Winter Haven Homes under $500,000

Winter Haven Homes under $500,000

Welcome to Winter Haven, Florida – a hidden gem nestled in the heart of Polk County! Known for its stunning chain of lakes and vibrant community spirit, Winter Haven offers a unique blend of small-town charm and modern conveniences. With its lush landscapes, abundant recreational opportunities, and friendly atmosphere, it's no wonder that this city is becoming a sought-after destination for families, retirees, and everyone in between.

Winter Haven is famous for its picturesque lakes that provide endless opportunities for boating, fishing, and water sports. The city is also home to the renowned LEGOLAND Florida Resort, making it a fantastic place for families to enjoy fun-filled days. With a thriving downtown area, you'll find delightful shops, cozy cafes, and a variety of dining options that cater to every palate.

For those looking to plant roots in this beautiful city, Winter Haven offers an impressive array of homes priced under $500,000. Whether you’re seeking a charming single-family home, a modern townhouse, or a cozy condo, there’s something for everyone. These properties not only provide affordability but also the chance to be part of a community that values connection and quality of life.

With its welcoming neighborhoods, excellent schools, and a plethora of parks and recreational facilities, Winter Haven is the perfect place to call home. Discover the ideal balance of tranquility and excitement in this enchanting city, where your dream home awaits! Come experience the warmth and beauty of Winter Haven, Florida – where life is truly a little sweeter.

Newest Winter Haven Homes under $500,000

1657 Vienna Square Drive, Winter Haven

1657 Vienna Square Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Vienna Square Ph 2b SubDv. ⋅ 33884 Zip Code

END-UNIT VILLA IN VIENNA SQUARE WITH POND VIEW. ENJOY PRIVACY, COMFORT AND A POND VIEW IN THIS 2 BEDROOM - 2 BATH END UNIT VILLA OFFERING ALMOST 1500 SQ FR OF LIVING AREA. LOCATED IN THE DESIREABLE SOUTHEAST AREA. ENJOY THIS 55 PLUS GATED COMMUNITY. THIS HOME FEATURES A SPLIT BEDROOM DESIGN, OPEN GREAT ROOM, CERAMIC TILE AND PLANTATION SHUTTERS THOUGHOUT. THE UPGRADED KITCHEN INCLUDES GRANITE COUNTERTOPS WITH APPLIANCES, INCLUDING WASHER & DRYER. THE SPACIOUS PRIMARY SUITE OFFERS DOUBLE CLOSETS AND A PRIVATE BATH WITH A WALK IN SHOWER. ADDITIONAL HIGHLIGHTS INCLUDE A TWO-CAR GARAGE, BRICK-PAVER DRIVEWAY AND A PEACEFUL END UNIT SETTING, OVERLOOKING THE POND. THE COMMUNITY AMENITIES INCLUDE: GATED COMMUNITY; CLUBHOUSE; RESORT-STYLE POOL; TENNIS COURTS. CONVENIENTLY LOCATED NEAR THE NEW PUBLIX ON DUNDEE ROAD WITH EASY ACCESS TO HIGHWAY 27 TO I-4 TO TAMPA, ORLANDO-DISNEY. DOWNTOWN WINTER HAVEN IS APPROXIMATELY 10 MIN TO RESTAURANTS, PARK WITH EVENTS, LIBRARY AND COMMUNITY EVENTS. THE FREE CYPRESS GARDENS SKI SHOW IS ALSO HELD ON LAKE SILVER. DISCOVER YOUR RELAXED FLORIDA LIVING AT IT'S BEST AT VIENNA SQUARE!

1657 Vienna Square Drive, Winter Haven

5344 Nicklaus Drive, Winter Haven

5344 Nicklaus Drive, Winter Haven

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

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 Trips, Holiday Events and MORE! This 3 Bedroom and 2 Bath home with over 1,600 sq. ft. living area would be a great seasonal home. The furniture in this home is negotiable. The exterior of this home has paver drive and walk ways, mature and well maintained landscape with rock-scape and landscape edging, a screened entry at the Front Door, and a Covered Lanai, on the front of the home, which is large enough for chairs. An irrigation system provides water to the large and beautiful Palm tree and other mature landscape around the home. This seasonally occupied and well maintained home offers an Open and Spacious Split Floor Plan with NO CARPET ANYWHERE! The kitchen features SS appliances (oven-December 2022, refrigerator 2021), Corian countertops, Dinette area with Bay Windows, Step Up breakfast bar and closet pantry. New Anderson Windows have been installed in the Dining room, Primary Bedroom and Primary Bathroom. Laminate flooring is in each of the bedrooms. The Primary Suite has 2 large walk-in closets, His/Her comfort height vanities, a Water closet and Large walk-in shower. The washer/dryer in the laundry room will be included in the sale of this home. The outdoor living area offers a 26 x 10 rear screened lanai and large paver area that is great for grilling. The 2 car garage is equipped with a "Skeeter Beater" for privacy and enjoying the cool cross breeze! Lake Ashton that offers 2 clubhouses, indoor and outdoor heated pools, pickle ball, tennis courts, racquetball, basketball, fitness centers, movie theaters, craft room, media center, several private lakes, private boat ramp/slips and more!! Come and enjoy your retirement and carefree living in the beautiful gated and guarded community of Lake Ashton today!

5344 Nicklaus Drive, Winter Haven

208 Golf Aire Boulevard, Winter Haven

208 Golf Aire Boulevard, Winter Haven

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

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 Haven. The layout of the home enhances a welcoming and roomy atmosphere. As you enter you are greeted by a large entry foyer that opens up to a spacious living room. The high ceilings and large double pane windows allow natural light to flood the home. Life at Lake Bess Country Club is about more than just owning a home—it's embracing a lifestyle. Enjoy unlimited access to the immaculately maintained executive golf course, relax by the heated community pool, gather with neighbors at the clubhouse, or simply enjoy the gentle breeze while watching golfers pass by from the comfort of your own backyard. The monthly HOA fee of $500 includes lawn care, shrub maintenance, the heated community pool, and clubhouse access, as well as, unlimited golf on the beautifully maintained executive course—an outstanding value for those who love the game. If you've been searching for spectacular views, a peaceful setting, and maintenance-free Florida living in a secure gated community, this is the one. Schedule your private showing today!

208 Golf Aire Boulevard, Winter Haven

1015 Mockingbird Circle, Winter Haven

1015 Mockingbird Circle, Winter Haven

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

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 has been thoughtfully updated throughout with a fresh, modern feel. Step inside to find new luxury vinyl plank flooring, a completely remodeled kitchen, beautifully updated bathrooms, and a separate laundry room. The former garage has been fully enclosed, providing additional versatile living space perfect for a family room, home office, game room, or flex space. The newly renovated kitchen offers a clean, contemporary look, with stainless steel appliances to be installed soon. The light and bright interior provides a welcoming atmosphere with plenty of room to make this home your own. Enjoy the peaceful setting of a cul-de-sac while still being conveniently located near shopping, dining, medical facilities, schools, and all that Winter Haven has to offer. Known for its beautiful Chain of Lakes and central Florida location, Winter Haven provides easy access to LEGOLAND Florida Resort and is conveniently positioned between the Orlando and Tampa areas. Whether you’re searching for your primary residence or a Florida getaway, this updated home is ready for its new owners. Schedule your private showing today!

1015 Mockingbird Circle, Winter Haven

4766 Osprey Way, Winter Haven

4766 Osprey Way, Winter Haven

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

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-bedroom, 2-bath home in Winter Haven's established St James Crossing community. The kitchen features granite countertops, an island with bar seating, and stainless steel appliances including a range, dishwasher and microwave. The single-story split floor plan offers 1,999 SqFt with wood-look laminate flooring throughout and no carpet anywhere, a living room open to the dining area and kitchen, a primary suite with a walk-in closet and a private bath with a walk-in shower, three additional bedrooms (two with walk-in closets), a second full bath, an inside laundry room, and an attached 2-car garage. Out back, sliding glass doors open to a covered patio on a 0.17-acre lot that backs to a tree line. $210 annual HOA and no CDD. Flood Zone X, so no flood insurance is required. Conveniently located near shopping, dining and schools. Buyer credit available with use of Seller's preferred lender. Schedule your showing today.

4766 Osprey Way, Winter Haven

1578 Marshall Road Sw, Winter Haven

1578 Marshall Road Sw, Winter Haven

2 Beds ⋅ 2 Baths ⋅ 33880 Zip Code

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 GLASS DOORS OFF LIVING ROOM OPENS UP TO SCREEND-IN-PORCH, WITH ACCESS TO FENCED IN BACK YARD. UPSTAIRS FEATURES; 2 LARGE BEDROOMS WITH FULL BATHROOM WITH TUB'SHOWER & SKYLIGHT, HIS & HER CLOSETS. THIS TOWNHOUSE COMES WITH A 2 CAR GARAGE AND PRIVATE FRONT PATIO AREA.

1578 Marshall Road Sw, Winter Haven

276 Arbuthnot Street, Winter Haven

276 Arbuthnot Street, Winter Haven

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

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-ready home offers approximately 1,420 square feet of thoughtfully designed living space with an open-concept floor plan, vaulted ceilings, and a bright, inviting atmosphere. The kitchen is a standout, featuring quartz countertops, stainless-steel appliances, 42-inch shaker-style cabinetry, and a spacious L-shaped breakfast bar perfect for everyday meals or entertaining. The primary suite offers a walk-in closet and comfortable retreat, while additional features include an interior laundry area, whole-home water softener, and a 2-car garage. Conveniently located near shopping, dining, schools, recreation, and everything Winter Haven has to offer. Don’t miss the opportunity to make this beautiful home yours—schedule your private showing today!

276 Arbuthnot Street, Winter Haven

2758 Adeline Avenue, Winter Haven

2758 Adeline Avenue, Winter Haven

5 Beds ⋅ 2 Baths ⋅ Willowbrook South SubDv. ⋅ 33881 Zip Code

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 between three thoughtfully designed exterior styles. This spacious 5-bedroom, 2-bathroom home offers 1,708 square feet of modern, comfortable living. Step inside to an inviting open-concept layout where the kitchen, living, and dining areas flow seamlessly together perfect for both everyday living and entertaining guests. The gourmet kitchen is the heart of the home, featuring sleek stainless-steel appliances, quartz countertops, and contemporary cabinetry that combine style with functionality. Overlooking the dining and living room, the kitchen ensures you’re always connected to the action. Luxury finishes are found throughout, with luxury vinyl plank flooring in the main living areas, primary suite, bathrooms, laundry room, and foyer. Bedrooms 2–5 include soft carpet and roomy closets, offering comfort and flexibility to use as bedrooms, office space, or creative bonus rooms. The private primary suite is designed for relaxation, with a walk-in closet and an en-suite bathroom that includes a toilet and shower for added privacy. This move-in ready home in Willowbrook South, Florida offers the perfect balance of style, comfort, and convenience. *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.*

2758 Adeline Avenue, Winter Haven

827 Avenue O Sw, Winter Haven

827 Avenue O Sw, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code

Welcome to this beautifully remodeled Winter Haven home with a desirable Lake Shipp view! Thoughtfully updated from top to bottom, this property offers the peace of mind of a new roof, new HVAC system, updated plumbing, and updated electrical—giving you the feel of a brand-new home without the new-construction wait. Inside, enjoy a fresh, modern living space with quality updates and an inviting layout designed for comfortable everyday living and entertaining. The Lake Shipp views add a special touch, creating a relaxing backdrop to your Florida lifestyle. With major systems already updated, this home is an excellent opportunity for buyers looking for a move-in-ready property with substantial improvements already completed. Conveniently located in Winter Haven with easy access to area shopping, dining, recreation, and Central Florida attractions.

827 Avenue O Sw, Winter Haven

4035 Carteret Drive, Winter Haven

4035 Carteret Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code

Welcome to 4035 Carteret Drive, located in the gated 55+ community of Traditions at Lake Ruby. This spacious 2-bedroom, 2-bath home offers approximately 1,719 square feet of single-story living plus a versatile office/den and enclosed sunroom. The open floor plan provides comfortable living and entertaining space, while the attached two-car garage offers convenient parking and storage. Enjoy low-maintenance living with an HOA that provides community services including lawn care, cable and internet. Traditions offers an impressive collection of amenities including a lakefront clubhouse, heated pool and spa, fitness center, tennis and pickleball courts, bocce ball, shuffleboard, dog park, boat ramp, dock and access to Lake Ruby.

4035 Carteret Drive, Winter Haven

3877 Avenue O Nw, Winter Haven

3877 Avenue O Nw, Winter Haven

3 Beds ⋅ 2 Baths ⋅ 33880 Zip Code

Under Construction. This newly constructed home offers a comfortable and inviting layout with 3 bedrooms, 2 bathrooms, and 1,286 square feet of living space. From the moment you step inside, you’ll find a spacious and functional design with thoughtful details throughout. A rare opportunity awaits with the neighboring newly constructed home also available for purchase! Whether you’re looking to create a private family compound, live next door to parents, grandparents, or siblings, or simply have your best friends as neighbors, this unique opportunity offers endless possibilities while allowing everyone to enjoy the comfort and privacy of their own beautiful home. The foyer opens into the spacious dining and great rooms, with raised ceilings throughout creating an open and airy feel. The living space also provides convenient access to the outdoor patio, making it easy to enjoy the outdoors or entertain guests. The kitchen features a large island and plenty of storage, including a pantry, while the home also offers a primary walk-in closet, linen closet, and coat closet for added convenience. The 2-car garage provides additional storage and a dedicated laundry area. With no HOA, there’s also plenty of flexibility for your boat, RV, or other outdoor vehicles. With its new construction, comfortable layout, ample storage, and unique neighboring-home opportunity, this property is ready to welcome its new owners.

3877 Avenue O Nw, Winter Haven

3406 Fox Ridge Street, Winter Haven

3406 Fox Ridge Street, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Fox Ridge Ph 02 SubDv. ⋅ 33884 Zip Code

A hidden gem awaits for you in Fox Ridge in Winter Haven. This 3 bedroom 2 bath with 2 car garage has a lot to show. New roof 2026, new water heater and AC 2024. Installed also in 2026 Kitchen and bathroom cabinetry, counter tops and lighting fixtures. Open floor plan with cathedral ceilings and split bedrooms and with natural lighting streaming throughout the house. Kitchen has new farmer's sink , gas range and refrigerator. Laminate plank flooring thru out the house and tile on the master bedroom. A decorative fireplace sits in the living room. Master bedroom has a sliding door that opens to the large screened covered patio overlooking the fenced backyard. Master bathroom has a walk in shower and two walk in closets. All bedrooms have ceiling fans. No HOA. The patio would be a great place for entertaining.Great location with easy commute to shopping, dining, restaurants and downtown Winter Haven.

3406 Fox Ridge Street, Winter Haven

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