Area Guide
West of Trail
Sarasota's most coveted mainland luxury corridor
About West of Trail
West of Trail is the stretch of mainland Sarasota between US 41 and the bay, and the core of it is the city's original neighborhood fabric: oak canopy and brick-accented streets laid out a century ago, with housing that runs from 1920s bungalows to new modern builds, often side by side on the same block. Cherokee Park, McClellan Park and Harbor Acres carry the estate streets toward the water; Avondale and Granada keep the original cottage scale, and Granada's quiet courts off Osprey Avenue still hold some of the city's best surviving 1920s bungalows. The center of daily life is Southside Village, the shopping and dining district along S Osprey Avenue anchored by Morton's Gourmet Market. Residents enjoy the convenience to Southside Village gourmet grocery and boutique dining with the comforts of mainland living: real lots, mature trees, the historic Southside School, and Sarasota Memorial Hospital a few blocks away. The bayfront, downtown and the Siesta Key bridges are all minutes out, which is why West of Trail remains the first place mainland buyers look and the last place owners want to leave.
Sold + Pending Activity
West of Trail Closed Market Snapshot
Averages across 211 sold and 25 pending listings in the West of Trail submarket. Pre-list and withdrawn activity excluded. Price range: $3,150 – $26,400,000.
| Metric | Value |
|---|---|
| Average Price | $2,429,757 |
| Average Price / Sq Ft | $725 |
| Average Year Built | 1985 |
| Average Living Area | 2,981 sq ft |
| Average Days on Market | 120 days |
Data sourced from Stellar MLS via the Adamson Group data pipeline. Last updated September 10, 2026.
Active Market Snapshot
West of Trail Active Inventory & Recent Sales
A live snapshot of the West of Trail luxury real estate market, built directly from the Sarasota MLS feed and refreshed regularly. Data through September 10, 2026.
Active Inventory
- Active Listings
- 74
- Median List Price
- $3,097,500
- Median Price / Sq Ft
- $912
- Waterfront Share
- 24%
Of 74 active listings, 18 are waterfront (24%) and 29 are new construction built in 2020 or later (39%).
Active Inventory by Price Band
| Price Band | Active Listings |
|---|---|
| Under $900k | 8 |
| $900k – $1.5M | 5 |
| $1.5M – $3M | 23 |
| $3M and above | 38 |
Recent Sold Activity (Last 90 Days)
- Sold Listings
- 35
- Median Sold Price
- $1,825,000
- Median Days on Market
- 124
- Sale-to-List Ratio
- 85.9%
Most Recent Sold Comparables (Last 90 Days)
| Address | Sold | Date | Bd / Ba | Sq Ft | Built |
|---|---|---|---|---|---|
| 4431 CAMINO REAL(waterfront)OYSTER BAY ESTATES | $4,225,000 | 2026-09-10 | 4 / 4.5 | 3,787 | 2026 |
| 3319 S OSPREY AVEPOINSETTIA PARK 2 | $1,750,000 | 2026-09-09 | 4 / 4.5 | 3,554 | 2023 |
| 1862 PROSPECT STFLOYD & CAMERON SUB | $2,575,000 | 2026-09-04 | 3 / 3.5 | 2,439 | 1928 |
| 1711 KENILWORTH ST(waterfront)KENILWORTH ESTATES | $1,435,000 | 2026-09-04 | 4 / 3 | 3,734 | 2013 |
| 1610 N LODGE DR(waterfront)CHEROKEE LODGE | $10,140,000 | 2026-09-03 | 5 / 6.5 | 7,110 | 2024 |
Active inventory and recent sold data sourced directly from the Sarasota Stellar MLS feed via the Adamson Group data pipeline. Geographic boundaries enforced via PostGIS: listings are assigned to West of Trail based on actual coordinates, not just postal code. Data through September 10, 2026. All figures approximate and subject to change.
West of Trail Market Questions & FAQ
Is West Of Trail Core a buyer's or seller's market right now?
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With 74 active listings and roughly 13 closed sales a month (trailing 12 months), West Of Trail Core has about 5.6 months of supply — a balanced market (under 5 favors sellers, over 7 favors buyers).
What's the price range on West Of Trail Core?
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Active listings run from $3,150 to $26,400,000, with a median asking price of $3,097,500.
How quickly do homes sell on West Of Trail Core?
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Recently sold homes took a median 124 days on market and closed at 85.9% of original list price (trailing 90 days).
Can I keep a boat — how many West Of Trail Core homes have a dock?
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Of 18 active waterfront listings, 14 include a private dock; bay- and canal-front homes with a dock and lift command a clear premium over those without.
What is West of Trail in Sarasota?
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West of Trail refers to the mainland luxury district immediately west of US-41 (the Tamiami Trail) and south of downtown Sarasota. The core area includes Cherokee Park, Hudson Bayou, McClellan Park, Avondale, Granada, and Oyster Bay: Sarasota's most established residential corridor, where legacy 1920s bungalows sit alongside new modern builds.
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