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 $125K
Highest Price $16M
Total Listings 419
Avg. Days On Market 90
Avg. Price/SQFT $537

Property Types (active listings)

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New
4205 Augustine Avenue, SARASOTA

$499,999

4205 Augustine Avenue, SARASOTA

FLORAL PARK HOMESTEADS 3 Beds 2 Baths 1,063 SqFt 1 DOM Residential MLS® # R4907676
New
5795 Summer Side Lane 6b, SARASOTA

$270,000

5795 Summer Side Lane 6b, SARASOTA

SUMMERSIDE 2 Beds 2 Baths 1,125 SqFt 0 DOM Residential MLS® # A4603977
New
2395 Hillview Street, SARASOTA

$1,295,000

2395 Hillview Street, SARASOTA

JOINERS A L SUB 3 Beds 3 Baths 2,738 SqFt 0 DOM Residential MLS® # A4603891
New
2911 Edgewood Lane, SARASOTA

$379,900

2911 Edgewood Lane, SARASOTA

HYDE PARK TERRACE 3 Beds 2 Baths 1,352 SqFt 2 DOM Residential MLS® # D6135578
New
5908 Murdock Avenue, SARASOTA

$547,921

5908 Murdock Avenue, SARASOTA

GOLDEN ACRES 1ST ADD 3 Beds 2 Baths 1,899 SqFt 2 DOM Residential MLS® # A4603758
New
2260 Willow Tree Drive 86, SARASOTA

$289,000

2260 Willow Tree Drive 86, SARASOTA

WOODSIDE SOUTH PH 1 2 & 3 2 Beds 2 Baths 1,120 SqFt 2 DOM Residential MLS® # A4603790
New
2624 Hibiscus Street, SARASOTA

$749,000

2624 Hibiscus Street, SARASOTA

1302 - SOUTH GATE UNIT 13 4 Beds 3 Baths 1,680 SqFt 3 DOM Residential MLS® # A4603737
New
5426 Creeping Hammock Drive, SARASOTA

$395,000

5426 Creeping Hammock Drive, SARASOTA

WESTLAKE ESTATES 3 Beds 2 Baths 2,213 SqFt 3 DOM Residential MLS® # A4603640
New
2517 South Brink Avenue, SARASOTA

$749,000

2517 South Brink Avenue, SARASOTA

SOUTH GATE 3 Beds 3 Baths 1,733 SqFt 3 DOM Residential MLS® # A4603636
New
4023 Murdock Avenue, SARASOTA

$339,900

4023 Murdock Avenue, SARASOTA

FLORA VILLA FINAL SURV 3 Beds 1 Bath 1,081 SqFt 3 DOM Residential MLS® # T3512218
New
1608 Bayhouse Point Drive 401, SARASOTA

$425,000

↑ $15,000

1608 Bayhouse Point Drive 401, SARASOTA

PELICAN COVE XIV 2 Beds 2 Baths 1,288 SqFt 4 DOM Residential MLS® # A4603644
New
1608 Stickney Point Road 101, SARASOTA

$564,500

1608 Stickney Point Road 101, SARASOTA

CASTEL DEL MARE 2 Beds 2 Baths 1,016 SqFt 4 DOM Residential MLS® # A4603169
New
1887 Rita Street, SARASOTA

$539,000

1887 Rita Street, SARASOTA

MEAD HELEN D 3 Beds 2 Baths 2,241 SqFt 4 DOM Residential MLS® # A4603639
New
3013 Clark Road 2, SARASOTA

$250,000

3013 Clark Road 2, SARASOTA

LOS LAGOS 2 Beds 2 Baths 1,320 SqFt 4 DOM Residential MLS® # A4603514
New
4154 Iola Drive, SARASOTA

$425,000

4154 Iola Drive, SARASOTA

GOLF ESTATES 2 Beds 2 Baths 1,302 SqFt 4 DOM Residential MLS® # A4603492
New
1225 Holly Fern Lane, SARASOTA

$1,500,000

1225 Holly Fern Lane, SARASOTA

MANDARIN PARK 3 Beds 3 Baths 1,909 SqFt 4 DOM Residential MLS® # A4603340
New
5531 Cannes Cir 201, SARASOTA

$1,399,000

5531 Cannes Cir 201, SARASOTA

PHILLIPPI LANDINGS 3 Beds 2 Baths 2,024 SqFt 4 DOM Residential MLS® # O6186349
New
2428 Whippoorwill Circle, SARASOTA

$799,000

2428 Whippoorwill Circle, SARASOTA

WESLO WILLOWS 3 Beds 2 Baths 1,921 SqFt 5 DOM Residential MLS® # A4603008
New
7224 Antigua Place, SARASOTA

$640,000

7224 Antigua Place, SARASOTA

GULF GATE WOODS 3 Beds 2 Baths 1,477 SqFt 5 DOM Residential MLS® # A4603007
New
2810 Concord Street, SARASOTA

$519,900

2810 Concord Street, SARASOTA

COLONIAL TERRACE 3 Beds 2 Baths 1,861 SqFt 5 DOM Residential MLS® # A4603457
New
2527 Sunnyside Street, SARASOTA

$419,000

2527 Sunnyside Street, SARASOTA

SOUTH GATE 2 Beds 2 Baths 1,134 SqFt 5 DOM Residential MLS® # A4602991

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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