Winter Haven, FL Homes

• 

  

  

  /22

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  2007 Oliver Place, Winter Haven, FL 33881

  Welcome to this well-maintained 3-bedroom, 2-bath home located in the heart of Havendale. Featuring a newer roof (2018), luxury vinyl flooring, a brand new washer and dryer and new plumbing in the guest bath, this home is nestled in a convenient and safe neighborhood close to shopping, dining, and all the amenities of downtown Winter Haven, this property offers comfort and convenience in one.

  Nolan Chestnut DALTON WADE INC

  2007 Oliver Place, Winter Haven, FL 33881
• 

  

  

  /13

  $2,200 per month

  • 4 Beds
  • 2.5 Baths
  • 1,879 Sq Ft
  • House for Rent

  981 Harold Pass, Winter Haven, FL 33884

  Beautiful four bedroom, two and a half baths, and a two-car garage single family home WITH brand new WASHER, DRYER and french door REFRIGERATOR. This home offers an open floor plan with great room, dining room, and kitchen with large kitchen island. The kitchen features ample counter space, and generous pantry. The casual dining area allows outdoor access to a covered lanai via sliding glass

  Ashley Porto FLORIDA CONNEXION PROPERTIES

  981 Harold Pass, Winter Haven, FL 33884
• 

  

  /2

  $255,000 Sold Aug 08, 2025

  • 1,650 Sq Ft
  • $155/SF
  • 209 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  1891 18th St NW, Winter Haven, FL 33881

  This beautiful home offers approximately 1,650 square feet of living space with 3 bedrooms and 2 bathrooms. The property sits on a lot of approximately 0.23 acres and comes with an additional lot of .06 acres. With mature landscaping, a greenhouse, and a fenced-in yard providing ample outdoor space and privacy.The interior features terrazzo flooring, a picture window that allows for

  Maria Deary COLDWELL BANKER REALTY

  1891 18th St NW, Winter Haven, FL 33881
• 

  

  

  /18

  Est $357,862 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,467 Sq Ft

  217 Majestic Gardens Ln, Winter Haven, FL 33880

  217 Majestic Gardens Ln, Winter Haven, FL 33880
• 

  

  

  /18

  $214,000

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  3701 Avenue J NW, Winter Haven, FL 33881

  NEW ROOF INSTALLED ON 9/8 WITH TRANSFERABLE WARRANTY!! This 3/1 "Turn Key Property" is ready to move! Located close in proximity to most any necessary shopping. This fenced in home (with metal shed) is very clean and includes clean steel appliances, ceiling fans, luxury vinyl flooring, tiled shower walls, brush nickle hardware throughout and a new water heater. This home is listed at the right

  Johnathan Dyess CREEKWATER REALTY LLC

  3701 Avenue J NW, Winter Haven, FL 33881
• 

  

  /19

  $1,699 per month

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • House for Rent

  631 Heather Glen Loop, Winter Haven, FL 33884

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $1843.90. That covers your base rent, $1699.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  631 Heather Glen Loop, Winter Haven, FL 33884
• 

  

  /11

  $259,077 Sold Aug 07, 2025

  • 1,429 Sq Ft
  • $181/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  2224 Chris Dr, Winter Haven, FL 33884

  This new home is laid out on a single level for low maintenance living. Two secondary bedrooms share a bathroom in the hall at the front of the home, while the owner’s suite is tucked into the back corner with an attached bathroom and walk-in closet. Down the foyer is the open-concept living area, which includes a fully equipped kitchen, an intimate dining room and family room with patio access.

  Lennar

  2224 Chris Dr, Winter Haven, FL 33884
• 

  

  /69

  Est $362,051 Not Listed For Sale

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

  1061 Windlass Way, Winter Haven, FL 33880

  1061 Windlass Way, Winter Haven, FL 33880
• 

  

  /18

  $239,900

  • 4 Beds
  • 2 Baths
  • 1,314 Sq Ft

  103 Orange Ave, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Welcome to 103 Orange Avenue, Winter Haven, FL! This beautifully updated 4-bedroom, 2-bathroom home offers the perfect blend of modern upgrades and comfortable living. Nestled on an oversized yard, this property provides plenty of space for entertaining, gardening, or enjoying the Florida sunshine. Step inside to find a fully renovated kitchen and

  Jason Stone BHHS FLORIDA PROPERTIES GROUP

  103 Orange Ave, Winter Haven, FL 33880
• 

  

  /11

  $1,750 per month

  • 4 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • House for Rent

  2460 Avenue E SW, Winter Haven, FL 33880

  Welcome to 2460 Avenue E SW in Winter Haven! A great 4 bedroom 2 bath home in a centralized location with close proximity to parks, shopping, medical facilities, and entertainment. Available for viewing 8/31/25. available to move in 8/31/25.

  Anya Kovalenko LPT REALTY, LLC

  2460 Avenue E SW, Winter Haven, FL 33880
• 

  /2

  $302,900 Sold Aug 07, 2025

  • 1,754 Sq Ft
  • $173/SF
  • 12 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2025

  3135 Laurel Oak Ln, Winter Haven, FL 33884

  Move-in ready 4-bedroom home for sale in Winter Haven, Florida! A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. Plus,

  George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  3135 Laurel Oak Ln, Winter Haven, FL 33884
• 

  /2

  Est $282,849 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft

  248 Hayley St, Winter Haven, FL 33884

  248 Hayley St, Winter Haven, FL 33884
• 

  

  /25

  $299,990 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  343 Lake Smart Cir, Winter Haven, FL 33881

  Come and discover the experience of owning this well-maintained 3-bedroom, 2-bath home with 1,450 sq. ft. of living space featuring an open and thoughtfully designed floor plan. Located in the desirable Lake Smart Point community, you’ll enjoy proximity to both Lake Conine and Lake Smart—each with its own boat ramp, perfect for fishing and outdoor activities. This cozy home boasts tile flooring

  Migdalia Nieves Mercado HOMETRUST REALTY GROUP

  343 Lake Smart Cir, Winter Haven, FL 33881
• 

  

  /20

  $2,149 per month

  • 4 Beds
  • 2.5 Baths
  • 2,733 Sq Ft
  • House for Rent

  552 Cody Caleb Dr, Winter Haven, FL 33884

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2293.90. That covers your base rent, $2149.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  552 Cody Caleb Dr, Winter Haven, FL 33884
• 

  /2

  $335,620 Sold Aug 06, 2025

  • 1,673 Sq Ft
  • $201/SF
  • 29 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  71 Sunset View Dr, Winter Haven, FL 33884

  Lakefront Living for the Life You Deserve! Welcome to this rarely available, WINTERSET first-floor waterfront condominium located on the scenic Chain of Lakes—a dream setting for anyone seeking relaxation, recreation, and community. This turn-key ready 2-bedroom, 2-bath home offers 1,673 sq ft of beautifully designed, low-maintenance living with breathtaking water views and direct access to

  Diana Brown REMAX EXPERTS

  71 Sunset View Dr, Winter Haven, FL 33884
• 

  /2

  Est $298,414 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  949 Harold Pass, Winter Haven, FL 33884

  949 Harold Pass, Winter Haven, FL 33884
• 

  

  /19

  $254,500

  • 3 Beds
  • 2 Baths
  • 1,303 Sq Ft

  2033 Whispering Trails Blvd, Winter Haven, FL 33884

  Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 15 minutes from the exciting attractions of Legoland, and less than an hour from the magical world of Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and

  Vivian Ortiz OAK AVENUE REAL ESTATE LLC

  2033 Whispering Trails Blvd, Winter Haven, FL 33884
• 

  

  /20

  $1,990 per month

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  2219 Chris Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. ** Lawn Mower included**Spacious 4-Bedroom Home with Loft for Rent in Winter Haven!Brand-new construction - Be the first tenant!Discover the perfect blend of comfort, style, and quality living in this beautiful home located in the Peace Creek Reserve community of Winter Haven. Featuring 4 bedrooms, 2.5 bathrooms in a corner lot,

  Pri Naccarato EXP REALTY LLC

  2219 Chris Dr, Winter Haven, FL 33884
• 

  /2

  $125,000 Sold Aug 06, 2025

  • 1,008 Sq Ft
  • $124/SF
  • 96 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  4918 Rosewood St, Winter Haven, FL 33880

  This home is a MUST HAVE!! The home has been updated from top to bottom. The kitchen features beautiful granite counters and new kitchen cabinets. Both baths have been remodeled. All the flooring is either ceramic or vinyl flooring. The shingle roof is 10 years old and the air conditioner was just installed in 2025. The water heater was installed in 2024. The home will be sold furnished

  Kathy Devor COLDWELL BANKER REALTY

  4918 Rosewood St, Winter Haven, FL 33880
• 

  /2

  Est $262,963 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  2928 Whispering Trails Dr, Winter Haven, FL 33884

  2928 Whispering Trails Dr, Winter Haven, FL 33884
• 

  

  /53

  $29,900

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  60 Stebbins Dr, Winter Haven, FL 33884

  (Espanol a continuacion) Discover your perfect retirement oasis in this completely renovated 1985 two-bedroom, one-bathroom mobile home in the prestigious Grove Shores 55+ Community. Located on scenic Lake Daisy with fishing dock and stunning water views, this move-in ready home offers the affordable lakefront lifestyle you've been dreaming of. Lot rent is just $714 monthly and includes water,

  Brenton Basinger Florida Mobile Home Solutions, Inc.

  60 Stebbins Dr, Winter Haven, FL 33884
• 

  

  /17

  $2,215 per month

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

  313 Towhee Rd, Winter Haven, FL 33881

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2359.90. That covers your base rent, $2215.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  313 Towhee Rd, Winter Haven, FL 33881
• 

  /2

  $290,000 Sold Aug 06, 2025

  • 1,817 Sq Ft
  • $160/SF
  • 122 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2023

  135 Krenson Bay Loop, Winter Haven, FL 33881

  Welcome to 135 Krenson Bay Loop, Winter Haven, a beautifully maintained 4-bedroom, 2-bathroom home in the desirable Krenson Bay community! This stunning residence offers a bright and open floor plan, perfect for modern living.Step inside to find a spacious living area filled with natural light, seamlessly connecting to the gourmet kitchen, which boasts granite countertops, stainless steel

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  135 Krenson Bay Loop, Winter Haven, FL 33881
• 

  /2

  Est $298,457 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  1005 Harold Pass, Cypress Gardens, FL 33884

  1005 Harold Pass, Cypress Gardens, FL 33884
• 

  

  /19

  $169,900

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  5850 Cypress Gardens Blvd Unit 403, Winter Haven, FL 33884

  Discover the easy, maintenance-free living of this well-kept 3BR/2.5BA townhouse in SE Winter Haven. The downstairs shines with ceramic tile, a modern kitchen featuring granite countertops, wood cabinets, a breakfast bar, and a pantry. Enjoy separate living and family rooms, a handy half bath, inside laundry, and a private patio for relaxing. Upstairs, find three comfortable bedrooms, including a

  David Craig 1513 REALTY LLC

  5850 Cypress Gardens Blvd Unit 403, Winter Haven, FL 33884
• 

  

  /37

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Condo for Rent

  2040 San Marcos Dr SE Unit 203, Winter Haven, FL 33880

  Welcome to this charming upstairs 2-bedroom, 2-bath condo with an oversized loft in the Park Lake Community in the Penwood Building. Featuring beautiful wood accents, a cozy fireplace this home offers inviting spaces with plenty of personality. Large windows provide peaceful tree-lined views, and residents can enjoy access to both a serene community dock on Lake Lulu which is on the Chain of

  Natalie Middlebrook STAR REALTY OF WINTER HAVEN

  2040 San Marcos Dr SE Unit 203, Winter Haven, FL 33880
• 

  /2

  $430,000 Sold Aug 06, 2025

  • 3,368 Sq Ft
  • $128/SF
  • 130 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2007

  1904 Eloise Cove Dr, Winter Haven, FL 33884

  "HUGE PRICE REDUCTION" ON THIS 2 STORY FAMILY HOME FEATURING 4 BEDROOMS, 4.5 BATHROOMS LOCATED IN A VERY ESTABLISHED GATED COMMUNITY JUST STEPS FROM LEGOLAND!!! The cook in the family will love the oversized kitchen with stainless refrigerator, dishwasher, double ovens, microwave, breakfast bar, island, desk area, granite countertops and an abundance of 42 in. upper cabinetry. The primary

  Bryan Dicks COLDWELL BANKER REALTY

  1904 Eloise Cove Dr, Winter Haven, FL 33884
• 

  /2

  Est $432,772 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,045 Sq Ft

  1146 Sawgrass Dr, Winter Haven, FL 33884

  1146 Sawgrass Dr, Winter Haven, FL 33884
• 

  

  /15

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,102 Sq Ft

  1414 26th St NW, Winter Haven, FL 33881

  Charming Inwood home, located one block to lake Alfred. This 3 bedroom , 2 bathroom is perfect for 1st time home buyer or as an investment property. Its close to school and shopping. The drain field was done approximately 8 mths ago, New kitchen cabinets were put in, also both toilets and vanity, plus a new hot water tank. Please note that the hose will need a new A/C unit., however if the buyer

  Baijnauth Singh LIBERTY HOME SALES INC

  1414 26th St NW, Winter Haven, FL 33881
• 

  

  /17

  $2,070 per month

  • 3 Beds
  • 2 Baths
  • 1,874 Sq Ft
  • House for Rent

  905 Turnstone Ln, Winter Haven, FL 33880

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2214.90. That covers your base rent, $2070.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  905 Turnstone Ln, Winter Haven, FL 33880
• 

  

  /25

  $299,990 Sold Aug 05, 2025

  • 1,426 Sq Ft
  • $210/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  3470 Evening Star Dr, Winter Haven, FL 33881

  From the front porch, you enter into the foyer and are immediately welcomed into the open family room, dining area, and kitchen. Just off the kitchen is the primary bedroom, which includes a primary bath, walk-in closet, and convenient access to the laundry room. The family room opens to a back patio, perfect for outdoor relaxation. On the opposite side of the kitchen, you’ll find two additional

  Starlight Homes

  3470 Evening Star Dr, Winter Haven, FL 33881
• 

  /2

  Est $323,262 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,215 Sq Ft

  993 Harold Pass, Winter Haven, FL 33884

  993 Harold Pass, Winter Haven, FL 33884
• 

  

  /17

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,438 Sq Ft

  3830 Osprey Pointe Cir, Winter Haven, FL 33884

  Beautiful community of Osprey Pointe on Lake Ned. This 2 bedroom/2 bath home is move in ready. Kitchen with stainless steel appliances, granite counter tops, tile flooring, dinette area. The open floor plan is great for entertaining complete with a large screened in porch and extended paver patio area. No rear neighbors. Living room has newer laminate flooring, master bath has ceramic tile, dual

  Jonathan Minerick HOMECOIN.COM

  3830 Osprey Pointe Cir, Winter Haven, FL 33884
• 

  

  /16

  $1,920 per month

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft
  • House for Rent

  956 Sunshine Way SW, Winter Haven, FL 33880

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  956 Sunshine Way SW, Winter Haven, FL 33880
• 

  

  /26

  $328,990 Sold Aug 05, 2025

  • 2,447 Sq Ft
  • $134/SF

  • 5 Beds
  • 3 Baths
  • Built 2025

  3475 Costello Cir, Winter Haven, FL 33884

  The property is located at 3475 Costello Circle WINTER HAVEN FL 33884 priced at 328990, the square foot and stories are 2447, 2.The number of bath is 3, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton

  3475 Costello Cir, Winter Haven, FL 33884
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  420 Village Cir SW, Winter Haven, FL 33880

  420 Village Cir SW, Winter Haven, FL 33880
• 

  

  /73

  $448,900

  • 3 Beds
  • 2 Baths
  • 2,031 Sq Ft

  5225 Pebble Beach Blvd, Winter Haven, FL 33884

  Your Florida dream home is ready and waiting! This fully furnished Sebastian floor plan offers 3 bedrooms, 2 baths, a 2-car garage plus a dedicated golf cart garage and YES, the golf cart is included. Located on a premium lot overlooking Lake Ashton’s West Course 17th hole and a tranquil pond, enjoy exceptional privacy and breathtaking views from your expansive screened lanai. Step inside to

  Candra Alston LAKE ASHTON REALTY INC.

  5225 Pebble Beach Blvd, Winter Haven, FL 33884
• 

  

  /15

  $1,995 per month

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft
  • House for Rent

  621 Squires Grove Dr, Winter Haven, FL 33880

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  621 Squires Grove Dr, Winter Haven, FL 33880
• 

  

  /38

  $314,845 Sold Aug 05, 2025

  • 1,672 Sq Ft
  • $188/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  4093 Giorgio Dr, Winter Haven, FL 33884

  The property is located at 4093 Giorgio Drive WINTER HAVEN FL 33884 priced at 314845, the square foot and stories are 1672, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton

  4093 Giorgio Dr, Winter Haven, FL 33884
• 

  

  /11

  Est $261,667 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,461 Sq Ft

  1164 Deepwater Cir, Winter Haven, FL 33880

  1164 Deepwater Cir, Winter Haven, FL 33880

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