Selling A Rental Property in Jupiter, Florida
You Thought Being a Landlord Would Be Passive Income. Instead, It's 2am Phone Calls, Late Rent Payments, and Constant Headaches.
Let me show you the numbers and help you decide if you should exit an investment property, without the stress.
You bought a rental property thinking it would be easy money. Or maybe you moved away from Jupiter and kept your old house as a rental. Maybe you bought a starter home, got married, upgraded, and thought renting out the first one made sense. Maybe you bought a second home here thinking you'd vacation in it often, then decided to rent it when you weren't using it. Or maybe you bought it specifically as an investment property, thinking the income would be worth it.
It hasn’t exactly worked out as planned.
Being a landlord isn't passive income, that’s a complete myth. It's active, frustrating, and often not even profitable when you look at the real numbers.
The tenant calls about every little issue. Or worse, they don't call, and you discover minor issues have turned into huge problems you never even knew about. They're late on rent for the month, it may not be the first time. Or they stopped paying altogether and now you're looking at eviction costs and lost income. The AC stops working, the roof started leaking, the toilet keeps overflowing, the hot water stopped being hot. Something always needs fixing, and you're managing it from a few towns, or a few states away. You’re trying to coordinate contractors you've never met, for a property you can't easily visit.
You're holding onto a 3.5% mortgage rate because everyone tells you "don't give up that rate!" But you're tired. You're frustrated. If we’re being honest, you're ready to be done with this.
This investment just isn't working anymore. And that's okay.
I help landlords throughout Jupiter and Palm Beach County sell rental properties and move on with their lives. Let me show you the real numbers once we properly calculate your income and expenses, and help you make the decision that actually makes sense for you.
When Being a Landlord Isn't What You Expected
For Many Landlords, Tenants Are the Problem
Maybe you got lucky at first and had a great tenant. Then they moved out and the next ones were a nightmare. Late payments. Excuses. Damage you didn't discover until they left. Constant complaints about things that didn’t really need fixing.
Maybe you have a truly hostile tenant. Someone who won't let you show the property, won't cooperate with inspections, threatens legal action over every minor issue. You're dealing with eviction attorneys, wondering how you ended up here, how much this will all cost, and when will it end.
And now you're scared. Because even if you get rid of this bad tenant, what if the next one is worse?
The Distance Makes Everything Harder
You don't live in Jupiter anymore, or maybe you never did. Managing a rental property from across the state, or across the country, can be exponentially difficult, much harder than you thought it would be.
When the tenant calls about a plumbing issue, you're trying to find a plumber in an area you don't live in. You can't drive by to check on the property. You can't easily verify if repairs were actually done or if the contractor is charging you fairly. You're flying blind and paying for it.
The Income Isn't What You Expected
On paper, it looked great. Rent covers the mortgage, maybe even leaves a little extra. But then reality hits:
A month of vacancy between tenants
Repairs that weren't budgeted for
Property taxes going up
Insurance premiums rising (especially here in Florida)
When you actually add it all up, you're barely breaking even. Or worse, you're losing money every month.
Everyone Tells You Not to Sell
Your family says, "Real estate is always a good investment, hold onto it!"
Your friends say, "Don't give up that interest rate! Rates will never be that low again!"
Financial advisors say, "You're building equity, stay the course!"
But they're not the ones dealing with tenant calls at 2am. They're not the ones coordinating emergency repairs. They're not the ones stressed every month wondering if rent will arrive on time.
You are.
Let Me Show You the Real Numbers
Here's what most Landlords don't realize until I sit down with them and do the math:
Your property has probably gained significant equity if it’s located in Palm Beach County and you purchased before Covid.
That equity is trapped. It's sitting in a property that's causing you stress, and possibly not generating the income you thought it would.
There's a better move. Sell the property. Cash out the equity. Take that money and put it to work somewhere else, somewhere that doesn't call you at 2am. Something that doesn't require you to coordinate contractors, something that actually generates the passive income you thought you were getting in the first place.
Yes, you'll give up your low interest rate. But if that low rate is attached to a property that's costing you money, time, and stress every month, what are you really giving up?
I have a background in both commercial real estate and finance. I can evaluate your cash flow, and show you the real financial picture.
Most of the time, when we run the numbers together, landlords realize selling makes far more sense than continuing to hold. The "okay, let's sell it" feelings.
Let me show you your numbers. Then you decide.
How I Help Landlords Sell Rental Properties in Jupiter and Palm Beach County
I've sold properties many investment properties in the last 15 plus years. I understand the difficulties of selling a rental property, especially when there's a tenant involved, or when the owner lives out of state.
Let’s Start With an Honest Conversation
No pressure. No sales pitch. Just you and me talking about what you're dealing with.
You tell me about the property, the tenant, what you're making (or not making), and what’s making you think you may want to sell. Give me the full picture, including what your costs really are, and what you think the plan is for the property.
I'll show you the math. We'll look at your cash flow, your equity, and what selling would net you after all expenses. No fluff, just data and real numbers.
We'll Figure Out the Tenant Situation
If you have a good tenant on a lease: We can wait for the lease to end, then sell the property. This typically results in the highest sale price because we can show it to buyers without having to work around a Tenants schedule. It can be really hard to sell a property with a Tenant in place. Unless you have a multifamily property where the rules are a little different.
If you have a problematic tenant who's still paying: Same approach, wait for the lease to end. If they're paying rent, there's no eviction to deal with, so we ride out the Lease and plan for when they're gone.
If you have a hostile tenant who's not paying: I’ve worked with a number of experienced eviction attorneys in Palm Beach County. We'll get the eviction process started and handle things legally and efficiently. It's not fun, but I've done this before and I'll help you through it.
If you need to sell faster and can't wait: We can market to investors who will buy with the Tenant in place. You'll likely get a lower price (investors account for the hassle factor), but sometimes speed and relief are worth the discount.
We Will Assess the Property Condition and Plan the Sale
Once the tenant is out, I'll walk the property and assess condition. Most rental properties need some TLC after tenants move out. This typically ranges from painting, to basic repairs, to wear and tear. Tenants generally don't care for a property the way an owner would. I can just about guarantee, there’s almost always something that we will have to fix or freshen up.
I'll tell you honestly what repairs will return more than they cost and what you can skip. Sometimes spending $3,000 in cosmetic paint and minor fixes is what you really need to get the property sold for top dollar. Sometimes it's better to sell as-is and let the buyer handle it. We'll look at the numbers and you'll decide.
I'll Handle Everything While You Stay Where You Are
If you're out of state, I'll coordinate everything locally:
Contractor estimates and repairs if you choose to make them
Professional photography and marketing once it's ready
Showings and open houses
Inspection negotiations
Communication with title company and attorneys
You get regular updates, but you're not drowning in details. You can stay in your city, keep living your life, and trust that things are moving forward here in Jupiter.
We'll Get You to Closing and Get You Out
I will negotiate to get you the best possible terms. When inspection issues come up, I'll let you know what's reasonable to address and what's not. I'll manage the timeline and keep everything on track.
When it's time to close, you can often sign remotely. And then it's done.
No more tenant calls. No more repair coordination. No more wondering if rent will arrive on time. No more stress about what might break next.
You're out. You have your equity. You can move on.
Common Questions About Selling Rental Properties in Jupiter
Can I sell the property with a tenant in place?
Yes, but it's not ideal. Selling with a Tenant in place usually means selling to an investor, and investors account for the hassle factor in their offers. You'll likely get less than you would selling vacant. This assumes your home is a single family, townhome, or condo. Commercial Properties and Multifamily Properties are different and often having Tenants in place is preferred.
It's also difficult to show a property when there's an uncooperative tenant. They can refuse access, have a kitchen sink filled with dishes and laundry thrown on the floor all over the house, making the property consistently look unappealing to Buyers.. Most buyers want to see themselves living there, and that's hard with someone else's furniture and belongings everywhere.
If your tenant is cooperative, on a month-to-month lease, and the property is in good condition, selling with them in place can work. But usually, it's better to wait for the Lease to end and sell vacant. At least in my experience.
What if my tenant won't leave when the lease ends?
This is called a "holdover tenant," and it happens. If they won't vacate voluntarily, you'll need to file for eviction. I work with experienced eviction attorneys in Palm Beach County who handle this regularly. The process typically takes 3-4 weeks in Florida if it's straightforward (tenant simply won't leave vs. tenant fighting it).
It's not fun, but it's manageable. And once they're out, you can move forward with the sale.
What if my tenant is destroying the property?
Document everything. Take photos. If they're violating Lease terms, you may have grounds for eviction even before the Lease ends. This is a situation where you definitely want to work with an attorney so you can maximize your rights.
I've dealt with hostile tenants before. Once they're out, we'll assess damage and determine the best path forward. Keep in mind I’ve seen Tenants dump wet cement down drains, cover walls in motor oil, use the carpet as the toilet, it can get pretty bad. Depending on the amount of damage we will talk about whether making repairs before selling, or selling as is with reduced pricing is the best path to take.
Should I make repairs before selling, or sell the rental property as is?
It depends on the property's condition and what repairs cost versus what they will likely return. Most rental properties need basic work after a tenant moves out. Painting, deep cleaning, maybe some minor repairs, landscaping if applicable, these are all common.
If there are deferred maintenance issues (AC unit that does not work properly, aged roof, outdated appliances that don’t work correctly), we'll look at the numbers. Sometimes making those repairs increases your sale price more than they cost. Sometimes it's better to price the property lower and let the buyer handle it.
I'll walk the property with you, tell you what I'm seeing, and help you make decisions that will maximize your bottom line at the time of sale.
How long does it take to sell a rental property in Jupiter?
Once the property is vacant and ready to market, well-priced homes in Jupiter typically go under contract in 30-60 days and close 30-45 days after that. The number of days it will take to go into contract is going to vary by property type as well. Condo’s will take the longest to sell, townhomes next, with single family homes selling the fastest of the group. Assuming the price is in line with other actively listed properties.
The bigger variable is the Tenant situation. If you have a Tenant on a lease that doesn't end for 8 months, you're waiting that long before we can realistically start. If they're month to month, we can give notice and move much faster. If there's an eviction needed, add 3-4 weeks for that process.
After I understand your specific situation, I can give you a realistic timeline.
What are the tax implications of selling a rental property?
I am not a CPA, I strongly recommend talking to one before you sell. But generally:
You'll likely pay capital gains tax on the profit (difference between what you paid and what you sell for, minus improvements and selling costs)
You may have to recapture (pay back) depreciation if you've been taking depreciation deductions
There are ways to defer taxes (like a 1031 exchange into another investment property), but those have specific rules and timelines. Depending on the estimated sale price of the property this may not be a viable option. There are administrative costs that can outweigh tax benefits if the sale price is on the lower end.
Every situation is different. Talk to a tax professional who can advise based on your situation.
I'm losing money every month, but everyone says real estate is a good investment. Am I making a mistake by selling?
Real estate can be a good investment. But not every property is a good investment.
If your rental property is causing more aggravation and costing you more than the income it brings in. If managing it is taking too much of your time and energy. If you've had bad tenant experiences that make you dread the next one, holding onto it may not be the best idea for you.
The fact that it's appreciated in value is good news. That means you can sell, take your equity, and invest it somewhere that actually works for you.
Don't hold onto an investment just because "that's what you're supposed to do." Hold onto investments that make sense for you. If this one doesn't anymore, it's okay to let it go.
Can you help if I live out of state?
Absolutely. Many of the rental property owners I work with live elsewhere. That's often part of why being a landlord becomes so difficult.
I can coordinate with tenants (or eviction attorneys if needed), give you a report on the property condition, check in on contractors, handle showings, and keep you updated throughout the process.
You can sign documents remotely and often don't need to visit Jupiter at all during the sale process. I'll be your boots on the ground here while you stay wherever you are.
What if I owe more on the mortgage than the property is worth?
This is rare in Jupiter's if you owned for any period of time, especially those purchased before Covid have appreciated significantly. But if you're in this situation, you have a few options:
Bring cash to closing to cover the difference. Not feasible for everyone.
Negotiate a short sale with your lender (they agree to accept less than you owe)
Keep the property and wait for values to increase, while working on cutting expenses and increasing cash flow if possible
This is a complex situation that needs careful analysis. If you think you might be underwater, let's have a conversation about what may make sense to do.
How do I know if selling is the right decision?
We'll look at the numbers together:
What's your property worth now?
What do you owe on it?
What are your monthly costs (mortgage, taxes, insurance, HOA, maintenance)?
What's your actual rental income after vacancy and expenses?
What's your equity position?
What could you do with that equity if it wasn't tied up in this property?
Then we'll talk about the non-financial factors:
How much time does this property consume?
How much stress does it cause?
How many more years do you want to be a landlord?
What would your life look like without this responsibility?
After we look at both the numbers and the quality-of-life factors, the right decision usually becomes clear. Most landlords I work with already know they want to sell—they just need someone to show them that it makes financial sense too.
Let's Look at Your Numbers
No pressure. No obligation. Just an honest conversation about your situation and what your options are.
I'll show you what your property is worth, what your equity position looks like, and what selling would actually net you. Then you'll have the information you need to make the decision that's right for you.
Fill out the form below and I'll call you within 24 hours to discuss your rental property. Or if you'd rather talk now, call me directly at (786) 443-7203.
Casey Prindle, PA
Licensed Florida Realtor
Serving Jupiter and Palm Beach County Since 2009
Background in Finance & Commercial Real Estate
Specialized Experience Helping Landlords Exit Rental Properties
Being a landlord isn't for everyone. If it's not working for you anymore, let me help you move on.