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

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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 This custom residence offers serene water views...
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.
$5,595,000
Bedrooms: 5
Baths: 7
Approx Sq Ft: 7074
1540 Hillview Drive
Sarasota, FL 34239
MLS #: A4197272
Subdivision: harbor acres
Set in a commanding waterfront location on Hillview Drive, one of the most prized addresses in Sarasota, this simply sublime home is bestowed with scenic...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,890,000
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. Prime location in desirable West-of-Trail San Remo Estates, this custom built 6,700 sq. ft. home offers 2 Master Suites...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,695,000
Bedrooms: 5
Baths: 6
Approx Sq Ft: 5491
1505 Hillview Drive
Sarasota, FL 34239
MLS #: A4197135
Subdivision: harbor acres
Designer finishes, thoughtful decor and custom construction built to the highest standards are the perfect introduction to this remarkable coastal home in...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,375,000
Bedrooms: 4
Baths: 3
Approx Sq Ft: 3783
1479 Bay Point Drive
Sarasota, FL 34236
MLS #: A4194135
Subdivision: bay point park 2
Rare opportunity to purchase LAND in one of the most exclusive, waterfront, west of trail, neighborhoods. This Bay Point gem is on the market for the first...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,269,800
Bedrooms: 5
Baths: 8
Approx Sq Ft: 7434
2309 Alameda Avenue
Sarasota, FL 34234
MLS #: A4177492
Subdivision: sarasota bay park
Treasured for both its natural beauty and being a three-minute drive from downtown Sarasota, this private estate has 135-feet waterfront on north Sarasota Bay....
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$4,000,000
Bedrooms: 4
Baths: 5
Approx Sq Ft: 4848
100 Ritz-Carlton Circle #403
Sarasota, FL 34236
MLS #: A4195719
Subdivision: ritz carlton tower residences
Pre-construction. To be built. The Ritz-Carlton Residences, Sarasota. This iconic 18 story residential tower featuring 72 luxury residences offering the most...
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 home enjoys the best of both worlds…Bay, City and Bridge views...
Contact Annette Smith at (941) 504-3922 to inquire about this property.
$3,993,000
Bedrooms: 5
Baths: 6
Approx Sq Ft: 6101
1344 Harbor Drive
Sarasota, FL 34239
MLS #: A4187925
Subdivision: harbor acres
A gorgeous waterfront estate located in the desirable Bayfront community of Harbor Acres—Sarasota’s most coveted location.Originally constructed in 1949,...
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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