Is East of the Trail in Sarasota, FL, the new upscale housing?

Real Estate Agent with Keller Williams Classic Group BK667334

I would define "East of the Trail" in Sarasota as the area East of Tamiami Trail from Webber to Mound Street, where Tamiami Trail and U.S. 301 split off, and West of Tuttle. "West of the Trail" is on the West side of Tamiami Trail and runs West until you reach the Bay.

When I first started as a Sarasota Realtor in 1998, there was a huge difference in desirability between houses West of the Trail and just East of the Trail.  "East of the Trail" was entry level housing.  Living close to downtown wasn't as important.  The houses were old and typically small.  

Now "East of the Trail" close to downtown Sarasota has seen huge increases in both desirability and price appreciation.  The land has become valuable and builders are buying some of the smaller, older houses, knocking them down and building brand new larger houses.

The two largest areas and well known neighborhoods "East of the Trail" are Southgate and Arlington Park.

Why people want to live there.

In part, the desire for people wanting to live close to downtown has fueled this trend.  Depending on where you live some places are within walking distance or a short drive.  One such neighbood shopping center is Southside Village, it is located just West of Tamiami Trail around Hillview Street and Sarasota Memorial Hospital.  It's a popular centrally located neighborhood spot, with shops, bars, restaurants and markets.  The Five O'Clock Club established in 1955 is one well known bar in the neighborhood, Pacific Rim is a popular Asian restaurant, and Gecko's is a popular bar & grill.  There is also Morton's Gourmet Market which has been in business for over 40 years and has really good preprared food.  Another close by shopping center is Westfield Southgate Mall at the corner of Siesta Drive and Tamiami Trail.

 Southside Village ShopsSouthside Village Shops

In a subdivision such as Arlington Park there are now houses listed at prices above $600,000 for new construction.

New construction in Arlington Park is something that just started happening, and I think the trend will continue. Before that it would have been unheard of to knockdown a house "East of the Trail",  people who could afford upscale housing didn't want to live "East of the Trail".  

The differences between "West of the Trail"  and "East of the Trail" are blurring especially in the area between Siesta Drive and Bahia Vista Street.  

My opinion of why this is happening is the location is really great and doesn't change much just because you are on the other side of Tamiami Trail.  

Other reasons why people like it is because of course it is close to US 41, downtown and Arlington Park.  

View Arlington Park houses.  

View Southgate houses.

What's the area like

In Arlington Park a lot of the houses were built in the 1950s.  The houses typically range from 900-1400 sq ft under air.  The lot sizes vary quite a bit but are generally between 5,000-10,000 sq ft.  A lot of the houses have been updated, some extensively.  The Arlington Park area is where I see the trend of knocking down houses to build new, the most prevalent.  

 Arlington ParkArlington Park


In Southgate the houses were generally built in the 1950s-1960s.  The houses range from 1,100-2,500 sq ft. The lot sizes are approximately 10,000 sq ft some smaller and some larger.  

 The schools in the "East of the Trail" area are:

The elementary schools are Southside and Alta Vista

The middle school is Brookside

The High School is Sarasota High

source: Sarasota County Schools 

 If you are interested in learning more about "East of the Trail" housing in Sarasota please contact me.

You may also enjoy:

Should I Sell My Home As a For Sale By Owner(FSBO) In Sarasota, FL?

Should You List Your Sarasota Home with a Flat Fee Multiple Listing Service Broker?

Guide On How to Price Your Home For Sale in Sarasota, FL


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About the Author,

Jason Silverstein has been has been a life long resident of Sarasota, FL and a Realtor since 1998, he writes based on his experiences.  You can find more listings or information about me at  To subscribe to my blog click here.

Comments (18)

Sybil Campbell
Fernandina Beach, FL
Referral Agent Amelia Island Florida

Hi Jason Silverstein, Welcome to Active Rain and congratulations on your first blog post. BTW, I started my real estate career in Florida in 1998.

Jan 14, 2016 10:15 AM
Jason Silverstein

Thanks Sybil!

Jan 14, 2016 08:52 PM
Joan Dickie
Keller Williams Premier Realty - La Crosse, WI
Keller Williams Premier Realty

Great post!  Thanks for sharing your your community with us.

Jan 14, 2016 10:27 AM
Jason Silverstein

Thanks Joan!

Jan 14, 2016 08:52 PM
The Temple Team
THE TEMPLE TEAM - Mooresville, NC
Specializing in Lake Norman/Charlotte/Charleston

CONGRATULATIONS on your First Blog Post! And ... WELCOME TO ACTIVE RAIN ... you're going to LOVE it here!


Jan 14, 2016 01:00 PM
Jason Silverstein

Thanks Kent!

Jan 14, 2016 08:53 PM
Kat Palmiotti
eXp Commercial, Referral Divison - Kalispell, MT
Helping your Montana dreams take root

Welcome to ActiveRain and thanks for sharing this Sarasota area information. I love neighborhoods where you can walk to everything - that's right up my alley!

Jan 14, 2016 07:37 PM
Jason Silverstein

Thanks Kat!

Jan 14, 2016 08:53 PM
Michael J. Perry
KW Elite - Lancaster, PA
Lancaster, PA Relo Specialist

This type of blog post is what Active Rain is all about ! Keep them coming !

Jan 14, 2016 08:32 PM
Jason Silverstein

Thanks Michael!

Jan 14, 2016 08:53 PM
Barbara Todaro
RE/MAX Executive Realty - Happily Retired - Franklin, MA
Previously Affiliated with The Todaro Team

Good morning, Jason Silverstein when builders buy homes that are livabe and knock them down to build new homes, that indicates the strong desire of people to become a member of that community.... good post....

Jan 14, 2016 09:36 PM
Jason Silverstein

That's right. Thanks Barbara!

Jan 15, 2016 02:24 AM
Barbara Todaro
RE/MAX Executive Realty - Happily Retired - Franklin, MA
Previously Affiliated with The Todaro Team

and welcome to ActiveRain.... it's a great place to learn, share, market and network....and I hope you enjoy and benefit from all of it....

Jan 14, 2016 09:37 PM
Tony and Suzanne Marriott, Associate Brokers
Serving the Greater Phoenix and Scottsdale Metropolitan Area - Scottsdale, AZ
Haven Express @ Keller Williams Arizona Realty

Welcome to Active Rain!  As REALTORS who have been here for more than 9 years, it's well worth it!


Jan 14, 2016 10:00 PM
Jason Silverstein


Jan 15, 2016 02:25 AM
Nicole Doty - Gilbert Real Estate Expert
Zion Realty - Gilbert, AZ
Broker/Owner of Zion Realty

What a great first blog post showing you are the area expert for buyers and sellers! Welcome to Active Rain Jason.

Jan 14, 2016 11:09 PM
Jason Silverstein

Thanks Nicole!

Jan 15, 2016 02:26 AM
Mery Fernandez Empire Network Realty Luxury Brokerage
Empire Network Realty INC. - Orlando, FL
The Rise of An Empire, Let's Build Yours!

Hi Jason! Welcome to the world of Activerain, may your blogging  create a whole new chapter in your Real Estate Career.

Jan 15, 2016 02:25 AM
Jason Silverstein
Keller Williams Classic Group - Sarasota, FL
Sarasota,FL Realtor since 1998, Broker-Associate

Thanks Mery!

Jan 15, 2016 05:32 AM
Les & Sarah Oswald
Realty One Group - Eastvale, CA
Broker, Realtor and Investor

Welcome to ActiveRain and congratulations on your first blog. You are definitely the go to agent for Sarasota, FL. Great introduction of your local community.

Jan 17, 2016 02:25 AM
Jason Silverstein
Keller Williams Classic Group - Sarasota, FL
Sarasota,FL Realtor since 1998, Broker-Associate

Thanks Les & Sarah

Jan 18, 2016 03:11 AM
Letitia Stevenson
BHHS Fox & Roach | - Greenville, DE
Listing Agent DE/PA/MD, Digital Marketer & Coach

Hi Jason, Thanks for sharing and welcome to the Rain! ActiveRain is a great place to share your knowledge, expertise and thoughts, as well as network and learn so much from the vast pool of talent already onboard. I look forward to reading your upcoming posts. If you would like to connect with me on ActiveRain, please subscribe to my blog! Welcome Aboard, Happy New Year and Much Success!  

Feb 01, 2016 09:13 AM
Jason Silverstein

Thanks Letitia!

Feb 07, 2016 08:20 PM
Robert May
Robert W May - Lethbridge Real Estate - Lethbridge, AB
Real estate consulting

Welcome to the Activerain community and congratulations on your first blog post.  There is so much to read and learn here that sometimes you can get lost for hours.  Once you get familiar with the site and have time, feel free to come stop by my blog and leave a comment or just say hello.

Feb 05, 2016 09:16 AM
Jason Silverstein

Thanks Robert!

Feb 07, 2016 08:20 PM
Joan Cox
House to Home, Inc. - Denver Real Estate - 720-231-6373 - Denver, CO
Denver Real Estate - Selling One Home at a Time

Jason, you paint a great picture of Sarasota, and love your photo too.    Should visit soon!  Welcome to ActiveRain! 

Feb 06, 2016 05:50 AM
Jason Silverstein

Thanks Joan!

Feb 07, 2016 08:21 PM
Robert May
Robert W May - Lethbridge Real Estate - Lethbridge, AB
Real estate consulting

Welcome to Activerain and congratultions on your first blog post here.  There is a ton of stuff to read and a great community of members to interact and network with.  Feel free to stop by my blog and leave a comment or just say hello.

Feb 12, 2016 01:32 PM
Robert May
Robert W May - Lethbridge Real Estate - Lethbridge, AB
Real estate consulting

Happy Valentines day.  Just wanted to wish you the best this long weekend and let you know that if you require any help here at activerain just send me a message and I will try to help you out.  Have a successful weekend!  Robert May

Feb 14, 2016 02:38 AM