Front elevation14401 Masthead Drive, Osprey, FL 34229
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of September 26, 2026, 14401 Masthead Drive in Bayside, Osprey is listed at $2,850,000 (2,665 sq ft, about $1,069 per sq ft). That is 789% above Bayside's median closed sale of $320,750 over the last 12 months (308 recorded sales). Per square foot it is above the community's recent $226/sq ft by about 373%. It has been 157 days on market, longer than the community's typical 33 days to contract. Listing facts: built in 2017, a private pool, waterfront, HOA dues of $643/mo. The parcel maps to FEMA flood zone AE, a special flood hazard area where lenders generally require flood insurance. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
- No CDD assessment on record
- Built 2017 · 9 yrs
- 2,665 sq ft of living area
- 2-car garage
- 157 days on market
- HOA $643/mo (per listing)
Pricing & the SOUTH VENICE market
How this home is priced against recent nearby sales, and where SOUTH VENICE has been over 25 years. Momentum Research analysis of Stellar MLS records; closed sales, deemed reliable but not guaranteed. Estimates only; see data notes.
Price vs. size in SOUTH VENICE
Each dot is a closed sale since 2004 (4812 total). This home is the gold marker.
Sale price (y) by living area in sq ft (x). Stellar MLS closed sales.
Median $/sq ft by year
Community sold $/sq ft, 2012–2026. This home lists at $1069/sq ft.
Median sale price by year
12-month median closed price, 2012–2026.
Market Heat by year (0–100)
Momentum Market Heat, 2013–2026. Now 34 (cold).
This home’s history
- 2017BuiltPer public record
- Jul 10, 2026First trackedObserved at $2,995,000
- Aug 10, 2026Price cut$2,850,000
- NowActiveCurrently for sale
Build year is from public record. Listing milestones reflect movewithmomentum.com’s own observations since we began tracking this listing and are not the MLS listing history; dates and prices are deemed reliable but not guaranteed.
Estimated monthly payment
- Principal & interest $15,215/mo 79%
- Taxes $2,494/mo 13%
- Insurance $928/mo 5%
- HOA $643/mo 3%
$19,279/mo at 20% down, 30-yr @ 7.03% · edit any field to update.
Editable estimate — not a loan offer. Estimates only; see data & estimate notes.
Momentum Property Score
39/100 is limited across the objective indicators below. It reflects only those measures — not the home’s quality, condition, or desirability.
A 0-100 score built from objective property and market data: flood risk, insurance, pricing, supply, affordability, and recent sales. Higher means more measures line up in a buyer’s favor. It reflects only the factors below.
Momentum Scores are objective, rules-based indicators computed from listing facts, public records, and recent nearby sales. They are not appraisals, valuations, investment advice, or judgments about a neighborhood or who should live there. Verify independently.
The Momentum read
🟡 Asking $1069 per square foot, about 373% above the community’s $226 median. SOUTH VENICE’s 12-month median sold price per square foot is $226. Median sold price per square foot is down 2.8% year over year. Confidence: Very High · 308 closed sales in 12 monthsMLS facts: Stellar MLS closed sales. A per-square-foot gap is context, not an appraisal; condition, lot, and view set the final number here.
Recent SOUTH VENICE sales closed near 93.5% of original asking.Why it matters: the community’s own record shows how far opening prices typically move, and how often buyers compete without financing.Momentum Research analysis of Stellar MLS records, community-level, 12 months ending September 20, 2026. Aggregates only; deemed reliable but not guaranteed.
What’s unique here: one of only 2912 active listings in SOUTH VENICE, no CDD assessment.
Jump to: About this home · Every number, sourced · Monthly cost · Flood & risk · History · FAQ
Updated September 26, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
About this home
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.
Description provided by MICHAEL SAUNDERS & COMPANY and reproduced from the MLS; not independently verified.
Every fact, sourced
Listing data, public records, our calculations, and what to verify — each fact shown once. Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.
Listing facts MLS
Public records & third-party data
Calculated estimates
Buyer should verify Buyer verify
Provided via the Stellar MLS Internet Data Exchange, as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID. · deemed reliable but not guaranteedIDX 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 by the MLS to be accurate.The Messtimate
This is a deliberately dumb estimate — living area times a range of recent neighborhood $/sq ft, and nothing else. It is not an appraisal, not market value, and not a valuation of this home. Even a tight range from comparable sales can’t price a specific home — here’s why.
Actual list price: $2,850,000 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.
A 27% spread on the same house — and that gap is exactly what an automated guess can't see:
- Condition & updates — a renovated kitchen or new roof vs. dated finishes can swing value six figures; sq ft can't see it.
- The lot — this listing is waterfront; water frontage is priced far off a per-sq-ft average of the neighborhood.
- Outliers skew it — one flip or distressed sale in the comps drags the whole $/sq ft up or down.
- Carrying costs & concessions — this home carries HOA dues of $643/mo; with insurance and any seller-paid buydown, that changes what a buyer actually pays, and a sq ft estimate ignores all of it.
- The pool — a private pool carries cost and value that living area doesn't capture.
And here's what the live market is doing — which the number above ignores entirely:
- This home: 157 days on market vs. a 34-day community median
- 2962 active listings competing, 1014 under contract
For reference, this home is listed at $2,850,000 ($1,069/sq ft) — a number set with analysis a Messtimate can't do.
Selling your own home? Try the Messtimate on your address →
Methodology: 2,665 sq ft × $199–$253/sq ft from recent nearby closed sales (public records). Estimate for general information only; not an appraisal, valuation, or offer. Updated September 26, 2026.
Similar homes for sale near BAYSIDE
Active listings nearby at a comparable size and price. Listings held by brokerages other than Momentum Realty are marked with the listing broker. Deemed reliable but not guaranteed.
Newest listings in BAYSIDE
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- 4802 Kestral Park Circle #22 · $510,000 · 2 bd / 2.0 ba · listed September 25, 2026 (courtesy of COLDWELL BANKER REALTY)
- 7181 Westwood Way · $1,100,000 · 3 bd / 2.0 ba · listed September 25, 2026 (courtesy of FATHOM REALTY FL LLC)
- 614 Deerwood Avenue #614 · $189,000 · 2 bd / 2.0 ba · listed September 25, 2026 (courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE)
- 408 Gulf Of Mexico Drive #1206 · $65,000 · listed September 25, 2026 (courtesy of MICHAEL SAUNDERS & COMPANY)
- 408 Gulf Of Mexico Drive #2207 · $49,000 · listed September 25, 2026 (courtesy of MICHAEL SAUNDERS & COMPANY)
Recently off market in BAYSIDE
- Tbd Rainbow Road · last listed $439,900 · 2026-09-25
- Tbd Palmetto Drive · last listed $399,900 · 2026-09-25
- Tbd Mohawk Road · last listed $439,900 · 2026-09-25
- 5948 Orchis Road · last listed $409,000 · 2026-09-21
- 361 Falkland Road · last listed $309,900 · 2026-09-21
- 127 Columbia Road · last listed $235,000 · 2026-09-21
Price & listing history
Building permits
Flood zone & elevation
Sourced environmental data for the parcel. Confirm with FEMA and your insurer.
From the FEMA flood map. Lender-required flood insurance may apply; confirm for the parcel.
Approximate parcel elevation from USGS; confirm exact elevation with a survey.
This is a coastal Florida county. Premiums and coverage vary by home; obtain a quote from a licensed insurer.
Internet & broadband
AT&T Fiber covers much of NE Florida; confirm availability at the address.
Xfinity/Spectrum cable broadband is widely available.
T-Mobile / Verizon fixed-wireless as a backup option.
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Listed by MICHAEL SAUNDERS & COMPANY · MLS # A4684834
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Recent sales activity in BAYSIDE
Recent comparable closed sales near this home, from public records. Summary figures are for general reference only and are not a valuation of this property. See the BAYSIDE neighborhood guide for more.
Recent nearby closings in the data set.
Canonical 12-month median closed price. Reference only.
Canonical 12-month median $/sq ft. Reference only.
Go deeper on BAYSIDE
See schools, amenities, builders, HOA/CDD detail, and every active & sold home in the community — the single biggest advantage of buying here over a portal.
Assigned schools
Schools currently assigned to this address in Sarasota County, provided as neutral factual data. Assignments can change — confirm current zoning with the school district. This is not a statement about the home's suitability for any person or family.
Assigned schools per the MLS listing — assignments can change; confirm current zoning with the district. Browse school-zone pages →
Comparable recent sales
Recent closed sales nearby, with photos, so you can compare. Sold prices are public record, deemed reliable but not guaranteed.
No closely comparable recent sales were found in this data set.
Investment snapshot
Objective rental and cash-flow estimates for a buyer weighing this as an investment. Rough figures for general information only — not a guarantee of rent, an appraisal, or investment advice. Verify independently.
Buyer research checklist
Items worth confirming for 14401 Masthead Drive, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 2017: confirm the roof and HVAC install dates and whether any builder or manufacturer warranty transfers.
- HOA dues are listed at $643/mo: request the current budget, reserves, and rules before relying on that figure or on any restriction.
- FEMA flood zone AE: lenders generally require flood insurance here — get an elevation certificate and a flood quote before the inspection period ends.
- Get a homeowners insurance quote for this specific address in Sarasota County; a wind-mitigation inspection and, on older homes, a four-point inspection can change the premium.
- Private pool: confirm the barrier or alarm meets the state residential pool safety code and ask for pump, heater, and resurfacing records.
- Waterfront: confirm seawall or dock condition and permits, and ask who owns and maintains the shoreline.
- Listed living area is 2,665 sq ft: verify it against the property appraiser's record and measure before relying on it.
- Order a survey to confirm lot boundaries and easements.
- Review permit history with the county.
- Property taxes: the estimate on this page (about $29,925/yr) assumes reassessment at the list price; the seller's homestead cap does not transfer, so their current bill is not a guide.
- School zoning shown here comes from district data and changes; confirm the assigned schools directly with the district before relying on them.
Approximate distances
Approximate drive times for general reference only.
Data sources & freshness
| Listing record | Stellar MLS, refreshed twice daily (last: September 26, 2026) |
| Community market stats | Stellar MLS closed sales, as of September 20, 2026 |
| Flood zone & elevation | FEMA flood maps + USGS elevation (Zone AE shown above) |
| Taxes & monthly cost | Estimated from county rates; not a quote |
| Insurance figure | Modeled estimate; obtain a real quote before offering |
| Schools | 2025-26 district assignments; verify with the district |
Momentum Research lines are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Estimates are informational, not appraisals or advice. Methodology: how Momentum scores are computed.
Frequently asked questions
How big is 14401 Masthead Drive and when was it built?
Per the listing record, 14401 Masthead Drive was built in 2017 and has 2,665 sq ft of living area, 3 bedrooms and 3.5 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 14401 Masthead Drive in?
14401 Masthead Drive is in Bayside in Osprey, Sarasota County. The community section on this page shows recent closed sales, days on market, and active inventory for Bayside from the same MLS data.
Does 14401 Masthead Drive have an HOA, and how much are the dues?
The listing reports HOA dues of $643 per month. Dues, what they cover, and the community's rules should be confirmed from the association's current documents before relying on them.
Why might property taxes on 14401 Masthead Drive differ from the current owner's?
The estimate on this page (about $29,925 per year) assumes reassessment at the list price. Florida's Save Our Homes rule caps annual assessment increases for homesteaded owners, and the assessment resets after a sale, so a new owner's bill may differ from the seller's. Any tax figure shown here is an estimate, not the actual bill — confirm with the county property appraiser and tax collector.
Is 14401 Masthead Drive in a flood zone?
The FEMA flood map places this parcel in Zone AE, a special flood hazard area where lenders generally require flood insurance on a mortgaged purchase. Confirm the parcel's status with FEMA and your insurer, and ask for an elevation certificate.
Can I rely on the figures on this page?
No. Estimated taxes, insurance, payments, and any market or comparable-sales summary are opinions and estimates for general information only and should not be relied upon. Verify all information independently before making any decision.
See 14401 MASTHEAD DRIVE in person
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Opinion & estimate — do not rely on this page. Any figure on this page that is not a verbatim fact from the listing or a public record — including estimated property taxes, insurance, CDD/HOA amounts, mortgage payments, comparable-sales summaries, and market statistics — is an opinion and estimate provided for general informational purposes only. These figures may be inaccurate or out of date, are not appraisals, valuations, or financial, legal, tax, or investment advice, and should not be relied upon. Do not make any purchase, offer, financing, or other decision based on this page. Independently verify everything — price, square footage, lot size, year built, taxes, CDD/HOA, flood status, school assignments, permits, and community rules — with the listing broker, the county, your lender, a licensed inspector, an insurer, and your own advisors before acting.
Estimate methodology. Tax estimates apply a typical county millage rate to the list price and will differ from the actual assessed bill. Cost and market figures are derived from available data and simple calculations, not a professional appraisal. We make no representation that any estimate reflects fair market value.
Equal Housing Opportunity. Content on this page is compiled from public records, MLS data, and automated sources and may contain errors or be out of date. It is general information only, not a representation about any specific property, community, builder, or association. Verify information independently before relying on it. Momentum Realty supports the Fair Housing Act and does not discriminate on the basis of race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity. Information about schools, distances, and amenities is provided as neutral factual data to help you research the property and is not a statement about who should or should not live here or the suitability of the home or neighborhood for any person or group. School data may change — confirm current assignments with the school district.
Found an error? If you are the owner, listing agent, or a party to this property and believe any information is inaccurate, email and we will review and correct or remove it promptly.
Automated content. Some summaries, distances, and estimates on this page are generated automatically from public and proprietary data sources and may contain errors or omissions. We strive for accuracy but cannot guarantee the completeness or accuracy of any information. Verify anything important independently.
No warranty; measurements & photos. No guarantee, warranty, or representation of any kind is made regarding the completeness or accuracy of any information, descriptions, or measurements on this page — including square-footage measurements and property condition — all of which should be independently verified through appropriate means, including in-person inspection and public records. Photographs may be virtually staged or digitally enhanced and may not reflect actual property conditions. Momentum Realty and its agents expressly disclaim any liability in connection with the information provided.
MLS / IDX. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Stellar MLS Internet Data Exchange, as distributed by MLS GRID. Real estate listings held by brokerage firms other than Momentum Realty are marked with the listing broker's name and include the name of the listing agent. Data provided is deemed reliable but is not guaranteed by the MLS to be accurate. The information being provided is 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. Source: Stellar MLS, as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. All rights reserved.
Listing data is deemed reliable but is not guaranteed and is subject to change or withdrawal without notice. Square footage and lot size are approximate. Real estate brokerage services provided by Momentum Realty, licensed in Florida and Georgia. © 2026 Move With Momentum LLC.