Winter Haven Homes under $500,000

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, renowned for its picturesque lakes and vibrant community spirit. With its stunning landscapes and a rich tapestry of recreational activities, Winter Haven is a hidden gem that offers the perfect blend of small-town charm and modern conveniences.

Home to the famous Chain of Lakes, Winter Haven boasts over 50 lakes, making it a paradise for water enthusiasts. Whether you enjoy fishing, boating, or simply basking in the sun, the serene waters provide endless opportunities for outdoor fun. The city is also known for its lush parks, inviting walking trails, and family-friendly attractions, including the beloved LEGOLAND Florida Resort, which promises excitement for visitors of all ages.

When it comes to real estate, Winter Haven offers an impressive selection of homes under $500,000, making it an ideal destination for first-time buyers, families, and retirees alike. From charming single-family homes to modern townhouses, you’ll find a variety of options that cater to diverse lifestyles and budgets. Many properties boast spacious yards, updated interiors, and proximity to local amenities, ensuring that you can enjoy both comfort and convenience.

With a welcoming community, excellent schools, and a thriving local economy, Winter Haven is not just a place to live—it's a place to call home. Explore the endless possibilities that await you in this delightful city, and discover why Winter Haven is the perfect choice for your next real estate investment!

Newest Winter Haven Homes under $500,000

1841 5th Street Se, Winter Haven $339,000

Virtually Staged. Welcome to 1841 5th Street SE in Winter Haven, Florida, a well-maintained 3 bedroom, 2 bath home offering approximately 1,917 square feet of living spac...

3 Beds
2 Baths
Southeast Terrace SubDv.
33880 Zip Code

842 Avenue N Sw, Winter Haven $175,000

Rental income from day one in Winter Haven! This 3 bedroom, 1 bath home near downtown has a tenant in place through September 30, 2027, paying $1,350 per month, giving an...

3 Beds
1 Baths
Lake Shipp Or Porters Add SubDv.
33880 Zip Code

2825 Wingfoot Court, Winter Haven $225,000

Charming Golf Villa on the 8th Fairway in Gated Cypresswood! Enjoy views of the 8th hole fairway from this well-maintained 2-bedroom, 2-bathroom villa (1,471 sq ft) in th...

2 Beds
2 Baths
Cypresswood Golf And Country Club SubDv.
33884 Zip Code

575 Saint Andrews Road, Winter Haven image

575 Saint Andrews Road, Winter Haven $286,000

Golf Course Living with Total Peace of Mind! Welcome to your worry-free oasis on the green. Nestled within this beautiful, gated community of Cypresswood Golf and Country...

2 Beds
2 Baths
Cypresswood Patio Homes SubDv.
33884 Zip Code

10 W Lake Hamilton Circle, Winter Haven image

10 W Lake Hamilton Circle, Winter Haven $485,000

Welcome to 10 West Lake Hamilton Circle, a beautifully maintained four-bedroom, two-bathroom waterfront home situated on a spacious half-acre property in Winter Haven. Th...

4 Beds
2 Baths
Pollard Shores SubDv.
33881 Zip Code

5344 Nicklaus Drive, Winter Haven $310,000

Home for Sale in Lake Ashton, a Florida Retirement Community with Two (2) Golf Courses, Resort Style Amenities and Planned Activities like Trivia, Bingo, Dances, Day Trip...

3 Beds
2 Baths
Lake Ashton West Ph I SubDv.
33884 Zip Code

208 Golf Aire Boulevard, Winter Haven image

208 Golf Aire Boulevard, Winter Haven $249,950

Live the Florida lifestyle in this 3 bedroom, 2 bath w/office on the the Lake Bess Country & Golf club; a desirable, gated community with no age restrictions in Winter Ha...

3 Beds
2 Baths
Lake Bess Country Club SubDv.
33884 Zip Code

1015 Mockingbird Circle, Winter Haven image

1015 Mockingbird Circle, Winter Haven $284,900

Welcome to this beautifully renovated 3-bedroom, 2-bath home located on a quiet cul-de-sac in Winter Haven! Situated on a spacious .20-acre lot, this move-in-ready home h...

3 Beds
2 Baths
Garden Grove South Ph 01 & 02 SubDv.
33884 Zip Code

4766 Osprey Way, Winter Haven $289,900

New photos coming soon. Seller offering up to $12,320 toward buyer closing costs, prepaid expenses, and/or an interest rate buydown. Conditions apply. Move-in ready 4-bed...

4 Beds
2 Baths
St James Xing SubDv.
33881 Zip Code

1578 Marshall Road Sw, Winter Haven image

1578 Marshall Road Sw, Winter Haven — 1578 $175,000

TOWNHOUSE 2 BEDROOM 1.5 BATHROOM NEAR DOWNTOWN WINTER HAVEN. FEATURES DOWNSTAIRS LIVING AREAS WITH KITCHEN AND 1/2 BATHROOM, WITH LAMINATE & CERAMIC TILE FLOORS. SLIDING ...

2 Beds
2 Baths
33880 Zip Code

276 Arbuthnot Street, Winter Haven image

276 Arbuthnot Street, Winter Haven $285,000

Welcome to 276 Arbuthnot St, a beautifully maintained 3-bedroom, 2-bath home in the desirable Sanctuary by the Lake community of Winter Haven. Built in 2021, this move-in...

3 Beds
2 Baths
Sanctuary By The Lake Ph 2 SubDv.
33881 Zip Code

2758 Adeline Avenue, Winter Haven $302,990

Under Construction. Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Willowbrook South in Winter Haven, Florida. Choose betw...

5 Beds
2 Baths
Willowbrook South SubDv.
33881 Zip Code