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 $120K
Highest Price $26.4M
Total Listings 420
Avg. Days On Market 131
Avg. Price/SQFT $500

Property Types (active listings)

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New
2220 Bahia Vista Street G5, SARASOTA

$184,900

2220 Bahia Vista Street G5, SARASOTA

CORDOVA GARDENS III 2 Beds 2 Baths 1,024 SqFt 1 DOM Residential MLS® # A4700239
New
1300 Loma Linda Court, SARASOTA

$799,000

1300 Loma Linda Court, SARASOTA

LOMA LINDA PARK 3 Beds 2 Baths 1,191 SqFt 1 DOM Residential MLS® # A4700072
New
1300 Loma Linda Court, SARASOTA

$799,000

1300 Loma Linda Court, SARASOTA

LOMA LINDA PARK 0 Beds 0 Baths 0 SqFt 0 DOM Land MLS® # A4700068
Open House
2949 Bougainvillea Street, SARASOTA

$429,900

2949 Bougainvillea Street, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,574 SqFt 42 DOM Residential
Sat, Jul 18th, 2026 @ 10am - 12pm
MLS® # A4687629
New Open House
3013 Clark Road 6, SARASOTA

$329,000

3013 Clark Road 6, SARASOTA

LOS LAGOS 2 Beds 2 Baths 1,283 SqFt 1 DOM Residential
Sat, Jul 18th, 2026 @ 12pm - 2pm
MLS® # C7528185
New
3807 Jaffa Drive, SARASOTA

$499,000

3807 Jaffa Drive, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,656 SqFt 1 DOM Residential MLS® # A4698939
New Open House
3136 Bispham Road, SARASOTA

$619,000

3136 Bispham Road, SARASOTA

GULF GATE 3 Beds 2 Baths 1,994 SqFt 1 DOM Residential
Sun, Jul 19th, 2026 @ 1am - 3pm
MLS® # A4699957
New
2114 Floyd Street, SARASOTA

$2,150,000

2114 Floyd Street, SARASOTA

LOMA LINDA PARK RESUB 4 Beds 4 Baths 3,105 SqFt 1 DOM Residential MLS® # A4699956
New
5938 Murdock Avenue, SARASOTA

$297,700

5938 Murdock Avenue, SARASOTA

GOLDEN ACRES 1ST ADD 2 Beds 2 Baths 1,381 SqFt 1 DOM Residential MLS® # A4697066
New
1827 Baywood Drive, SARASOTA

$1,925,000

1827 Baywood Drive, SARASOTA

BAY VIEW ACRES 3 Beds 2 Baths 2,565 SqFt 1 DOM Residential MLS® # A4697757
New
2742 S East Avenue, SARASOTA

$500,000

2742 S East Avenue, SARASOTA

SOUTH SIDE PARK 2 Beds 2 Baths 1,342 SqFt 2 DOM Residential MLS® # A4692545
New
3727 Tangier Terrace, SARASOTA

$2,490,000

3727 Tangier Terrace, SARASOTA

SAN REMO ESTATES 4 Beds 3 Baths 2,696 SqFt 3 DOM Residential MLS® # A4699858
New Open House
1838 Oleander Street, SARASOTA

$3,295,000

1838 Oleander Street, SARASOTA

POINSETTIA PARK 2 4 Beds 3 Baths 3,230 SqFt 3 DOM Residential
Fri, Jul 17th, 2026 @ 12pm - 3pm
MLS® # A4697493
3084 Spirea Street, SARASOTA

$599,900

3084 Spirea Street, SARASOTA

FLORA-VILLA 5 Beds 3 Baths 2,284 SqFt 57 DOM Residential MLS® # TB8506821
New
2348 Doud Street, SARASOTA

$365,000

2348 Doud Street, SARASOTA

PINEHURST PARK REP OF 3 Beds 1 Bath 1,118 SqFt 4 DOM Residential MLS® # A4696579
New
1707 Caribbean Drive, SARASOTA

$2,997,000

1707 Caribbean Drive, SARASOTA

CORAL COVE 4 Beds 4 Baths 5,012 SqFt 5 DOM Residential MLS® # A4698598
New Open House
2011 Outer Drive, SARASOTA

$499,000

2011 Outer Drive, SARASOTA

LAS LOMAS DE SARASOTA 3 Beds 3 Baths 1,490 SqFt 5 DOM Residential
Sat, Jul 18th, 2026 @ 11am - 1pm
MLS® # TB8525989
New
2930 Hawthorne Street, SARASOTA

$250,000

2930 Hawthorne Street, SARASOTA

RIO VISTA 0 Beds 0 Baths 0 SqFt 7 DOM Land MLS® # A4699290
1715 Pelican Cove Road Gl339, SARASOTA

$219,800

1715 Pelican Cove Road Gl339, SARASOTA

PELICAN COVE XIV 1 Bed 1 Bath 731 SqFt 8 DOM Residential MLS® # A4697127
1520 Pelican Point Drive Ba251, SARASOTA

$329,000

1520 Pelican Point Drive Ba251, SARASOTA

PELICAN COVE IV 1 Bed 1 Bath 937 SqFt 327 DOM Residential MLS® # A4662594
Open House
2420 Floyd Street, SARASOTA

$2,190,000

2420 Floyd Street, SARASOTA

RUSTIC LODGE 5 Beds 5 Baths 3,356 SqFt 8 DOM Residential
Fri, Jul 17th, 2026 @ 1pm - 4pm
MLS® # A4699366

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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