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 $99K
Highest Price $18.6M
Total Listings 450
Avg. Days On Market 122
Avg. Price/SQFT $489

Property Types (active listings)

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New
4081 Rockefeller Avenue, SARASOTA

$295,000

4081 Rockefeller Avenue, SARASOTA

DIXIE HEIGHTS 3 Beds 2 Baths 1,146 SqFt 0 DOM Residential MLS® # A4671461
New
4514 Cactus Avenue, SARASOTA

$549,000

↑ $494,100

4514 Cactus Avenue, SARASOTA

FLORA-VILLA 3 Beds 3 Baths 1,678 SqFt 1 DOM Residential MLS® # A4671329
1354 Tearose Place, SARASOTA

$810,000

1354 Tearose Place, SARASOTA

MANDARIN PARK 2 Beds 3 Baths 1,904 SqFt 233 DOM Residential MLS® # A4643593
New
3619 Pembrook Drive, SARASOTA

$595,000

3619 Pembrook Drive, SARASOTA

VILLAGE GREEN CLUB ESTATES UNIT B 3 Beds 2 Baths 1,625 SqFt 1 DOM Residential MLS® # TB8444082
New
Vamo Way, SARASOTA

$99,000

Vamo Way, SARASOTA

VAMO 3RD ADD TO 0 Beds 0 Baths 0 SqFt 0 DOM Land MLS® # A4671362
New
1856 Mova Street, SARASOTA

$349,500

1856 Mova Street, SARASOTA

GIBSON BESSIE P SUB 3 Beds 2 Baths 1,475 SqFt 1 DOM Residential MLS® # A4670765
New
2826 Marlette Street, SARASOTA

$625,000

2826 Marlette Street, SARASOTA

SARASOTA-VENICE CO SUB 3 Beds 3 Baths 1,476 SqFt 1 DOM Residential MLS® # A4671301
New
3512 Camino Real, SARASOTA

$2,950,000

3512 Camino Real, SARASOTA

GRANADA 5 Beds 5 Baths 3,810 SqFt 1 DOM Residential MLS® # A4671290
New
3705 Tangier Terrace, SARASOTA

$2,097,000

3705 Tangier Terrace, SARASOTA

SAN REMO ESTATES 3 Beds 3 Baths 2,529 SqFt 1 DOM Residential MLS® # A4671232
New
1635 Baywinds Lane, SARASOTA

$681,000

1635 Baywinds Lane, SARASOTA

BAYWINDS ESTATES 3 Beds 2 Baths 1,916 SqFt 2 DOM Residential MLS® # A4670164
1543 Eastbrook Drive, SARASOTA

$3,750,000

1543 Eastbrook Drive, SARASOTA

KENTWOOD ESTATES 4 Beds 6 Baths 4,788 SqFt 253 DOM Residential MLS® # A4641145
New
5619 New York Avenue, SARASOTA

$469,000

5619 New York Avenue, SARASOTA

SUN HAVEN 3 Beds 2 Baths 1,577 SqFt 1 DOM Residential MLS® # A4664577
New
3851 Tangier Terrace, SARASOTA

$2,088,000

3851 Tangier Terrace, SARASOTA

SAN REMO ESTATES 4 Beds 3 Baths 2,379 SqFt 6 DOM Residential MLS® # A4667394
New
2159 Hawthorne Street, SARASOTA

$1,500,000

2159 Hawthorne Street, SARASOTA

LA LINDA TERRACE 4 Beds 4 Baths 3,163 SqFt 2 DOM Residential MLS® # A4671095
New
1649 Stanford Lane, SARASOTA

$1,675,000

1649 Stanford Lane, SARASOTA

AQUALANE ESTATES 1ST 3 Beds 2 Baths 1,995 SqFt 2 DOM Residential MLS® # A4671051
New
1649 Stanford Lane, SARASOTA

$1,675,000

1649 Stanford Lane, SARASOTA

AQUALANE ESTATES 1ST 0 Beds 0 Baths 0 SqFt 1 DOM Land MLS® # A4671072
New
1406 Tangier Way, SARASOTA

$5,750,000

1406 Tangier Way, SARASOTA

SAN REMO ESTATES 4 Beds 3 Baths 3,294 SqFt 2 DOM Residential MLS® # A4667391
New
1705 Field Road, SARASOTA

$2,949,000

1705 Field Road, SARASOTA

OYSTER BAY ESTATES 4 Beds 5 Baths 2,400 SqFt 2 DOM Residential MLS® # A4671008
New
1739 Cherokee Drive, SARASOTA

$4,499,000

1739 Cherokee Drive, SARASOTA

CHEROKEE PARK 4 Beds 5 Baths 4,538 SqFt 2 DOM Residential MLS® # A4670822
2065 Goldenrod Street, SARASOTA

$2,700,000

2065 Goldenrod Street, SARASOTA

AKIN ACRES 6 Beds 8 Baths 3,677 SqFt 122 DOM Residential MLS® # A4656340
New
1610 S Lake Shore Drive, SARASOTA

$1,995,000

1610 S Lake Shore Drive, SARASOTA

OYSTER BAY ESTATES 3 Beds 3 Baths 2,821 SqFt 2 DOM Residential MLS® # A4670153

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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