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 $1.2M
Lowest Price $118K
Highest Price $18.6M
Total Listings 422
Avg. Days On Market 121
Avg. Price/SQFT $484

Property Types (active listings)

Search West Of The Trail Real Estate Listings

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New
6051 Carlton Avenue, SARASOTA

$375,000

6051 Carlton Avenue, SARASOTA

DENHAM ACRES 4 Beds 2 Baths 972 SqFt 1 DOM Residential MLS® # A4668295
New
1620 N Lodge Drive, SARASOTA

$4,900,000

1620 N Lodge Drive, SARASOTA

CHEROKEE LODGE 5 Beds 4 Baths 4,660 SqFt 1 DOM Residential MLS® # A4667729
New
5400 Eagles Point Circle 405, SARASOTA

$599,000

5400 Eagles Point Circle 405, SARASOTA

BAYVIEW HOMES, THE LANDINGS, EAGLES POINT 2 Beds 2 Baths 1,695 SqFt 1 DOM Residential MLS® # A4668182
New
5617 Olive Avenue, SARASOTA

$255,000

5617 Olive Avenue, SARASOTA

SUN HAVEN 2 Beds 1 Bath 1,166 SqFt 1 DOM Residential MLS® # A4668154
New
2130 Olentary Street, SARASOTA

$339,000

2130 Olentary Street, SARASOTA

SARASOTA-VENICE CO RIVER SUB 3 Beds 1 Bath 1,018 SqFt 3 DOM Residential MLS® # A4668158
New
1815 Grove Street, SARASOTA

$2,250,000

1815 Grove Street, SARASOTA

GROVE HEIGHTS 4 Beds 5 Baths 2,617 SqFt 4 DOM Residential MLS® # A4668085
New
2949 Bougainvillea Street, SARASOTA

$549,800

2949 Bougainvillea Street, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,574 SqFt 1 DOM Residential MLS® # A4667837
New
1633 Ridgewood Lane, SARASOTA

$1,549,000

1633 Ridgewood Lane, SARASOTA

AQUALANE ESTATES 3RD 3 Beds 2 Baths 1,839 SqFt 3 DOM Residential MLS® # A4668036
New
1331 S Allendale Avenue, SARASOTA

$385,000

1331 S Allendale Avenue, SARASOTA

NACIREMA 2 Beds 1 Bath 1,048 SqFt 3 DOM Residential MLS® # A4668118
New
1887 Buccaneer Circle, SARASOTA

$1,869,900

1887 Buccaneer Circle, SARASOTA

BUCCANEER BAY 3 Beds 4 Baths 3,336 SqFt 1 DOM Residential MLS® # A4668095
New
1603 Starling Drive 101, SARASOTA

$325,000

1603 Starling Drive 101, SARASOTA

LANDINGS SOUTH V 2 Beds 2 Baths 1,712 SqFt 3 DOM Residential MLS® # A4667942
New
3030 Ashton Road, SARASOTA

$749,000

3030 Ashton Road, SARASOTA

SARASOTA VENICE CO 09 37 18 3 Beds 3 Baths 2,250 SqFt 4 DOM Residential MLS® # C7516086
New
1631 Worrington Street, SARASOTA

$819,900

1631 Worrington Street, SARASOTA

JOHNSON ESTATES 3 Beds 3 Baths 1,469 SqFt 4 DOM Residential MLS® # A4666922
New
2216 Bahia Vista Street H1, SARASOTA

$175,000

2216 Bahia Vista Street H1, SARASOTA

CORDOVA GARDENS III 2 Beds 2 Baths 982 SqFt 1 DOM Residential MLS® # A4667844
New
1720 Glenhouse Drive 330, SARASOTA

$240,000

1720 Glenhouse Drive 330, SARASOTA

PELICAN COVE XIV 1 Bed 1 Bath 731 SqFt 4 DOM Residential MLS® # A4667363
New
2516 Tanglewood Drive, SARASOTA

$895,000

2516 Tanglewood Drive, SARASOTA

SOUTH GATE UNIT 31 4 Beds 3 Baths 2,767 SqFt 3 DOM Residential MLS® # A4665653
New
2833 Valley Forge Street, SARASOTA

$589,000

2833 Valley Forge Street, SARASOTA

COLONIAL TERRACE 3 Beds 3 Baths 2,046 SqFt 1 DOM Residential MLS® # A4667164
New
1526 Pelican Point Drive 146, SARASOTA

$340,000

1526 Pelican Point Drive 146, SARASOTA

PELICAN COVE I 1 Bed 1 Bath 937 SqFt 1 DOM Residential MLS® # A4667409
New
1884 Southpointe Drive, SARASOTA

$1,099,000

1884 Southpointe Drive, SARASOTA

SOUTHPOINTE SHORES 6 Beds 5 Baths 2,808 SqFt 2 DOM Residential MLS® # A4667255
New
1617 Bayhouse Court 121, SARASOTA

$575,000

1617 Bayhouse Court 121, SARASOTA

PELICAN COVE 3 Beds 3 Baths 1,635 SqFt 1 DOM Residential MLS® # A4667758
4761 Pine Harrier Drive, SARASOTA

$1,450,000

4761 Pine Harrier Drive, SARASOTA

THE LANDINGS 3 Beds 3 Baths 2,921 SqFt 92 DOM Residential MLS® # A4656772

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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