Area Guide
West of Trail - South
Waterfront mainland communities approaching Siesta
About West of Trail - South
The southern extension of West of Trail — covering the mainland luxury corridor from the south end of the core area down to Stickney Point Road, including Phillippi Estates, Bay Shore, Country Club Shores-adjacent mainland parcels, and the deep-water canal communities west of US-41 approaching Siesta Key. Waterfront-heavy with substantial single-family inventory.
Sold + Pending Activity
West of Trail - South Closed Market Snapshot
Averages across 257 sold and 19 pending listings in the West of Trail - South submarket. Pre-list and withdrawn activity excluded. Price range: $130,000 – $5,500,000.
| Metric | Value |
|---|---|
| Average Price | $633,213 |
| Average Price / Sq Ft | $330 |
| Average Year Built | 1980 |
| Average Living Area | 1,752 sq ft |
| Average Days on Market | 77 days |
Data sourced from Stellar MLS via the Adamson Group data pipeline. Last updated July 20, 2026.
Active Market Snapshot
West of Trail - South Active Inventory & Recent Sales
A live snapshot of the West of Trail - South luxury real estate market — built directly from the Sarasota MLS feed and refreshed regularly. Data through July 20, 2026.
Active Inventory
- Active Listings
- 105
- Median List Price
- $475,000
- Median Price / Sq Ft
- $333
- Waterfront Share
- 27%
Of 105 active listings, 28 are waterfront (27%) and 2 are new construction built in 2020 or later (2%).
Active Inventory by Price Band
| Price Band | Active Listings |
|---|---|
| Under $900k | 82 |
| $900k – $1.5M | 4 |
| $1.5M – $3M | 13 |
| $3M and above | 6 |
Recent Sold Activity (Last 90 Days)
- Sold Listings
- 63
- Median Sold Price
- $422,500
- Median Days on Market
- 39
- Sale-to-List Ratio
- 88.9%
Most Recent Sold Comparables (Last 90 Days)
| Address | Sold | Date | Bd / Ba | Sq Ft | Built |
|---|---|---|---|---|---|
| 1508 PELICAN COVE RD #GR232(waterfront)PELICAN COVE XIII | $287,500 | 2026-07-16 | 2 / 2 | 1,211 | 1980 |
| 4812 KESTRAL PARK CIR #20LANDINGS CARRIAGEHOUSE II | $285,000 | 2026-07-15 | 2 / 2 | 1,570 | 1982 |
| 8915 VAMO RDMEAD HELEN D | $405,000 | 2026-07-10 | 1 / 1 | 870 | 2017 |
| 1632 STICKNEY POINT RD #201CASTEL DEL MARE | $340,000 | 2026-07-10 | 2 / 2 | 1,016 | 1975 |
| 4939 PEREGRINE POINT WAYTHE LANDINGS | $1,450,000 | 2026-07-09 | 4 / 4.5 | 3,828 | 2000 |
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 - South 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 - South Active Condos by Construction Era
Active condominium, villa, townhouse inventory in West of Trail - South — 69 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 | 57 | $361,311 | $291 | 1,269sq ft | 143days |
| 1990 – 2005Built 1990 through 2005 | 7 | $597,286 | $297 | 2,012sq ft | 129days |
| 2006 – 2019Built 2006 through 2019 | 3 | $589,667 | $345 | 1,711sq ft | 125days |
| 2020 & NewerBuilt 2020 or newer | 2 | $629,000 | $353 | 1,785sq ft | 204days |
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 - South condominiums, villas and townhouses — from the lowest-fee associations to full-service luxury buildings.
Median Monthly Dues
$933/ mo
Minimum
$160/ mo
Maximum
$1,710/ 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 - South Market Questions & FAQ
Is West Of Trail South a buyer's or seller's market right now?
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With 105 active listings and roughly 18 closed sales a month (trailing 12 months), West Of Trail South has about 5.8 months of supply — a balanced market (under 5 favors sellers, over 7 favors buyers).
What does a single-family home cost versus a condo on West Of Trail South?
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Single-family homes sell around $518,750 ($321/sq ft), while condos, villas and townhouses sell around $347,500 ($253/sq ft).
What's the price range on West Of Trail South?
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Active listings run from $130,000 to $5,500,000, with a median asking price of $475,000.
How quickly do homes sell on West Of Trail South?
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Recently sold homes took a median 39 days on market and closed at 88.9% of original list price (trailing 90 days).
Can I keep a boat — how many West Of Trail South homes have a dock?
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Of 28 active waterfront listings, 16 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 South?
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The median monthly condo fee is $933 and the median monthly association fee is $842.
What is West of Trail South?
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West of Trail South covers the southern mainland luxury corridor from the south end of the West of Trail core area down to Stickney Point Road. The area includes Phillippi Estates, Bay Shore, and the deep-water canal communities approaching the Siesta Key bridges — a waterfront-heavy market with substantial single-family inventory.
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