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Single family home for sale at 102 Windward Dr, Osprey, FL 34229 | MLS# TB8556740 | Listing updated on 2026-10-10
Photo 1 of Single family home for sale at 102 Windward Dr, Osprey, FL 34229 | MLS# TB8556740 | Listing updated on 2026-10-10
Photo 2 of Single family home for sale at 102 Windward Dr, Osprey, FL 34229 | MLS# TB8556740 | Listing updated on 2026-10-10
Photo 3 of Single family home for sale at 102 Windward Dr, Osprey, FL 34229 | MLS# TB8556740 | Listing updated on 2026-10-10
Photo 4 of Single family home for sale at 102 Windward Dr, Osprey, FL 34229 | MLS# TB8556740 | Listing updated on 2026-10-10
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$1,047,000

Monthly Est:$5,211

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,134sqft

102 Windward Dr, Osprey, FL 34229

$5,211/moEst:

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  • Single Family Residence

  • Built in 1986

  • $219/mo HOA

  • 15,778 sqft lot

  • $491/sq.ft

Description

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.

  • Houzeo last checked: 4 minutes ago
  • Listing updated: October 10, 2026 at 8:47 pm
  • Listing Provided by: Adam Leinwand (941) 565-0311 | FUTURE HOME REALTY INC (813) 855-4982
  • Source: Stellar MLS-FL | MLS#: TB8556740 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    1

  • County

    Sarasota County

  • City

    Osprey

  • Neighborhood

    --

  • Year Built

    1986

  • HOA Fees

    $219/mo

  • Finished Area

    2,134 sqft

  • Lot Size

    15,778 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    TB8556740

  • MLS Status

    Active

  • Days on Market

    1

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Location

HOA Management

Southbay Yacht & Racquet Club / Rachelle Freed

HOA Fees

$656.62/ Quarterly

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

  • Kitchen

    Level: First

  • Laundry

    Level: First

  • Living Room

    Level: First

  • Primary Bedroom

    Level: First

  • Bedroom 2

    Level: First

  • Bedroom 3

    Level: First

  • Primary Bathroom

    Level: First

  • Bathroom 2

    Level: First

  • Bathroom 3

    Level: First

Interior

  • Sewer

    Public Sewer

  • Interior Features

    Ceiling Fans(s), Eat In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Vaulted Ceiling(s)

  • Cooling

    Central Air

  • Flooring

    Tile, Vinyl

  • Heating

    Central

  • Exterior Features

    Hurricane Shutters, Lighting, Outdoor Shower, Private Mailbox

  • Appliances

    Dishwasher, Dryer, Microwave, Range, Range Hood, Refrigerator, Washer

Construction

  • Year Built

    Year Built: 1986

  • Home type

    Single Family Residence

  • Roof

    Tile

  • Foundation Details

    Slab

  • Construction Materials

    Block

Utilities & Energy

  • Laundry Features

    Inside, Laundry Room

  • Water Source

    Public

  • Utilities

    Electricity Available, Water Available

  • Pool Features

    In Ground

Other Features

  • Subdivision Name

    Southbay Yacht & Racquet Club

  • Community Features

    Clubhouse, Deed Restrictions, Fitness Center, Golf Carts Ok, Park, Playground, Pool, Sidewalks, Tennis Court(s)

Price History

DateEventPrice

10/10/2026

Source: mls_logoStellar MLS-FL #MFRTB8556740

Listed for Sale

$1,047,000 +61.08%

$491/sqft

06/04/2026

Source: mls_logoStellar MLS-FL #MFRA4671793

Sold

$650,000 +15.04%

$305/sqft

06/04/2026

Source: mls_logoStellar MLS-FL #MFRA4671793

Price Decreased

$565,000 -13.08%

$265/sqft

05/08/2026

Source: mls_logoStellar MLS-FL #MFRA4671793

Pending

$650,000

$305/sqft

04/26/2026

Source: mls_logoStellar MLS-FL #MFRA4671793

Price Decreased

$650,000 -5.80%

$305/sqft

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Based on information from Stellar MLS® through Oct 11, 2026, 03:45AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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