Cypresswood Homes

• 

  

  

  /24

  $390,000

  • 5 Beds
  • 3 Baths
  • 2,696 Sq Ft

  814 Turner Ln, Winter Haven, FL 33881

  Welcome to 814 Turner Lane, a beautifully upgraded Hayden model by D.R. Horton located in the heart of Winter Haven! ?? This spacious two-story home offers 5 bedrooms, 3 full bathrooms, and over 2,500 sq. ft. of living space, making it the perfect choice for families or anyone seeking extra room to spread out. Built with quality craftsmanship and thoughtful design, the Hayden model is known for

  

  Rafael Ortiz

  KELLER WILLIAMS LEGACY REALTY

  (863) 375-8538

  814 Turner Ln, Winter Haven, FL 33881
• 

  Explore Cypresswood

• 

  

  

  /15

  $1,550 per month

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

  2648 Whispering Trails Dr, Winter Haven, FL 33884

  Please note that the advertised price may exclude additional fees. These include a mandatory $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; fees for amenities like smart home or internet service; and optional conditional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99), pet fees/rent, or pool

  2648 Whispering Trails Dr, Winter Haven, FL 33884
• 

  

  /2

  $170,000 Sold Sep 15, 2025

  • 1,017 Sq Ft
  • $167/SF
  • 6 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  705 Eagle Pond Dr, Winter Haven, FL 33884

  Beautifully remodeled condo in serene golf community! One of the only units offering ceramic tile floors, granite countertops, and a private laundry room. Enjoy views of rocket launches from the dining room—yes, really! The A/C was replaced in 2015, and the original water heater remains in excellent condition. HOA covers exterior maintenance and more. Priced aggressively for the upgrades—don’t

  JP Gutierrez EXP REALTY LLC

  705 Eagle Pond Dr, Winter Haven, FL 33884
• 

  

  /2

  Est $331,287 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,966 Sq Ft

  3224 Oak Tree Ln, Winter Haven, FL 33884

  3224 Oak Tree Ln, Winter Haven, FL 33884
• 

  

  

  /54

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,622 Sq Ft

  560 Saint Andrews Rd, Winter Haven, FL 33884

  Welcome to 560 St Andrews Rd in Cypresswood Golf & Country Club!This beautiful patio home is truly move-in ready, offering 2 bedrooms, 2 bathrooms, and plenty of stylish updates.From the moment you arrive, you’ll be impressed by the brick-paver driveway, lush landscaping, and inviting curb appeal. Inside, the spacious living, dining, and kitchen areas feature wood-look ceramic tile floors, adding

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  560 Saint Andrews Rd, Winter Haven, FL 33884
• 

  

  /14

  $1,200 per month

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

  2924 Whispering Trails Dr, Winter Haven, FL 33884

  Some pictures are virtual furniture. Modern Studio 1-Bedroom, 1 bath rental, – All Utilities Included! This Next Gen-style unit features a private entrance, walking closet, private screen porch, small kitchen, laundry, and private parking. Enjoy A/C, high-speed internet, electricity, water, trash, channel and yard care—all included in rent. Located in a quiet gated winter Haven community with

  maritza monzon INTERNATIONAL EXECUTIVE REALTY

  2924 Whispering Trails Dr, Winter Haven, FL 33884
• 

  /2

  $315,000 Sold Sep 12, 2025

  • 2,136 Sq Ft
  • $147/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  740 Canberra Rd, Winter Haven, FL 33884

  Well maintained 3 bedroom, 2 bath, 2,136 SF heated space, 2 car garage home in the Cypresswood Golf Community in Winter Haven for sale. Move In Ready! Wow, the floor plan is awesome - nice spacious rooms - lots of storage closets in this home. Split floor plan, pocket doors between dining rm & family rm, sliding doors to the back porch. Updates in Kitchen & Bathrooms, Windows, Flooring, AC and

  Cheryl Skinner-Marble XCELLENCE REALTY, INC

  740 Canberra Rd, Winter Haven, FL 33884
• 

  

  /23

  Est $324,114 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft

  2972 Whispering Trails Dr, Winter Haven, FL 33884

  2972 Whispering Trails Dr, Winter Haven, FL 33884
• 

  

  /69

  $385,000

  • 5 Beds
  • 2.5 Baths
  • 2,254 Sq Ft

  950 Cattleman St, Winter Haven, FL 33884

  Welcome to this charming corner lot home in the heart of Winter Haven! Featuring a bright and open floor plan, this residence offers comfortable living with modern touches throughout. The spacious kitchen seamlessly connects to the dining and living areas, making it ideal for both everyday living and entertaining. Retreat to the primary suite with its own private bath, while additional bedrooms

  Gisele Abrantes Trautman SERHANT

  950 Cattleman St, Winter Haven, FL 33884
• 

  

  /16

  $1,859 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! 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 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

  3013 Whispering Trails Dr, Winter Haven, FL 33884
• 

  /2

  $440,000 Sold Sep 12, 2025

  • 2,667 Sq Ft
  • $165/SF
  • 13 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1976

  351 Greenfield Rd, Winter Haven, FL 33884

  SPACE FOR EVERYONE! COUNTRY CLUB LIFESTYLE!! Huge four bedroom, three full bath POOL home on .52 acres! Lot overlooks the 13th tee in the private, guard-gated 24/7 golf community of Cypresswood Golf & Country Club. Beautiful brick wood-burning fireplace in family room plus a large bonus room that was being used as a game and theater room - a great spot!! The kitchen features quartz countertops

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  351 Greenfield Rd, Winter Haven, FL 33884
• 

  

  /80

  Est $502,339 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft

  1877 Woodpointe Dr, Winter Haven, FL 33884

  1877 Woodpointe Dr, Winter Haven, FL 33884
• 

  

  /36

  $379,999

  • 3 Beds
  • 2 Baths
  • 2,159 Sq Ft

  718 Canberra Rd, Winter Haven, FL 33884

  Elevated Living on the Fairway – Fully Renovated & ReadyWelcome to 718 Canberra Road—where luxury living meets peace of mind. This completely renovated 3-bedroom, 2-bathroom home spans 2,159 sq ft and overlooks the 17th fairway of the prestigious Cypresswood Golf Course, offering stunning views from your sun-drenched enclosed Florida room.No detail was overlooked in this 2021-to-2025

  Veronica Bard LA ROSA REALTY PRESTIGE

  718 Canberra Rd, 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

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  2037 Whispering Trails Blvd, Winter Haven, FL 33884
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  /2

  $283,300 Sold Sep 10, 2025

  • 2,242 Sq Ft
  • $126/SF
  • 559 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  1856 Emily Dr, Winter Haven, FL 33884

  The Perfect Home for 2025! Owner motivated. Located in a established neighborhood with great access to Lego Land, "A" schools, shopping and entertainment. This lovely home includes plenty of bonus space for a growing family; 4 bedrooms, 2.5 bathrooms and possible bonus room, this home has it all. The formal dining room at the front leads to the spacious eat-in kitchen, which includes a center

  Barbara Jackson MILLENNIUM REALTY CENTER LLC

  1856 Emily Dr, Winter Haven, FL 33884
• 

  /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
• 

  

  /14

  $334,900

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft

  3132 Country Club Cir, Winter Haven, FL 33881

  This home is located in the awesome Lake Region of Winter Haven. In a very desired area of right off Dundee road onto Country Club. Central to everything! Minutes away from Legoland & 45 min to Tampa or all of the Orlando attractions and close to downtown Winter Haven area, shopping, several lakes and travel.! This meticulously 4 Bedroom,2 bath, over 1828 sf., split floor plan have ceramic tiled

  Irma Cruz FLORIDA REALTY MARKETPLACE

  3132 Country Club Cir, Winter Haven, FL 33881
• 

  

  /16

  $1,705 per month

  • 3 Beds
  • 2 Baths
  • 1,303 Sq Ft
  • House for Rent

  3119 Whispering Trails St, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  3119 Whispering Trails St, Winter Haven, FL 33884
• 

  /2

  $435,000 Sold Sep 04, 2025

  • 2,494 Sq Ft
  • $174/SF
  • 274 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  1935 Austin Terrace, Winter Haven, FL 33884

  NEW ROOF PRIOR TO CLOSING! Nestled in the heart of Winter Haven, this exquisite residence beckons those with a penchant for refined living. This architectural gem, a custom-built haven, stands proudly in a gated community, offering an unparalleled blend of luxury and tranquility.As you approach the property, you'll be captivated by the mature landscaping that frames this

  Yevette Eden LA ROSA REALTY PRESTIGE

  1935 Austin Terrace, Winter Haven, FL 33884
• 

  

  /24

  Est $247,401 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,262 Sq Ft

  2960 Whispering Trails Dr, Winter Haven, FL 33884

  2960 Whispering Trails Dr, Winter Haven, FL 33884
• 

  

  /65

  $395,000

  • 5 Beds
  • 3 Baths
  • 2,696 Sq Ft

  623 Grove St, Winter Haven, FL 33881

  Welcome to Inman Grove a prime location just minutes from Legoland, Hwy 27, top-rated schools, shopping, medical facilities, and popular dining options! This spacious 5-bedroom, 3-bathroom Hayden model offers both comfort and functionality, including a first-floor bedroom and full bath perfect for guests or multigenerational living. The home features a formal dining room, large family room, and

  Victoria Escobar KELLER WILLIAMS SUBURBAN TAMPA

  623 Grove St, Winter Haven, FL 33881
• 

  

  /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
• 

  /2

  $329,000 Sold Sep 03, 2025

  • 2,048 Sq Ft
  • $161/SF
  • 107 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  409 Greenfield Rd, Winter Haven, FL 33884

  Stop scrolling—this is the one. Welcome to 409 Greenfield Rd, a beautifully updated move-in-ready home tucked inside the sought-after gated community of Cypresswood. This home is 100% vacant and ready for you to tour today.Step inside and immediately feel the difference—brand new luxury vinyl plank flooring, fresh interior paint, and a bright, open layout that feels like home from the

  Chad Lindsey KELLER WILLIAMS REALTY SMART 1

  409 Greenfield Rd, Winter Haven, FL 33884
• 

  

  /28

  Est $247,543 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  4815 Summerfield Cir, Winter Haven, FL 33881

  4815 Summerfield Cir, Winter Haven, FL 33881
• 

  

  /38

  $360,000

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

  271 Inman Blvd, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. PRICE IMPROVEMENT, BEST VALUE IN INMAN GROVES! Welcome Home to 271 Inman Blvd, a brand new home built in 2024 that still retains that fresh, new house smell. Located in the vibrant new micro-community of Inman Groves, this home offers the convenience of living in a brand new home without the hassle of waiting for construction to be completed. Step

  Randy Crews BHHS FLORIDA PROPERTIES GROUP

  271 Inman Blvd, Winter Haven, FL 33881
• 

  

  /17

  $2,395 per month

  • 5 Beds
  • 2.5 Baths
  • 2,215 Sq Ft
  • House for Rent

  640 Grove St, Winter Haven, FL 33884

  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.

  640 Grove St, Winter Haven, FL 33884
• 

  /2

  $360,000 Sold Aug 31, 2025

  • 3,050 Sq Ft
  • $118/SF
  • 23 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2006

  1800 Emily Dr, Winter Haven, FL 33884

  LUXURY... COMFORT...SPACE! This beautifully well maintained piece of paradise is located on a huge corner lot ( 0.23 acres) in the desirable community of Emily Estates. With 5 bedrooms, 3.5-baths, this expansive home offers 3050 sq ft of living space and is perfectly designed for any family who loves to entertain and enjoy luxurious living. The home has been extensively upgraded with custom tile,

  Twanna Dewdney LA ROSA REALTY PRESTIGE

  1800 Emily Dr, Winter Haven, FL 33884
• 

  

  /39

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  503 Leyland Cypress Way, Winter Haven, FL 33881

  503 Leyland Cypress Way, Winter Haven, FL 33881
• 

  

  /24

  $306,999

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft

  3017 Country Club Cir, Winter Haven, FL 33881

  Welcome to this beautifully maintained, newer 3-bedroom, 2-bathroom home featuring a desirable open-concept layout and a split floor plan for added privacy. Enjoy a modern kitchen equipped with granite countertops, stainless steel appliances, and a spacious island perfect for entertaining. The main living areas boast tile flooring, combining style with easy maintenance.Step outside to a

  Laura Armstrong KELLER WILLIAMS REALTY SMART

  3017 Country Club Cir, Winter Haven, FL 33881
• 

  

  /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
• 

  /2

  $127,000 Sold Aug 29, 2025

  • 1,017 Sq Ft
  • $125/SF
  • 135 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2006

  507 Eagle Pond Dr Unit G5, Winter Haven, FL 33884

  FOR SALE - 2 Bedroom/2 Bath Condo in lovely Cypresswood Gulf and Country Club. This condo overlooks a pond and beautiful cypress trees. It is very peaceful and serene. Then, the grounds are gorgeous as they are meticulously maintained for the golf courses. Everywhere one looks is a beautiful sight. The condo itself is very comfortable with generously sized bedrooms and walk-in closets. All

  Linda Andre COLDWELL BANKER REALTY

  507 Eagle Pond Dr Unit G5, Winter Haven, FL 33884
• 

  

  /53

  Est $241,991 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,253 Sq Ft

  3268 Whispering Trails Ave, Winter Haven, FL 33884

  3268 Whispering Trails Ave, Winter Haven, FL 33884
• 

  

  /24

  $329,990

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft

  3308 Country Walk Club Cir, Winter Haven, FL 33881

  In a vibrant neighborhood, a stunning home built in 2020 awaits. With four spacious bedrooms and two beautifully designed bathrooms, this residence offers comfort and elegance, perfect for families. As you enter, the expansive open floor plan welcomes you. The kitchen features rich espresso-colored cabinets and gleaming granite countertops, complemented by top-of-the-line stainless-steel

  Humberto Cuevas LA ROSA REALTY LLC

  3308 Country Walk Club Cir, Winter Haven, FL 33881
• 

  

  /20

  $1,989 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. 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 2,203 square feet, this well-maintained home offers a high standard of

  2665 Whispering Trails Dr, Winter Haven, FL 33884
• 

  /2

  $975,000 Sold Aug 14, 2025

  • 4,021 Sq Ft
  • $242/SF
  • 14 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2018

  1836 Woodpointe Dr, Winter Haven, FL 33884

  Tucked inside one of Winter Haven’s most sought-after gated communities, this custom-built lakefront estate on the sparkling, spring-fed Lake Daisy is the ultimate expression of lakeside luxury. Spanning over half an acre, this 2018 modern masterpiece effortlessly blends clean architectural lines with the warmth of modern pastoral design—crafted for those who crave elegance, privacy, and the

  Kayly Malinas JOHN WOOD REALTY, INC.

  1836 Woodpointe Dr, Winter Haven, FL 33884
• 

  

  /10

  Est $284,290 Not Listed For Sale

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

  1417 Austin Terrace, Winter Haven, FL 33884

  1417 Austin Terrace, Winter Haven, FL 33884
• 

  

  /43

  $332,500

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  708 Canberra Rd, Winter Haven, FL 33884

  Welcome to your dream retreat! This stunning 3-bedroom, 2-bathroom home is perfectly nestled in a tranquil cul-de-sac within a highly sought-after gated golfing neighborhood, just minutes from the excitement of Legoland. This property offers an ideal blend of an active lifestyle and serene living, making it perfect for families and those seeking relaxation.As you step inside, you'll be

  David Small KELLER WILLIAMS REALTY SMART 1

  708 Canberra Rd, Winter Haven, FL 33884
• 

  

  /40

  $1,850 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
• 

  /2

  $245,000 Sold Aug 11, 2025

  • 1,262 Sq Ft
  • $194/SF
  • 87 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2017

  2792 Whispering Trails Dr, Winter Haven, FL 33884

  This 3-bedroom, 2-bathroom home is located in the gated Whispering Trails community and offers a distinctive design with unique floor tiles throughout. The open layout provides a spacious feel, while the well-sized bedrooms ensure comfort and functionality.The kitchen is equipped with modern appliances, making meal preparation easy and efficient. The home’s thoughtful design allows for

  Gladys Burgos FCG REALTY

  2792 Whispering Trails Dr, Winter Haven, FL 33884
• 

  

  /10

  Est $305,717 Not Listed For Sale

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

  1466 Austin Terrace, Winter Haven, FL 33884

  1466 Austin Terrace, Winter Haven, FL 33884

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