Dean & DeWitt Property Management Reviews

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Dean & DeWitt Property Management

Dean & DeWitt Property Management, 2852 20th Ave N, St. Petersburg, FL 33713

4.4 160 verified reviews

Specializes in managing rental properties in Pinellas County (St. Petersburg area) with a department-style approach for leasing, maintenance, and accounting; offers an owner portal and 24/7 maintenance support, handling apartments, condos, and single-family homes.

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Landlord vs. tenant ratings

Landlord Rating
4.2 / 5
from 10 owners
Tenant Rating
4.4 / 5
from 150 tenants
High confidence · 10 landlord reviews

Landlord Rating reflects how property owners rate this manager; Tenant Rating reflects how renters rate them. Both are 1–5 star ratings built from verified Google & Yelp reviews, weighted toward recent reviews.

Photos

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Rating breakdown

5 star
215
4 star
11
3 star
2
2 star
3
1 star
32

Based on 263 rated reviews from the last 3 years.

Dean & DeWitt Property Management reviews

5.0★Mar 2026

This is my first experience with D&D because I’ve always used Realtors. Extremely delighted with Property Leasing Agent Bert N. He has made this entire lifestyle change very simple due to his exceptional customer service skills by addressing my concerns and responding in a timely manner. As we transition to the next phase of moving into my new place. Hope the rest of the D&D staff [property mgr team] will be as wonderful to work with as he was.

2.0★Feb 2026

My Dean & DeWitt experience has been mixed. I feel the agent prior to my moving in poorly represented the property owner by being inconsiderate. I expected to pay the first month's rent in advance of moving in. If you miss an early online payment date, you may have to physically pay in the office with a cashier's check or money order(s). I'm a busy professional. My agent silently let that deadline pass. Then, he both texted and emailed me to inform me that I'd missed the deadline. Almost as if he were waiting to do that. Yes, I was late. I own that. A text reminder would have been courteous.…

5.0★Feb 2026

Our company has done work with Dean & Dewitt and our experience with them has always been great, in large part due to Paula. She is extremely responsive and on the ball. She genuinely cares about taking care of issues both the tenants and owner in mind. Highly recommend this company!

5.0★Feb 2026

As a property owner, working with Dean & Dewitt has always been fantastic. I want to especially thank Paula for being on top of things for me. She gives me peace of mind that my property, the tenants and my needs are all considered. Thank you Paula!

5.0★Feb 2025

As a homeowner using Dean & Dewitt for my property management, they've taken care over everything so far and I have not needed to lift a finger to manage my home which has been a great relief. I've been working with Olga as my property manager and she's been very attentive and communicative which I greatly appreciate.

5.0★Feb 2025

It’s been a great experience working with Dean & DeWitt and with Olga Shahan as my property manager. Right from the beginning of my new contract, it was clear that she genuinely cares about her clients and takes immense pride in her work. She was always available to answer my questions, no matter how big or small, and her communication was consistently clear, timely, and professional.

5.0★Feb 2025

Dean and Dewitt’s biggest asset is their team. I’m very happy to be working with Olga during this year. I couldn’t have a more attentive, responsive, and thoughtful person to work with for my rental. She works very hard to ensure the best outcome for all sides and clearly communicates what can be expected, next steps, and options. I give this assessment as someone that has had her supporting a move-in, hurricane prep and damage, and maintenance concerns that have arose. It’s been a pleasure to have her an my point of contact and look very happy to be continuing with her.

1.0★Nov 2024

Live in Boston. Looked for the best ratings on a property management company in St Petersburg to rent my condo. Went down there to see my place I was horrified and crying. This company took my money and did the worst repairs ever. I spent close to 3000. to do anything needed and gave the money willingly and I trusted they were doing the right thing. I would not or would ever recommend them. Yes Justin Dewitt refunded me close to 400.00 not even close to the money I put out. I run a company. Because someone is no longer working for you still reflects on your company. You treated me with disres…

1.0★Oct 2024

I'm two months into having this company as my property manager and I can't tell you how displeased I am with them. If I could give zero stars, I would. They do absolutely nothing. More to come as my year long grueling contract continues with them.

5.0★Jul 2024

i’ve used Dean and Dewitt to manage my rental property for seven years, and have had nothing but great experiences with them. I haven’t had to do anything myself, really. They provide a worry-free, stress free service. I very grateful for them.