2302 Barbados Drive

Off Market

2302 Barbados Drive

Winter Park FL 32792

1544 sq. ft.

4024 sq. ft.

Townhouse

Last sold for $265,000

George FreeLove, last sold this property on 12 November 2026 after 61 days on market.

Overview

Welcome to Windward Square, a desirable Winter Park community conveniently located near shopping, dining, entertainment and major roadways. This spacious end-unit home offers 2 bedrooms, 2 full bathrooms with 1,544 square feet of living space. The home adds fabulous sun room with French doors to a private rear space. Originally designed as a 3-bedroom home, the third bedroom has been converted into a versatile flex room—ideal for a home office, den, hobby room or additional living space. The primary suite features a spacious walk-in closet with custom built-ins. Recent updates include a new roof in 2023, new flooring, fresh interior paint and more. As an end unit, the home provides additional privacy and a more open feel than interior units. The enclosed sunroom offers additional space for relaxing, entertaining or enjoying your morning coffee. Windward Square residents enjoy community amenities including a swimming pool and tennis courts. The convenient location provides easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this move-in-ready home offers space, flexibility and an excellent Winter Park location.

Features

2 bedrooms

2 bathrooms

1544 sq. ft. floor area

4024 sq. ft. lot size

Townhouse

Estimated Value

Based on this property and similar 2 bedroom townhouses sold in Winter Park over the last 12 months, the estimated median property value of 2302 Barbados Drive is $233k.

Median value

$233k

Estimated value range

$162k - $340k

Median days on market

Estimated value trend

-12%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Winter Park. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 2302 Barbados Drive

2026

Sold

$265,000

12 Nov 2026 by George FreeLove, of KELLER WILLIAMS AT THE PARKS

Happy sellers in Winter Park

90%

90% of sellers in Winter Park reported that their sale price either exceeded or met their price expectations.

Winter Park stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 6 reviews in Winter Park over the last 12 months.

Local market activity for 2 bedroom townhouses in Winter Park

In the last 12 months, 20 two-bedroom townhouses similar to 2302 Barbados Drive, have been sold.

This represents a 5% increase in two-bedroom townhouses sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Winter Park for a market analysis.

Abby Greenberg

at Compass Florida

4.9

(44 reviews)

Get a market analysis

Jorge Martinez, Jr

at KELLER WILLIAMS CLASSIC

(88 reviews)

Get a market analysis

Lisa Gould

at KELLER WILLIAMS WINTER PARK

(208 reviews)

Get a market analysis

Allison Day

at REMAX Town & Country Realty | Winter Springs

(109 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winter Park

Abby Greenberg

Sellers who recommend Abby Greenberg have praised them for being local expert, supportive, clear communication, responsive, trustworthy, great negotiation, and reliable

4.9 (44 reviews)
2 Reviews in Winter Park
2 Sales in Winter Park

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Jorge Martinez, Jr

Sellers who recommend Jorge Martinez, Jr have praised them for being clear communication, local expert, supportive, friendly, hard-working, well-prepared, and responsive

5 (88 reviews)
2 Reviews in Winter Park
1 Sale in Winter Park

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Lisa Gould

Sellers who recommend Lisa Gould have praised them for being local expert, clear communication, supportive, responsive, patient, reliable, and empathetic

5 (208 reviews)
1 Review in Winter Park
7 Sales in Winter Park

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Allison Day

Sellers who recommend Allison Day have praised them for being local expert, responsive, clear communication, supportive, patient, friendly, and empathetic