102 WINDWARD DRIVE, OSPREY, FL, 34229
Active2 days on marketListed Oct 10, 2026MLS #TB8556740
About this home
102 WINDWARD DRIVE
Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival. Inside, new vinyl flooring flows through the living spaces and bedrooms, complemented by large format tile in the bathrooms. High ceilings and a decorative beam add character to the open living area. The redesigned kitchen features new cabinetry, quartz countertops with a waterfall detail, stainless steel appliances, a range hood, pendant lighting, illuminated shelving and a walk in pantry. The home offers three bedrooms, two full bathrooms and one half bathroom. The primary retreat offers two newly built closets and a beautifully remodeled bathroom with a spacious double vanity, freestanding soaking tub, separate shower, new fixtures and mirrors. The remodeled guest bathroom features a large double vanity, coordinating tile and updated shower fixtures. The layout features dual primary bedrooms, with the second offering a generous walk in closet, an attached half bathroom and exterior access. Practical updates complement the refreshed interiors, with hurricane rated windows throughout the home and hurricane shutters for added storm protection. New ceiling fans in the bedrooms, an interior laundry room with a new washer and dryer combo, and an oversized garage with an epoxy painted finish add everyday convenience. Step outside to the screened pool and covered lanai, with a new outdoor shower for rinsing off after a swim. An expanded paver area beyond the lanai with a built in outdoor fireplace offers another inviting space to relax and entertain. Enjoy Southbay Yacht and Racquet Club’s waterfront lifestyle, featuring a community marina with Intracoastal access, a community pool, tennis, pickleball, a fitness center and clubhouse. From time on the water to relaxing evenings by your own pool, this home brings together beautifully updated spaces and an active coastal lifestyle. No CDD.
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
2,134
Sqft
0.36 ac
Lot size
2
Garage
1986
Year built
One
Levels
$491
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.
$6,751 /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
$6,751/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
+42.4%
$/sqft vs SOUTHBAY YACHT & RACQUET CLUB
$491 vs $701
Days on market
2 vs 109 typical
Where $491/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
$723K → $765K
Osprey median sold, yr/yr
93.8%
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 66% above the OSPREY 34229 median. See the full Osprey market guide →
Paper trail
This home's history
Reality check
What actually sold near 102 WINDWARD 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$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
Sold · Jun ’26$817,000
1486 LANDVIEW LANE · same community
3 bd · 2 ba · 1,869 sqft · $437/sqft · 158 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
Kevin Johnson
CEO & Managing Broker · CENTURY 21 Edge
Tours, negotiation, and every question about 102 WINDWARD DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 102 WINDWARD DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Kevin's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
102 WINDWARD DRIVE FAQs
What would the monthly payment be for 102 WINDWARD DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,751/mo — principal and interest, the actual property-tax bill, the $219/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 102 WINDWARD DRIVE?+
The association fee works out to $219 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 102 WINDWARD DRIVE?+
The most recent tax bill on record (2025) was $3,959. 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 102 WINDWARD DRIVE?+
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 $1,047,000, this home is listed about 50% above the Osprey median of $700,000. The market section on this page shows how the area is trending.
Which schools are assigned to 102 WINDWARD 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
$1,047,000 runs 66% above the OSPREY 34229 median.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Fresh on the market
Only 2 days on market in a Osprey market that averages 109 — 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 FUTURE HOME REALTY INC · Adam Leinwand. MLS #TB8556740.
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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