Cypress Woods, Kissimmee, FL, Real Estate

Residents enjoy a variety of amenities, including a community pool, fitness center, playground, basketball and tennis courts, a park, and a clubhouse, fostering an active and social environment. With deed restrictions ensuring a well-maintained community and proximity to schools, shopping, and major highways, Cypress Woods is an appealing choice for those seeking affordable Florida living with modern conveniences.

Cypress Woods currently has 20 single family homes for sale with an average list price of $366,239.30. The average annual property tax for Cypress Woods is $2,617.83.

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 Cypress Woods, 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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Banyan Cove at Cypress Woods

Banyan Cove at Cypress Woods is a single-family home community in the Cypress Woods neighborhood of Kissimmee, Florida, built between 2003 and 2018. It currently has 4 single family homes for sale with an average list price of $427,250. The homes range in size from 1,731 ft2 to 3,047 ft2. The HOA fees range from $18 to $95 per month. The average annual property tax for Banyan Cove at Cypress Woods is $2,812.79. It is located in Osceola County. ... Read more
Median Price: $380,000
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Maple Chase at Cypress Woods

Maple Chase at Cypress Woods is a single-family home community in the Cypress Woods neighborhood of Kissimmee, Florida, built between 2005 and 2006. It currently has 2 single family homes for sale with an average list price of $373,949.50. The homes range in size from 1,731 ft2 to 2,847 ft2. The HOA fees range from $22 to $286 per month. The average annual property tax for Maple Chase at Cypress Woods is $2,396.43. It is located in Osceola County. ... Read more
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Pepper Tree at Cypress Woods

Pepper Tree at Cypress Woods is a single-family home community in the Cypress Woods neighborhood of Kissimmee, Florida, built between 1997 and 2001. It currently has 5 single family homes for sale with an average list price of $322,198. The homes range in size from 1,175 ft2 to 2,819 ft2. The HOA fees range from $19 to $105 per month. The average annual property tax for Pepper Tree at Cypress Woods is $2,567.36. ... Read more
Median Price: $285,000
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Pinehurst at Cypress Woods

Pinehurst at Cypress Woods is a single-family home community in the Cypress Woods neighborhood of Kissimmee, Florida, built between 1997 and 1998. It currently has 2 single family homes for sale with an average list price of $477,499.50. The homes range in size from 1,597 ft2 to 2,830 ft2. The HOA fees range from $19 to $233 per month. The average annual property tax for Pinehurst at Cypress Woods is $2,257.85. It is located in Osceola County. ... Read more
Median Price: $374,999
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Tamarind Parke at Cypress Woods

Tamarind Parke at Cypress Woods is a single-family home community in the Cypress Woods neighborhood of Kissimmee, Florida, built between 2000 and 2002. It currently has 5 single family homes for sale with an average list price of $334,580. The homes range in size from 1,459 ft2 to 3,010 ft2. The HOA fees range from $18 to $90 per month. The average annual property tax for Tamarind Parke at Cypress Woods is $2,737.38. It is located in Osceola County. ... Read more
Median Price: $374,000
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Subdivisions

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Market Trends

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Real Estate News

Homes Just Sold in Cypress Woods: November 25th to December 1st

Homes Just Sold in Cypress Woods: November 25th to December 1st - December 2, 2025

Cypress Woods had only 1 sale during the week of Tuesday, November 25 to Monday, December 1, including and it was a single family home for sale with a list ... continue reading
New Foreclosures & Short Sales in Cypress Woods: November 24th to November 30th

New Foreclosures & Short Sales in Cypress Woods: November 24th to November 30th - December 1, 2025

Cypress Woods had only 1 new foreclosure and/or short sale during the week of Monday, November 24 to Sunday, November 30, and it was a single family home for sale ... continue reading
New Homes For Sale This Week in Cypress Woods: November 21st to November 27th

New Homes For Sale This Week in Cypress Woods: November 21st to November 27th - November 28, 2025

Cypress Woods had only 1 new home for sale during the week of Friday, November 21 to Thursday, November 27, including and it was a single family home for sale ... continue reading
Homes Just Sold in Cypress Woods: October 21st to October 27th

Homes Just Sold in Cypress Woods: October 21st to October 27th - October 28, 2025

Cypress Woods had only 1 sale during the week of Tuesday, October 21 to Monday, October 27, including and it was a single family home for sale with a list ... continue reading
New Homes with In-ground Swimming Pools in Cypress Woods: October 12th to October 18th

New Homes with In-ground Swimming Pools in Cypress Woods: October 12th to October 18th - October 19, 2025

Cypress Woods had only new homes for sale with an in-ground swimming pool during the month of Sunday, October 12 to Saturday, October 18, and it was a single ... continue reading
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