My Active Listings

Some or all of the listings below are provided by the Siesta Key office.
$15,000 / mo (USD)
Active

Sarasota Area Rental

Active

22 Sandy Cove Road Apt 10-5 Sarasota, FL 34242

3 Bed
3 Baths
1898 sqft
MLS# A4658557
Virtual Tour
RATES AND AVAILABILITY VARY. AVAILABLE SEASON 2026! Welcome to a completely renovated, light-filled penthouse in the exclusive Sandy Cove community — where coastal design meets breathtaking Gulf views in every direction. This professionally managed 3-bedroom, 3-bath residence is fully turnkey furnished and thoughtfully designed for relaxed, upscale living.

Every inch of the home has been updated with all-new finishes, furnishings, and a refined coastal palette that creates a bright, airy atmosphere. Multiple balconies offer seamless indoor-outdoor living, including a private balcony off the primary suite — perfect for enjoying expansive views of the Gulf, Lido Beach, and the Downtown Sarasota skyline.

What makes this unit even more unique is its personal exterior camera system, which provides a live, panoramic view from behind the exterior walls. It gives you a remarkable visual connection to the beach and water, even from inside the unit — maximizing the sense of space and view in a way most properties simply can’t.

Sandy Cove offers a private beach for residents and guests, ideal for dolphin watching, boat spotting, and soaking in Sarasota’s iconic sunsets. You're just moments from the vibrant shops and restaurants of Siesta Key Village and a short drive from all the culture, dining, and entertainment of Downtown Sarasota.

Whether you're here to relax, entertain, or explore, this one-of-a-kind penthouse delivers an unforgettable Siesta Key experience — turnkey, elevated, and unlike anything else on the market.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Cole Collins
$4,700 / mo (USD)
Active

Sarasota Area Rental

Active

8625 Midnight Pass Road 305B Sarasota, FL 34242

1 Bed
1 Baths
697 sqft
MLS# A4670970
Virtual Tour
Siesta Key! Newly renovated and fully furnished 1BR/1BA condo set in a relaxed, resort-style waterfront community on Siesta Key. This gulf/beach-to-bay condominium features expansive boat docks (no extra usage fee), two heated pools (bay & gulf/beach side), private/individual gulf/beach side cabanas, kayak racks, 2 BBQ grill patios, exquisite sunrises & sunsets & so much more ~ everything a boating enthusiast or beach lover could dream of. Located in the coveted Bay Tree Club on South Siesta Key, this is your chance to embrace coastal life at its finest, whether you're exploring the Gulf by boat or lounging on sugar-sand beaches. The pools & grill areas provide idyllic locations for all gatherings. This freshly remodeled condo features a generous sized living room with a French/Juliet balcony overlooking the bay side heated pool & lush grounds with some views of the Sarasota Intracoastal Waterway. The dining area has a pass-through access to the updated designer kitchen featuring quartz countertops & new self-closing cabinets/drawers The primary bedroom has a large closet providing ample storage. Along with the foyer closet, you will have room for all your possessions. Don't forget the beach side cabana for your gear. Renovated full bath with a tub completes. Each building is equipped with elevators and laundry rooms (coin-op) on every floor ensure everyday comfort is never out of reach. During your stay, explore all the unmatched amenities, nearby restaurants & shops. Bonus is The Breeze Trolley stop just outside. Hop aboard and enjoy free rides to & from Siesta Beach (recently voted #1 in the US & #4 Globally) and Siesta Village. Stay aboard to Downtown Sarasota where you can transfer to the Bay Runner for jaunts to iconic St. Armands Circle & beyond. Life is good here ~ Welcome to your Coastal Oasis Getaway! IN Season, January-April, 5300/month. OFF Season, May-December, $4700/month. Weekly option available for off season. Sorry no pets. Owner/Agent.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Aurelia Gilbert
$3,350 / mo (USD)
Active

Sarasota Area Rental

Active

5880 Midnight Pass Road 306 Sarasota, FL 34242

2 Bed
2 Baths
1498 sqft
MLS# A4665457
Virtual Tour
Available April 2026 and Beyond! The rate shown reflects the annual rental price. Seasonal rates for April 2026 may vary. Don’t miss the opportunity to secure this property, reach out for availability and details. Step into paradise at Casarina, a beautifully maintained beachfront community right on Siesta Key’s world-famous Crescent Beach. With 200 feet of private beach access, you’re just steps away from the soft white sands and turquoise waters that make this destination so special.
Your third-floor condo retreat comes fully furnished and ready for your stay. Enjoy a newly updated kitchen, modern luxury vinyl floors, an updated guest bath, and the comfort of a brand-new AC unit. Start your mornings with coffee on the 17-foot screened balcony overlooking serene gardens, and catch a glimpse of the Gulf and pool area through the palms.
Casarina offers the perfect blend of relaxation and activity. Spend your days unwinding at the beachside pool and spa, challenge friends to a game of tennis or pickleball, or take in the sunsets from the elevated beach deck. The clubhouse is a welcoming space to meet other guests, and the lush 7-acre grounds are ideal for strolling. When you’re ready to explore, hop on the free Siesta Key Trolley for easy access to local dining, shopping, and entertainment. Paddle boarding, kayaking, biking, or simply soaking up the Florida sun—the choice is yours.
This Casarina condo offers the ideal island escape with resort-style amenities and all the comforts of home.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Cole Collins
$4,500,000 (USD)
Pending

Sarasota Area Multi-Family Home

Pending

544 Canal Road Sarasota, FL 34242

8 Bed
8 Baths
6490 sqft
MLS# A4657990
Virtual Tour
Under contract-accepting backup offers. SIESTA KEY INVESTMENT PROPERTY. Great location! Welcome to the Wildflower. Just steps from the #1 Beach in USA. Nestled within a tropical oasis, this charming 8 plex 4 ground level units and 4 second level units, with 8 parking spaces offers a unique blend of comfort and natural beauty. Surrounded by vibrant tropical flora, enter the common area courtyard centered around a sparkling heated pool, perfect for relaxing after a day at the beach. The courtyard backdrop includes a standing waterfall that offers the tranquil sounds of nature. A very unique detail to any outdoor living space. Adjacent from the pool are two screened communal areas. A game room, with tv, ping pong table, pool table, arcade & washer/dryers and restroom with shower. The second lanai has a sectional sitting area with tv, fire pit and sauna. Plenty of beach and pool accessories, noodles, rafts, beach chairs, carts, etc,. for guests to enjoy. There is also a dock, across the street that is included with the sale of the property. Ideal for kayak launching or fishing. The canal leads to the Siesta Key Grand Canal. The interiors are adorned with NEW modern finishes, appliances, and furnishings. Interior spaces can be combined by interior door. Each room has been eloquently decorated with a coastal theme. Guests can take leisurely strolls to Siesta Key Village shops, restaurants and entertainment. The free trolley stop is also around the corner. This turnkey property is in like NEW CONDITION and is the perfect investment opportunity. Schedule your showing to see this amazing slice of paradise.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Kathleen "Katie" Cintron
$1,899,000 (USD)
Pending

Sarasota Area Single Family Home

Pending

1841 Datura Street Sarasota, FL 34239

4 Bed
4 Baths
2293 sqft
MLS# A4676725
Virtual Tour
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Live the ultimate Southside Village lifestyle in this one-of-a-kind Craftsman-style home, where charm meets everyday convenience in a rare blend of elegance, craftsmanship, and modern sophistication. Rebuilt to current code in 2014, it offers the refined feel of a coastal farmhouse, with every detail thoughtfully designed for comfort, efficiency, and timeless appeal nestled in one of Sarasota’s most sought-after and walkable neighborhoods. Step through the privacy gates into a lush, fully fenced yard where a rich paver brick driveway, terrace, and walkways guide you through a serene, low-maintenance garden. Featuring artificial turf, vibrant flowering shrubs, and fruit trees, the exterior is not only incredibly private but also immaculately maintained for effortless enjoyment. Every inch of the property has been meticulously manicured, a true testament to the care it has received. Inside, the floor plan strikes the perfect balance between open living and intimate gathering spaces, ideal for both entertaining and everyday living. The kitchen and living room connect seamlessly, creating a warm, functional flow perfect for hosting or simply relaxing at home. The first-floor primary suite is spacious and secluded, featuring his and hers walk-in closets, dual vanities, and a large walk-in shower, a true retreat within the home. Also on the main level is a sun-filled bedroom that offers wonderful flexibility: perfect as a guest room, home office, or children’s playroom. Upstairs in the main house, you'll find an additional bedroom and a generously sized flex space that is ideal for a game room, entertainment room, or home gym, depending on your needs. The detached two-car garage adds both function and charm, offering an upstairs guest suite complete with a full bath, wet bar, and mini-fridge that is greatly suitable for visitors, a private studio, or a quiet home office. This home truly looks like it belongs on the cover of Southern Living or Coastal Living magazine, thanks to its effortless blend of style, warmth, and timeless appeal. Tucked away on one of Sarasota’s most beloved streets, you're just steps from Morton’s Market, Libby’s, and other neighborhood favorites. Located in the highly regarded Southside Elementary School district, the home offers the very best of the West of Trail lifestyle, walkable to restaurants, boutique shops, and Sarasota Memorial Hospital, with easy bike access to downtown Sarasota, St. Armands Circle, and our world-famous beaches. The best of both worlds: a Southside Village residence with a 2014 effective date, blending modern updates with Sarasota’s enduring charm.
Listing Courtesy of STELLAR as distributed by MLS GRID / Coldwell Banker Realty / Cole Collins