Longboat Key Listings

Some or all of the listings below are provided by the Longboat Key office.
$1,800,000 (USD)
Active

Holmes Beach Area Single Family Home

Active

220 36th Street Holmes Beach, FL 34217

3 Bed
4 Baths
2016 sqft
MLS# A4664041
Virtual Tour
PRICE IMPROVEMENT on this Ultimate Gulfside Retreat on Holmes Beach, Anna Maria Island!

Successful Vacation Rental with WEEKLY RENTALS and NO HOA! Just 200 feet from the sugar-sand shores and turquoise waters of the Gulf of America! This updated, coastal-inspired three-level beach home with a private elevator offers the perfect blend of luxury, comfort, and investment potential.

With over 2,000 sq. ft. of bright, open living space, 3 bedrooms, 3 Ensuite Bathrooms, plus a Half Bath, a private pool and hot tub, and SWEEPING GULF VIEWS from your balcony, this is truly the ultimate island escape. Currently a high-performing vacation rental generating over $120,000 annually with future bookings in place, this property also makes an ideal primary residence or second home. Offered fully furnished—including sleeper sofas—it’s ready to comfortably accommodate family, friends, and guests.

The main level boasts a light-filled OPEN CONCEPT LIVING AREA with large windows and sliding glass doors overlooking lush tropical landscaping. The CHEF'S KITCHEN features newer stainless-steel appliances, dual refrigerators, expansive granite counters, a wine cooler, and Walk In Pantry. Entertaining is effortless with a breakfast bar, indoor dining space, and outdoor dining options. The primary suite on this level is a private retreat with dual walk-in closets and a spa-style ensuite bath featuring both a shower/tub combo and a separate walk-in shower, plus a water closet with bidet.

Take the private elevator to the upper level where you’ll find a SECOND PRIMARY SUITE beautiful bathroom and walk-in closet, a third spacious bedroom with ensuite bathroom, and a separate laundry room.

The ground floor welcomes you with a large foyer and a VERSITILE FLEX SPACE, perfect for storage, crafts, or a media room, along with access to the OVERSIZED 2-CAR GARAGE! Additional upgrades include a reverse osmosis system and three newer air conditioners for consistent comfort throughout the home.

Step outside to your private, fenced outdoor oasis, complete with sparkling POOL, bubbling HOT TUB, and plenty of seating for lounging or alfresco dining while enjoying the Gulf breezes and breathtaking sunsets.

Perfectly situated at Holmes Beach with its vibrant shops, restaurants and beaches, and less than 2 miles from the shops beaches and restaurants of Bradenton Beach—and just steps from the Gulf. Longboat Key, Sarasota, Siesta Key and SRQ Airport are also close by. This rare property combines island living at its best with proven rental income.

Schedule your private showing today—your Anna Maria Island paradise awaits!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Pamela "Pam" Bailey
$1,799,000 (USD)
Active

Longboat Key Area Condominium

Active

585 Sanctuary Drive B502 Longboat Key, FL 34228

3 Bed
3 Baths
1823 sqft
MLS# A4679102
Virtual Tour
Perched on the fifth floor of Building 1 at The Sanctuary at Longboat Key Club, this corner residence offers sweeping views that extend from the Gulf of Mexico across the Longboat Key Club golf course to Sarasota Bay and the downtown skyline. A wraparound terrace enhances the setting, creating an exceptional indoor-outdoor experience with ever-changing light and scenery throughout the day.
Inside, the open floor plan spans nearly 1,900 square feet and is designed to maximize both comfort and function. Walls of glass sliders in multiple rooms open directly to the terrace, allowing for sunset views, fresh coastal breezes, and natural light to flow throughout the residence. The living and dining areas connect seamlessly, providing an ideal layout for everyday living or entertaining.
The primary suite is privately positioned and features oversized windows framing sun-filled views, a walk-in closet, and an en-suite bath. Two additional bedrooms are each en-suite, offering flexibility for guests, family, or a home office while maintaining privacy for all. Three full baths complete this thoughtfully arranged residence.
Additional conveniences include one secure, under-building parking space and a dedicated storage unit.
Residents of The Sanctuary enjoy a full complement of resort-style amenities, including a Gulfside swimming pool with cabanas, expansive sundeck, outdoor bar, and an additional heated pool and spa. Tennis courts, a modern fitness center, and a variety of clubhouse activities enhance the Longboat Key lifestyle. A private boardwalk provides direct access to the pristine beach, while a 24-hour manned guard gate and on-site management ensure peace of mind.
Ownership also offers the option to join the renowned Longboat Key Club, available separately, granting access to championship golf, premier tennis facilities, marina services, spa amenities, dining venues, and resort-style social offerings.
Ideally located on Longboat Key, The Sanctuary places you minutes from waterfront dining, boating, and shopping. St. Armands Circle, Lido Beach, and downtown Sarasota’s theaters, galleries, and cultural attractions are all within easy reach—offering a refined coastal lifestyle where natural beauty and convenience meet.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$1,795,000 (USD)
Active

Longboat Key Area Condominium

Active

3060 Grand Bay Boulevard 195 Longboat Key, FL 34228

3 Bed
4 Baths
2250 sqft
MLS# A4677880
Virtual Tour
Positioned high on the south side and 9th floor of Building One, this turnkey-furnished residence at Grand Bay offers expansive Sarasota Bay, golf course and downtown views, refined interiors, and effortless resort living on Longboat Key. Spanning nearly 2,300 square feet, the open layout is framed by walls of glass and a wraparound terrace with access from nearly every room—creating a seamless connection between indoor spaces and the ever-changing water views below.
Recently refreshed with new contemporary furnishings included, the residence is truly move-in ready. The spacious great room flows naturally into the dining area and kitchen, creating an inviting setting for entertaining or relaxed daily living. Floor-to-ceiling glass sliders bring in abundant natural light while showcasing views of the bay, marina, and downtown Sarasota.
The primary suite is a private retreat with terrace access, generous closet space, and a well-appointed en-suite bath. Two additional bedrooms provide flexibility for guests, office use, or extended stays, each positioned to enjoy natural light and views. Electric storm shutters throughout offer convenience and peace of mind.
This residence includes two deeded parking spaces and an additional storage unit, a valuable combination rarely available at this elevation.
Grand Bay is one of Longboat Key’s most sought-after gated communities, offering residents a full suite of resort-style amenities including two heated swimming pools with sundecks, Har-Tru tennis courts, a modern fitness center, clubhouse, and an active social calendar. On-site management and 24-hour security ensure a well-maintained, secure environment. As an exclusive benefit, owners enjoy deeded access to the private Bay Isles Beach Club, where Gulf-front pavilions, grilling areas, and pristine shoreline create the perfect setting for beach days and sunset gatherings.
Located behind the gates of Bay Isles, Grand Bay balances privacy with proximity. Just minutes away are the boutiques and restaurants of St. Armands Circle, the cultural offerings of downtown Sarasota, championship golf and marina access at Harbourside, and the beaches of Lido and Siesta Key. From boating and tennis to theater, dining, and art, this residence places the best of Sarasota living within easy reach.
A rare opportunity to enjoy turnkey bayfront living in one of Longboat Key’s premier communities.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$1,749,000 (USD)
Active

Longboat Key Area Condominium

Active

1211 Gulf Of Mexico Drive 301 Longboat Key, FL 34228

3 Bed
3 Baths
2100 sqft
MLS# A4669896
Virtual Tour
Rarely available north-side corner residence at The Promenade showcases panoramic views of the Gulf of Mexico, Sarasota Bay, white sandy beaches, and the sparkling city skyline. This beautifully designed 2,100 sq. ft. “E” floor plan features three bedrooms and three baths, with a spacious split layout that captures natural light and breathtaking vistas from every room. The expansive living and dining areas flow seamlessly to two private terraces—set your morning coffee down as you watch the sunrise over the bay, and end the day with a glass of wine while taking in the sunset over the Gulf. A stylish wet bar adds the perfect touch for entertaining. The kitchen is a showpiece, featuring 2022 installed Sub Zero refrigerator/freezer, GE Monogram stainless-steel induction cooktop and oven, ASCO dishwasher and GE Monogram microwave / convection oven combo, a white subway tile backsplash, quartz countertops, sleek contemporary white cabinetry, and an eat-in area overlooking the bay. Engineered white oak hardwood floors extend throughout, adding warmth and sophistication. The primary suite offers stunning Gulf views, built-in cabinetry, and two walk-in closets, while the guest suite enjoys downtown views and a private bath. The third bedroom/den opens to a terrace overlooking the Gulf. Includes one deeded parking space and access to resort-style amenities—concierge, 24-hour security, fitness center, an Olympic-size heated pool, four Har-Tru tennis courts, and more.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Ryan Ackerman
$1,695,000 (USD)
Pending

Longboat Key Area Condominium

Pending

3060 Grand Bay Boulevard 154 Longboat Key, FL 34228

3 Bed
4 Baths
2550 sqft
MLS# A4667468
Virtual Tour
Under contract-accepting backup offers. Beautifully renovated and offered turnkey furnished, this 3BR/3.5BA residence is perfectly positioned on the 5th floor of Building I in Grand Bay on Longboat Key. A private elevator opens to an elegant, open layout with new wood floors, architectural details, and recessed lighting. Walls of glass frame sweeping views of Sarasota Bay and the Harbourside golf course. The updated kitchen features all-white cabinetry, stone countertops, designer backsplash, premium stainless-steel appliances, and a wine fridge. The spacious living and dining areas flow to an expansive balcony ideal for relaxing or entertaining. A flexible enclosed bonus room / bedroom offers space for an office, media room, or guests. The primary suite includes custom built-ins, balcony access, a large walk-in closet, and a luxurious updated bath with floating vanities, freestanding tub, and glass shower. Two guest suites offer private baths. Additional features include in-residence laundry and under-building parking. Grand Bay residents enjoy resort-style amenities—two pools and spas, a fitness center with saunas, tennis courts, clubhouse—and private Bay Isles Beach Club access. Optional membership to the Longboat Key Club offers golf, tennis, marina, dining, and beach resort privileges—enhancing the ultimate island lifestyle. Large dogs are welcome.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Bruce Myer
$1,695,000 (USD)
Active

Longboat Key Area Condominium

Active

3040 Grand Bay Boulevard 243 Longboat Key, FL 34228

3 Bed
4 Baths
2550 sqft
MLS# A4667443
Virtual Tour
Set above the sparkling waters of Sarasota Bay, this beautifully updated 3BR/3.5BA, 2,550 sq. ft. residence in Grand Bay on Longboat Key offers refined living with a seamless, well-planned layout. From the moment the private elevator opens to your foyer, the atmosphere feels bright and balanced, with rich wood floors, crown molding and recessed lighting framing panoramic views of the bay, Harbourside golf course and pond. The spacious living room opens to an expansive terrace overlooking the water, while the formal dining area provides a graceful space for entertaining. The reimagined kitchen combines form and function with all-white cabinetry, stone countertops, stainless-steel appliances and a breakfast bar. A flexible third bedroom—with custom built-ins and terrace access—can also serve as a private office or sitting room. The primary suite is a peaceful retreat with terrace access, a large walk-in closet, and a luxurious bath featuring dual vanities, soaking tub, glass-enclosed shower and bidet. Additional highlights include a laundry room and one covered parking spaces. Grand Bay residents enjoy resort-style amenities including two pools, a clubhouse, fitness center, tennis courts, and deeded beach access through the private Bay Isles Beach Club for exclusive Gulf-front enjoyment.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Bruce Myer
$1,690,000 (USD)
Active

Osprey Area Single Family Home

Active

76 Osprey Point Drive Osprey, FL 34229

3 Bed
5 Baths
4364 sqft
MLS# A4672843
Virtual Tour
COMPLETELY UPGRADED IS NOT AN EXAGGERATION! This Bo MacEwen–designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in creating a refined, sophisticated residence that still feels warm and inviting. This home truly shows like new, and a full upgrade list is available upon request. Inside, the spacious layout includes a formal dining room, formal living room, and a cozy den with gas fireplace. Crown molding, tray ceilings, plantation shutters, and custom built-ins elevate the elegance throughout. Multiple sets of French doors open to the very private pool area, filling the home with natural light and enhancing indoor–outdoor living. The chef’s kitchen has been refreshed and features a six-burner Viking gas range with grill, Viking hood, Sub-Zero refrigerator/freezer, butler’s pantry, breakfast bar, and dining nook. The primary suite boasts two walk-in closets and a recent down-to-the-studs, resort-level bathroom remodel—one that would make even the Ritz envious. One guest suite occupies the west wing, while a spacious second-level suite adds comfort and flexibility. Significant structural upgrades include NEW low-E hurricane-impact windows and skylights, roll-down hurricane shutters (front and rear), and a whole-house generator for added peace of mind. Exterior enhancements include a NEW paver driveway and pool deck, extensive landscape lighting, and a very private pool area with new built-in grill and bar. Located in one of the Gulf Coast’s premier country club communities, The Oaks offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center. Club membership is required with homeownership.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Steve Abbe