894

Winter Haven, FL Homes for Rent under $2,500

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  • /6

    $1,590 Per Month

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Property for Rent

    21 Stebbins Dr Unit 21, Winter Haven, FL 33884

    Still renting an apartment? It's time for an upgrade. At Grove Shores, you can enjoy real home living in a professionally managed, family-friendly neighborhood. This 2 bed / 1 bath home won't last long-don't miss your chance to have more space and more freedom. Call now to schedule your tour!

    Tori Coil Grove Shores

    21 Stebbins Dr Unit 21, Winter Haven, FL 33884
  • /13

    $945 Per Month

    • 1 Bed
    • 1 Bath
    • 620 Sq Ft
    • "Charming 1-Bedroom Home in Winter Haven – Perfect for Cozy Living!"

    115 8th St SE, Winter Haven, FL 33880

    Encounter the charm of 115 8th St SE in Winter Haven, FL, where cozy living meets ultimate convenience. This delightful one-bedroom, one-bathroom home offers a serene retreat in a vibrant community. Located in the heart of Winter Haven, you're just moments away from local attractions, dining, and shopping options. Enjoy the ease of a single-level home without the hassle of stairs or multiple

    115 8th St SE, Winter Haven, FL 33880
  • /32

    $1,795 Per Month

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

    2531 Pine St, Winter Haven, FL 33880

    Virtually Staged. Stylish 2-Bedroom Townhome in Winter Haven | Modern Comfort, Prime Location & Move-In Ready! Welcome to 2531 Pine Place, Winter Haven, FL 33881—a beautifully designed 2-bedroom, 2.5-bath townhome that offers the perfect blend of style, comfort, and convenience. Whether you're a professional, small family, or someone looking for low-maintenance living, this inviting home is

    Jacob Hara TRANSCEND REALTY

    2531 Pine St, Winter Haven, FL 33880
  • /16

    $2,195 Per Month

    • 5 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • House for Rent

    6240 Botticella Blvd, Winter Haven, FL 33884

    Live where every day feels like vacation! Welcome to Villa Mar in Winter Haven, FL — a beautiful 5 bed, 2 bath home offering open-concept living, stylish design, and all the perks of Central Florida convenience. Enjoy mornings on your covered patio, evenings in your spacious family room, and weekends exploring nearby shopping, dining, and entertainment. With quick access to I-4 and major

    6240 Botticella Blvd, Winter Haven, FL 33884
  • /20

    $2,350 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,933 Sq Ft
    • House for Rent

    693 Reggie Rd, Winter Haven, FL 33884

    READY TO MOVE !!!! This almost 1900 sq ft beautiful two-story home features four bedrooms, two and a half baths, and a two-car garage. The perfect plan with the perfect color scheme makes this home stand out compare to others that are similar. It provides an open floor plan with great room, dining room, and kitchen with large island. The kitchen features ample counter space, and generous pantry.

    Adriana Sanchez AROD PARTNERS REALTY

    693 Reggie Rd, Winter Haven, FL 33884
  • /15

    $2,200 Per Month

    • 4 Beds
    • 2 Baths
    • 1,856 Sq Ft
    • House for Rent

    2801 Avenue U NW, Winter Haven, FL 33881

    Very Spacious, 4 Bed 2 bath home conveniently located in Winter Haven FL. Home boasts large family room, open kitchen, together with detached work shop and carport!! Get this one while it lasts. Call

    2801 Avenue U NW, Winter Haven, FL 33881
  • /48

    $2,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • House for Rent

    577 Terranova Cir, Winter Haven, FL 33884

    Welcome to this bright and beautifully updated 3-bedroom, 2-bath home located in the desirable gated community of Terra Nova. This property features an open-concept layout, newly installed porcelain tile throughout, and a modern, updated kitchen with clean finishes and excellent natural light. The living areas flow seamlessly, creating an inviting space ideal for entertaining or everyday

    Amanda Nappier DOWNTOWN REALTY

    577 Terranova Cir, Winter Haven, FL 33884
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    $1,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,414 Sq Ft
    • House for Rent

    311 Ave B SE, Winter Haven, FL 33880

    Discover charm and comfort in this adorable 3-bedroom, 2-bathroom home near downtown Winter Haven. Featuring vinyl plank flooring throughout and airy living areas flow seamlessly, ideal for both relaxation and entertaining. Upon entrance you arrive in the spacious living room flowing into the dining area and kitchen. Kitchen equipped with stainless steel appliances and plenty of counter space and

    311 Ave B SE, Winter Haven, FL 33880
  • /23

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • House for Rent

    408 Lake Ned Rd, Winter Haven, FL 33884

    FOR RENT – 3BR / 2BA Home Features a covered back porch, garage workshop, and fenced yard. Conveniently located near a gym, great restaurants, and plenty of shopping.

    Michelle Ellis LA ROSA REALTY PRESTIGE

    408 Lake Ned Rd, Winter Haven, FL 33884
  • /8

    $1,149 Per Month

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

    163 Ave a SE, Winter Haven, FL 33880

    Move In Special---Discover comfortable living in this spacious 854 sq ft 2-bedroom, 1-bath apartment at 163 Avenue A SE, Winter Haven, FL. Featuring modern vinyl flooring, ample natural light with window coverings, and essential conveniences like air conditioning, heat, and a full kitchen equipped with a range, microwave, and refrigerator. Enjoy the convenience of a washer/dryer hookup for your

    163 Ave a SE, Winter Haven, FL 33880
  • /27

    $2,200 Per Month

    • 4 Beds
    • 2 Baths
    • 2,004 Sq Ft
    • House for Rent

    1127 Seedorf Dr, Winter Haven, FL 33881

    Fully Furnished 4BR/2BA Home Built in 2022! Over 2,000 SF of modern living space featuring an open floor plan, gourmet kitchen with quartz island and stainless steel appliances, oversized primary suite, screened lanai, extended paver patio in the backyard, washer & dryer, and 2-car garage. Completely furnished and move-in ready—bring your suitcase!. A rare turnkey rental opportunity at Lake

    Juan Acevedo FORTUNE INTERNATIONAL REALTY

    1127 Seedorf Dr, Winter Haven, FL 33881
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    $2,400 Per Month

    • 5 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • House for Rent

    5002 Strada Dr, Winter Haven, FL 33880

    Must see this very spacious 4/5 bedroom 2.5 bath home with a large office for rent. The home has boasts a very large master bedroom, His and Her closets, over-sized master bathroom with large garden tub and separate shower. Enjoy cooking in the upgraded kitchen together with Granite counters and island. Home has laminate flooring and tile. You will love the 3 car garage, large back yard with

    5002 Strada Dr, Winter Haven, FL 33880
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    $2,150 Per Month

    • 3 Beds
    • 2 Baths
    • 1,426 Sq Ft
    • House for Rent

    265 Meadowbrook Blvd, Winter Haven, FL 33881

    Virtually Staged. Welcome home to this spacious and well-maintained 3-bedroom, 2-bathroom residence in beautiful Polk County, Florida. Featuring an open-concept floor plan, this home offers a bright living area, a modern kitchen with ample cabinet space, and a comfortable dining area perfect for family meals and entertaining. The primary suite includes a private bathroom and generous closet

    Jose Renta MCO MANAGEMENT GROUP LLC

    265 Meadowbrook Blvd, Winter Haven, FL 33881
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    $1,225 Per Month

    • 2 Beds
    • 1 Bath
    • House for Rent

    2371 Edwin St NE, Winter Haven, FL 33881

    LIMITED TIME SPECIAL: Apply and move in by September 15th, receive ONE MONTH FREE! *Restrictions ApplyNice 2BR/1BA duplex conveniently located in Winter Haven! This home features beautiful tile flooring throughout, a refreshed kitchen, and a bright, comfortable layout designed for everyday living. Located within walking distance of local schools and just minutes from shopping,

    2371 Edwin St NE, Winter Haven, FL 33881
  • /15

    $2,100 Per Month

    • 4 Beds
    • 2 Baths
    • 1,853 Sq Ft
    • House for Rent

    643 Grove St, Winter Haven, FL 33881

    A Perfect place + Location that you can CALL HOME 2023 Build. Well-maintained house 4-bedroom, 2-full bath, functional floor plan with generous living areas, comfortable bedrooms, and abundant natural light throughout. The kitchen offers ample cabinet space and flows seamlessly into the main living area, ideal for everyday living and entertaining. Enjoy outdoor living in the fully fenced yard and

    Martha Leighton MIHOUSE REALTY LLC

    643 Grove St, Winter Haven, FL 33881
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    $1,950 Per Month

    • 4 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • House for Rent

    1999 Bretton Ridge Way, Winter Haven, FL 33884

    Welcome home to this beautifully maintained 4-bedroom, 2-bath residence located in the desirable Bretton Ridge community of Winter Haven. This thoughtfully designed home offers an open-concept floor plan perfect for both everyday living and entertaining. The spacious kitchen features granite countertops, rich wood cabinetry, stainless and black appliances, a closet pantry, breakfast bar

    1999 Bretton Ridge Way, Winter Haven, FL 33884
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    $2,495 Per Month

    • 3 Beds
    • 2 Baths
    • 2,116 Sq Ft
    • House for Rent

    252 Santa Rosa Dr, Winter Haven, FL 33884

    Great location. Perfect place to call home. 3 bedroom 2 bath spa/pool home with garage. Located in gated community-overlook estates. Minutes from lego-land. Home offers a kitchen, dining room and a formal dining room. 3rd bedroom has a Murphy bed and built in desk/office area. Master features french doors leading to the pool &spa. Offers walk in closets throughout home. Mature landscaping. Lots

    Jennifer Geiger PRESTIGE LIFESTYLES REALTY

    252 Santa Rosa Dr, Winter Haven, FL 33884
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    $900 Per Month

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

    428 Ave E SE, Winter Haven, FL 33880

    Cute 1-Bedroom, 1-Bathroom Apartment in Winter Haven just minutes from down town!!Lessee(s) are required to provide proof of liability insurance in the amount of $100,000, prior to occupancy. Real Property Management Lakeside can provide the required coverage for an additional charge of $13.00 per month or you can purchase coverage from your preferred provider.To see all of our

    428 Ave E SE, Winter Haven, FL 33880
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    $1,400 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,260 Sq Ft
    • Condo for Rent

    5850 Cypress Gardens Blvd Unit 607, Winter Haven, FL 33884

    Recently updated condo in a great location! Walking distance to Legoland. Featuring 2 bedrooms, 1.5 bathrooms - giving you lots of room and a nice back porch to enjoy on a peaceful Florida afternoon. Call or text to see it today. $50 application fee/person.

    Renee Butler BROKERS REALTY OF CENTRAL FLOR

    5850 Cypress Gardens Blvd Unit 607, Winter Haven, FL 33884
  • /22

    $1,295 Per Month

    • 2 Beds
    • 1 Bath
    • House for Rent

    730 26th St NW, Winter Haven, FL 33881

    ONE MONTH FREE RENT AVAILABLE!* Welcome to this charming 2-bedroom, 1-bathroom property offering you the perfect blend of comfort and convenience, with a spacious layout and inviting living areas providing plenty of room to relax, an a well-equipped kitchen. Enjoy the serene, fenced backyard – perfect for outdoor gatherings or simply unwinding after a long day. Don't miss your chance to make this

    730 26th St NW, Winter Haven, FL 33881
  • /7

    $1,250 Per Month

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • Condo for Rent

    2001 San Marcos Dr SE Unit 11, Winter Haven, FL 33880

    A SPACIOUS GROUND FLOOR END UNIT NEAR FAST FOOD, SHOPPING & BUS LINE. UNIT HAS GAS RANGE & HOT WATER, PLUS GAS HEAT,READY TO MOVE IN NO AGE RESTRICTIONS. CLUB HOUSE & POOL WITH DOCK ON CHAIN OF LAKE.

    William Beasley STAR REALTY OF WINTER HAVEN

    2001 San Marcos Dr SE Unit 11, Winter Haven, FL 33880
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    $1,200 Per Month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • House for Rent

    1610 3rd St NW, Winter Haven, FL 33881

    Charming Newly Renovated 2-Bedroom Home for Rent - Winter HavenWelcome home to this beautifully renovated 2-bedroom, 1-bathroom residence located at 1610 NW 3rd Street, Winter Haven, FL. This move-in-ready home offers a fresh, modern interior with hardwood-style flooring throughout-no carpet-making it both stylish and easy to maintain.The spacious kitchen comes fully equipped with

    1610 3rd St NW, Winter Haven, FL 33881
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    $1,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    145 Beverly Dr, Winter Haven, FL 33884

    Virtually Staged. Here is a beautiful home located just up the street from the Lake Summit boat ramp where you can access the Winter Haven chain of lakes. The home greets you with great curb appeal with mature landscaping, a large driveway, under roof carport and lots of space. You can enter in to the home in to the either the great room or the kitchen where you can enjoy the open concept kitchen

    David Small KELLER WILLIAMS REALTY SMART 1

    145 Beverly Dr, Winter Haven, FL 33884
  • /9

    $1,325 Per Month

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

    430 Ave B NE Unit C, Winter Haven, FL 33881

    ABOUT THE HOMEThis 2 bedroom/1 bathroom is part of a tri-plex and features a massive open living space, luxury vinyl flooring throughout, washer/dryer in the unit, granite countertops, and NO CARPET throughout. Conveniently located close to food, shopping, medical, and just minutes from Downtown Winter Haven, this is a great place to call home!BEFORE SCHEDULINGPlease schedule a

    430 Ave B NE Unit C, Winter Haven, FL 33881
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    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,345 Sq Ft
    • House for Rent

    Unlisted Address

    Beautiful 3-bedroom, 2-bath home available for rent in Winter Haven! This well-maintained property features a spacious open-concept layout with the living and dining areas seamlessly connected to the kitchen, creating the perfect space for everyday living and entertaining. Enjoy a large backyard with plenty of room for outdoor activities, family gatherings, or simply relaxing. Conveniently

    Mirna Hernandez LPT REALTY, LLC

    Unlisted Address
  • /20

    $2,000 Per Month

    • 4 Beds
    • 3 Baths
    • House for Rent

    737 Buccaneer Blvd, Winter Haven, FL 33880

    Lakefront 4-Bedroom Home in Gated The Shores at Lake SearsEnjoy lakefront living at 737 Buccaneer Blvd, a spacious 4-bedroom, 3-bathroom single-family home located in the gated Shores at Lake Sears community of Winter Haven. With approximately 1,995 square feet of living space and a generous lot, this home offers a comfortable layout with room for everyday living, hosting, and relaxing by

    737 Buccaneer Blvd, Winter Haven, FL 33880
  • /18

    $2,150 Per Month

    • 4 Beds
    • 2 Baths
    • 1,852 Sq Ft
    • House for Rent

    5746 Marsh Landing Dr, Winter Haven, FL 33881

    Beautiful 4-bedroom, 2-bath single-family home available for rent beginning in August! This spacious home features an open floor plan, a fully fenced backyard, and a covered screened lanai perfect for relaxing or entertaining.Located in the desirable Lakeside Landings community with access to a community pool, playground, and additional guest parking. Schedule your private showing today!

    Liliec Velasquez NAIM REAL ESTATE LLC

    5746 Marsh Landing Dr, Winter Haven, FL 33881
  • /20

    $2,450 Per Month

    • 3 Beds
    • 2 Baths
    • 1,726 Sq Ft
    • 919 Avenue South Southeast

    919 Ave S SE, Winter Haven, FL 33880

    919 Avenue S SE, Winter Haven, FLWelcome to this charming 1,726 sq ft home in the heart of Winter Haven, Florida—just 9 minutes from LEGOLAND and 40 minutes from Disney World, Universal Studios, and Orlando’s top attractions.This inviting residence features three spacious bedrooms and two beautifully updated bathrooms, offering plenty of space for comfortable family living or a relaxing

    919 Ave S SE, Winter Haven, FL 33880
  • /43

    $2,250 Per Month

    • 4 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • House for Rent

    3139 Laurel Oak Ln, Winter Haven, FL 33884

    Welcome to 3139 Laurel Oak Ln, Winter Haven, FL, a beautiful 4-bedroom, 2-bath home offering over 2,000 square feet of thoughtfully designed living space. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating the perfect space for entertaining or spending time with family. The spacious primary suite features a private bathroom and walk-in closet, while

    Ashley Porto GLASSTONE GROUP INC

    3139 Laurel Oak Ln, Winter Haven, FL 33884
  • /9

    $2,295 Per Month

    • 6 Beds
    • 1 Bath
    • 1,602 Sq Ft
    • House for Rent

    2554 Palm Dr NE, Winter Haven, FL 33881

    LIMITED TIME SPECIAL: Apply and move in by September 15th, receive ONE MONTH FREE! *Restrictions ApplySpacious remodeled 6BR/1BA home in Winter Haven featuring beautiful modern gray LVT wood-style flooring throughout, a comfortable layout, and an oversized den located just off the kitchen for additional living space. The property also offers a large fenced-in backyard and is within

    2554 Palm Dr NE, Winter Haven, FL 33881
  • /10

    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,071 Sq Ft
    • Townhouse for Rent

    308 Ave P NW, Winter Haven, FL 33881

    Be the very first to live in this beautiful brand-new rental! Designed with comfort and privacy in mind, this home features spacious primary suites, each with its own private en-suite bathroom and walk-in closet. Enjoy stylish, modern finishes throughout, a fully fenced yard, and a move-in-ready home with everything brand new. The unique layout is perfect for roommates, a small family, or anyone

    Tess Sultana LA ROSA REALTY PRESTIGE

    308 Ave P NW, Winter Haven, FL 33881
  • /16

    $2,499 Per Month

    • 3 Beds
    • 2 Baths
    • 2,031 Sq Ft
    • House for Rent

    5225 Pebble Beach Blvd, Winter Haven, FL 33884

    Enjoy resort-style living in this beautifully furnished 3-bedroom, 2-bathroom home located in the highly sought-after 55+ gated community of Lake Ashton in Winter Haven. Thoughtfully designed with comfort and elegance in mind, this spacious home offers an open floor plan, upscale finishes, and stunning golf course views.Step inside to find a bright and inviting great room with soaring

    5225 Pebble Beach Blvd, Winter Haven, FL 33884
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    $2,150 Per Month

    • 3 Beds
    • 2 Baths
    • 1,418 Sq Ft
    • House for Rent

    Unlisted Address

    Beautiful 3 Bedroom 2 Bathroom House. Nice community with amenities. Tile floors in open concept, carpet in all rooms.Washer and Dryer included. Playground Available.

    Tania Pinzon LPT REALTY, LLC

    Unlisted Address
  • /16

    $1,995 Per Month

    • 4 Beds
    • 2 Baths
    • 1,855 Sq Ft
    • House for Rent

    616 Sunway Ln, Winter Haven, FL 33880

    Well-kept, 4/2 home for rent, located off Hwy 17. Luxury vinyl plank (LVP) flooring through home. The kitchen has plenty of counter space and opens to the living area as part of an open and spacious floorplan. The master bath has a walk-in shower and a tub. The home has a two-car garage, long driveway and large, partially fenced lot.Washer and dryer not included (hook-up available).

    616 Sunway Ln, Winter Haven, FL 33880
  • /10

    $1,800 Per Month

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

    912 Lake Jessie Dr, Winter Haven, FL 33881

    ** move in special $200 off first month’s rent**The home features 2 bedrooms and 1 bathroom. Even better, utilities are included, making budgeting simple and giving you one less thing to worry about each month. Situated in a peaceful setting with beautiful lake views, this property combines flexibility, comfort, and functionality in a way that's hard to find. Opportunities like this are rare.

    Tiffani Kline HOUSE OF GLASS REAL ESTATE PM

    912 Lake Jessie Dr, Winter Haven, FL 33881
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    $2,050 Per Month

    • 4 Beds
    • 2 Baths
    • 1,846 Sq Ft
    • Coming Soon! Beautiful 4 Bedroom 2 Bathroom Single Family in Winter Haven Gated Community

    1500 Grey Eagle Ln, Winter Haven, FL 33881

    Available for early August move in! Dive into the serene comfort of 1500 Grey Eagle Lane, a charming 4-bedroom, 2-bathroom haven nestled in the heart of Winter Haven, FL. This 1846 sq ft gem offers ample space to create your dream home environment. This spacious home with it's open floorplan is perfect for relaxation and entertaining. The kitchen comes complete with all the necessities including

    1500 Grey Eagle Ln, Winter Haven, FL 33881
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    $1,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,078 Sq Ft
    • Condo for Rent

    2050 San Marcos Dr SE Unit 214, Winter Haven, FL 33880

    Discover a spacious 2-bedroom, 2-bathroom second floor condo nestled in one of the most sought-after complexes in town. This home offers a perfect blend of comfort and convenience, featuring an open floor plan, natural light, and premium finishes throughout. The condo is located right across from the community's office and mailboxes. The two bedrooms provide plenty of space and privacy, with the

    Christin Davis PROPERTY MANAGEMENT OF POLK

    2050 San Marcos Dr SE Unit 214, Winter Haven, FL 33880
  • /11

    $1,200 Per Month

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

    750 Ave C SW Unit 101, Winter Haven, FL 33880

    Come take a look at this newly built 1 bedroom 1 bath apartment located near downtown Winter Haven and a stones throw from Lake Howard. This first floor unit comes with great views, and open concept living, washer and dryer included, and so much more. Water and trash included in rental price. Call today to schedule your showing.All Pro X Property Management The Swain Group. LLC

    750 Ave C SW Unit 101, Winter Haven, FL 33880
  • /19

    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 988 Sq Ft
    • House for Rent

    427 Greenfield Rd, Winter Haven, FL 33884

    This charming two-bedroom, two bathroom situated in a golf community. Located in Cypresswood, a gated community with controlled access and security, this home features an open-concept layout and a kitchen equipped with an island, dishwasher, double-oven range, garbage disposal, and microwave. The primary bedroom boasts a spacious walk-in closet. At the rear of the house, there are two spacious

    Migdalia Moreira PROPERTY OUTLET INTERNATIONAL

    427 Greenfield Rd, Winter Haven, FL 33884
  • /24

    $2,350 Per Month

    • 5 Beds
    • 4 Baths
    • 2,344 Sq Ft
    • House for Rent

    2281 Whitley Ln, Winter Haven, FL 33881

    Step into your new haven at 2281 Whitley Lane, a beautifully crafted 5-bedroom, 4-bathroom residence nestled on a corner lot in the desirable Dundee Station community. Built in 2024, this two-story home offers 2,344 sq ft of heated living space and showcases soaring ceilings, abundant natural light, and refined finishes throughout. The heart of the home features a gourmet kitchen with quartz

    2281 Whitley Ln, Winter Haven, FL 33881

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