Winter Haven, FL, Real Estate

Winter Haven, Florida, nestled in the heart of Polk County, is a vibrant city known for its picturesque chain of lakes, historic charm, and family-friendly attractions. Often called the "City of 100 Lakes," it offers abundant opportunities for boating, fishing, and water sports, with its interconnected waterways creating a scenic backdrop. The city gained fame as the home of Cypress Gardens, one of Florida’s earliest theme parks, now part of LEGOLAND Florida Resort, a major draw for visitors. Winter Haven’s downtown boasts quaint shops, local eateries, and a welcoming community atmosphere, while its proximity to major cities like Orlando and Tampa makes it a convenient hub. With a rich history, including its role in the citrus industry, and a warm, sunny climate, Winter Haven blends small-town appeal with modern amenities.

Winter Haven currently has 1003 single family homes for sale with an average list price of $352,560.65, 20 townhouses for sale with an average list price of $238,408.85, 79 condos for sale with an average list price of $146,909.95, and 75 lots for sale with an average list price of $632,685.87. The average annual property tax for Winter Haven is $2,187.47.

Current Homes for Sale

Schools

School District Level Grades
Alta Vista Elementary School Polk School District Elementary PK, KG-5
Alturas Elementary School Polk School District Elementary PK, KG-5
Auburndale Central Elementary School Polk School District Elementary PK, KG-5
Bethune Academy Polk School District Elementary PK, KG-5
Chain Of Lakes Elementary School Polk School District Elementary PK, KG-5
Clarence Boswell Elementary School Polk School District Elementary PK, KG-5
Dale R Fair Babson Park Elementary Polk School District Elementary K-5
Davenport School Of The Arts Polk School District Elementary PK, KG-8
Eagle Lake Elementary School Polk School District Elementary PK, KG-5
Eastside Elementary School Polk School District Elementary PK, KG-5
Elbert Elementary School Polk School District Elementary PK, KG-5
Frank E. Brigham Academy Polk School District Elementary PK, KG-5
Fred G. Garner Elementary School Polk School District Elementary PK, KG-5
Garden Grove Elementary School Polk School District Elementary PK, KG-5
Hartridge Academy Polk School District Elementary K-5
Inwood Elementary School Polk School District Elementary PK, KG-5
Jewett School Of The Arts Polk School District Elementary PK, KG-8
John Snively Elementary Polk School District Elementary PK, KG-5
Lake Alfred Elementary School Polk School District Elementary PK, KG-5
Lake Shipp Elementary School Polk School District Elementary PK, KG-5
Lena Vista Elementary School Polk School District Elementary PK, KG-5
Loughman Oaks Elementary School Polk School District Elementary PK, KG-5
Pinewood Elementary School Polk School District Elementary PK, KG-5
Wahneta Elementary School Polk School District Elementary PK, KG-5
Walter Caldwell Elementary School Polk School District Elementary PK, KG-5
Boone Middle School Polk School District Middle 6-8
Crystal Lake Middle School Polk School District Middle 6-8
Denison Middle School Polk School District Middle 6-8
Discovery Academy of Lake Alfred Polk School District Middle 6-8
Frostproof Middle/Senior High School Polk School District Middle 6-12
Lake Alfred Polytech Academy Polk School District Middle 5-8
Lakeland Highlands Middle School Polk School District Middle 6-8
McLaughlin Academy of Excellence Polk School District Middle 6-8
Westwood Middle School Polk School District Middle 6-8
Auburndale High School Polk School District High 9-12
Haines City Senior High School Polk School District High 9-12
Lake Gibson High School Polk School District High 9-12
Lake Region High School Polk School District High 9-12
Lake Wales High School Polk School District High 9-12
Winter Haven Senior High School Polk School District High 9-12
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Schools

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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 Winter Haven, i.e. what's hot and what's not.

See What's Hot & What's Not in Winter Haven

Neighborhoods

Neighborhood Median Price
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Cypresswood Country Club

Cypresswood Country Club is a neighborhood in Winter Haven, Florida, built between 1998 and 2023. It currently has 31 single family homes for sale with an average list price of $316,693.55, 7 condos for sale with an average list price of $189,911, and 1 lot for sale with a list price of $150,000. The homes range in size from 1,682 ft2 to 3,514 ft2. The average annual property tax for Cypresswood Country Club is $2,112.99. Cypresswood Golf & Country Club is a gated, master-planned community offering a serene yet vibrant lifestyle centered around its premier golfing facilities and family-friendly environment. Residents enjoy an array of top-tier amenities, including an 18-hole championship golf course designed by Ron Garl, complete with a pro shop and practice facilities, a junior Olympic-sized swimming pool, six lighted tennis courts, and a modern wellness center for fitness enthusiasts. The community clubhouse serves as a social hub, featuring a full-service restaurant and bar, event spaces for gatherings, and organized community activities. Surrounded by scenic walking paths and lush landscapes, Cypresswood provides 24-hour guarded access, ensuring privacy and security, while its central Florida location offers easy access to nearby shopping, dining, and attractions like Legoland and Orlando. ... Read more
Median price: $269,000

Neighborhoods

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Subdivisions/Buildings

Subdivisions/Buildings Median Price
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Ashton Covey

Ashton Covey is a single-family home community in Winter Haven, Florida, built between 2024 and 2026 by Ryan Homes. It currently has 9 single family homes for sale with an average list price of $457,238.33. The homes range in size from 1,815 ft2 to 2,907 ft2. The HOA fees range from $63 to $63 per month. It is located in Polk County. ... Read more
Median Price: $411,547.50
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Audubon Place

Audubon Place is a single-family home community in Winter Haven, Florida, built between 2001 and 2006. It currently has no homes for sale. The homes range in size from 1,246 ft2 to 1,652 ft2. The HOA fees range from $35 to $40 per month. The average annual property tax for Audubon Place is $2,374.63. It is located in Polk County. ... Read more
Median Price: $291,250
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Bentley Place

Bentley Place is a single-family home community in Winter Haven, Florida, built in 2006. It currently has 2 single family homes for sale with an average list price of $389,950. The homes range in size from 2,012 ft2 to 3,034 ft2. The HOA fees range from $25 to $42 per month. The average annual property tax for Bentley Place is $2,136.48. Residents of Bentley Place condos enjoy a variety of amenities, including a community pool, clubhouse, and fishing dock, perfect for relaxation and recreation. The low HOA fees also cover maintenance of common areas, ensuring a well-kept environment. With its prime location near downtown Winter Haven, residents have easy access to restaurants, shops, and cultural events, making Bentley Place an ideal choice for those seeking comfort and convenience in a vibrant, lakefront community. ... Read more
Median Price: $315,000
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Berryhill

Berryhill is a single-family home community in Winter Haven, Florida, built between 1990 and 2001. It currently has 2 single family homes for sale with an average list price of $318,249.50. The homes range in size from 1,426 ft2 to 2,281 ft2. The HOA fees range from $17 to $24 per month. The average annual property tax for Berryhill is $2,254.56. It is located in Polk County. ... Read more
Median Price: $352,500
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Biltmore Shores

Biltmore Shores is a single-family home community in Winter Haven, Florida, built between 1953 and 2022. It currently has 4 single family homes for sale with an average list price of $237,500. The homes range in size from 811 ft2 to 2,106 ft2. The average annual property tax for Biltmore Shores is $1,740.04. It is located in Polk County. ... Read more
Median Price: $195,000
Show all 287 Subdivisions/Buildings

Subdivisions/Buildings

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Market Trends

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Nearby Golf Courses

Carefree RV Country Club

9705 Lake Bess Rd, Winter Haven, FL 33884
Par 35 • 35 holes • 2133 yards

Four Lakes Golf Club

990 La Quinta Blvd, Winter Haven, FL 33881
Par 71 • 71 holes • 6021 yards

Lake Ashton Golf Club

4000 Mulligan Ln, Winter Haven, FL 33884
Par 71 • 71 holes • 6306 yards

Lake Henry Golf Club

1 Century Dr, Winter Haven, FL 33881

Nearby Golf Courses

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Real Estate News

New Homes For Sale This Week in Winter Haven: October 10th to October 16th

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

Winter Haven had 51 new homes for sale during the week of Friday, October 10 to Thursday, October 16, including including 41 single family homes for sale with an average ... continue reading
New Construction Homes For Sale This Week in Winter Haven: October 8th to October 14th

New Construction Homes For Sale This Week in Winter Haven: October 8th to October 14th - October 15, 2025

Winter Haven had 17 new construction homes during the week of Wednesday, October 8 to Tuesday, October 14, including 17 single family homes for sale with an average list price ... continue reading
Homes Just Sold in Winter Haven: October 7th to October 13th

Homes Just Sold in Winter Haven: October 7th to October 13th - October 14, 2025

Winter Haven had 13 sales during the week of Tuesday, October 7 to Monday, October 13, including including 11 single family homes for sale with an average list price of ... continue reading
New Foreclosures & Short Sales in Winter Haven: October 6th to October 12th

New Foreclosures & Short Sales in Winter Haven: October 6th to October 12th - October 13, 2025

Winter Haven had only 1 new foreclosure and/or short sale during the week of Monday, October 6 to Sunday, October 12, and it was a single family home for sale ... continue reading
New Homes with In-ground Swimming Pools in Winter Haven: October 5th to October 11th

New Homes with In-ground Swimming Pools in Winter Haven: October 5th to October 11th - October 12, 2025

Winter Haven had new homes for sale with an in-ground swimming pool during the month of Sunday, October 5 to Saturday, October 11, including 4 single family homes for ... continue reading
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