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 $1.6M
Lowest Price $99.9K
Highest Price $18M
Total Listings 405
Avg. Days On Market 100
Avg. Price/SQFT $536

Property Types (active listings)

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New
1958 Bougainvillea Street, SARASOTA

$750,000

1958 Bougainvillea Street, SARASOTA

POINSETTIA PARK 2 0 Beds 0 Baths 0 SqFt 0 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 1 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 1 DOM Residential MLS® # A4608419
New
2352 Palm Terrace, SARASOTA

$875,000

2352 Palm Terrace, SARASOTA

RIDGEWOOD 5 Beds 2 Baths 2,317 SqFt 1 DOM Residential MLS® # A4605284
New
N/A, SARASOTA

$829,000

N/A, SARASOTA

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

$3,195,000

3714 Flores Avenue, SARASOTA

GRANADA 4 Beds 5 Baths 4,046 SqFt 2 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 2 DOM Residential MLS® # N6132592
New
3069 Gulf Gate Drive, SARASOTA

$479,000

3069 Gulf Gate Drive, SARASOTA

GULF GATE 3 Beds 2 Baths 1,817 SqFt 2 DOM Residential MLS® # A4608386
New
3530 Mineola Drive, SARASOTA

$1,600,000

3530 Mineola Drive, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,693 SqFt 2 DOM Residential MLS® # A4608542
New
3336 Old Oak Drive, SARASOTA

$18,000,000

3336 Old Oak Drive, SARASOTA

SHORELAND WOODS SUB 3 Beds 5 Baths 5,932 SqFt 2 DOM Residential MLS® # A4608565
New
6313 Hollywood Boulevard, SARASOTA

$995,000

6313 Hollywood Boulevard, SARASOTA

EMERALD HARBOR 3 Beds 2 Baths 1,537 SqFt 1 DOM Residential MLS® # A4608357
New
1627 Baywinds Lane, SARASOTA

$750,000

1627 Baywinds Lane, SARASOTA

BAYWINDS ESTATES 2 Beds 2 Baths 1,899 SqFt 2 DOM Residential MLS® # A4608355
New
2147 Arlington Street, SARASOTA

$1,790,000

2147 Arlington Street, SARASOTA

0 Beds 0 Baths 0 SqFt 1 DOM Land MLS® # A4608402
New
2364 Floyd Street, SARASOTA

$1,200,000

2364 Floyd Street, SARASOTA

LOMA LINDA PARK 4 Beds 3 Baths 2,248 SqFt 3 DOM Residential MLS® # A4608332
New
3234 Restful Lane, SARASOTA

$675,000

3234 Restful Lane, SARASOTA

RESTFUL PINES 4 Beds 3 Baths 1,915 SqFt 3 DOM Residential MLS® # A4608445
New
1320 Rhodes Avenue, SARASOTA

$390,000

1320 Rhodes Avenue, SARASOTA

WILDWOOD GARDENS 2 Beds 2 Baths 955 SqFt 3 DOM Residential MLS® # A4607680
New
4228 Midland Road, SARASOTA

$449,000

4228 Midland Road, SARASOTA

FLORAL PARK HOMESTEADS 4 Beds 3 Baths 2,933 SqFt 3 DOM Residential MLS® # O6198995
New
5600 South Lockwood Ridge Road, SARASOTA

$400,000

5600 South Lockwood Ridge Road, SARASOTA

SUN HAVEN 2 Beds 2 Baths 1,659 SqFt 3 DOM Residential MLS® # A4603272
New
5228 Landings Boulevard 202, SARASOTA

$450,000

5228 Landings Boulevard 202, SARASOTA

LANDINGS SOUTH I 2 Beds 3 Baths 1,778 SqFt 4 DOM Residential MLS® # A4608155
New
5697 Ashton Lake Drive 6, SARASOTA

$299,000

5697 Ashton Lake Drive 6, SARASOTA

ASHTON LAKES 01 & 02 2 Beds 2 Baths 848 SqFt 4 DOM Residential MLS® # A4607971
New
2555 Hillview Street, SARASOTA

$1,200,000

2555 Hillview Street, SARASOTA

TURNERS J C SUB 0 Beds 0 Baths 0 SqFt 4 DOM Land MLS® # A4608071

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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