Active$3,295,000
135 TINA ISLAND DRIVE
OSPREY, FL 34229
3 beds5 baths2,572 sqft
1 / 96
Active · Single Family
14401 MASTHEAD DRIVE
OSPREY, FL 34229
Beds
3 beds
Baths
4 baths
Area
2,665 sqft
Single FamilyBuilt 201719,235 sqft lot2-car garageElectricCentral AirPoolFireplace$1069/sqft166 days on market
About this home
Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.
Facts & features
Interior
- Bedrooms
- 3
- Bathrooms
- 4
- Living area
- 2,665 sqft
- Heating
- Electric
- Cooling
- Central Air
- Flooring
- Marble, Tile
- Fireplace
- Yes
- Stories
- 1
- Features
- Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan…
- Appliances
- Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Dryer…
Exterior & lot
- Lot size
- 19,235 sqft (0.44 ac)
- Pool
- Yes
- Waterfront
- Yes
- Roof
- Metal
- Construction
- Block, Stucco
- Exterior
- French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk…
Parking
- Garage
- 2 spaces
Financial
- HOA dues
- $1,928 / quarterly
- Annual tax
- $874 (2025)
- Price / sqft
- $1069/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Property
- Property type
- Single Family
- Year built
- 2017
- Subdivision
- BAYSIDE
- County
- Sarasota
Assigned schools
- Elementary
- Laurel Nokomis Elementary
- Middle
- Sarasota Middle
- High
- Venice Senior High
Listing
- Status
- Active
- Days on market
- 139 days
- MLS #
- MFR783696465
- Source
- Stellar MLS
Listed by Mackenzie Longueuil · MICHAEL SAUNDERS & COMPANY
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Sample estimate — not an appraisal
$2.75M
−3.4% vs asking
$2.58M low$2.92M high
Based on 24 comparable sales within 4 miles of OSPREY, FL, this home is priced over RENA ValiQ.
Reference only. Estimates blend public sale comps, neighbourhood trend and the listing’s own metrics. Final price moves on diligence, terms and timing — RENA is your second read, not your agent.
Estimate your monthly cost
PITI + HOAEstimated monthly payment$15,127/mo
- Principal & interest
- $14,411/mo
- Property tax
- $73/mo
- Home insurance
- $0/mo
- HOA dues
- $643/mo
Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own bill; insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.
Ask about this property
Answered from this listing’s own figures and the sales around it.
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Aug 10, 2026 | Price reduced | $2,850,000 | −$400,000 |
| Mar 4, 2026 | Listed | $3,250,000 | — |
NeighbourhoodSample data
Reference scores for OSPREY, FL. Schools, mobility and amenities feed live data once the dedicated provider connection lands.
Walk Score
53/ 100
Somewhat walkable
Transit Score
68/ 100
Good transit
Bike Score
55/ 100
Bikeable
Elementary school
Laurel Nokomis Elementary
Assigned school from the MLS record
Middle school
Sarasota Middle
Assigned school from the MLS record
High school
Venice Senior High
Assigned school from the MLS record
Location
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