
143 OSPREY POINT DRIVE, OSPREY, FL, 34229
Active42 days on marketListed Jun 11, 2026MLS #A4694133
About this home
143 OSPREY POINT DRIVE
One of the last available homesites in The Oaks Bayside. Almost 1/2 acre, at 17,647-square-feet, this exceptional lot presents a rare opportunity to build a custom luxury residence in one of Sarasota's most established and prestigious gated communities. Located behind the 24-hour staffed gates of The Oaks Bayside, this desirable homesite is ready to be transformed into the home you've always envisioned. Bring your own builder and architect and create a residence tailored to your lifestyle, surrounded by majestic oak trees, winding streets, and distinctive estate homes. The Oaks Bayside is renowned for its peaceful Old Florida charm, mature landscaping, and prime location along Little Sarasota Bay. This sought-after neighborhood offers a unique blend of privacy, natural beauty, and convenience, just minutes from the beaches of Casey Key, downtown Sarasota, and the area's finest shopping, dining, and cultural attractions. Ownership includes membership in The Oaks Club, one of Florida's most respected private club communities, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, croquet, a state-of-the-art WellFit Center, Junior Olympic heated swimming pool, bocce, basketball, playground facilities, multiple dining venues, and a vibrant year-round social calendar. Club membership is required, and there is currently NO WAITING LIST for either Golf or Sports/Social membership.
Facts & features
The home at a glance
0.4 ac
Lot size
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.
$3,970 /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
$4,497/mo
Includes estimated PMI — it drops off once you reach 20% equity. 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.
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 15% above the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 143 OSPREY POINT DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Feb ’26$175,000
216 GLENWOOD AVENUE
2 bd · 1 ba · 732 sqft · $239/sqft · 51 DOM
Sold · May ’26$430,000
328 E BAY STREET
2 bd · 1 ba · 884 sqft · $486/sqft · 2 DOM
Sold · Jun ’26$300,000
222 GLENWOOD AVENUE
2 bd · 2 ba · 952 sqft · $315/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 143 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 143 OSPREY POINT 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
143 OSPREY POINT DRIVE FAQs
What would the monthly payment be for 143 OSPREY POINT DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $3,970/mo — principal and interest, estimated property taxes, the $492/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 143 OSPREY POINT DRIVE?+
The association fee works out to $492 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 143 OSPREY POINT DRIVE?+
The most recent tax bill on record (2025) was $0. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Osprey?+
At $575,000, this home is listed about 17% below the Osprey median of $692,000. The market section on this page shows how the area is trending.
Which schools are assigned to 143 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.
Keep looking
Similar homes nearby
Listing courtesy of COLDWELL BANKER REALTY · Steve Abbe. MLS #A4694133.
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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