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 $95K
Highest Price $27.7M
Total Listings 505
Avg. Days On Market 104
Avg. Price/SQFT $535

Property Types (active listings)

Search West Of The Trail Real Estate Listings

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New
2613 Temple Street, SARASOTA

$1,680,000

2613 Temple Street, SARASOTA

HIGHLAND PARK 2 3 Beds 4 Baths 3,308 SqFt 0 DOM Residential MLS® # A4640522
New
1710 Starling Drive 102, SARASOTA

$455,000

1710 Starling Drive 102, SARASOTA

LANDINGS SOUTH VII 2 Beds 2 Baths 1,712 SqFt 0 DOM Residential MLS® # C7504622
New
3278 Village Green Drive 1024, SARASOTA

$279,900

3278 Village Green Drive 1024, SARASOTA

SOUTH GATE VILLAGE GREEN 10 2 Beds 2 Baths 1,323 SqFt 0 DOM Residential MLS® # A4639953
New
1621 Memory Lane, SARASOTA

$2,249,000

1621 Memory Lane, SARASOTA

NA 0 Beds 0 Baths 0 SqFt 0 DOM Land MLS® # A4640621
New
1621 Memory Lane, SARASOTA

$2,249,900

1621 Memory Lane, SARASOTA

NA 3 Beds 3 Baths 2,330 SqFt 0 DOM Residential MLS® # A4640500
New
1808 Flower Drive, SARASOTA

$10,500,000

1808 Flower Drive, SARASOTA

HARBOR ACRES SEC 2 4 Beds 6 Baths 5,609 SqFt 0 DOM Residential MLS® # A4640544
New
2424 Webber Street, SARASOTA

$315,000

2424 Webber Street, SARASOTA

ORANGE PARK 1 Bed 1 Bath 772 SqFt 1 DOM Residential MLS® # TB8345824
New
4062 South Shade Avenue, SARASOTA

$539,000

4062 South Shade Avenue, SARASOTA

PINE RIDGE 4 Beds 3 Baths 2,181 SqFt 1 DOM Residential MLS® # A4640598
New
1359 Tearose Place, SARASOTA

$1,100,000

1359 Tearose Place, SARASOTA

MANDARIN PARK 2 Beds 2 Baths 1,543 SqFt 1 DOM Residential MLS® # A4639082
New
1402 Tangier Way, SARASOTA

$6,998,000

↑ $98,000

1402 Tangier Way, SARASOTA

SAN REMO ESTATES 4 Beds 3 Baths 3,069 SqFt 1 DOM Residential MLS® # A4640444
New
2630 Moss Oak Drive 50, SARASOTA

$479,000

2630 Moss Oak Drive 50, SARASOTA

WOODBRIDGE ESTATES 2 Beds 3 Baths 1,985 SqFt 1 DOM Residential MLS® # A4640442
New
3705 Tangier Terrace, SARASOTA

$1,300,000

3705 Tangier Terrace, SARASOTA

SAN REMO ESTATES 3 Beds 3 Baths 2,529 SqFt 1 DOM Residential MLS® # A4639271
New
7272 Cass Circle, SARASOTA

$374,900

7272 Cass Circle, SARASOTA

SIESTA HEIGHTS 3 Beds 2 Baths 1,353 SqFt 2 DOM Residential MLS® # A4640022
New
1735 Flower Drive, SARASOTA

$2,395,000

1735 Flower Drive, SARASOTA

HARBOR ACRES SEC 2 3 Beds 4 Baths 2,840 SqFt 2 DOM Residential MLS® # A4639512
New
1846 Sandalwood Drive, SARASOTA

$800,000

1846 Sandalwood Drive, SARASOTA

SOUTHPOINTE SHORES 3 Beds 2 Baths 1,954 SqFt 2 DOM Residential MLS® # A4639415
New
3530 Flores Avenue, SARASOTA

$979,000

3530 Flores Avenue, SARASOTA

GRANADA 3 Beds 3 Baths 1,960 SqFt 2 DOM Residential MLS® # A4639588
New
2377 Burton Lane, SARASOTA

$890,000

2377 Burton Lane, SARASOTA

BURTON LANE 3 Beds 2 Baths 1,894 SqFt 2 DOM Residential MLS® # A4639987
New
5672 Bronx Avenue, SARASOTA

$275,000

5672 Bronx Avenue, SARASOTA

SUN HAVEN 2 Beds 2 Baths 1,328 SqFt 2 DOM Residential MLS® # A4640176
New
1687 Arlington Street, SARASOTA

$1,070,000

1687 Arlington Street, SARASOTA

LEWIS COMBS SUB 4 Beds 3 Baths 1,290 SqFt 2 DOM Residential MLS® # A4639514
New
2047 Roselawn Street, SARASOTA

$1,099,000

2047 Roselawn Street, SARASOTA

ROSELAWN 6 Beds 4 Baths 2,450 SqFt 3 DOM Residential MLS® # A4639611
New
1612 Pine Harrier Circle, SARASOTA

$1,500,000

1612 Pine Harrier Circle, SARASOTA

THE LANDINGS 4 Beds 3 Baths 2,742 SqFt 3 DOM Residential MLS® # A4639873

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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