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 $140K
Highest Price $18.6M
Total Listings 515
Avg. Days On Market 123
Avg. Price/SQFT $496

Property Types (active listings)

Search West Of The Trail Real Estate Listings

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New
4111 West Iola Drive, SARASOTA

$460,000

4111 West Iola Drive, SARASOTA

DIXIE HEIGHTS 3 Beds 2 Baths 1,372 SqFt 0 DOM Residential MLS® # A4658175
New
Swift Road, SARASOTA

$500,000

Swift Road, SARASOTA

0 Beds 0 Baths 0 SqFt 0 DOM Land MLS® # A4658042
New
2708 Wilkinson Road, SARASOTA

$414,900

2708 Wilkinson Road, SARASOTA

BELLFLOWER GARDENS 2 Beds 2 Baths 1,464 SqFt 0 DOM Residential MLS® # A4657623
New
2105 Hibiscus Street, SARASOTA

$698,000

2105 Hibiscus Street, SARASOTA

GROVE LAWN REP 2 Beds 2 Baths 1,420 SqFt 0 DOM Residential MLS® # A4658077
New
1876 Livingstone Street, SARASOTA

$799,000

1876 Livingstone Street, SARASOTA

NORTH VAMO SUB 1 5 Beds 4 Baths 2,926 SqFt 1 DOM Residential MLS® # A4657581
New
2837 Yorktown Street, SARASOTA

$435,000

2837 Yorktown Street, SARASOTA

COLONIAL TERRACE 4 Beds 3 Baths 1,437 SqFt 3 DOM Residential MLS® # A4657913
New
Trinidad Street, SARASOTA

$150,000

Trinidad Street, SARASOTA

VIRGINIA HEIGHTS SUB 0 Beds 0 Baths 0 SqFt 4 DOM Land MLS® # A4657700
New
2772 Woodgate Lane 26, SARASOTA

$220,000

2772 Woodgate Lane 26, SARASOTA

PINEWOOD VILLAGE I 2 Beds 2 Baths 874 SqFt 4 DOM Residential MLS® # TB8403952
New
1884 Grove Street, SARASOTA

$1,595,000

1884 Grove Street, SARASOTA

GROVE HEIGHTS 3 Beds 3 Baths 2,714 SqFt 4 DOM Residential MLS® # A4657617
New
3136 Webber Street, SARASOTA

$600,000

3136 Webber Street, SARASOTA

ANONYMOUS ACRE 3 Beds 2 Baths 1,698 SqFt 4 DOM Residential MLS® # A4657914
New
8985 Pohoy Avenue, SARASOTA

$469,000

8985 Pohoy Avenue, SARASOTA

PETRECCA TERRACE 3 Beds 2 Baths 1,684 SqFt 4 DOM Residential MLS® # A4657183
New
5524 Antilles Drive, SARASOTA

$615,000

5524 Antilles Drive, SARASOTA

PHILLIPPI GARDENS 07 3 Beds 2 Baths 1,519 SqFt 4 DOM Residential MLS® # A4656785
New
2763 Woodgate Lane 105, SARASOTA

$195,000

2763 Woodgate Lane 105, SARASOTA

PINEWOOD VILLAGE II 2 Beds 2 Baths 974 SqFt 4 DOM Residential MLS® # A4657776
New
2460 Hillview Street, SARASOTA

$995,000

2460 Hillview Street, SARASOTA

SINGLETARYS SUB 3 Beds 2 Baths 2,120 SqFt 5 DOM Residential MLS® # A4657687
New
1530 Pine Bay Drive, SARASOTA

$2,700,000

1530 Pine Bay Drive, SARASOTA

JOHNSON ESTATES 4 Beds 5 Baths 3,805 SqFt 6 DOM Residential MLS® # A4657245
New
3621 South Lockwood Ridge Road, SARASOTA

$464,900

3621 South Lockwood Ridge Road, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,804 SqFt 6 DOM Residential MLS® # A4654914
New
2410 Prospect Street, SARASOTA

$979,000

2410 Prospect Street, SARASOTA

RUSTIC LODGE 2 3 Beds 3 Baths 1,969 SqFt 7 DOM Residential MLS® # A4656811
New
3261 Mayflower Street, SARASOTA

$335,000

3261 Mayflower Street, SARASOTA

SHADOW LAKES 2 Beds 2 Baths 1,159 SqFt 7 DOM Residential MLS® # TB8402212
New
1864 Goldenrod Street, SARASOTA

$2,185,000

1864 Goldenrod Street, SARASOTA

POINSETTIA PARK 2 4 Beds 3 Baths 2,307 SqFt 7 DOM Residential MLS® # A4654776
New
1753 Dawn Street 305, SARASOTA

$387,500

1753 Dawn Street 305, SARASOTA

KEY POINT VILLAGE 2 Beds 2 Baths 1,042 SqFt 7 DOM Residential MLS® # A4656477
2504 Tanglewood Drive, SARASOTA

$869,000

2504 Tanglewood Drive, SARASOTA

SOUTH GATE 4 Beds 3 Baths 2,782 SqFt 10 DOM Residential MLS® # A4656554

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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