49 OSPREY POINT DRIVE, OSPREY, FL, 34229
Active252 days on marketListed Nov 13, 2025MLS #A4671762
About this home
49 OSPREY POINT DRIVE
Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.
Facts & features
The home at a glance
4
Bedrooms
3.5
Bathrooms
3,953
Sqft
0.4 ac
Lot size
2
Garage
1989
Year built
One
Levels
$607
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.
$15,663 /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
$15,663/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
+37.8%
Days on market
252 vs 57 typical
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 Oaks
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Osprey. See the full Osprey guide →
Oaks — neighborhood snapshot
Population
1,061
Median age
63
Median income
$98,734
Median home value
$983,226
Avg household
2
Households w/ children
47%
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)
Median sold price, Osprey, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 373% above the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
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
Steeve Cadeau
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 49 OSPREY POINT DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 49 OSPREY POINT DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Steeve's phone and CRM.
Straight answers
49 OSPREY POINT DRIVE FAQs
What would the monthly payment be for 49 OSPREY POINT DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $15,663/mo — principal and interest, the actual property-tax bill, the $475/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 49 OSPREY POINT DRIVE?+
The association fee works out to $475 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 49 OSPREY POINT DRIVE?+
The most recent tax bill on record (2024) was $14,206. 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 49 OSPREY POINT DRIVE?+
The listing reports pets: 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 $2,399,000, this home is listed about 247% above the Osprey median of $692,000. The market section on this page shows how the area is trending.
Which schools are assigned to 49 OSPREY POINT 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
$2,399,000 runs 373% above the OSPREY 34229 median — but at 3,953 sqft it's also nearly twice the size of 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.
03Time on market is leverage
252 days on market against a Osprey median of 57 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Laurel Nokomis School, Venice Senior High School — Laurel Nokomis School rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $2,595,000, now $2,399,000 — a $196K cut. The full history is in the market section below.
Listing courtesy of MICHAEL SAUNDERS & COMPANY · Jonathan Abrams, PLLC. MLS #A4671762.
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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