296 PINE RANCH TRAIL, OSPREY, FL, 34229
Active26 days on marketListed Aug 28, 2026MLS #A4704317
About this home
296 PINE RANCH TRAIL
Welcome to this rare slice of coastal paradise tucked away in the boutique enclave of Pine Ranch East in Osprey, Florida. Situated on a sprawling 1.137-acre private lot, this magnificent residence offers an extraordinary blend of space, serenity, and convenience. The property boasts five spacious bedrooms and three-and-a-half baths, providing a flexible layout designed to accommodate large families, host overnight guests, or create dedicated home office spaces. Every detail of the interior reflects thoughtful maintenance and pride of ownership, offering a seamless flow between the primary living areas. Designed for quintessential Florida living, the expansive backyard functions as your own private resort. Step out onto the oversized covered lanai to entertain year-round, or cool off in the crystal-clear heated pool and integrated spa while taking in the tranquil scenery of your secluded acreage. Despite the incredible privacy, you are just minutes away from pristine Gulf beaches and iconic local dining hot spots like Pops Sunset Grill and the Casey Key Fish House. Adding to the unmatched value of this property is its setting within Pine Ranch East, an exclusive neighborhood comprised of only 26 homes. While the community maintains an established HOA structure, homeowners enjoy the astonishing benefit of paying no HOA fees thanks to a unique financial setup that leaves the neighborhood fully funded years into the future. Contact us today to learn more about this remarkable community story or to schedule your private tour.
Facts & features
The home at a glance
5
Bedrooms
3.5
Bathrooms
3,354
Sqft
1.14 ac
Lot size
2
Garage
1995
Year built
One
Levels
$328
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 — not generic estimates.
$7,355 /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
$7,355/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
+15.2%
$/sqft vs Osprey actives
$328 vs $368
Days on market
26 vs 107 typical
Where $328/sqft sits among the 77 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)
32 of 77
Osprey actives have cut their price
Median sold price, Osprey, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 83% above the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 296 PINE RANCH TRAIL
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$1,014,000
201 EAGLENOOK WAY
4 bd · 3 ba · 3,379 sqft · $300/sqft · 203 DOM
Sold · Mar ’26$700,000
851 PLACID LAKE DRIVE
5 bd · 4 ba · 3,395 sqft · $206/sqft · 37 DOM
Sold · Nov ’25$910,000
766 SHADOW BAY WAY
4 bd · 3 ba · 3,438 sqft · $265/sqft · 132 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
Gianfranco Di Flumeri
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 296 PINE RANCH TRAIL — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 296 PINE RANCH TRAIL — before you fall in love.
See it in person
Schedule a tour
Live availability from Gianfranco's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
296 PINE RANCH TRAIL FAQs
What would the monthly payment be for 296 PINE RANCH TRAIL?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $7,355/mo — principal and interest, the actual property-tax bill 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.
What are the property taxes on 296 PINE RANCH TRAIL?+
The most recent tax bill on record (2025) was $10,159. 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 296 PINE RANCH TRAIL?+
The listing reports pets: Cats OK, Dogs OK. 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 $1,100,000, this home is listed about 64% above the Osprey median of $669,500. The market section on this page shows how the area is trending.
Which schools are assigned to 296 PINE RANCH TRAIL?+
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
01Positioned at the premium end
$1,100,000 runs 83% above the OSPREY 34229 median — but at 3,354 sqft it's also 53% larger than the typical Osprey listing.
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 BEYOND REALTY LLC · Darren Dowling. MLS #A4704317.
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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