Cypresswood Homes for Sale

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  /15

  $260,000

  $39K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  3180 Country Club Cir, Winter Haven, FL 33881

  Short Sale. APPROVED SHORT SALE AT PRICE! CHAPTER 7 BANKRUPTCY - Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional

  

  Jon McCall PA

  DALTON WADE INC

  (863) 250-1507

  3180 Country Club Cir, Winter Haven, FL 33881
• Explore Cypresswood

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  /45

  $295,000

  $8K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,583 Sq Ft

  780 Overlook Grove Dr, Winter Haven, FL 33884

  BUYER'S CLOSING COSTS PAID UP TO $10K ! HOMW WARRANTY INCLUDED! Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Haven! Situated perfectly W of Hwy 27 and out of the hustle and bustle of the city, this 4/2/2 home is ready for you! Close to houses of worship, schools, shopping, golf, and SO much more! Upon arrival, you note the

  

  Cyleste Goodson

  FLORIDA REAL ESTATE COMPANY

  (863) 265-1231

  780 Overlook Grove Dr, Winter Haven, FL 33884
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  /100

  $1,799,900

  $150K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,708 Sq Ft

  13 Bogey Dr, Winter Haven, FL 33881

  Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist.The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends

  

  Brock Jennings

  THE MARKET REALTY COMPANY

  (863) 774-3952

  13 Bogey Dr, Winter Haven, FL 33881
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  /37

  $333,000

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,109 Sq Ft

  3322 Oak Hill Place, Winter Haven, FL 33884

  WELCOME HOME to this beautifully updated 3-bedroom, 2-bath residence located in the pristine gated community of Cypresswood! From the moment you enter the neighborhood, you’ll feel the charm of this private, resort-style community nestled in the heart of Polk County—just minutes from US Hwy 27, providing easy access to all that Central Florida has to offer.Step through the front door into a

  Michelle Keohane INFINITE REAL ESTATE POWERED BY ILIST

  3322 Oak Hill Place, Winter Haven, FL 33884
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  /32

  $598,900

  • 4 Beds
  • 3.5 Baths
  • 2,724 Sq Ft

  2935 Plantation Rd, Winter Haven, FL 33884

  Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800 square feet of spacious living when pool room footage is added. The offering includes a private pool, and a 9x9 pool house complete with a half bath, perfect for guests, poolside entertaining, or an additional flex space. Inside, the home boasts a

  Lovett Johnson LBJ REALTY AND ASSOCIATES LLC

  2935 Plantation Rd, Winter Haven, FL 33884
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  /41

  $350,000

  • 5 Beds
  • 2.5 Baths
  • 2,274 Sq Ft

  271 Inman Blvd, Winter Haven, FL 33881

  PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the

  Isabelle Maye BHHS FLORIDA PROPERTIES GROUP

  271 Inman Blvd, Winter Haven, FL 33881
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  /51

  $369,400

  $31K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,616 Sq Ft

  3228 Country Walk Club Cir, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to 3228 Country Walk Club Cir in Winter Haven! This spacious two-story home features 5 bedrooms and 3 bathrooms, offering plenty of room for family and entertaining. The home has been updated with fresh interior paint, brand-new carpet and vinyl flooring throughout, and modern lighting fixtures. The kitchen comes equipped with new stainless

  Jim Nagy PALM ISLAND REALTY

  3228 Country Walk Club Cir, Winter Haven, FL 33881
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  /6

  $400,000

  • Land
  • 34,412 Sq Ft
  • $506,329 per Acre

  0 Dundee Rd Unit MFRP4938646, Winter Haven, FL 33881

  Positioned along highly traveled Dundee Road, this prime commercial lot presents a rare, turnkey development opportunity in a growing Central Florida corridor. The property has already completed the state permitting process, significantly reducing timelines and uncertainty for a new owner or developer. With an approved driveway in place and site plans already prepared for a hotel, much of the

  Stetson Russell REAL FLORIDA REALTY LLC

  0 Dundee Rd Unit MFRP4938646, Winter Haven, FL 33881
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  /32

  $98,800

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  502 Leyland Cypress Way Unit 61, Winter Haven, FL 33881

  CYPRESS CREEK VILLAGE #61 / 2 BED / 2 BATH / 1,344 SF / $98,800 POND VIEW HOME with Double Driveway! This Large WELL MAINTAINED updated home is partially furnished and move-in-ready for you! This 2006 Nobility Home features an open floor plan and large two-level lanai overlooking a pond! Lanai includes tile floors, vinyl windows, roman shades, and a covered patio that is perfect for grilling out!

  Jennifer Meyers CRF Communities

  502 Leyland Cypress Way Unit 61, Winter Haven, FL 33881
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  /28

  $148,900

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

  1221 Cypress Vine Rd Unit 256, Winter Haven, FL 33884

  Lot #256 - 2 Bed /2 Bath + Den /1,568 Sq. Ft./$148,900.00 Spectacular Pond Views from this 2016 Ashley Model in beautiful Cypress Creek Village! This spacious home is located on a waterfront lot with breathtaking views! It offers a double carport with an additional golf cart path! This gorgeous home offers: *Vaulted Ceilings *Kitchen with coffee station and pantry *French doors into large den

  Jennifer Meyers CRF Communities

  1221 Cypress Vine Rd Unit 256, Winter Haven, FL 33884
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  /32

  $259,900

  $10K PRICE DROP

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

  29 Enclave Dr, Winter Haven, FL 33884

  New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit has just undergone a professional interior paint job. Enjoy Easterly pasture and sunrise views from the lanai. The country club amenities include access to the clubhouse with bar and grill, jr. olympic

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  29 Enclave Dr, Winter Haven, FL 33884
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  /25

  $314,990

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

  3308 Country Walk Club Cir, Winter Haven, FL 33881

  Welcome to this stunning 4-bedroom, 2-bath home located in a vibrant and growing neighborhood. Built in 2020, this modern residence offers the perfect blend of style, comfort, and functionality—ideal for today’s lifestyle.Step inside to discover a bright and spacious open-concept floor plan, perfect for both everyday living and entertaining. The gourmet kitchen is a true centerpiece,

  Humberto Cuevas LA ROSA REALTY LLC

  3308 Country Walk Club Cir, Winter Haven, FL 33881
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  /17

  $330,000

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

  3155 Country Club Cir, Winter Haven, FL 33881

  Welcome to this beautifully maintained home featuring a spacious open floor plan and numerous recent upgrades. The heart of the home boasts brand-new solid wood kitchen cabinets, providing both style and durability for the home chef. Step outside to your private backyard oasis, which comes fully equipped with a pristine above-ground pool, a secure fence encompassing the entire property for

  Luceyda Rodriguez Otero AGENT TRUST REALTY CORPORATION

  3155 Country Club Cir, Winter Haven, FL 33881
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  /56

  $370,000

  • 4 Beds
  • 2.5 Baths
  • 2,203 Sq Ft

  3142 Whispering Trails St, Winter Haven, FL 33884

  Minutes from Walmart, Winn Dixie, Restaurants, Shopping and Legoland, this charming home offers comfort and convenience in a prime location. Featuring a spacious layout perfect for everyday living and entertaining, its nestled in a well-maintained GATED COMMUNITY with Clubhouse, Pool and Scenic Walking Trails. Recent upgrades inlcude: Kitchen Cabinets, Tile Floors, New Stair Rails and Stair

  Gigi Sevilla NEWBERRY REALTY & DEV GRP INC.

  3142 Whispering Trails St, Winter Haven, FL 33884
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  /13

  $300,000

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

  3136 Country Club Cir, Winter Haven, FL 33881

  Welcome to a home that makes everyday living simple and enjoyable. Located in the established Country Club community, this property offers a practical layout, comfortable spaces, and a setting that supports an easy Florida lifestyle. Inside, you’ll find well-proportioned living areas with plenty of natural light, creating an open and functional feel. The kitchen connects seamlessly to the main

  Jeremy Ortiz LA ROSA REALTY PRESTIGE

  3136 Country Club Cir, Winter Haven, FL 33881
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  /61

  $349,990

  • 3 Beds
  • 2 Baths
  • 1,924 Sq Ft

  419 Greenfield Rd, Winter Haven, FL 33884

  Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, but by far the most impressive one is this gem and it shows. As you pull up to the extended driveway, low maintenance landscape ushers you into a well appointed home. Once in the front door, sparkling floor tiles guide you through this beautiful 3

  Ralph Eugene BOARDWALK REALTY ASSOCIATES, LLC

  419 Greenfield Rd, Winter Haven, FL 33884
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  /17

  $230,000

  Open Thu 9AM - 7PM $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft

  2953 Whispering Trails Dr, Winter Haven, FL 33884

  Come see 2953 Whispering Trails Dr, a residence showcasing recent fresh interior paint and fresh exterior paint for a clean, cohesive appearance. The kitchen is equipped with all stainless steel appliances, and the primary bathroom provides practical double sinks. Outside, a welcoming patio leads to a fully fenced in backyard. This move-in ready property blends comfort and recent updates

  Karen Albright OPENDOOR BROKERAGE LLC

  2953 Whispering Trails Dr, Winter Haven, FL 33884
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  /35

  $149,700

  $24K PRICE DROP

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

  649 Broadmoor Cir, Winter Haven, FL 33884

  UNDER MARKET VALUE!!! Brand NEW AC Fan motor, AC Amp Fuse and AC capacitor installed May 2026. Brand NEW fire/carbon monoxide detector alarms throughout the home. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Property is steps away from the golf clubhouse!!! Home features a stunning Florida

  Bill Sprys SUCCESS INVESTMENT REALTY

  649 Broadmoor Cir, Winter Haven, FL 33884
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  /39

  $270,000

  $10K PRICE DROP

  • 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 REAL

  2817 Wingfoot Ct, Winter Haven, FL 33884
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  /47

  $139,900

  $30K PRICE DROP

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

  252 Siberian Cypress Cir Unit 343, Winter Haven, FL 33881

  3 Bedroom / 2 Bathroom / 1586 sq. ft. / $139,900 Spring Savings! $10,000 price drop for March 2026 buyers! Cypress Creek Village lot 343 has a beautiful open floor plan on a nature filled private lot. This 2019 Champion with the much desired Live Oak floor plan features many upgrades. Enter through the light filled foyer. The large open kitchen has a chef's island, stainless appliances, and

  Jennifer Meyers CRF Communities

  252 Siberian Cypress Cir Unit 343, Winter Haven, FL 33881
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  /31

  $229,900

  $50K PRICE DROP

  • 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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  /49

  $195,000

  $4K PRICE DROP

  • 3 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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  /69

  $98,500

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

  948 Heartwood Cypress Dr, Winter Haven, FL 33881

  This well-maintained 2014 Nobility Lindsay, owned and occupied part-time by its original owner, is perfectly priced and move-in ready. Located in beautiful Cypress Creek Village, a premier 55+ community, this 3-bedroom, 2-bath home offers an affordable and comfortable Florida lifestyle - and it comes fully furnished. The spacious living room (16'6" x 18'2") features an open layout with

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

  948 Heartwood Cypress Dr, Winter Haven, FL 33881
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  /54

  $419,000

  $56K PRICE DROP

  • 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 handsome paver

  Jill Lingenfelter CENTURY 21 MYERS REALTY

  1908 Crossroads Blvd, Winter Haven, FL 33881
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  /23

  $16,500

  $3K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 620 Sq Ft

  1015 Dundee Rd Unit 34, Dundee, FL 33838

  Welcome to Greenfield Village, a quaint 55+ community in Dundee, Florida! This community has a LOW lot rent of just $450 per month, and has amenities including shuffleboard, swimming pool, clubhouse, and fishing! This home is super cute and compact, and is ready for immediate occupancy! Out front, there is a single car carport, and a lovely screen room. The main home has a kitchen with new

  Jennifer Maasdorp Integrity Mobile Homes

  1015 Dundee Rd Unit 34, Dundee, FL 33838
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  /25

  $240,000

  $25K PRICE INCREASE

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

  3147 Whispering Trails St, Winter Haven, FL 33884

  NEW PRICING!! NEW INSTALLED ROOF, AC AND APPLIANCES, KITCHEN FAUCET JUNE 2026. Discover the potential in this charming 3-bedroom, 2-bath home nestled within a gated Winter Haven community. Offering 1,303 square feet, this property features a unique side-entry front door connected by a private walkway, creating added character and curb appeal. Enjoy the comfort of an established neighborhood with

  Gigi Sevilla NEWBERRY REALTY & DEV GRP INC.

  3147 Whispering Trails St, Winter Haven, FL 33884
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  /20

  $87,900

  $2K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  1008 Heartwood Cypress Dr Unit 222, Winter Haven, FL 33881

  CYPRESS CREEK VILLAGE #222 / 2 BED / 2 BATH / 1,000 SF / $87,900 SPRING SAVINGS! NEW LOWER PRICE APPLIES TO MARCH 2026 BUYERS! COZY HOME with tranquil views! This 2016 Nobility Home features an open floor plan AND two large bedroom suites! The screen room overlooks a meadow framed by live oak trees. An additional covered area by the shed is a perfect spot for grilling! The open plan combines a

  Jennifer Meyers CRF Communities

  1008 Heartwood Cypress Dr Unit 222, Winter Haven, FL 33881
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  $312,500

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 2,012 Sq Ft

  1871 Emily Dr, Winter Haven, FL 33884

  Beautiful single-family home offering 4 bedrooms and 2 bathrooms with approximately 2,012 square feet of heated living space. This spacious residence features high ceilings and a functional layout designed for comfortable living and entertaining. The kitchen includes space for a breakfast table and flows seamlessly into a separate dining room, while an additional family room provides the perfect

  Cisco Romero REALTY OF AMERICA

  1871 Emily Dr, Winter Haven, FL 33884
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  /33

  $234,000

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

  10 Enclave Dr, Winter Haven, FL 33884

  WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers comfortable Florida living with a spacious open-concept living and dining room combination, abundant natural light, and a thoughtfully designed layout perfect for both relaxing and entertaining. The kitchen features beautiful

  Erin Floyd COLDWELL BANKER REALTY

  10 Enclave Dr, Winter Haven, FL 33884
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  /42

  $579,900

  $70K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,614 Sq Ft

  2964 Plantation Rd, Winter Haven, FL 33884

  Welcome to this refined sanctuary where timeless elegance meets Florida’s tranquil landscape. On a premium golf-adjacent lot within the guarded, gated community, 2964 Plantation Road blends gracious scale, luminous living and multi-generational flexibility in one seamless layout. Upon arrival, you are greeted by mature landscaping, a circular drive and side-entry access to a three-car garage,

  Audrey Christman PREMIER SOTHEBYS INT'L REALTY

  2964 Plantation Rd, Winter Haven, FL 33884
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  /24

  $185,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,439 Sq Ft

  2270 Firestone Place, Winter Haven, FL 33884

  Welcome to this spacious and well-maintained villa in Cypresswood Golf and Country Club, offering comfortable living in one of Winter Haven’s established gated golf communities. Inside, you’ll find an oversized living area with plenty of natural light, a functional kitchen with ample cabinet space, generously sized bedrooms, and an enclosed Florida room that adds valuable extra living space. The

  Darin Dobson COMPASS FLORIDA LLC

  2270 Firestone Place, Winter Haven, FL 33884
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  /30

  $184,900

  $15K PRICE DROP

  • 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 Florida

  Jennifer Meyers CRF Communities

  440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881
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  /50

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft

  69 Enclave Dr, Winter Haven, FL 33884

  Welcome to 69 Enclave Drive, a beautifully updated home nestled inside the sought-after Cypresswood Golf & Country Club, a gated golf community known for its lush landscaping, resort-style amenities, and peaceful, secure atmosphere right in the heart of Polk County.From the moment you arrive, the manicured curb appeal sets the tone: mature palms, trimmed hedges, and a well-maintained façade

  Manny Quiros RE/MAX HERITAGE PROFESSIONALS

  69 Enclave Dr, Winter Haven, FL 33884
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  /52

  $165,000

  $10K PRICE DROP

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

  1004 Medinah Dr, Winter Haven, FL 33884

  Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous

  Susan Human HUMAN TOUCH REAL ESTATE FIRM

  1004 Medinah Dr, Winter Haven, FL 33884
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  /90

  $744,900

  • 5 Beds
  • 4.5 Baths
  • 4,190 Sq Ft

  2954 Plantation Rd, Winter Haven, FL 33884

  PRICED BELOW RECENT APPRAISED VALUE OF $795,000 — APPRAISAL AVAILABLE FOR REVIEW! (Real Matterport Tour & Videos in Virtual Tour Links) Rare opportunity to own one of the most desirable waterfront golf course homes in Cypresswood Golf & Country Club. Positioned on a private corner lot overlooking the pond, 4th green, and 5th tee, this extensively updated 5-bedroom, 4.5-bath estate offers nearly

  Justino Zoppe KELLER WILLIAMS REALTY SMART 1

  2954 Plantation Rd, Winter Haven, FL 33884
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  /29

  $300,000

  Pre-Foreclosure

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

  3268 Country Walk Club Cir, Winter Haven, FL 33881

  Experience elevated living in this beautifully maintained 3 bedroom, 2 bathroom residence located in the highly desirable Country Walk community in Winter Haven. Designed with style and comfort in mind, this home showcases custom luxury finishes throughout the living room and bedrooms, creating an elegant and inviting atmosphere. The open concept layout offers the perfect blend of functionality

  Maria Santacruz KELLER WILLIAMS LEGACY REALTY

  3268 Country Walk Club Cir, Winter Haven, FL 33881
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  /43

  $292,900

  $6K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft

  1864 Emily Dr, Winter Haven, FL 33884

  Welcome to your dream home in the highly desirable community of Emily Estates! This stunning, move-in-ready 4-bedroom, 2-bathroom residence has been beautifully refreshed with brand-new interior and exterior paint, sparkling new stainless steel appliances, and upgraded plumbing fixtures throughout—giving it the crisp, clean feel of a brand-new build.You will love the light and bright

  octavia Cheveresan RE/MAX ACTION FIRST OF FLORIDA

  1864 Emily Dr, Winter Haven, FL 33884
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  /15

  $250,000

  $50K PRICE DROP

  • Land
  • 34,412 Sq Ft
  • $316,456 per Acre

  0 Dundee Rd Unit P4924283, Winter Haven, FL 33881

  Just Reduced! Stop by and check on this vacant lot in an area that is growing with new expanded roads. More than 3/4-acre zone C3 lot on Dundee Rd Hwy 542 with approx. 143 feet of road frontage. Ideally positioned in front of the 16th St intersection. The Department of Transportation finished up the Dundee Rd expansion improvements further to the East. This project has given this lot multiple

  Michael Brenner CENTURY 21 MYERS REALTY

  0 Dundee Rd Unit P4924283, Winter Haven, FL 33881
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  /27

  $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

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 with minimal transit options. Cypresswood has 6 parks for recreational activities. It is sparse in population with 2.0 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 18% of residents renting and 82% 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.

Is Cypresswood, FL a safe neighborhood?

Cypresswood, FL is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.

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

The median home price in Cypresswood is $309,900. If you put a 20% down payment of $62,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $1,540 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $66K a year to afford the median home price in Cypresswood. Learn how much home you can afford with our Home Affordability Calculator. 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 3.5.
• Frank E. Brigham Academy has a B+ Niche grade and a student teacher ratio of 17:1.
• Jewett Middle Academy Magnet has a B- Niche grade, a student teacher ratio of 23:1 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 3.5.

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 33837.

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

The most popular neighborhoods near Cypresswood, Winter Haven, FL are Cypress Gardens, East Winter Haven, Lake Fox, North Winter Haven and Southeast Winterhaven.

Are home prices dropping in Cypresswood?

Yes, home prices in Cypresswood are down 2% in the last 12 months.

Cypresswood Home Prices vs. Nearby Winter Haven, FL Neighborhoods

	Cypresswood	Sun Ridge	Southwest Winter Haven	Canoe Creek
Median Home Price	$309,900	$283,500	$294,250	$399,900
Median Sale Price	$280,650 -1% YoY	$285,000 +21% YoY	$260,000 -4% YoY	$377,000 -3% YoY
Median Single Family Price	$300,000	$279,999	$265,000	$400,000
Total Active Listings	56	15	40	126
Market Conditions	7 Months Buyer's Market	4 Months Balanced Market	4 Months Balanced Market	7 Months Buyer's Market