Winter Haven, FL Homes

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  /24

  $310,000

  $100K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  4612 Reynosa Dr SW, Winter Haven, FL 33880

  Under contract-accepting backup offers. Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from

  

  Trent Shackelford

  LPT REALTY LLC

  4612 Reynosa Dr SW, Winter Haven, FL 33880
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  /7

  $1,000

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 1,111 Sq Ft
  • House for Rent

  101 Lake Sears Dr, Winter Haven, FL 33880

  Nice and clean 3 bedroom house shared bathroom. I have a cat but mostly outside

  101 Lake Sears Dr, Winter Haven, FL 33880
• 

  

  /2

  $232,000

  Sold Aug 04, 2025

  1674 Linz Ct, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $172/SF
  • 59 Days On Market

  Current Estimated Value $228,849

  Last Listing Agent Marti Sutton CENTURY 21 WATSON & MYERS REALTY

  1674 Linz Ct, Winter Haven, FL 33884
• 

  

  

  /34

  Est $109,589

  Not Listed For Sale

  2040 San Marcos Dr SE Unit 108, Winter Haven, FL 33880

  • 1 Bed
  • 1 Bath
  • 666 Sq Ft
  • Built 1985

  2040 San Marcos Dr SE Unit 108, Winter Haven, FL 33880

  Last Sold Summary

  • 28 Days On Market
• 

  

  

  /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
• 

  

  /11

  $1,825

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  711 Avenue B NE, Winter Haven, FL 33881

  This is a 3/2 home in Winter Haven Fl. This home is move in ready and had been freshly updated. Call for your showing today. Close to downtown and convenient to all winter haven has to offer.Washer Dryer hook upsCentral heat and airScreened porchLong term or short term approved.

  711 Avenue B NE, Winter Haven, FL 33881
• 

  /2

  $191,000

  Sold Jul 21, 2026

  2348 Isle Royale Ct SE, Winter Haven, FL 33880

  • 2 Beds
  • 2.5 Baths
  • 1,281 Sq Ft
  • Built 1997

  Last Sold Summary

  • 15% Below List Price
  • $149/SF
  • 503 Days On Market

  Current Estimated Value $194,282

  Last Listing Agent Fatma Higdon HIGDON HOMES REALTY LLC

  2348 Isle Royale Ct SE, Winter Haven, FL 33880
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  /12

  Not Listed For Sale

  713 Byni Ridge, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1990

  713 Byni Ridge, Winter Haven, FL 33880

  Last Sold Summary

  • 14 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
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  /11

  $1,100

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  836 Lake Martha Dr NE Unit B, Winter Haven, FL 33881

  This 1 bedroom 1 bath is located close to downtown Winter Haven area walking distance to restaurants and the local Farmer's Market. Very close to a jogging track and several sports fields for fun recreation. Water, washer and dryer, Wi-Fii, trash and water included. Close by a lake to enjoy beautiful sunsets at the lake. The neighborhood is very nice and quiet but walking distance to museums

  836 Lake Martha Dr NE Unit B, Winter Haven, FL 33881
• 

  /2

  $31,000

  Sold Apr 13, 2026

  125 5th St NE, Winter Haven, FL 33881

  • Land
  • 6,534 Sq Ft
  • $206,667 per Acre

  Last Sold Summary

  • 44% Below List Price
  • 7 Days On Market

  Last Listing Agent Milton De La Cruz LAKELAND HOMES AND REALTY, LLC

  125 5th St NE, Winter Haven, FL 33881
• 

  

  /28

  Est $127,218

  Not Listed For Sale

  689 Lake Howard Dr NW Unit 103, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1975

  689 Lake Howard Dr NW Unit 103, Winter Haven, FL 33880

  Last Sold Summary

  • 23 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
• 

  

  /12

  $1,400

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Condo for Rent

  357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881

  Available NowLakefront Condo on Lake Smart. The community of Winter Ridge Condos offer a community swimming pool, club house, and private boat dock. This Lakefront inviting condo features 2 large bedrooms and 2 bathrooms and covered car-port. An open layout living/dinning combo and abundant natural light. No Smoking. $1400 rent per month plus one month security deposit and utilities

  357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881
• 

  /2

  $360,000

  Sold May 07, 2026

  232 College Grove Cir NE, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 2,087 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Above List Price
  • $172/SF
  • 2 Days On Market

  Current Estimated Value $356,610

  Last Listing Agent Amy Reynolds LOCKHART & ASSOCIATES INC

  232 College Grove Cir NE, Winter Haven, FL 33881
• 

  /2

  Est $284,012

  Not Listed For Sale

  5069 Brenton Manor Ave, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,895 Sq Ft
  • Built 2013

  5069 Brenton Manor Ave, Winter Haven, FL 33881

  Last Sold Summary

  • 154 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
• 

  

  /27

  $1,600

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Condo for Rent

  690 Avenue C SE Unit 690, Winter Haven, FL 33880

  690 Avenue C SE Unit 690, Winter Haven, FL 33880
• 

  /2

  $283,990

  Sold Apr 02, 2026

  1112 Tyler Loop, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • Built 2025

  Last Sold Summary

  • $151/SF
  • 8 Days On Market

  Current Estimated Value $282,142

  Last Listing Agent Ben Goldstein LENNAR REALTY

  1112 Tyler Loop, Winter Haven, FL 33884
• 

  /2

  Est $329,732

  Not Listed For Sale

  118 Lake Sears Dr, Winter Haven, FL 33880

  • 2 Beds
  • 3 Baths
  • 1,422 Sq Ft
  • Built 1957

  118 Lake Sears Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 5 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
• 

  

  /13

  $2,150

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • House for Rent

  1108 29th St NW, Winter Haven, FL 33881

  4 bed/2 bath home with a large fenced backyard.Fully renovated for your convenience.Contact me to visit this beautiful property you will soon call home!

  1108 29th St NW, Winter Haven, FL 33881
• 

  /2

  $349,000

  Sold Apr 24, 2026

  5392 Chandler Dr, Winter Haven, FL 33884

  • 4 Beds
  • 3 Baths
  • 3,034 Sq Ft
  • Built 2006

  Last Sold Summary

  • 18% Below List Price
  • $115/SF
  • 211 Days On Market

  Current Estimated Value $357,310

  Last Listing Agent Jenni Thompson KELLER WILLIAMS REALTY

  5392 Chandler Dr, Winter Haven, FL 33884
• 

  /2

  Est $311,104

  Not Listed For Sale

  3810 Fieldstone Cir, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 2016

  3810 Fieldstone Cir, Winter Haven, FL 33881

  Last Sold Summary

  • 206 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
• 

  

  /3

  $2,350

  Total Monthly Price

  • 5 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • House for Rent

  6224 Botticella Blvd, Winter Haven, FL 33884

  The first floor of this new two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom.

  6224 Botticella Blvd, Winter Haven, FL 33884
• 

  /2

  $245,000

  Sold Dec 08, 2025

  512 Mckenna Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,506 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $163/SF
  • 116 Days On Market

  Current Estimated Value $246,464

  Last Listing Agent EJ Jimenez KELLER WILLIAMS ADVANTAGE III

  512 Mckenna Dr, Winter Haven, FL 33881
• 

  /2

  Not Listed For Sale

  225 Sweet Cir, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1986

  225 Sweet Cir, Winter Haven, FL 33884

  Last Sold Summary

  • 64 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
• 

  

  /19

  $900

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft
  • Condo for Rent

  1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880

  Centrally located to restaurants, Aldis, Lowe's and other shopping within walking distance. Small quiet apartments - property has security lights for safety.

  1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880
• 

  /2

  $299,990

  Sold Nov 24, 2025

  3239 Nightfall Rd, Winter Haven, FL 33881

  • 3 Beds
  • 3 Baths
  • 1,426 Sq Ft
  • Built 2025

  Last Sold Summary

  • $210/SF

  Current Estimated Value $299,900

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  3239 Nightfall Rd, Winter Haven, FL 33881
• 

  /2

  Not Listed For Sale

  5947 Silver Fox Dr, Winter Haven, FL 33884

  • 4 Beds
  • 3 Baths
  • 1,987 Sq Ft
  • Built 1981

  5947 Silver Fox Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 132 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
• 

  

  /12

  $1,475

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881

  This cozy Cottage is a 1/1 in Winter Haven Fl. Walk to downtowns restaurant and local shops and breweries. Close to Legoland and major medical. Short term unit with small kitchenette. Fenced yard with private spa. This home is set up for short term rental and has kitchenette with Convection Microwave, coffee pot, and all dishware. Washer Dryer, queen bed, TVs in the living room and bedroom.

  448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881
• 

  

  /12

  $354,999

  Sold Jun 02, 2026

  5389 San Pietro Dr, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,471 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $144/SF
  • 32 Days On Market

  Current Estimated Value $351,468

  Casa Fresca Homes Villa Mar

  5389 San Pietro Dr, Winter Haven, FL 33884
• 

  

  /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
• 

  

  /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
• 

  

  /6

  $1,397 Per Month

  • 2 Beds
  • 1 Bath
  • 914 Sq Ft
  • Townhouse for Rent

  3008 Saint Paul Dr Unit 3012, Winter Haven, FL 33880

  Beautiful 2/1 VIEW TODAY!

  Adan Ordonez ADAN INVESTMENTS REAL ESTATE GROUP, PLLC

  3008 Saint Paul Dr Unit 3012, Winter Haven, FL 33880
• 

  

  /57

  $100,000

  Sold Aug 22, 2025

  88 Sago Palm Way, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  Last Sold Summary

  • 33% Below List Price
  • $69/SF
  • 302 Days On Market

  Last Listing Agent Chrissy Walter Sunset Home Sales

  88 Sago Palm Way, Winter Haven, FL 33880
• 

  

  /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

Showing Results 361 - 400, Page 10 of 18