Winter Haven Homes under $500,000

Winter Haven Homes under $500,000

Welcome to Winter Haven, Florida—a vibrant city nestled in the heart of Polk County, renowned for its stunning lakes, lush landscapes, and a warm, inviting community. Known as the “Chain of Lakes” city, Winter Haven boasts over 50 lakes, offering endless opportunities for water activities, from fishing and boating to kayaking and paddleboarding. This charming locale is not just about scenic beauty; it’s a place where families thrive, and friendships flourish.

Winter Haven’s rich history is reflected in its charming downtown area, where you can explore a variety of local shops, delightful cafes, and cultural attractions, including the famous Legoland Florida Resort. With a mild climate year-round, residents enjoy an active outdoor lifestyle, with parks and recreational facilities at every turn, making it an ideal setting for families and retirees alike.

For those seeking a home in Winter Haven, you’ll be pleased to discover a diverse selection of properties available for under $500,000. Whether you’re looking for a cozy single-family home, a modern townhouse, or a spacious waterfront property, Winter Haven offers something for everyone. The real estate market here is not only affordable but also thriving, making it an excellent investment opportunity.

Imagine waking up to the tranquil sounds of nature, enjoying a morning coffee with a lake view, or hosting weekend barbecues in your backyard. In Winter Haven, you can turn these dreams into reality without breaking the bank. Come explore the possibilities and find your perfect home in this enchanting city!

Newest Winter Haven Homes under $500,000

104 13th Street Se, Winter Haven
$200,000
2 Beds ⋅ 2 Baths ⋅ Elbert Hills SubDv. ⋅ 33880 Zip Code
Investor's dream or handyman special with plenty of potential! This 2-bedroom, 2-bath home offers 1,776 square feet of living space, including a bonus room with a bathroom. Enjoy a spacious 15-by-24 foot screened back porch, and an above-ground pool, and a view of Lake Elbert from the front driveway. With a little TLC, this property is ready to make your own or unlock its investment potential in desirable area of Winter Haven.

104 13th Street Se, Winter Haven
1841 5th Street Se, Winter Haven
$339,000
3 Beds ⋅ 2 Baths ⋅ Southeast Terrace SubDv. ⋅ 33880 Zip Code
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 space with a combination of practical upgrades, comfortable indoor living, and versatile outdoor space. One of the standout advantages is NO HOA, offering added ownership flexibility for buyers and investors alike. Whether you're searching for a primary residence, second home, or potential long-term rental addition to your portfolio, this property presents an appealing opportunity, subject to applicable rental and local regulations. Several important improvements have already been completed, including a roof replaced in 2026, irrigation updated approximately three months ago, a water heater approximately four years old, newer carpeting, double-pane windows, and an updated faucet. The home also offers natural gas, a reverse-osmosis water system, security system, generous closets, and cable access in each room. The second bathroom features double vanities, and the bathroom vanities were updated approximately five years ago. The garage features an epoxy-coated floor, adding a clean, finished touch to this functional space. Outdoors, you'll find a fully fenced backyard, established back and side-yard pathways approximately four years old, a dry storage shed with electricity, and a newer driveway retaining wall providing useful space for pets, gardening, entertaining, storage, hobbies, and everyday outdoor living. Beyond the property, enjoy the lifestyle and convenience that make Winter Haven and Central Florida an attractive place to call home. Nearby recreation includes South Central Park, Trailhead Park Playground, Rotary Park, Lake Shipp Park, and South Lake Howard Nature Park. Family entertainment and attractions include LEGOLAND® Florida Resort, PEPPA PIG Theme Park Florida, Planet Obstacle, and Cowboy Adventure Park.Discover local dining favorites such as Harborside, Harry's Old Place, Bowen Yard, and Lucille's American Cafe, along with convenient access to healthcare services including Winter Haven Hospital, AdventHealth emergency care, and BayCare Urgent Care. With its combination of recent improvements, outdoor functionality, location, and ownership flexibility, 1841 5th Street SE offers an opportunity worth exploring for homeowners and investment-minded buyers. Schedule your private showing today!

1841 5th Street Se, Winter Haven
842 Avenue N Sw, Winter Haven
$175,000
3 Beds ⋅ 1 Baths ⋅ Lake Shipp Or Porters Add SubDv. ⋅ 33880 Zip Code
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 investor a predictable return from the day they close. Inside, you'll find an updated kitchen, central AC, and a fireplace that adds character to the main living area. Outside, the property sits on a quarter acre lot with a screened front patio, a backyard deck, and a large fenced backyard, which makes the home appealing to future tenants and a future owner-occupant alike. The location is close to downtown Winter Haven, with dining, shopping, and the area's lakes nearby. Lease and rent history are available on request. Showings are by appointment only - see remarks.

842 Avenue N Sw, Winter Haven
2825 Wingfoot Court, Winter Haven
$225,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Golf And Country Club SubDv. ⋅ 33884 Zip Code
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 the guard-gated Cypresswood Golf & Country Club, built in 1990. Vaulted ceilings open up the living and dining areas, while the updated kitchen offers generous cabinetry and flows into a bright dinette/oversized breakfast nook. Both the living room and dinette lead into a Florida room overlooking the fairway, the perfect spot to unwind. Windows and doors were replaced in 2024, with updated flooring throughout, plus a new A/C (2021) and roof (2019) for added peace of mind. HOA dues of $295/month cover resort-style amenities: 24-hour guarded gate, 18-hole championship golf course, community pool, tennis courts, and a newly added pickleball court (2025). Ideally located near US-27 with easy access to Orlando and Tampa. Don't miss this move-in-ready fairway retreat. Schedule your showing today

2825 Wingfoot Court, Winter Haven
575 Saint Andrews Road, Winter Haven
$286,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
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 Club, this beautifully maintained 2-bedroom, 2-bathroom golf-front home offers the perfect blend of active resort living and quiet tranquility. Imagine waking up, stepping onto your private patio, and sipping your morning coffee while looking out over pristine, rolling fairway. What truly sets this home apart is that every major expense has already been taken care of for you. You can move in with absolute confidence, knowing you won't have to worry about costly upgrades or repairs for years to come. Recent premium updates include: •Brand New HVAC System (2024): Brand new inside and out for peak energy efficiency. •New Roof & Structural Updates (2022): Completely replaced roof, overhang, and facia boards. •Total Peace of Mind (2021): The entire home was fully re-plumbed. •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage •Modern Conveniences: Updated kitchen and bathroom fixtures, a new garage door opener, a new garbage disposal, and upgraded GFCI outlets. Storage is never an issue with the massive 23x23 oversized garage—offering ample space for your vehicles, workshop, and of course, your golf cart. Opportunities in Cypresswood like this do not last long. Don’t wait to start living your dream golf-course lifestyle—call today to schedule your private showing!

575 Saint Andrews Road, Winter Haven
10 W Lake Hamilton Circle, Winter Haven
$485,000
4 Beds ⋅ 2 Baths ⋅ Pollard Shores SubDv. ⋅ 33881 Zip Code
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. This inviting residence combines comfortable living spaces, thoughtful updates, mature landscaping, and an exceptional canalfront lifestyle with direct access to Lake Hamilton. Inside, the home features carpet and tile flooring throughout, updated HVAC, and new kitchen appliances. The spacious floor plan offers plenty of room for both everyday living and entertaining, including a dining room directly off the kitchen, a dedicated TV/activity room, and a centralized fireplace that creates a warm and welcoming focal point. The private primary suite offers a relaxing retreat with its own en-suite bathroom, while three additional bedrooms provide flexibility for guests, an office, or hobbies. Step outside and the property truly comes to life. The well-landscaped half-acre lot is surrounded by beautiful mature oak trees, creating shade, privacy, and a classic Florida setting. The large, deep swimming pool is complemented by a spacious lanai, making it an ideal place to relax, entertain, or enjoy sunny Florida afternoons. Beyond the pool, you'll find an incredible waterfront setup with a private dock, canal frontage, and a dedicated fireplace sitting area overlooking the water. And for boating enthusiasts, the location is especially appealing. Moor your boat right at your private back dock and enjoy direct boating access to Lake Hamilton. From there, it's approximately a three-minute boat ride to Port 27 and Floridinos, where patrons can tie their boats up at the restaurants' docks and arrive by water for dinner, drinks, or an evening out. With its combination of lake access, private dock, pool, mature landscaping, spacious lot, updated systems and appliances, and versatile interior living spaces, 10 West Lake Hamilton Circle offers the best of relaxed Florida living with the convenience of being able to enjoy Lake Hamilton right from your backyard.

10 W Lake Hamilton Circle, Winter Haven
5344 Nicklaus Drive, Winter Haven
$310,000
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
$249,950
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
$284,900
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
$289,900
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
$175,000
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
$285,000
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
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