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 $99.9K
Highest Price $18M
Total Listings 400
Avg. Days On Market 103
Avg. Price/SQFT $531

Property Types (active listings)

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New
2639 Cardwell Way, SARASOTA

$535,000

2639 Cardwell Way, SARASOTA

GULF GATE WOODS 2 Beds 2 Baths 1,300 SqFt 0 DOM Residential MLS® # A4609046
New
2574 Hawthorne Street, SARASOTA

$590,000

2574 Hawthorne Street, SARASOTA

TURNERS J C SUB 3 Beds 2 Baths 1,362 SqFt 0 DOM Residential MLS® # A4609184
New
5440 Eagles Point Circle 201, SARASOTA

$842,000

5440 Eagles Point Circle 201, SARASOTA

EAGLES POINT AT THE LANDINGS 3 3 Beds 3 Baths 1,936 SqFt 0 DOM Residential MLS® # A4608724
New
5335 Matthew Court, SARASOTA

$625,000

5335 Matthew Court, SARASOTA

FOREST OAKS 3 Beds 2 Baths 1,779 SqFt 0 DOM Residential MLS® # U8240984
New
1516 Pelican Cove Road Gr243, SARASOTA

$280,000

1516 Pelican Cove Road Gr243, SARASOTA

PELICAN COVE XVII 2 Beds 2 Baths 1,211 SqFt 1 DOM Residential MLS® # N6132730
New
1617 Baywinds Lane, SARASOTA

$1,234,500

1617 Baywinds Lane, SARASOTA

BAYWINDS ESTATES 4 Beds 4 Baths 2,469 SqFt 1 DOM Residential MLS® # A4609170
New
2224 Bahia Vista Street E7, SARASOTA

$279,500

2224 Bahia Vista Street E7, SARASOTA

CORDOVA GARDENS II 2 Beds 2 Baths 982 SqFt 1 DOM Residential MLS® # A4608345
New
7542 Swanson Lane, SARASOTA

$479,900

7542 Swanson Lane, SARASOTA

GULF GATE WOODS 2 Beds 2 Baths 1,176 SqFt 1 DOM Residential MLS® # A4609154
New
1703 Starling Drive 1703, SARASOTA

$725,000

1703 Starling Drive 1703, SARASOTA

VILLAS AT EAGLES POINT 3 Beds 3 Baths 2,172 SqFt 2 DOM Residential MLS® # A4608335
New
3224 Kenmore Drive, SARASOTA

$472,900

3224 Kenmore Drive, SARASOTA

GULF GATE 2 Beds 2 Baths 1,664 SqFt 2 DOM Residential MLS® # A4607534
New
4035 South School Avenue A1, SARASOTA

$212,000

4035 South School Avenue A1, SARASOTA

OAKWOOD GARDENS 2 Beds 1 Bath 783 SqFt 3 DOM Residential MLS® # A4608963
New
1958 Bougainvillea Street, SARASOTA

$750,000

1958 Bougainvillea Street, SARASOTA

POINSETTIA PARK 2 2 Beds 1 Bath 952 SqFt 3 DOM Residential MLS® # A4608970
New
1690 Arlington Street, SARASOTA

$2,495,000

1690 Arlington Street, SARASOTA

MCINTYRE WILSON & POTTERS 4 Beds 5 Baths 2,965 SqFt 4 DOM Residential MLS® # A4606798
New
3164 Espanola Drive, SARASOTA

$825,000

3164 Espanola Drive, SARASOTA

FRST LAKES COUNTRY CLUB ESTATES 3 Beds 3 Baths 2,420 SqFt 4 DOM Residential MLS® # A4608727
New
1958 Bougainvillea Street, SARASOTA

$750,000

1958 Bougainvillea Street, SARASOTA

POINSETTIA PARK 2 0 Beds 0 Baths 0 SqFt 6 DOM Land MLS® # A4608749
New
3006 Hawthorne Street, SARASOTA

$349,000

3006 Hawthorne Street, SARASOTA

COTTAGE IN THE PINES 3 Beds 3 Baths 1,835 SqFt 6 DOM Residential MLS® # A4606197
New
1511 Pelican Point Drive 280, SARASOTA

$628,000

1511 Pelican Point Drive 280, SARASOTA

PELICAN COVE VII 2 Beds 2 Baths 1,368 SqFt 6 DOM Residential MLS® # A4608419
New
2352 Palm Terrace, SARASOTA

$875,000

2352 Palm Terrace, SARASOTA

RIDGEWOOD 5 Beds 2 Baths 2,317 SqFt 5 DOM Residential MLS® # A4605284
New
1905 Jasmine Drive, SARASOTA

$799,000

↓ $30,000

1905 Jasmine Drive, SARASOTA

HARTLAND PARK 3 Beds 2 Baths 1,658 SqFt 6 DOM Residential MLS® # A4608084
New
3714 Flores Avenue, SARASOTA

$3,195,000

3714 Flores Avenue, SARASOTA

GRANADA 4 Beds 5 Baths 4,046 SqFt 7 DOM Residential MLS® # O6198998
New
1636 Stickney Point Road 36-201, SARASOTA

$464,900

1636 Stickney Point Road 36-201, SARASOTA

CASTEL DEL MARE 2 Beds 2 Baths 1,016 SqFt 7 DOM Residential MLS® # N6132592

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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