Historic and Charming Florida

West of the Trail

Situated in Sarasota, this revered area is dubbed "West of the Trail" and simply refers to any properties lying to the west of Tamiami Trail (Route 41). This historic area, comprising cherished locales, embodies elegance and heritage. Residents here relish waterfront residences and effortless access to downtown Sarasota's cultural offerings, high-end shopping, and Siesta Key Public Beach.


West Of The Trail, Sarasota Real Estate Statistics

Average Price $1.5M
Lowest Price $1K
Highest Price $26.4M
Total Listings 496
Avg. Days On Market 116
Avg. Price/SQFT $535

Property Types (active listings)

Search West Of The Trail Real Estate Listings

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New
6742 Bowline Drive, SARASOTA

$499,999

6742 Bowline Drive, SARASOTA

GULF GATE 2 Beds 2 Baths 1,444 SqFt 0 DOM Residential MLS® # A4685028
New
1330 S Jefferson Avenue, SARASOTA

$785,000

1330 S Jefferson Avenue, SARASOTA

RUSTIC LODGE 2 3 Beds 2 Baths 1,716 SqFt 0 DOM Residential MLS® # A4685616
New
6338 Beechwood Avenue, SARASOTA

$589,000

6338 Beechwood Avenue, SARASOTA

EMERALD HARBOR 3 Beds 2 Baths 1,506 SqFt 0 DOM Residential MLS® # A4685783
New
1603 Bay Road, SARASOTA

$2,799,000

1603 Bay Road, SARASOTA

GRANADA 3 Beds 4 Baths 3,165 SqFt 0 DOM Residential MLS® # A4685828
New Open House
3225 Gulf Watch Court, SARASOTA

$420,000

3225 Gulf Watch Court, SARASOTA

GULF GATE GLEN 2 Beds 2 Baths 1,216 SqFt 0 DOM Residential
Sat, Mar 14th, 2026 @ 2pm - 4pm
MLS® # TB8483842
New
4360 Swift Road, SARASOTA

$320,000

4360 Swift Road, SARASOTA

FOREST HILLS 2 Beds 2 Baths 1,139 SqFt 0 DOM Residential MLS® # A4684014
New
1920 Wisteria Street, SARASOTA

$1,450,000

1920 Wisteria Street, SARASOTA

DESOTA PARK 3 Beds 3 Baths 1,736 SqFt 0 DOM Residential MLS® # A4683653
New
3463 Bee Ridge Road 318, SARASOTA

$165,000

3463 Bee Ridge Road 318, SARASOTA

VILLAGE GREEN OF SARASOTA 2 Beds 2 Baths 900 SqFt 1 DOM Residential MLS® # A4685466
New
1633 Boathouse Circle 232, SARASOTA

$500,000

1633 Boathouse Circle 232, SARASOTA

PELICAN COVE XII 3 Beds 2 Baths 1,320 SqFt 1 DOM Residential MLS® # A4685633
New
1708 Glenhouse Drive 313, SARASOTA

$349,000

1708 Glenhouse Drive 313, SARASOTA

PELICAN COVE XIV 2 Beds 2 Baths 1,330 SqFt 1 DOM Residential MLS® # A4685645
New
1680 Starling Drive 101, SARASOTA

$345,000

1680 Starling Drive 101, SARASOTA

LANDINGS SOUTH VII 2 Beds 2 Baths 1,712 SqFt 1 DOM Residential MLS® # A4684814
New
1740 Assisi Drive, SARASOTA

$390,000

1740 Assisi Drive, SARASOTA

PORTOFINO ON THE BAY 5 Beds 5 Baths 3,357 SqFt 2 DOM Residential MLS® # A4685706
New
3024 Williamsburg Street, SARASOTA

$248,000

3024 Williamsburg Street, SARASOTA

GOLDEN ACRES 2ND ADD 2 Beds 2 Baths 837 SqFt 1 DOM Residential MLS® # C7521739
New
5420 Eagles Point Circle 106, SARASOTA

$625,000

5420 Eagles Point Circle 106, SARASOTA

EAGLES POINT AT THE LANDINGS 1 3 Beds 2 Baths 2,021 SqFt 2 DOM Residential MLS® # A4684787
New
4444 Swift Road 23, SARASOTA

$159,900

4444 Swift Road 23, SARASOTA

LUCAYA COUNTRY CLUB VILLAGE 2 Beds 1 Bath 825 SqFt 1 DOM Residential MLS® # A4685535
New
1794 Cunliff Lane, SARASOTA

$3,095,000

1794 Cunliff Lane, SARASOTA

BAY VIEW HEIGHTS ADD 4 Beds 3 Baths 3,377 SqFt 2 DOM Residential MLS® # A4685523
New
1504 S Lodge Drive, SARASOTA

$6,990,000

1504 S Lodge Drive, SARASOTA

CHEROKEE LODGE 4 Beds 4 Baths 5,450 SqFt 2 DOM Residential MLS® # A4683855
New
2749 Orchid Oaks Drive 302, SARASOTA

$260,000

2749 Orchid Oaks Drive 302, SARASOTA

ORCHID OAKS I 2 Beds 2 Baths 1,365 SqFt 2 DOM Residential MLS® # A4685445
New
1511 Pelican Point Drive Ba180, SARASOTA

$499,800

1511 Pelican Point Drive Ba180, SARASOTA

PELICAN COVE VII 2 Beds 2 Baths 1,368 SqFt 2 DOM Residential MLS® # A4679440
New
2208 Shawnee Street, SARASOTA

$315,000

2208 Shawnee Street, SARASOTA

PHILLIPPI PARK 2 Beds 1 Bath 1,050 SqFt 2 DOM Residential MLS® # A4684985
New Open House
2920 Captiva Drive, SARASOTA

$585,000

2920 Captiva Drive, SARASOTA

GULF GATE WOODS 4 Beds 2 Baths 1,905 SqFt 3 DOM Residential
Thu, Mar 12th, 2026 @ 4pm - 6pm
MLS® # A4685319

West of the Trail, Sarasota Real Estate Info

Welcome to the prestigious and historically rich enclave of West of the Trail real estate, an esteemed area within Sarasota known for its luxurious residences and classical Florida charm. Here, nestled along the serene waterfront, homes range from $400,000 to multi-million-dollar estates, offering captivating views of Sarasota Bay and the Intracoastal Waterway.

This coveted neighborhood encompasses the revered historical districts of Cherokee ParkHarbor AcresMcClellan ParkDesota Park, The Landings and more. Each neighborhood boasts unique character, from stately mansions to picturesque residences, blending elegance with old-world Florida charm.

Within this enchanting area, discover exquisite homes in a variety of gated communities and exclusive 55+ neighborhoods. From contemporary, ranch-style dwellings to Mediterranean villas, these residences offer not just luxury but also proximity to Siesta Key Public Beach, shopping districts, and the charming downtown Sarasota. For those seeking comfort and style, explore condominium complexes and communities that serve as havens of refined living, boasting thoughtfully updated interiors and upscale amenities.

Professionals and families alike relish the seamless fusion of downtown proximity and the tranquil allure of old Florida living. The narrow, winding streets adorned with historic homes exude a nostalgic ambiance, often drawing comparisons to the classic architecture of northern and New England homes.

West of the Trail stands as a preferred choice, especially among medical professionals, owing to its close proximity to the esteemed Sarasota Memorial Hospital. This proximity has elevated the area's desirability, adding convenience for those in the medical field. Explore the diverse range of properties for sale in this enchanting area, where every residence tells a unique story amidst a backdrop of waterfront vistas and timeless elegance.  

Interested in learning more about West of the Trail Real Estate in Sarasota, FL? Contact us online or call 941-586-4790 for more information about buying and selling a home West of the Trail and other communities in the Sarasota area.

West of the Trail, Sarasota Highlights & Amenities

Situated west of Downtown Sarasota and US 41, the West of the Trail community stands as a testament to luxury living along Tamiami Trail. An upscale residential area, it encompasses the finest features Sarasota has to offer, attracting discerning individuals who seek a refined lifestyle.

As many of Florida's elite have chosen southwest Florida as their home, the surrounding neighborhoods, including West of the Trail, have evolved to meet their high standards. In this locale, public and private academies vie for community members and students, fostering a healthy academic rivalry that results in unparalleled excellence.

A leisurely stroll down picturesque Bungalow Hill connects you to downtown Sarasota, a vibrant hub with parks offering all the amenities you desire. The convenience of this location extends to easy access to shopping districts, galleries, eateries, hospitals, and more. Living West of the Trail provides a seamless blend of convenience and scenic beauty.

Moreover, the area is adorned with cultural gems and recreational havens. Residents can immerse themselves in the lush beauty of the Marie Selby Botanical Gardens or explore the diverse wildlife at the enchanting Sarasota Jungle Gardens. For art enthusiasts, the Ringling Museum of Art stands as a beacon of creativity, housing an impressive collection.

Entertainment options abound with the Van Wezel Performing Arts Hall, offering captivating performances that cater to varied tastes. Culinary delights await at renowned establishments like Connors Steak & Seafood, celebrated for its prime meats and fresh fish, and Veronica Fish & Oyster, a hotspot with delectable dishes served in a vibrant setting with a supper-club feel.

For those seeking panoramic views and nautical experiences, Marina Jack presents an opportunity to enjoy Sarasota Bay's beauty and book sightseeing cruises on-site. Additionally, a visit to the bustling commercial center of St. Armand’s Circle provides a phenomenal day out, offering an impressive directory of stores, restaurants, spas, and events.

The region's favorable weather complements its proximity to sparkling beaches and rich natural surroundings. Whether you're indulging in outdoor activities with family or immersing yourself in the community's culture and elegant shopping venues, West of the Trail offers a high quality of life in a unique neighborhood. Discover the epitome of luxury living in this exclusive Sarasota enclave.

Please explore the list above to view all the West of the Trail neighborhoods.  Click onto a neighborhood and read a description about the community and view all of the West of the Trail homes currently for sale! If you have any questions about finding an West of the Trail property please do not hesitate to either call Sara at 941-586-4790 or email her at Sara@SaraSellsSarasota.com  

West of the Trail, Sarasota FAQs

What makes West of the Trail a desirable place to live in Sarasota?

This area is highly sought after for its proximity to Sarasota Bay, waterfront properties, tree-lined streets, historic homes, and its vibrant cultural scene.

Are there notable attractions or points of interest in the West of the Trail area?

Absolutely, the area boasts attractions like the Ringling Museum, Selby Botanical Gardens, and easy access to downtown Sarasota's restaurants, theaters, and art galleries.

Is West of the Trail a family-friendly area?

Yes, it offers good schools, parks like Southside Village and Arlington Park, and a close-knit community atmosphere that families appreciate.

Are there any annual events or festivals that take place in this area?

The West of the Trail area often hosts events like the annual Art in the Park, holiday festivals, and neighborhood gatherings that contribute to its vibrant community spirit.

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