She rented for years, bought land before she could afford the dream, and stayed for five decades. There's a lesson in that for every renter.
I loved Dolly Parton. Still do. The music, the humor, the heart—and a woman who understood that a little extra sparkle rarely hurts.
When she died in August at 80, I went down the tribute rabbit hole like everyone else. One video stuck with me. It skipped the stages and the awards and walked through her homes instead.
Video: Memory Itch on YouTube
There wasn't much glamour in it. What stayed with me was how each place matched a chapter of her life—and how long she lived like the rest of us before the housing caught up with the career.
It started with a rental
Dolly was born in 1946 in a one-room cabin her family rented in East Tennessee. She grew up one of twelve kids in a two-room cabin near Sevierville.
The day after high school graduation in 1964, she moved to Nashville. She met Carl Dean at a laundromat her first day in town. They married in 1966 and stayed married nearly 60 years, until Carl died in 2025.
The early married years were small rentals. Her face was on television, her name was on records, and she still went home to a place with somebody else's rules.
If that sounds familiar, you're in good company.
She bought before the dream was finished
In 1972—years before "9 to 5" made her a pop star—Dolly and Carl bought land in Brentwood, just outside Nashville. Carl, her brothers, and her uncle helped build the house.
She wrote later that the acreage was intentional. If she got as famous as she hoped, people would come looking, and she wanted a driveway long enough to keep strangers off the front porch.
That was home for more than 50 years.
She owned other places. A house on Glencliff Road in Nashville from 1980 to 1996, which sold for $140,000. A mountain cabin in Idyllwild, California, where she wrote songs, which she donated to Ronald McDonald House Charities of Southern California in 2023.
But she never traded up to prove anything. She bought what fit her life, held it, and let every other property serve a purpose.
In 1972, that land was just a purchase.
The meaning caught up later.
How homeownership became the expectation
Dolly grew up right in the middle of America's biggest housing shift. According to the Census Bureau, the national homeownership rate was 43.6% in 1940. By 1960 it hit 61.9%, fueled by postwar growth, new construction, and easier financing.
That's when buying a home got baked into our idea of adulthood: start a career, save, buy a starter home, trade up later.
Real life rarely follows that script. Being ready to settle somewhere and being financially ready to buy there are two different things. You can love your neighborhood, feel established in your work, and still need time to make the numbers fit.
That doesn't make you behind.
Chicago renters want in
70%
of Chicago renters say they'd rather own.
8.2%
of the renters tracked actually made the move between 2022 and 2025.
21% vs. 34%
Chicagoans under 35 who own, vs. the average across U.S. metros.
Source: Financial Health Network, Credit-Ready but Priced Out, 2026
The desire is there. What usually holds people back is preparation: credit, savings, and a clear picture of the real monthly cost.
And in Lakeshore East, preparation matters. Well-priced condos don't sit. The renters who get the home they want are the ones who did the homework before the right unit hit the market.
Your first purchase doesn't have to be your last
"Starter home" makes a first purchase sound like something you're supposed to outgrow. Dolly's first real purchase turned out to be her forever home.
I start with a different question: What would make this home a good fit for your life now—and for the years you expect to live there?
For someone looking at a condo in Lakeshore East, that might mean room to work from home, space for visiting family, or staying close to the routines and the lakefront you already love.
It might mean buying a smaller home in the location you want instead of stretching for extra square footage. Or it might mean renting a little longer while you set up a purchase that leaves you comfortable.
Renting to owning starts with clarity
You don't need to tour ten condos to find out if buying makes sense. Start with the real numbers.
The mortgage is only part of it. Property taxes, insurance, association assessments, mortgage insurance if it applies, maintenance, and utilities all go in the budget. Upfront, you need closing costs plus savings left over after you close.
For a condo, I also look at what the assessments cover, the association's reserves, upcoming building projects, and whether parking is sold separately.
Then the personal questions: How long do you expect to stay? How much flexibility do you need? What monthly cost still leaves room for the rest of your life?
A good first conversation leaves you better informed—even if you decide to renew your lease.
A home that fits your next chapter
Dolly could have bought a bigger house every time her career jumped. She didn't. She bought land early, built privacy, and stayed.
Room to begin. Somewhere to come back to. A place to gather the people you love. Those belong in the decision right next to price.
If you're renting in Lakeshore East and wondering about buying, let's talk. Real properties, real costs, and a timeline that's yours.
You don't need your whole future figured out to ask the first question.
Ginger Menne | Baird & Warner
Top Results. Local Focus. Lakeshore East.
[email protected] | (312) 216-5887
