Cail Grande Group

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Cail Grande Group Real Estate is our profession. People are our priority. With 60+ years of experience, the Cail Grande Group is a trusted leader in Sarasota’s luxury market.

Lifelong locals, Jason and Tom deliver personalized service with integrity and proven results. Tom Cail and Jason Grande formed the Cail Grande Group in 2007. They started working together when two clients who jointly owned a property each hired their own Realtor to sell it. The house had been on the market for almost two years. Tom and Jason learned that they worked well together, averting a potentially contentious situation and keeping both clients happy. The house sold within two months of the listing contract. They decided to join forces permanently, sharing a mutual goal to make other peoples’ needs a priority. TOM CAIL
Tom moved to the Sarasota area at the age of 10, when his parents moved here from Boston. His career path first led him to public relations, then to teaching. He found his niche in real estate and has been a licensed Realtor since 1992.

“With a combined 40 years experience in the Sarasota Real Estate market and us both having lived here since the age of ten, Jason and I are in the unique position of having experienced all that Sarasota has to offer both professionally and personally. We both love making the deal happen for our clients and we both love the Sarasota lifestyle, which is the perfect blend for anyone looking for agents to sell or buy a home in the Sarasota area.”

JASON GRANDE
Jason has lived in Sarasota since he was 10 years old, and loves the outdoor and waterfront lifestyle. A licensed Realtor for more than 20 years, he has navigated numerous real estate market cycles, helping clients through every challenge.

“Making the deal happen for our clients is our pledge to each and everyone of our clients. Tom and I both grew up in Real Estate households, Tom‘s mom was a top producing Realtor in Sarasota and my dad was a developer, so we both grew up with the housing industry in our blood. When something has been a part of your life for this long, I think the passion for what we do, and the passion we have for getting the job done, shines through in every transaction.”

103 Fillmore Drive is under contract, and the sellers are accepting backup offers.St. Armands homes this close to Lido B...
11/05/2026

103 Fillmore Drive is under contract, and the sellers are accepting backup offers.

St. Armands homes this close to Lido Beach and the Circle rarely come up, and this one is fully renovated. A saltwater pool, a firepit lounge and an outdoor bar with a grill sit on a private, palm-lined lot of just under a third of an acre. A new tile roof went on in 2025, and the flood policy is assumable.

4 bedrooms (or 3 plus a den) · 3 baths · 2,908 sq ft
Offered at $2,199,000

If this location is on your list, now is the time to position a backup offer.

Cail Grande Group by
www.cailgrande.com

11/04/2026

Sarasota isn't just where we work. It's where we grew up.

Tom has called Sarasota home since 1977 and has been selling it since 1992. Jason moved here at 12 and has spent more than 30 years in the business. Together, that's more than five decades of watching Siesta Key and the neighborhoods west of the Trail become what they are today.

We know the canals, the barrier-island history, and the builders whose work holds up. That history is what we bring to every listing and every negotiation.

Welcome to the Cail Grande Group.

—
The Cail Grande Group | RE/MAX Alliance Group
Tom Cail 941.780.2245 | Jason Grande 941.504.6678
cailgrande.com

Top 100 in Florida. RE/MAX Small Teams, Q3.We both moved to Sarasota at age 10. Tom grew up watching his mother become o...
11/04/2026

Top 100 in Florida. RE/MAX Small Teams, Q3.

We both moved to Sarasota at age 10. Tom grew up watching his mother become one of the city's top-producing Realtors. Jason grew up on job sites with his father, a local developer. Fifty-six years of combined experience later, the approach hasn't changed: know the land, know the history, and tell clients the truth about value.

This recognition belongs to the families who trusted us this quarter, from the neighborhoods West of Trail to the shores of Siesta Key. Thank you for choosing us.

Buying or selling in Sarasota? We'd welcome the conversation.

Tom Cail | 941-780-2245
Jason Grande | 941-504-6678
cailgrande.com

The Cail Grande Group | RE/MAX Alliance Group

103 Fillmore Drive is under contract, and the sellers are accepting backup offers.A renovated pool home on just under a ...
10/28/2026

103 Fillmore Drive is under contract, and the sellers are accepting backup offers.

A renovated pool home on just under a third of an acre, a few blocks from Lido Beach and St. Armands Circle. A new tile roof went on in 2025, and the flood policy is assumable.

4 bedrooms (or 3 plus a den) · 3 baths · 2,908 sq ft
Offered at $2,199,000

If this location is on your list, now is the time to position a backup offer.

Cail Grande Group by
www.cailgrande.com

Siesta Key, from the pool deck to the rooftop.At 5547 Avenida Del Mare, evenings start at the heated saltwater pool and ...
10/27/2026

Siesta Key, from the pool deck to the rooftop.

At 5547 Avenida Del Mare, evenings start at the heated saltwater pool and spa, which has a sun shelf and a custom entertainment bar. They end on the 950 sq ft rooftop terrace, with Gulf views at sunset. Siesta Key Beach and Siesta Village are a walk away.

The primary suite has Gulf views and a private balcony. Each of the four ensuite guest rooms has its own balcony and walk-in closet. The chef's kitchen is fitted with GE Monogram appliances, and a private elevator reaches every level.

We grew up here. When you're ready to buy or sell in Sarasota, we know what's behind every address.

Cail Grande Group by
www.cailgrande.com

Come see us today!!!! 1-4 PM
10/24/2026

Come see us today!!!! 1-4 PM

Join us tomorrow 10/24/26 from 1-4.  New construction beach house with rooftop deck with incredible views!
10/23/2026

Join us tomorrow 10/24/26 from 1-4. New construction beach house with rooftop deck with incredible views!

103 Fillmore Drive is officially under contract! 🎉This beautifully renovated pool home, just blocks from the white sands...
10/23/2026

103 Fillmore Drive is officially under contract! 🎉

This beautifully renovated pool home, just blocks from the white sands of Lido Beach and moments from the shopping, dining, and charm of St. Armands Circle, is one step closer to its new owners.

Cail Grande Group by RE/MAX Alliance Group
www.cailgrande.com

Open this Saturday October 24 1-4!  New construction, 5 bedrooms, rooftop deck just two blocks from Siesta Beach!!Experi...
10/22/2026

Open this Saturday October 24 1-4! New construction, 5 bedrooms, rooftop deck just two blocks from Siesta Beach!!

Experience elevated coastal living in this exceptional 5-bedroom, 5.3-bath contemporary retreat, ideally located just steps from world-famous Siesta Public Beach and a short stroll to Siesta Village, where boutique shopping, dining, lively nightlife, and island charm await. Thoughtfully designed for effortless resort-style living, this four-level residence offers breathtaking Gulf views, expansive light-filled interiors, a private elevator, and extraordinary indoor and outdoor entertaining spaces. As the day draws to a close, the western sky transforms into a spectacular canvas of brilliant oranges, pinks, purples, and golds, creating unforgettable sunsets over the Gulf that can be enjoyed from multiple levels of the home, including the stunning rooftop retreat. The private outdoor oasis features a heated saltwater pool with sun shelf, spa, custom entertainment bar, lush tropical landscaping, and covered parking for up to four vehicles. Inside, the home showcases wide-plank wood-look porcelain flooring, painted tongue-and-groove ceilings, custom aluminum railings, and a dramatic four-story glass atrium staircase. The luxurious primary suite enjoys Gulf views, a private balcony, and a spa-inspired bath with a soaking tub, rain shower, dual vanities, and generous storage. Four additional ensuite guest bedrooms, each with private balconies and walk-in closets, provide exceptional comfort and privacy for family and guests. Designed for entertaining, the main living level features an open-concept great room with a custom fireplace, built-in dining, beverage bar, and a chef's kitchen appointed with custom cabinetry, granite countertops, GE Monogram appliances, a hidden coffee bar, oversized island, and banquet seating for ten. The adjoining Gulf-view terrace offers a fully equipped outdoor kitchen, creating the perfect setting for seamless indoor-outdoor living. Crowning the home is an extraordinary 950-square-foot rooftop terrace showcasing panoramic Gulf views and front-row seats to Siesta Key's legendary sunsets, where the ever-changing sky erupts in vibrant hues reflected across the Gulf waters. Complete with a full outdoor kitchen, beverage cooler, ice maker, automated louvered pergola, and powder bath, it is the ultimate venue for entertaining, enjoying sunset cocktails, or relaxing beneath the stars above the coastline. Additional highlights include a four-zone HVAC system, elevator service to every level including the rooftop, abundant secure storage, smart home prewiring with security cameras, low-maintenance tropical landscaping with irrigation and lighting, and superior concrete and masonry construction with a hollow-core concrete roof system and hurricane-rated impact glass, delivering exceptional durability, energy efficiency, and peace of mind. This is a rare opportunity to own a true luxury beach retreat that combines world-class construction, spectacular Gulf views, dramatic nightly sunsets painted across the Gulf sky, and an unbeatable location just steps from Siesta Beach and all the shopping, dining, and entertainment of Siesta Village.

10/16/2026

Due tomorrow’s anticipated stormy weather, the open house at 5547 Avenida Del Mare has been rescheduled for October 24th!

Address

2000 Webber Street
Sarasota, FL
34239

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