Mark Podolsky hated being an investment banker. “When a buddy said he was buying raw land for pennies and flipping it for a lot of money, I told him I didn’t believe him,” he says. Then he grabbed three grand he’d saved for car repairs and tagged along to a court sale in Deming, NM, “and did exactly what he told me to do.”

Podolsky bought 10 half-acre parcels for around $300 apiece, then promptly sold each for $1,200. He told his wife he wanted to quit his job to flip land; she said absolutely not. “It took 18 months for my land income to exceed my banking income. I quit in 2002,” he says. Since then, he has flipped 6,000 parcels and founded The Land Geek to guide others.

Land is cheap—but may not pay off easily

Podalsky’s approach is simple: Sift through public records for land owners who are behind on property taxes and make them a dirt-cheap offer. He then turns around and contacts the owner’s neighbor. “I’ll send a letter: ‘Here’s your opportunity to protect your views and privacy.’ Often, the neighbor will buy it,” he says. If not, he lists the plot in Facebook groups, on Land.com, or on his own site, wholesale.thelandgeek.com.

Although quick house flips can pan out, land is often a long game. “It takes patience because, unlike a rental property, it doesn’t produce immediate income unless you develop or lease it,” says Lauren Byington, who has purchased land in Texas and Missouri and increased the value through upgrades like a barn and RV hookups. “I could lease my land for hunting, but I love animals, so that’s not happening.”

In rare instances, land can rise in value. “In Texas, large tracts are being acquired for data centers and solar farms,” Byington says. “That makes it imperative that buyers research future development plans. Homes are more predictable, but land has more upside potential.”

Ownership doesn’t mean you can build whatever you want

Zoning will dictate what you can build or farm, how far down you can dig for water, and more. “In drought-laden Texas, you don’t have carte blanche to dig a well,” Byington warns. “Wells have run dry here, and I’ve seen neighbors paying to get water carted in. We hold our breath hoping that’s not us soon.”

Other rookie mistakes include purchasing landlocked parcels with no road access, not understanding deed restrictions, and assuming utilities and septic will be available and “easy” when they’re anything but. Her advice? Read the fine print. “When I was buying my first property, the seller attempted to include an addendum reserving the mineral rights, which can be extremely valuable in Texas,” Byington says. “Fortunately, I caught it, but many buyers don’t.”

The land may be the least of your costs

California investor Josh Justiniano learned just how expensive “cheap” land could be after building a duplex on a parcel in Bakersfield, CA. Before he was issued a certificate of occupancy, he had to spend around $40k on permits, fees, and building sidewalks. “The sidewalks cost $10,000 that we didn’t see coming,” he says. Lesson learned: “Talk to city planning and ask about off-site requirements like fire hydrants, gutters, or other infrastructure before you close, not after.”

All that said, Podolsky points out, “There isn’t a piece of land where someone can’t do something on it, even if it’s not obvious. I had a buddy who bought a mud pit. At first, I thought, ‘What a disappointment.’ Sure enough, someone rented it to drive around in his ATV. I’ve seen people buy swampland to grow shiitake mushrooms. I once mistakenly bought the side of a mountain for $2,500. A film director bought it off eBay for $32,500 so he could film there.”

And even if land owners don’t do or build anything at all, they dream that someday, they or someone in their family will: “People buy land to say ‘I own this part of the world.’”

New York City Mayor Zohran Mamdani froze rent on 1 million apartments. But his former home in Queens just got a 30% rent hike. Here’s why.

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Housing is one of the most talked-about topics ahead of the midterms, and although affordability may seem more out of reach than ever, history suggests that at least some progress has been made. According to an analysis by Realtor.com, homeownership took off after WWII, has fluctuated since the 1980s, but is currently holding steady at 65%. Here’s a timeline of the housing policies that helped make that happen.

1934: The National Housing Act helped create the modern mortgage during the Great Depression, lowering down payments from 30–50% to 10% and extending repayment periods for short-term loans to 20–30 years.

1944: The GI Bill backed more than 2 million veteran home loans, boosting homeownership from 44% in 1940 to 62% in 1960—the biggest surge in US history.

1968: The Fair Housing Act banned housing discrimination, expanding credit access for minority communities and helping to push homeownership levels higher through 1980, though the effects of redlining continued for decades.

2008: The Housing and Economic Recovery Act placed Fannie Mae and Freddie Mac—then publicly traded government-sponsored enterprises—under government conservatorship, an intervention deemed necessary to keep the American mortgage market from imploding.

2026: The 21st Century Road to Housing Act—passed by Congress and still stuck in limbo awaiting the president’s signature—aims to reduce regulatory gridlock and get America building more homes. But even if Trump signs, it could take years before we notice a difference. Here’s more on how government policies have impacted homebuying throughout history.

Got a question about real estate? Ask it here, and we’ll answer it in a future issue.

Most homes have some history, but 300 years’ worth is packed into The Grange: a Rhode Island home built in 1723 that’s currently listed for $2,985,000. Ben Franklin’s sister crashed at this 11-acre riverfront property, as well as Revolutionary War General Marquis de Lafayette and Civil War General Ambrose Burnside. Here’s more from its current owner, Dean deTonnancourt, who is also the listing agent at the aptly named REMAX Revolution.

Q: How did you end up buying this property? “We purchased The Grange in 2020. Our prior residence was also historically significant, and we are drawn to the details and character found only in older homes. For someone who appreciates history, it feels less like ownership and more like becoming a steward of history. You’re preserving it for future generations and placing your stamp within that history.”

Q: What are the challenges? “Historic homes are older and require ongoing proactive maintenance. Deferred maintenance can quickly become expensive. Addressing small issues before they become large ones is one of the best investments you can make.”

Q: Are historic homes good investments? “Historic homes often hold value beyond traditional real estate metrics. Truly unique properties are hard to find, and that uniqueness becomes their greatest long-term value.”

Q: What advice would you have for buying historic homes? “Understand the property’s maintenance needs, and whether it’s listed on a local or national historic register. Each will provide a guidebook that helps ensure improvements and restoration are completed in a manner that preserves the property’s historic character.”

Q: What surprised you most about living here? “You don’t simply live in a home like The Grange; you become part of its continuing story. Preserving something that has stood for generations comes with a tremendous sense of responsibility. Know that your time with The Grange is only one chapter in a much longer story.”

Click here to time-travel back to this Revolution-era home and see how it looks today.

India Hall backed into her first investment by turning her own home into a rental. Since then, she and her husband have made a business out of Washington, DC’s weak point: Many homes here haven’t been renovated in years.

Average home price: $581,881 (down 2.8% YoY according to Zillow)
Homes that sell over list price: 24.4%
Homes that sell under list price: 53.9%
Average rent: $2,497/month

How she got started: “I converted my primary residence into a rental and realized I could benefit from both monthly cash flow and property appreciation,” says Hall, founder and team leader with The Ultimate Team at HomeSmart. “When I left my corporate job and no longer had access to a 401(k), I began investing more intentionally. Real estate became my retirement plan.”

Her market’s pros: “It’s a great time to purchase because inventory is increasing, homes are sitting on the market longer, and sellers are willing to negotiate,” Hall explains. Plus, “many DC homeowners haven’t renovated in years, which can create opportunities to buy below market value.”

Hall recently bought a row house in the Del Ray neighborhood of Alexandria, VA, for $485,000. “It started as a two-bedroom, one-bath home, and we spent $275,000 building a 20-foot rear addition and a five-foot front bump-out, converting it to a four-bedroom, 3.5-bath home that appraised for $1.25 million. Today, it’s a furnished corporate and short-term rental generating $6,000 to $8,000 per month.”

The cons: “Because properties are taking longer to sell, investors should plan to hold onto the properties long term,” she says. “Don’t assume every home is a quick flip.”

Her advice: “Buyers are price sensitive, so focus on areas that are affordable today but may not stay that way as revitalization happens around them,” Hall says. Some areas she’s watching: the former Six Flags site in Upper Marlboro, MD, and Oxon Hill, MD, where an MGM casino opened, and a proposed 6,000-seat mini-Sphere could bring more Vegas-style glitz, jobs, and residents to the area.

Got a home or housing market you want to highlight in The Playbook? Tell us more about it here, and we’ll consider featuring it in an upcoming issue.