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 $120K
Highest Price $26.4M
Total Listings 364
Avg. Days On Market 123
Avg. Price/SQFT $493

Property Types (active listings)

Search West Of The Trail Real Estate Listings

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New
2410 Valencia Drive, SARASOTA

$587,500

2410 Valencia Drive, SARASOTA

SOUTH GATE 2 Beds 2 Baths 1,349 SqFt 1 DOM Residential MLS® # A4705120
New Open House
2350 Loma Linda Street, SARASOTA

$479,000

2350 Loma Linda Street, SARASOTA

LOMA LINDA PARK 3 Beds 2 Baths 1,352 SqFt 0 DOM Residential
Sat, Sep 5th, 2026 @ 10am - 3pm
MLS® # A4704449
New
1608 Stickney Point Road 8-107, SARASOTA

$489,900

1608 Stickney Point Road 8-107, SARASOTA

CASTEL DEL MARE 2 Beds 2 Baths 1,016 SqFt 0 DOM Residential MLS® # A4703471
New
1585 South Drive, SARASOTA

$2,300,000

1585 South Drive, SARASOTA

CHEROKEE PARK 3 Beds 4 Baths 2,764 SqFt 0 DOM Residential MLS® # A4704763
New
7219 Cloister Drive 202, SARASOTA

$224,900

7219 Cloister Drive 202, SARASOTA

GULF GATE GARDENS 2 Beds 2 Baths 914 SqFt 1 DOM Residential MLS® # N6145560
New
5544 Dinah Lane, SARASOTA

$1,650,000

5544 Dinah Lane, SARASOTA

TERRA BEA SUB 6 Beds 5 Baths 4,433 SqFt 1 DOM Residential MLS® # A4704943
New Open House
3141 Regatta Circle, SARASOTA

$459,000

3141 Regatta Circle, SARASOTA

GULF GATE 2 Beds 2 Baths 1,299 SqFt 1 DOM Residential
Sun, Sep 6th, 2026 @ 1am - 3pm
MLS® # A4704993
New
2720 Goldenrod Street, SARASOTA

$549,900

2720 Goldenrod Street, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,547 SqFt 1 DOM Residential MLS® # TB8545219
2163 Waldemere Street, SARASOTA

$2,290,000

2163 Waldemere Street, SARASOTA

LOMA LINDA PARK RESUB 5 Beds 6 Baths 3,334 SqFt 315 DOM Residential MLS® # A4669073
2305 Temple Street, SARASOTA

$2,149,000

2305 Temple Street, SARASOTA

LOMA LINDA PARK 5 Beds 7 Baths 3,386 SqFt 305 DOM Residential MLS® # A4670467
New Open House
5627 Ashton Way 5627, SARASOTA

$339,000

5627 Ashton Way 5627, SARASOTA

ASHTON LAKES 09 2 Beds 2 Baths 1,232 SqFt 1 DOM Residential
Sun, Sep 6th, 2026 @ 1pm - 3pm
MLS® # A4704822
New
2121 Palm Terrace, SARASOTA

$594,900

2121 Palm Terrace, SARASOTA

HARBOR OAKS 3 Beds 3 Baths 1,681 SqFt 1 DOM Residential MLS® # A4704777
New
2161 Inner Cass Circle, SARASOTA

$549,750

2161 Inner Cass Circle, SARASOTA

SIESTA HEIGHTS 4 Beds 2 Baths 1,959 SqFt 2 DOM Residential MLS® # TB8544374
New
2370 Bahia Vista Street, SARASOTA

$349,000

2370 Bahia Vista Street, SARASOTA

LOMA LINDA PARK 3 Beds 2 Baths 957 SqFt 2 DOM Residential MLS® # A4704791
New
1761 Sandalwood Drive, SARASOTA

$1,979,000

1761 Sandalwood Drive, SARASOTA

SOUTHPOINTE SHORES 3 Beds 2 Baths 1,863 SqFt 2 DOM Residential MLS® # A4703427
New
1960 Boyce Street, SARASOTA

$3,895,000

1960 Boyce Street, SARASOTA

HARTSDALE 4 Beds 5 Baths 4,033 SqFt 2 DOM Residential MLS® # A4704619
New
2347 Tangerine Drive, SARASOTA

$675,000

2347 Tangerine Drive, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,446 SqFt 2 DOM Residential MLS® # A4704738
Open House
3502 Bahia Vista Street, SARASOTA

$1,199,000

3502 Bahia Vista Street, SARASOTA

HOMECROFT 7 Beds 7 Baths 3,432 SqFt 790 DOM Residential
Sat, Sep 5th, 2026 @ 1pm - 4pm
MLS® # A4615828
New
2462 Missara Lane, SARASOTA

$2,385,000

2462 Missara Lane, SARASOTA

SHORELINE 4 Beds 5 Baths 3,130 SqFt 4 DOM Residential MLS® # A4704478
New
3365 Cross Creek Dr 3365, SARASOTA

$240,000

3365 Cross Creek Dr 3365, SARASOTA

CROOKED CREEK SEC 7 2 Beds 2 Baths 1,027 SqFt 3 DOM Residential MLS® # A4704481
New
2695 S East Avenue, SARASOTA

$499,000

2695 S East Avenue, SARASOTA

SOUTH SIDE PARK 4 Beds 2 Baths 2,100 SqFt 6 DOM Residential MLS® # O6437558

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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