Longboat Key Listings

Some or all of the listings below are provided by the Longboat Key office.
$975,000 (USD)
Active

Sarasota Area Single Family Home

Active

221 Island Circle Sarasota, FL 34242

3 Bed
2 Baths
1159 sqft
MLS# A4668472
Virtual Tour
Experience the best of island living in this beautifully maintained Turnkey FULLY FURNISHED, Key West-style home just moments from Siesta Key Public Beach and the vibrant Siesta Village. Offering 3 bedrooms, 2 bathrooms, and a 2-car garage with brand-new doors, this residence has been thoughtfully updated over the years with major recent improvements including a 2023 metal roof and all-new impact glass windows and doors for peace of mind. Head upstairs to the main living level where an open-concept layout welcomes you with luxury vinyl plank flooring, vaulted ceilings, and plantation shutters that fill the space with natural light. The kitchen features stainless steel appliances only a few years old, granite countertops, and a convenient connection to the dining area—ideal for hosting friends and family. Each bedroom showcases plantation shutters and crown molding for added charm. The primary suite is a true retreat, complete with a walk-in closet with built-in organization, an ensuite bathroom with a glass-enclosed shower tucked behind a stylish barn door, and direct access to the backyard deck through sliding glass doors. The two guest bedrooms share a tastefully updated full bathroom. Step outside to the elevated deck overlooking the private backyard, where a cozy fire pit area awaits in the corner—perfect for evening conversations and coastal breezes. An outdoor shower is the perfect spot to rinse off after a long day at the beach. Whether you’re seeking a full-time residence or the ideal vacation getaway, the flexibility of no HOA allows you to live as you please. Located just down the road from the powdery white sands of world-renowned Siesta Beach and only a half mile from the charming shops and restaurants of Siesta Village, this home delivers the quintessential Siesta Key lifestyle.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Kaisen Mitchell
$975,000 (USD)
Active

Sarasota Area Single Family Home

Active

795 Plymouth Street Sarasota, FL 34242

4 Bed
3 Baths
1967 sqft
MLS# A4661729
Virtual Tour
Welcome to your slice of paradise on Siesta Key. This beautifully updated 4-bedroom home offers the perfect blend of coastal charm and modern comfort, nestled on a peaceful, tree-lined street in one of the island’s most sought-after neighborhoods. Step inside to discover a bright, airy interior filled with natural light, where spacious living areas flow effortlessly into a large open-air pool, ideal for relaxing afternoons or entertaining under the sun. The heart of the home is designed for easy Florida living, with a thoughtful layout that invites connection and calm. The primary suite features a generous walk-in closet and a calming, private ambiance, perfect for unwinding after a day in the sun. Recent upgrades include a new roof installed in 2021 and a high-efficiency HVAC system from 2020, offering peace of mind and year-round comfort. Outside, the hardscaped, low-maintenance yard adds tropical appeal without the upkeep, while the paver driveway enhances curb appeal with a touch of elegance. Whether you're hosting poolside gatherings or enjoying quiet mornings with coffee and birdsong, this home delivers the kind of lifestyle that feels like vacation every day. And with Siesta Beach just minutes away, you’ll have world-class sand and surf practically at your doorstep. Move-in ready and lovingly maintained, this property is more than a home, it’s a serene escape in the heart of paradise. Did not flood during 2024 storms.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Courtney Church
$950,000 (USD)
Active

Sarasota Area Single Family Home

Active

5557 Long Shore Loop Sarasota, FL 34238

3 Bed
2 Baths
2298 sqft
MLS# A4674783
Virtual Tour
This Stunning Home and “Amenity Rich” Gated Community checks off every box!
** FORMER MODEL ** Stunning & Spacious 2,298 sf Pool/Spa Home Features: 3 Bedrooms, 2 Baths and a 2 Car Garage and is literally ACROSS THE STREET from PICKLEBALL, CLUBHOUSE, FITNESS CENTER, RESORT POOL/SPA, BOCCE BALL & TENNIS in the highly sought-after Gated Maintenance-Free community of Sunrise Preserve at Palmer Ranch. This former Model Home features Casual & Contemporary ELEGANCE combined w/ endless Upgrades and truly epitomizes the Florida Lifestyle with PRIVACY - a Charming Pond and Mature Trees are your back yard! But it gets even better: the sellers are offering buyers the OPTION: to buy unfurnished OR to purchase Some or a Majority of the Designer Furnishings / Decor ala carte on a separate contract. Whether Full-Time or Part-Time residency is in your future, you will FALL IN LOVE w/ Sunrise Preserve AND this barely lived-in Model Home. You'll feel welcomed by a spacious entry with timeless finishes into a stunningly beautiful & modern home. Ask your realtor or the listing agent for the Summary of Upgrades & Features List. Built by Mattamy Homes, this Dayspring model has more than $240k in structural & design upgrades!! Including: high level porcelain tile flooring, high level cabinetry, tray/coffered ceilings with crown molding, 8' doors, High-End GOURMET / CHEF'S Kitchen with ALL Top-Of-The-Line KITCHENAID Appliances, stunning quartz countertops, gas cooktop, double ovens, 42' kitchen cabinets, Smart Home ready, surround sound, upgraded fixtures & ceiling fans, recessed lighting throughout, and much more! The Owner's Suite provides ample space and is well-appointed with a Large and Luxurious En-Suite Bathroom with Dual/Separate Vanities; an exquisite, oversized Shower; a private water closet AND His & Hers Walk-In Closets. But perhaps the BEST part of this home is bringing the Indoors OUT and the Outdoors IN! Situated East/West, you'll enjoy the morning Sunrise from your spacious front porch - AND Stunning Sunsets from the exceptional Caged Pool/Spa/Lanai offering the feeling of being pampered & relaxed - with a serene and private backdrop of a charming pond & mature trees, you'll enjoy nature to the fullest! FEEL CONFIDENT with ZERO storm damage: a base elevation of 21+ feet above sea level, block construction, hurricane shutters, AND the house/structure is designated to be Flood Zone X - Peace of Mind! There is NO CDD fee and Sunrise Preserve's low HOA fee provides complete community and owner landscaping AND the many Resort-Style Amenities: Clubhouse, Fitness Center, Pool, Spa, Pickleball, Tennis, Bocce Ball, Gathering Room, BBQ area, and More! The Sunrise Preserve neighborhood is also Large Pet-Friendly and is located in one of the BEST small cities: Sarasota, FL - where just part of the allure is World Class Siesta Key Beach, Numerous Outdoor & Water Activities, a wide variety of Cultural and Performing Arts & Entertainment... plenty of Shopping, Dining, Boating, Fishing, Live Music, Farmer's Markets, Golf, Kayaking - as well as Airports, Mote Marine, Benderson Rowing - and not too far for a trip to Disney World or to catch a Cruise Ship out of Tampa Bay. This Neighborhood and former Model home will stand OUT and ABOVE the rest!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Janine Kloiber
$950,000 (USD)
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Sarasota Area Land

Active

7676 Midnight Pass Road Sarasota, FL 34242

Bed
0 Baths
sqft
MLS# A4669790
An extraordinary opportunity awaits to create your own private waterfront oasis on world-renowned Siesta Key. Located at 7676 Midnight Pass Road, this expansive 0.43-acre cleared and level lot offers the ideal canvas for a custom coastal retreat that embodies tranquility, luxury, and the essence of island living.

Positioned along the serene waters of Heron Lagoon, the property features approximately 111 feet of peaceful, protected waterfront—perfect for designing your own dock for kayaking, paddleboarding, or simply enjoying the beautiful views of the lagoon. The setting is quiet, secluded, and immersed in natural beauty, delivering a true sense of sanctuary.

All just moments away from the dazzling white sands of Siesta Key Beach, consistently ranked the #1 beach in the United States for its powder-soft quartz sand, vibrant turquoise waters, and breathtaking sunsets. Here, you are close enough to stroll or bike to the shoreline yet tucked away in your own world of serene waterfront living.

The lot is cleared, spacious, and ready to build, with utilities already available—offering a seamless start to designing your dream coastal estate without the delays of demolition or site preparation.

This is truly a rare chance to craft your own slice of paradise on one of Florida’s most coveted barrier islands. Do not miss the opportunity to transform this exceptional property into the Siesta Key retreat you’ve always imagined.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Mairead Smialek
$949,000 (USD)
Active

Longboat Key Area Condominium

Active

1065 Gulf Of Mexico Drive 603 Longboat Key, FL 34228

2 Bed
2 Baths
1503 sqft
MLS# A4671687
Virtual Tour
Beachplace Penthouse with Gulf Views — Top-Floor Residence with Direct Beach Access
Discover an inviting top-floor retreat in Building 10 at Beachplace, offering direct access to the Gulf of Mexico and wide views of the community’s lush landscape, sparkling shoreline, and partial Bay vistas. This furnished 6th-floor residence provides a bright coastal setting, ready for your personal touch.
New impact floor-to-ceiling sliders and windows (2024) illuminate the more than 1,500-square-foot layout, bringing natural light into the open living and dining areas and connecting seamlessly to the beach-to-bay terrace.
The kitchen sits at the center of the home and offers an efficient design with eating space, breakfast bar seating, and laundry closet. The split-bedroom layout enhances privacy. The primary suite includes terrace access, built-in closet with dressing area, and an en-suite bath. The guest suite, located on the opposite side of the residence, is positioned to enhance privacy.
Additional conveniences include one under-building parking space (deeded, covered) plus additional outside parking, and generous storage.
Beachplace is a gated Gulf-front community known for resort amenities and well-managed operations. Residents enjoy 24-hour security, on-site management, a large clubhouse, fitness center, tennis courts, walking paths, and a Gulf-side sundeck with heated pool and spa. A private boardwalk leads directly to the beach. The community’s amenities also include a spa, sauna, meeting rooms, and beautifully maintained grounds.
Ideally positioned along the southern end of Longboat Key, this residence places you minutes from the island’s best recreation and conveniences. Enjoy nearby marinas, championship golf at the Longboat Key Club, waterfront dining, and the boutiques of St. Armands Circle. Downtown Sarasota—home to world-class arts, theaters, galleries, and the Bayfront Park—lies just over the bridge. With wide beaches, tropical landscaping, and exceptional amenities, Beachplace offers an effortless coastal lifestyle in one of Sarasota’s most desirable Gulf-front settings.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$939,000 (USD)
Pending

Longboat Key Area Condominium

Pending

3080 Grand Bay Boulevard 516 Longboat Key, FL 34228

2 Bed
2 Baths
1380 sqft
MLS# A4670274
Virtual Tour
One or more photo(s) has been virtually staged. Perfectly positioned within the sought-after Grand Bay community, this Aruba residence blends convenient design, refined comfort, and a premier Longboat Key lifestyle. Overlooking Sarasota Bay, the golf course, and the downtown skyline, this two-bedroom home offers a combination of privacy, panoramic vistas, and recent designer enhancements.
Set behind the gates of Bay Isles, this corner residence is bathed in natural light from expansive floor-to-ceiling glass doors and windows. The open great room serves as the heart of the home, offering a flexible space for entertaining and relaxing, framed by captivating views of the bay and city beyond. A wraparound balcony extends the living area outdoors, ideal for morning coffee, al fresco dining, or evening sunsets.
The 2025 kitchen renovation introduced a complete reimagining of this important space—featuring custom cabinetry, removal of overhead soffits for added height and openness, upgraded plumbing, new LED and under-cabinet lighting, and all-new hardwood flooring carried throughout the residence. The modernized kitchen blends timeless finishes with functional elegance, offering ample workspace and stylish appeal for both everyday use and entertaining.
The primary suite is a tranquil retreat, capturing water views and featuring an en-suite bath with dual sinks, a soaking tub, and a separate walk-in shower. A spacious walk-in closet provides exceptional storage. The guest bedroom offers options to act as an office or den, allowing effortless flexibility for visiting guests. Additional features also include two under-building parking spaces and a private storage locker.
Within the secure and beautifully maintained Grand Bay community, residents enjoy an array of luxury amenities, including two resort-style swimming pools and spas, fully equipped fitness center, and clubhouse, tennis courts and pickleball, 24-hour guarded gate entry and on-site management.
Grand Bay’s location behind the Bay Isles gates grants owners private beach access to the Gulf of Mexico through the Bay Isles Beach Club. The Longboat Key Club golf course and marina are nearby, offering exceptional recreation options.
Beyond the gates, you’re moments from St. Armands Circle’s boutiques and fine dining, the vibrant arts and theater scene of downtown Sarasota, and world-renowned beaches along Longboat and Lido Key. Whether you’re seeking a seasonal escape or a year-round residence, this Grand Bay condominium captures the essence of coastal sophistication—where modern updates meet the serenity of bayfront living.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$939,000 (USD)
Pending

Osprey Area Single Family Home

Pending

392 Park Trace Boulevard Osprey, FL 34229

4 Bed
3 Baths
2802 sqft
MLS# A4668610
Virtual Tour
Under contract-accepting backup offers. Set on a premier lakefront lot in Osprey, 392 Park Trace offers serene water views, incredible privacy, and a lifestyle surrounded by nature. Backing to Oscar Scherer State Park and just 1.9 miles from the Gulf waters and waterfront tiki bars, this home embraces Florida living. The Legacy Trail trailhead is only a quarter-mile away, connecting you to miles of scenic paths for biking, running, and exploring.

Designed to capture its peaceful surroundings, the home features wide-open living spaces and large windows that fill every room with natural light. The floor plan includes four spacious bedrooms, three full baths, and a flexible office or den.

The open kitchen is a true centerpiece, with granite counters, stainless steel appliances, a walk-in pantry, and a large island ideal for gathering with family and friends. Soaring ceilings, crown molding, and rich flooring bring warmth and elegance throughout.

Step outside to your private lanai and take in the captivating lake views that first made the current owner fall in love with this home, a view you truly have to experience for yourself!

The sparkling pool and spa, enclosed in a recently redone cage, along with a fenced dog run or garden area, create an inviting space to unwind and relax. Plus, there is a 2.5-car garage that completes this exceptional property.

Also located minutes from Siesta Key Beach, boutique shopping, fine dining, and the top-rated Pine View School, this home delivers the serenity of the Gulf Coast with everyday ease.

392 Park Trace isn’t just a place to live… it’s a place to belong.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Ryan Skrzypkowski
$930,000 (USD)
Active

Sarasota Area Condominium

Active

6518 Midnight Pass Road 209 Sarasota, FL 34242

2 Bed
2 Baths
1215 sqft
MLS# A4673460
Virtual Tour
Experience true beachfront living on world-famous Siesta Key. This turnkey-furnished 2-bedroom, 2-bath residence offers an exceptional opportunity to own along Siesta Key’s shoreline, combining Gulf views with impressive short-term rental income potential. Located just steps from the island’s iconic powder-white sand, this inviting condominium is designed for comfort, convenience, and effortless coastal living.

Inside, an open and airy layout welcomes you with abundant natural light and luxury vinyl flooring throughout the main living areas. The living room flows seamlessly to large sliders that open to a wonderful 14x7 private patio, the perfect place to relax and take in the stunning views of the Gulf of Mexico.
Kitchen features wooden cabinets providing lots of ample storage, a breakfast bar for additional seating, and a functional layout ideal for everyday cooking or hosting guests. The primary suite includes ceramic tile flooring, a private en-suite bath, and ample closet space. Both bathrooms have been updated with new vanities and granite countertops—the primary bathroom offering a standalone shower, while the guest bathroom features a convenient tub/shower combination. Every window and sliders have recently been replaced by association in the last few years

This community is one of the few on Siesta Key allowing weekly rentals, paired with a professional on-site rental management team, creating strong income potential while still giving you the freedom to enjoy your own beach retreat.

Resort-style amenities elevate the beachfront experience. Enjoy a beach-facing pool and tennis courts, fitness center, rooftop lounge with panoramic Gulf views, and outdoor grilling/bar areas with firepits—everything you need for relaxed days and evenings by the water. Direct beach access places you just steps from the shoreline.

Ideally located near Siesta Key Village’s vibrant shops, dining, and entertainment, this residence offers the perfect combination of coastal living, convenience, and investment appeal—an outstanding opportunity to enjoy and share the Siesta Key lifestyle.
Listing Courtesy of STELLAR / Coldwell Banker Realty / David Leventhal
$919,000 (USD)
Active

Sarasota Area Single Family Home

Active

2021 Misty Sunrise Trail Sarasota, FL 34240

5 Bed
4 Baths
3182 sqft
MLS# A4667841
Virtual Tour
Nestled beneath a lush canopy of majestic oaks and palms, this exceptional residence embodies a lifestyle that seamlessly blends the timeless charm of Old Florida with the contemporary comforts of a newer home. Located in the highly desirable Sylvan Lea community of Sarasota, the property sits on a picturesque, tree-lined street where neighbors enjoy leisurely strolls, and breathtaking sunrises greet you each morning. Step inside to discover a meticulously designed and pristinely maintained two-story home featuring 5 bedrooms, 4 bathrooms, and versatile spaces which could be used for a virtual office or an expansive workout room—perfectly suited for modern living. The heart of the home is the inviting great room, enhanced by a trey ceiling and effortless access to the gourmet kitchen. Here, stone countertops, a generous island, stainless steel appliances and abundant white cabinetry create an ideal setting for both casual family meals and sophisticated entertainment. The main floor offers true convenience and privacy with a split plan offering three spacious guest rooms. Escape to the lavishly spacious primary suite, featuring a spa-inspired bathroom with dual vanities, a custom-tiled shower, separate soaking tub, and a private water closet. Enjoy abundant storage in the expansive walk-in closet. The full laundry room located on the main floor adds practicality and ease to daily routines. Upstairs, a fifth bedroom and bonus area with a full bathroom offer a private retreat—perfect for guests or in-laws seeking their own space to relax and unwind. Step outside to embrace the Florida lifestyle on the expansive screened brick paver patio, featuring a private, heated pool—your personal oasis for evening gatherings or peaceful relaxation. The fully fenced backyard creates wonderful space, allowing your four-legged family members to roam safely and freely. A spacious three-car garage completes the home, providing ample storage and convenience. With whole home hurricane protection, a brand-new roof and fresh interior and exterior paint, this home offers true maintenance-free living. Sylvan Lea presents a rare Sarasota experience with peaceful, canopy streets that feel secluded, yet you’re just minutes from I-75, downtown Sarasota, and the world-renowned white-sand beaches of Siesta Key. Enjoy the perfect blend of convenience and tranquility in this remarkable home.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Stephanie Church
$900,000 (USD)
Active

Osprey Area Condominium

Active

401 N Point Road 304 Osprey, FL 34229

3 Bed
3 Baths
2778 sqft
MLS# A4659785
Virtual Tour
Give yourself the gift of refined living in this expansive 2,778 square foot residence—the largest non-penthouse floor plan available in Meridian at The Oaks Preserve. Every detail in this meticulously maintained, and beautifully updated condominium has been thoughtfully designed to offer comfort, sophistication, and versatility, making it the perfect sanctuary for luxury living every day! Step inside and discover a home where space abounds and possibilities flourish. With three generously sized bedrooms, plus a dedicated dining room (currently being used as a den) and a versatile office/den or 4th bedroom, this home provides all the room you need to work, relax, and entertain, with the flexibility to use the rooms as you see fit. The great room is bathed in natural light, its gleaming wood floors enhancing the clean, contemporary lines of the interior. The updated kitchen will delight any home chef, offering optimal space for cooking and storage, whether you are preparing a casual breakfast or hosting a formal dinner. Enjoy your meals in the dining room, at the breakfast bar, in the cozy nook, or take them outside to the large, screened balcony, where a ceiling fan and the serene backdrop of a lush tropical preserve provide the ideal setting for alfresco dining. The small dry bar with wine cooler and cabinets to store your drink supplies and display your glassware is the perfect addition for when you are entertaining guests. Retreat to a sumptuous master suite. The large, carpeted bedroom is filled with natural light, and outfitted with a ceiling fan, plantation shutters, and custom closets. The master bathroom has been beautifully redone. With a soaking tub, separate shower and water closet, this space is absolutely gorgeous. Every inch of this unit has been curated to deliver both style and functionality, ensuring you feel pampered at every turn. Additional features include a large laundry room, Kevlar roll down hurricane shutters, two premium parking spaces and high-quality upgrades throughout. Club membership is required with homeownership. Residents of Meridian enjoy exclusive access to a private pool, relaxing spa, and a fully equipped workout room. Beyond these, The Oaks offers an impressive array of amenities including 36 holes of championship golf across two courses, twelve HAR-TRU tennis courts (four lighted), a state-of-the-art Wellfit Center, three on-site restaurants with year-round dining, croquet, bocce and pickleball courts and an active social calendar.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Steve Abbe