534 OAK BAY DRIVE, OSPREY, FL, 34229
Active16 days on marketListed Jul 8, 2026MLS #A4699469
About this home
534 OAK BAY DRIVE
AVAILABLE AUGUST 25, 2026 AS UNFURNISHED RENTAL. Very nice light and bright 4 bedroom pool home with private secluded lot in the quaint community of Oak Bay Estates in Osprey. Great access to Sarasota and Venice without having to get on I-75. New interior paint and new ceiling fans throughout. Enjoy this great home and the private pool in your spare time as the pool care and lawn and landscaping are done for you and included in the rent. This home is located in a very nice neighborhood with easy access to many restaurants, shopping and the Florida lifestyle including the Legacy Trail for biking, walking or jogging. Only 10 minutes to two of the finest beaches on the Gulf Coast at Siesta key and Nokomis beach. First and last months rent and security deposit due upfront. pets are possible and are considered on a case by case basis.
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
2,077
Sqft
0.23 ac
Lot size
2
Garage
1996
Year built
One
Levels
$2
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$188 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
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
Estimated payment
$188/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; 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.
$/sqft vs Osprey actives
$2 vs $331
Days on market
16 vs 57 typical
Where $2/sqft sits among the 96 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
$710K → $530K
Osprey median sold, yr/yr
93.5%
Sale-to-list ratio (12 mo)
52 of 96
Osprey actives have cut their price
Median sold price, Osprey, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 99% below the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 534 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 · Jun ’26$483,500
5667 WOODLAND SAGE DRIVE
4 bd · 2.5 ba · 2,045 sqft · $236/sqft · 14 DOM
Sold · Jan ’26$510,000
12689 PROMENADE ESTATES BOULEVARD
4 bd · 2.5 ba · 2,045 sqft · $249/sqft · 38 DOM
Sold · Dec ’25$500,000
12665 PROMENADE ESTATES BOULEVARD
4 bd · 2.5 ba · 2,045 sqft · $244/sqft · 452 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
Eric Chery
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 534 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 534 OAK BAY DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Eric's phone and CRM.
Straight answers
534 OAK BAY DRIVE FAQs
What would the monthly payment be for 534 OAK BAY DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $188/mo — principal and interest, estimated property taxes 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.
Are pets allowed at 534 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 $3,800, this home is listed about 99% below the Osprey median of $692,000. The market section on this page shows how the area is trending.
Which schools are assigned to 534 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
Three things that matter here
01Under the OSPREY 34229 market on paper
$3,800 is 99% below the OSPREY 34229 median of $515,000, and at $2/sqft it sits under the Osprey average of $401.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Strong 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 REALTY BY DESIGN LLC · Brian ODonnell. MLS #A4699469.
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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