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 $1.4M
Lowest Price $110K
Highest Price $26.4M
Total Listings 373
Avg. Days On Market 129
Avg. Price/SQFT $495

Property Types (active listings)

Search West Of The Trail Real Estate Listings

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1636 Stickney Point Road 36-201, SARASOTA

$328,000

1636 Stickney Point Road 36-201, SARASOTA

CASTEL DEL MARE 2 Beds 2 Baths 1,016 SqFt 267 DOM Residential MLS® # N6141400
New
2839 Olympic Street, SARASOTA

$399,000

2839 Olympic Street, SARASOTA

SARASOTA VENICE CO 09 37 18 3 Beds 2 Baths 1,271 SqFt 1 DOM Residential MLS® # A4702845
New
1959 Hibiscus Street, SARASOTA

$2,220,000

1959 Hibiscus Street, SARASOTA

DESOTA PARK 3 Beds 3 Baths 2,720 SqFt 1 DOM Residential MLS® # A4702810
New
1909 Buccaneer Drive, SARASOTA

$350,000

1909 Buccaneer Drive, SARASOTA

PIRATES COVE - 1ST ADD 2 Beds 2 Baths 1,100 SqFt 0 DOM Residential MLS® # A4700673
New Open House
2840 S Shade Avenue, SARASOTA

$425,000

2840 S Shade Avenue, SARASOTA

LONG MEADOW 3 Beds 2 Baths 1,338 SqFt 1 DOM Residential
Thu, Aug 13th, 2026 @ 9am - 7pm
MLS® # O6432869
New
2557 Marblehead Drive, SARASOTA

$629,500

2557 Marblehead Drive, SARASOTA

MARBLEHEAD 2 Beds 2 Baths 2,095 SqFt 1 DOM Residential MLS® # TB8537962
New
2440 Arlington Street, SARASOTA

$1,150,000

2440 Arlington Street, SARASOTA

HYDE PARK HEIGHTS 3 Beds 2 Baths 1,859 SqFt 1 DOM Residential MLS® # A4702167
New Open House
7616 Cove Terrace, SARASOTA

$995,000

7616 Cove Terrace, SARASOTA

SOUTHPOINTE SHORES 3 Beds 2 Baths 3,324 SqFt 1 DOM Residential
Sun, Aug 16th, 2026 @ 1pm - 3pm
MLS® # A4699941
New
4380 Iola Drive, SARASOTA

$475,000

4380 Iola Drive, SARASOTA

GOLF ESTATES 3 Beds 2 Baths 1,725 SqFt 1 DOM Residential MLS® # A4702525
New
2828 Nassau Street, SARASOTA

$365,000

2828 Nassau Street, SARASOTA

VIRGINIA HEIGHTS SUB 3 Beds 2 Baths 1,367 SqFt 1 DOM Residential MLS® # A4702457
New
3214 N Seclusion Drive, SARASOTA

$749,500

3214 N Seclusion Drive, SARASOTA

SOUTH GATE 2 Beds 2 Baths 2,092 SqFt 2 DOM Residential MLS® # A4702540
New
1647 Brookhouse Court Br146, SARASOTA

$289,000

1647 Brookhouse Court Br146, SARASOTA

PELICAN COVE XVI 1 Bed 1 Bath 971 SqFt 1 DOM Residential MLS® # A4702587
New Open House
2420 Floyd Street, SARASOTA

$2,190,000

2420 Floyd Street, SARASOTA

RUSTIC LODGE 5 Beds 5 Baths 3,356 SqFt 2 DOM Residential
Fri, Aug 14th, 2026 @ 1pm - 4pm
MLS® # A4702530
New
1601 Pelican Point Drive 215, SARASOTA

$497,800

1601 Pelican Point Drive 215, SARASOTA

PELICAN COVE IX 3 Beds 2 Baths 1,320 SqFt 2 DOM Residential MLS® # A4701578
New
1647 Siesta Drive, SARASOTA

$1,690,000

1647 Siesta Drive, SARASOTA

BAYVIEW 5 Beds 3 Baths 3,032 SqFt 2 DOM Residential MLS® # A4702256
New
2763 Woodgate Lane 104, SARASOTA

$143,500

2763 Woodgate Lane 104, SARASOTA

PINEWOOD VILLAGE II 2 Beds 2 Baths 874 SqFt 3 DOM Residential MLS® # A4699725
New
3457 Clark Road 255, SARASOTA

$175,000

3457 Clark Road 255, SARASOTA

SIENNA 2 Beds 2 Baths 1,020 SqFt 4 DOM Residential MLS® # A4701296
New
Southwood Street, SARASOTA

$410,000

Southwood Street, SARASOTA

FLORENCE 0 Beds 0 Baths 0 SqFt 5 DOM Land MLS® # A4702388
New
Southwood Street, SARASOTA

$410,000

Southwood Street, SARASOTA

FLORENCE 0 Beds 0 Baths 0 SqFt 5 DOM Land MLS® # A4702380
New
Tidewood Avenue, SARASOTA

$3,300,000

Tidewood Avenue, SARASOTA

BAYWOOD COLONY WESTPORT SEC 2 0 Beds 0 Baths 0 SqFt 4 DOM Land MLS® # A4702296
New
3413 Clark Road 114, SARASOTA

$159,000

3413 Clark Road 114, SARASOTA

SIENNA 1 Bed 1 Bath 768 SqFt 5 DOM Residential MLS® # A4702273

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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