Cypresswood Homes for Sale

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  $272,500

  $30K PRICE DROP

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

  780 Overlook Grove Dr, Winter Haven, FL 33884

  HOME 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 quaint neighborhood, which quickly says

  

  Cyleste Goodson

  FLORIDA REAL ESTATE COMPANY

  780 Overlook Grove Dr, Winter Haven, FL 33884
• Explore Cypresswood

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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

  13 Bogey Dr, Winter Haven, FL 33881
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  /8

  $930,000

  • Land
  • 1.05 Acres
  • $885,714 per Acre

  4001 Dundee Rd, Winter Haven, FL 33884

  This 1.05-acre commercial property is ideally located on Dundee Road in Winter Haven, Florida, offering excellent visibility and a wide range of potential commercial uses. With an average daily traffic count of approximately 19,000 vehicles, the site provides strong exposure for businesses. Essential utilities, including water, sewer, electricity, telephone, and high-speed internet, are available

  Chip Fortenberry Crosby & Associates, Inc.

  4001 Dundee Rd, Winter Haven, FL 33884
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  /53

  $563,900

  $35K PRICE DROP

  • 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

  $340,000

  Open Sat 1PM - 3PM $10K PRICE DROP

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

  271 Inman Blvd, Winter Haven, FL 33881

  PRICE ADJUSTMENT!!! PRISTINE AND MOVE-IN READY! 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 wait. Step inside and be greeted by a bright and open first

  Isabelle Maye BHHS FLORIDA PROPERTIES GROUP

  271 Inman Blvd, Winter Haven, FL 33881
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  /24

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft

  1 Enclave Dr, Winter Haven, FL 33884

  Opportunity Knocks!Build sweat equity in this 3 bedroom 2 bathroom villa that is ready for some cosmetic updates.Make this home your own with fresh paint, new flooring and anything else you might desire.The unit is currently in habitable condition so you can live there and work at your own pace.Priced well below market value to allow room for cosmetic upgrades. The country club

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  1 Enclave Dr, Winter Haven, FL 33884
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  /51

  $354,800

  $45K PRICE DROP

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

  3228 Country Walk Club Cir, Winter Haven, FL 33881

  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 steel appliances and opens to

  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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  $69,900

  $2K PRICE DROP

  • 2 Beds
  • 2 Baths

  739 Red Cypress Ln, Winter Haven, FL 33881

  Discover the perfect blend of relaxation, recreation, and carefree Florida living in this beautifully updated 2-bedroom, 2-bath home located in the highly sought-after gated 55+ community of Cypress Creek Village! Ideally situated in Central Florida, you'll enjoy easy access to scenic lakes, botanical gardens, parks, museums, shopping, dining, and world-famous attractions. Whether you're seeking

  Linda Wilson Sunset Home Sales

  739 Red Cypress Ln, 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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  $482,000

  • 4 Beds
  • 3 Baths
  • 2,550 Sq Ft

  1814 Sandhill Ln, Winter Haven, FL 33884

  Here is your opportunity to own an immaculate home in the sought after community of Cypresswood Golf and Country Club. Consistently voted the Number 1 Golf Course in the area. This vibrant community has it all. Aside from the fantastic course right out your door, enjoy everything else it has to offer. A wonderful restaurant and Club House where they host live music 3 nights a week and top notch

  Stacy Tuttle REMAX EXPERTS

  1814 Sandhill Ln, 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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  /19

  $310,000

  $20K PRICE DROP

  • 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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  /34

  $280,000

  $20K PRICE DROP Pre-Foreclosure

  • 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

  Jeremy Ortiz LA ROSA REALTY PRESTIGE

  3136 Country Club Cir, Winter Haven, FL 33881
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  /13

  $314,900

  $20K PRICE DROP

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

  3132 Country Club Cir, Winter Haven, FL 33881

  PRICE TO SELL!! Seller very Motivated !! 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

  Irma Cruz FLORIDA REALTY MARKETPLACE

  3132 Country Club Cir, Winter Haven, FL 33881
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  /61

  $341,490

  $9K PRICE DROP

  • 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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  $137,500

  $36K 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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  /53

  $150,000

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft

  208 Monterey Cypress Blvd, Winter Haven, FL 33881

  Welcome home to effortless Florida living in this beautifully maintained, move-in-ready residence where every detail offers comfort, style, and convenience. From the immaculate landscaping and lush green lawn to the stamped concrete driveway that perfectly blends durability with curb appeal, this home makes a stunning first impression. This exceptional 2-bedroom, 2-bath oasis encompasses the

  Linda Wilson Sunset Home Sales

  208 Monterey Cypress Blvd, Winter Haven, FL 33881
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  /65

  $585,000

  • 4 Beds
  • 3 Baths
  • 2,916 Sq Ft

  1801 Sandhill Ln, Winter Haven, FL 33884

  If you're looking for a spacious, open-floor plan home with a lot of natural light, then look no further! This 4BR/3BA pool home located in the desirable Cypresswood Golf Community, offers many unique features, including high ceilings and a large Florida Room with large open windows offering a perfect view to the pool. The primary bedroom includes an ensuite bathroom with a garden tub and walk-in

  Emily Cassidy LAND SOURCE REALTY, LLC

  1801 Sandhill Ln, Winter Haven, FL 33884
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  /59

  $169,000

  $21K PRICE DROP

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

  645 Broadmoor Cir, Winter Haven, FL 33884

  FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit, spacious 2 bedroom 2 bath townhome in a gated community. This unit is conveniently located right across the street from the clubhouse, pool, tennis courts and golf course!! Great for just starting out or ready to retire. Great Florida Room for relaxing when the weather is nice. Close to shopping and LegoLand!!

  Rhonda Chastain CENTURY 21 MYERS REALTY

  645 Broadmoor Cir, Winter Haven, FL 33884
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  $325,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,140 Sq Ft

  731 Canberra Rd, Winter Haven, FL 33884

  Just REDUCED!! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large

  Melissa Witter KELLER WILLIAMS REALTY SMART 1

  731 Canberra Rd, Winter Haven, FL 33884
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  $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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  $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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  $379,900

  • 5 Beds
  • 3 Baths
  • 2,696 Sq Ft

  204 Inman Blvd, Winter Haven, FL 33881

  Welcome home to this beautifully maintained 5-bedroom, 3-bath residence offering nearly 2,700 square feet of flexible living space in one of Winter Haven's fastest-growing areas. Priced at just $379,900, this spacious home delivers exceptional value with room for everyone. Designed with today's lifestyles in mind, the thoughtfully crafted floor plan includes five true bedrooms, three full

  Veronica Bard LA ROSA REALTY PRESTIGE

  204 Inman Blvd, Winter Haven, FL 33881
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  /28

  $370,000

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,054 Sq Ft

  41 Greenfield Ct, Winter Haven, FL 33884

  Premier Location overlooking the pond and the golf course.This traditional 3 bedroom 2 bath estate home offers split bedrooms, formal living and dining areas, large family room, master suite with dual vanities and dual closets, oversized garage with a shower and a screen enclosed pool.From the pool deck, enjoy watching the varied species of birds that pass by or land for a stroll/swim in

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  41 Greenfield Ct, Winter Haven, FL 33884
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  /31

  $219,900

  $60K PRICE DROP

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

  14 Enclave Dr, Winter Haven, FL 33884

  This meticulously maintained and professionally updated 2 bedroom 2 bath villa is 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 and dryer, screened

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  14 Enclave Dr, Winter Haven, FL 33884
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  $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

  $395,000

  $80K PRICE DROP

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

  1908 Crossroads Blvd, Winter Haven, FL 33881

  MAJOR PRICE DROP! 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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  /28

  $235,000

  $20K PRICE INCREASE

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

  3147 Whispering Trails St, Winter Haven, FL 33884

  Virtually Staged. $5,000 PRICE REDUCTION!!! Don’t miss this incredible opportunity to own this beautifully updated home. Conveniently located just minutes from Walmart, LEGOLAND, shopping plazas, restaurants, and everyday conveniences, this home offers the perfect combination of comfort and location. Move-in ready with major 2026 updates! Enjoy peace of mind with a brand-NEW Roof (July 2026),

  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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  $304,900

  $8K PRICE DROP

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

  1871 Emily Dr, Winter Haven, FL 33884

  ****PRICE ADJUSTMENT**** Beautiful single-family home with 4 bedrooms and 2 bathrooms, totaling 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

  Cisco Romero REALTY OF AMERICA

  1871 Emily Dr, Winter Haven, FL 33884
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  /36

  $240,000

  $8K PRICE DROP

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

  4 Enclave Dr, Winter Haven, FL 33884

  THIS HOUSE QUALIFIES FOR $0 DOWN!!! Welcome to 4 Enclaves Dr., Winter Haven, FL—an exceptional opportunity to own a beautifully maintained home in one of Winter Haven's desirable gated golf course communities. Perfectly situated on a corner lot at the end of a quiet cul-de-sac, this immaculate residence offers privacy with a private entrance, curb appeal, and a peaceful setting. HOA covers all

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  4 Enclave Dr, Winter Haven, FL 33884
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  /33

  $219,900

  $14K PRICE DROP

  • 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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  /28

  $185,000

  $30K PRICE DROP

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

  2270 Firestone Place, Winter Haven, FL 33884

  Welcome to this spacious end-unit villa in Cypresswood Golf & Country Club, a gated golf community in Winter Haven known for its mature landscaping, active amenities, and welcoming atmosphere.Recent updates include new flooring throughout the living room, dining room, kitchen, and hallway, giving the main living areas a fresh, updated look. The spacious floor plan offers a comfortable

  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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  /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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  /2

  $375,000

  Open Sat 11AM - 1PM Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,097 Sq Ft

  4735 Summerfield Cir, Winter Haven, FL 33881

  Welcome home! Nestled on a spacious 0.22-acre lot, one of the largest in the community, this meticulously maintained property offers serene, unobstructed views of a private horse rescue farm.Step outside into your ultimate backyard oasis, where a south-facing private in-ground pool awaits to treat you to gorgeous Florida sunsets. The pool features a modern salt system, a 2-foot waterfall,

  Yunior Estevez Rodriguez AGILE GROUP REALTY

  4735 Summerfield Cir, Winter Haven, FL 33881

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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

Cypresswood Home Prices vs. Nearby Winter Haven, FL Neighborhoods

	Cypresswood	Cypress Gardens	Lake Fox	Lake Hamilton
Median Home Price	$320,000	$314,900	$269,900	$315,494
Median Sale Price	$290,000 +5% YoY	$292,990 -5% YoY	$265,000 -1% YoY	$301,265 -2% YoY
Median Single Family Price	$310,000	$316,900	$262,500	$305,990
Total Active Listings	59 listings	132 listings	12 listings	38 listings
Market Conditions	8 Months of Supply Buyer's Market	6 Months of Supply Balanced Market	6 Months of Supply Buyer's Market	2 Months of Supply Seller's Market

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 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 $320,000. If you put a 20% down payment of $64,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $1,650 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $71K 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 18:1.
• Jewett Middle Academy Magnet has a B- Niche grade, a student teacher ratio of 22:1 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 3.7.

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.