Top Agents Tell All: How I Sold the Craziest House of My Career

“There’s a buyer for every house, we just have to define who that buyer is, and what’s going to be the best use of the property,” says top Orlando-area real estate agent Jennifer Wemert. With her expertise in foreclosures and investment properties, she’s seen her fair share of “unique” homes.

HomeLight spoke to three experienced agents from across the country about how they sold the craziest, out-the-box homes of their career — one with a checkered past, one with a rock in the living room, and one with four families living in it at once. May their stories offer hope and inspiration that you, too, can sell a home no matter how unmarketable it seems, so long as you have the right real estate agent in your corner.

House #1: A rocky transaction

The home might not have Craig Chastain’s worst property, but it was certainly his weirdest — and for the San Bernardino, California area agent with over 500 transactions under his belt, that’s saying something.

“I sold a house with rock right in the middle of it, like actually coming up from the ground,” Chastain recalls. “It was actually a house built around a rock, I guess you could say.”

The first reaction to the rock in the living room was to remove it, but that was a cost-prohibitive option. “It was about the size of a Volkswagen bug — it was big,” Chastain says. It seems even though the property was large, some of the acreage wasn’t usable for building. So, having a rock in the living room was the (only?) if not the ideal solution when the property was constructed.

How the agent sold it:

Due to the rock’s size and odd placement, Chastain knew it would play a prominent feature in this real estate listing. He didn’t want to avoid the “rock” in the room, or mislead buyers before they visited the property, and he made sure the professional photos were top quality. “[The rock] was in all the listing photos. A buyer was made well-aware before visiting the home,” Chastain says.

Chastain found that being open about the rock actually drew in some potential buyers: “Their first reaction is, ‘Oh, that’s kind of cool,’ but then it’s like, well, do I really want that in my house?’” Anticipating buyers’ reactions, Chastain worked with the seller to discount the property between 2%-3% to account for the odd feature.

Key takeaway: Don’t hide a home’s flaws — focus on its redeeming qualities.

Being open about the property’s shortcomings and adding a slight discount to the property accelerated the sale of this unique home. But the key to the formula was “highlighting all the other features and benefits outside of that negative,” says Chastain. “So we focused on the area, the schools, the positives.”

For many buyers, it’s not just about the home, but the neighborhood surrounding it. Sure a well-lit kitchen and perfectly groomed yard are going to help a sale, but so too can a dream neighborhood. According to a survey conducted by ImproveNet, buyers consider proximity to grocery stores, parking space, and a strong public school system top priority when buying a home.

So, include colorful descriptions of your area in the listing and how far your home is from attractions buyers might prioritize. That way, the “unique” feature about your home — if it’s not obviously desirable — becomes someone’s way into an amazing neighborhood… at a bargain!

House #2: A pack-rat’s paradise

“I walk into every home, not judging it based on what it looks like now, but judging it for what it can be,” says Charlie Brown, a top-selling agent in Fort Worth, Texas. But, after 900 real estate transactions, even he was challenged by a particularly “unique” house.

“We had four sets of adult siblings living in one home with their families. The home was literally a zoo. They had sheets as curtains and living rooms and things trying to block off everything,” says Brown. The spaces were divided and nearly unnavigable with the amount of stuff the families had accumulated. The sellers were willing to get the property into selling condition so they could fetch top dollar rather than sell “as is.” However, the family couldn’t afford all of the required updates.

How the agent sold it:

This wasn’t Brown’s first “extreme decluttering” challenge. And he frequently works with clients who might not have cash on hand to whip their house into selling shape. For these distressed properties, “We will fund the repairs, whether it be $5,000 or $10,000, and add a small upcharge on the commission. We find that they make it back because the condition of the home is much nicer,” Brown explains.

Through relationships with vendors, Brown and his team of agents contracted professionals to do the work. The vendors, in these types of cases, agree to get reimbursed through the proceeds at closing, which makes budgeting for the necessary repairs much easier for a seller.

Brown’s biggest piece of advice for selling a home with hoarder vibes? “The [sellers] vacated the house and that was truly the only way they could declutter it,” he recalls. The sellers had another place to stay while preparing their home, making it easier for them to just clear everything out that was left on their property.

Key Takeaway: Be ready to do the prep work.

If you want to sell your home on the open market, but it’s in bad condition, you should be willing to do some work on your end to clear it out. Being able to stay somewhere else while taking care of decluttering can accelerate the process and put a little distance between you and your possessions.

Clearing out your home can make all the difference, but so can the right real estate agent. Find an agent in your area with experience selling a distressed or cluttered home — they could have the connections and expertise to turn your property from seller’s nightmare to a buyer’s dream.

House #3: Historic home with a checkered past

Back to Wemert, the Orlando agent experienced in foreclosures and investment properties. She was tasked with selling a seven-bedroom home in downtown Kissimmee, Florida. Sounds like an easy task, right? Old homes are charming, with lots of character! Well, there was a catch. Or several of them, if you will.

Wemert describes inside the home where there were “exterior locks on the bedroom doors and mattresses in every bedroom, just lying on the floor. I think it was a previous brothel, it was pretty creepy,” Wemert recalls. “I thought to myself, ‘How in the world are we ever going to sell this?’” Beyond its seedy past, the property didn’t make sense for a traditional buyer. Who could make use of a home configured like that?

How the agent sold it:

Wemert knew the property as it was wouldn’t appeal to traditional buyers. But, with an understanding of her market, she knew what direction to take it in. Because of its proximity to Orlando-area attractions, the property would appeal to investors who sought short-term rental properties.

After cleaning it up and, ahem, dousing it in bleach, so to speak, Wemert decided to “frame it as a perfect Airbnb property with seven bedrooms to rent out and return the investment with small upgrades on the property.” Since the rise of Airbnb and similar booking sites, Wemert has been able to market some of her more unique listings to beginners searching for investment properties.

Key takeaway: If you have a unique property, show buyers how it ought to be used.

Not every home will be ideal as a primary residence. Maybe more people will be attracted to it as a vacation destination or rental property. Make sure your staging and marketing reflects how buyers are likely to use it, whether that’s through modern coastal staging techniques or pulling local rent trends so people can see its full potential.

Header Image Source: (Travis Grossen / Unsplash)