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.

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West of the Trail June 5, 2020
276
Listed
167
Avg. DOM
$434.56
Avg. $ / Sq.Ft.
$827,450
Med. List Price
276 Properties
Page 1 of 23
Open (Virtual) 6/5
1814 Roland St Sarasota, FL 34231
$6,500,000
Subdivision: Cedar Cove
6
Beds
6F31/2
Baths
10,554
Sq.Ft.
1990
Year Built
178
Days on Site
A4452913
MLS
The Ultimate Residence to Shelter in Place. Weave your way up to this unassumingly majestic ~2.5 acre gated residence on wide water of Sarasota s tranquil Intracoastal Waterway and discover easy...
$6,495,000
Subdivision: Harbor Acres
5
Beds
4F21/2
Baths
5,244
Sq.Ft.
1999
Year Built
213
Days on Site
A4450162
MLS
Hailed as one of the best lots in Harbor Acres, spectacular direct views of Sarasota Bay, John Ringling Bridge, downtown s cityscape and sights of sailboats abound around every corner of this...
$5,750,000
Subdivision: Owens
5
Beds
6F11/2
Baths
7,108
Sq.Ft.
1998
Year Built
202
Days on Site
U8063396
MLS
Paradise on Sarasota Bay! This trophy waterfront estate property is perfectly positioned to draw the sparkling bay into the heart of the property, through three levels of floor-to-ceiling windows....
$4,650,000
Subdivision: Oyster Bay Landings
4
Beds
4F21/2
Baths
5,889
Sq.Ft.
2006
Year Built
143
Days on Site
A4455314
MLS
Inspired Coastal Design. Located in the private gated enclave of Oyster Bay Landings, this amazing waterfront residence combines unique architecture and incredible interior design to create a...
$4,590,000
Subdivision: San Remo Estates
5
Beds
5F21/2
Baths
6,710
Sq.Ft.
2009
Year Built
150
Days on Site
W7819412
MLS
Stunning Sarasota waterfront property. Prime location in desirable West-of-Trail San Remo Estates, with spectacular bay/inter-coastal views, this custom built 6,700 sq ft home offers 2 Master Suites...
$4,300,000
Subdivision: The Ritz-Carlton Residences, Sarasota
4
Beds
5
Baths
4,855
Sq.Ft.
2019
Year Built
65
Days on Site
A4464423
MLS
Under Construction. Private elevator doors open to an expansive waterfront terrace offering unobstructed water views of Sarasota Bay, the Gulf of Mexico and the iconic Ringling Bridge. The kitchen is...
$4,000,000
Subdivision: The Ritz-Carlton Residences, Sarasota
3
Beds
3F11/2
Baths
3,095
Sq.Ft.
2018
Year Built
124
Days on Site
A4458390
MLS
Under Construction. A once in a lifetime opportunity to own the highest remaining Armand floor plan in the building. Offering expansive floor to ceiling views West, East and South. The Armand floor...
$3,999,999
Subdivision: Paradise Shores
5
Beds
5F11/2
Baths
5,014
Sq.Ft.
2019
Year Built
316
Days on Site
A4442067
MLS
Newly built. This coastal residence captivates with its impeccably designed d cor and outdoor living spaces in a scenic waterfront setting only seconds to the open waters of Sarasota Bay. Located...
$3,890,000
Subdivision: Sapphire Shores
3
Beds
3F11/2
Baths
5,099
Sq.Ft.
2016
Year Built
212
Days on Site
A4450740
MLS
Lavishly embellished with Old-World authenticity, this Waterfront estate replicates the grandeur of a 17th century Tuscan farmhouse. Artistic beauty blends with panoramic water views in a custom home...
$3,849,000
Subdivision: Bay Point Park 2
4
Beds
3F11/2
Baths
3,407
Sq.Ft.
2013
Year Built
485
Days on Site
A4425602
MLS
Tranquil, private and in the heart of it all! Situated on the widest banks of the Hudson Bayou in Downtown Sarasota this remarkable custom home will simply take your breath away. Through the...
$3,800,000
Subdivision: The Residences
3
Beds
3F11/2
Baths
4,276
Sq.Ft.
2001
Year Built
98
Days on Site
A4461520
MLS
One of only 4 Penthouses on top of the Ritz-Carlton Residences with amazing views of Sarasota Bay and downtown Sarasota! This penthouse has beautiful wood floors and custom wall coverings and a...
$3,790,000
Subdivision: Pine Shores Estates
5
Beds
6
Baths
6,878
Sq.Ft.
1992
Year Built
218
Days on Site
A4449708
MLS
Unobstructed bay views and endless sunsets are just the beginning for this incredible custom estate. Completely walled and gated, this Bayfront home is sited at the end of a quiet tree-lined street...

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.

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