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 May 21, 2019
362
Listed
165
Avg. DOM
$432.88
Avg. $ / Sq.Ft.
$779,000
Med. List Price
362 Properties Found. Showing 1-12
Sort By:
1221 Hillview Drive
Sarasota, FL 34239
1221 Hillview Drive Sarasota, FL 34239
1 of 44
$7,500,000
Subdivision: Harbor Acres
BEDS
4
BATHS
4
SQ.FT.
4,187
BUILT
1954
ON SITE
27Days
MLS
A4434317
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...
929 Alameda Way
Sarasota, FL 34234
929 Alameda Way Sarasota, FL 34234
1 of 26
$6,350,000 ( $600,000 )
Subdivision: Owens
BEDS
5
BATHS
7
SQ.FT.
9,067
BUILT
1998
ON SITE
470Days
MLS
A4209083
Perfectly positioned on the shores of Sarasota Bay, this contemporary home is recognized by any and all who sail the waters between Longboat Key and the mainland. The stunning masterpiece is more...
2211 Alameda Avenue
Sarasota, FL 34234
2211 Alameda Avenue Sarasota, FL 34234
1 of 25
$5,750,000 ( $500,000 )
Subdivision: Sarasota Bay Park
BEDS
5
BATHS
6
SQ.FT.
6,822
BUILT
2010
ON SITE
428Days
MLS
A4213954
Casa de Familia, one of Sarasota's most beautiful bay front homes, is offered for purchase for the very first time. This exquisite family residence is masterfully nestled among majestic grand oaks...
1333 Vista Drive
Sarasota, FL 34239
1333 Vista Drive Sarasota, FL 34239
1 of 50
$5,749,000 ( $250,000 )
Subdivision: Harbor Acres
BEDS
5
BATHS
6
SQ.FT.
5,768
BUILT
2019
ON SITE
110Days
MLS
A4426157
Of all Sarasota's great neighborhoods, Harbor Acres is considered the best - best location, best waterfront, best appreciation, best pedigree, best neighbors. Residents love being part of the...
990 Blvd Of The Arts #1800
Sarasota, FL 34236
990 Blvd Of The Arts #1800 Sarasota, FL 34236
1 of 24
$5,670,000 ( $2,280,000 )
Subdivision: Beau Ciel
BEDS
4
BATHS
6
SQ.FT.
8,111
BUILT
2003
ON SITE
345Days
MLS
A4405592
Soaring above the waterfront and the evolutionary Sarasota skyline, the Penthouse at Beau Ciel takes the city living experience to panoramic new heights - quite literally. Expertly fusing the luxury,...
1100 Blvd Of The Arts Boulevard #18A
Sarasota, FL 34236
1100 Blvd Of The Arts Boulevard #18A Sarasota, FL 34236
1 of 6
$4,788,000
Subdivision: Auteur Sarasota
BEDS
3
BATHS
4
SQ.FT.
4,219
BUILT
2020
ON SITE
104Days
MLS
A4426669
Pre-Construction. To be built. Now Taking Reservations. Auteur Sarasota, our city's next iconic tower residences conceived by local iconic developer, Jay Tallman. It begins with spacious,...
200 Quay Commons #1003
Sarasota, FL 34236
200 Quay Commons #1003 Sarasota, FL 34236
1 of 15
$4,775,000
Subdivision: The Ritz-Carlton Residences / Sarasota
BEDS
4
BATHS
5
SQ.FT.
4,855
BUILT
2018
ON SITE
112Days
MLS
A4425686
Under Construction. This 10th floor Worthington floor plan offers 4,848 square feet of living space with 4 bedrooms, 5 baths and a den. Sit back and unwind on your terrace spanning 840 feet, glass...
3544 San Remo Terrace
Sarasota, FL 34239
3544 San Remo Terrace Sarasota, FL 34239
1 of 28
$4,750,000 ( $240,000 )
Subdivision: San Remo Estates
BEDS
5
BATHS
7
SQ.FT.
6,710
BUILT
2009
ON SITE
368Days
MLS
A4403580
Lake Tahoe came to Sarasota Bay in 2009...and they built a house together. This spectacular, custom-designed home offers 2 full Master Suites, each with their own private terrace, and 3 guest suites...
1509 S Lodge Drive
Sarasota, FL 34239
1509 S Lodge Drive Sarasota, FL 34239
1 of 30
$4,695,000 ( $300,000 )
Subdivision: Cherokee Park
BEDS
5
BATHS
5
SQ.FT.
5,800
BUILT
2005
ON SITE
197Days
MLS
A4416416
The spectacular location of this waterfront home is quite unique. Resting on nearly 2/3-acre of property at the end of a quiet cul-de-sac, just one parcel in from the point-lot location that...
1435 Hillview Drive
Sarasota, FL 34239
1435 Hillview Drive Sarasota, FL 34239
1 of 50
$4,595,000 ( $400,000 )
Subdivision: Harbor Acres
BEDS
3
BATHS
5
SQ.FT.
4,876
BUILT
1999
ON SITE
134Days
MLS
A4423245
Enter this grand Harbor Acres estate through antique wrought iron gates and proceed down the long winding paver driveway to this very private setting on 115 ft of protected yacht basin. The lushly...
1807 Oleander Street
Sarasota, FL 34239
1807 Oleander Street Sarasota, FL 34239
1 of 50
$4,499,000
Subdivision: Poinsettia Park
BEDS
7
BATHS
9
SQ.FT.
9,492
BUILT
2006
ON SITE
219Days
MLS
A4414354
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...
1404 Kenilworth Street
Sarasota, FL 34231
1404 Kenilworth Street Sarasota, FL 34231
1 of 43
$4,385,000 ( $210,000 )
Subdivision: Oyster Bay Landings
BEDS
4
BATHS
5
SQ.FT.
5,428
BUILT
2007
ON SITE
102Days
MLS
A4424301
Art you can live in! World renowned and acclaimed architect, Guy Peterson, designed another modern masterpiece of remarkable craftsmanship and pure minimalist aesthetic. It all began with a vision,...

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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