Table of contents
Table of contents

*Quote takes 1 minute, no credit pull


*1 quote from 40+ carriers


*New listings daily

Table of contents
Table of contents

Best Caroline county property management companies

Image of townhomes in Caroline County Maryland MD

Below you will find a list of top rated property management companies Caroline county. Identifying the top property management firm in Caroline county will take research. Make sure to talk to company representatives, interview them with the questions we provide below and read reviews. This process is paramount in identifying the best firm that will address all of your landlord needs and justify their monthly fees while keeping your tenants happy.

Skipjack Solutions

SkipJack Solutions Logo

Description: We’re local and we’re reliable. We can be there so you don’t have to, whether that’s to deal with the mundane and routine or the complete remodel. Our taskmasters have an acute attention to detail and a network of service providers to address with any issue. It’s handled. That’s all there is to it. Let our team of professionals take the stresses out of your short-term rental or AirBnB listing. We can navigate through the cumbersome license application process and prepare your space for rentals. After developing a checklist of necessary items, we will clean, shop and ready the house for new guests. With our specialized services, we make it easy to get more rentals with less effort so that your property can be monetized toward your long-term goals. We routinely receive high reviews (SuperHost status), which in turn generates more bookings. In most cases, we are nearby and available to greet guests, show them the features of the property and, if problems should arise, and guests have questions or needs, we can respond. Skipjack Solutions can help to relieve some of the burden and worry of ownership of a second home or property: from everyday coordination of grounds and house maintenance to seasonal projects and improvements. We handle the day-to-day operations or we have options to be on standby for occasional needs and unexpected issues. We have a stable of reliable vendors on call to address any concerns and provide peace of mind. We will ensure all is well on the home front! You can avoid potentially disastrous situations and ensure peace of mind. Priceless!


Google Rating: 5.0

Google Reviews: 6

Phone: (443) 362-8083

Address: 109 Green St, St Michaels, MD 21663

Property Management Monthly Fee: Contact to find out

Leasing fee: Contact to find out

Lease renewal fee: Contact to find out

Home Advantage Property Management

Home Advantage Property Management Logo

Description: Home Advantage Property Management is a family-owned full-service property management company specializing in residential rental property and apartment building management in the greater Baltimore/Annapolis area. Our goal is to take the headaches of being a landlord off of your shoulders by handling all the day-to-day chores that come with being a professional landlord, while ensuring that you get the best possible return on your investment.


Google Rating: 4.3

Google Reviews: 19

Phone: (410) 626-7411

Address: 1052 Lido Drive, Annapolis MD, 21409

Property Management Monthly Fee: 8%

Leasing fee: Contact to find out

Lease renewal fee: None

Important factors to consider

When evaluating a property manager there are several important factors that you need to consider other than their monthly fees to make a good decision. While monthly fees are important, renewal fees and leasing fees are a key consideration, sometimes other services property managers provide might be well worth above average fees. Consider reviews and what others have to say about about their experience with each property manager before moving forward and signing a contract. Do your research!

Here are additional factors that you should take into the account:

  • Staff on call and available 24/7 in Caroline county

  • How quickly they address maintenance issues

  • Do they have an extensive list of contractors in Caroline county

  • Do they have a large team of professionals in Caroline country to server as back ups

  • How many years of experience do they have in Caroline county, managing rental in different locations sometimes calls for additional skills

  • Do they have a competitive rate for Caroline county? If their rate is higher what justifies that? If its lower, is it because they lost clients and need to discount their service?

  • Are they locally operated in Caroline county? Proximity to your rental property is key to providing best property management service.

  • Do they collect rent in person in Caroline county or do they have more sophisticated tool to handle rent collection?

  • Why tenant services do they provide?

  • Are there other top property management companies Caroline county?

  • Will they find tenants Caroline county?

  • Will they post house listing Caroline county?

  • Will they evict tenant Caroline county?

  • Do they have good testimonials from other landlords Caroline county?

  • Will they quickly find tenants Caroline county?

  • Do they have decades of experience Caroline county?

  • Do they have access to best contractors Caroline county?

  • Do you feel comfortable entrusting you investment property Caroline county to this property management company Caroline county after having an interview with them?

Questions to ask a potential property manager

Below you will find a list of interview questions you must ask a potential property management firm before agreeing to hire them to manage your property. These questions will help you identify a good firm and set expectations from day one. Make sure to note their responses so you have an easy way to compare between candidate firms that you interview. Remember you are the client, they will manage and represent you to your tenant, this is a key to being a successful landlord, so no questions are off limits to help you figure which company is the right fit. If any of the responses rub you the wrong way, make sure to note that down and always go with your gut feeling. If something is wrong in this early stage, then its more than likely additional problem will follow, especially when you are not in the room and the firm engages with your tenant directly. Imagine loosing a long term tenant because property management firm didn't do a good job maintaining your property, this is a scenario these questions will help you avoid. Best property management companies Caroline county should have easy time giving you solid answers for below questions.

  1. What is your monthly property management fee?

  2. What is the leasing fee?

  3. What is lease renewal fee?

  4. Do you have a point of contact who is available 24/7?

  5. Do you have a back-up contact in case the first contact is not available?

  6. Do you provide any warranties, such as tenant durations warranties?

  7. Do you provide any warranties on how quickly you can find a tenant for my rental?

  8. Do you handle all types of rental maintenance issues?

  9. How many rentals do you manage in Caroline county?

  10. What have I not asked you that I should know about? (this is a great open ended question that might reveal more about the company that you didn't anticipate)

  11. Why should I choose you over other best property management companies Caroline county? (this is another great open ended question that might reveal more about the company that you didn't anticipate)

Can landlords sell properties with tenants in place?

Landlords often believe that they have to vacate their property and stage it to get top dollar for their portfolio rental. OfferMarket exists to dispels this notion. Everyday tired landlords or busy landlords post their rental properties with tenants in place on our free and open real estate marketplace to see if another rental investor would give them an offer for their rental.

OfferMarket specializes in augmentation of rental portfolios, ether through disposition of outlier properties or through acquisition of attractive rental with tenants already in place. If you want to test the market and see if you get offers on your rental with tenants in place, create a free listing and see if other landlords would offer you an even higher price than the market since you already have tenants in place and they would have to do less work to make it cashflowing. On the other hand, if you are looking for cash flowing properties, checkout our map to see if there are any rental properties that might catch your eye, feel free to talk directly to the seller, schedule a tour or submit an offer, completely free and without any obligations. OfferMarket exists to help Maryland landlords buy and sell properties, commissions free, with ease and expediency.

Checkout our listings on our map or create a free listing to test the market