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 $120K
Highest Price $18M
Total Listings 407
Avg. Days On Market 102
Avg. Price/SQFT $530

Property Types (active listings)

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New
2430 Sunnyside Lane, SARASOTA

$475,000

2430 Sunnyside Lane, SARASOTA

SOUTH GATE 2 Beds 2 Baths 1,446 SqFt 0 DOM Residential MLS® # A4609913
New
1680 Assisi Drive 14, SARASOTA

$297,500

1680 Assisi Drive 14, SARASOTA

PORTOFINO ON THE BAY 0 Beds 0 Baths 0 SqFt 0 DOM Land MLS® # T3525115
New
2510 Parma Street, SARASOTA

$520,000

2510 Parma Street, SARASOTA

RENICK SUB 3 Beds 2 Baths 1,462 SqFt 0 DOM Residential MLS® # O6203283
New
2157 Wisteria Street, SARASOTA

$2,049,975

2157 Wisteria Street, SARASOTA

GROVE LAWN REP 4 Beds 3 Baths 3,220 SqFt 0 DOM Residential MLS® # A4606954
New
2439 Loma Linda Street, SARASOTA

$425,000

2439 Loma Linda Street, SARASOTA

RUSTIC LODGE 2 3 Beds 2 Baths 1,238 SqFt 1 DOM Residential MLS® # A4609415
New
2534 Grove Street, SARASOTA

$3,240,000

2534 Grove Street, SARASOTA

SOUTH GATE 6 Beds 7 Baths 4,615 SqFt 1 DOM Residential MLS® # A4609226
New
2532 Fruit Tree, SARASOTA

$2,750,000

2532 Fruit Tree, SARASOTA

SOUTHGATE 5 Beds 6 Baths 3,931 SqFt 1 DOM Residential MLS® # A4609225
New
2124 Clematis Place, SARASOTA

$2,960,000

2124 Clematis Place, SARASOTA

SOUTH GATE 5 Beds 6 Baths 3,574 SqFt 1 DOM Residential MLS® # A4609224
New
1671 Arlington Street, SARASOTA

$3,775,000

1671 Arlington Street, SARASOTA

LEWIS COMBS SUB 4 Beds 5 Baths 3,250 SqFt 1 DOM Residential MLS® # A4609222
New
7614 Peninsular Drive, SARASOTA

$3,200,000

↓ $316,800,000

7614 Peninsular Drive, SARASOTA

SOUTHPOINTE SHORES 4 Beds 3 Baths 2,748 SqFt 1 DOM Residential MLS® # A4609710
New
2420 Portland Street, SARASOTA

$560,000

2420 Portland Street, SARASOTA

PHILLIPPI CREST WADE & AVERYS ADD 03 3 Beds 1 Bath 839 SqFt 2 DOM Residential MLS® # A4609590
New
2240 Valencia Drive, SARASOTA

$575,000

2240 Valencia Drive, SARASOTA

SOUTH GATE UNIT 2 3 Beds 2 Baths 1,494 SqFt 2 DOM Residential MLS® # A4608893
New
1519 Pelican Point Drive 187, SARASOTA

$530,000

1519 Pelican Point Drive 187, SARASOTA

PELICAN COVE VII 2 Beds 2 Baths 1,460 SqFt 2 DOM Residential MLS® # A4609376
New
1680 Assisi Drive 13, SARASOTA

$297,500

1680 Assisi Drive 13, SARASOTA

PORTOFINO ON THE BAY 0 Beds 0 Baths 0 SqFt 2 DOM Land MLS® # T3523276
New
1882 Vamo Drive, SARASOTA

$449,000

1882 Vamo Drive, SARASOTA

VAMO 3RD ADD TO 3 Beds 2 Baths 1,592 SqFt 2 DOM Residential MLS® # A4608820
New
1930 Wisteria Street, SARASOTA

$1,790,000

1930 Wisteria Street, SARASOTA

DESOTA PARK 4 Beds 4 Baths 3,060 SqFt 2 DOM Residential MLS® # A4608180
New
2619 Jamaica Street, SARASOTA

$369,000

2619 Jamaica Street, SARASOTA

BAHAMA HEIGHTS 3 Beds 2 Baths 1,418 SqFt 4 DOM Residential MLS® # A4609396
New
2163 Hillview Street, SARASOTA

$2,975,000

2163 Hillview Street, SARASOTA

LA LINDA TERRACE 6 Beds 6 Baths 3,225 SqFt 4 DOM Residential MLS® # A4609218
New
2616 Britannia Road, SARASOTA

$425,000

2616 Britannia Road, SARASOTA

PHILLIPPI GARDENS 15 3 Beds 2 Baths 1,476 SqFt 4 DOM Residential MLS® # A4609584
New
2246 Fiesta Drive, SARASOTA

$1,350,000

2246 Fiesta Drive, SARASOTA

RIDGEWOOD 4 Beds 4 Baths 2,471 SqFt 5 DOM Residential MLS® # U8241479
New
1800 Robinhood Street, SARASOTA

$1,299,000

1800 Robinhood Street, SARASOTA

SOUTH HIGHLAND AMD OF 4 Beds 4 Baths 2,825 SqFt 5 DOM Residential MLS® # A4609542

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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