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Cypresswood Homes for Rent

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  • /15

    $1,580 per month

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • House for Rent

    2648 Whispering Trails Dr, Winter Haven, FL 33884

    We are currently making final preparations for this home to be available. 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

    2648 Whispering Trails Dr, Winter Haven, FL 33884
  • /35

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft
    • House for Rent

    677 Augusta Rd, Winter Haven, FL 33884

    Welcome to your dream rental home in the prestigious guard-gated community of Cypresswood Golf and Country Club, where luxury living meets resort-style amenities. Nestled within this exclusive enclave, this meticulously crafted 3-bedroom, 2-bathroom home offers an unparalleled lifestyle experience. Upon entering, you're greeted by an inviting ambiance accentuated by high-end finishes and tasteful

    Kayly Malinas JOHN WOOD REALTY, INC.

    677 Augusta Rd, Winter Haven, FL 33884
  • /20

    $1,669 per month

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

    2936 Whispering Trails Dr, Winter Haven, FL 33884

    This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2 bathrooms, and approximately 1,728 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

    2936 Whispering Trails Dr, Winter Haven, FL 33884
  • /8

    $2,050 per month

    • 3 Beds
    • 2 Baths
    • 1,268 Sq Ft
    • House for Rent

    2893 Whispering Trails Dr, Winter Haven, FL 33884

    Modern, elegant and functional: this single residence seamlessly blends the latest in design and technology. Enjoy kitchen, bright and open living spaces, a home office ready for remote work, and privileged access to gated community amenities with a pool. In addition, it features installed solar panels, providing energy savings and a more sustainable lifestyle. Perfect for dynamic families,

    Dailey Duarte Mendez LA ROSA REALTY LLC

    2893 Whispering Trails Dr, Winter Haven, FL 33884
  • /19

    $1,929 per month

    • 4 Beds
    • 2 Baths
    • 2,237 Sq Ft
    • House for Rent

    3013 Whispering Trails Dr, Winter Haven, FL 33884

    Featuring a sparkling community pool!Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,237 square feet, this

    3013 Whispering Trails Dr, Winter Haven, FL 33884
  • /40

    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 1,503 Sq Ft
    • House for Rent

    800 Overlook Grove Dr, Winter Haven, FL 33884

    3/2 2 car garage located in quiet neighborhood on a culdesac, new tile floors, new interior paint. Ready to move in home comes with many upgrades from the original model which include upgraded exterior stone and coach lights, radiant barrier in attic, Spacious master bedroom provides a nice retreat as well as large master bath with dual vanities, whirlpool tub and walk-in shower. Neutral colors

    Oscar Fonseca JEMCO REALTY & PROPERTY MANAGEMENT

    800 Overlook Grove Dr, Winter Haven, FL 33884
  • /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
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    $1,995 per month

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • House for Rent

    668 Grove St, Winter Haven, FL 33884

    Enjoy living in this beautiful one-story home in the Inman Groves Community. The home features 4 bedrooms, 2 baths, with an open floor plan. The floor is all tile, the kitchen has all brand new, stainless-steel appliances and 42” cabinets, and a 2-car garage. A large master suite with a shower, all carpet in bedrooms, and a laundry room with a washer/dryer. The home is approximately 1853 sq ft of

    Amanda Yuan MULTI CHOICE REALTY LLC

    668 Grove St, Winter Haven, FL 33884
  • /20

    $2,039 per month

    • 4 Beds
    • 2 Baths
    • 2,203 Sq Ft
    • House for Rent

    2665 Whispering Trails Dr, Winter Haven, FL 33884

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,203 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents

    2665 Whispering Trails Dr, Winter Haven, FL 33884
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    $2,100 per month

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • House for Rent

    724 Grove St, Winter Haven, FL 33884

    Live in this beautiful brand-new single-family home located in the peaceful and growing community of Inman Grove in Winter Haven! 4 spacious bedrooms and 2 full bathrooms, 2-car garage. Modern open-concept kitchen and living area perfect for entertaining. Great backyard. SS appliances included (fridge, stove, microwave, dishwasher). Window blinds. Enjoy the comfort and convenience of living in a

    Jose Virguez Keller Williams Realty International Lifestyles

    724 Grove St, Winter Haven, FL 33884
  • /15

    $2,165 per month

    • 5 Beds
    • 3 Baths
    • 2,150 Sq Ft
    • House for Rent

    2037 Whispering Trails Blvd, Winter Haven, FL 33884

    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

    2037 Whispering Trails Blvd, Winter Haven, FL 33884
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    $2,600 per month

    • 5 Beds
    • 2.5 Baths
    • 2,254 Sq Ft
    • House for Rent

    930 Cattleman St, Winter Haven, FL 33884

    Welcome to 930 Cattleman St, located in the charming community of Inman Groves in Winter Haven, FL. This spacious Boston model by Lennar offers an ideal blend of comfort, functionality, and modern living. Boasting 5 generously sized bedrooms and 2.5 baths, this two-story home is perfect for families seeking space to grow or investors looking for strong rental potential. The thoughtfully designed

    Carlos Lopez Cadena EXP REALTY LLC

    930 Cattleman St, Winter Haven, FL 33884
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    $1,780 per month

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft
    • House for Rent

    4732 Summerfield Cir, Winter Haven, FL 33881

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    4732 Summerfield Cir, Winter Haven, FL 33881
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    $1,875 per month

    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft
    • House for Rent

    4907 Summerfield Cir, Winter Haven, FL 33881

    Welcome to your new home at 4907 Summerfield Circle Winter Haven, FL 33881!Walk into this 3 bed 2 bath charming home and the first thing you'll notice is the abundance of natural light shining into the kitchen-to-family room combo. The kitchen offers ease & accessibility with all the major appliances including a dishwasher. The master suite is a dream come true with all the storage space

    Marilyn Kuczynski FLORIDA HOMES SALES & MANAGEMENT LLC

    4907 Summerfield Cir, Winter Haven, FL 33881
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    $1,699 per month

    • 3 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • House for Rent

    2110 Whispering Trails Blvd, Winter Haven, FL 33884

    Welcome to your next home in the charming district of Winter Haven, FL. This delightful property perfectly blends comfort and convenience, making it an ideal choice for anyone looking to enjoy a vibrant community lifestyle.Key Property Features include close proximity to several great restaurants and a nearby department store, ensuring daily needs are just a short drive away. For those

    2110 Whispering Trails Blvd, Winter Haven, FL 33884
  • /17

    $1,795 per month

    • 3 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • House for Rent

    2049 Whispering Trails Blvd, Winter Haven, FL 33884

    Nice single-family home with 3 beds and 2 baths for rent in Winter Haven, open floor plan ready to move in, Washer and Dryer included.Don't miss out on the opportunity to make this beautiful unit your new home. Contact us today to schedule a showing!FCG REALTY residents are enrolled in the Resident Benefits Package (RBP) which includes a convenient option for renters insurance, HVAC

    Amber Madera FCG REALTY

    2049 Whispering Trails Blvd, Winter Haven, FL 33884
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    $4,500 per month

    • 3 Beds
    • 3 Baths
    • 2,541 Sq Ft
    • House for Rent

    1781 Lake Hill Dr, Winter Haven, FL 33884

    NEW CONSTRUCTION! Beautiful brand new 3-bedroom/3-bathroom home with additional bonus room ideal for an office, den, gym, or play room in the prestigious Woodpointe community of SE Winter Haven! Elegant custom and designer finishes throughout, screened lanai, walk-in closets, open-concept and split-bedroom floor plan, and so much more. Applications evaluated on creditworthiness and income equal

    Kayly Malinas JOHN WOOD REALTY, INC.

    1781 Lake Hill Dr, Winter Haven, FL 33884
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    $1,475 per month

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

    1406 Eagle Pond Dr Unit 14F, Winter Haven, FL 33884

    Second-floor two-bedroom, two-bathroom condo located in the gated golf community of Cypresswoods. Condo features inside laundry, upgraded kitchen, storage room and spacious living room. Enjoy the numerous HOA amenities including a private gated entrance with 24/7 guard, pool, gym, tennis courts, and golf. Home available immediately.

    Sharon Billups SKYELINE REALTY LLC

    1406 Eagle Pond Dr Unit 14F, Winter Haven, FL 33884
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    $1,700 per month

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

    2956 Whispering Trails Dr, Winter Haven, FL 33884

    NEW IMPROVED PRICE for this 3 Bedroom, 2 Bathroom Home for rent in a Gated Community, just minutes from Legoland! This 1,500 sq. ft. rental home is ready for its new tenant(s)! Nestled in the highly desirable Whispering Trails community, this property offers a spacious open layout with a split floorplan, spacious living room, and a large kitchen featuring an oversized island and breakfast

    Kim Connahey HOUSE OF GLASS REAL ESTATE PM

    2956 Whispering Trails Dr, Winter Haven, FL 33884
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    $1,900 per month

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • House for Rent

    2900 Whispering Trails Dr, Winter Haven, FL 33884

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable gated community of Whispering Trails. Built in 2017 and ideally situated just minutes from Hwy 27, this home offers both comfort and convenience.Step inside to a spacious open floorplan featuring sleek, low-maintenance contemporary concrete flooring and a large kitchen with stainless steel appliances

    Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

    2900 Whispering Trails Dr, Winter Haven, FL 33884
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    $1,995 per month

    • 3 Beds
    • 2 Baths
    • 1,998 Sq Ft
    • House for Rent

    553 Saint Andrews Rd, Winter Haven, FL 33884

    This three bedroom, two bathroom home is located in the gated Cypresswood golf subdivision. Enjoy the numerous HOA amenities, including a private gated community entrance with 24/7 guard, pool, fitness center, tennis courts, and golf. Home features a split floor plan, updated kitchen with stainless steel appliances and a gas range, brand new carpet in bedrooms, an enclosed sunroom that overlooks

    Sharon Billups SKYELINE REALTY LLC

    553 Saint Andrews Rd, Winter Haven, FL 33884
  • /13

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft
    • Apartment for Rent

    13 Enclave Dr, Winter Haven, FL 33884

    Welcome to this maintained 3 bedroom, 2 bath one-story villa/townhouse located in Enclave, a quiet and desirable neighborhood within the gated golf community of Cypresswood Golf & Country Club. This spacious end-unit features a functional split-bedroom floor plan, generous living and dining areas, and an inviting Florida room that adds to the overall living space. The kitchen offers ample cabinet

    Suzanna Rudd KELLER WILLIAMS REALTY SMART 1

    13 Enclave Dr, Winter Haven, FL 33884
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    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,511 Sq Ft
    • House for Rent

    2700 Crump Rd, Winter Haven, FL 33881

    Lakefront Living at Its Finest!Discover the perfect blend of comfort, convenience, and stunning natural beauty with this 3-bedroom, 2-bath home located on the highly sought-after Lake Hamilton. This property offers unbeatable location — just minutes from shopping, dining, and entertainment, yet far enough to enjoy peace and privacy away from the city bustle.Recently updated, this home delivers

    Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

    2700 Crump Rd, Winter Haven, FL 33881
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    $2,200 per month

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • House for Rent

    3240 Country Walk Club Cir, Winter Haven, FL 33881

    Brochure Available, Docs Available, Floor Plan Available

    Moises Dominguez, LLC TBO REAL ESTATE PARTNERS INC

    3240 Country Walk Club Cir, Winter Haven, FL 33881
  • /3

    $3,400 per month

    • 5 Beds
    • 3 Baths
    • 2,845 Sq Ft
    • House for Rent

    740 Grove St, Winter Haven, FL 33881

    Nestled in the serene location of Winter Haven; beautiful house conveniently located near Lego Land. 5 bedrooms, 3 bathrooms, 2-car garage, stainless steel appliances. Fenced-in backyard offering space and privacy. Includes smart home technology so that you can connect to your home via smartphone. Enjoy Winter Haven's main attractions and sights such as boating on the Chain of Lakes and Antique

    Claudia Pulgarin Capital Nest Realty, LLC

    740 Grove St, Winter Haven, FL 33881
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    $2,700 per month

    • 5 Beds
    • 3 Baths
    • 2,601 Sq Ft
    • House for Rent

    420 Chance Ave, Winter Haven, FL 33881

    FOR RENT! 5 BEDROOMS + FORMAL DINING + FAMILY ROOM AMD 3 FULL BATHROOMS, ONE BEDROOM AND FULL BATHROOM ON THE FIRST FLOOR. KITCHEN HAS A LARGE ISLAND WITH GRANITE , APPLIANCES INC. DISHWASHER, STOVE AND RANGE. SPACIOUS LIVING & DINING ROOM GREAT FOR ENTERTAINING, AND SO MUCH MORE. EXTRA LARGE BACKYARD. Find everything you need in Winter Haven! Located just minutes from world class theme parks and

    Alaina Edmondson COAST TO COAST REAL ESTATE PRO

    420 Chance Ave, Winter Haven, FL 33881
  • /24

    $1,600 per month

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

    1005 Eagle Pond Dr, Winter Haven, FL 33884

    MOVE-IN READY Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club available beginning 12/1/2023. This meticulously-maintained condo features hard floors throughout (no carpet!), new interior paint, NEW kitchen appliances, interior laundry (with brand new front load LG washer/dryer provided), and so much more. The spacious master bedroom features an

    Kayly Malinas JOHN WOOD REALTY, INC.

    1005 Eagle Pond Dr, Winter Haven, FL 33884

Why Live in Cypresswood

Cypresswood in Winter Haven is a master-planned community known for its golf courses and country club amenities. With over 1,000 residential units and 14 neighborhood associations, it offers diverse housing options, primarily ranch-style homes from the 1980s to early 2000s, with new custom builds still emerging. The Cypresswood Golf & Country Club, featuring the best golf course in Winter Haven for 2023, is a central attraction. Residents enjoy country club amenities, including pools, gyms, and tennis courts, with plans to add pickleball courts. The neighborhood is close to shopping and dining, with a Winn-Dixie within 2 miles and a Walmart Supercenter under 6 miles away. Local dining includes the Cypresswood Pub, Legacy Craft BBQ, and Dundee Diner. For outdoor activities, the nearby Michael V. Lewis Arboretum and Parrott Trail offer 42 acres of native and exotic plants. Cypresswood is under 5 miles from Legoland and less than 30 minutes from Disney World, with both east and west coast beaches about 2 hours away. The neighborhood is zoned for Polk County Public Schools, one of the top 50 districts in Florida. Public transportation is not available, so residents rely on cars or golf carts, with major routes like US Highway 27 and Florida State Road 60 nearby. Orlando International Airport is about 45 miles away.
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