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You are here: Home / West of the Trail Homes for Sale | Sarasota Florida

West of the Trail Homes for Sale | Sarasota Florida

West of the Trail is one of the most prestigious residential districts in Sarasota. Often compared to iconic neighborhoods such as Central Park West in New York, Bel Air in Los Angeles, Coconut Grove in Miami, and Buckhead in Atlanta, West of the Trail has become one of the most desirable places to live in Southwest Florida.

Rather than being a single neighborhood, West of the Trail is a collection of approximately 30 residential communities where buyers can find some of Sarasota’s most attractive real estate. The district is known for its architectural diversity, charming tree-lined streets, and exceptional quality of life.

West of the Trail Sarasota Neighborhoods

The geographical heart of West of the Trail surrounds Sarasota Memorial Hospital, which is one reason many physicians and medical professionals choose to live in the area. The district is generally defined by U.S. 41, also known as the Tamiami Trail, and stretches from Laurel Park in the north to Bayview Heights in the south, extending west toward Sarasota Bay.

Several well-known neighborhoods contribute to the appeal of West of the Trail. San Remo Estates features spectacular Mediterranean-inspired estates and waterfront properties. The historic neighborhood of Cherokee Park offers a classic Old Florida atmosphere with mature trees and charming homes.

Younger buyers are often drawn to Bungalow Hill, a trendy neighborhood known for its walkable streets and renovated historic homes.

Location and Lifestyle

West of the Trail enjoys a prime location close to many of Sarasota’s most desirable destinations. Homes closer to Downtown Sarasota tend to attract the most attention from buyers due to their proximity to restaurants, theaters, galleries, and waterfront parks.

The district is also known as one of Sarasota’s most pedestrian-friendly areas. Residents often walk or bike to nearby beaches, shopping areas, fitness studios, restaurants, museums, and entertainment venues.

Whether you are looking to raise a family, retire near the coast, or invest in highly desirable Sarasota real estate, West of the Trail offers a wide variety of homes in one of the city’s most sought-after locations.

Homes for Sale West of the Trail Sarasota

West of the Trail continues to attract buyers seeking historic charm, waterfront living, and convenient access to Sarasota’s cultural and coastal lifestyle. View current West of the Trail Sarasota homes for sale below if inventory is available.

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West of the Trail Sarasota FAQ

What is West of the Trail in Sarasota?

West of the Trail is a prestigious residential district in Sarasota located west of U.S. 41 between Downtown Sarasota and the southern neighborhoods near Bayview Heights.

Why is West of the Trail popular?

The area is known for its proximity to Sarasota Bay, historic neighborhoods, walkable lifestyle, and convenient access to downtown restaurants, shopping, and cultural attractions.

What types of homes are found West of the Trail?

Homes in the district range from historic bungalows and ranch-style houses to luxury waterfront estates and new construction homes.

Is West of the Trail close to downtown Sarasota?

Yes. Many neighborhoods West of the Trail are just minutes from Downtown Sarasota.

What neighborhoods are part of West of the Trail?

Popular neighborhoods include San Remo Estates, Cherokee Park, Bungalow Hill, Laurel Park, and Bayview Heights.

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The Wendy Lynn Group Sarasota exp Realty



  • 1300 Main Street, Sarasota, FL 34236

  • 941-421-7375

  • info@sunnysarasotahomes.com

Sarasota Neighborhoods

  • Amberlea
  • Ashley
  • Artistry
  • Ashton Pointe
  • Bay Landing
  • Beechwood Estates
  • Beekman Place
  • Bent Tree
  • Bird Key
  • Cascades
  • Cassia Skye Ranch
  • Center Gate
  • Colonial Oaks
  • Country Place
  • Deerfield
  • Desoto Acres
  • Downtown Sarasota
  • Esplanade at Skye Ranch
  • Esplanade by Siesta Key
  • Forest at Hi Hat Ranch
  • Forest Lakes CC
  • Founders Club
  • Foxfire
  • Golden Gate Point
  • Grady Pointe
  • Grand Park
  • Gulf Gate
  • Hammocks
  • Hampton Lakes
  • Hawkstone
  • Heritage Oaks
  • Hidden Forest
  • Hidden Oaks
  • Hidden River
  • Kensington Park
  • Lakeridge Falls
  • Lakeshore Village
  • Laurel Lakes
  • Laurel Oak
  • Lido Key
  • Longwood Run
  • Meadows
  • Misty Creek
  • Mote Ranch
  • Oak Vistas
  • Old Forest Lakes
  • Paddocks
  • Palm Aire
  • Palm Lakes
  • Palmer Ranch
  • Pelican Cove
  • Riva Trace
  • River Forest
  • Rivetta
  • Saddle Creek
  • San Palermo
  • Sarasota Polo Club
  • Secluded Oaks
  • Serenoa
  • Shadow Oaks
  • Siesta Key
  • Skye Ranch
  • Soleil
  • Sunrise Golf Club
  • Sylvan Lea
  • University Park CC
  • University Place
  • Vilano
  • Waverley
  • West of the Trail
  • Wildgrass
  • Woodbrook
  • Worthington

Areas We Serve

  • Anna Maria
  • Bird Key
  • Bradenton
  • Bradenton Beach
  • Casey Key
  • Cortez
  • Downtown Sarasota
  • Ellenton
  • Englewood
  • Golden Gate
  • Holmes Beach
  • Lakewood Ranch
  • Lido Key
  • Longboat Key
  • Myakka City
  • Nokomis
  • North Port
  • Osprey
  • Palmer Ranch
  • Palmetto
  • Parrish
  • Sarasota
  • Siesta Key
  • South Hillsborough
  • Terra Ceia
  • University Park
  • Venice
  • West of the Trail

Things to do in Sarasota Florida

https://www.youtube.com/watch?v=IbMIeepUL5I&t=33s

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The Wendy Lynn Group Sarasota exp Realty

  • 1300 Main Street, Sarasota, FL 34236
  • 941-421-7375
  • info@sunnysarasotahomes.com

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Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
4 Jul 2073497513731190917

Thank you so much for the review! So greatly appreciated!!!

https://rma.reviews/6mahrsi1bzj6

...
#sold #wendylynngroup #realtor #sarasota #bradenton #srq #lwr #realestate #clientreview 5★★★★★Excellent experience from start to finish!RateMyAgent🛌 2 🛀 3 🚘 1ies

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Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
3 Jul 2073134970227548205

Thank you so much for the review! So greatly appreciated!!!

https://rma.reviews/rej5ze48n5ec

...
#sold #wendylynngroup #realtor #sarasota #bradenton #srq #lwr #realestate #clientreview 5★★★★★Five-Star Service from Wendy and Her TeamRateMyAgent🛌 3 🛀 2 🚘 2ies

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Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
3 Jul 2073017698611581330

Bradenton�s riverfront areas remain attractive to long-term residents.,#BradentonFlorida,

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Bradenton FL Homes for Sale | Bradenton Real Estate

Search Bradenton FL homes for sale including condos, golf, waterfront, and 55+ communities. Browse listings by price and neighborhood.

www.sunnysarasotahomes.com

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
2 Jul 2072655323307917666

Gated communities continue offering security and amenity-driven appeal.,#GatedCommunities,

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Homes for Sale in Gated Communities of Manatee & Sarasota County

This preconfigured search includes Gated Community Homes for Sale in Manatee & Sarasota County including Lakewood Ranch & the Sarasota Keys.

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Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
1 Jul 2072292945118531841

Price reductions are strategic tools when used correctly � not signals of weakness.,#PricingStrategy,https://www.wendylynngroup.com/market-report.php

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
30 Jun 2071930529180528778

Siesta Key�s global recognition continues to drive interest.,#SiestaKey,

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Siesta Key Homes for Sale | Siesta Key Florida Real Estate

Search Siesta Key homes for sale including beachfront condos, waterfront estates, and resort-style communities on one ...

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