14401 MASTHEAD DRIVE, OSPREY, FL, 34229
Active141 days on marketListed Mar 5, 2026MLS #A4684834
About this home
14401 MASTHEAD DRIVE
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
The home at a glance
3
Bedrooms
3.5
Bathrooms
2,665
Sqft
0.44 ac
Lot size
2
Garage
2017
Year built
One
Levels
$1,124
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$18,160 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$18,160/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+126.5%
$/sqft vs Osprey actives
$1,124 vs $323
Days on market
141 vs 57 typical
Where $1,124/sqft sits among the 95 Osprey actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Sarabay Acres
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Osprey. See the full Osprey guide →
Sarabay Acres — neighborhood snapshot
Population
1,075
Median age
65
Median income
$54,735
Median home value
$363,400
Avg household
2
Households w/ children
14%
For the school run
Sarasota County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Osprey market
$710K → $530K
Osprey median sold, yr/yr
93.5%
Sale-to-list ratio (12 mo)
51 of 95
Osprey actives have cut their price
Median sold price, Osprey, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 482% above the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 14401 MASTHEAD DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Aug ’25$975,000
3904 WAYPOINT AVENUE · same community
3 bd · 3 ba · 2,344 sqft · $416/sqft · 161 DOM
Sold · Jan ’26$900,000
3957 WAYPOINT AVENUE · same community
3 bd · 3 ba · 2,328 sqft · $387/sqft · 35 DOM
Sold · Apr ’26$1,001,000
3936 WAYPOINT AVENUE · same community
3 bd · 3 ba · 2,323 sqft · $431/sqft · 3 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 14401 MASTHEAD DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 14401 MASTHEAD DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
14401 MASTHEAD DRIVE FAQs
What would the monthly payment be for 14401 MASTHEAD DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $18,160/mo — principal and interest, the actual property-tax bill, the $643/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 14401 MASTHEAD DRIVE?+
The association fee works out to $643 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 14401 MASTHEAD DRIVE?+
The most recent tax bill on record (2025) was $874. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 14401 MASTHEAD DRIVE?+
The listing reports pets: Breed Restrictions, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Osprey?+
At $2,995,000, this home is listed about 333% above the Osprey median of $692,000. The market section on this page shows how the area is trending.
Which schools are assigned to 14401 MASTHEAD DRIVE?+
Laurel Nokomis School (elementary), Venice Senior High School (high) — Sarasota County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$2,995,000 runs 482% above the OSPREY 34229 median — but at 2,665 sqft it's also 21% larger than the typical Osprey listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Know the monthly fee
The association fee is $643/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Time on market is leverage
141 days on market against a Osprey median of 57 — sellers in this position are usually ready to negotiate.
05Strong assigned schools
Laurel Nokomis School, Venice Senior High School — Laurel Nokomis School rates 4 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of MICHAEL SAUNDERS & COMPANY · MacKenzie Longueuil. MLS #A4684834.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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