Homes for sale under $300k in Winter Haven, FL

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ABOUT THIS HOME
Homes for sale under $300k in Winter Haven, FL
NEW ROOF already installed september 2025, however non functional electrical panel, non functional AC so only CASH and Private HARD MONEY is available for this home. New Roof & Great Structure. With some upgrades and TLC the possibilities are endless as the enclosed carport can be expanded for additional 2 bedrooms to bring to a total 5 bedroom home Rental or for a Large Family to Enjoy. View of Lake from Street View of Curb. Quaint Community with pride of ownership.

$220,000

3 beds3 baths1,426 sq ft

1858 4th St SE, Winter Haven, FL 33880

0.25 acre lot • Built 1960 • Listed 54 days

ABOUT THIS HOME
Homes for sale under $300k in Winter Haven, FL
SELLER PAID 2-1 TEMPORARY INTEREST RATE BUYDOWN AVAILABLE - See attachment for monthly payment details with preferred lender. Welcome to this newly renovated 3-bedroom, 1-bath home conveniently located near Lake Cannon and just minutes from all the dining, shopping, and entertainment that Winter Haven and Auburndale have to offer! Step through the front door to find fresh interior paint, new carpet in all bedrooms, and inviting living spaces. The kitchen has been refreshed with brand-new appliances, provides plenty of cabinetry storage and counter space, and has a convenient layout for everyday cooking and entertaining. The bathroom is your own personal retreat featuring a new vanity and a

$219,950

3 beds1 bath1,129 sq ft

1115 29th St NW, Winter Haven, FL 33881

New carpet • Fresh interior paint • Brand-new appliances

ABOUT THIS HOME
Homes for sale under $300k in Winter Haven, FL
Cute as a button. Great starter home or investment property. Large corner lot. Featuring NEW ROOF, NEW SEPTIC, NEW ELECTRICAL PANELS. This three bedrooms one & one half bathroom has a new modern eat in kitchen and laminate floors. Open spacious living and dining room. Covered front porch. Why rent just buy. Adjoining vacant lot is not included in the sale and has been removed from the legal description. Lot maybe purchased separately.

$219,900

3 beds1.5 baths1,166 sq ft

1997 26th St NW, Winter Haven, FL 33881

Laminate floors • Large corner lot • New septic

ABOUT THIS HOME
Homes for sale under $300k in Winter Haven, FL
1 OWNER HOME!! Don't miss out on this 2 bed 2 bath tennis villa in the highly desired neighborhood of Cypresswood. The HOA takes care of the roof, lawn, paint, and exterior maintenance. Enjoy the security of living in a community with a 24 hour guard at the gate. There is plenty to do all within the community. There is a golf course, restaurant, community pool and tennis courts. The home has all new flooring, paint, and granite counter tops. Make your appointment TODAY!!

$219,900

2 beds2 baths1,278 sq ft

1039 Medinah Dr, Winter Haven, FL 33884

Community pool • 24 hour guard • New flooring

ABOUT THIS HOME
Homes for sale under $300k in Winter Haven, FL
GREAT OPPORTUNITY!!! Totally TURNKEY with all NEW FURNISHINGS!!! Welcome to carefree living in this bright, airy super clean end unit villa. 1524 sq. ft. with 2 bedrooms, 2 bathrooms and a flex room for den, guests or office. The modern kitchen boasts tall cabinets with crown molding, quartz countertops and smudge proof stainless appliances and a pantry. Ceilings are high with crown molding for an open feel. The master has a large walk-in shower, dual vanities and large walk-in closet. New Wi-Fi thermostat and A/C blower upgrade in July, tuned for optimal efficiency. No worries, low cost insurance as HOA covers the roof, the exterior, and also the landscaping, painting, irrigation, expansiv

$219,900

2 beds2 baths1,521 sq ft

3020 Caneel St, Winter Haven, FL 33884

Dual vanities • End unit • Walk-in closet

Property at 1822 Nicaragua Way, Winter Haven, FL 33881, 2 beds, 2 baths

$219,500

2 beds2 baths1,165 sq ft

1822 Nicaragua Way, Winter Haven, FL 33881

Property at 312 Donald Ln, Winter Haven, FL 33880, 2 beds, 2 baths

$219,000

2 beds2 baths840 sq ft

312 Donald Ln, Winter Haven, FL 33880

Property at 4488 Turnberry Ln, Lake Wales, FL 33859, 2 beds, 2 baths

$217,500

2 beds2 baths1,083 sq ft

4488 Turnberry Ln, Lake Wales, FL 33859

Property at 3715 Avenue J NW, Winter Haven, FL 33881, 3 beds, 1.5 baths

$217,000

3 beds1.5 baths892 sq ft

3715 Avenue J NW, Winter Haven, FL 33881

Property at 411 Avenue A SE, Winter Haven, FL 33880, 2 beds, 1 bath

$215,000

2 beds1 bath1,240 sq ft

411 Avenue A SE, Winter Haven, FL 33880

Property at 2270 Firestone Pl, Winter Haven, FL 33884, 2 beds, 2 baths

$215,000

2 beds2 baths1,439 sq ft

2270 Firestone Pl, Winter Haven, FL 33884

Property at 203 Summer View Dr, Winter Haven, FL 33880, 3 beds, 1 bath

$215,000

3 beds1 bath993 sq ft

203 Summer View Dr, Winter Haven, FL 33880

Property at 2853 Attwater Loop, Winter Haven, FL 33884, 2 beds, 2 baths

$215,000

2 beds2 baths1,385 sq ft

2853 Attwater Loop, Winter Haven, FL 33884

Property at 1584 Vienna Square Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$215,000

2 beds2 baths1,231 sq ft

1584 Vienna Square Dr, Winter Haven, FL 33884

Property at 683 Broadmoor Cir #683, Winter Haven, FL 33884, 2 beds, 2 baths

$215,000

2 beds2 baths1,139 sq ft

683 Broadmoor Cir #683, Winter Haven, FL 33884

Property at 2877 Attwater Loop, Winter Haven, FL 33884, 2 beds, 2 baths

$215,000

2 beds2 baths1,385 sq ft

2877 Attwater Loop, Winter Haven, FL 33884

Property at 6388 Lolly Bay Loop NE, Winter Haven, FL 33881, 3 beds, 2 baths

$212,500

3 beds2 baths1,548 sq ft

6388 Lolly Bay Loop NE, Winter Haven, FL 33881

Property at 503 Holt Cir, Winter Haven, FL 33880, 3 beds, 2 baths

$210,000

3 beds2 baths1,305 sq ft

503 Holt Cir, Winter Haven, FL 33880

Property at 6346 Bayberry Blvd NE, Winter Haven, FL 33881, 2 beds, 2 baths

$210,000

2 beds2 baths1,440 sq ft

6346 Bayberry Blvd NE, Winter Haven, FL 33881

Property at 2352 Isle Royale Ct SE, Winter Haven, FL 33880, 2 beds, 2.5 baths

$210,000

2 beds2.5 baths1,281 sq ft

2352 Isle Royale Ct SE, Winter Haven, FL 33880

Property at 341 Avenue L NE, Winter Haven, FL 33881, 3 beds, 1 bath

$210,000

3 beds1 bath1,188 sq ft

341 Avenue L NE, Winter Haven, FL 33881

Property at 240 Lake Thomas Dr, Winter Haven, FL 33880, 3 beds, 2 baths

$210,000

3 beds2 baths1,223 sq ft

240 Lake Thomas Dr, Winter Haven, FL 33880

Property at 3115 Avenue U NW, Winter Haven, FL 33881, 3 beds, 1 bath

$210,000

3 beds1 bath988 sq ft

3115 Avenue U NW, Winter Haven, FL 33881

Property at 1213 NW 8th, Winter Haven, FL 33881, 2 beds, 2 baths

$210,000

2 beds2 baths972 sq ft

1213 NW 8th, Winter Haven, FL 33881

Property at 1328 3rd St NE, Winter Haven, FL 33881, 3 beds, 2 baths

$210,000

3 beds2 baths1,196 sq ft

1328 3rd St NE, Winter Haven, FL 33881

Property at 436 Avenue G SE, Winter Haven, FL 33880, 2 beds, 2.5 baths

$210,000

2 beds2.5 baths1,309 sq ft

436 Avenue G SE, Winter Haven, FL 33880

Property at 769 Avenue Q SE, Winter Haven, FL 33880, 2 beds, 1.5 baths

$209,999

2 beds1.5 baths960 sq ft

769 Avenue Q SE, Winter Haven, FL 33880

Property at 6239 Knotty Pine Dr SE, Winter Haven, FL 33884, 2 beds, 2 baths

$209,900

2 beds2 baths1,367 sq ft

6239 Knotty Pine Dr SE, Winter Haven, FL 33884

Property at 506 Sweet Bay Cir #506, Winter Haven, FL 33884, 2 beds, 2 baths

$209,900

2 beds2 baths1,090 sq ft

506 Sweet Bay Cir #506, Winter Haven, FL 33884

Property at 710 Byni Rdg, Winter Haven, FL 33880, 3 beds, 2 baths

$209,000

3 beds2 baths1,056 sq ft

710 Byni Rdg, Winter Haven, FL 33880

Property at 6107 Grand Oaks Dr SE, Winter Haven, FL 33884, 2 beds, 2 baths

$209,000

2 beds2 baths1,340 sq ft

6107 Grand Oaks Dr SE, Winter Haven, FL 33884

Property at 2203 Starboard, Winter Haven, FL 33881, 2 beds, 2 baths

$209,000

2 beds2 baths1,260 sq ft

2203 Starboard, Winter Haven, FL 33881

Property at 492 Lakeside Ranch Cir, Winter Haven, FL 33881, 2 beds, 2 baths

$208,000

2 beds2 baths1,620 sq ft

492 Lakeside Ranch Cir, Winter Haven, FL 33881

Property at 2769 Attwater Loop, Winter Haven, FL 33884, 2 beds, 2 baths

$207,500

2 beds2 baths1,385 sq ft

2769 Attwater Loop, Winter Haven, FL 33884

Property at 3931 Avenue R NW, Winter Haven, FL 33881, 3 beds, 2 baths

$206,900

3 beds2 baths928 sq ft

3931 Avenue R NW, Winter Haven, FL 33881

Property at 1224 Vienna Square Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$205,000

2 beds2 baths1,118 sq ft

1224 Vienna Square Dr, Winter Haven, FL 33884

Property at 6314 Bayberry Blvd NE, Winter Haven, FL 33881, 2 beds, 2 baths

$205,000

2 beds2 baths1,638 sq ft

6314 Bayberry Blvd NE, Winter Haven, FL 33881

Property at 1101 28th St NW, Winter Haven, FL 33881, 3 beds, 2 baths

$204,999

3 beds2 baths968 sq ft

1101 28th St NW, Winter Haven, FL 33881

Property at 226 4th St NE, Winter Haven, FL 33881, 3 beds, 1 bath

$204,700

3 beds1 bath1,438 sq ft

226 4th St NE, Winter Haven, FL 33881

Property at 1012 Medinah Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$203,000

2 beds2 baths1,458 sq ft

1012 Medinah Dr, Winter Haven, FL 33884

Property at 1606 Eagle Pond Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$200,000

2 beds2 baths1,017 sq ft

1606 Eagle Pond Dr, Winter Haven, FL 33884

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Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes for sale under $300k in Winter Haven

There are currently 487 homes for sale under $300k in Winter Haven. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Haven stay on the market for 91 days and receive 1 offers. Popular neighborhoods include Rock Springs Ridge, Traditions, Lake Ashton, Downtown Winter Haven, and Lake Ashton Golf Club. This map is refreshed with the newest listings in Winter Haven every 15 minutes.

In the past month, 105 homes have been sold in Winter Haven. In addition to houses in Winter Haven, there were also 49 condos, 24 townhouses, and 10 multi-family units for sale in Winter Haven last month. Winter Haven is a minimally walkable city in Polk County with a Walk Score of 25. Winter Haven is home to approximately 34,907 people and 22,420 jobs. Find your dream home in Winter Haven using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Haven are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Haven. Our Winter Haven real estate stats and trends will give you more information about home buying and selling trends in Winter Haven. If you're looking to sell your home in the Winter Haven area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Haven with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Homes for sale under $300k in Winter Haven, FL

Homes for sale under $300k in Winter Haven

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