West of the Trail

Sarasota Homes for Sale

Waterfront Homes, Luxury Homes and Condos

West of the Trail are the neighborhoods "west" of 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...

Highlighting the area near Morton's Market are waterfront homes on Sarasota Bay in Harbor Acres and Cherokee Park. Magnificent mansions are now on some of the canal and bay lots and have replaced older Florida homes adding exceptional new styling, deep water yacht slips and top of the line amenities.  Show Less...

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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Current Homes and Condos for Sale - West of the Trail

Showing 1-10 of 398  | 
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$6,249,000
Bedrooms: 5
Baths: 6
Approx Sq Ft: 5738
1333 Vista Drive
Sarasota, FL 34239
MLS #: O5446820
Subdivision: harbor acres
Under construction. Inspired by the understated luxury of a Caribbean villa, this brand new, two-story home by Modus Custom Residences offers serene water...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$6,185,888
Bedrooms: 5
Baths: 6
Approx Sq Ft: 5926
1001 Tocobaga Lane
Sarasota, FL 34236
MLS #: A4171509
Subdivision: tocobaga bay
Savor breathtaking panoramic views of Sarasota Bay from this newly built home set on one of the most cherished waterfront lots behind the gates of beautiful...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$5,600,000
Bedrooms: 4
Baths: 5
Approx Sq Ft: 5169
1121 Ritz Carlton Drive #PH 1803 (Pending)
Sarasota, FL 34236
MLS #: A4160397
Subdivision: ritz carlton tower residences
Pre-Construction to be built. Now taking reservations. Imagine a penthouse not only defined by sophisticated style and luxurious finishes, but equipped to...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,975,000
Bedrooms: 4
Baths: 9
Approx Sq Ft: 6883
1717 Southpointe Drive
Sarasota, FL 34231
MLS #: A4155867
Subdivision: southpointe shores
Spectacular sunsets await at this inspired custom designed home presenting magnificent water vistas from every room. Boating and car enthusiasts will delight...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,750,000
Bedrooms: 5
Baths: 7
Approx Sq Ft: 6710
3544 San Remo Terrace
Sarasota, FL 34239
MLS #: A4174958
Subdivision: san remo estates
Stunning Sarasota waterfront property in prime location. Situated in desirable West-of-Trail San Remo Estates, this custom built 6,700 sq. ft. home offers 2...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,490,000
Bedrooms: 5
Baths: 8
Approx Sq Ft: 7434
2309 Alameda Avenue
Sarasota, FL 34234
MLS #: A4177492
Subdivision: sarasota bay park
You'll feel as though the sun sets daily just for you when you make this private gated paradise your own. Set far from the road, a paver drive leads past...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,295,000
Bedrooms: 4
Baths: 6
Approx Sq Ft: 5893
1394 Harbor Drive
Sarasota, FL 34239
MLS #: A4153493
Subdivision: harbor acres
Enter the grand foyer of this impressive Harbor Acres home and be mesmerized by the sun sparkling on the protected waters of Sarasota’s most coveted...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$3,995,000
Bedrooms: 3
Baths: 4
Approx Sq Ft: 4373
1352 Harbor Drive
Sarasota, FL 34239
MLS #: A4174153
Subdivision: harbor acres
Located in Sarasota’s favorite mainland bayside neighborhood of Harbor Acres, this gracious Traditional home enjoys the best of both worlds…Bay, City and...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$3,995,000
Bedrooms: 5
Baths: 7
Approx Sq Ft: 5313
4223 Bay Shore Road (Pending)
Sarasota, FL 34234
MLS #: A4178960
Subdivision: indian beach
Capture the magic of old world Sarasota that exudes from every inch of this 1940's estate property located on Sapphire Shores in historic Indian Beach....
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$3,995,000
Bedrooms: 4
Baths: 3
Approx Sq Ft: 4315
1535 Bay Point Drive (Pending)
Sarasota, FL 34236
MLS #: A4182276
Subdivision: bay point park
Mere minutes from downtown Sarasota and seconds from the open Bay, this West-of-Trail waterfront residence enchants with a spectacular Selby Gardens view and...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
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West of Trail Homes

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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