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 $1.3M
Lowest Price $116K
Highest Price $26.4M
Total Listings 379
Avg. Days On Market 144
Avg. Price/SQFT $484

Property Types (active listings)

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2348 Doud Street, SARASOTA

$365,000

2348 Doud Street, SARASOTA

PINEHURST PARK REP OF 3 Beds 1 Bath 1,118 SqFt 81 DOM Residential MLS® # A4696579
New
2629 Jamaica Street 1, SARASOTA

$349,000

2629 Jamaica Street 1, SARASOTA

BAHAMA HEIGHTS 2 Beds 2 Baths 1,210 SqFt 0 DOM Residential MLS® # A4709244
New
2851 Hardee Drive, SARASOTA

$574,900

2851 Hardee Drive, SARASOTA

GULF GATE WOODS 4 Beds 2 Baths 2,110 SqFt 2 DOM Residential MLS® # TB8556877
New
5424 America Drive, SARASOTA

$1,350,000

5424 America Drive, SARASOTA

PHILLIPPI GARDENS 08 3 Beds 3 Baths 1,706 SqFt 3 DOM Residential MLS® # A4709112
New
2476 Floyd Street, SARASOTA

$1,749,000

2476 Floyd Street, SARASOTA

RUSTIC LODGE 4 Beds 4 Baths 2,389 SqFt 3 DOM Residential MLS® # A4709087
2534 Waneta Drive, SARASOTA

$475,000

2534 Waneta Drive, SARASOTA

PHILLIPPI GARDENS 06 3 Beds 2 Baths 1,667 SqFt 199 DOM Residential MLS® # A4678870
1428 Pine Bay Drive, SARASOTA

$1,915,000

1428 Pine Bay Drive, SARASOTA

PINE BAY 4 Beds 4 Baths 2,820 SqFt 127 DOM Residential MLS® # A4695249
Open House
2546 Loma Linda Street, SARASOTA

$899,000

2546 Loma Linda Street, SARASOTA

RUSTIC LODGE 3 Beds 3 Baths 1,779 SqFt 17 DOM Residential
Sat, Oct 17th, 2026 @ 1pm - 4pm
MLS® # A4707307
New
1757 Mova Street, SARASOTA

$329,000

1757 Mova Street, SARASOTA

VAMO 2ND ADD TO 3 Beds 1 Bath 1,114 SqFt 6 DOM Residential MLS® # A4708228
3624 S Lockwood Ridge Road, SARASOTA

$1,375,000

3624 S Lockwood Ridge Road, SARASOTA

SOUTH GATE 4 Beds 4 Baths 4,013 SqFt 48 DOM Residential MLS® # A4703672
Open House
2404 Bispham Road, SARASOTA

$575,000

2404 Bispham Road, SARASOTA

GULF GATE 3 Beds 2 Baths 1,719 SqFt 73 DOM Residential
Fri, Oct 16th, 2026 @ 10am - 2pm
MLS® # A4701601
3453 Clark 252, SARASOTA

$134,900

3453 Clark 252, SARASOTA

SIENNA PARK CONDO 1 Bed 1 Bath 768 SqFt 111 DOM Residential MLS® # A4697775
2207 Wisteria Street, SARASOTA

$1,995,250

2207 Wisteria Street, SARASOTA

GREENWICH 4 Beds 4 Baths 3,120 SqFt 222 DOM Residential MLS® # A4683417
2513 Croton Avenue, SARASOTA

$619,000

2513 Croton Avenue, SARASOTA

SOUTH GATE MANOR 3 Beds 3 Baths 1,604 SqFt 157 DOM Residential MLS® # A4692136
3286 Brunswick Lane 704, SARASOTA

$239,900

3286 Brunswick Lane 704, SARASOTA

SOUTH GATE VILLAGE GREEN 07 2 Beds 2 Baths 1,563 SqFt 44 DOM Residential MLS® # A4704355
1871 Siesta Drive, SARASOTA

$669,999

1871 Siesta Drive, SARASOTA

HARTLAND PARK 0 Beds 0 Baths 0 SqFt 54 DOM Land MLS® # A4703295
1515 Pelican Point Drive Ba185, SARASOTA

$529,800

1515 Pelican Point Drive Ba185, SARASOTA

PELICAN COVE VII 2 Beds 2 Baths 1,368 SqFt 150 DOM Residential MLS® # A4692882
1840 Rita Street, SARASOTA

$375,000

1840 Rita Street, SARASOTA

MEAD HELEN D 2 Beds 2 Baths 1,039 SqFt 45 DOM Residential MLS® # A4703660
2719 Temple Street, SARASOTA

$550,000

2719 Temple Street, SARASOTA

ARLINGTON PARK 3 Beds 2 Baths 1,372 SqFt 70 DOM Residential MLS® # A4700567
Open House
1647 Siesta Drive, SARASOTA

$1,690,000

1647 Siesta Drive, SARASOTA

BAYVIEW 5 Beds 3 Baths 3,032 SqFt 17 DOM Residential
Fri, Oct 16th, 2026 @ 1pm - 4pm
MLS® # A4707313
New
1870 Mova Street, SARASOTA

$395,000

1870 Mova Street, SARASOTA

GIBSON BESSIE P SUB 3 Beds 2 Baths 1,495 SqFt 6 DOM Residential MLS® # A4708627

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 Park, Harbor Acres, McClellan Park, Desota 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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