$2,850,000
 $15,299 est/mo Sourced by Back At You

14401 Masthead Dr,OSPREY, FL 34229

OSPREY, FL 34229

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Description

Under contract-accepting backup offers. 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.

Details

MLS #A4684834
Listing TypeFor Sale
StyleHouse
HOA Dues$1,928
Sub-TypeFor-sale
StatusActive Under Contract
Year2017
Days On Site196
Listing Provided ByMICHAEL SAUNDERS & COMPANY | Mackenzie Longueuil

Features

Bed(s)3
Bath(s) 4 Total
SQ Feet2,665
Garage2
PoolYes
Story(s)1
ZoningRSF1
Acreage0.44
Water FrontYes
Property ViewWater

Taxes

Property874

Area Information

StateFL
CountySarasota
CityOSPREY
Zip Code34229
Area34229 Osprey
SubareaBayside
Community NameBAYSIDE
School DistrictVenice Senior High
Elementary SchoolLaurel Nokomis Elementary
High SchoolVenice Senior High
Listing VS Median (in BAYSIDE)
Price:
$2,850,000
low | high
Med:
$1,799,950
86.843859649123% of Average
sqft:
2,665
low | high
Med:
2,694
48.91181988743% of Average
$ / sqft:
$1,069
low | high
Med:
$672
87.124085921745% of Average
On site:
196
low | high
Med:
98
100% of Average
Sourced by Back At You

Market Activity 34229

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 Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of September 17, 2026 at 3:52:17 PM PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

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Learn More About This Property

StateFL
CountySarasota
CityOSPREY
Zip Code34229
Area34229 Osprey
SubareaBayside
Community NameBAYSIDE
School DistrictVenice Senior High
Elementary SchoolLaurel Nokomis Elementary
High SchoolVenice Senior High
Listing VS Median (in BAYSIDE)
Price:
$2,850,000
low | high
Med:
$1,799,950
86.843859649123% of Average
sqft:
2,665
low | high
Med:
2,694
48.91181988743% of Average
$ / sqft:
$1,069
low | high
Med:
$672
87.124085921745% of Average
On site:
196
low | high
Med:
98
100% of Average
Sourced by Back At You
Nearby Listings (Within 1/10 mile)
Price: $2.137M - $3.562M
sqft: 1,500 - 3,000
Nearby Listings Property ImageNearby Listings Details
780 SARABAY RD #16 Property Photo 1
$425,000
780 Sarabay Rd #16
Osprey, FL 34229
Listing Updated: August 28, 2026 at 3:53:05 PM PDT
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