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 11 single family homes for sale with an average list price of $375,163.36. The average annual property tax for Cypress Woods is $2,871.87.

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 2004. It currently has 2 single family homes for sale with an average list price of $404,500. 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 $3,101.81. It is located in Osceola County. ... Read more
Median Price: $390,000
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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 in 2006. It currently has 1 single family home for sale with a list price of $354,900. The homes range in size from 1,731 ft2 to 2,847 ft2. The HOA fees range from $22 to $85 per month. The average annual property tax for Maple Chase at Cypress Woods is $2,459.29. 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 2000. It currently has 1 single family home for sale with a list price of $279,000. 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 $2,810.67. ... Read more
Median Price: $299,900
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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 $467,499.50. 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 $2,174.37. 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 4 single family homes for sale with an average list price of $357,225. The homes range in size from 1,459 ft2 to 3,001 ft2. The HOA fees range from $18 to $100 per month. The average annual property tax for Tamarind Parke at Cypress Woods is $2,962.70. It is located in Osceola County. ... Read more
Median Price: $357,000
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Subdivisions

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Market Trends

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Real Estate News

New Homes For Sale This Week in Cypress Woods: January 9th to January 15th

New Homes For Sale This Week in Cypress Woods: January 9th to January 15th - January 16, 2026

Cypress Woods had only 1 new home for sale during the week of Friday, January 9 to Thursday, January 15, including and it was a single family home for sale ... continue reading
Homes Just Sold in Cypress Woods: December 30th to January 5th

Homes Just Sold in Cypress Woods: December 30th to January 5th - January 6, 2026

Cypress Woods had only 1 sale during the week of Tuesday, December 30 to Monday, January 5, including and it was a single family home for sale with a list ... continue reading
Homes Just Sold in Cypress Woods: December 23rd to December 29th

Homes Just Sold in Cypress Woods: December 23rd to December 29th - December 30, 2025

Cypress Woods had only 1 sale during the week of Tuesday, December 23 to Monday, December 29, including and it was a single family home for sale with a list ... continue reading
Homes Just Sold in Cypress Woods: December 9th to December 15th

Homes Just Sold in Cypress Woods: December 9th to December 15th - December 16, 2025

Cypress Woods had only 1 sale during the week of Tuesday, December 9 to Monday, December 15, including and it was a single family home for sale with a list ... continue reading
Homes Just Sold in Cypress Woods: December 2nd to December 8th

Homes Just Sold in Cypress Woods: December 2nd to December 8th - December 9, 2025

Cypress Woods had 2 sales during the week of Tuesday, December 2 to Monday, December 8, including including 2 single family homes for sale with an average list price of ... continue reading
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