Best Place to Live in Sarasota - West of the Trail

Best Place to Live in Sarasota - West of the Trail

In this blog, I’m going to show you around West of the Trail. What kind of real estate you can find, the lifestyle it offers, and some of the best amenities in the area. I’m not going to teach you EVERYTHING, because it’s just. Not. possible. And we’re also NOT talking pricing because that fluctuates. But, for up-to-date pricing in the area and neighborhoods, jump over to my website where you can see active listings for specific properties and neighborhoods. Let’s get started!

I’m defining West of the Trail as West of Tamiami Trail, South of Bahia Vista, and North of Beneva. It runs right along the West coast of Sarasota. Keep in mind, I’m not including Sarasota’s Islands and Keys in this…That’s a whole other area in another blog.

So first…real estate. West of the Trail real estate offers something unique. One: waterfront property and two: boating access. West of the Trail waterfront homes are positioned on the Bay and some on canals that lead to the Bay. It’s really the ideal location for those of you hoping to keep a boat in your backyard. Some of the West of the Trail homes have their own boat docks, while others have neighborhood marinas. And maybe you’re not even into boating at all, but you just like looking at a good view--you’ll find that here too. You’ll also find many homes that aren’t waterfront but have proximity to the water. West of the Trail is made up of a combination of both neighborhoods with HOAs as well as non-deeded side streets. The overall price tag of the area is higher because of its waterfront lifestyle. It’s also a great area to find luxury-style homes. Let’s look at a couple of neighborhoods and areas that are West of the Trail.

Cherokee Park Sarasota

This neighborhood is so unique, filled with history and architectural intrigue.  The neighborhood’s first home was built in the 1920’s. Many of the homes today hold interesting architecture from Mediterranean to modern and everything in between. Another draw to this neighborhood is the larger home lots and mature trees and landscaping throughout adding to its charm. 

Cherokee Park

Harbor Acres Sarasota

One of the cool things about Harbor Acres is that many of its homes are on the Bay or on a canal leading out to the Bay. These waterfront homes are great for boaters or those of you looking for an incredible poolside view. Throughout the neighborhood, you’ll find a combination of traditional Florida homes from the 60’s and 70’s spanning to new modern builds, with their own unique character.

Harbor Acres

Oyster Bay

An area of just under 150 homes, some of which are overlooking the bay. The homes are built from the 1950’s to today. So, you’ll find small homes, big homes, old homes, and new homes. Another draw to Oyster Bay is its proximity to The Field Club, a membership only club with a clubhouse, tennis courts, swimming pool, and marina. 

Oyster Bay Estates


Living West of the Trail - Sarasota, FL


West of the Trail still meets your practical needs with proximity to places like Publix, Trader Joes, Sarasota Memorial Hospital, and Costco, while also giving you some “extras”. A biggie is simply being close to Sarasota’s Islands and Keys. If you’re into fishing, boating, kayaking, paddleboarding, hanging on the beach, waterfront dining, or simply taking a walk along the coast, living West of the Trail gets you that. It’s also fairly close to downtown, which is one of Sarasota’s hubs for dining and entertainment. But, what else can you find right IN that West of the Trail area? Follow me.

This is Southside Village West of the Trail. Almost like a mini downtown area with a couple restaurants, a coffee shop, and one of the areas favorite stops, Morton’s Gourmet Market, a specialty food store with a bakery, coffee shop, meats, seafood, scratch prepared meals, a deli, wine and cheeses. Well, you get the idea. Southside Village is loved by those who live West of the Trail. Let’s check out what’s next!

Phillippi Creek Oyster Bar - Next is the Philippi Creek Oyster Bar right here on the Philippi Creek. A local favorite in this side of town known for its fresh local seafood and casual environment.

Walt’s Fish Market- That leads me to my next stop. Walt’s Fish Market. Another popular hotspot for dining West of the Trail. Walt’s is also known for its fresh local seafood, and the fact that it’s both a restaurant and a fish market! 

Philippi Estate Park- Next is Philippi Estate Park- a 60 acre park with walking paths, dock, playground, and the historic Edson Keith Estate. One of my favorite things about this place is the seasonal farmers market held right here! A popular spot to pick up fresh produce, a bite to eat, and locally made products. 

Well, thanks so much for joining me around Sarasota’s West of the Trail area. If you want to learn more about West of the Trail…Well that’s easy, shoot me over an email, text, or call. I’d love to connect and learn more about how I can help! 

To view all neighborhoods West of the Trail click here

Contact Matt 

Matt Leicht, Realtor®
Cell - 941.256.3321
Email -
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