Florida
Osprey
38 W BAY STREET

$925,000

38 W BAY STREET, Osprey, FL 34229

3 beds |
2 baths |
2,124 sqft

Single-Family Home
Built in 1994
9,583sqft lot
—— car garage
$435/sqft
Listed 2 days ago

Property Description

Live like you’re on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam metal roof, hurricane impact windows, electric tankless water heater, wraparound "Lifeproof" composite decking, and a custom heated pool. Interior features vaulted ceilings with a mix of travertine, LVP, and tile flooring, plus a kitchen with solid wood cabinets, stainless steel appliances, beadboard ceiling, and custom backsplash. The screened second-story porch has an electronic roll-up system for open-air or enclosed comfort. A unique “hidden” door design allows the home to function as one residence or two separate units, with the lower level offering its own entrance, bedroom, bath, family room, and laundry—perfect for in-laws, guests, or rental income. Outdoors, enjoy lush landscaping, a tropical pool setting, and unbeatable location just a block from the public dock and kayak launch. Minutes to Sarasota, Venice Island, beaches, Legacy Trail, and Spanish Pointe.

Listing Status:: Active
Date Added:: October 1, 2025 at 05:00AM
Listing Office:: HARRY ROBBINS ASSOC INC : 941-924-8346
Listing Agent:: Mitchell Helmuth : 941-302-4212
MLS ID:: A4667010

General: Ceiling Fan(s)Kitchen/Family Room ComboPrimary Bedroom Main FloorSolid Wood CabinetsStone CountersThermostatWalk-In Closet(s)
Appliances: DishwasherDisposalElectric Water HeaterMicrowaveRange HoodRefrigeratorWasher
Laundry: Inside
Flooring: Ceramic TileLaminateTravertine
A/C: Central Air
Heating: CentralElectric
Eco/Green Feature: Windows

General: Rain Gutters
Style: FloridaKey West
Pool: GuniteHeatedIn Ground
Parking: Garage Door Opener

Roofing: Metal
General: BlockConcreteVinyl SidingWood FrameTwoSlab

Road/Access: Paved
Originating MLS: Stellar MLS
County: Sarasota

Zoning: RSF3W 1/2 OF LOT 1 BLK 2 V A SAUNDERS RESUB OF WEBBS ADD TO VILLAGE OF OSPREY0143140020
Fencing: FencedWood

Utilities: Cable ConnectedElectricity ConnectedPhone AvailablePublic
Water: Public
Sewer: Septic Tank

Source: Stellar MLS

This listing courtesy of Mitchell Helmuth, HARRY ROBBINS ASSOC INC

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Pine View School

1 Python Path, Osprey, FL, 34229

Grades 2-12

1.01 miles away

Pine View School

1 Python Path, Osprey, FL, 34229

Grades 2-12

1.01 miles away

Pine View School

1 Python Path, Osprey, FL, 34229

Grades 2-12

1.01 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.