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Overview

3 bd3 ba2,134 sqft2 car garageSingle Family
TypeSingle Family
HOA$656.62/qtr
Built1986
Lot15,778 sqft
Living area2,134 sqft
Price / sqft$491
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Ceiling Fans(s)Eat-in KitchenOpen FloorplanPrimary Bedroom Main FloorVaulted Ceiling(s)Hurricane ShuttersLightingOutdoor Shower

102 Windward Dr is a 1986-built home in Southbay Yacht & Racquet Club, Osprey. Inside you'll find 3 bedrooms, 3 bathrooms, and 2,134 square feet of living space. Listed at $1,047,000 (about $491/sqft), 0 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $656.62 quarterly.

From the listing

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.

The essentials

Built
1986
Price / sqft
$491
On market
Today
Annual tax
$3,959
HOA
$656.62/qtr
Flood zone
X · Low risk
Lot
15,778 sqft
Type
Single Family Residence

At a glance

Single family
Built 1986
Private pool
In Ground
2 car garage
0.36 acres
Lot size
2,134 sqft
Living area

Payment

Est. monthly payment
$6,533/mo
Down payment (20%)
$209,400
Property taxes
$330/mo
HOA
$656.62/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1986
Lot
15,778 sqft
Cooling
Central Air
Heating
Central
Parking
-
Pool
In Ground
Days on Market
0
Ceiling Fans(s)
Eat-in Kitchen
Open Floorplan
Primary Bedroom Main Floor
Vaulted Ceiling(s)
Hurricane Shutters
Lighting
Outdoor Shower
Private Mailbox
Clubhouse
Deed Restrictions
Fitness Center
Golf Carts OK
Park
Playground
Pool
Sidewalks
Tennis Court(s)
Dishwasher
Dryer
Microwave
Range
Range Hood
Refrigerator
Washer
Elementary
Laurel Nokomis Elementary
Middle
Laurel Nokomis Middle
High
Venice Senior High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2025)
$3,959
Parcel #
0157080006

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Southbay Yacht & Racquet Club
County
Sarasota
MLS Area
34229 - Osprey
Lot Size
15,778 sqft
HOA
$656.62/qtr
Southbay Yacht & Racquet Club / Rachelle Freed

Price history

Date
Event
Price
10/10/2026
Listed for sale
Source: Stellar MLS #TB8556740
$1,047,000
$491/sqft

Neighborhood

102 Windward Dr
Osprey, FL, 34229 · 34229 - Osprey

Market insights

Offer Insights

Choose an offer strength

List price: $1,047,000
$1.00M – $1.05M
95.2% – 100% of listTops out right at the list price
80% of listList price
35 of the last 66 home closings in 34229 landed at this number or higher (53%). The median one sat 35 days before it went under contract, and this one just listed today.

Sample: 66 closed home sales in 34229 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$6,533/mo
Principal & interest$5,461
Property taxes$330
Insurance$524
HOA$219
Down payment20% · $209,400
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA is the fee reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$1,047,000

$491 per sq ft

Beds and baths

3 beds, 3 baths

Size

2,134 sq ft

Time on market

Listed today

Year built

1986

Monthly payment

About $6,533/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $3,959 annual tax bill, insurance, and the $656.62/qtr HOA fee.

HOA fee

$656.62/qtr

Managed by Southbay Yacht & Racquet Club / Rachelle Freed.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byFUTURE HOME REALTY INCListing agent: Adam LeinwandListing data from Stellar MLS, MLS# TB8556740.

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