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 $1.7M
Lowest Price $1K
Highest Price $28.5M
Total Listings 435
Avg. Days On Market 93
Avg. Price/SQFT $574

Property Types (active listings)

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$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
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1805 Goldenrod Street, SARASOTA

$3,750,000

1805 Goldenrod Street, SARASOTA

POINSETTIA PARK 2 5 Beds 5 Baths 3,595 SqFt 30 DOM Residential MLS® # A4593630
New
2521 Jamaica Street, SARASOTA

$510,000

2521 Jamaica Street, SARASOTA

PHILLIPPI COVE ADD 3 Beds 2 Baths 1,570 SqFt 3 DOM Residential MLS® # A4600838
New
3860 Camino Real, SARASOTA

$2,200,000

3860 Camino Real, SARASOTA

GRANADA 4 Beds 6 Baths 3,381 SqFt 3 DOM Residential MLS® # A4600678
New
2050 Euclid Terrace, SARASOTA

$2,211,000

2050 Euclid Terrace, SARASOTA

EUCLID SUB 4 Beds 5 Baths 2,760 SqFt 3 DOM Residential MLS® # A4600957
New
2335 Prospect Street, SARASOTA

$1,575,000

2335 Prospect Street, SARASOTA

LOMA LINDA PARK 3 Beds 3 Baths 1,825 SqFt 3 DOM Residential MLS® # A4600948
New
5039 Kestral Park Drive 67, SARASOTA

$529,000

5039 Kestral Park Drive 67, SARASOTA

LANDINGS CARRIAGEHOUSE I 2 Beds 2 Baths 1,368 SqFt 3 DOM Residential MLS® # A4600615
New
1607 Bay Road, SARASOTA

$2,899,000

1607 Bay Road, SARASOTA

GRANADA SUB 4 Beds 5 Baths 3,533 SqFt 3 DOM Residential MLS® # A4600625
New
1964 Datura Street, SARASOTA

$2,400,000

1964 Datura Street, SARASOTA

DESOTA PARK 4 Beds 4 Baths 3,272 SqFt 3 DOM Residential MLS® # A4600886
New
2430 Floyd Street, SARASOTA

$2,200,000

2430 Floyd Street, SARASOTA

RUSTIC LODGE 5 Beds 4 Baths 2,743 SqFt 3 DOM Residential MLS® # A4600930
New
2240 Stickney Point Road 219, SARASOTA

$259,900

2240 Stickney Point Road 219, SARASOTA

TREGATE MANOR 2 Beds 2 Baths 951 SqFt 3 DOM Residential MLS® # A4600570
New
4567 Camino Real, SARASOTA

$1,845,000

4567 Camino Real, SARASOTA

THE LANDINGS 3 Beds 3 Baths 3,400 SqFt 3 DOM Residential MLS® # A4600819
New
2375 Temple Street, SARASOTA

$750,000

2375 Temple Street, SARASOTA

LOMA LINDA PARK 4 Beds 3 Baths 2,970 SqFt 3 DOM Residential MLS® # A4600812
New
3402 Brookline Drive, SARASOTA

$829,900

3402 Brookline Drive, SARASOTA

FRST LAKES COUNTRY CLUB ESTATES 3 Beds 2 Baths 1,710 SqFt 4 DOM Residential MLS® # U8231986
New
1720 Glenhouse Drive Gl428, SARASOTA

$387,500

1720 Glenhouse Drive Gl428, SARASOTA

PELICAN COVE XIV 2 Beds 2 Baths 1,112 SqFt 4 DOM Residential MLS® # A4599896
New
2415 Prospect Street, SARASOTA

$475,000

2415 Prospect Street, SARASOTA

RUSTIC LODGE 2 2 Beds 1 Bath 1,088 SqFt 4 DOM Residential MLS® # A4600297
New
2534 River Ridge Drive, SARASOTA

$728,000

2534 River Ridge Drive, SARASOTA

SOUTH GATE 3 Beds 2 Baths 2,070 SqFt 4 DOM Residential MLS® # FC298158
New
3391 Gulf Watch Court, SARASOTA

$499,000

3391 Gulf Watch Court, SARASOTA

GULF GATE GLEN 3 Beds 2 Baths 1,423 SqFt 4 DOM Residential MLS® # A4600345
New
2308 S Tuttle Ave, SARASOTA

$545,000

2308 S Tuttle Ave, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,714 SqFt 5 DOM Residential MLS® # A4600223
New
2233 Hillview Street, SARASOTA

$3,250,000

2233 Hillview Street, SARASOTA

LA LINDA TERRACE 4 Beds 5 Baths 3,758 SqFt 5 DOM Residential MLS® # A4600212
New
5027 Kestral Park Drive 64, SARASOTA

$719,000

5027 Kestral Park Drive 64, SARASOTA

LANDINGS CARRIAGEHOUSE I 2 Beds 2 Baths 1,440 SqFt 5 DOM Residential MLS® # A4599810
New
2369 Bahia Vista St, SARASOTA

$1,175,000

2369 Bahia Vista St, SARASOTA

AVON HEIGHTS 2 4 Beds 3 Baths 2,048 SqFt 5 DOM Residential MLS® # T3505964

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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