The Oaks, Kissimmee, FL, Real Estate

The Oaks Golf Club and Community boasts an impressive array of amenities that blend premier golfing with resort-style living for residents and visitors alike. Central to the experience is the 18-hole championship golf course, designed by Karl Litten, which winds through majestic 100-year-old oaks, sloping fairways, pristine water features, and abundant wildlife including wild turkeys, herons, eagles, and hawks. Golf enthusiasts can refine their skills at the expansive practice facility equipped with 20 range stations, a dedicated chipping area, and putting green, while the clubhouse offers The Oaks Café for casual dining and beverages, complete with flat-screen TVs, a covered outdoor patio, and a fully stocked pro shop for apparel and accessories. Beyond the greens, the gated community provides family-friendly features such as a boat ramp with direct access to Lake Tohopekaliga for boating and fishing, two playgrounds, BBQ areas for gatherings, tennis courts, sports courts, and scenic nature trails amid lush greenery and lakes. Additional perks in sections like Osprey Cove include community pools and outdoor spaces, all secured by 24/7 surveillance, creating a serene yet convenient haven near Orlando's top attractions, schools, shopping, and dining.

The Oaks currently has 34 single family homes for sale with an average list price of $463,083.65, 1 townhouse for sale with a list price of $335,000, and 4 condos for sale with an average list price of $207,250. The average annual property tax for The Oaks is $4,628.41.

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 The Oaks, 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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Big Sky

Big Sky is a single-family home community in Kissimmee, Florida, built between 1959 and 2024 by Richmond American Homes and Taylor Morrison. It currently has 5 single family homes for sale with an average list price of $458,097.80. The homes range in size from 1,365 ft2 to 3,030 ft2. The HOA fees range from $63 to $278 per month. The average annual property tax for Big Sky is $3,115.99. It is located in Osceola County. ... Read more
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Eagles Nest at the Oaks

Eagles Nest at the Oaks is a single-family home community in The Oaks neighborhood of Kissimmee, Florida, built between 2003 and 2007. It currently has 3 single family homes for sale with an average list price of $371,633.33. The homes range in size from 1,617 ft2 to 2,553 ft2. The HOA fees range from $155 to $175 per month. The average annual property tax for Eagles Nest at the Oaks is $3,554.57. It is located in Osceola County. ... Read more
Median Price: $363,000
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Oak Leaf Landings

Oak Leaf Landings is a single-family home community in Kissimmee, Florida, built between 2000 and 2005. It currently has 1 single family home for sale with a list price of $595,000. The homes range in size from 1,621 ft2 to 3,592 ft2. The HOA fees range from $17 to $23 per month. The average annual property tax for Oak Leaf Landings is $4,064.10. It is located in Osceola County. ... Read more
Median Price: $477,500
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Osprey Cove

Osprey Cove is a condo community in The Oaks neighborhood of Kissimmee, Florida, built between 1997 and 2001. It currently has 4 condos for sale with an average list price of $207,250. The homes range in size from 1,034 ft2 to 1,221 ft2. The HOA fees range from $17 to $300 per month. The average annual property tax for Osprey Cove is $2,228.37. It is located in Osceola County. ... Read more
Median Price: $220,000
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Shingle Creek Reserve at the Oaks

Shingle Creek Reserve at the Oaks is a single-family home community in The Oaks neighborhood of Kissimmee, Florida, built between 2007 and 2018. It currently has 17 single family homes for sale with an average list price of $466,226.12. The homes range in size from 1,322 ft2 to 4,303 ft2. The HOA fees range from $7 to $183 per month. The average annual property tax for Shingle Creek Reserve at the Oaks is $5,489.27. It is located in Osceola County. ... Read more
Median Price: $375,000

Subdivisions

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Market Trends

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Real Estate News

Homes Just Sold in The Oaks: April 14th to April 20th

Homes Just Sold in The Oaks: April 14th to April 20th - April 21, 2026

The Oaks had only 1 sale during the week of Tuesday, April 14 to Monday, April 20, including and it was a single family home for sale with a list ... continue reading
New Homes For Sale This Week in The Oaks: April 10th to April 16th

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

The Oaks 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
New Construction Homes For Sale This Week in The Oaks: April 8th to April 14th

New Construction Homes For Sale This Week in The Oaks: April 8th to April 14th - April 15, 2026

The Oaks had only 1 new construction home during the week of Wednesday, April 8 to Tuesday, April 14, and it was a single family home for sale with a ... continue reading
Homes Just Sold in The Oaks: April 7th to April 13th

Homes Just Sold in The Oaks: April 7th to April 13th - April 14, 2026

The Oaks had only 1 sale during the week of Tuesday, April 7 to Monday, April 13, including and it was a single family home for sale with a list ... continue reading
Homes Just Sold in The Oaks: March 31st to April 6th

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

The Oaks 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
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