West of the Trail

Sarasota Homes for Sale

Waterfront Homes, Luxury Homes and Condos

West of the Trail are defined as the neighborhoods "west" of US Hwy 41 or the Tamiami Trail. The most popular West of the Trail neighborhood is the community located centrally around the Plaza anchored by Morton's Gourmet Market. Within walking distances to the market, Sarasota Memorial Hospital and neighborhood restaurants such as Libby's, Hillview Grill and Knick's Tavern, these single-family homes are of mixed architectural styles. Many are old Florida homes and the properties are exquisite. Older homes are being removed or updated in this area and builders are adding all the designer touches in kitchens, bathrooms and fabulous new landscaping to make way for new mini-mansions. Also, close to downtown Sarasota and the beaches of Siesta Key, this beautiful community a is a "must see" for convenience and location, location, location.  Read More...

Included below are West of the Trail homes and condos for sale in the Sarasota, FL area, updated daily from the Sarasota MLS. If you would like more information on any of these Sarasota properties for sale, just click the "Request More Information" button when viewing the details of that property. We can provide you with disclosures, past sales history, dates and prices of homes recently sold nearby, and more.

And, if you haven't already, be sure to register for a free account so that you can receive email alerts whenever West of the Trail homes come on the market in Sarasota.
West of the Trail September 16, 2021
66
Listed
86
Avg. DOM
$605.39
Avg. $ / Sq.Ft.
$1,200,000
Med. List Price
66 Properties
Page 1 of 6
$10,500,000
Subdivision: Block 6 Condominium
4
Beds
4F11/2
Baths
6,131
Sq.Ft.
2018
Year Built
141
Days on Site
A4499051
MLS
Rare opportunity! Brand new, stunning penthouse in the recently completed Ritz Carlton Residence Sarasota. Gorgeous views of Sarasota Bay, the Key islands as well as city views from many windows and...
$8,200,000
Subdivision: Cherokee Lodge
5
Beds
6F21/2
Baths
6,610
Sq.Ft.
2022
Year Built
36
Days on Site
A4508858
MLS
Pre-Construction. To be built. Waterfront located in Cherokee Park! Spectacular 5+ bedroom coastal style single family home complete with guest wing. Features include: gourmet kitchen with sub-zero &...
$6,650,000
Subdivision: Not Part Of A Subdivision
6
Beds
6F21/2
Baths
9,052
Sq.Ft.
1983
Year Built
214
Days on Site
A4491567
MLS
Herein lies the best waterfront opportunity that you will find in Sarasota. The seller is offering a flexible sales structure to include subdividing the parcel with the waterfront lot/home priced at...
$5,795,000
Subdivision: The Residences
3
Beds
3F11/2
Baths
4,951
Sq.Ft.
2001
Year Built
137
Days on Site
A4499645
MLS
Enter this stylish Ritz-Carlton Penthouse through an elegant gallery foyer. Step into this bright, southwest-facing refined home with captivating views at every turn overlooking Sarasota Bay and...
$5,690,000
Subdivision: The Tower Residences
4
Beds
4F11/2
Baths
5,251
Sq.Ft.
2003
Year Built
133
Days on Site
A4500204
MLS
Known worldwide for its excellence and style, The Ritz-Carlton delivers the ultimate in privacy, luxury, and five-star service at The Ritz-Carlton Tower Residences. Located on the Bay and in...
$5,450,000
Subdivision: Sapphire Shores
5
Beds
6F11/2
Baths
5,270
Sq.Ft.
2002
Year Built
7
Days on Site
A4509990
MLS
Waterfront luxury at its finest! Watch scenic sunsets every day right from the comfort of your own home, pool, or PRIVATE SAND AREA!!! Located in the highly sought after Indian Beach Sapphire Shore...
$3,985,000
Subdivision: Oyster Bay Landings
4
Beds
4F11/2
Baths
4,030
Sq.Ft.
2015
Year Built
107
Days on Site
N6115705
MLS
One or more photo(s) has been virtually staged. SUMMER PRICE! Exceptional and Unique Custom Contemporary West Indies Courtyard style residence built in 2016 (Never Lived-In) with luxury, quality and...
$3,895,000
Subdivision: Paradise Shores
4
Beds
4F11/2
Baths
5,777
Sq.Ft.
1958
Year Built
44
Days on Site
A4508637
MLS
Mediterranean masterpiece with attention to every detail is located on a quiet street west of the Trail surrounded by executive caliber estates. The current owners worked with John King with...
$3,695,000
Subdivision: Paradise Shores
4
Beds
4
Baths
4,942
Sq.Ft.
1956
Year Built
190
Days on Site
T3294850
MLS
Brand New Barrel Tile Roof completed 6/2021. This is a rare opportunity for waterfront living in highly sought Paradise Shores. For the boating and watersports enthusiast, there is 190 feet of...
$3,600,000
Subdivision: Matheneys Sub
5
Beds
5F11/2
Baths
4,067
Sq.Ft.
2022
Year Built
127
Days on Site
A4500630
MLS
One or more photo(s) has been virtually staged. Under Construction. Introducing the Coastal Craftsman Rejuvenation at Southside Village. Constructed by the award-winning custom home builder, Dynan...
$3,590,000
Subdivision: The Residences
2
Beds
2F11/2
Baths
3,582
Sq.Ft.
2001
Year Built
45
Days on Site
A4508463
MLS
One or more photo(s) has been virtually staged. Consummate Ritz-Carlton service, world-class amenities and a luxurious lifestyle are what can be can expected at Sarasota's most prestigious address....
$3,499,900
Subdivision: Mcclellan Park
4
Beds
3F11/2
Baths
3,894
Sq.Ft.
1940
Year Built
49
Days on Site
A4508192
MLS
Pre-Construction. To be built. Under construction. Introducing this bespoke custom home in McClellan Park. This brand-new residence will be timeless and functional, and its West of Trail location...

There is quite a variety of home styles in this area. Old Florida, Spanish Mediterranean, ranch homes and a sprinkling of contemporary designs are mixed through the water front, canals and mainland in the West of the Trail stretch from Manatee County to Sarasota County. The neighborhoods are lush with tropical plantings and colorful with blooms year round.

Contact Us Today

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.