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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.

1703 ALTA VISTA STREET SARASOTA FL 34236
New Listing - 22 hours on site
1 / 9
$1,300,000
Land For Sale
Active
0.2
ACRES
SARASOTA
COUNTY
1703 ALTA VISTA STREET
SARASOTA, FL 34236
PRIME SUB Subdivision
3711 ALMERIA AVENUE 3N SARASOTA FL 34239
New Listing - yesterday
1 / 24
$285,000
Condominium For Sale
Active
2
BEDS
2
TOTAL BATHS
976
SQFT
3711 ALMERIA AVENUE 3N
SARASOTA, FL 34239
GRANADA Subdivision
1525 MALLARD LANE SARASOTA FL 34239
New Listing - 6 days on site
1 / 100
$8,250,000
Single Family Residence For Sale
Active
5
BEDS
6
TOTAL BATHS
5,664
SQFT
1525 MALLARD LANE
SARASOTA, FL 34239
PARADISE SHORES Subdivision
1800 WEBBER STREET SARASOTA FL 34239
New Listing - a week on site
1 / 76
$4,790,000
Single Family Residence For Sale
Active
4
BEDS
6
TOTAL BATHS
3,262
SQFT
1800 WEBBER STREET
SARASOTA, FL 34239
POINSETTIA PARK 2 Subdivision
850 S TAMIAMI TRAIL 207 SARASOTA FL 34236
New Listing - 2 weeks on site
1 / 29
$198,000
Condominium For Sale
Active
1
BED
1
TOTAL BATH
576
SQFT
850 S TAMIAMI TRAIL 207
SARASOTA, FL 34236
CENTRAL PARK SEC 2 PH 1 Subdivision
1537 SIESTA DRIVE SARASOTA FL 34239
New Listing - 2 weeks on site
1 / 84
$3,100,000
Single Family Residence For Sale
Active
4
BEDS
6
TOTAL BATHS
3,727
SQFT
1537 SIESTA DRIVE
SARASOTA, FL 34239
SUNSET BAY SUB Subdivision
1885 CLEMATIS STREET SARASOTA FL 34239
New Listing - 3 weeks on site
1 / 50
$2,599,990
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
3,215
SQFT
1885 CLEMATIS STREET
SARASOTA, FL 34239
DESOTA PARK Subdivision
850 S TAMIAMI TRAIL 604 SARASOTA FL 34236
New Listing - 3 weeks on site
1 / 90
$299,500
Condominium For Sale
Active
2
BEDS
2
TOTAL BATHS
980
SQFT
850 S TAMIAMI TRAIL 604
SARASOTA, FL 34236
CENTRAL PARK SEC 2 PH 1 Subdivision
1824 WEBBER STREET SARASOTA FL 34239
New Listing - 3 weeks on site
1 / 17
$650,000
Residential For Sale
Active
4
BEDS
4
TOTAL BATHS
1,680
SQFT
1824 WEBBER STREET
SARASOTA, FL 34239
POINSETTIA PARK 2 Subdivision
1734 WISCONSIN LANE SARASOTA FL 34239
New Listing - 4 weeks on site
1 / 52
$1,650,000
Single Family Residence For Sale
Active
4
BEDS
5
TOTAL BATHS
2,910
SQFT
1734 WISCONSIN LANE
SARASOTA, FL 34239
BAYVIEW Subdivision
1731 SIESTA DRIVE SARASOTA FL 34239
New Listing - 4 weeks on site
1 / 41
$2,595,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
3,200
SQFT
1731 SIESTA DRIVE
SARASOTA, FL 34239
BAYVIEW Subdivision
1702 WALDEMERE STREET SARASOTA FL 34239
New Listing - 4 weeks on site
1 / 16
$1,375,000
Land For Sale
Active
0.25
ACRES
SARASOTA
COUNTY
1702 WALDEMERE STREET
SARASOTA, FL 34239
HUDSON BAYOU Subdivision
1702 WALDEMERE STREET SARASOTA FL 34239
New Listing - 4 weeks on site
1 / 16
$1,375,000
Single Family Residence For Sale
Active
2
BEDS
1
TOTAL BATH
991
SQFT
1702 WALDEMERE STREET
SARASOTA, FL 34239
HUDSON BAYOU Subdivision
1931 HIGH POINT CIRCLE SARASOTA FL 34236
1 / 39
$1,495,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,712
SQFT
1931 HIGH POINT CIRCLE
SARASOTA, FL 34236
HUDSON BAYOU Subdivision
1704 FORTUNA STREET SARASOTA FL 34239
1 / 47
$1,475,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
2,435
SQFT
1704 FORTUNA STREET
SARASOTA, FL 34239
GRANADA Subdivision
1717 ALTA VISTA STREET SARASOTA FL 34236
Open House Sat, May 23, 12 PM
1 / 43
$3,500,000
Single Family Residence For Sale
Active
5
BEDS
5
TOTAL BATHS
3,267
SQFT
1717 ALTA VISTA STREET
SARASOTA, FL 34236
PRIME SUB Subdivision
1880 LOMA LINDA STREET SARASOTA FL 34239
1 / 38
$1,895,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
2,904
SQFT
1880 LOMA LINDA STREET
SARASOTA, FL 34239
FLOYD & CAMERON SUB Subdivision
1751 HAWTHORNE STREET SARASOTA FL 34239
1 / 39
$2,495,000
Single Family Residence For Sale
Active
4
BEDS
4
TOTAL BATHS
3,875
SQFT
1751 HAWTHORNE STREET
SARASOTA, FL 34239
HUDSON BAYOU Subdivision
3700 S OSPREY AVENUE 115 SARASOTA FL 34239
Price Change - 3 weeks ago
1 / 30
$199,000
Condominium For Sale
Active
2
BEDS
1
TOTAL BATH
991
SQFT
3700 S OSPREY AVENUE 115
SARASOTA, FL 34239
PLAZA GARDENS Subdivision
1714 WALDEMERE STREET SARASOTA FL 34239
1 / 28
$1,800,000
Single Family Residence For Sale
Active
4
BEDS
3
TOTAL BATHS
2,003
SQFT
1714 WALDEMERE STREET
SARASOTA, FL 34239
HUDSON BAYOU Subdivision

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 Lynn on X

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
2h 2057072632810324292

Buyer activity in Sarasota remains steady despite rate shifts. Demand has not disappeared � it has become more selective.,#MarketUpdate #SarasotaRealEstate,https://www.wendylynngroup.com/market-report.php

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
19 May 2056710239227932896

Bird Key remains one of Sarasota�s most exclusive waterfront enclaves.,#BirdKey,

Image for twitter card

Bird Key Homes for Sale | Sarasota Waterfront Real Estate

Bird Key homes for sale in one of Sarasota’s most exclusive waterfront neighborhoods near Downtown Sarasota and Lido Key.

www.sunnysarasotahomes.com

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
18 May 2056347846731829748

"Before making a move, confirm your numbers. Clarity creates confidence.",#SellerStrategy,https://www.wendylynngroup.com/seller/valuation/

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
15 May 2055260683525132314

Ellenton continues expanding with both affordability and accessibility advantages.,#EllentonFlorida,

Image for twitter card

Ellenton Homes for Sale | Ellenton Florida Real Estate

Explore Ellenton homes for sale, neighborhoods, and real estate options in this growing Manatee County community near Bradenton and the Manatee River.

www.sunnysarasotahomes.com

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
14 May 2054898333865378296

Waterfront demand in Sarasota County remains steady across multiple price points.,#WaterfrontHomes,

Image for twitter card

Waterfront Homes for Sale in Manatee and Sarasota County

Waterfront Homes for Sale in Manatee and Sarasota County

www.sunnysarasotahomes.com

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
13 May 2054535904849453500

Every market cycle presents opportunity for those paying attention.,#MarketUpdate,https://www.wendylynngroup.com/market-report.php

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