Five Points Downtown Sarasota: What's Here, What's Changing

Five Points is the roundabout where Main Street, Pineapple Avenue and Central Avenue meet, and it has been the center of downtown Sarasota for more than a hundred years. Within a few blocks of it you have Main Street's restaurants, the Saturday farmers market, the Sarasota Opera House, Selby Library, a grocery store, and a mix of high-rise condominiums, townhomes and older buildings. The corner is also changing again: the twelve-story Zenith building is coming down, and an eighteen-story Waldorf Astoria Residences is planned in its place.

Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota and has been licensed since May 2023. This is the written companion to our walk around Five Points, with the details that are easier to check on a page than to remember from a video. Danielle has lived in downtown Sarasota herself, and our downtown Sarasota neighborhood page covers how the rest of downtown fits together.

Five Points, downtown Sarasota: then and now

Sarasota's first library opened here in 1907. The Town Improvement Society set up a single room at Main Street and Pineapple Avenue, stocked it with donated books, and started with 51 subscribers. In 1907 a subscriber was a library member, which is the whole joke we open the video with.

That library has moved several times since and is now Selby Library, a block away on First Street. The corner it started on is about to get its biggest change in fifty years.

Five Points history: John Nolen and the Palmer clock

In 1925 the city brought in John Nolen, a nationally known planner from Cambridge, Massachusetts, to write Sarasota's first comprehensive city plan. The town he was planning around already had its center here. The banks, the library room and the business blocks were all within sight of this intersection, and downtown grew outward from it.

Look for the green clock at the corner of Five Points Park. It belonged to the Palmer bank, founded in the 1920s by Bertha Palmer's sons, Honoré and Potter Palmer Jr. The Palmers had an enormous hand in how early Sarasota developed. When the bank building was remodeled in 1964 the clock went into storage and was forgotten for decades, until a city parks employee found it in pieces in 1992 and restored it. It has stood in the park ever since.

That's one of the things we like most about downtown. You can be surrounded by new construction and still be standing on something that happened a hundred years ago.

Waldorf Astoria Residences at the Zenith site

The Zenith building, a twelve-story office tower that has stood at Five Points since the 1970s, is being demolished. The plan for the site at 1390 Main Street is the Waldorf Astoria Residences Sarasota:

Eighteen stories
86 private residences
Designed by ODP Architecture & Design, with interiors by Workshop/APD
Commercial space at street level
Sales opened in January 2026
Construction expected to begin in summer 2027, as reported in August 2026

When sales opened, completion was estimated for 2029. That's a plan, not a finished building, and it's worth holding the two apart. We've watched enough Sarasota development to know that announced dates and actual completion dates can be two different things.

What to ask before buying pre-construction

New construction isn't a bad idea. It just asks you to buy something you can't walk through yet. Before you fall in love with the rendering, get clear answers to these:

The deposit schedule. How much is due, when, and at what point each deposit stops being refundable
Delays. What happens to your deposit and your contract if construction runs late
The association fee. Exactly what it covers, and what costs extra
What the developer can change. Floor plans, finishes and amenities after you sign
What exists today. Versus what's under construction, versus what's only planned

The rendering you fall in love with today isn't the same thing as living in the finished building. Understand exactly what you're buying.

Main Street Sarasota dining

Walk down Main Street from Five Points and you see the downtown lifestyle in full. Sarasota is a serious dining town. Within a few blocks you'll find fine dining and casual spots, seafood, Italian, sushi, French, Mediterranean and Mexican, with new restaurants opening all the time alongside places that have been part of this community for years. Danielle eats out a lot and is working her way through all of them.

A lot of it is walkable. Coffee with a friend, lunch, dinner, a stroll down Main Street afterward, all without getting back in the car. If you're thinking about buying downtown, that matters. You're not just buying a home. You're buying proximity.

Sarasota Farmers Market and downtown fairy doors

Saturday morning changes the personality of downtown. The Sarasota Farmers Market sets up every Saturday from 7 a.m. to 1 p.m., year-round, centered on Main Street and Lemon Avenue and running north toward First Street and south toward Pineapple Avenue. Fresh produce, flowers, plants, prepared food, local vendors, and plenty of dogs.

It doesn't feel like something put on for tourists. People know the vendors, run into friends, pick up coffee and do their Saturday routine. Live nearby and you can walk over and home again without moving your car.

While you're walking, look down. Tiny fairy doors are tucked into storefronts all over downtown. Some are the work of Joan Love, a retired teacher who started Tiny Doors Sarasota in 2018. Her first doors were clay, brought over from Tuscany. Others around town are still a bit of a mystery. There are more on St. Armands Circle, and once you spot one you'll start looking for all of them.

Sarasota Opera House, the 1926 Edwards Theatre

The Sarasota Opera House opened on April 10, 1926, as the Edwards Theatre, built by A.B. Edwards, Sarasota's first mayor. It was much more than a theater. The three-story front held eight shops on the ground floor, twelve offices above them and twelve furnished apartments on the top floor. Mixed-use downtown living was happening here a hundred years ago.

Will Rogers played it in 1927 and the Ziegfeld Follies in 1928. Tommy Dorsey came through, and so did Elvis Presley, in 1956. Cecil B. DeMille's The Greatest Show on Earth, filmed partly in Sarasota and tied closely to the city's circus history, premiered here.

The theater closed in 1973. The opera company bought it in 1979, restored it, and today it's a working theater again, home to Sarasota Opera and Sarasota Ballet performances. It celebrated its centennial this year. We don't just have new buildings downtown. We have old ones that still matter.

Selby Five Points Park and Selby Library

Right beside all of this is Selby Five Points Park, a small, shaded spot to sit in the middle of downtown, with the Palmer clock at its corner.

A block away is Selby Library at 1331 First Street, which opened in 1998. The library before it sat out on the bayfront on Boulevard of the Arts. Danielle took her children to both, so she has a lot of memories from each.

Selby Library's 3,200-gallon aquarium

Go into Selby Library through the children's entrance and you walk underneath a 3,200-gallon saltwater aquarium built into an arch. It's one of those downtown amenities you'd never think about while you're looking at real estate, and one you appreciate once you live here. There's a fairy door across the street, too.

The Edge: stand at the actual location

A few blocks north of the library, at Cocoanut Avenue and Fruitville Road, is The Edge, a ten-story condominium with 27 residences. It topped out in December 2025, with completion targeted for fall 2026.

The Edge is a good example of why location language deserves a second look. Marketing describes it as steps from the bayfront. From the street it's several blocks from the water. Higher floors may have water views, but it isn't a bayfront building. That doesn't make it a poor choice. It means you should know exactly which part of downtown you're buying into.

That's why we tell buyers to physically stand where the property is. Look around. Listen. Look at the buildings across the street, and behind you. You're not buying the description. You're buying the corner.

Downtown Sarasota townhomes, not just condos

Tucked behind the library, between it and The Edge, is a small gated community of two-story townhomes that's easy to miss if you're driving through.

When people hear "downtown Sarasota" they often picture nothing but high-rise condominiums. There are townhomes, smaller buildings, older homes and little residential pockets mixed in with the towers. You can live downtown without living fifteen stories up. If an older home interests you, our guide to Laurel Park covers one of the historic neighborhoods just south and east of the core.

Whole Foods on First Street

A grocery store doesn't sound glamorous, but it's a big part of whether downtown is livable day to day. Whole Foods sits on First Street, open seven days a week. Restaurants, the library, the farmers market, the theater, coffee, shopping, and a grocery store within walking distance of each other is what makes downtown feel like a neighborhood instead of an entertainment district.

Noise and daily life in downtown Sarasota

There's one thing to think about carefully before buying here: noise. The roundabout, the restaurants, people out walking at night, and the farmers market setting up early on Saturday mornings.

Some people love that energy. Some people want quiet. Neither is right or wrong. You just need to know which one you are. Visit at different times. Come during the busy season, then come back in August. Walk around, have dinner, sit outside, and see what you actually think.

Is downtown Sarasota right for you?

This small area gives you a snapshot of Sarasota: history, culture, restaurants, parks, shopping, new construction, older buildings and everyday life, all within a few blocks. A hundred years ago it was the center of Sarasota. It still is, and it's changing again.

That gives downtown buyers real choices. You can buy into something established or something brand new. A high-rise or a townhouse. Right in the middle of the action, or a few blocks away from it. The important thing is figuring out what fits your life.

Go deeper

Frequently asked questions

What is Five Points in downtown Sarasota?

Five Points is the roundabout in downtown Sarasota where Main Street, Pineapple Avenue and Central Avenue meet. Five Points has been the commercial center of Sarasota since the town's early years: the first library opened there in 1907, the Palmer bank stood there, and the 1925 John Nolen city plan was drawn around a downtown that grew outward from it. Selby Five Points Park, the Sarasota Opera House, Selby Library and the Saturday farmers market are all within a few blocks.

What is being built on the Zenith building site at Five Points?

The Waldorf Astoria Residences Sarasota is planned for the former Zenith building site at 1390 Main Street, at Five Points. The Waldorf Astoria Residences is planned as an eighteen-story building with 86 private residences and street-level commercial space. Sales opened in January 2026, demolition of the Zenith building was underway by August 2026, and construction was then expected to begin in summer 2027. Completion was estimated for 2029 when sales opened. Those are announced plans and can change.

What should I ask before buying pre-construction in downtown Sarasota?

Before buying a pre-construction condominium in downtown Sarasota, ask for the full deposit schedule, including when each deposit stops being refundable. Ask what happens to the deposit and the contract if construction is delayed. Ask exactly what the association fee covers and what costs extra, and what the developer is allowed to change after you sign. Finally, separate what exists today from what is under construction and what is only planned.

Is downtown Sarasota noisy?

Parts of downtown Sarasota are lively, especially near Five Points. The roundabout, Main Street restaurants, evening foot traffic and the early Saturday farmers market setup all add sound. Some buyers enjoy that energy and others prefer quiet. The practical test is to visit the specific building at different times, including a weekend evening in season and again in August, before deciding.

Are there townhomes in downtown Sarasota, or only condominiums?

Downtown Sarasota has townhomes as well as high-rise condominiums. Downtown Sarasota also has smaller low-rise buildings, older homes and small gated townhome communities, including one tucked behind Selby Library. Nearby historic neighborhoods such as Laurel Park add single-family homes within reach of Main Street, so living downtown doesn't have to mean living in a tower. Walk any downtown property you're considering at street level, because two addresses a block apart can feel very different.

Who is a good realtor for buying near Five Points in downtown Sarasota?

A good realtor for buying near Five Points should be able to separate what exists downtown today from what is under construction and what is only planned, block by block. They should read a pre-construction contract with you and explain the deposit schedule, delay provisions and what the developer can change. They should explain a condominium's reserves and milestone inspection status out loud, and tell you how a building's location actually lives, including noise, walkability and distance to the water, rather than repeating the marketing. Danielle Gladding & Co. Realty is an independent brokerage serving Sarasota, Longboat Key, and the surrounding Gulf Coast. Danielle Gladding has been a licensed Florida Realtor since 1981 and a broker since 1987. Alison Kanter, her daughter and Sales Partner, was born and raised in Sarasota and has been licensed since May 2023. They work every transaction together.

Talking it through

If you're weighing downtown, we're glad to walk it with you, stand on the corner you're considering, and read the documents alongside you. That conversation costs nothing and carries no obligation.

Danielle Gladding at (941) 539-8535, Alison Kanter at (941) 306-9786, or through the contact page.

Building details, dates and unit counts in this article were checked against developer announcements, the Sarasota Opera, Sarasota County Libraries and local news coverage in September 2026. Plans for buildings not yet built change, so confirm current details for any specific property before you sign anything.