This blog article is derived directly from our YouTube video (featured at the bottom)

Today, I'm actually doing part one of the reformatting of the 2023 Best Places to Live in Sarasota, Florida. I haven't covered this topic I don't think in totality in like three years, so I wanted to redo it, but not in the same way. So I broke this up into three videos so that it was way more consumable because I am not short-winded by any nature, so it was way too long, but I broke it up into categories so I could go a little deeper. I talk about what is actually special and different to me versus all the other places in Florida in each category. I talk about how to navigate the different ways to live and how I think about that. I even touch on the real estate prices themselves. And at the end of the video, I'll tell you how to get engaged if you want to go any further with our team. So I really hope you enjoy part one of this series and let's get going.

Okay, what I'd like to do first in this video is start off with what exactly is special about this particular category; differentiators, foundational context to give us a nice lay of the land. So one of my favorite concepts about the Sarasota area is the idea of when you go west, you get everything, by simply going to your right. All the things that Sarasota has historically been known for, the arts and the culture, the Gulf Coast location, world-class beaches, all of that clustered in a pretty low-density geographic area.

So like for instance, the downtown, our main downtown district where I stand in here today, below me, is our main thoroughfare; our traditional downtown, our main street, the restaurants, art galleries, and the theaters. But all of this is three miles one way to Lido Beach, Longboat Keys above that, Anna Maria Islands above that, six miles one way below to Siesta Key Beach, top 10 world beaches.

And then all the shopping districts beyond the new suburban ones you have downtown of course with all of that, and with traditional kind of value. You have St. Armands Circle, a hundred plus shops and boutiques at cosmopolitan, high-end, John Ringling-designed beach shopping district. And there's Siesta Key Village and Crescent Village. So you have most of what the town, old-school real estate dynamic-wise would value, versus some fragile, flimsy-only downtown-based perceived value because you have the coast too. So a lot of that creates a pretty easy-to-navigate real estate market in a general sense because all the value is based on being east, west, north, and south of the main concept of this value. And I think that's really special the more you navigate Florida as a whole.

Play First, Work Second

The second major point I wanted to make in this particular category is the idea that our major downtown area is very much a play-first and work-second kind of culture. Where most downtowns I would say in the country, or at least a good portion of downtowns in the country, are very much based on economic feasibility. If people are hustling into the urban districts, because that's where the employers are, that's where the stuff's going on, that's what they need for a job and economic reasons. Well, in a town like this where you could say the good and the bad about if you're coming here for a job or something like that, but Sarasota isn't necessarily your first choice typically in that realm. But the benefit of our downtown being not based on that is I think tenfold. The pace of life here is extremely laid back, and extremely lovely. I don't care how many snowbirds are here during the season, this downtown never feels clustered to me, not one time. Not to park, and not to walk. The retail, all the retail establishments here are very much based on hospitality other than a bunch of businesses being clustered in where even parts of Tampa and stuff, way more businesses than you do actual restaurants. Here, we're art galleries on every corner and restaurants, and they just do stuff like that because it's not based on those reasons.

Even the condos here, the condo living, I would say is very much more about urban convenience and luxury than it is about commute feasibility, beyond the downtown being unbelievably walkable from end to end. My other office is down to here and the water's behind us here, very walkable, and you're talking 10, 15 minutes to walk the entire downtown, very easy to navigate. All have different kind of layers to them as well. Feels extremely clean, clean, and upscale. I would say those are real takeaways. And I've lived in probably nine or 10 total cities in all the major ones, Jacksonville, Miami, and Tampa. And nothing feels this kind of upscale, charming, and laid back to me across the whole country if you had to separate them. So I do think that is special if you're considering remotely living in this district.

How to Navigate Living Options in Sarasota

Now, with all of that being said, how do you actually go about navigating living options for this area? This falls into three distinct categories in my personal opinion, and that's traditional urban living, that is unique suburban living, which I'll explain more, and that's actually being on the beaches.

Traditional Urban Category

All right, let me start off with my traditional urban category. So this one is one that I'm kind of self-creating, and I'm going to categorize a few things in here, but it's all stuff that you would generally expect when it comes to living in a downtown. So the first, let's talk downtown itself. So downtown itself, if we park condominiums for a second, you have all the historical stuff. So you have the charming historical districts where you're sacrificing size and age to gain proximity, and we have some really nice ones. Just a couple examples: Laurel Park, Burns Court is lovely, you have Towels Court. So there's that side of it where very much bungalow style kind of stuff.

Condominiums

And then we have the condominiums itself. So just literally in a three, four mile square radius here, hundreds of buildings to pick from. So how you decide amongst them and navigate, it's really about the boutique nature, the newness of the resale versus the pre-construction, the fees. And the cool thing about here is boutique versus high-rise. We have an 18-story limit in Sarasota, so the most they could put in one building is about 150. And it's not going to look like Manhattan, at least currently, because of that height limit, and that's the reason for it. But then you start to get more intricate and you're going to say, I like this street better than this street, like Palm Avenue behind me here looks very different than Lemon and Main Street and State Street. So that's usually how you would navigate as you get in depth in your search.

Then also on condos, you have a couple more options. So let's say you want, you're not on the beach yet, right, because we're not doing that yet, but you want more water facing proximity, because we hit bay and then we hit Gulf Waters. So the three options for that right now are if you go in front of this street here, we'll show on the map too, but the street in front of this building, one street over, it's called Gulfstream. Gulfstream is basically the front of downtown, so you're still in downtown but you're at the front of it. So because of that, there's only a street in front of you. So you view the bay in a lot of these condominiums, you're at least very close, but you can walk right behind you in downtown.

So Gulfstream has a whole row of condominiums, one or two that are newer, but the rest are resale or older resales. And then there's two separate areas that are real special. And again, reach out if you want any more information here, because this isn't the kind of video where I'm able to break down everything. I want it more brief and more consumable. The two other water facing districts are really unique. One's called the Quay, and the Quay is right down the street here, and that's a 14-acre waterfront district that's going to be mixed use commercial space. It's all brand new. Mixed use, commercial retail, condominium living. That's where they built the Bayso, couple Ritz Carleton's over there, the one park, the new condominium's there, a couple hotels. There's a marina. That's next to the Bay Project, 53-acre whole thing adds a bunch of more stuff. And then you can go a little further and there's a peninsula called Golden Gate, and obviously it's surrounded by water on three sides, and that's where you'll see a whole other bunch of that condominium living. But you can imagine that these are all on the water. These are all in front of the water, so your best chance to get views and that kind of thing, but still considered downtown adjacent.

Tamiami Trail

So that's the main part of the traditional urban living. And then we have a Tamiami Trail. It's a road in the front and a lot of people base east and west of the Trail. So if you're east of the Trail, you're a little further out, you might be a mile from downtown, and if you're west, you're kind of in it more depending on north to south. So there is a layer of, I would still consider kind of downtown, more downtown than anything that would be east of the Trail, and that would be another area you can navigate for. A lot of times it's for affordability because being in downtown south, there's just only so many districts you could live in a single family home. So that's what I would say about traditional urban.

Unique Suburban Living

My second one, I'm calling unique suburban living. This is one where I think Sarasota really excels amongst probably the country as a whole. So we have this one district where I mentioned that Tamiami Trail, which is US 41, which is basically the coastal version of the interstate. It runs north to south up and down really far, but we have an area of land that's west of it. So in essence, most of our beaches are barrier islands. So I'm going to try to articulate this the best, but by being west of US 41, but not on the beach yet, you're the closest strip of mainland available before you fall off into the water.

And if you're in the right district north to south, then you have access to literally everything I described on my very first point of going west to get everything. But you don't just have all of that. You're not sitting in a little condominium because of space. There are full on neighborhoods here with large single family homes on existing mature land, in low-fee environments because the land's old, because it's not this big area, in high-rated school districts. So you can get literally the best of both worlds that people struggle with of being like, yeah, I would love to be in downtown or the beaches, but I can't do that with the family size, and I want a neighborhood, I want it walkable. So this area is very, very unique. And then the big point here is that it's not just being close to the water in Sarasota, it's access to functional water. So there's bridges to get to the beach. If you're close to the water and you're not near the bridge, then it's not that functional to get over there. If you're close to the water and you can't access it for boating or whatever you may do, it's not that functional.

So there's a couple neighborhoods where, I'll give you some landmarks here as research items or whatever, and again, please reach out if you want any more info, but Cherokee Park, McClellan Park, Bayview. These areas sit literally in this little triangle where on one side you look over to the right and downtown's like maybe a half a mile away, a mile away at the most; full on neighborhoods, wide streets. And then you are in between the South Bridge for Lido Beach and the North Bridge for Siesta Key. So you literally go boom, boom, boom, and you have one of the best places probably to live in the entire country. As far as if I'm going to move here, I want to be in the thick of it. Obviously, this comes at a premium, but I want to be in the thick of it and I don't want to take any sacrifices when it comes to location or house, then west of the Trail on suburban single-family housing I think is incredibly unique.

The Beaches

Okay, my third category, the beaches. So here you really have to separate it because beyond one beach, basically, they're all barrier islands. You're crossing bridges to get there. It's a commitment. Once you're there, you're there. My parents live on Siesta Key and they're totally beach people because you're not going to want to run on and off there every day in my opinion. So I'm just going to kind of riff on the differences between them because we can only build this out so much for this video. I don't want it to get too hairy. 

Siesta Key, FL

So let's start with Siesta Key. Siesta Key sits six miles below downtown as I mentioned. It's about seven, eight miles end to end. It's a barrier island that has two bridges on and off, has three major beaches on it. You have Siesta Key, which is the main one on the north side of the island, and that's next to Siesta Key Shopping Village, which is also the main shopping village. In the middle of the island, you have a beach called Crescent Beach. A lot of similar characteristics with the beautiful sand and all that kind of thing, but it's a lot less accessible to the public as far as parking lots and that kind of thing. So a lot of condominiums and stuff cluster on there for rental. And then the very bottom of the island is called Turtle Beach. So not quite as nice sand and that kind of thing, but a lot more private, a lot more residential feeling. And so that's kind of how the island is clustered.

And then the north side of the island, above the main beach, is where you're going to find most of your single-family homes, most of your neighborhoods. There's more than you think because a lot of the neighborhoods are hard to understand. I have a video I'll try to tag where I broke this down, but they're hard to understand just because there are no resale homes available, people don't realize the gravity of how many neighborhoods there actually are. I think there are 43 technically. And then the last section of this video, I'm going to touch on pricing. And then you have a fair amount of condominiums, but they're going to be mostly older and you do have a lot of the condo, hotel kind of stuff like that.

But the general consensus of the aesthetics of this island and feel, it's going to be much more touristy. So a lot more affordable for single families than some places, but much more touristy as an overall feel. So you got to like that kind of approachable, casual visit tourist environment. Even if you're living on the island, you have to not absolutely hate that because that will be the vibe on Siesta Key.

Longboat Key, FL

Okay, the second one I want to cover is called Longboat Key, Florida. This is a great juxtaposition versus Siesta Key. So this one sits north of downtown opposite of Siesta by about four or five miles. It is a very similar size, actually north to south, you know, have seven, eight miles I think total, but a very different feel. It's going to feel way more residential, way more private. They do have public access, but not in the same way as Siesta. So it's going to feel a lot less approachable to the public. So it's a little bit more discreet of a place. It feels like a lot more homestead residents and permanent residents reside there. So that's one thing to consider.

It's a very skinny island. So the benefit of that, is on one side you have a bay, on the other side you have the beach, and it's not that hard to come by because it's not a very wide place. So you turn around and you have water. And you have a mix of hotels and single families, like most places. The one thing to think about this is if you get it, this one's going to feel a little bit more like a silo. Because by going north of downtown, the mainland west, and the mainland east of what is now Northern Sarasota. That's where the airport's at, that's where... It's more up-and-coming of an area than going south of downtown.

So south of the southern bridge of Siesta Key accesses South Sarasota Palmer Ranch, a way more established kind of place. So the more you get north on above country club shores and the Longboat Key club area on this island, it's going to be more like a commitment to, "I'm a beach person." It might be a little bit hairier getting off the island because if you come south, you're going to have to pass through the St. Armands Circle shopping district. But I would say that's how I'd sum up the difference between these two. This one's going to be a lot less casual, and a lot more upscale feeling than most parts of Siesta Key.

Venice Island, FL

Okay, the third major one I wanted to cover, just explain the beaches in general here, is called Venice Island, Florida. So after this, I'll cover the rest real quick in a speed round, but Venice Island gives you a good third example.

So one, this one sits 45 minutes south of downtown Sarasota because this is downtown Venice. So this is like our... Sarasota's quaint southern neighbor is Venice, Florida, which is a city within Sarasota County. But it is kind of separate, and I'll explain here in a minute. So one differentiator-wise, Venice Island is our only non-barrier island. So by not having bridges that divide the beaches like Siesta and Longboat, et cetera, then this place, if you're anywhere in the vicinity of the island, it feels incredibly more coastal. Two, this is one of the most affordable places to live in the entire state of Florida on the Gulf Coast and to walk to the beach in both a condominium and a single-family home; total cost of ownership, it's one of the most affordable. So it's still kind of underrated in that facet. And three, it gives you just a completely generally different feel.

It's going to be way more like Siesta Key in the casual nature of it. It's going to be historical, it's going to be casual, but it typically is going to feel a lot more quaint, a lot more charming, a lot more laid back, and a little bit of probably average older population overall versus the Siesta kind of crowd that pours in there. And then also they have their three own beaches. So by being on that island, you have Venice Beach that's walkable from pretty much the entire island. You have Caspersen Beach, which a lot of people consider the shark's tooth capital of the world. And then you have Brohard Beach, which is our only dog beach in the entire county. So that gives you a good third example of Siesta versus Longboat versus Venice.

Anna Maria Island, FL

Now, beyond all of that, I would say you have, of course, you have Anna Maria Island. So these are all kinds of offshoots of the conversation we just had.

Lido Beach, FL

So if you go... Lido's kind of a pass-through beach a little bit. So Lido Key is on St Armands Circle. There are single-family districts around it, and there are condominiums, but it's a lot more in the thick of it. So I didn't separate it as a category, but that's always an option. It just gets you closer to all the stuff, but it is more minute. But you go Lido, Longboat Key, and then you just go further on this same barrier island, that we'll show here on a map, but the northern tip of that is Anna Maria Island. People fall in love with that. I would say Anna Maria is a combination of more of Siesta Key plus Venice. It's pastel colors, it's laid back, and it's definitely touristy, but it is the northernmost tip of the entire double county. So when you're out there, you are out there, so you want to be looking for that.

On the way there you have onesies, twosies in Holmes Beach, and Bradenton, and Coquina. And then below Venice, you have a similar kind of vein. You have Englewood. So Englewood, if Siesta's a little busy for you and you're like, "Venice is for me, I like the style better," whatever. Then if Venice, whether the price or even Venice is too busy for you, then the junior version of Venice would be Englewood. You have Manasota Key down there, et cetera. But once you get the concept of the three major players of feel, then you can really have the context of a lot of parts of Florida on that same conversation because they all kind of follow the same methodology of premise in general, in my personal opinion.

Real Estate Prices

And lastly, just to add a little bit more value, I want to wanted to talk about some real estate prices in brevity, just so this all isn't pie in the sky. So downtown Sarasota, which I talked through in the last six months, the median closed sales price was $967,000, so I'll give you that. Both Siesta Key and Longboat Key were 1.1 million dollars as closed price. This includes all types of properties, condominiums, and single-family homes. And then Venice Island, you'll see what I mean here. Venice Island, as I digress, was $447,000 in the last 180 days of closed prices.