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 $130K
Highest Price $18M
Total Listings 393
Avg. Days On Market 111
Avg. Price/SQFT $546

Property Types (active listings)

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New
1805 Goldenrod Street, SARASOTA

$3,650,000

1805 Goldenrod Street, SARASOTA

POINSETTIA PARK 2 5 Beds 5 Baths 3,595 SqFt 0 DOM Residential MLS® # A4618184
New
4847 Kestral Park Way N 23, SARASOTA

$699,000

4847 Kestral Park Way N 23, SARASOTA

LANDINGS CARRIAGEHOUSE II 3 Beds 2 Baths 1,970 SqFt 0 DOM Residential MLS® # A4618124
New
2327 Benson Street, SARASOTA

$325,000

2327 Benson Street, SARASOTA

PINEHURST PARK REPLAT 2 Beds 2 Baths 1,056 SqFt 1 DOM Residential MLS® # A4617219
New
3430 Jaffa Drive, SARASOTA

$435,000

3430 Jaffa Drive, SARASOTA

SOUTH GATE 3 Beds 2 Baths 1,624 SqFt 2 DOM Residential MLS® # A4616125
New
2525 Floyd Street, SARASOTA

$465,000

2525 Floyd Street, SARASOTA

RUSTIC LODGE 3 Beds 2 Baths 1,193 SqFt 3 DOM Residential MLS® # A4617999
New
4108 Nelson Avenue, SARASOTA

$324,900

4108 Nelson Avenue, SARASOTA

DIXIE HEIGHTS 2 Beds 1 Bath 841 SqFt 3 DOM Residential MLS® # A4617863
New
1620 Assisi Drive 19, SARASOTA

$2,390,000

1620 Assisi Drive 19, SARASOTA

PORTOFINO ON THE BAY 4 Beds 4 Baths 3,039 SqFt 4 DOM Residential MLS® # T3543258
New
1701 Hillview Street, SARASOTA

$2,199,000

1701 Hillview Street, SARASOTA

NICHOLS SARASOTA HEIGHTS 4 Beds 3 Baths 2,545 SqFt 4 DOM Residential MLS® # A4617068
New
5324 Carmilfra Drive, SARASOTA

$1,120,000

5324 Carmilfra Drive, SARASOTA

RIVER FOREST 3 Beds 2 Baths 1,953 SqFt 5 DOM Residential MLS® # A4617801
New
6225 Green View Drive 124, SARASOTA

$225,000

6225 Green View Drive 124, SARASOTA

VILLAGE IN THE PINES 1 2 Beds 2 Baths 1,545 SqFt 6 DOM Residential MLS® # A4612990
New
6103 Carlton Avenue, SARASOTA

$385,000

6103 Carlton Avenue, SARASOTA

DENHAM ACRES 2 Beds 2 Baths 1,014 SqFt 6 DOM Residential MLS® # A4617262
New
3216 Gulf Watch Court, SARASOTA

$429,000

3216 Gulf Watch Court, SARASOTA

GULF GATE GLEN 2 Beds 2 Baths 1,214 SqFt 6 DOM Residential MLS® # A4617064
New
2632 Hawthorne Street, SARASOTA

$599,000

2632 Hawthorne Street, SARASOTA

HYDE PARK HEIGHTS 1 2 Beds 1 Bath 625 SqFt 7 DOM Residential MLS® # A4617528
New
2633 Marlette Street, SARASOTA

$695,000

2633 Marlette Street, SARASOTA

FOREST HILLS 3 Beds 3 Baths 1,700 SqFt 7 DOM Residential MLS® # A4617174
New
1681 Bahia Vista Street, SARASOTA

$998,000

1681 Bahia Vista Street, SARASOTA

BUNGALOW HILL 3 Beds 2 Baths 1,568 SqFt 7 DOM Residential MLS® # A4616816
New
2026 Pine Terrace, SARASOTA

$1,500,000

2026 Pine Terrace, SARASOTA

HARBOR OAKS 5 Beds 3 Baths 3,972 SqFt 7 DOM Residential MLS® # N6133815
4444 Swift Road 19, SARASOTA

$134,777

4444 Swift Road 19, SARASOTA

LUCAYA COUNTRY CLUB VILLAGE 1 Bed 1 Bath 403 SqFt 8 DOM Residential MLS® # A4617486
2314 Prospect Street, SARASOTA

$1,985,000

2314 Prospect Street, SARASOTA

LOMA LINDA PARK 4 Beds 6 Baths 3,651 SqFt 8 DOM Residential MLS® # A4617182
5795 Summerside 7a, SARASOTA

$279,900

5795 Summerside 7a, SARASOTA

SUMMERSIDE 2 Beds 2 Baths 1,125 SqFt 8 DOM Residential MLS® # A4617468
2532 Sunnybrook Drive, SARASOTA

$744,900

2532 Sunnybrook Drive, SARASOTA

SOUTHGATE 3 Beds 3 Baths 1,980 SqFt 8 DOM Residential MLS® # A4617441
2830 Gypsy Street, SARASOTA

$415,000

2830 Gypsy Street, SARASOTA

SARASOTA VENICE CO 09 37 18 2 Beds 1 Bath 1,032 SqFt 8 DOM Residential MLS® # T3542079

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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