Cypresswood Homes for Sale

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  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  10 Webb Rd, Winter Haven, FL 33881

  Live On-Site Auction | Secluded 4-BD Ranch on 5 AC with Pool, Barns & Country Charm10 Webb Rd. Winter Haven, FL 33881Bidding Ends: September 13th at 11 AMPrivate 4BR/2.5BA ranch on 5 acres in East Winter Haven! Enjoy 2,000 sq ft, pool, screened porch, fireplace, and 2 barns. Former citrus grove with no HOA or flood zone. Peaceful setting at roads end, yet close to Hwy 27, I-4, and

  Marty Higgenbotham

  10 Webb Rd, Winter Haven, FL 33881
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  Explore Cypresswood

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  $425,000

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  35 Vagabond Ln, Winter Haven, FL 33881

  Charming & Unique Florida Cracker-Style Home on Nearly an Acre!Welcome to this one-of-a-kind 3-bedroom, 2-bath Florida “cracker” home, nestled on a beautifully landscaped .96-acre lot in a quiet, private cul-de-sac. Brimming with character, this home offers timeless style, comfort, and the peaceful charm of Old Florida living.Step inside to discover gorgeous wood floors

  Kristi Donay HOMETRUST REAL ESTATE & PTY MGT

  35 Vagabond Ln, Winter Haven, FL 33881
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  $339,000

  • 3 Beds
  • 2 Baths
  • 2,136 Sq Ft

  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
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  $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
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  $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
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  $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
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  $350,000

  • 4 Beds
  • 3.5 Baths
  • 3,050 Sq Ft

  1905 Emily Blvd, Winter Haven, FL 33884

  Welcome to your new dream home! This spacious 4-bedroom, 3.1-bathroom gem spans over 3,000 square feet, offering ample room for comfort and creativity. Nestled in a vibrant, family-friendly community, this two-story haven boasts a BRAND-NEW ROOF, ensuring worry-free living for years to come. ADDITIONAL UPDATES: TOILETS WERE UPGRADED, KITCHEN CABINETS PAINTED, SECOND FLOOR FLOORING, GARAGE

  Roselin Diaz ELITE REALTY, LLC

  1905 Emily Blvd, Winter Haven, FL 33884
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  $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
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  $325,000

  • 3 Beds
  • 2 Baths
  • 1,603 Sq Ft

  380 Niblick Cir, Winter Haven, FL 33881

  New Price Alert! We've just adjusted the price on this beautiful home—making it an even better value. Plus, take advantage of an Assumable VA Loan for qualified buyers at an incredible 5.375% interest rate—offering significant savings. Welcome to The Gates of Lake Region, a beautifully manicured and highly desirable community offering tranquil living in a prime location. This thoughtfully

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  380 Niblick Cir, Winter Haven, FL 33881
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  $334,500

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft

  296 Inman Blvd, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Built in 2023 and move-in ready for you and your family to begin enjoying your new home! Welcome to this beautiful 3 bedroom, 2 bathroom, 2-car garage home. Step inside and enjoy the luxury of having a split floorplan with the two bedrooms and additional bathroom in the front of the home and the primary bedroom with ensuite bathroom on the opposite

  Kevin Asenjo COLDWELL BANKER RESIDENTIAL RE

  296 Inman Blvd, Winter Haven, FL 33881
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  $327,000

  • 2 Beds
  • 2 Baths
  • 1,922 Sq Ft

  560 Saint Andrews Rd, Winter Haven, FL 33884

  Immaculate POOL HOME in CYPRESSWOOD – Fully Renovated & Located in a gated golf community!!! Welcome to your dream home in the highly desirable Cypresswood community! This beautifully updated residence features a new roof, stylish wood-look tile flooring throughout, and a completely remodeled kitchen equipped with Wi-Fi-enabled Samsung appliances—perfect for modern living and effortless

  Brooklyn Paul BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

  560 Saint Andrews Rd, Winter Haven, FL 33884
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  $360,000

  • 4 Beds
  • 3 Baths
  • 2,093 Sq Ft

  808 Overlook Grove Dr, Winter Haven, FL 33884

  Sparkling 4 bedroom, 3 bath home located on a quiet cul-de-sac with no rear neighbors. This spacious split-bedroom plan offers over a quarter-acre premium lot and is in excellent move-in condition. Features include granite countertops, a large open kitchen with stainless steel appliances, breakfast bar, closet pantry, and an 18-inch solar tube for natural light. The kitchen opens to a huge family

  Becky Norman AT HOME REALTY

  808 Overlook Grove Dr, Winter Haven, FL 33884
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  $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
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  $350,000

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft

  811 Turner Ln, Winter Haven, FL 33881

  This home features a spacious open floor plan, ideal for cooking in the kitchen while entertaining family and friends. The large master bedroom boasts a generous walk-in closet. Located just minutes from world-renowned theme parks and attractions, Inman Groves offers the perfect blend of convenience and Florida’s vibrant lifestyle. Enjoy stunning local lakes right in your backyard, and take

  Yanira Suarez LPT REALTY, LLC

  811 Turner Ln, Winter Haven, FL 33881
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  $425,000

  • 3 Beds
  • 2.5 Baths
  • 2,494 Sq Ft

  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
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  $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
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  $349,900

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  416 Sandestin Dr, Winter Haven, FL 33884

  UPSCALE HOME IN CYPRESSWOOD GOLF COMMUNITY. Beautifully remodeled and ready for the discerning buyer. Large 3 BR/2BA patio home located in beautiful Cypresswood Golf Community. This home features updated gourmet kitchen, remodeled baths, newer roof, whole house Generac generator, natural gas instant hot water heater, new refrigerator 2022, new gas range, Bosch dishwasher, real wood/bamboo

  Sharon Watson CENTURY 21 WATSON & MYERS REALTY

  416 Sandestin Dr, Winter Haven, FL 33884
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  $385,000 New Construction

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

  934 Cattleman St, Winter Haven, FL 33884

  Stunning 5BR/2.5BA single family home on an oversized lot in the sought-after Inman Groves community. Move-in-ready home offers 2,215sq. ft. of thoughtfully designed living space with high ceilings, tile/carpet floors, and an open-concept layout. The kitchen features a spacious island and flows into the expansive family room. Upstairs, the owner’s suite includes a large walk-in closet and

  Cristina de Oliveira Miami New Realty

  934 Cattleman St, Winter Haven, FL 33884
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  /31

  $279,900

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft

  14 Enclave Dr, Winter Haven, FL 33884

  Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven.The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  14 Enclave Dr, Winter Haven, FL 33884
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  $200,000

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft

  1606 Eagle Pond Dr, Winter Haven, FL 33884

  This is Eagle Pond, a beautiful section of the Cypress Woods Golf and Country Club. This secure, gated community offers around-the-clock security for added peace of mind. Situated on the second floor, this condo showcases impressive 10-foot ceilings and a spacious open layout. It features two bedrooms, walk-in closets, ceiling fans and the primary bedroom includes a private ensuite bath. The

  Juan Yglesias KELLER WILLIAMS REALTY SMART 1

  1606 Eagle Pond Dr, Winter Haven, FL 33884
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  $195,900

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft

  307 Eagle Pond Dr, Winter Haven, FL 33884

  This beautiful second-floor Eagle Pond condo in the 24/7 guard-gated Cypresswood Golf & Country Club offers peaceful pond views you’ll love, visible from both bedrooms and the living room. With tall 10-foot ceilings and warm wood cabinets, the open living and dining area flows right into the breakfast bar kitchen, perfect for relaxing or hosting friends. Both bedrooms have roomy walk-in closets,

  Mabel Vassallo CENTURY 21 MYERS REALTY

  307 Eagle Pond Dr, Winter Haven, FL 33884
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  $474,900

  • 4 Beds
  • 3 Baths
  • 2,781 Sq Ft

  1908 Crossroads Blvd, Winter Haven, FL 33881

  Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive, you’re welcomed by a

  Jill Lingenfelter CENTURY 21 MYERS REALTY

  1908 Crossroads Blvd, Winter Haven, FL 33881
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  $460,000

  • 4 Beds
  • 3 Baths
  • 2,667 Sq Ft

  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
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  $112,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  203 Monterey Cypress Blvd Unit 174, Winter Haven, FL 33881

  **Charming Waterfront Retreat in Florida!** NEW ROOF 2025! Discover your dream home with this stunning 2008 Fleetwood model that boasts breathtaking views of a serene lake. Imagine sipping your morning coffee while watching Florida's vibrant birds from your cozy dining area or spacious living room. This meticulously maintained residence features an inviting vinyl-windowed Florida room, perfectly

  Tanya Johnston American Mobile Home Sales of Tampa Bay, Inc.

  203 Monterey Cypress Blvd Unit 174, Winter Haven, FL 33881
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  $199,500

  • 3 Beds
  • 3 Baths
  • 1,988 Sq Ft

  440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881

  Lot #97 / 3 B / 3 BA / 1,988 Sq. Ft. / $199,500.00 Spectacular Home! Completely Remodeled 2009 Erica Model in popular Cypress Creek Village! This large home is located on a spacious corner lot. It has a double carport with extra covered golf cart parking. Professionally remodeled upgrades include: - New Architectural Shingle Roof - New Air Conditioner and New Mr. Cool a/c for the tiled

  Jennifer Meyers CRF Communities

  440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881
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  $159,900

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  312 Siberian Cypress Cir Unit 326, Winter Haven, FL 33881

  LUXURY Finishes - IMMACULATE Condition - NO Rear NEIGHBORS - 1,568 Sq. Ft. of Beautiful Living Space Welcome to CYPRESS CREEK VILLAGE, one of Central Florida's NEWEST 55+ active ADULT, PET-FRIENDLY communities, where lifestyle comes first. Located in WINTER HAVEN, Florida this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $685, which includes

  Tammy Barnhart Renee's Resales

  312 Siberian Cypress Cir Unit 326, Winter Haven, FL 33881
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  $205,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  2282 Firestone Place, Winter Haven, FL 33884

  Welcome to Cypresswood Golf & Country Club Living!Discover this charming 2-bed, 2-bath, single-story Golf Villa at 2282 Firestone Pl in the exclusive gated community of Cypresswood in Winter Haven, FL. Boasting 1,164 sq ft of thoughtfully designed living space, this villa offers the perfect blend of comfort, style, and sweeping golf course views.Key Features & Upgrades:Two inviting

  Juan Yglesias KELLER WILLIAMS REALTY SMART 1

  2282 Firestone Place, Winter Haven, FL 33884
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  $770,000

  • 4 Beds
  • 2.5 Baths
  • 2,001 Sq Ft

  10 Webb Rd, Winter Haven, FL 33881

  Secluded 4-Bedroom Ranch on 5 Acres with Pool, Barns & Country Charm! Discover the perfect blend of privacy, convenience, and space with this 4 bedroom, 2.5 bath ranch-style home nestled on 5 acres in East Winter Haven. Tucked away at the end of a quiet road, this former citrus grove offers a peaceful, no-HOA lifestyle with plenty of room for your family, animals, and hobbies. Built in 1979, the

  Martin E Higgenbotham HIGGENBOTHAM AUCTIONEERS INTERNATIONAL LTD INC

  10 Webb Rd, Winter Haven, FL 33881
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  $139,900

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  336 Monterey Cypress Blvd Unit 169, Winter Haven, FL 33884

  TRANQUIL Living Awaits in This Beautifully Appointed Three-Bedroom Home in the Heart of Central Florida! Welcome to CYPRESS CREEK VILLAGE, one of the newest 55+ Active Adult communities...and PETS are welcome! Homes in CYPRESS CREEK VILLAGE, a 55+ PET-FRIENDLY community in Winter Haven, Florida, are on lot LEASED LAND. Owning the home, but not the land, you pay a monthly LOT RENT of $675

  Tammy Barnhart Renee's Resales

  336 Monterey Cypress Blvd Unit 169, Winter Haven, FL 33884
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  $450,000

  • Land
  • 4.36 Acres
  • $103,211 per Acre

  2230 Lake Daisy Rd, Winter Haven, FL 33884

  The property you are inquiring about is located in Winter Haven, FL in the Overlook Dr SE area of Polk County. This is 4.37 acres of improved land that has beautiful trees, pond with island, partially fenced, 2-story barn, covered RV parking space, septic system in place to accommodate an additional structure, well house to include pump, bladder tank and electrical panel, 400 Amp beneath ground

  Renee Butler BROKERS REALTY OF CENTRAL FLOR

  2230 Lake Daisy Rd, Winter Haven, FL 33884
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  /23

  $264,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  4792 Summerfield Cir, Winter Haven, FL 33881

  3 Bedroom, 2 Bath Split bedroom plan in Country Club Estates. Luxury Plank Vinyl throughout. Concrete block stucco construction. Primary bedroom has a tray ceiling & Walk in closet. Large great room, Kitchen with an island. Interior laundry with washer & dryer included. Attached 2 car garage. Close to schools, shopping and restaurants.

  Ronald Gentile ORLANDO REO PROF I INC

  4792 Summerfield Cir, Winter Haven, FL 33881
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  $234,900

  • 2 Beds
  • 2 Baths
  • 1,563 Sq Ft

  1077 Medinah Way, Winter Haven, FL 33884

  HARD TO FIND ...YET EASY TO OWN.!!! ENJOY COMING HOME TO THIS WONDERFUL COMMUNITY IN A TENNIS VILLA. IT IS A SPACIOUS END UNIT IN THE BEAUTIFUL CYPRESSWOOD GOLF AND TENNIS COMMUNITY WITH LOTS OF AMENITIES INCLUDING GATE SECURITY. CALL TO PREVIEW THIS WELL-MAINTAINED 2 BED 2 BATH CB VILLA, WITH FORMAL LIVING AND DINING AREA, SPACIOUS FLORIDA ROOM OVERLOOKING THE TENNIS COURTS AND POOL AREA, NICE

  Heidi Gravel WESTLAKE REAL ESTATE CO., INC.

  1077 Medinah Way, Winter Haven, FL 33884
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  /46

  $264,900

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  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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  $57,500

  • 1 Bed
  • 1 Bath
  • 648 Sq Ft

  4320 Dundee Rd Unit 61, Winter Haven, FL 33884

  Live Your Florida Dream You Deserve! Welcome to SOUTHERN DUCKS RV RESORT, an ACTIVE ADULT, PET-FRIENDLY community where you own your home and LEASE THE LAND in Winter Haven, Florida. MONTHLY LOT RENT is approximately $595, which includes WATER, SEWER, TRASH PICKUP, LAWN CARE, along with a wide range of amenities for you and your guests to enjoy. This 648 sq. ft, fully FURNISHED 1993

  Tammy Barnhart Renee's Resales

  4320 Dundee Rd Unit 61, Winter Haven, FL 33884
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  /39

  $272,000

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  3173 Whispering Trails Ave, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. WELCOME to this charming 3-bedroom, 3-bathroom home located in the beautiful gated community of Whispering Trails in Winter Haven, Florida. With 1,508 square feet of comfortable living space, this home features an open layout that seamlessly connects the kitchen, dining area, and living room, making it perfect for everyday living and

  Ashley Lopez KELLER WILLIAMS REALTY SMART 1

  3173 Whispering Trails Ave, Winter Haven, FL 33884
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  $152,500

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  268 Monterey Cypress Blvd, Winter Haven, FL 33884

  **Experience Florida Living at Its Finest!** Prepare to be captivated by this immaculate and elegant 2012 Nobility Maria, nestled in the highly sought-after Cypress Creek Village. This mostly furnished and freshly painted home boasts 1196 sq ft of beautifully designed living space, featuring 3 bedrooms, 2 bathrooms, and a delightful rear lanai leading to a bonus patio - all at an unbeatable

  Tanya Johnston American Mobile Home Sales of Tampa Bay, Inc.

  268 Monterey Cypress Blvd, Winter Haven, FL 33884
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  /36

  $200,000

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft

  1102 Eagle Pond Dr, Winter Haven, FL 33884

  Welcome to the Eagle Pond condominium in the Cypress Woods Golf and Country Club community. This coveted community is gated with 24-hour security guard. This bottom floor condo boasts 10-foot ceilings, open floor plan and two bedrooms with walk-in closets. The primary bedroom has an ensuite bathroom. The condo is newly painted with tile flooring in the Livingroom and kitchen. The bedrooms

  Robin McClendon CENTURY 21 MYERS REALTY LAKE WALES

  1102 Eagle Pond Dr, Winter Haven, FL 33884
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  /43

  $194,500

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft

  1507 Eagle Pond Dr Unit 1507, Winter Haven, FL 33884

  Welcome to the Eagle Pond condominium in the Cypress Woods Golf and Country Club community. This coveted community is gated with 24-hour security guard. The condo boasts 10-foot ceilings, open floor plan and two bedrooms with walk-in closets. The primary bedroom has an ensuite bathroom. The condo is newly painted with updated flooring. There is a spacious storage closet on the exterior to

  Robin McClendon CENTURY 21 MYERS REALTY LAKE WALES

  1507 Eagle Pond Dr Unit 1507, Winter Haven, FL 33884
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  /13

  $269,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  381 Troon Ct, Winter Haven, FL 33884

  Updated and beautifully maintained 2bd/2bath plus Bonus Room. Definitely one of the loveliest houses in Cypresswood. Golf and Country Club located on the 11th tee. The home offers exceptional views of the Fairway. Mature Landscaping and circular paved driveway. Welcome your buyer to this beautiful, maintained home. Large Living Room and adjacent dining room offers ample room for furnishings. The

  Barbara Downs CENTURY 21 WATSON & MYERS REALTY

  381 Troon Ct, Winter Haven, FL 33884
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  /42

  $167,500

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  244 Siberian Cypress Cir Unit 345, Winter Haven, FL 33881

  STUNNING DESIGN • High-End Finishes • BUILT IN 2019 • NEW ROOF in 2024 Welcome to CYPRESS CREEK VILLAGE, one of the newest 55+ Active Adult communities...and PETS are welcome! Homes in CYPRESS CREEK VILLAGE, a 55+ PET-FRIENDLY community in Winter Haven, Florida, are on lot LEASED LAND. Owning the home, but not the land, you pay a monthly LOT RENT of $684 which gives you and your guest

  Tammy Barnhart Renee's Resales

  244 Siberian Cypress Cir Unit 345, Winter Haven, FL 33881

Showing Results 1 - 40, Page 1 of 3

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.

Learn more about living in Cypresswood

Frequently Asked Questions

Is Cypresswood a good place to live?

Cypresswood is a good place to live. Cypresswood is considered very car-dependent and somewhat bikeable. Cypresswood is a suburban neighborhood. Cypresswood has 6 parks for recreational activities. It is sparse in population with 1.7 people per acre and a median age of 48. The average household income is $81,127 which is below the national average. College graduates make up 28.2% of residents. A majority of residents in Cypresswood are home owners, with 17.8% of residents renting and 82.2% of residents owning their home. A local real estate agent serving Cypresswood can help you decide if this neighborhood is the right one for you. Learn more on our Cypresswood neighborhood guide.

How much do you need to make to afford a house in Cypresswood?

The median home price in Cypresswood is $359,000. If you put a 20% down payment of $71,800 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $1,860 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $80K a year to afford the median home price in Cypresswood. The average household income in Cypresswood is $81K.

What are the best public schools in Cypresswood?

The best public schools that serve Cypresswood are:

• Union Academy has a B+ Niche grade, a student teacher ratio of 20:1 and an average review score of 3.7.
• Frank E. Brigham Academy has a B+ Niche grade and a student teacher ratio of 18:1.
• Bartow Elementary Academy has a B Niche grade, a student teacher ratio of 15:1 and an average review score of 4.2.

What are the best private schools in Cypresswood?

The best private schools that serve Cypresswood are:

• Winter Haven Christian School has a B Niche grade, a student teacher ratio of 17:1 and an average review score of 3.4.

What are the most popular zip codes in Cypresswood, Winter Haven, FL?

The most popular zip codes in Cypresswood, Winter Haven, FL include 33884, 33881, 33844, 33838 and 33859.

What are the most popular neighborhoods near Cypresswood, Winter Haven, FL?

The most popular neighborhoods near Cypresswood, Winter Haven, FL are Lake Fox, Poinsettia Park, Lake Ashton, Downtown Winter Haven and Lake Lucerne.

Are home prices dropping in Cypresswood?

Yes, home prices in Cypresswood are down 25% in the last 12 months.

Home Trends in Cypresswood, FL

On average, homes in Cypresswood, Winter Haven sell after 66 days on the market compared to the national average of 70 days. The median sale price for homes in Cypresswood, Winter Haven over the last 12 months is $314,499, down 23% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$314,499

Median Single Family Sale Price

$350,000

Median Townhouse Sale Price

$175,000

Median 1 Bedroom Sale Price

$195,000

Average Price Per Sq Ft

$307

Number of Homes for Sale

12

Last 12 months Home Sales

70

Months of Supply

2.10

Median List Price

$359,000

Median Change From 1st List Price

4%

Median Home Sale Price YoY Change

-23%