Winter Haven, FL Homes

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  /20

  $195,000

  $54K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft

  1109 5th St SW, Winter Haven, FL 33880

  Short Sale. Discover the exceptional potential of this 3-bedroom, 2-bathroom home ideally located in the heart of Winter Haven, offering unbeatable access and flexibility with no HOA restrictions. Positioned just minutes from major highways, shopping centers, dining, and local amenities, this property delivers convenience that’s hard to match. Inside, the home features a spacious living area, an

  

  Carlos DeJesus

  EXIT REALTY 4CORNERS

  1109 5th St SW, Winter Haven, FL 33880
• 

  

  

  /15

  $1,900 Per Month

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  554 Reddicks Cir, Winter Haven, FL 33884

  Welcome to this inviting home located in a quiet neighborhood in Winter Haven! This well-maintained property features a spacious layout with comfortable living areas, perfect for relaxing or entertaining. The home offers multiple bedrooms and bathrooms, providing plenty of space for families or roommates.Conveniently located near shopping, dining, schools, and major roadways, this home

  554 Reddicks Cir, Winter Haven, FL 33884
• 

  

  /2

  $28,000

  Sold Jun 30, 2026

  839 Sears Ave NE, Winter Haven, FL 33881

  • Land
  • 4,791 Sq Ft
  • $254,545 per Acre

  Last Sold Summary

  • 38% Below List Price
  • 18 Days On Market

  Current Estimated Value $130,667

  Last Listing Agent Kalanda Scarvers SPANN & ASSOCIATES REAL ESTATE

  839 Sears Ave NE, Winter Haven, FL 33881
• 

  

  

  /56

  Est $263,480

  Not Listed For Sale

  6130 Grey Heron Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,698 Sq Ft
  • Built 2017

  6130 Grey Heron Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 75 Days On Market
• 

  

  

  /36

  $235,000

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft

  506 Thomas Ave, Winter Haven, FL 33880

  Discover the value you've been searching for! This affordably priced 4-bedroom, 2-bath home offers the space today's buyers need without stretching the budget. Inside, you'll find tile flooring throughout, a welcoming formal living room, plus a spacious family room just off the kitchen—perfect for everyday living and entertaining. The kitchen also features a dedicated dining area, creating a

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  506 Thomas Ave, Winter Haven, FL 33880
• 

  

  /19

  $1,425 Per Month

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft
  • Condo for Rent

  333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880

  FOR RENT - 2 Bedroom/2 Bath Condo at Imperial Harbours. This community is for ages 55+. The unit comes with all of the appliances and faces the garden area. The bedrooms are generously sized, and the porch area is enclosed. The community features a very nice pool with a TIKI Bar area for relaxing and sipping your favorite drinks. In the distance you can watch the sun rise over Lake Howard in the

  Linda Andre COLDWELL BANKER REALTY

  333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880
• 

  /2

  $370,000

  Sold Jan 02, 2026

  905 Hillside Ct S, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 2,077 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $178/SF
  • 27 Days On Market

  Current Estimated Value $368,101

  Last Listing Agent Tisha Talbot CENTURY 21 MYERS REALTY

  905 Hillside Ct S, Winter Haven, FL 33881
• 

  

  /16

  Est $219,213

  Not Listed For Sale

  108 4th St NE, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2023

  108 4th St NE, Winter Haven, FL 33881

  Last Sold Summary

  • 80 Days On Market
• 

  

  /36

  $319,999

  $14K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  718 Eagle Landing Blvd, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Built in 2023 and set on a premium homesite with no rear neighbors, this move-in-ready Winter Haven home offers four bedrooms, two-and-a-half bathrooms, a flexible open layout and peaceful views of the green space behind the property. Fresh interior paint, updated landscaping, new mulch and recent

  

  Micaela Navarra

  M2M REALTY

  718 Eagle Landing Blvd, Winter Haven, FL 33880
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  /4

  $2,450 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft
  • House for Rent

  1273 Zambrana Ct, Winter Haven, FL 33884

  Property Id: 2739644 Welcome to your dream home in the Villa Mar community. The property is located at 1273 Zambrana Ct in Winter haven, FL! This stunning 4-bed, 2 1/2bath single-family home is available starting 7/27/2026 for $2450 a month. Enjoy modern amenities, stainless steel appliances, granite countertops, vinyl flooring upstairs, and tile downstairs. There is a playground and

  1273 Zambrana Ct, Winter Haven, FL 33884
• 

  /2

  $301,805

  Sold Feb 25, 2026

  3861 Giorgio Dr, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $164/SF
  • 208 Days On Market

  Current Estimated Value $297,900

  Meritage Homes VillaMar - Signature Series

  3861 Giorgio Dr, Winter Haven, FL 33884
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  /2

  Not Listed For Sale

  208 Maple St, Winter Haven, FL 33880

  208 Maple St, Winter Haven, FL 33880

  Last Sold Summary

  • 0 Days On Market
• 

  

  /97

  $380,000

  $10K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft

  5137 Winged Foot Ln, Winter Haven, FL 33884

  Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this delightful, remarkably private, and fully updated 3-bedroom, 2-bath home awaits your arrival. To the west lies a forested nature preserve that circles to the north and then east, providing absolute privacy on two sides of the oversized lot and creating a serene,

  

  Brad Kirwan

  GLOBAL LIFESTYLE LLC

  5137 Winged Foot Ln, Winter Haven, FL 33884
• 

  

  /8

  $800 Per Month

  • 1 Bed
  • 1 Bath
  • 288 Sq Ft
  • House for Rent

  115 Avenue F SW Unit B, Winter Haven, FL 33880

  This brand-new studio apartment offers efficient, low-maintenance living with an open layout and vinyl flooring throughout. The space features a bright main living area/kitchen and a bathroom with a walk-in shower. With its fresh construction and easy-care design, the space maintains a straightforward, functional feel ideal for someone seeking a no-frills place to call home.

  Christin Davis PROPERTY MANAGEMENT OF POLK

  115 Avenue F SW Unit B, Winter Haven, FL 33880
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  /2

  $260,000

  Sold Dec 11, 2025

  1032 Cambridge Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 2021

  Last Sold Summary

  • 863% Above List Price
  • $173/SF
  • 57 Days On Market

  Current Estimated Value $255,335

  Last Listing Agent Fredy Plazas FLORIDA REALTY INVESTMENTS

  1032 Cambridge Dr, Winter Haven, FL 33881
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  /2

  Not Listed For Sale

  30 Flamingo Blvd, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1976

  30 Flamingo Blvd, Winter Haven, FL 33880

  Last Sold Summary

  • 28 Days On Market
• 

  

  /51

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,998 Sq Ft

  4111 Island Lakes Dr, Winter Haven, FL 33881

  Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the

  

  Amy Moline

  EXP REALTY LLC

  4111 Island Lakes Dr, Winter Haven, FL 33881
• 

  /2

  $1,595 Per Month

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • House for Rent

  876 Crestwood Dr, Winter Haven, FL 33881

  This home located in a quiet and desirable area of Winter Haven. This well-maintained property offers a comfortable layout with plenty of natural light, creating a warm and inviting living space.The home features spacious bedrooms, a cozy living area, and a functional kitchen with ample cabinet space, perfect for everyday living. The property also includes a nice outdoor area, ideal for

  876 Crestwood Dr, Winter Haven, FL 33881
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  /2

  $269,000

  Sold Sep 30, 2025

  122 Majestic Gardens Ct, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,688 Sq Ft
  • Built 2012

  Last Sold Summary

  • $159/SF
  • 6 Days On Market

  Current Estimated Value $275,374

  Last Listing Agent Corinna Weaver CROSBY & ASSOCIATES, INC.

  122 Majestic Gardens Ct, Winter Haven, FL 33880
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  /43

  Not Listed For Sale

  235 6th St NW Unit 207, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 857 Sq Ft
  • Built 1982

  235 6th St NW Unit 207, Winter Haven, FL 33881

  Last Sold Summary

  • 97 Days On Market
• 

  

  /5

  $980,000

  $130K PRICE INCREASE

  • Land
  • 9.8 Acres
  • $100,000 per Acre

  0 Brigham Rd NW, Winter Haven, FL 33881

  9.8 ACRES (8.5 acres of R-3 + 1.3 acres of Conservation zoning) in the City of Winter Haven. Prime location and already zoned for multifamily development (R-3). Additional unit count with potential zoning change of 1.3 acre portion to R-3. WATER, SEWER & POWER readily available! Property fronts onto Brigham Road and backs up to a Conservation Area. All measurements including acreage count are

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  0 Brigham Rd NW, Winter Haven, FL 33881
• 

  

  /11

  $1,150 Per Month

  • 2 Beds
  • 1 Bath
  • 468 Sq Ft
  • Apartment for Rent

  514 Avenue C NE Unit 4, Winter Haven, FL 33881

  Fantastic 2 bedroom/1.0 bathroom apartment totally renovated and ready for its new occupants. Unit is in close proximity of schools, including Jewett School of the Arts, Fred G. Garner Elementary School, and Frank E. Brigham Academy. 2 minute walk to Rotary Park. 7 minute walk to Kiwanis Park. 14 minute walk to Winter Haven Tennis Center. Water is included in the rent.

  Angela Chapman CAPITAL REALTY GROUP FLORIDA

  514 Avenue C NE Unit 4, Winter Haven, FL 33881
• 

  /2

  $65,000

  Sold Mar 20, 2026

  200 El Camino Dr Unit 203, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,378 Sq Ft
  • Built 1971

  Last Sold Summary

  • 34% Below List Price
  • $47/SF
  • 20 Days On Market

  Current Estimated Value $83,333

  Last Listing Agent Christina Ashley DALTON WADE INC

  200 El Camino Dr Unit 203, Winter Haven, FL 33884
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  /2

  Est $279,367

  Not Listed For Sale

  441 Squires Grove Dr, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 1,846 Sq Ft
  • Built 2018

  441 Squires Grove Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 50 Days On Market
• 

  

  /34

  $195,000

  $6K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft

  921 Avenue E NE, Winter Haven, FL 33881

  NEW ROOF installed last week! Situated on a spacious 75' x 124' fully fenced lot in Winter Haven, this property offers the freedom and flexibility that's becoming increasingly difficult to find. With no HOA restrictions, you'll have room to park your boat, trailer, recreational vehicles, and outdoor equipment right on your own property. The oversized 12' x 28' garage is ideal for a workshop or

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  921 Avenue E NE, Winter Haven, FL 33881
• 

  

  /13

  $1,045 Per Month

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Condo for Rent

  3039 St Paul Dr, Jan Phyl Village, FL 33880

  Beautiful 2-bedroom unit off of Winter Lake Rd in Winter Haven is move-in ready! Enjoy the vaulted ceiling and exposed beams in the living room. Kitchen features include breakfast bar, granite counters, & custom cabinets. Washer/dryer hookups and lawn care for stress-free living. Up to 2 small pets welcome-30 lbs. or less. Schedule your showing today!Applications do not hold the property

  3039 St Paul Dr, Jan Phyl Village, FL 33880
• 

  

  /15

  $295,990

  Sold Jun 24, 2026

  6337 Botticella Blvd, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 2,370 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • 11% Below List Price
  • $125/SF
  • 36 Days On Market

  Current Estimated Value $328,773

  6337 Botticella Blvd, Winter Haven, FL 33884
• 

  

  /36

  Est $319,681

  Not Listed For Sale

  6087 Grey Heron Dr, Winter Haven, FL 33881

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft
  • Built 2017

  6087 Grey Heron Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 289 Days On Market
• 

  

  /32

  $137,500

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  435 Village Cir SW, Winter Haven, FL 33880

  Under contract-accepting backup offers. ENJOY FLORIDA LIVING AS IT'S FINEST...Welcome yourself home to this 2 Bedroom/ 2 Bath home offering over 1,300 sq ft of comfortable living space and with valuable upgrades, including True Hardwood Floors in the Living Room, Hall and Bedrooms, NEW ROOF 2026 and Newer A/C 2020. Relax and unwind in the large Florida room in the front or the screened-in lanai

  

  Cheryl Brewer

  COLDWELL BANKER REALTY

  435 Village Cir SW, Winter Haven, FL 33880
• 

  

  /42

  $1,450 Per Month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Condo for Rent

  704 Eagle Pond Dr Unit 7D, Winter Haven, FL 33884

  Lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club. 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas, including a kitchen breakfast bar. All NEW luxury vinyl flooring, NEW windows and sliding glass patio door, NEW kitchen countertops, and fresh interior paint.

  Kayly Malinas JOHN WOOD REALTY, INC.

  704 Eagle Pond Dr Unit 7D, Winter Haven, FL 33884
• 

  /2

  $525,000

  Sold Sep 04, 2025

  6112 Pebble Beach Blvd, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 2,535 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $207/SF
  • 9 Days On Market

  Current Estimated Value $523,656

  Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

  6112 Pebble Beach Blvd, Winter Haven, FL 33884
• 

  

  /25

  Not Listed For Sale

  3000 Thornhill Rd, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1999

  3000 Thornhill Rd, Winter Haven, FL 33880

  Last Sold Summary

  • 50 Days On Market
• 

  

  /25

  $319,499

  New Construction $21K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,038 Sq Ft

  5460 San Pietro Dr, Winter Haven, FL 33884

  The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and

  

  Casa Fresca Homes

  Builder

  5460 San Pietro Dr, Winter Haven, FL 33884
• 

  

  /15

  $1,855 Per Month

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • House for Rent

  175 Southern Breeze Lp, Winter Haven, FL 33880

  From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. Apply now or schedule your self-tour today and take the first step toward getting more than

  175 Southern Breeze Lp, Winter Haven, FL 33880
• 

  /2

  $365,000

  Sold Oct 17, 2025

  236 Golf Aire Blvd, Winter Haven, FL 33884

  • 3 Beds
  • 2.5 Baths
  • 2,523 Sq Ft
  • Built 2000

  Last Sold Summary

  • 15% Below List Price
  • $145/SF
  • 27 Days On Market

  Current Estimated Value $375,358

  Last Listing Agent Amanda Harrison HARRISON REAL PROPERTY GROUP

  236 Golf Aire Blvd, Winter Haven, FL 33884
• 

  /2

  Not Listed For Sale

  6459 Hollyberry Ln NE, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1987

  6459 Hollyberry Ln NE, Winter Haven, FL 33881

  Last Sold Summary

  • 120 Days On Market
• 

  

  /30

  $240,000

  $10K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,883 Sq Ft

  15 Lake Howard Dr NW, Winter Haven, FL 33880

  This expansive property is a true diamond in the rough, perfectly positioned for the savvy investor looking for a great return on a "buy and hold" scenario or a strategic value-add project. Boasting a generous 0.41-acre lot, this property is designed for versatility. With a massive layout featuring 6 bedrooms and 4 bathrooms, the home offers the unique potential for 3 or even 4 separate doors

  

  Clarisa Moody

  MARZUCCO REAL ESTATE

  15 Lake Howard Dr NW, Winter Haven, FL 33880
• 

  

  /41

  $1,750 Per Month

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  204 6th Jpv St, Winter Haven, FL 33880

  Three bedroom, one bathroom home located in Winter Haven. This property features a roof installed in 2025 and an AC system installed in 2025 for energy efficiency and year round comfort. The interior floor plan includes a remodeled kitchen, a remodeled bathroom, and low maintenance ceramic tile flooring throughout with no carpet. Enjoy a functional layout with bright living spaces and a spacious

  Juan Corrales DALTON WADE INC

  204 6th Jpv St, Winter Haven, FL 33880
• 

  /2

  $152,250

  Sold Apr 08, 2026

  350 Winter Ridge Blvd, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Below List Price
  • $142/SF
  • 8 Days On Market

  Current Estimated Value $150,781

  Last Listing Agent Nomar Rosa LPT REALTY, LLC

  350 Winter Ridge Blvd, Winter Haven, FL 33881
• 

  /2

  Not Listed For Sale

  4065 Rolling Oaks Dr, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1983

  4065 Rolling Oaks Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 82 Days On Market

Showing Results 401 - 440, Page 11 of 18