586 OAK BAY DRIVE, OSPREY, FL, 34229
Active1 days on marketListed Aug 27, 2026MLS #A4703807
Come see it
Upcoming open house
Sun, Aug 30
1:00 PM – 4:00 PM
Hosted by Mary Jo Violett
About this home
586 OAK BAY DRIVE
Welcome to Bay Oaks Estates, where spacious living, thoughtful design, and an ideal Osprey location come together in this beautifully maintained three-bedroom, two-bath home. With an open great room floor plan, a den, a separate private office, and a rare three-car garage, this home offers space and flexibility. The heart of the home is the inviting great room, where an electric fireplace adds warmth and ambiance, and the open design makes everyday living and entertaining effortless. The adjoining custom designed kitchen features granite countertops, wood cabinetry, breakfast bar, and a wine bar, creating a natural gathering place for family and friends. The private primary suite is a comfortable retreat with a spacious bath featuring dual sinks and a large walk-in shower. Even the indoor laundry room has been thoughtfully designed with granite countertops, a utility sink, and additional pantry storage. Step onto the impressive 27' x 21' lanai, with half of the space covered for comfortable year-round enjoyment and an electric sunshade for added convenience. The open portion lets you soak up the Florida sunshine, while the fenced backyard offers privacy and plenty of room to relax, entertain, garden, or play with the pups. A three-car garage is the extra space that's so hard to find—perfect for vehicles, bikes, kayaks, golf equipment, or additional storage. A new roof in 2023, A/C replaced in 2021, and a private irrigation well are all welcome bonuses. The location makes it even more special. Marinas, beaches, waterfront dining, golf courses, the Legacy Trail, shopping, and all that Sarasota's coastal lifestyle have to offer are just minutes from your door.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
2,084
Sqft
0.25 ac
Lot size
3
Garage
2003
Year built
One
Levels
$311
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.
$4,262 /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
$4,262/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
+1.8%
$/sqft vs Osprey actives
$311 vs $317
Days on market
1 vs 107 typical
Where $311/sqft sits among the 79 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 Bay Oaks Estates
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Osprey. See the full Osprey guide →
Bay Oaks Estates — neighborhood snapshot
Population
461
Median age
66
Median income
$96,845
Median home value
$936,700
Avg household
2
Households w/ children
13%
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
$723K → $765K
Osprey median sold, yr/yr
93.8%
Sale-to-list ratio (12 mo)
42 of 79
Osprey actives have cut their price
Median sold price, Osprey, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 24% above the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 586 OAK BAY DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$685,000
597 OAK RIVER COURT · same community
4 bd · 2 ba · 2,111 sqft · $324/sqft · 103 DOM
Sold · Nov ’25$540,000
813 OAK POND DRIVE · same community
4 bd · 2 ba · 1,981 sqft · $273/sqft · 121 DOM
Sold · Nov ’25$625,000
594 PINE RANCH EAST ROAD · same community
3 bd · 2.5 ba · 2,298 sqft · $272/sqft · 51 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
Alek Cherrone
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 586 OAK BAY DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 586 OAK BAY DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Alek's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
586 OAK BAY DRIVE FAQs
What would the monthly payment be for 586 OAK BAY DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,262/mo — principal and interest, the actual property-tax bill, the $25/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 586 OAK BAY DRIVE?+
The association fee works out to $25 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 586 OAK BAY DRIVE?+
The most recent tax bill on record (2025) was $3,985. 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 586 OAK BAY 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 $649,000, this home is listed about 3% below the Osprey median of $669,500. The market section on this page shows how the area is trending.
Which schools are assigned to 586 OAK BAY 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
Four things that matter here
01Positioned at the premium end
$649,000 runs 24% above the OSPREY 34229 median.
02Trees/Woods views
The trees/woods view is part of what you're buying — views hold value independently of the structure.
03Fresh on the market
Only 1 day on market in a Osprey market that averages 107 — if it fits, move quickly.
04Strong 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 WHITE SANDS REALTY GROUP FL · Mary Jo Violett. MLS #A4703807.
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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