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 April 22, 2021
91
Listed
114
Avg. DOM
$548.52
Avg. $ / Sq.Ft.
$1,160,000
Med. List Price
91 Properties
Page 1 of 8
$18,000,000
Subdivision: Harbor Acres Sec 2
3
Beds
4F21/2
Baths
8,452
Sq.Ft.
2012
Year Built
60
Days on Site
A4491997
MLS
Rarely has such an unprecedented opportunity come available for the most discerning buyer in search of a private waterfront gated estate in Harbor Acres, a premier established neighborhood set on...
$6,795,000
Subdivision: Indian Beach-Sapphire Shores
5
Beds
4F11/2
Baths
6,172
Sq.Ft.
2006
Year Built
10
Days on Site
A4497369
MLS
The gorgeous, lush landscaping welcoming you to this five-bedroom direct bayfront estate is tied to its sought-after Indian Beach locale with a winding curved driveway and private gated entry. Built...
$6,650,000
Subdivision: Not Part Of A Subdivision
6
Beds
6F21/2
Baths
9,052
Sq.Ft.
1983
Year Built
67
Days on Site
A4491567
MLS
Herein lies the best waterfront opportunity that you will find in Sarasota. The seller is offering a flexible sales structure to include subdividing the parcel with the waterfront lot/home priced at...
$6,490,000
Subdivision: Baywinds Estates
4
Beds
4F31/2
Baths
5,110
Sq.Ft.
2018
Year Built
171
Days on Site
A4482748
MLS
This magnificent waterfront estate sits on over 300 feet of shoreline on Little Sarasota Bay and offers sweeping views from nearly every room. This custom home was built in 2018 and offers...
$5,975,000
Subdivision: The Tower Residences
4
Beds
4F11/2
Baths
4,668
Sq.Ft.
2003
Year Built
240
Days on Site
A4476458
MLS
Luxury. Incredible Views. Impeccable Service. Privacy. This stunning Ritz-Carlton Penthouse with exceptional appointments sits high above Sarasota Bay, offering sparkling water views from every...
$5,395,000
Subdivision: Oyster Bay Estates
5
Beds
5F11/2
Baths
6,739
Sq.Ft.
2016
Year Built
45
Days on Site
A4493808
MLS
One or more photo(s) has been virtually staged. Spectacular one-of-a-kind location and privacy close to downtown Sarasota and minutes from the gorgeous award-winning Siesta Key beach. A truly...
$4,495,000
Subdivision: Stillwater On The Bay
4
Beds
5F11/2
Baths
5,093
Sq.Ft.
2004
Year Built
81
Days on Site
A4490114
MLS
Come live the Florida lifestyle to its fullest in this magnificent Mediterranean style waterfront home located behind the gates of the much sought after enclave of Stillwater on the Bay. Luxurious,...
$4,399,000
Subdivision: Poinsettia Park
5
Beds
7F21/2
Baths
9,492
Sq.Ft.
2006
Year Built
254
Days on Site
A4475067
MLS
Transport yourself to the countryside of France where you may ensconce yourself behind the ivy-covered walls of this gated multi-level French chateau amidst the most glorious selection of plantings...
$4,100,000
Subdivision: Paradise Shores
4
Beds
4
Baths
4,942
Sq.Ft.
1956
Year Built
43
Days on Site
T3294850
MLS
LISTING UPDATE: Brand New Barrel Tile Roof 4/2021. This is a rare opportunity for waterfront living in highly sought Paradise Shores. For the boating and watersports enthusiast, there is 190 feet of...
$3,700,000
Subdivision: The Residences
3
Beds
4F21/2
Baths
4,640
Sq.Ft.
2001
Year Built
297
Days on Site
A4471072
MLS
Step into this stylish and expansive Ritz-Carlton Residence that offers captivating views at every turn overlooking Sarasota Bay. With 4640 square feet of exquisite living space, this unique home...
$3,650,000
Subdivision: The Tower Residences
3
Beds
3
Baths
3,751
Sq.Ft.
2003
Year Built
445
Days on Site
A4458742
MLS
The most sought-after luxury condominium in Sarasota, this inspiring residence at The Ritz-Carlton guarantees world-class signature service and amenities overlooking Sarasota Bay in culturally-rich...
$3,650,000
Subdivision: Oyster Bay Estates
5
Beds
5F21/2
Baths
6,963
Sq.Ft.
1968
Year Built
3
Days on Site
A4498214
MLS
**ALMOST 1/2 ACRE BAYFRONT ON ROBERTS BAY ADJACENT TO INTERCOASTAL WATERWAY WITH 100 FEET OF SEAWALL, BOAT DOCK, AND BOAT LIFT.** THIS ESTATE SIZE HOME(6963sf) located in the beloved "Oyster Bay"...

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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