1355 SOUTHBAY DRIVE, OSPREY, FL, 34229
Active198 days on marketListed Jan 15, 2026MLS #A4677804
About this home
1355 SOUTHBAY DRIVE
Southbay Yacht & Racquet Club where the true Florida lifestyle is alive and well! This three-bedroom two bath pool home is located in an active community with unmatched amenities such as an active social atmosphere, heated community pool, playground, fitness room, tennis, pickleball courts, and fishing. All for you to enjoy! Walk, bike or take your golf cart to restaurants, shopping or the private community waterfront park! Come live the ultimate Florida lifestyle. You're not just leasing a home you're being invited into one of the most sought-after communities in southwest Florida!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
2,367
Sqft
0.29 ac
Lot size
2
Garage
1978
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.
$193 /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
$193/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 SOUTHBAY YACHT & RACQUET CLUB
$2 vs $680
Days on market
198 vs 57 typical
Where $2/sqft sits among the 6 homes for sale in SOUTHBAY YACHT & RACQUET CLUB
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 Southbay Yacht & Racquet Club
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Osprey. See the full Osprey guide →
Southbay Yacht & Racquet Club — neighborhood snapshot
Population
1,031
Median age
64
Median income
$98,565
Median home value
$807,000
Avg household
2
Households w/ children
44%
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)
5 of 6
SOUTHBAY YACHT & RACQUET CLUB 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 1355 SOUTHBAY DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’26$565,000
186 WINDWARD DRIVE · same community
3 bd · 2 ba · 2,505 sqft · $226/sqft · 116 DOM
Sold · Jun ’26$565,000
102 WINDWARD DRIVE · same community
3 bd · 2.5 ba · 2,134 sqft · $265/sqft · 169 DOM
Sold · May ’26$1,075,000
432 YACHT HARBOR DRIVE · same community
3 bd · 2.5 ba · 2,125 sqft · $506/sqft · 0 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 1355 SOUTHBAY DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1355 SOUTHBAY 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
1355 SOUTHBAY DRIVE FAQs
What would the monthly payment be for 1355 SOUTHBAY DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $193/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 1355 SOUTHBAY DRIVE?+
The listing reports pets: Breed Restrictions, 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 $4,500, 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 1355 SOUTHBAY 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
01Under the OSPREY 34229 market on paper
$4,500 is 99% below the OSPREY 34229 median of $499,450, 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.
03Time on market is leverage
198 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.
Keep looking
Similar homes nearby
Listing courtesy of GOLF & BAY PROPERTIES LLC · Sharon Lewis. MLS #A4677804.
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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