| Address | Price | Bed / Bths | Interior Space | $sf | WF / Pool | MLS |
|---|---|---|---|---|---|---|
| 1310 S LAKE SHORE DRIVE |
$26,400,000 | 4/4 |
10,697sf | $2,468 | Y / Y | A4673508 |
| 1204 HILLVIEW DRIVE |
$21,000,000 | 6/7 |
7,687sf | $2,732 | Y / Y | A4677344 |
| 1423 & 1435 HILLVIEW DRIVE |
$17,350,000 | 6/7 |
11,588sf | $1,497 | Y / Y | A4653958 |
| 1521 BAY POINT DRIVE |
$14,900,000 | 4/4 |
6,429sf | $2,318 | Y / Y | A4677001 |
| 3000 SOUTHWEST DRIVE |
$13,250,000 | 5/4 |
8,125sf | $1,631 | Y / Y | A4672971 |
| 1340 HARBOR DRIVE |
$10,995,000 | 4/5 |
5,157sf | $2,132 | Y / Y | A4680096 |
| 3621 SAN REMO TERRACE |
$9,450,000 | 5/5 |
5,328sf | $1,774 | Y / Y | A4592737 |
| 3631 SAN REMO TERRACE |
$8,795,000 | 0/ |
4,705sf | $1,869 | Y / Y | A4669078 |
| 3950 RED ROCK WAY |
$7,999,999 | 0/ |
6,850sf | $1,168 | Y / Y | A4669105 |
| 1808 FLOWER DRIVE |
$7,950,000 | 4/3 |
5,450sf | $1,459 | Y / Y | A4669396 |
| 1540 HILLVIEW DRIVE |
$7,900,000 | 4/6 |
7,074sf | $1,117 | Y / Y | A4679306 |
| 1444 HARBOR DRIVE |
$7,500,000 | 5/5 |
5,001sf | $1,500 | N / Y | O6375298 |
| 1541 BAY POINT DRIVE |
$7,499,000 | 4/4 |
6,368sf | $1,178 | Y / Y | A4634377 |
| 1137 N LAKE SHORE DRIVE |
$6,695,000 | 6/6 |
6,462sf | $1,036 | Y / Y | A4641614 |
| 1365 HARBOR DRIVE |
$6,375,000 | 4/4 |
4,978sf | $1,281 | N / Y | A4672827 |
| 1521 S LAKE SHORE DRIVE |
$6,290,000 | 4/5 |
4,866sf | $1,293 | N / Y | A4637673 |
| 1389 TANGIER WAY |
$6,250,000 | 4/4 |
5,310sf | $1,177 | Y / Y | A4677509 |
| 2100 MCCLELLAN PARKWAY |
$6,000,000 | 5/7 |
4,765sf | $1,259 | N / Y | A4682267 |
| 1804 N LAKE SHORE DRIVE |
$5,800,000 | 4/4 |
6,854sf | $846 | N / Y | A4679067 |
| 3576 SAN REMO TERRACE |
$5,799,995 | 4/4 |
6,091sf | $952 | Y / Y | A4652012 |
| 1479 BAY POINT DRIVE |
$5,695,000 | 4/3 |
3,783sf | $1,505 | Y / Y | A4647998 |
| 1429 N LAKE SHORE DRIVE |
$5,695,000 | 5/5 |
4,545sf | $1,253 | N / Y | A4674740 |
| 1821 LINCOLN DRIVE |
$5,425,000 | 4/4 |
3,906sf | $1,389 | Y / Y | A4669453 |
| 1509 FLOWER DRIVE |
$5,375,000 | 5/4 |
4,989sf | $1,077 | N / Y | A4665815 |
| 4431 CAMINO REAL |
$4,900,000 | 4/4 |
3,787sf | $1,294 | Y / Y | A4626321 |
| 1421 N LAKE SHORE DRIVE |
$4,895,000 | 4/4 |
4,217sf | $1,161 | N / Y | A4674749 |
| 1519 HARBOR DRIVE |
$4,750,750 | 4/4 |
3,970sf | $1,197 | N / Y | A4672376 |
| 1516 S ORANGE AVENUE |
$4,750,750 | 4/4 |
4,224sf | $1,125 | N / Y | A4676686 |
| 1575 EASTBROOK DRIVE |
$4,700,000 | 4/5 |
4,087sf | $1,150 | Y / Y | A4643636 |
| 1347 HARBOR DRIVE |
$4,696,600 | 5/4 |
4,069sf | $1,154 | N / Y | A4679697 |
| 1607 FLOWER DRIVE |
$4,695,000 | 5/6 |
4,769sf | $984 | N / Y | A4653737 |
| 1349 HARBOR DRIVE |
$4,550,000 | 4/4 |
4,337sf | $1,049 | N / Y | A4676231 |
| 1729 CHEROKEE DRIVE |
$4,450,000 | 4/4 |
4,353sf | $1,022 | N / Y | A4682051 |
| 1542 GULFVIEW DRIVE |
$3,850,000 | 2/2 |
2,156sf | $1,786 | Y / N | A4673664 |
| 1543 EASTBROOK DRIVE |
$3,750,000 | 4/5 |
4,788sf | $783 | Y / Y | A4641145 |
| 1838 ALTA VISTA STREET |
$3,495,000 | 5/4 |
4,452sf | $785 | N / Y | A4657794 |
| 4439 WESTWOOD LANE |
$3,345,000 | 4/3 |
3,777sf | $886 | N / Y | A4664741 |
| 1705 FIELD ROAD |
$2,939,000 | 4/3 |
2,400sf | $1,225 | N / N | A4671008 |
| 3500 FLORES AVENUE |
$2,800,000 | 4/3 |
3,551sf | $789 | N / Y | A4663143 |
| 3512 CAMINO REAL |
$2,795,000 | 5/4 |
3,810sf | $734 | N / Y | A4671290 |
| 3606 PALONIA COURT |
$2,700,000 | 3/2 |
2,700sf | $1,000 | N / Y | A4677263 |
| 1801 FIELD ROAD |
$2,695,000 | 3/4 |
3,035sf | $888 | N / Y | A4653272 |
| 1511 N LAKE SHORE DRIVE |
$2,399,000 | 4/3 |
3,613sf | $664 | N / Y | A4674572 |
| 1695 HYDE PARK STREET |
$2,195,000 | 3/2 |
2,939sf | $747 | N / N | A4679534 |
| 3705 TANGIER TERRACE |
$2,190,000 | 4/3 |
2,529sf | $866 | N / Y | A4679205 |
| 1826 BOYCE STREET |
$2,150,000 | 5/5 |
3,270sf | $657 | N / Y | TB8459204 |
| 1846 LINCOLN DRIVE |
$2,095,000 | 3/3 |
2,618sf | $800 | N / Y | A4666374 |
| 1538 S ORANGE AVENUE |
$1,950,000 | 0/ |
2,550sf | $765 | N / N | A4672485 |
| 1541 FLOWER DRIVE |
$1,900,000 | 4/4 |
3,302sf | $575 | N / N | A4656365 |
| 1389 HARBOR DRIVE |
$1,750,000 | 3/2 |
2,376sf | $737 | N / Y | A4623196 |
| 1740 S ORANGE AVENUE |
$1,700,000 | 4/4 |
3,168sf | $537 | N / Y | A4679755 |
| 3838 FLORES AVENUE |
$1,545,000 | 5/4 |
3,033sf | $509 | N / Y | A4661399 |
| 1958 MORRIS STREET |
$1,450,000 | 4/3 |
2,362sf | $614 | N / Y | A4677121 |
| 1917 BAHIA VISTA STREET |
$1,195,000 | 4/3 |
2,160sf | $553 | N / Y | A4676931 |
| 3837 CAMINO REAL |
$1,045,000 | 3/3 |
1,887sf | $554 | N / N | A4672440 |
Discover Sarasota's West of Trail Neighborhood: A Timeless Blend of Waterfront Beauty and Urban Elegance
West of Trail in Sarasota, Florida, is one of the city's most desirable residential enclaves — a prestigious corridor that stretches between U.S. 41 and Sarasota Bay, offering an elegant fusion of Old Florida character and modern coastal luxury. Known for its tree-lined streets, deep-water canals, and proximity to downtown, West of Trail represents the pinnacle of Sarasota living. The area includes celebrated neighborhoods such as Avondale, Bay Haven, Bay Island, Bay Isles, Bay Point Park, and Bird Key, each delivering its own unique blend of architecture, history, and waterfront access.
Prime Location Near Downtown Sarasota and the Bay
Located just minutes south of Downtown Sarasota, West of Trail enjoys the perfect balance between tranquility and convenience. Residents are only a short drive or bike ride from Marina Jack, Bayfront Park, and the downtown arts district, yet they live in peaceful residential surroundings filled with mature oak trees and lush landscaping. The John Ringling Causeway provides quick access to Lido Key Beach and St. Armands Circle, while Siesta Key Beach — world-famous for its white quartz sand — is only a few miles away. This central yet secluded setting makes West of Trail ideal for those who desire luxury coastal living without sacrificing proximity to Sarasota’s vibrant downtown amenities.
Architectural Diversity and Waterfront Estates
West of Trail real estate is among the most exclusive in Sarasota. The area features a stunning mix of architectural styles — from classic mid-century ranch homes and Key West-inspired cottages to newly built modern estates with sleek lines and floor-to-ceiling glass. Waterfront properties offer private docks, sailboat water, and direct access to Sarasota Bay and the Gulf of Mexico. Neighborhoods like Bay Island Shores and Bay Isles are especially coveted for their boating access, while Avondale and Bay Haven showcase timeless character and walkable streets near Southside Village. Many homes have been completely reimagined with open-concept interiors, resort-style pools, and outdoor kitchens that make the most of Florida’s indoor-outdoor lifestyle.
Elegant Lifestyle and Walkable Surroundings
Living West of Trail means enjoying an elegant, walkable lifestyle enhanced by nearby shops, restaurants, and wellness amenities. Southside Village — located near Morton’s Gourmet Market — serves as a charming hub for locals, offering upscale dining, boutique shopping, and a friendly community atmosphere. Residents can walk or bike to Selby Gardens, The Bay Park, or the waterfront trails of Downtown Sarasota, blending relaxation and recreation effortlessly. The neighborhood’s proximity to Sarasota Memorial Hospital adds convenience and peace of mind, especially for professionals and families who value both luxury and accessibility.
Fine Dining and Cultural Attractions
From West of Trail, Sarasota’s top cultural venues are just minutes away. Enjoy world-class performances at the Sarasota Opera House, Florida Studio Theatre, or Van Wezel Performing Arts Hall, all within easy reach. Culinary enthusiasts appreciate the area’s proximity to Selva Grill, Indigenous, and Bijou Garden Café, as well as neighborhood favorites like Owen’s Fish Camp and Libby’s. Weekly visits to the Downtown Farmers Market or evenings spent dining al fresco beneath Sarasota’s starry skies are part of everyday life for West of Trail residents.
Outdoor Recreation and Coastal Access
With Sarasota Bay as its western boundary, West of Trail offers abundant opportunities for boating, kayaking, paddleboarding, and fishing. Residents enjoy easy access to private marinas, neighborhood boat launches, and the Intracoastal Waterway. The area’s proximity to Siesta Key Beach and Lido Key Beach ensures year-round access to the Gulf’s turquoise waters. For those who prefer land-based recreation, nearby Payne Park and Arlington Park provide tennis courts, walking paths, and green spaces ideal for family outings and active lifestyles.
Schools, Healthcare, and Community
Families are drawn to West of Trail for its excellent schools and sense of community. The neighborhood is served by top-rated institutions including Southside Elementary, Brookside Middle, and Riverview High School. Sarasota Memorial Hospital, one of Florida’s highest-ranked medical facilities, is conveniently located within the district. West of Trail also enjoys a close-knit neighborhood association network, frequent community gatherings, and a warm, welcoming atmosphere that blends luxury living with genuine small-town charm.
Timeless Value and Investment Appeal
As Sarasota continues to grow, West of Trail remains one of the city’s most stable and valuable real estate markets. Its limited inventory, proximity to downtown, and waterfront access ensure consistent demand among buyers seeking primary or seasonal residences. Many properties appreciate rapidly due to the area’s enduring prestige and redevelopment potential. Whether you’re searching for a new modern masterpiece or a classic coastal retreat, investing West of Trail is investing in Sarasota’s most iconic and enduring lifestyle.
Experience the Best of Sarasota's West of Trail
Few areas capture the essence of Sarasota living quite like West of Trail — where graceful architecture, lush landscaping, and coastal charm meet walkable convenience and urban sophistication. From the waterfront estates of Bird Key and Bay Island to the historic streets of Avondale and Bay Haven, this area embodies timeless luxury. Discover why West of Trail continues to define the standard for Sarasota’s finest homes and lifestyles.
Explore Sarasota’s West of Trail — a community where luxury, lifestyle, and location align perfectly.
For expert guidance on Sarasota’s premier West of Trail homes, contact Lisa Otte at 941.281.5472 or E-mail lisa@sarasotaluxurycondos.com.
Available Properties in West Of Trail
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