Cypresswood Homes for Sale

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  $211,000

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

  306 Eagle Pond Dr, Winter Haven, FL 33884

  Beautiful completely updated condo in the highly desirable gated community of Cypresswood Golf and Country Club. It features tile flooring throughout the whole condo, marble kitchen countertops with an extended breakfast island, matching marble on both bathroom vanities, upgraded lighting fixtures/ceiling fans, interior laundry with washer and dryer, pond view, and so much more. The master

  Amy Sullivan COLDWELL BANKER REALTY

  306 Eagle Pond Dr, Winter Haven, FL 33884
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  /47

  $190,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,422 Sq Ft

  1052 Medinah Dr, Winter Haven, FL 33884

  Welcome to the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left and right side of the entrance, which opens up additional outside entertaining space. Once inside the home you will notice it has recently been refreshed with new interior painting throughout, all new flooring, and new stove and

  Della Landfear XCELLENCE

  1052 Medinah Dr, Winter Haven, FL 33884
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  /37

  $179,900

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

  704 Eagle Pond Dr Unit 7D, Winter Haven, FL 33884

  Don't miss this rare opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas complete with a kitchen breakfast bar. All NEW luxury vinyl flooring, NEW

  Kayly Malinas JOHN WOOD REALTY, INC.

  704 Eagle Pond Dr Unit 7D, Winter Haven, FL 33884
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  /98

  $768,900

  $31K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,397 Sq Ft

  3050 Crump Rd, Winter Haven, FL 33881

  Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor living, and boating amenities. The main home features three bedrooms and

  Lisa Matheny ENGEL & VOELKERS LAKELAND

  3050 Crump Rd, Winter Haven, FL 33881
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  $370,000

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft

  652 Grove St, Winter Haven, FL 33884

  Welcome to 652 Grove St. TWO living spaces for ONE price. This exceptional property in the heart of Winter Haven offers a spacious main home plus a fully independent Mother-in-Law Suite all under the same roof. The primary residence features 3 bedrooms, 2 bathrooms, a dedicated office/flex space, an open-concept layout filled with natural light, and a 2-car garage designed for comfortable

  Lizandra Troisi Passos MY REALTY GROUP, LLC.

  652 Grove St, Winter Haven, FL 33884
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  /94

  $350,000

  New Construction $35K PRICE DROP

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

  934 Cattleman St, Winter Haven, FL 33884

  Beautiful 5-bedroom, 2.5-bath home built in 2023 and located in the desirable Inman Groves community. NO CDD, LOW HOA. This spacious home offers no rear neighbors, providing added privacy and peaceful views. The open-concept floor plan features a large great room, quartz countertops, stainless steel appliances, an oversized kitchen island, a walk-in pantry, and abundant cabinet space. Upstairs,

  934 Cattleman St, Winter Haven, FL 33884
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  /69

  $164,900

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

  312 Siberian Cypress Cir, Winter Haven, FL 33881

  Welcome to 312 Siberian Cypress Circle, a beautifully maintained 2019 home located in the highly desirable gated 55+ community of Cypress Creek Village in Winter Haven. One of this home's biggest advantages is its affordable lot rent of just **$616 per month**, making it an exceptional value in today's market while allowing you to enjoy all the benefits of this vibrant community. Offering

  Daniel Butler Sun Realty of Florida

  312 Siberian Cypress Cir, Winter Haven, FL 33881
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  /53

  $400,000

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

  126 Lake Region Cir, Winter Haven, FL 33881

  ALMOST PARADISE! 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

  Carol Sheil JUDY B CLEAVES PROPERTIES INC

  126 Lake Region Cir, Winter Haven, FL 33881
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  /38

  $180,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  213 Cleveland Ave, Winter Haven, FL 33881

  Welcome to this charming 2-bedroom, 1-bath home in the growing city of Winter Haven. Situated on a .16-acre oversized lot, this property offers both comfort and opportunity. The home features a functional layout and a new AC installed in 2024, providing added efficiency and peace of mind. The spacious backyard includes a detached shed with great potential, perfect for a workshop, studio, storage,

  Pedro Perez, Jr DALTON WADE INC

  213 Cleveland Ave, Winter Haven, FL 33881
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  /31

  $325,000

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

  319 Niblick Cir, Winter Haven, FL 33881

  Lovely 2 bedroom and 2 bathroom home located in a private gated community of just over 100 homes in Winter Haven, FL. Situated between Tampa and Orlando with easy access to both international airports. Short distance to theme parks, Legoland, Bok Tower Gardens. New Publix grocery store opening soon is a short drive away. New HVAC installed in 2022. Freshly painted interior and exterior. House

  Steven Koleno BEYCOME OF FLORIDA LLC

  319 Niblick Cir, Winter Haven, FL 33881
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  /44

  $469,900

  Open Fri 1PM - 3PM

  • 5 Beds
  • 3 Baths
  • 2,588 Sq Ft

  3749 Fieldstone Cir, Winter Haven, FL 33881

  Your perfect home with a Poolside Paradise Awaits! This stunning five-bedroom, three-bathroom home boasts an inviting screened-in pool area, perfect for relaxation and entertainment. Nestled in a prime location with convenient access to Highway 27, this residence offers an exceptional living experience that blends elegance and practicality. As you step through the impressive double door entry,

  David Small KELLER WILLIAMS REALTY SMART 1

  3749 Fieldstone Cir, Winter Haven, FL 33881
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  /46

  $198,000

  $40K PRICE DROP

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

  683 Broadmoor Cir, Winter Haven, FL 33884

  This villa has recently had upgrades added and the seller is offering $7,000 AT CLOSING TOWARD CLOSING COSTS OR ADDITIONAL UPGRADES. 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

  Darlene Bice BHHS FLORIDA PROPERTIES GROUP

  683 Broadmoor Cir, Winter Haven, FL 33884
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  /32

  $340,000

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft

  507 Short Ln, Winter Haven, FL 33881

  ""SELLER MOTIVATED – PRICE IMPROVEMENT! BRING YOUR OFFER!""Beautiful and well-maintained home featuring 4 spacious bedrooms and 2 bathrooms, offering plenty of space for comfortable family living and entertaining guests. Sliding glass doors lead to a covered patio and a private grassy backyard, perfect for relaxing and enjoying Florida’s outdoor lifestyle. The kitchen comes fully equipped

  Anderson Siqueira, Sr WRA BUSINESS & REAL ESTATE

  507 Short Ln, Winter Haven, FL 33881
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  /18

  $340,000

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

  937 Cattleman St, Winter Haven, FL 33881

  Welcome to this beautifully maintained, nearly new 4-BEDROOM, 2-BATHROOM home in the desirable INMAN GROVES community! Built in 2023 by D.R. Horton, this popular CALI FLOOR PLAN offers 1,828 square feet of thoughtfully designed living space with an open-concept layout perfect for both everyday living and entertaining. The spacious kitchen features SOLID SURFACE COUNTERTOPS, STAINLESS STEEL

  Isabelle Maye BHHS FLORIDA PROPERTIES GROUP

  937 Cattleman St, Winter Haven, FL 33881
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  /43

  $349,950

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,523 Sq Ft

  241 Greenfield Rd, Winter Haven, FL 33884

  Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot on the 13th green. This charming 2-bedroom, 2-bathroom residence features a bright and open layout with a large living area plus an additional family room accented by a cozy brick fireplace and floor-to-ceiling wood built-ins. The brand-new kitchen has

  Angie Reynolds PORCHLIGHT HOMES LLC

  241 Greenfield Rd, Winter Haven, FL 33884
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  $139,900

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

  1182 Heartwood Cypress Dr, Winter Haven, FL 33884

  LOW LOT RENT $521/MO. MUSTANG RED GOLF CART CAN BE INCLUDED. FRESHLY PAINTED INSIDE, 55 Plus Active Lifestyle Community. SOME PHOTOS HAVE BEEN VIRTUALLY STAGED. Seller is motivated and willing to replace the flooring with an acceptable offer. Buyers may choose the laminate flooring that best suits their style and preferences. The listing photos include virtually staged examples showcasing both

  Daniel Butler Sun Realty of Florida

  1182 Heartwood Cypress Dr, Winter Haven, FL 33884
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  /52

  $425,000

  $24K PRICE DROP

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

  108 Lake Region Blvd N, Winter Haven, FL 33881

  Located within the highly desirable gated community of The Gates of Lake Region, this beautifully maintained neighborhood is known for its picturesque brick-walled entrance, lush mature landscaping, tranquil ponds with fountains, and pride of ownership throughout. Unlike larger developments, The Gates of Lake Region offers a warm, neighborly atmosphere where residents enjoy quiet streets,

  Michael Stone THE STONES REAL ESTATE FIRM

  108 Lake Region Blvd N, Winter Haven, FL 33881
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  /2

  $150,000

  • Land
  • 13,939 Sq Ft
  • $468,750 per Acre

  1776 Lake Hill Dr, Winter Haven, FL 33884

  Large residential lot that will accommodate a variety of floor plans. Builder and building plans must be approved by Owner.

  John Wood, JR JOHN WOOD REALTY, INC.

  1776 Lake Hill Dr, Winter Haven, FL 33884
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  /24

  $337,000

  $17K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,586 Sq Ft

  688 Augusta Rd, Winter Haven, FL 33884

  Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW

  Kayly Malinas JOHN WOOD REALTY, INC.

  688 Augusta Rd, Winter Haven, FL 33884
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  /16

  $340,000

  New Construction $8K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,853 Sq Ft

  643 Grove St, Winter Haven, FL 33881

  Location, Location , Location Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quartz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and an-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!

  Martha Leighton MIHOUSE REALTY LLC

  643 Grove St, Winter Haven, FL 33881
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  $154,900

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  184 Monterey Cypress Blvd, Winter Haven, FL 33881

  LOOK NO FURTHER! NEW ROOF, NEW AC. Welcome to Cypress Creek Village! This spacious double-wide home offers comfortable Florida living with a beautiful canal water view in a desirable gated community in Winter Haven. This 2-bedroom, 2-bath home features 1,456 sq. ft. of living space and offers a thoughtful layout with plenty of room to relax, entertain, and enjoy the Florida lifestyle. The home

  Daniel Butler Sun Realty of Florida

  184 Monterey Cypress Blvd, Winter Haven, FL 33881
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  /49

  $1,100,000

  • Land
  • 52.52 Acres
  • $20,944 per Acre

  3705 High St, Winter Haven, FL 33881

  Prime investment opportunity in the expanding Winter Haven area! This 52.52± acre parcel of vacant land offers exceptional potential for future development. The property is currently being used for agricultural purposes, with beautiful grazing pasture and cattle on site, providing wide open space and scenic surroundings.Winter Haven and the surrounding Central Florida region continue to

  Stacey Towns STACEY TOWNS REALTY LLC

  3705 High St, Winter Haven, FL 33881
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  /2

  $115,000

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

  333 Midnight Cypress Dr Unit 9, Winter Haven, FL 33881

  Lot #9 - 3 Bed /2 Bath /1,568 Sq. Ft./ $115,000.00 Spectacular Pond Views from this 2007 Kingswood Model in beautiful Cypress Creek Village! This spacious home is located on a waterfront lot with breathtaking views! It offers a paver parking alongside the carport with an additional pond view paver patio! This gorgeous home offers: *Vaulted Ceilings *Kitchen with soft close cabinets and solid

  Jennifer Meyers CRF Communities

  333 Midnight Cypress Dr Unit 9, Winter Haven, FL 33881
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  /36

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  287 Inman Blvd, Winter Haven, FL 33881

  Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. In addition to the home’s like-new condition and thoughtful upgrades, qualified buyers may also have the rare opportunity to assume the

  Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

  287 Inman Blvd, Winter Haven, FL 33881
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  /25

  $177,500

  $8K PRICE DROP

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

  1026 Medinah Dr, Winter Haven, FL 33884

  Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa.Recent updates include new luxury vinyl flooring, new dishwasher and new microwave.MOVE IN CONDITION.The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  1026 Medinah Dr, Winter Haven, FL 33884
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  /21

  $300,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  715 Grove St, Winter Haven, FL 33884

  ***This home can be yours for 4.75% Interest rate on a assumable loan*** Located in the desirable Inman Grove solar community in Winter Haven, this 3 bedroom, 2 bathroom home with a fully fenced backyard offers the perfect combination of energy efficiency, modern design, and convenient Central Florida living. Built in 2023, NO CDD, LOW HOA of less than $45.00 a month, LOW ELECTRIC BILL

  Jannese Garcia NORKIS & CO REALTY

  715 Grove St, Winter Haven, FL 33884
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  /61

  $245,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,444 Sq Ft

  47 Enclave Dr, Winter Haven, FL 33884

  PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the

  David Shippey XCELLENCE

  47 Enclave Dr, Winter Haven, FL 33884
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  /33

  $235,000

  • 2 Beds
  • 2 Baths
  • 1,395 Sq Ft

  664 Clubhouse Rd, Winter Haven, FL 33884

  Situated in the desirable golfing community of Cypresswood Golf & Country Club, this lovely 2-bedroom, 2-bath townhome offers comfort, style, and beautiful golf course views. Upon arrival, you'll be welcomed by a charming courtyard adorned with pavers, creating a warm and inviting entrance. A glass storm door and smart lock entry provide both convenience and security. Inside, luxury vinyl plank

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  664 Clubhouse Rd, Winter Haven, FL 33884
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  /22

  $170,000

  $10K PRICE DROP

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

  665 Broadmoor Cir, Winter Haven, FL 33884

  Discover how easy life can feel in this beautifully maintained 2-bedroom, 2-bath villa offering over 1,100 square feet of comfortable, thoughtfully designed living space. With a mostly furnished interior and quick occupancy available, you can step right in and start enjoying it from day one. Located inside the gated CypressWood golf community, this home delivers true resort-style living. Spend

  Darin Dobson COMPASS FLORIDA LLC

  665 Broadmoor Cir, Winter Haven, FL 33884
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  $300,000

  • 3 Beds
  • 2 Baths
  • 1,919 Sq Ft

  3742 Fieldstone Cir, Winter Haven, FL 33881

  Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,919 square feet of comfortable living space in the well-kept community of Country Club Estates of Winter Haven. Lovingly cared for as a second home, this residence shows pride of ownership throughout and is truly move-in ready. The spacious floor plan provides plenty of room for everyday living and entertaining, while the

  Brandy Duncan COLDWELL BANKER REALTY

  3742 Fieldstone Cir, Winter Haven, FL 33881
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  /70

  $199,000

  $51K PRICE DROP

  • 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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  /24

  $129,900

  $7K PRICE DROP

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

  1201 Cypress Vine Rd, Winter Haven, FL 33881

  CYPRESS CREEK VILLAGE #297 - 2BED / 2 BATH / 1,200 SF. / $129,900 POND VIEW HOME with Double Driveway! This MODERN HOME is the essence of quality. The 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 split floor plan with two large bedroom

  Jennifer Meyers CRF Communities

  1201 Cypress Vine Rd, Winter Haven, FL 33881
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  /62

  $187,900

  $21K PRICE DROP

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

  1012 Medinah Dr, Winter Haven, FL 33884

  NOW OFFERING A HOME WARRANTY! Your opportunity to own in the highly sought-after Cypresswood Golf & Country Club just became even more appealing. Welcome to The Tennis Villas, where gated security, resort-style amenities, and maintenance-friendly living come together in one of Central Florida’s premier golf communities. A charming wrought iron gate welcomes you into a private front courtyard

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  1012 Medinah Dr, Winter Haven, FL 33884
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  /49

  $179,000

  • 3 Beds
  • 3 Baths
  • 1,749 Sq Ft

  332 Siberian Cypress Cir, Winter Haven, FL 33881

  $632 LOT RENT! Welcome home to Cypress Creek Village in Winter Haven, Florida! This beautifully designed 2022 ScotBilt home offers the perfect blend of comfort, space, and resort-style living in one of Winter Haven's sought-after 55+ gated communities. Featuring 3 bedrooms, 3 bathrooms, and 1749 square feet of living space, this home was built for easy living and entertaining. Step inside to an

  Daniel Butler Sun Realty of Florida

  332 Siberian Cypress Cir, Winter Haven, FL 33881

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