowning touch is the air-conditioned garage with custom cabinetry. All of this is just a short drive from UTC Mall, multiple golf courses, and the area’s renowned beaches, as well as Rothenbach Park—making The Hammocks a perfect blend of serenity and convenience. There are many upgrades the seller has made to this property, feature sheet is available.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Steve Abbe