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 41 single family homes for sale with an average list price of $451,284.10, 1 townhouse for sale with a list price of $349,990, and 1 condo for sale with a list price of $245,000. The average annual property tax for The Oaks is $4,217.74.

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 $468,899.80. 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 $2,676.41. It is located in Osceola County. ... Read more
Median Price: $478,475
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Eagles Nest at the Oaks

Eagles Nest at the Oaks is a single-family home community in the The Oaks neighborhood of Kissimmee, Florida, built between 2003 and 2007. It currently has 1 single family home for sale with a list price of $375,000. The homes range in size from 1,617 ft2 to 2,553 ft2. The HOA fees range from $155 to $165 per month. The average annual property tax for Eagles Nest at the Oaks is $3,352.82. It is located in Osceola County. ... Read more
Median Price: $364,000
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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 3 single family homes for sale with an average list price of $525,000. 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 $3,874.02. It is located in Osceola County. ... Read more
Median Price: $522,500
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Osprey Cove

Osprey Cove is a condo community in the The Oaks neighborhood of Kissimmee, Florida, built between 1997 and 2001. It currently has 1 condo for sale with a list price of $245,000. The homes range in size from 1,034 ft2 to 1,221 ft2. The HOA fees range from $17 to $278 per month. The average annual property tax for Osprey Cove is $2,010.06. 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 The Oaks neighborhood of Kissimmee, Florida, built between 2007 and 2020. It currently has 18 single family homes for sale with an average list price of $439,697.11. 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 $4,795.75. It is located in Osceola County. ... Read more
Median Price: $380,000

Subdivisions

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Market Trends

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Real Estate News

New Homes For Sale This Week in The Oaks: October 10th to October 16th

New Homes For Sale This Week in The Oaks: October 10th to October 16th - October 17, 2025

The Oaks had only 1 new home for sale during the week of Friday, October 10 to Thursday, October 16, including and it was a single family home for sale ... continue reading
Homes Just Sold in The Oaks: September 30th to October 6th

Homes Just Sold in The Oaks: September 30th to October 6th - October 7, 2025

The Oaks had only 1 sale during the week of Tuesday, September 30 to Monday, October 6, including and it was a single family home for sale with a list ... continue reading
Homes Just Sold in The Oaks: September 23rd to September 29th

Homes Just Sold in The Oaks: September 23rd to September 29th - September 30, 2025

The Oaks had 2 sales during the week of Tuesday, September 23 to Monday, September 29, including including 1 single family home for sale with a list price of $389,950 ... continue reading
New Homes with In-ground Swimming Pools in The Oaks: September 21st to September 27th

New Homes with In-ground Swimming Pools in The Oaks: September 21st to September 27th - September 28, 2025

The Oaks had only new homes for sale with an in-ground swimming pool during the month of Sunday, September 21 to Saturday, September 27, and it was a single ... continue reading
New Homes For Sale This Week in The Oaks: September 19th to September 25th

New Homes For Sale This Week in The Oaks: September 19th to September 25th - September 26, 2025

The Oaks had 2 new homes for sale during the week of Friday, September 19 to Thursday, September 25, including including 2 single family homes for sale with an average ... continue reading
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