Studio to 5 Bedroom Homes for Sale in Cypresswood

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  /34

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  2893 Whispering Trails Dr, Winter Haven, FL 33884

  This cozy home offers a warm and inviting layout, perfect for anyone who prefers comfort and easy living. It features a functional floor plan with a modern kitchen, bright bedrooms, and low-maintenance spaces that make everyday life simple. Ideally located near US-27, US-17, SR-540, and with quick access to I-4, you’re just a short drive from Orlando, Tampa, Disney, Legoland, lakes, parks,

  Jenny Caso MY REALTY GROUP, LLC.

  2893 Whispering Trails Dr, Winter Haven, FL 33884
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  /36

  $369,000

  • 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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  /34

  $170,000

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

  2282 Firestone Place, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. 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

  Juan Yglesias KELLER WILLIAMS REALTY SMART 1

  2282 Firestone Place, Winter Haven, FL 33884
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  /35

  $59,900

  • 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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  /53

  $400,000

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  126 Lake Region Cir, Winter Haven, FL 33881

  Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a study, library

  Carol Sheil JUDY B CLEAVES PROPERTIES INC

  126 Lake Region Cir, Winter Haven, FL 33881
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  /62

  $785,000 New Construction

  • 3 Beds
  • 3 Baths
  • 2,541 Sq Ft

  4030 Palma Ceia Cir, Winter Haven, FL 33884

  Luxury New Construction in Cypresswoods!Discover the perfect blend of modern design and upscale living in this brand-new 3-bedroom, 3-bath home with a bonus room and over 2,450 sq. ft. of heated space. Crafted with attention to detail, this residence showcases soaring ceilings, designer tile floors, granite countertops, and a sleek open-concept layout. The heart of the home flows effortlessly

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  4030 Palma Ceia Cir, Winter Haven, FL 33884
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  /41

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft

  680 Augusta Rd, Winter Haven, FL 33884

  $5,000 CASH BACK TO BUYER AT CLOSING!!! Come see this beautiful home in Cypresswood gated community. Twenty four hour manned gate. Home has newly installed ADT system. This is a golf community with club house, restaurant, bar, pool and tennis/pickle ball courts. Upgrades include remodeled kitchen and appliances, remodeled bathroom, remote blinds and plantation shutters, ceramic tile roof, Generac

  Darlene Bice BHHS FLORIDA PROPERTIES GROUP

  680 Augusta Rd, Winter Haven, FL 33884
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  /44

  $153,900

  • 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 $804.00, 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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  /46

  $215,000

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

  683 Broadmoor Cir, Winter Haven, FL 33884

  NEW, NEW, NEW...this villa has recently been renovated. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. This beautiful home is located directly on golf course frontage and has newer metal roof. You will be living in a community with a manned guard gate and your villa is only a short walk to the clubhouse, restaurant, and pool. Don't miss out on this one,

  Darlene Bice BHHS FLORIDA PROPERTIES GROUP

  683 Broadmoor Cir, Winter Haven, FL 33884
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  /44

  $219,900

  • 2 Beds
  • 2 Baths
  • 1,278 Sq Ft

  1039 Medinah Dr, Winter Haven, FL 33884

  1 OWNER HOME!! Don't miss out on this 2 bed 2 bath tennis villa in the highly desired neighborhood of Cypresswood. The HOA takes care of the roof, lawn, paint, and exterior maintenance. Enjoy the security of living in a community with a 24 hour guard at the gate. There is plenty to do all within the community. There is a golf course, restaurant, community pool and tennis courts. The home has all

  Robert webb JOHN WEBB INC

  1039 Medinah Dr, Winter Haven, FL 33884
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  /51

  $75,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  707 Red Cypress Ln, Winter Haven, FL 33881

  2006 home in Cypress Creek Village, a premier 55+ community, will allow 40+! Super cute home with split bedroom plan with 2 large bedrooms, 2 baths, and a den! Spacious and open floor plan with an open-concept living area. Fully furnished with laminate flooring in the main areas, all window treatments remain. LIVING ROOM 17' 6 X 15' 9 Welcome to your new home! Spacious, Bright, and Open to the

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

  707 Red Cypress Ln, Winter Haven, FL 33881
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  /13

  $259,900

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  381 Troon Ct, Winter Haven, FL 33884

  PRICE SLASHED AND READY TO SELL!! 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

  Barbara Downs CENTURY 21 WATSON & MYERS REALTY

  381 Troon Ct, Winter Haven, FL 33884
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  /70

  $139,900

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

  164 Monterey Cypress Blvd Unit 121, Winter Haven, FL 33881

  THIS EXTRA LARGE, VERY WELL CARED FOR, UPDATED, 2010 NOBILITY ERICA IS JUST WAITING FOR YOUR ARRIVAL WITH 3 BEDROOMS, 3 BATHS, TOTALING 1848 INTERIOR SQUARE FT, PLUS A LARGE ENCLOSED FLORIDA ROOM WITH BEAUTIFUL VIEWS, MAKING THE SQUARE FOOTAGE OVER 1900! This Home has 3 Bedrooms and 3 Full Baths. The 2nd and 3rd Bedrooms are Tucked Away in the Rear left of The Home. Perfect for Long-Term Guests

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

  164 Monterey Cypress Blvd Unit 121, Winter Haven, FL 33881
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  /36

  $156,000

  • 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 have

  Robin McClendon CENTURY 21 MYERS REALTY LAKE WALES

  1102 Eagle Pond Dr, Winter Haven, FL 33884
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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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  /22

  $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 amenities. This

  Vivian Ortiz OAK AVENUE REAL ESTATE LLC

  2033 Whispering Trails Blvd, Winter Haven, FL 33884
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  /53

  $449,000

  • 4 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  108 Lake Region Blvd N, Winter Haven, FL 33881

  Builder’s model home with numerous upgrades and architectural details throughout. Located within the quaint, gated community of The Gates of Lake Region and built by Alan Ulch Construction, the home offers nearly 2,500 square feet of spacious living area. Construction includes high-efficiency Ytong concrete block, providing superior sound reduction, enhanced structural performance, and meaningful

  Michael Stone THE STONES REAL ESTATE FIRM

  108 Lake Region Blvd N, Winter Haven, FL 33881
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  /27

  $200,000

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

  1606 Eagle Pond Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. 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

  Juan Yglesias KELLER WILLIAMS REALTY SMART 1

  1606 Eagle Pond Dr, Winter Haven, FL 33884
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  /28

  $219,500

  • 2 Beds
  • 2 Baths
  • 1,398 Sq Ft

  1062 Medinah Dr, Winter Haven, FL 33884

  Location, Lifestyle & Leisure — All in One!Discover the perfect blend of comfort, convenience, and community in this beautifully maintained villa located in a sought-after gated Cypresswood Community with 24-hour security. Enjoy resort-style living with access to championship golf, tennis courts, a fitness center, community pool, on-site restaurant, and so much more — all just steps from your

  Doug DeWitt NEW HOME ADVANTAGE LLC

  1062 Medinah Dr, Winter Haven, FL 33884
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  /33

  $149,000

  • 2 Beds
  • 2 Baths
  • 1,647 Sq Ft

  1222 Cypress Vine Rd Unit 287, Winter Haven, FL 33884

  CYPRESS CREEK VILLAGE #287 - 2 BED + DEN / 2 BATH / 1,647 SF. / $149,900 CUSTOM BUILT HOME with Double Driveway! This OPEN FLOOR PLAN home is furnished and move-in-ready! This immaculately maintained home is VERY SPACIOUS! It features an open floor plan, integrated Florida Room, and screened front porch. This sought after Model has large rooms throughout. The spacious master bedroom suite has a

  Jennifer Meyers CRF Communities

  1222 Cypress Vine Rd Unit 287, 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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  /33

  $255,000

  • 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. It’s also

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  3025 Silverado Terrace, Winter Haven, FL 33884
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  /52

  $495,000

  • 4 Beds
  • 2 Baths
  • 2,756 Sq Ft

  2405 Melrose St, Winter Haven, FL 33881

  Welcome to this stunning 4-bedroom, 2-bath pool home that blends elegance, comfort, and functionality. From the moment you enter through the double doors, you’re greeted with an open floor plan and wood plank laminate flooring throughout, creating a warm and inviting atmosphere. The home features multiple living and dining spaces, including a formal living room, formal dining room (or

  Stacey Towns STACEY TOWNS REALTY LLC

  2405 Melrose St, Winter Haven, FL 33881
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  /38

  $239,500

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  466 Muirfield Ct, Winter Haven, FL 33884

  Sited in the desirable golfing community of Cypresswood Golf & Country Club is this charming Patio Home featuring a desirable split-bedroom floor plan with two generously sized bedrooms. As you enter the home, you'll be greeted by a charming side entry porch enhanced with a leaded glass door. The bright and cheerful living room boasts large windows and hardwood flooring, creating an inviting

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  466 Muirfield Ct, Winter Haven, FL 33884
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  /59

  $112,000

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

  203 Monterey Cypress Blvd, 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, Winter Haven, FL 33881
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  /30

  $334,900

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

  416 Sandestin Dr, Winter Haven, FL 33884

  UPSCALE HOME IN CYPRESSWOOD GOLF COMMUNITY. REDUCED! 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 with new 10 year warranty, natural gas instant hot water heater, new refrigerator 2022, new gas range, new

  Sharon Watson CENTURY 21 WATSON & MYERS REALTY

  416 Sandestin Dr, Winter Haven, FL 33884
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  /45

  $129,900

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

  284 Siberian Cypress Creek Cir, Winter Haven, FL 33881

  This 2022 home offers 1344 sq ft of living space, Immaculate and well-maintained. It has three bedrooms and two bathrooms with an open floor plan, perfect for entertaining family/friends or just relaxing. Additional living space can be found in the raised Florida room, along with the covered patio outdoors. Have a cookout and invite neighbors and friends! Key features of this home include a large

  Cynthia Cole Sunset Home Sales

  284 Siberian Cypress Creek Cir, Winter Haven, FL 33881
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  /49

  $310,000

  • 3 Beds
  • 2 Baths
  • 2,076 Sq Ft

  533 Saint Andrews Rd, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Florida living at its best! The spacious golf course home has three bedrooms two baths and is located in the gated, guarded, golf course community of Cypresswood. Situated on an oversized, landscaped lot on the 11th tee, this home boast soaring ceilings, open floor plan and a bright airy eat in kitchen. The luxurious master garden bath features dual

  Lynn Arthur FAITH AND FAMILY REALTY LLC

  533 Saint Andrews Rd, Winter Haven, FL 33884
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  /70

  $199,000

  • 3 Beds
  • 3 Baths
  • 1,716 Sq Ft

  352 Siberian Cypress Cir, Winter Haven, FL 33881

  STOP and TAKE A LOOK INSIDE! LOW LOT FEE $604/month, 55 Plus Active Lifestyle Community in Cypress Creek Village. 3 bedroom/3 bath home. The beautiful double wide home is spacious, has a Water Filtration System, is sold with all appliances, MOVE IN READY, Central Air, Storage Shed, Sunroom, Ceiling Fans, Walk In Closet, Ensuite Bathroom, Tray Ceiling, Removable Electric Fireplace, Gutters, Newer

  Daniel Butler Sun Realty of Florida

  352 Siberian Cypress Cir, Winter Haven, FL 33881
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  /25

  $256,000

  • 2 Beds
  • 2 Baths
  • 1,361 Sq Ft

  511 Pebble Springs Ct, Winter Haven, FL 33884

  Experience refined living in this beautifully updated 2-bedroom residence, perfectly situated within the coveted gated community of Cypresswood Golf & Country Club. The home has been thoughtfully maintained and enhanced with a long list of valuable updates, including a Roof (2019), A/C (2023), Tankless Water Heater (2024), Dishwasher (2024), Range (2024), and Microwave (2024). Additional upgrades

  Gina Morgando MORGANDO REALTY SERVICES, LLC

  511 Pebble Springs Ct, Winter Haven, FL 33884
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  /26

  $136,900

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1201 Cypress Vine Rd Unit 297, Winter Haven, FL 33881

  CYPRESS CREEK VILLAGE #297 - 2BED / 2 BATH / 1,200 SF. / $136,900 POND VIEW HOME with Double Driveway! Golf cart included! This MODERN, TURNKEY HOME is furnished and move-in-ready for you! This immaculately maintained home is only 5 years old! It features an open floor plan, air-conditioned four-season Florida Room and lower screened lanai - all of which have a tranquil pond view. This home has a

  Jennifer Meyers CRF Communities

  1201 Cypress Vine Rd Unit 297, 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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  /58

  $199,500

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  1012 Medinah Dr, Winter Haven, FL 33884

  Fresh new price — your opportunity to own in Cypresswood just got better! Seller will pay the first year’s HOA fees! 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,

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  1012 Medinah Dr, Winter Haven, FL 33884
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  /18

  $319,990

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  3029 Country Club Cir, Winter Haven, FL 33881

  Beautiful 4-bedroom, 2-bath home featuring ceramic tile flooring, granite countertops, and a spacious, fully fenced backyard perfect for gatherings and outdoor enjoyment. The property is equipped with solar panels with a low, fixed monthly payment, offering excellent energy efficiency and savings. Located in a desirable community with NO CDD and low HOA fees. This home is move-in ready and ideal

  Yamil Castro Hernandez LA ROSA REALTY ORLANDO LLC

  3029 Country Club Cir, Winter Haven, FL 33881

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