NOT LISTED FOR SALE

123 Windward Dr Osprey, FL 34229

Estimated Value: $790,285 - $829,000

3 Beds
2 Baths
1,894 Sq Ft
$428/Sq Ft Est. Value

About This Home

PRICE IMPROVEMENT! This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bathrooms have also been updated. Natural light fills the home through replaced windows and elegant French doors, all of which are provided with hurricane protection for peace of mind. Crown molding and plantation shutters on all windows add a refined touch throughout, and engineered wood flooring enhances the living room and bedrooms, while ceramic tile flooring is featured in the kitchen and cozy family room complete with a charming wood-burning fireplace. Additional highlights include: a spacious utility room with ample cabinet storage, a new roof and fresh exterior paint in 2024 and new A/C system, dishwasher and garbage disposal in 2025. Florida-friendly landscaping with an abundance of fruit trees and native vegetation surrounding the home are perfect for the gardening enthusiast. Southbay Yacht & Racquet is a golf cart community that offers an array of community features and exceptional lifestyle with a recently remodeled 10,000 sq. ft. clubhouse featuring a well equipped fitness center, adjacent swimming pool, and expansive patio. The community-owned marina with residents only boat slips offers direct access to the Intracoastal Waterway with no fixed bridges to hinder your journey to the Gulf. Enjoy a wide range of amenities, including: pickleball and tennis courts, bocce and shuffleboard court, scenic walking and biking paths throughout the community and playground. Ideal location conveniently nestled between downtown Sarasota and downtown Venice, this home is close to top-rated dining, shopping, and entertainment. You’re just a short drive from world-renowned Siesta Key and Nokomis Beach, the Legacy Trail, and the nationally ranked Pine View School. Don’t miss this opportunity to own a beautiful home in one of the Gulf Coast’s most desirable boating communities

Ownership History

Date Name Owned For Owner Type

Purchase Details

Closed on
Aug 12, 2011
Sold by
Prewitt Andrews Llc
Bought by
Amero Albert W and Amero Carol L
Current Estimated Value
$811,571

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$382,500
Outstanding Balance
$262,446
Interest Rate
4.53%
Mortgage Type
Reverse Mortgage Home Equity Conversion Mortgage
Estimated Equity
$549,125

Purchase Details

Closed on
Apr 22, 2011
Sold by
Holmes Patricia N
Bought by
Prewitt Andrews Llc

Purchase Details

Closed on
Oct 28, 2004
Sold by
Holmes Patricia N
Bought by
Holmes Patricia N
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
Collateral Analytics

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ICE

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First American

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Quantarium

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Average Value
Not Available
List Price
Sold Price
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Purchase History

Date Buyer Sale Price Title Company
Amero Albert W $260,000 Stewart Title Company
Prewitt Andrews Llc $200,000 Alliance Group Title Llc
Holmes Patricia N -- --
Source: Public Records

Mortgage History

Date Status Borrower Loan Amount
Open Amero Albert W $382,500
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
01/09/2026 01/09/26 Price Changed $820,000 -3.5% $433 / Sq Ft
09/24/2025 09/24/25 For Sale $850,000 -- $449 / Sq Ft

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $3,109 $278,568 -- --
2024 $2,996 $270,717 -- --
2023 $2,996 $262,832 $0 $0
2022 $2,936 $255,177 $0 $0
2021 $2,897 $247,745 $0 $0
2020 $2,901 $244,324 $0 $0
2019 $2,792 $238,831 $0 $0
2018 $2,717 $234,378 $0 $0
2017 $2,703 $229,557 $0 $0
2016 $2,693 $269,600 $116,500 $153,100
2015 $2,741 $260,600 $116,500 $144,100
2014 $2,729 $209,909 $0 $0
Source: Public Records

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