Winter Haven Homes under $500,000

Winter Haven Homes under $500,000

Welcome to Winter Haven, Florida – a charming gem nestled in the heart of Polk County. Known for its breathtaking lakes and vibrant community spirit, Winter Haven offers a unique blend of small-town charm and modern conveniences, making it an ideal place to call home.

With over 50 lakes, including the stunning Chain of Lakes, you can indulge in a variety of outdoor activities, from boating and fishing to picnicking along the shore. The city is also home to beautiful parks, scenic walking trails, and a bustling downtown area filled with delightful shops and restaurants. Whether you're enjoying a leisurely stroll or exploring local art galleries, Winter Haven has something for everyone.

For those seeking affordable housing options, Winter Haven presents an impressive selection of homes under $500,000. From cozy single-family residences to modern townhomes, buyers will find a diverse array of properties that cater to various lifestyles and preferences. Many of these homes feature spacious yards, updated interiors, and proximity to essential amenities, making them perfect for families, retirees, or first-time homebuyers.

The community is known for its friendly atmosphere and strong sense of belonging, making it easy to connect with neighbors and participate in local events. With excellent schools, convenient access to major highways, and proximity to attractions like Legoland Florida, Winter Haven truly embodies the best of Florida living.

Explore the possibilities of making Winter Haven your new home, where affordability meets a vibrant lifestyle in one of Florida's most enchanting locales. Your dream home awaits!

Newest Winter Haven Homes under $500,000

2097 Whispering Trails Boulevard, Winter Haven
$410,000
4 Beds ⋅ 3 Baths ⋅ Whispering Trails Ph 01 SubDv. ⋅ 33884 Zip Code
Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 10 minutes from the exciting attractions of Legoland, and less than an hour from the Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and amenities. This charming home comes move-in ready, including all essential appliances such as a range, refrigerator, microwave, garbage disposal. The secure, gated community offers peace of mind and added privacy, making it an ideal place to call home. Whether you're looking for a primary residence, vacation home, or investment property, this residence offers comfort, convenience, and easy access to some of Florida’s top attractions. Don’t miss your chance to own this fantastic 4 bed 3 full bath pool home in the fast-growing City of Winter Haven!

2097 Whispering Trails Boulevard, Winter Haven
135 Eloise Oaks Drive, Winter Haven
$365,000
3 Beds ⋅ 2 Baths ⋅ Eloise Oaks SubDv. ⋅ 33884 Zip Code
Remarkable 3-bedroom, 2-bathroom single-story home offering 1,866 square feet of comfortable living space on a spacious 1/4 acre lot in Winter Haven, FL. This meticulously maintained residence is packed with features designed for both comfort and style. The large kitchen is well designed for organization with granite countertops, built-in sliding drawers, and sleek stainless steel appliances. Throughout the home, you'll find elegant tray ceilings that add a touch of sophistication to the living spaces. For your peace of mind, the property is equipped with an ADT security system and a state-of-the-art Ultraviolet AC Air Purification Scrubber system, ensuring the cleanest indoor air quality for you and your family. The living area opens up to a COZY SCREENED LANAI complete with sliding windows, making it the perfect spot for year-round relaxation. Step outside to discover an entertainer's dream outdoor space featuring an EXTENDED PAVER PATIO with an elevated grilling station. The FULLY FENCED YARD provides privacy. Located in the quiet Eloise Oaks neighborhood, this home is just up the street from LAKE ELOISE, one of many lakes in the renowned Winter Haven Chain of Lakes. You'll be just minutes from LEGOLAND Florida Resort and perfectly positioned between Florida's beautiful east and west coasts as well as the Orlando attractions. This exceptional home combines comfort, style, and an unbeatable location. Schedule your showing today!

135 Eloise Oaks Drive, Winter Haven
463 Daisy Lane, Winter Haven
$259,900
2 Beds ⋅ 2 Baths ⋅ Lake Daisy Estates SubDv. ⋅ 33884 Zip Code
This well maintained Lake Daisy Estates home located in southeast Winter Haven. This 2 bedroom & 2 bathroom home is ready for its new owners. Recent Upgrades: Roof and Solar (2023), SELLER WILL PAY OFF SOLAR PANELS AT CLOSING!!! Windows and Sliding Glass Door are Renewal By Andersen (2024), retractable garage door screen (motor replaced 2026). Enjoy your 2-car garage with the door open and the mosquitoes kept out! Only ten homes on the street provides a great space for playing outside, walking, bike riding and more! Very low traffic as other roads lead to community entrances/exits! NO HOA FEES! NO CDD FEES! Electric bill for October usage was less than $17!!! The paid off solar system provides the potential to SAVE HUNDREDS OF DOLLARS EACH MONTH FOR THE LIFE OF THE SYSTEM!!! This property is ready for the new owners to make it their own. Lake Daisy Estates is approximately 1/2 mile from A rated Garden Grove Elementary School, 1 mile from the Street Audubon Nature Center, 1 1/2 miles from Wal-Mart, 2 miles from Advent Emergency, 3 miles from Publix, 4 miles from Home Depot and 5 miles to Lowe's. This home is centrally located in Florida and is approximately 50 miles from Orlando International Airport and 60 miles from the Tampa International Airport. Don’t miss out, schedule your private showing today!

463 Daisy Lane, Winter Haven
1816 5th Street Se, Winter Haven
$250,000
3 Beds ⋅ 2 Baths ⋅ Southeast Terrace SubDv. ⋅ 33880 Zip Code
Picture weekends spent exploring Winter Haven’s lakes, discovering a favorite local restaurant, and coming home to a place that feels like your own. At 1816 5th Street SE, this three-bedroom, two-bath masonry home offers an inviting setting for enjoying the Central Florida lifestyle. Set on nearly a quarter acre, the property offers room to imagine backyard cookouts, a garden, or a quiet outdoor retreat. Inside, inviting living spaces offer room to relax and feel at home, while three bedrooms provide flexibility for guests, work, or hobbies. A carport adds everyday convenience, and the roof was replaced in 2020. Enjoy the dining, parks, downtown experiences, and Chain of Lakes recreation that give Winter Haven its character. Whether you’re looking for a full-time residence, a seasonal retreat, or an opportunity to explore as a long-term rental, this home offers a place to bring your plans to life. Come see the possibilities and picture your next chapter.

1816 5th Street Se, Winter Haven
4000 Giorgio Drive, Winter Haven
$325,000
4 Beds ⋅ 3 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Dec 2026! First-floor primary suite ensures everyone has their own private space. Second floor offers a spacious loft that can be used to best fit your family's needs. Enjoy preparing meals with your family in the open kitchen with spacious work island. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

4000 Giorgio Drive, Winter Haven
1489 36th Street Nw, Winter Haven
$138,000
2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
GREAT POTENTIAL WITH A SPACIOUS, PRIVATE BACKYARD! This 2-bedroom, 1-bath concrete block home offers approximately 572 square feet of living space on a generous 0.23-acre lot. One of the property's standout features is the fully fenced backyard, surrounded by mature trees that provide a nice sense of privacy and separation. Inside, the home features a simple, functional layout with tile flooring and room for personal touches and improvements. Whether you're looking for a smaller home to make your own or an investment opportunity, this property offers several possibilities. Conveniently located near schools, shopping, and everyday amenities in Winter Haven. With a little vision and effort, this property has the potential to become something special. Schedule your showing today and see the possibilities for yourself!

1489 36th Street Nw, Winter Haven
3349 Timberline Road W, Winter Haven
$180,000
2 Beds ⋅ 2 Baths ⋅ Timber Wood SubDv. ⋅ 33880 Zip Code
GREAT OPPORTUNITY TO BUILD SWEAT EQUITY IN WINTER HAVEN! Looking for a fixer-upper with potential, an investment property, or a home you can make your own? This 2-bedroom, 1.5-bath concrete block home offers approximately 904 square feet of living space, a one-car garage, and plenty of possibilities for the right buyer. Two significant improvements include a roof installed in 2019 and an HVAC system replaced in 2024. While the home does need repairs and renovations, it presents an opportunity for buyers willing to put in the work and bring their own vision to life. Conveniently situated near schools, shopping, dining, and major roadways, with easy access to surrounding Central Florida communities. Whether you're a first-time buyer looking to build sweat equity, an investor searching for your next project, or someone who enjoys transforming a property, this home offers a great starting point. Bring your creativity and discover the possibilities!

3349 Timberline Road W, Winter Haven
1904 3rd Street Ne, Winter Haven
$220,000
4 Beds ⋅ 2 Baths ⋅ Florence Village SubDv. ⋅ 33881 Zip Code
Home sweet home, In the heart of Winter Haven. This updated 4 beds; 2 bath family home can be yours. This home has been upgraded with stainless steel appliances, granite countertops, and new flooding in the bedrooms. Warm and welcoming yard for family gatherings or simply relaxing and rejuvenating from the workday.

1904 3rd Street Ne, Winter Haven
1619 Pearce Road Nw, Winter Haven
$255,900
2 Beds ⋅ 1 Baths ⋅ Lake View Sub SubDv. ⋅ 33881 Zip Code
THIS COULD BE THE ONE. PRIVATE POOL! So many possibilities! Lovely vaulted ceilings, double fireplace, open kitchen, lovely wood accents, mahogany kitchen cabinets, 2 car garage/ carport and a separate workshop all on .75 of an acre. Fixer upper!

1619 Pearce Road Nw, Winter Haven
5378 San Pietro Drive, Winter Haven
$396,828
5 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code
Under Construction. Valencia BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender.  Prepare to be impressed by the Valencia, a two-story home featuring 5 bedrooms, 3 bathrooms, and a 2-car garage. This floorplan is designed for modern living and effortless entertainment. Step through the elegant foyer into a vibrant main living area, complete with a private guest suite for ultimate comfort. The kitchen shines with sleek quartz countertops, stainless steel appliances, and luxurious vinyl plank flooring overlooking the dining area which flows beautifully to the covered lanai through sliding glass doors. Upstairs, you’ll find the secluded owner’s suite complete with a walk-in shower, dual vanity and spacious walk-in closet. Conveniently located by the additional bedrooms is the cleverly designed oversized laundry room. Another modern feature of the Valencia is the smart thermostat with voice control, making energy efficient living a breeze. Outside, enjoy the chic elevation and professionally curated landscaping that adds the perfect finishing touch to this exceptional home. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5378 San Pietro Drive, Winter Haven
5357 San Pietro Drive, Winter Haven
$329,990
4 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code
Under Construction. Turquesa BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender.  The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.   Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5357 San Pietro Drive, Winter Haven
2656 Trinity Circle Nw, Winter Haven
$239,000
2 Beds ⋅ 2 Baths ⋅ Haven Groves Estates SubDv. ⋅ 33881 Zip Code
Discover the possibilities and bring your personal charm. This 2-bedroom, 2-bath home features spacious bedrooms, a separate dining room, and a versatile bonus room that could be converted into a 3rd bedroom, subject to applicable requirements. The bonus room also offers options for a home office, hobby room, or additional living space. An indoor laundry room adds everyday convenience, while the storage shed provides extra space for tools, seasonal items, and outdoor equipment. Conveniently located near the intersection, this home offers plenty of potential to make it your own. Schedule your showing today! Buyer to verify actual square footage.

2656 Trinity Circle Nw, Winter Haven
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