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ActivePOOL HOMEWATERFRONTNO CDD
$2,995,000
$1,124/sqft8% reduced
HOA: $1,928/quTaxes: $874/yr92d on market

Bayside

14401 MASTHEAD DR, OSPREY, FL, 34229

View all homes for sale in Bayside
3 Beds|4 Baths|2,665 Sq Ft|Built 2017|2 Car Garage
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💡 Price recently reduced — this could be a great opportunity to negotiate.

Waterfront
Waterfront
Bay/harbor
Water Frontage
87 ft
Water Body
LITTLE SARASOTA BAY
Description
Dock W/electric
Golf Course
Feature
Golf Carts Ok
Community
Yes
C2C

Coast 2 Coast Home Realty

Licensed Florida Realtors

4.9· 214 reviews

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Buyer Insights

Here's what we know about this listing.

Why this home stands out

  • Price reduced 8% ($255,000 off original)
  • 92+ days on market — seller may be motivated
  • Updated 1 day ago

Buyer Insights are informational only — always verify with your agent.

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.

City
OSPREY
Subdivision
BAYSIDE
County
Sarasota
Zip Code
34229
Community
Bayside

School Report Card

Source: FL Dept. of Education

ABCDF
Elementary
Middle
High

Neighborhood

Map unavailable

Type
Single Family Residence
Living Area
2,665 sqft
Construction
Block, Stucco
Roof
Metal
Flooring
Marble, Tile
Pool
Yes
HOA
$1,928 / Quarterly
  • Built-in Features
  • Ceiling Fans(s)
  • Crown Molding
  • Eat-in Kitchen
  • High Ceilings
  • Open Floorplan
  • Primary Bedroom Main Floor
  • Split Bedroom
  • Thermostat
  • Tray Ceiling(s)
  • Vaulted Ceiling(s)
  • Walk-in Closet(s)
  • French Doors
  • Lighting
  • Outdoor Grill
  • Outdoor Kitchen
  • Outdoor Shower
  • Sidewalk
  • Sliding Doors
  • Bar Fridge
  • Built-in Oven
  • Convection Oven
  • Cooktop
  • Dishwasher
  • Dryer
  • Gas Water Heater
  • Microwave
  • Range Hood
  • Refrigerator
  • Tankless Water Heater
  • Washer
  • Water Softener
  • Wine Refrigerator
  • Inside
  • Laundry Room
  • Covered
  • Screened
  • Cul-de-sac
  • Flood Insurance Required
  • Paved
  • Cable Connected
  • Electricity Connected
  • Natural Gas Connected
  • Sewer Connected
  • Water Connected
  • Buyer Approval Required
  • Deed Restrictions
  • Golf Carts Ok
  • Sidewalks
  • Dock
  • Water Access
  • Gated
  • Common Area Taxes
  • Escrow Reserves Fund
  • Maintenance Grounds
  • Management
  • Private Road
Bedrooms
3
Bathrooms
4
Year Built
2017
Construction
Block, Stucco
Flooring
Marble, Tile
Roof
Metal
Garage Spaces
2
Cooling
Central Air
Heating
Electric
Waterfront
Yes
Pet Restrictions
Breed Restrictions, Yes
Lot Size
0.44 acres
Senior Community
No
Building Elevator
Pet Size
Extra Large (101+ Lbs.)
# of Pets
3
Max Pet Weight
101 lbs
Tax Year
2025
Annual Tax Amount
$874

Association Fees

  • HOA Fee

    Bayside Community Association, Inc.

    $1,928/ Quarterly

Down Payment20% — $599,000
Interest Rate6.50%
Loan Term
Est. Mortgage
$15,144
HOA Fee
$643
Est. Property Tax
$73
Est. Insurance
$998
Total Est. Monthly Cost$16,858

* Estimates are for illustration purposes only and do not constitute an offer of financial advice. Actual rates, payments, insurance, and taxes will vary based on credit, location, and other factors. Contact a licensed mortgage professional for a personalized quote. Homeowners insurance estimate based on Florida averages.

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