Cypresswood Homes for Sale

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  /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
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  Explore Cypresswood

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  /39

  $190,977

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

  307 Eagle Pond Dr, Winter Haven, FL 33884

  Price update!!! This beautiful 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, plus

  

  Mabel Vassallo

  CENTURY 21 MYERS REALTY

  (863) 431-4399

  307 Eagle Pond Dr, Winter Haven, FL 33884
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  /54

  $325,000 Open Sun 11AM - 1PM

  • 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
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  /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
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  /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
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  /13

  $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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  /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
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  /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
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  /42

  $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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  /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
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  /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
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  /34

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft

  749 Overlook Grove Dr, Winter Haven, FL 33884

  Welcome to 749 Overlook Grove Dr in Winter Haven! This charming home offers a desirable split floor plan with 3 bedrooms and 2 bathrooms, providing both comfort and functionality. The open layout makes it easy to entertain, while the spacious kitchen flows seamlessly into the living and dining areas. The primary suite includes its own private bathroom. Outside, you’ll find a fenced backyard—ideal

  Derek McGehee ALL COUNTY POLK PROPERTY MANAG

  749 Overlook Grove Dr, Winter Haven, FL 33884
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  /35

  $64,900

  • 1 Bed
  • 1 Bath

  4320 Dundee Rd Unit 36, Winter Haven, FL 33884

  This IMMACULATE Beach Bungalow is the Perfect Dream Home come true! Located in the Pristine ALL-AGE community of Southern Duck RV Resort in central Florida! With Exquisite curb appeal, first notice the pristine landscaping, clean-coated driveway under carport, and outdoor back patio with raised pavers for an evening under the warm Florida stars! This adorable cottage offers every modern

  Linda Wilson Sunset Home Sales

  4320 Dundee Rd Unit 36, Winter Haven, FL 33884
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  /44

  $159,900

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

  220 Monterey Cypress Blvd Unit 145, Winter Haven, FL 33884

  SPACIOUS, STYLISH & SERENE ... Your PEACE CREEK RETREAT 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, this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $781.00, which includes full access to RESORT-STYLE amenities for you and

  Tammy Barnhart Renee's Resales

  220 Monterey Cypress Blvd Unit 145, Winter Haven, FL 33884
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  /43

  $123,400

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881

  WELCOME to Your Stunning DREAM HOME... 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, this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $684, which includes full access to RESORT-STYLE amenities for you and your guests to

  Tammy Barnhart Renee's Resales

  1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881
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  /65

  $139,900

  • 3 Beds
  • 2 Baths
  • 1,566 Sq Ft

  1182 Heartwood Cypress Dr, Winter Haven, FL 33884

  MUSTANG RED GOLF CART INCLUDED. FRESHLY PAINTED INSIDE, 55 Plus Active Lifestyle Community. Seller is motivated. Only 6 years old which mean there is still plenty of life on the roof. LOW LOT FEE $521/month. This home has furniture that you can keep or can be removed if you have no need for it. You'll have all matching appliances, spacious shed, Golf CART INCLUDED, all season sunroom, laundry

  Daniel Butler Sun Realty of Florida

  1182 Heartwood Cypress Dr, Winter Haven, FL 33884
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  /58

  $209,000

  • 2 Beds
  • 2 Baths
  • 1,139 Sq Ft

  1012 Medinah Dr, Winter Haven, FL 33884

  Welcome to The Tennis Villas!?Nestled in the highly desired Cypresswood Golf & Country Club, this gated community with 24/7 security offers the perfect blend of comfort, convenience, and resort-style living.At the entry, a classic wrought iron gate opens to a private front patio, creating a welcoming first impression and a charming space to enjoy.This 2-bedroom, 2-bath villa features expansive

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  1012 Medinah Dr, Winter Haven, FL 33884
• 

  

  /19

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,303 Sq Ft

  2033 Whispering Trails Blvd, Winter Haven, FL 33884

  Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 15 minutes from the exciting attractions of Legoland, and less than an hour from the magical world of Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and

  Vivian Ortiz OAK AVENUE REAL ESTATE LLC

  2033 Whispering Trails Blvd, Winter Haven, FL 33884
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  /33

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,281 Sq Ft

  3025 Silverado Terrace, Winter Haven, FL 33884

  THIS HOME QUALIFIES FOR 0% DOWN !!Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop.

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  3025 Silverado Terrace, Winter Haven, FL 33884
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  /38

  $439,000

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

  2997 Plantation Rd, Winter Haven, FL 33884

  BEAUTIFULLY MAINTAINED, ONE OWNER POOL HOME IN DESIRABLE CYPRESSWOOD GOLF & COUNTRY CLUB PLANTATIONS!!! The Plantations is known for its charming setting, large lots, mature landscaping, friendly neighbors and peaceful streets to walk or bike ride! The entry into Cypresswood is manned with a 24hr security guard. You will want to call this property "home" the moment you arrive in the driveway

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  2997 Plantation Rd, Winter Haven, FL 33884
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  /25

  $219,900

  • 2 Beds
  • 2 Baths
  • 1,625 Sq Ft

  2243 Firestone Place Unit GP4, Winter Haven, FL 33884

  NEW REDUCED PRICE, HURRY TO SEE THIS MAINTENANCE-FREE & SPACIOUS GOLF VILLA - END UNIT WITH 2 BEDROOMS & 2 BATHS, LOCATED IN THE GATED & MANNED GOLF COMMUNITY OF CYPRESSWOOD GOLF & COUNTRY CLUB!!! 18-hole golf course, Pro shop, pool, tennis, fishing, wellness center, clubhouse, restaurant, pub and activities for an active lifestyle! The open floor plan features living room open to dining and

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  2243 Firestone Place Unit GP4, Winter Haven, FL 33884
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  /39

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  2817 Wingfoot Ct, Winter Haven, FL 33884

  Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open

  Dee Norris NEXTHOME NORRIS & COMPANY REALTY

  2817 Wingfoot Ct, Winter Haven, FL 33884
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  /32

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  676 Augusta Rd, Winter Haven, FL 33884

  Welcome to 676 Augusta, a charming and well-maintained home nestled on a beautifully landscaped 0.18-acre lot with majestic oak trees and a serene backyard setting. The tiled entry foyer leads into a spacious living and dining area with updated carpeting, which opens seamlessly to an enclosed Florida room—perfect for relaxing or entertaining. The kitchen features stainless steel appliances, a

  Dee Norris NEXTHOME NORRIS & COMPANY REALTY

  676 Augusta Rd, 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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  /26

  $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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  /54

  $469,000

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

  1908 Crossroads Blvd, Winter Haven, FL 33881

  SELLER MOTIVATED! 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,

  Jill Lingenfelter CENTURY 21 MYERS REALTY

  1908 Crossroads Blvd, Winter Haven, FL 33881
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  /59

  $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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  /30

  $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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  /44

  $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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  /34

  $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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  /73

  $500,000

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

  10 Webb Rd, Winter Haven, FL 33881

  AUCTION!! 10am, Sat. Sept. 13th 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,

  Martin E Higgenbotham HIGGENBOTHAM AUCTIONEERS INTERNATIONAL LTD INC

  10 Webb Rd, Winter Haven, FL 33881
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  /36

  $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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  /46

  $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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  /28

  $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
• 

  

  /51

  $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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /42

  $157,500

  • 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 2

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 $309,000. If you put a 20% down payment of $61,800 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $1,520 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $65K 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 19:1 and an average review score of 3.7.
• Frank E. Brigham Academy has a B+ Niche grade and a student teacher ratio of 17:1.
• 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 3.9.

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 33880.

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.

Home Trends in Cypresswood, FL

On average, homes in Cypresswood, Winter Haven sell after 71 days on the market compared to the national average of 52 days. The median sale price for homes in Cypresswood, Winter Haven over the last 12 months is $284,000, down 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$284,000

Median Single Family Sale Price

$300,999

Median 2 Bedroom Sale Price

$187,000

Average Price Per Sq Ft

$172

Number of Homes for Sale

48

Last 12 months Home Sales

87

Months of Supply

6.60

Median List Price

$309,000

Median Change From 1st List Price

4%

Median Home Sale Price YoY Change

-8%