Where Should You Live in Pensacola? Play Would You Rather and Find Out

Which Pensacola area is right for you?
It comes down to what you trade away. Beach access means a smaller house in Gulf Breeze, Perdido Key or Navarre. More square footage and land means Pace, Milton, Beulah or Cantonment. Walkability means East Hill, North Hill or Downtown Pensacola.

We play Would You Rather at dinner most nights at my house. Usually it's stuff like "would you rather have toes for fingers or fingers for toes," because we're weird like that.

But here's the thing. The grown-up version of that game is exactly how I figure out where someone should live. So let's play, Pensacola style.

Grab something to write with. Every time I name an area that matches your answer, put a tally mark next to it. By the end you'll see your pattern.

I'm Christina Leavenworth, a local realtor, and this is how these conversations actually go.

Round 1: Five minutes from the beach, or a bigger house 30 minutes out?

One, two, three, pick.

If you said five minutes from the beach: look at Gulf Breeze, which sits right between Navarre Beach and Pensacola Beach. Also Navarre, Perdido Key, and Innerarity Point. There are plenty of neighborhoods near Perdido Key that are surprisingly affordable and still put you 5 or 10 minutes from the sand.

Not everybody can buy directly on the beach. But you can absolutely get the beach lifestyle without the beachfront price tag.

If you said bigger house, 30 minutes out: Milton, Pace, Beulah, and Cantonment. More square footage for the money, near major roads and grocery stores, and roughly half an hour to the water. Go further north toward Jay or Molino and that drive gets longer.

Be honest with yourself here though. If it's 30 minutes each way, you're probably not going to the beach three times a week. That's an hour round trip plus packing a lunch. It becomes an outing instead of a habit.

Round 2: Character and nooks, or open and modern?

Character galore: East Hill, North Hill, Downtown Pensacola, Scenic Heights, and Cordova Park. These are where the older homes with real stories live.

Fun fact while you're thinking about it. Pensacola is the oldest city in America. People argue with me about this constantly and bring up St. Augustine. Here's the distinction: Tristán de Luna founded Pensacola first, but a hurricane wiped out the settlement and people scattered. So we're first founded, St. Augustine is first continuously established. Either way, it means we've got genuinely old housing stock with a lot of personality.

Open, modern, big closets, three-car garage: Beulah, which is right by the interstate, plus Pace and Milton where new developments keep going up. Gulf Breeze has new construction too.

When I say new, I mean built after 2005. That's roughly when closets got bigger. Open floor plans really show up after 2010. A 2005 build might have dated cabinets, but that's paint, not a dealbreaker.

One tip if you're leaning new construction: call us before you walk into a model home. We have relationships with the builders and can often get you better rates, closing costs, or upgrades. Once you've registered yourself at the model, that door can close.

Round 3: Saturday morning walk and coffee, or a slow morning at home?

Leggings, coffee shop, farmers market: East Hill has your name on it. You can walk 12th Avenue for a great panini and coffee, hit the community parks, and plenty of people get around by golf cart. Downtown Pensacola is the other answer, very walkable and bikeable, and the farmers market is right there every Saturday.

Sleep in, coffee on your own porch, no noise: Pace, Milton, Beulah, Cantonment. The further out from downtown, the more room you get. And if you want serious acreage, look at Jay or Chumuckla. There are developments out there where people are building large estates on several acres and seeing deer in the backyard.

And remember, even if you don't live downtown, you can always drive in for the farmers market. Living out there doesn't lock you out of any of it.

Round 4: Big backyard, or the water IS your backyard?

Big backyard for the kids and the neighborhood volleyball games: Cantonment, Beulah, parts of Gulf Breeze, parts of Cordova Park, and plenty out in Pace and Milton.

Dock out back: this is bigger than people realize, because it's not just the beach areas. We have the bay, the sound, the Intracoastal, and the Gulf.

Innerarity Point is a little island right by Perdido Key with a lot of waterfront and a genuine island feel. Gulf Breeze has property on both the sound and the bay. There's Pensacola Beach and Perdido Key, obviously. And along Scenic Highway right in Pensacola there's waterfront, with some condo and townhome complexes offering individual boat slips to owners.

Here's the thing though. We have boat launches everywhere. So you can take the big backyard and still have the boat. That's the best of both worlds and a lot of people miss it.

Round 5: Newer subdivision, or established and historic?

Newer subdivisions tend to mean more turnover, newer construction, and amenities built in. You'll find those in Pace, Milton, Beulah, and Cantonment.

Established and historic means Cordova Park, Scenic Heights, East Hill, North Hill, and Navy Point. These are mature neighborhoods with very low turnover. People buy there and stay for decades. The tradeoff is less inventory and older systems in the houses, and the upside is stable values and mature trees you can't fake.

Round 6: You won $100,000. Bigger house or better location?

Bigger house: Jay and Chumuckla are our country areas. There's a newer subdivision out there called Nature Walk at Pond Creek where we're seeing 6,000 square foot homes on 5 acres. That is not normal for our market. Around here a big house is about 3,500 square feet, and most homes run 2,000 to 3,000. If you're coming from Texas or Colorado, our idea of big may surprise you. Iron Rock in the Cantonment area and parts of Beulah are other spots with larger homes.

Better location: Pensacola Beach, Perdido Key, or Gulf Breeze proper. Gulf Breeze proper is a phenomenal location for how close it is to everything, with a boat launch right there and a rec center with pickleball and tennis courts.

A real example: I had a couple living in one of those big estates up in Chumuckla. They loved the house. They'd built their dream home. But they told me they felt like they'd picked the wrong location, and they'd rather be in a smaller, older house close to the beach where all the kids come over. We see it go the other direction too, people in a small house who want to go to the country for space. Both are valid, just know which one you are.

Round 7: Why are you really moving here?

For a better place to raise your family: there are a lot of homes here built for that, with the bedroom counts and the layouts. Milton has great value. Cordova Park would be my next pick, with sidewalks and parks throughout.

Because you cannot stop thinking about that beach: then let's get you the beach. I had clients recently who told me living on the Gulf was the dream, and they had the budget, but they kept looking at homes in Cantonment. Lovely homes. I told them straight: you're leaving everything behind for this move. If you want the beach, let's get the beach. Let's hear the Gulf every morning.

They did it. They're out there every day with their feet in the sand.

Look at Pensacola Beach, Perdido Key, Navarre Beach, or right nearby. Several Navarre neighborhoods are about 5 minutes from the water, same in Gulf Breeze proper, and Perdido Key has plenty of affordable options within 5 to 10 minutes.

Your results: which one are you?

The Coastal Family. You answered beach, water, beach. You'll give up some house for the location, and it won't bother you, because the beach is your backyard and you're outside constantly anyway. Look at Gulf Breeze, Navarre, Perdido Key, Innerarity Point, and Pensacola Beach.

The Urban Local. You want to walk to coffee, hit the farmers market, and try whatever restaurant just opened, and you're fine being 15 minutes from the sand. That's Downtown Pensacola, East Hill, North Hill, and Scenic Heights. Mostly older homes with a lot of charm, pockets of new construction, and a life where you bike or golf cart to everything and never miss a festival.

The Space Seeker. You want the bigger home and room between you and the neighbors. More house for your money, the big backyard, space for a pool. Your home is your happy place and you'd rather cook than go out. Look at Pace, Milton, Beulah, Cantonment, and go to Jay or Chumuckla for acreage.

And honestly, nothing here is that far. Even in the most remote spots you're maybe 15 minutes from a grocery store, and about 25 minutes from downtown.

Frequently asked questions

Which Pensacola areas are closest to the beach?

Gulf Breeze, Navarre, Perdido Key, Innerarity Point and Pensacola Beach itself. Many neighborhoods in these areas sit 5 to 10 minutes from the water without beachfront pricing.

Where do you find bigger homes and land near Pensacola?

Pace, Milton, Beulah and Cantonment give you more square footage for the money. For several acres, look at Jay and Chumuckla, where homes as large as 6,000 square feet on 5 acres are being built.

Which Pensacola neighborhoods are walkable?

East Hill and Downtown Pensacola. East Hill has 12th Avenue for coffee and food plus community parks, and the Saturday farmers market is downtown. Both are bikeable and golf cart friendly.

What counts as a new home in Pensacola?

Generally anything built after 2005, which is when larger closets became standard. True open floor plans show up consistently after 2010.

How big is a typical Pensacola home?

Most run 2,000 to 3,000 square feet, and 3,500 is considered large here. Buyers from Texas or Colorado often find our scale smaller than they expect.

Did I get it right?

Tally up your answers and tell me which community you landed on. Sometimes we get it wrong, and sometimes there's a needle in the haystack that's perfect for you that neither of us saw coming.

My favorite thing is hopping on a Zoom and doing a map tour. I'll give you the lay of the land, drop in where you'll be working, where the kids would go, where you'd go to church, and we'll see what actually fits.

Text or call (850) 786-3996, DM me on Instagram @christinaleavenworth, or visit www.bestrealtorsinpensacola.com.

So which one are you, Coastal Family, Urban Local, or Space Seeker?

Christina Leavenworth | REALTOR® | The Christina Leavenworth Team | Levin Rinke Realty