Winter Haven Homes under $500,000

Winter Haven Homes under $500,000

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County, where sunshine and serenity blend seamlessly. Known for its picturesque lakes and vibrant community, Winter Haven boasts a rich history and a plethora of outdoor activities that make it a perfect place to call home.

With over 50 lakes, Winter Haven is a haven for water enthusiasts and nature lovers alike. Whether you enjoy fishing, kayaking, or simply soaking in the stunning views, the city's natural beauty will captivate you. The iconic Cypress Gardens, once a premier tourist destination, laid the foundation for Winter Haven's reputation as a scenic paradise. Today, the city thrives with parks, walking trails, and recreational facilities that cater to families and individuals of all ages.

For those seeking their dream home in this idyllic setting, Winter Haven offers an impressive selection of properties under $500,000. From charming single-family homes with spacious yards to modern townhouses with contemporary finishes, there’s something for everyone. These homes provide a perfect blend of affordability and quality, allowing you to enjoy the best of Florida living without breaking the bank.

In addition to its stunning homes, Winter Haven is conveniently located near major highways, making commuting to nearby cities like Orlando and Tampa a breeze. With a warm climate, friendly community, and an array of amenities, it’s no wonder that Winter Haven is becoming a sought-after destination for homebuyers.

Explore the possibilities of living in this delightful city, where your ideal home awaits!

Newest Winter Haven Homes under $500,000

4446 Glenns Landing, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 03 SubDv. ⋅ 33884 Zip Code
LOCATION! LOCATION! LOCATION! SPRING-FED LAKE DEXTER WITH REMARKABLY CLEAR WATER! Welcome to CYPRESS LANDING, one of Winter Haven's hidden gems, offering an incredible Florida lake lifestyle! Residents enjoy private community access to beautiful LAKE DEXTER, featuring a PRIVATE BOAT RAMP, BOAT STORAGE OPTIONS, COMMUNITY BOAT DOCK WITH BOAT SLIPS, WATERFRONT SWIMMING POOL, CLUBHOUSE, TENNIS COURTS, AND SCENIC LAKESIDE WALKING PATHS! Boat storage and boat slips are community amenities; availability, fees, and usage requirements are subject to HOA confirmation. Golf carts are also permitted, subject to community guidelines! Located at 4446 GLENNS LANDING, this inviting 3-BEDROOM, 2-BATHROOM HOME features a BRAND-NEW CENTRAL A/C SYSTEM AND NEW DUCTWORK! Inside, you'll find CERAMIC TILE FLOORING THROUGHOUT, spacious living and dining areas, and a beautiful kitchen featuring GRANITE COUNTERTOPS AND STAINLESS STEEL APPLIANCES! Expansive rear sliding glass doors bring the outdoors in, seamlessly connecting the interior living space to the covered, screened porch and creating an inviting atmosphere for entertaining or simply enjoying Florida living. The primary suite offers a WALK-IN CLOSET AND PRIVATE BATHROOM WITH A WALK-IN SHOWER, while a skylight brings additional natural light into the home. An interior laundry room and attached garage provide everyday convenience. ENJOY FLORIDA LIVING WITH TWO COVERED, SCREENED PORCHES, both featuring ceramic tile flooring! An UPGRADED PAVER DRIVEWAY, lush St. Augustine lawn, mature shade trees, and attractive landscaping add to the home's curb appeal. JUST MINUTES FROM LEGOLAND FLORIDA RESORT, shopping, dining, entertainment, and Winter Haven's renowned CHAIN OF LAKES! Enjoy boating, fishing, kayaking, and waterfront recreation right within your community, with additional public boat ramps nearby. SPRING-FED LAKE DEXTER ACCESS, BRAND-NEW A/C AND DUCTWORK, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, TWO SCREENED PORCHES, AND EXCEPTIONAL COMMUNITY AMENITIES! Experience the benefits of lake community living without the waterfront price tag. SCHEDULE YOUR PRIVATE SHOWING TODAY!

4446 Glenns Landing, Winter Haven
70 Greenfield Court, Winter Haven
$475,000
4 Beds ⋅ 3 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
CYPRESSWOOD MASTERPIECE!!! This breathtaking 4BR/2.5BA residence sits across from a tranquil pond & Cypresswood's sprawling par 5 15th hole. Enjoy the view from your large covered front porch at the end of your quiet cul-de-sac. Offering nearly 2300SqFt of living area and almost 3500SqFt under roof, updates and upgrades are found throughout this gorgeous property. Features include: large downstairs primary suite with fully renovated bath and generous walk-in closet, expansive island in kitchen, under counter, microwave, custom cabinetry, solid surface floors downstairs, granite countertops, upstairs and downstairs laundry hook-up, stainless appliances, pot filler on range, fireplace, downstairs half bath, bonus room upstairs, ample closet space, large screened rear patio, paver fire pit and outdoor patio, mature landscaping, 2 car side load garage, and the list goes on!!! Community features a 24hr Guarded and Gated entrance, golf, pool, tennis, pickleball, clubhouse, restaurant!!! Right off HWY 27 and close to medical, shopping, dining, and Legoland. This property and this community are both wonderful places to call home....

70 Greenfield Court, Winter Haven
Winter Haven
$425,000
4 Beds ⋅ 4 Baths ⋅ Ida Lake Sub SubDv. ⋅ 33881 Zip Code
INVESTMENT OPPORTUNITY - NEW EXTERIOR PAINT JOB, NEW FRONT ROOF, 3 REMODELED UNITS, CENTRAL A/C. DON'T PASS UP THIS TURNKEY OPPORTUNITY. THIS 1984 QUADRUPLEX IS CONVENIENTLY LOCATED A BLOCK OFF HIGHWAY 17 BETWEEN HIGHWAY 92 AND HAVENDALE IN WINTER HAVEN. THIS MAKES IT VERY EASY TO ACCESS SHOPS AND RESTAURANTS. RENTS NORMALLY AVERAGE BETWEEN $ 850 - $ 950 PER MONTH FOR EACH OF THE FOUR UNITS. OWNER NORMALLY PAYS VERY LITTLE IN UTILITIES. ALL INTERESTED PARTIES SHOULD NOTE THAT THE LISTING BROKER HAS A SIGNIFICANT FINANCIAL INTEREST IN THIS PROPERTY.

Winter Haven
3084 Captain Jax Way, Winter Haven
$227,590
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3084 Captain Jax Way, Winter Haven
3437 Grenville Drive, Winter Haven
$223,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Discover this 2-bedroom, 2-bath home filled with potential and ready for its next owner. Located in Traditions at Lake Ruby, a maintenance-free, gated 55+ community, this thoughtfully designed home combines comfort, functionality, and style for relaxed Florida living. The kitchen features maple wood cabinetry, an updated microwave, reverse osmosis at the kitchen sink, and a convenient closet pantry. The dining area is highlighted by vaulted ceilings and a decorative arched pass-through to the kitchen, adding character and charm. The open-concept floor plan offers a spacious living room with a decorative planter shelf and triple sliding glass doors leading to the Florida room, where tranquil garden views create a peaceful setting. The primary bedroom suite offers serene backyard views and a walk-in closet. The en-suite primary bathroom is designed for comfort, featuring a comfort-height vanity, tile flooring, and a walk-in shower with a glass door. Enjoy outdoor living even during inclement weather from the Florida room, while the low-maintenance courtyard, enhanced with pavers and Florida-friendly landscaping, provides a private and inviting outdoor retreat. The fenced backyard with mature plantings offers additional outdoor space. Additional features include a laundry pantry with washer and dryer, architectural shingle roof (2020), HVAC system (2017), exterior lighting, water softener system, gutters, a glass entry storm door, and a two-car garage. A paved driveway and walkway further enhance the home's curb appeal. Traditions at Lake Ruby offers an impressive array of amenities, including a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, tennis and basketball courts, bocce, shuffleboard, fitness center, and aerobics studio. Residents can also enjoy a variety of planned community activities. Monthly HOA fees cover front-yard lawn service, cable tv, internet, exterior house painting, and community clubhouse amenities helping provide a convenient, low-maintenance lifestyle. Ideally located near shopping, restaurants, medical facilities, Legoland, and major routes, this home offers a wonderful combination of comfort, convenience, and vibrant community living.

3437 Grenville Drive, Winter Haven
251 Greenfield Road, Winter Haven
$224,900
3 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
VACANT AND PRICED TO SELL! NEW ROOF 2025! 3 BED 2 BATH CONCRETE BLOCK STUCCO (CBS) HOME IN GUARD GATED CYPRESSWOOD GOLF AND COUNTRY CLUB, WINTER HAVEN FL 33884. Vacant single story home on a 0.44 acre lot with an attached garage, central air, and no CDD. Roof replaced 2025 and water heater 2017. The home needs some work and is priced for its condition. Seller is open to making repairs needed for FHA or conventional loan approval. Cypresswood is a golf cart friendly golf course community with a 24 hour guard gate, 18 hole championship golf course, clubhouse, community pool, and tennis. Located in Polk County near Legoland Florida, Cypress Gardens, the Chain of Lakes, shopping, dining, US 27, and the I-4 corridor between Orlando and Tampa. FHA, VA, conventional, and cash welcome. Sold as is.

251 Greenfield Road, Winter Haven
6240 Pinehurst Loop, Winter Haven
$415,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Phase Ii North SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to your dream retirement home located at 6240 Pinehurst Loop Winter Haven, Fl. 33884, designed with 3 Bedrooms and 2 full bathrooms. This delightful Sebastian home in the highly sought after Lake Ashton, a 55 plus community in Central Florida, was BUILT in 2022. It features a spacious living area with Trey Ceiling and abundant Natural light thru the Glass Front Entry Door, Triple Sliders in the LR and Double Glass Window in the Dinette area; Plantation Shutters in the Bedrooms, an Upgraded Kitchen with Stainless Steel Appliances, Under Cabinet Lighting, Breakfast Bar, Walk in Pantry, Cabinet Pantry with Pull Out Drawers and Granite countertop. The inviting living and dining areas blend seamlessly together with carpet flooring, while the open-concept layout is beautifully enhanced by tile flooring in the kitchen, laundry, guest bathroom/hall, entry and Primary Suite bath. Two spacious guest bedrooms and a full bath are located near the front entry; a pocket door provides privacy and a Linen Closet provides storage. The guest bath with comfort height vanity and Granite counter top has a glass block above the tiled shower/tub combo. The Primary Suite is a private retreat on the back of the home, complete with a generously sized bathroom with separate comfort height vanities, a tiled corner shower with glass block accent above and a separate walk in closet. Step outside and enjoy the screened and covered lanai that overlooks the seasonal pond, perfect for entertaining. Plumbing was added to the privacy wall on the wall of the lanai at the time of build. The laundry room with wash sink is spacious and is accessible from the garage and kitchen. The exterior of the home has been well maintained with landscaped flower beds and the double car garage with separate golf cart entry is a bonus. A water filtration system is located in the garage. Don't miss the opportunity to explore this wonderful property! Lake Ashton is a Florida Retirement Community that offers a Florida Retirement Lifestyle with resort style amenities and activities for 55+ in Florida. The main clubhouse offers a movie theater, bowling lanes, grand ballroom, card, craft and billiards, outdoor temperature controlled swimming pool, Bocce Courts, tennis courts, 1/2 court basketball, shuffleboard courts and MORE. The Health and Fitness Center has a large indoor temperature controlled pool, fitness center, indoor 1/2 court basketball, indoor racquetball, large multi-purpose room, card, craft, billiards, pickle ball courts and tennis courts. 2 -18 hole golf courses are located in Lake Ashton (memberships are optional). Tour this well maintained home today! You'll be glad you did!

6240 Pinehurst Loop, Winter Haven
4235 Cedarwood Street, Winter Haven
$109,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right into this beautifully maintained home located in Oakwood Estates, a 55+ community. The metal roof is only 6 years old. The home has newer windows and a new vapor barrier. The lanai has all new windows. The home also has a water filtration system. The furnishings you see will stay with the home. The living and dining room give a very open and inviting feel. The kitchen bar offers additional eating space for when the whole family comes to visit. The ample kitchen cabinetry has been updated. The only carpet remaining in the home is in the guest bedroom, but it is in very good condition. Sit on the front porch or side lanai for your morning coffee. Enjoy the peaceful community or join in to the many activities available year round. The community offers two pools, two clubhouses, shuffleboard, tennis courts, bocci ball, miniature golf, and much, much more. Make your appointment today.

4235 Cedarwood Street, Winter Haven
1568 S Lake Shipp Drive, Winter Haven
$269,900
3 Beds ⋅ 2 Baths ⋅ Lake Shipp Heights SubDv. ⋅ 33880 Zip Code
New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. This property is being sold furnished, and includes AirBNB bookings.

1568 S Lake Shipp Drive, Winter Haven
2746 Adeline Avenue, Winter Haven
$286,490
3 Beds ⋅ 2 Baths ⋅ Willowbrook South SubDv. ⋅ 33881 Zip Code
Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary bedroom, you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom features luxury vinyl plank flooring that will be sure to stand out. It also has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

2746 Adeline Avenue, Winter Haven
226 Sunfish Drive, Winter Haven
$345,000
4 Beds ⋅ 2 Baths ⋅ Lake Lucerne Ph 2& 3 SubDv. ⋅ 33881 Zip Code
Welcome to 226 Sunfish Drive in Winter Haven, FL! Built in 2019, this spacious two-story home offers 4 bedrooms, 2 bathrooms, and approximately 2,746 square feet of living space. With a generous floor plan and plenty of room to spread out, this home provides flexibility for everyday living, entertaining, and relaxation. The two-story design offers ample space to accommodate a variety of lifestyles, while the backyard provides opportunities for outdoor enjoyment. Conveniently located in Winter Haven, with access to local shopping, dining, schools, and recreational activities. Whether you’re looking for additional living space or a place to make your own, this property offers plenty of potential. Don’t miss the opportunity to explore all this home has to offer. Schedule your showing today!

226 Sunfish Drive, Winter Haven
3996 Giorgio Drive, Winter Haven
$280,000
3 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Under Construction. Brand new, energy-efficient home available by Dec 2026! Enjoy open-concept living with a chef-inspired kitchen overlooking the great room and dining area. The spacious primary suite offers a peaceful retreat and includes a large walk-in closet. 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.

3996 Giorgio Drive, Winter Haven
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