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BEST RATED GAINESVILLE, FL INSURANCE AGENTS

3 Best Insurance Agents in Gainesville, FL

Expert-recommended Top 3 Insurance Agency in Gainesville, Florida. All of our insurance agents actually face a rigorous 50-Point Inspection, which includes customer reviews, history, complaints, ratings, satisfaction, trust, cost and general excellence. You deserve only the best!

Ken Castellani - Gainesville, FL Insurance Agents
Ken Castellani - Gainesville, FL Insurance Agents
Ken Castellani - Gainesville, FL Insurance Agents
Best Insurance Agents in Gainesville FL - Ken Castellani - GEICO video
7+ YEARS IN TBR
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KEN CASTELLANI

(4.9 Score)
GEICO 3080 Southwest Archer Road, Suite 10,
Gainesville, FL 32608 Directions

Since 2004

Specialty:

✓ Motorcycle Insurance ✓ ATV Insurance ✓ Umbrella ✓ Homeowners ✓ Renters ✓ Condo ✓ RV Insurance ✓ Life ✓ Boat ✓ Personal Watercraft ✓ Overseas ✓ Travel ✓ Commercial Auto ✓ Business Insurance ✓ Flood Insurance ✓ Mobile Home ✓ Identity Protection ✓ Snowmobile ✓ Collector Car ✓ Mexico Car ✓ Pet ✓ Mobile Device Protection ✓ Jewelry Insurance ✓ Medical Malpractice ✓ Earthquake Insurance ✓ Event Insurance

"Ken Castellani has over 20 years of relevant experience in the insurance field. He provides sound, professional insurance advice. As your local agent, Ken is licensed to serve you in Florida. He has a complete understanding of GEICO's insurance products. He has worked with many insurance companies and is a top agent helping clients get the coverage and price they deserve. The team of staff continues to offer claims handling services to their customers via remote working. Ken Castellani specializes in a wide selection of insurance products and savings. Whether you are just starting and shopping for small business insurance or just looking for the rates or coverage, Geico offers the right insurance policy. Ken provides proper insurance for your needs and the personal service you deserve.

2026 Update: Ken Castellani has been involved in the Gainesville Art Festival, Micanopy Fall Harvest Festival, and the National Hot Rod Association (NHRA) Gatornationals."

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Discount:

23% Off Restraint Device

5% Off Anti-Lock Brakes

23% Off Anti-Theft System

3% Off Daytime Running Lights

15% Off New Vehicle

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Contact:

(352) 375-2886

Mon-Fri: 9am - 5pm
Sat & Sun: Closed

TBR® Inspection Report:

John Darr and Ray Schackow - Gainesville, FL Insurance Agents
John Darr and Ray Schackow - Gainesville, FL Insurance Agents
John Darr and Ray Schackow - Gainesville, FL Insurance Agents
Best Insurance Agents in Gainesville FL - John Darr and Ray Schackow - DARR SCHACKOW INSURANCE video
6+ YEARS IN TBR
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JOHN DARR AND RAY SCHACKOW

(4.8 Score)
DARR SCHACKOW INSURANCE
5200-B West Newberry Road,
Gainesville, FL 32607 Directions

Since 1992

Specialty:

✓ Homeowners Insurance ✓ Flood Insurance ✓ Renters Insurance ✓ Mobile Homes Insurance ✓ Auto Insurance ✓ Motorcycles Insurance ✓ Recreational Vehicles ✓ Watercraft Insurance ✓ Boats Insurance ✓ Umbrella Insurance ✓ Life Insurance ✓ Group Health Insurance ✓ Employee Benefits Insurance ✓ Workers Compensation Insurance ✓ Liquor-Based Business Insurance ✓ Construction Insurance ✓ Trucking Insurance ✓ Personal Insurance ✓ Commercial Insurance ✓ Commercial DSI Trucking Insurance

"John Darr and Ray Schackow serve both personal and business lines of insurance throughout Florida. Darr Schackow Insurance is licensed in 32 other states. Their team of expert insurance agents helps remove the stress of ensuring that businesses and families are properly covered. They provide individualized attention and superior customer service at exceptionally competitive rates. Their agents have owned trucks, freight brokerage companies, and permit businesses. They have over 34 years of experience handling almost every type of coverage and permit out there. They value people and are customer-focused. They operate with honesty and integrity, and through their extensive relationships with top-rated insurance carriers, their agents can find affordable coverage tailored to each client’s specific needs, lifestyle, and circumstances. In the end, you will feel educated about your insurance situation and confident that you've chosen the right policies for you. They also offer a free personal insurance quote.

2026 Update: Darr Schackow Insurance is owned by John Darr, Ray Schackow, and Richard Rowell. Their mission is to work diligently to decrease stress, provide great options, and offer affordable pricing for all clients."

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License #L08000109358

Contact:

(352) 338-0552 (888) 337-9322

Mon-Fri: 8:30am - 5pm
Sat & Sun: Closed

TBR® Inspection Report:

Tish Oleksy - Gainesville, FL Insurance Agents
Tish Oleksy - Gainesville, FL Insurance Agents
Best Insurance Agents in Gainesville FL - Tish Oleksy - STATE FARM video
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TISH OLEKSY

(4.8 Score)
STATE FARM 6021 NW 1st Place,
Gainesville, FL 32607 Directions

Since 1990

Specialty:

✓ Auto Insurance ✓ Motorcycle Insurance ✓ Homeowners Insurance ✓ Condo Insurance ✓ Renters Insurance ✓ Business Insurance ✓ Life Insurance ✓ Investments ✓ Rec Vehicles ✓ Boat Insurance ✓ Pet Insurance

“2026 Update: Tish Oleksy has more than 38 years of experience with State Farm. She has proudly served Gainesville in the surrounding area since 1990. The team assists customers throughout Florida, from Key West to Pensacola. Tish is an active member of the Gainesville Chamber of Commerce and enjoys supporting the Bread of the Mighty Food Pantry, reflecting her strong commitment to the local community. If you’re buying a home, renting, growing your family, or opening a business, Tish Oleksy offers a free auto insurance quote, homeowners insurance quote, renters insurance quote, life insurance quote, or business insurance quote. She helps limit losses from life’s unexpected events and builds relationships that support long-term financial security by providing clear information and personalized service.”

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License #FL-L004456

Contact:

(352) 336-8474

Mon-Thu: 9am - 6pm
Fri: 9am - 5pm
Sat: 10am - 3pm
Sun: Closed

TBR® Inspection Report:

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KEN CASTELLANI REVIEWS

I had the pleasure of having Hannah has my agent to ensure that I receive the best quote. But I had so difficulties throughout this process. Hannah hung in there with me. She stayed on the case via phone calls and emails. The day of the transaction, Hannah was not able to speak to me at the appoint time. One of her colleagues called me to inform me of the situation. And asked was another time good because she wanted to respect my time. So a big shout out to Hannah for closing the deal. Hannah was very helpful, informative and professional. Thank you Hannah you made this process so much easier!!!

Thank you, Nicole H. for your patience and time helping me get set up with my auto insurance. GEICO has been insuring our two boats for years and claim free. Very happy to be back with Geico for my auto policy too. My goal is to keep my safe driver on my driver’s license. Thanks again Nicole and Brent!

Zach O’Friel was fantastic! He made setting up my policy quick and easy, and took the time to walk me through getting the app up and running on my phone. Great service and support every step of the way!

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JOHN DARR AND RAY SCHACKOW REVIEWS

Heather Mcculley with Darr Schackow made the world of insurance a positive and easy experience for me when I bought my first home a few years ago! I have had the pleasure of working with her for my homeowner's and now car insurance. She is quick in her response time, accessible to answer questions and knowledgeable in her filed. I have referred several of my friends and family and we are all happy campers! Thanks Heather!"

Suzanne Cutsy was great. I had a hard time finding Insurance for mt mothers house. She worked with us to find us a great deal and in a timely manor. She is easy to talk to and always available or calls back promptly. Highly Recommended!!

Marisa Wysocki provided excellent customer service. She helped me with details that my current insurance agent never provided. She was able to connect me with her contact within FMC and resolved our issue in a day. Thank you Marisa!"

TISH OLEKSY REVIEWS

We need insurance for our homes and property and I value this team to make sure that when I NEED IT I’ll be covered and they will be there to make sure I’m taken care of. If I call to update my insurance or ask questions, I get answers. I’ve been insured by State Farm since my first car - 44 years ago. I’m with them because my grandfather insured his farm with them, my parents were insured with them and much of my family shares this pattern of loyalty. I’ve never had a major claim but over the years I have had claims and I appreciate the stress free resolutions. So, when I just added a new car to my policy I welcomed being able to talk to a person and get it taken care of quickly.

She was the most helpful person I have ever talked with on the phone. She went so above the average agent. She was super happy go lucky bubbly person. I DO give her 100 stars

Excellent Customer Service!! This State Farm Team is AMAZING. They always answer any concerns I may have with no hesitation while providing great customer service.

TBR® Inspection Score Report

KEN CASTELLANI Total Inspection Points: 118/120
Acknowledgments: 9
Complete Info: 9
Contact Info: 10
Current Evaluation: 10
Exact Services: 10
Experience: 10
Legitimate Ratings: 10
Location Proximity: 10
Review Analysis: 10
Reviews Accuracy of : 10
Video: 10
Website Standard: 10

TBR® Inspection Score Report

JOHN DARR AND RAY SCHACKOW Total Inspection Points: 116/120
Complete Info: 9
License: 9
Reviews Study: 9
Website Standard: 9
Business Images: 10
Contact Info: 10
Current Evaluation: 10
Exact Services: 10
Legitimate Ratings: 10
Location Proximity: 10
Reviews Accuracy of : 10
Website Source: 10

TBR® Inspection Score Report

TISH OLEKSY Total Inspection Points: 115/120
Business Images: 8
Acknowledgments: 9
Complete Info: 9
Reviews Study: 9
Contact Info: 10
License: 10
Exact Services: 10
Experience: 10
Legitimate Ratings: 10
Location Proximity: 10
Reviews Accuracy of : 10
Website Standard: 10