Area Guide
West of Trail
Sarasota's most coveted mainland luxury corridor
About West of Trail
West of Trail is the legacy luxury mainland district immediately south of downtown Sarasota and west of US-41 (the Tamiami Trail). The core stretches from Mound Street south through neighborhoods like Cherokee Park, Hudson Bayou, McClellan Park, Avondale, and Oyster Bay — tree-lined streets, mid-century estates, and a tight inventory of high-end single-family homes within walking or biking distance of the bayfront and Southside Village.
Sold + Pending Activity
West of Trail Closed Market Snapshot
Averages across 193 sold and 16 pending listings in the West of Trail submarket. Pre-list and withdrawn activity excluded. Price range: $98,000 – $26,400,000.
| Metric | Value |
|---|---|
| Average Price | $2,339,694 |
| Average Price / Sq Ft | $715 |
| Average Year Built | 1985 |
| Average Living Area | 2,941 sq ft |
| Average Days on Market | 116 days |
Data sourced from Stellar MLS via the Adamson Group data pipeline. Last updated July 20, 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 July 20, 2026.
Active Inventory
- Active Listings
- 94
- Median List Price
- $3,247,500
- Median Price / Sq Ft
- $915
- Waterfront Share
- 28%
Of 94 active listings, 26 are waterfront (28%) and 36 are new construction built in 2020 or later (38%).
Active Inventory by Price Band
| Price Band | Active Listings |
|---|---|
| Under $900k | 13 |
| $900k – $1.5M | 5 |
| $1.5M – $3M | 25 |
| $3M and above | 51 |
Recent Sold Activity (Last 90 Days)
- Sold Listings
- 51
- Median Sold Price
- $2,125,000
- Median Days on Market
- 93
- Sale-to-List Ratio
- 103.5%
Most Recent Sold Comparables (Last 90 Days)
| Address | Sold | Date | Bd / Ba | Sq Ft | Built |
|---|---|---|---|---|---|
| 1740 S ORANGE AVEHARBOR ACRES SEC 2 | $1,325,700 | 2026-07-17 | 4 / 4.5 | 3,168 | 1967 |
| 866 HUDSON AVE #866(waterfront)HUDSON LANDINGS | $1,250,000 | 2026-07-17 | 4 / 3 | 2,293 | 1989 |
| 4439 WESTWOOD LNOYSTER BAY ESTATES | $2,768,500 | 2026-07-16 | 4 / 3.5 | 3,777 | 1991 |
| 1751 HAWTHORNE STHUDSON BAYOU | $2,200,000 | 2026-07-15 | 4 / 3.5 | 3,875 | 2006 |
| 1702 WALDEMERE STHUDSON BAYOU | $1,150,000 | 2026-07-14 | 2 / 1 | 991 | 1950 |
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 July 20, 2026. All figures approximate and subject to change.
Condo Market by Era
West of Trail Active Condos by Construction Era
Active condominium, villa, townhouse inventory in West of Trail — 11 listings split across four construction eras. Newer towers carry a meaningful price premium; vintage mid-century buildings still dominate volume.
| Build Era | Active | Avg Price | Avg $/Sq Ft | Avg Living | Avg DOM |
|---|---|---|---|---|---|
| Pre-1990Built before 1990 | 11 | $372,991 | $314 | 1,136sq ft | 136days |
| 1990 – 2005Built 1990 through 2005 | — | — | — | — | — |
| 2006 – 2019Built 2006 through 2019 | — | — | — | — | — |
| 2020 & NewerBuilt 2020 or newer | — | — | — | — | — |
Scope: active condominium, villa, townhouse listings only. Single-family residences are excluded so the era-over-era price-per-square-foot comparison stays apples-to-apples. Data sourced from Stellar MLS via the Adamson Group data pipeline. Last updated July 20, 2026.
Typical Condo Dues
Monthly condo fees for active and recently sold West of Trail condominiums, villas and townhouses — from the lowest-fee associations to full-service luxury buildings.
Median Monthly Dues
$689/ mo
Minimum
$497/ mo
Maximum
$4,104/ mo
Source: Stellar MLS via the Adamson Group data pipeline. Monthly condo dues only; entries under $100/mo are treated as data-entry errors and omitted. Figures approximate and vary by building, square footage and amenities.
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 94 active listings and roughly 13 closed sales a month (trailing 12 months), West Of Trail Core has about 7.3 months of supply — a buyer's market (under 5 favors sellers, over 7 favors buyers).
What does a single-family home cost versus a condo on West Of Trail Core?
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Single-family homes sell around $1,850,000 ($682/sq ft), while condos, villas and townhouses sell around $322,500 ($320/sq ft).
What's the price range on West Of Trail Core?
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Active listings run from $98,000 to $26,400,000, with a median asking price of $3,247,500.
How quickly do homes sell on West Of Trail Core?
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Recently sold homes took a median 93 days on market and closed at 103.5% 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 26 active waterfront listings, 18 include a private dock; bay- and canal-front homes with a dock and lift command a clear premium over those without.
What are typical HOA and condo fees on West Of Trail Core?
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The median monthly condo fee is $689 and the median monthly association fee is $32.
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, and Oyster Bay — Sarasota's most established residential corridor for legacy single-family luxury homes.
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