49,347

Winter Haven, FL Homes

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  • /22

    $357,835

    New Construction $20K PRICE INCREASE Pending
    • 3 Beds
    • 2 Baths
    • 2,021 Sq Ft

    1509 Covey Rise Terrace, Winter Haven, FL 33884

    Under Construction. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration.

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    1509 Covey Rise Terrace, Winter Haven, FL 33884
  • /15

    $2,225 Per Month

    • 4 Beds
    • 2 Baths
    • 1,828 Sq Ft
    • House for Rent

    1054 Summer Glen Dr, 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,

    1054 Summer Glen Dr, Winter Haven, FL 33880
  • /2

    $160,000

    Sold Feb 20, 2026

    398 Winter Ridge Blvd Unit 398, Winter Haven, FL 33881

    • 2 Beds
    • 2 Baths
    • 1,241 Sq Ft
    • Built 1996

    Last Sold Summary

    • 3% Above List Price
    • $129/SF
    • 106 Days On Market

    Last Listing Agent CarLee Marchetti STAR REALTY OF WINTER HAVEN

    398 Winter Ridge Blvd Unit 398, Winter Haven, FL 33881
    • /2

      Not Listed For Sale

      12 Robin Ln, Winter Haven, FL 33880

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1976
      12 Robin Ln, Winter Haven, FL 33880

      Last Sold Summary

      • 4 Days On Market

  • /20

    $250,990

    New Construction $38K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    6524 Domizio Dr, Winter Haven, FL 33884

    Ready Now! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. The Glen Ridge single-family home is

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    6524 Domizio Dr, Winter Haven, FL 33884
  • /24

    $1,550 Per Month

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

    802 Eagle Pond Dr, Winter Haven, FL 33884

    FULLY FURNISHED and EQUIPPED including linens and dishes.Minimum 7 month lease.Enjoy the serene pond front views from this first floor 2 bedroom 2 bathroom condo located in the Eagle Pond Neighborhood in Gated, Cypresswood Golf and Country Club.MOVE IN WITH YOUR SUITCASE!Amenities include 24 hour manned gate, community pool, brand new pickleball and tennis courts, clubhouse with

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    802 Eagle Pond Dr, Winter Haven, FL 33884
  • /2

    $250,000

    Sold Feb 24, 2026

    509 Mckenna Dr, Winter Haven, FL 33881

    • 3 Beds
    • 2 Baths
    • 1,506 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $166/SF
    • 191 Days On Market

    Current Estimated Value $256,843

    Last Listing Agent EJ Jimenez KELLER WILLIAMS ADVANTAGE III

    509 Mckenna Dr, Winter Haven, FL 33881
    • /33

      Not Listed For Sale

      6132 Grand Oaks Dr SE, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 1994
      6132 Grand Oaks Dr SE, Winter Haven, FL 33884

      Last Sold Summary

      • 6 Days On Market

  • /15

    $582,194

    New Construction $5K PRICE INCREASE Pending
    • 4 Beds
    • 3 Baths
    • 2,551 Sq Ft

    1552 Covey Rise Terrace, Winter Haven, FL 33884

    Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your exploration. Plus, you're just 5

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    1552 Covey Rise Terrace, Winter Haven, FL 33884
  • /36

    $4,384

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 1,732 Sq Ft
    • Condo for Rent

    904 15th St NE Unit SI FL1-ID1520445P, Winter Haven, FL 33881

    The advertised rate of $4,384/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 15, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    904 15th St NE Unit SI FL1-ID1520445P, Winter Haven, FL 33881
  • /12

    $249,990

    Sold Apr 24, 2026

    5017 Kaia Ave, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,269 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 6% Below List Price
    • $197/SF
    • 205 Days On Market

    Current Estimated Value $243,667

    Meritage Homes VillaMar - Classic Series

    5017 Kaia Ave, Winter Haven, FL 33884
    • /15

      Not Listed For Sale

      712 Byni Ridge, Winter Haven, FL 33880

      • 4 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1979
      712 Byni Ridge, Winter Haven, FL 33880

      Last Sold Summary

      • 67 Days On Market

  • /17

    $380,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,250 Sq Ft

    1742 Upland Ln, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    1742 Upland Ln, Winter Haven, FL 33884
  • /21

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft
    • House for Rent

    1666 Ambar Ct, Winter Haven, FL 33881

    Located on a quiet residential community in Winter Haven, this property offers the perfect blend of comfort, convenience, and quality of life in the heart of Central Florida. Just minutes away from shopping centers, grocery stores, restaurants, hospitals, and schools, the location is ideal for families and anyone seeking everyday convenience. The home also features a spacious fenced backyard,

    Amis Quijada MY REALTY GROUP, LLC.

    1666 Ambar Ct, Winter Haven, FL 33881
  • /16

    $299,490

    Sold Apr 21, 2026

    6449 Domizio Dr, Winter Haven, FL 33884

    • 5 Beds
    • 2 Baths
    • 2,112 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 2% Above List Price
    • $142/SF
    • 20 Days On Market

    Current Estimated Value $311,000

    Lennar Villa Mar

    6449 Domizio Dr, Winter Haven, FL 33884
    • /2

      Est $224,580

      Not Listed For Sale

      2423 3rd St NE, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,173 Sq Ft
      • Built 2024
      2423 3rd St NE, Winter Haven, FL 33881

      Last Sold Summary

      • 7 Days On Market

  • /21

    $386,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,797 Sq Ft

    1726 Upland Ln, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    1726 Upland Ln, Winter Haven, FL 33884
  • /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

    $380,000

    Sold Jan 09, 2026

    204 S Lake Mariam Dr, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,826 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $208/SF
    • 63 Days On Market

    Current Estimated Value $374,793

    Last Listing Agent Michael Brenner CENTURY 21 MYERS REALTY

    204 S Lake Mariam Dr, Winter Haven, FL 33884
    • /2

      Est $254,786

      Not Listed For Sale

      127 Florida Dr, Winter Haven, FL 33881

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft
      • Built 2024
      127 Florida Dr, Winter Haven, FL 33881

      Last Sold Summary

      • 17 Days On Market

  • /72

    $394,900

    New Construction $5K PRICE DROP Pending
    • 5 Beds
    • 3 Baths
    • 2,386 Sq Ft

    1138 Michelangelo Ln, Winter Haven, FL 33884

    Under contract-accepting backup offers. *** No CDD fees!!***Welcome to this stunning smart home offering the perfect blend of modern design, space, and functionality. This impressive two-story residence features 5 bedrooms, 3 full bathrooms, and a spacious 3-car garage, making it ideal for growing families or those who love to entertain. Step inside to discover a bright and open floor plan

    Agent Photo

    David Hartigan

    JASON MITCHELL REAL ESTATE FLO

    1138 Michelangelo Ln, Winter Haven, FL 33884
  • /31

    $1,795 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,425 Sq Ft
    • House for Rent

    2405 Willow Way, Winter Haven, FL 33881

    Virtually Staged. Brand-New Townhome in Winter Haven | 2 Bed • 2.5 Bath • Modern Living at Its Best! ***Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome home to this beautiful brand-new 2-bedroom, 2.5-bath townhome located in one of Winter Haven's growing and convenient communities. Thoughtfully designed with a modern open floor plan, this home offers the

    Jacob Hara TRANSCEND REALTY

    2405 Willow Way, Winter Haven, FL 33881
  • /2

    $230,000

    Sold Jun 23, 2026

    115 Grady Polk Rd, Winter Haven, FL 33880

    • 3 Beds
    • 1 Bath
    • 1,264 Sq Ft
    • Built 1963

    Last Sold Summary

    • 5% Above List Price
    • $182/SF
    • 2 Days On Market

    Current Estimated Value $214,632

    Last Listing Agent Bryan Czajkowski DALTON WADE INC

    115 Grady Polk Rd, Winter Haven, FL 33880
    • /2

      Est $267,437

      Not Listed For Sale

      256 Ruby Lake Ln, Winter Haven, FL 33884

      256 Ruby Lake Ln, Winter Haven, FL 33884

      Last Sold Summary

      • 15 Days On Market

  • /19

    $326,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,815 Sq Ft

    1739 Upland Ln, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    1739 Upland Ln, Winter Haven, FL 33884
  • /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

    $125,000

    Sold Aug 06, 2025

    4918 Rosewood St, Winter Haven, FL 33880

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1980

    Last Sold Summary

    • 6% Below List Price
    • $124/SF
    • 96 Days On Market

    Last Listing Agent Kathy Devor COLDWELL BANKER REALTY

    4918 Rosewood St, Winter Haven, FL 33880
    • /49

      Est $291,397

      Not Listed For Sale

      996 Buccaneer Blvd, Winter Haven, FL 33880

      • 3 Beds
      • 2 Baths
      • 1,685 Sq Ft
      • Built 2013
      996 Buccaneer Blvd, Winter Haven, FL 33880

      Last Sold Summary

      • 16 Days On Market

  • /5

    $295,529

    New Construction $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,202 Sq Ft

    2335 Brassie Ct, Winter Haven, FL 33884

    Under Construction. This two-story home features 4 bedrooms and 2 and a half baths. This Home begins with a two-story foyer opening up to the spacious first floor living spaces. The kitchen shines with abundant counter space and an island perfect for entertaining, Upstairs, you will find all four bedrooms and the designated laundry room. CUSTOM EXTERIOR includes 30-year mildew resistant

    Agent Photo

    Jesse Tapia

    ADAMS HOMES REALTY

    2335 Brassie Ct, Winter Haven, FL 33884
  • /21

    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • House for Rent

    1708 Teagan Ln, Winter Haven, FL 33884

    Beautiful single family house built in 2024 with 3 bedrooms, 2 bathrooms, with open kitchen, Living room and Dining Area, Master Bedroom with attached master bath with double sinks and large walking closet, 2 other bedrooms with hall bath, 2 car garages with appliances Stove, Refrigerator, Dishwasher, Microwave, Washer and Dryer. Amenities include pool, playground etc. in the community. 1st,

    K.C. Thomas CHARLES RUTENBERG REALTY ORLANDO

    1708 Teagan Ln, Winter Haven, FL 33884
  • /2

    $389,000

    Sold Mar 23, 2026

    1507 Riviera Ct, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 1,983 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Below List Price
    • $196/SF
    • 21 Days On Market

    Current Estimated Value $392,414

    Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.

    1507 Riviera Ct, Winter Haven, FL 33884
    • /32

      Est $131,119

      Not Listed For Sale

      2600 Lucerne Park Rd Unit 508, Winter Haven, FL 33881

      • 2 Beds
      • 2 Baths
      • 845 Sq Ft
      • Built 1987
      2600 Lucerne Park Rd Unit 508, Winter Haven, FL 33881

      Last Sold Summary

      • 159 Days On Market

  • /4

    $369,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft

    Esperanza Plan at Villa Mar, Winter Haven, FL 33884

    Meet the Esperanza, a single-story, multi-generational home designed for modern living with flexibility and comfort. This 4-bedroom, 3-bathroom, 2-car garage home features a separate multi-gen suite with its own bathroom and kitchenette, ideal for extended family or guests. The spacious layout offers distinct areas for gathering and relaxing, including an open-concept living and dining space

    Casa Fresca Homes Builder
    6614 Crescent Loop Unit 37807416, Winter Haven, FL 33884
  • /8

    $950 Per Month

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

    663 Ave J NW Unit 2, Winter Haven, FL 33881

    Discover the perfect blend of comfort, privacy, and convenience in this well-maintained Winter Haven residence. Ideally suited for anyone seeking a low-maintenance, independent living space, this cozy 1-bedroom, 1-bathroom apartment delivers a peaceful residential feel with excellent functional perksLease and Move-In Details:Availability: Ready for immediate move-in.Parking:

    663 Ave J NW Unit 2, Winter Haven, FL 33881
  • /2

    $740,000

    Sold Jul 10, 2026

    1787 Lake Hill Dr, Winter Haven, FL 33884

    • 4 Beds
    • 3.5 Baths
    • 2,944 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Below List Price
    • $251/SF
    • 32 Days On Market

    Current Estimated Value $744,238

    Last Listing Agent Kayly Malinas JOHN WOOD REALTY, INC.

    1787 Lake Hill Dr, Winter Haven, FL 33884
    • /46

      Est $230,354

      Not Listed For Sale

      3389 Raleigh Dr, Winter Haven, FL 33884

      • 2 Beds
      • 2 Baths
      • 1,295 Sq Ft
      • Built 2017
      3389 Raleigh Dr, Winter Haven, FL 33884

      Last Sold Summary

      • 40 Days On Market

  • /6

    $312,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    Glimmer Plan at Sunset Hills, Winter Haven, FL 33881

    From the covered porch, you step into the foyer, where you're greeted by a coat closet and welcomed into the open dining area, kitchen, and family room. Just off the kitchen is the laundry room, which also provides access to the two-car garage. The family room leads to a back patio for outdoor living, as well as the private primary bedroom featuring a walk-in closet and a spacious primary bath.

    Starlight Homes Builder
    3136 Sunset Hills Rd Unit 36493568, Winter Haven, FL 33881
  • /14

    $1,695 Per Month

    • 3 Beds
    • 2 Baths
    • 1,147 Sq Ft
    • House for Rent

    1539 Roselawn St SW, Winter Haven, FL 33880

    Beautifully fully remodeled 3-bedroom, 2-bathroom home located at 1539 Roselawn, offering modern comfort and stylish living throughout. This residence features premium waterproof luxury vinyl flooring, a spacious and upgraded kitchen with elegant granite countertops, and stainless steel appliances. The home has been thoughtfully updated to provide both functionality and design, along with a

    Ines Morales LA ROSA REALTY KISSIMMEE

    1539 Roselawn St SW, Winter Haven, FL 33880
  • /2

    $415,000

    Sold Dec 15, 2025

    2997 Plantation Rd, Winter Haven, FL 33884

    • 3 Beds
    • 2 Baths
    • 2,603 Sq Ft
    • Built 1986

    Last Sold Summary

    • 5% Below List Price
    • $159/SF
    • 88 Days On Market

    Current Estimated Value $422,383

    Last Listing Agent Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    2997 Plantation Rd, Winter Haven, FL 33884
    • /2

      Est $282,291

      Not Listed For Sale

      1512 Grey Eagle Ln, Winter Haven, FL 33881

      • 4 Beds
      • 2 Baths
      • 1,820 Sq Ft
      • Built 2018
      1512 Grey Eagle Ln, Winter Haven, FL 33881

      Last Sold Summary

      • 45 Days On Market

Showing Results 441 - 480, Page 12 of 18

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