New Listings for Sale in Winter Haven, FL

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NEW 1 HR AGO

ABOUT THIS HOME
New Listing for sale in Winter Haven, FL:
Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading t

$350,000

5 beds2 baths2,078 sq ft

112 Paine Dr, Winter Haven, FL 33884

Highway 27 • Spacious 5-bedroom • Medical facilities

NEW 1 HR AGO

ABOUT THIS HOME
New Listing for sale in Winter Haven, FL:
This expansive two-story home boasts a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage.

$280,000

4 beds2.5 baths1,880 sq ft

2114 Chris Dr, Winter Haven, FL 33884

Serene owner's suite • Open concept design • Spacious loft

Listing provided by Zillow

NEW 14 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winter Haven, FL:
Experience refined living in this move-in ready 4-bedroom, 2-bath single-family estate built in 2019 and perfectly situated on Winter Haven’s Chain of Lakes. NO HOA. Upon entering you are greeted by a spacious foyer, soaring vaulted ceilings, a chef’s dream kitchen with premium stainless appliances. The kitchen is equipped with cabinets galore and plenty of counter space, including a large pantry. A formal dining area for those Holiday gatherings, and an expansive family room filled with natural light. The split floor plan ensures privacy with a serene primary suite featuring a spa-inspired en-suite with soaking tub and walk-in shower, double vanity split by a built-in make-up

$280,000

4 beds2 baths1,824 sq ft

160 Polk Dr SE, Winter Haven, FL 33884

Move-in ready • Cabinets galore • Chef's dream kitchen

NEW 14 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winter Haven, FL:
Located in Winter Haven off Cypress Garden. 1 bed 1 bath condo with new ac and new appliances. Unit is the first floor and has a private lanai and inside laundry room with full size washer/ dryer. Additional space can also be used as an office. Pet friendly!! Can come furnished. Community has a pool and dock on lake Lulu for fishing. Dedicated parking space and trash is included in the HOA. Walking to all shopping.

$135,000

1 bed1 bath975 sq ft

2001 San Marcos Dr SE #3, Winter Haven, FL 33880

Community has a pool • Inside laundry room • Private lanai

NEW 17 HRS AGO

ABOUT THIS HOME
New Listing for sale in Winter Haven, FL:
Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces—ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors

$880,000

9 beds6.5 baths5,700 sq ft

906 Lake Jessie Dr, Winter Haven, FL 33881

Private oasis • Modern finishes • Fire pit

Property at 110 Duval Rd, Winter Haven, FL 33884, 2 beds, 2 baths

$279,000

2 beds2 baths1,512 sq ft

110 Duval Rd, Winter Haven, FL 33884

Property at 103 Lake Hazel Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$130,000

2 beds2 baths1,316 sq ft

103 Lake Hazel Dr, Winter Haven, FL 33884

Property at 1788 Carnostie Rd, Winter Haven, FL 33884, 3 beds, 2 baths

$310,000

3 beds2 baths1,280 sq ft

1788 Carnostie Rd, Winter Haven, FL 33884

Property at 109 Rebecca Dr NE, Winter Haven, FL 33881, 3 beds, 2 baths

$239,500

3 beds2 baths1,560 sq ft

109 Rebecca Dr NE, Winter Haven, FL 33881

Property at 5850 Cypress Gardens Blvd #405, Winter Haven, FL 33884, 2 beds, 1.5 baths

$148,800

2 beds1.5 baths1,332 sq ft

5850 Cypress Gardens Blvd #405, Winter Haven, FL 33884

Property at 716 Santa Maria Dr, Winter Haven, FL 33884, 3 beds, 2 baths

$425,000

3 beds2 baths2,378 sq ft

716 Santa Maria Dr, Winter Haven, FL 33884

Property at 1516 Avenue D NE, Winter Haven, FL 33881, 3 beds, 2 baths

$290,000

3 beds2 baths1,089 sq ft

1516 Avenue D NE, Winter Haven, FL 33881

Property at 271 Inman Blvd, Winter Haven, FL 33881, 5 beds, 2.5 baths

$350,000

5 beds2.5 baths2,274 sq ft

271 Inman Blvd, Winter Haven, FL 33881

Property at Undisclosed address, Winter Haven, FL 33880, 2 beds, 2 baths

$99,900

2 beds2 baths720 sq ft

Undisclosed address, Winter Haven, FL 33880

Property at 3818 Avenue R NW, Winter Haven, FL 33881, 3 beds, 2 baths

$139,900

3 beds2 baths640 sq ft

3818 Avenue R NW, Winter Haven, FL 33881

Property at 937 Avenue L SE, Winter Haven, FL 33880, 4 beds, 5 baths

$424,900

4 beds5 baths2,368 sq ft

937 Avenue L SE, Winter Haven, FL 33880

Property at 3820 Traditions Blvd N, Winter Haven, FL 33884, 3 beds, 2 baths

$389,000

3 beds2 baths2,400 sq ft

3820 Traditions Blvd N, Winter Haven, FL 33884

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 5848 Windridge Dr, Winter Haven, FL 33881, 4 beds, 3.5 baths

$5,000

4 beds3.5 baths3,062 sq ft

5848 Windridge Dr, Winter Haven, FL 33881

Property at 373 Lake Daisy Cir, Winter Haven, FL 33884, 3 beds, 2 baths

$225,000

3 beds2 baths1,391 sq ft

373 Lake Daisy Cir, Winter Haven, FL 33884

Property at 20 Bridgewater Dr, Winter Haven, FL 33884, 3 beds, 2 baths

$472,500

3 beds2 baths2,434 sq ft

20 Bridgewater Dr, Winter Haven, FL 33884

Property at 4025 Oak Preserve Dr, Winter Haven, FL 33880, 4 beds, 2 baths

$339,000

4 beds2 baths2,038 sq ft

4025 Oak Preserve Dr, Winter Haven, FL 33880

Property at 1730 2nd St NW Unit A, Winter Haven, FL 33881, 6 beds, 3 baths

$380,000

6 beds3 baths2,496 sq ft

1730 2nd St NW Unit A, Winter Haven, FL 33881

Property at 1724 2nd St NW Unit D, Winter Haven, FL 33881, 6 beds, 3 baths

$450,000

6 beds3 baths2,496 sq ft

1724 2nd St NW Unit D, Winter Haven, FL 33881

Property at 3121 Avenue M NW, Winter Haven, FL 33881, 2 beds, 1 bath

$220,000

2 beds1 bath1,208 sq ft

3121 Avenue M NW, Winter Haven, FL 33881

Property at 4462 Emerald Palms Ln, Winter Haven, FL 33884, 4 beds, 3 baths

$825,000

4 beds3 baths2,825 sq ft

4462 Emerald Palms Ln, Winter Haven, FL 33884

Property at 900 Avenue Z SE Unit A203, Winter Haven, FL 33880, 2 beds, 1 bath

$135,000

2 beds1 bath840 sq ft

900 Avenue Z SE Unit A203, Winter Haven, FL 33880

Property at 72 Coleman Rd, Winter Haven, FL 33880, 3 beds, 2 baths

$295,000

3 beds2 baths2,028 sq ft

72 Coleman Rd, Winter Haven, FL 33880

Property at 3923 Warbler Dr, Winter Haven, FL 33880, 4 beds, 3 baths

$285,000

4 beds3 baths2,101 sq ft

3923 Warbler Dr, Winter Haven, FL 33880

Property at 3510 Majesty Loop, Winter Haven, FL 33880, 3 beds, 2 baths

$252,000

3 beds2 baths1,252 sq ft

3510 Majesty Loop, Winter Haven, FL 33880

Property at 4310 Shadow Wood Trl, Winter Haven, FL 33880, 3 beds, 4 baths

$643,000

3 beds4 baths3,051 sq ft

4310 Shadow Wood Trl, Winter Haven, FL 33880

Property at 29 Golf View Cir NE, Winter Haven, FL 33881, 4 beds, 3 baths

$400,000

4 beds3 baths2,228 sq ft

29 Golf View Cir NE, Winter Haven, FL 33881

Property at 4202 San Rocco Way, Winter Haven, FL 33884, 4 beds, 2 baths

$309,990

4 beds2 baths1,851 sq ft

4202 San Rocco Way, Winter Haven, FL 33884

Property at 3029 Country Club Cir, Winter Haven, FL 33881, 4 beds, 2 baths

$319,990

4 beds2 baths1,828 sq ft

3029 Country Club Cir, Winter Haven, FL 33881

Property at 130 Audubon Rd, Winter Haven, FL 33884, 4 beds, 2 baths

$347,900

4 beds2 baths2,503 sq ft

130 Audubon Rd, Winter Haven, FL 33884

Property at 1062 Medinah Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$199,995

2 beds2 baths1,398 sq ft

1062 Medinah Dr, Winter Haven, FL 33884

Property at 6756 Kensington Dr NE, Winter Haven, FL 33881, 2 beds, 2 baths

$138,000

2 beds2 baths1,232 sq ft

6756 Kensington Dr NE, Winter Haven, FL 33881

Property at 616 Kings Ln SW, Winter Haven, FL 33880, 3 beds, 2 baths

$325,999

3 beds2 baths1,312 sq ft

616 Kings Ln SW, Winter Haven, FL 33880

Property at 3349 Costello Cir, Winter Haven, FL 33884, 3 beds, 2 baths

$280,000

3 beds2 baths1,516 sq ft

3349 Costello Cir, Winter Haven, FL 33884

Property at 6165 Pebble Beach Blvd, Winter Haven, FL 33884, 3 beds, 2 baths

$469,000

3 beds2 baths2,045 sq ft

6165 Pebble Beach Blvd, Winter Haven, FL 33884

Property at 2512 Sherwood St, Winter Haven, FL 33881, 4 beds, 3 baths

$479,900

4 beds3 baths2,697 sq ft

2512 Sherwood St, Winter Haven, FL 33881

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Based on information submitted to the MLS GRID as of Sun Dec 07 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.

New Listings for Sale in Winter Haven

There are currently 97 new listings for sale in Winter Haven at a median listing price of $314K. 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 100 days and receive 1 offers. Popular neighborhoods include Rock Springs Ridge, Caribe Cove, Traditions, Lake Ashton, and Downtown Winter Haven. This map is refreshed with the newest listings in Winter Haven every 15 minutes.

In the past month, 72 homes have been sold in Winter Haven. In addition to houses in Winter Haven, there were also 47 condos, 22 townhouses, and 8 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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