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 January 21, 2020
325
Listed
155
Avg. DOM
$433.02
Avg. $ / Sq.Ft.
$895,000
Med. List Price
325 Properties
Page 1 of 28
$7,500,000
Subdivision: Harbor Acres
4
Beds
3F11/2
Baths
4,187
Sq.Ft.
1954
Year Built
272
Days on Site
A4434317
MLS
On Sarasota's shoreline and most desired address within Harbor Acres, discover unequivocal excellence - whether building new or enjoying the current and impeccably updated residence. Surrounded by...
$6,995,000
Subdivision: Harbor Acres
5
Beds
4F21/2
Baths
5,244
Sq.Ft.
1999
Year Built
77
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...
$6,500,000
Subdivision: Cedar Cove
6
Beds
6F31/2
Baths
10,554
Sq.Ft.
1990
Year Built
42
Days on Site
A4452913
MLS
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 elegance and coastal comfort. Just paces from...
$5,750,000
Subdivision: Owens
5
Beds
6F11/2
Baths
7,108
Sq.Ft.
1998
Year Built
66
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....
$4,900,000
Subdivision: The Ritz-Carlton Residences / Sarasota
4
Beds
5
Baths
4,855
Sq.Ft.
2019
Year Built
43
Days on Site
A4453647
MLS
Under Construction. The Worthington floor plan offers 4,855 square feet of living space. Soaring 11-foot ceilings provide breathtaking unobstructed water views of Sarasota Bay and the Gulf of Mexico....
$4,650,000
Subdivision: Oyster Bay Landings
4
Beds
4F21/2
Baths
5,889
Sq.Ft.
2006
Year Built
7
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
14
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...
Open 1/26
1807 Oleander Street Sarasota, FL 34239
$4,499,000
Subdivision: Poinsettia Park
7
Beds
7F21/2
Baths
9,492
Sq.Ft.
2006
Year Built
464
Days on Site
A4414354
MLS
Prepare to be Enchanted. Imagine being swept away to a vine-covered French Chateau nestled on a hillside in the Wine Country of France. Open your eyes and realize you are in this walled, gated estate...
$4,280,000
Subdivision: Whitakers
5
Beds
4F21/2
Baths
6,439
Sq.Ft.
1992
Year Built
14
Days on Site
A4414337
MLS
This gated waterfront estate is situated on an acre of gardens, ancient oaks and walkways directly on Sarasota Bay. Discover a rare combination of tranquility and location within the desirable Museum...
$4,272,000
Subdivision: Auteur Sarasota
3
Beds
3F11/2
Baths
3,898
Sq.Ft.
2020
Year Built
89
Days on Site
A4449720
MLS
Pre-Construction. To be built. To be built. Now accepting contracts. Auteur Sarasota, our city's next iconic tower residences conceived by local iconic developer, Jay Tallman. It begins with...
$4,225,000
Subdivision: Whitakers W H Prop
3
Beds
3F11/2
Baths
4,632
Sq.Ft.
1951
Year Built
97
Days on Site
A4449047
MLS
Experience seaside whimsey along Sarasota Bay where over 200' of waterfront splendor, majestic Oak trees, and unforgettable sunsets evoke daily inspiration and wonder. Envision a custom estate,...
$4,100,000
Subdivision: Paradise Shores
5
Beds
5F11/2
Baths
4,781
Sq.Ft.
2020
Year Built
161
Days on Site
A4443475
MLS
Under Construction. Perfectly sited on 123 feet of protected yacht basin and the 3rd house in from the open bay is another vision of beauty and functionality from notable luxury builder, Allegra...

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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