Oakland Park, Winter Garden, FL, Real Estate

Oakland Park is a charming residential community nestled in the heart of Winter Garden, FL. Located just minutes from downtown Winter Garden, this community offers a peaceful retreat from the hustle and bustle of city life while still providing easy access to all the amenities of a major metropolitan area.

The homes in Oakland Park are beautifully designed and built with high-quality materials, featuring a variety of architectural styles that add character and charm to the neighborhood. The community is well-manicured, with lush green lawns, mature trees, and colorful flowers adding to its natural beauty.

Oakland Park offers a range of amenities for residents to enjoy, including a large community pool, fitness center, playground, and sports fields. The community also features scenic walking trails and plenty of open green space, perfect for picnics, outdoor games, and relaxation.

One of the unique features of Oakland Park is its location next to the West Orange Trail, a popular multi-use trail that spans 22 miles and connects Winter Garden to other nearby communities. This trail is perfect for jogging, biking, or leisurely strolls, and provides easy access to local shops, restaurants, and other attractions.

Overall, Oakland Park is a wonderful place to call home for anyone looking for a peaceful, family-friendly community with plenty of amenities and easy access to all that Winter Garden has to offer.

Oakland Park currently has 7 single family homes for sale with an average list price of $1,230,261.43. The average annual property tax for Oakland Park is $8,402.20.

Current Homes for Sale

Schools

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What's Hot & What Not

Absorption Report Using the absorption rate, we can determine how long it's taking for homes to sell and which price points are selling the fastest in Oakland Park, i.e. what's hot and what's not.

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Recent Sales

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Subdivisions

Subdivisions Median Price
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Oakland Park

Oakland Park is a single-family home community in Winter Garden, Florida, built between 2008 and 2025 by David Weekley Homes, Dream Finders Homes, and href="/builders/fl/rockwell-homes">RockWell Homes. It currently has 6 single family homes for sale with an average list price of $1,223,971.67. The homes range in size from 1,632 ft2 to 5,754 ft2. The HOA fees range from $125 to $729 per month. The average annual property tax for Oakland Park is $6,807.31. It is located in Orange County. ... Read more
Median Price: $912,500

Subdivisions

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Market Trends

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Real Estate News

New Homes For Sale This Week in Oakland Park: April 10th to April 16th

New Homes For Sale This Week in Oakland Park: April 10th to April 16th - April 17, 2026

Oakland Park had only 1 new home for sale during the week of Friday, April 10 to Thursday, April 16, including and it was a single family home for sale ... continue reading
Homes Just Sold in Oakland Park: March 31st to April 6th

Homes Just Sold in Oakland Park: March 31st to April 6th - April 7, 2026

Oakland Park had only 1 sale during the week of Tuesday, March 31 to Monday, April 6, including and it was a single family home for sale with a list ... continue reading
Homes Just Sold in Oakland Park: March 24th to March 30th

Homes Just Sold in Oakland Park: March 24th to March 30th - March 31, 2026

Oakland Park had only 1 sale during the week of Tuesday, March 24 to Monday, March 30, including and it was a single family home for sale with a list ... continue reading
Homes Just Sold in Oakland Park: March 17th to March 23rd

Homes Just Sold in Oakland Park: March 17th to March 23rd - March 24, 2026

Oakland Park had only 1 sale during the week of Tuesday, March 17 to Monday, March 23, including and it was a single family home for sale with a list ... continue reading
Homes Just Sold in Oakland Park: March 10th to March 16th

Homes Just Sold in Oakland Park: March 10th to March 16th - March 17, 2026

Oakland Park had only 1 sale during the week of Tuesday, March 10 to Monday, March 16, including and it was a single family home for sale with a list ... continue reading
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