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Cypresswood Homes for Sale

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  • /45

    $302,500

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

    780 Overlook Grove Dr, Winter Haven, FL 33884

    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 "community." The home

    Agent Photo

    Cyleste Goodson

    FLORIDA REAL ESTATE COMPANY

    (863) 265-1231

    780 Overlook Grove Dr, Winter Haven, FL 33884
  • /24

    $369,000

    $21K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,696 Sq Ft

    814 Turner Ln, Winter Haven, FL 33881

    Welcome to 814 Turner Lane, a beautifully upgraded Hayden model by D.R. Horton located in the heart of Winter Haven! ?? This spacious two-story home offers 5 bedrooms, 3 full bathrooms, and over 2,500 sq. ft. of living space, making it the perfect choice for families or anyone seeking extra room to spread out. Built with quality craftsmanship and thoughtful design, the Hayden model is known for

    Agent Photo

    Rafael Ortiz

    KELLER WILLIAMS LEGACY REALTY

    (863) 281-6734

    814 Turner Ln, Winter Haven, FL 33881
  • /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

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    Brock Jennings

    THE MARKET REALTY COMPANY

    (863) 774-3952

    13 Bogey Dr, Winter Haven, FL 33881
  • /37

    $340,000

    $9K 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
  • /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
  • /51

    $369,900

    $30K 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
  • /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
  • /2

    $330,000

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

    3155 Country Club Cir, Winter Haven, FL 33881

    MORE PHOTOS COMING SOON!! 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

    Luceyda Rodriguez Otero AGENT TRUST REALTY CORPORATION

    3155 Country Club Cir, Winter Haven, FL 33881
  • /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
  • /49

    $299,999

    • 2 Beds
    • 2 Baths
    • 1,293 Sq Ft

    469 Muirfield Ct, Winter Haven, FL 33884

    Charming and Affordable 2/2 Block Home in Cypresswood Golf CommunityDiscover comfort and convenience in this beautifully maintained 2 bedroom, 2 bathroom split floor plan block home located in the highly desirable Cypresswood Golf Community. This inviting residence offers a bright, open layout with spacious living areas and large walk-in closets in both bedrooms, providing plenty of storage

    Vikki Thielen THE MARKET REALTY COMPANY

    469 Muirfield Ct, Winter Haven, FL 33884
  • /47

    $382,000

    New Construction $3K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,215 Sq Ft

    934 Cattleman St, Winter Haven, FL 33884

    Stunning 5BR/2.5BA single family home on an oversized lot in the sought-after Inman Groves community. Move-in-ready home offers 2,215sq. ft. of thoughtfully designed living space with high ceilings, tile/carpet floors, and an open-concept layout. The kitchen features a spacious island and flows into the expansive family room. Upstairs, the owner’s suite includes a large walk-in closet and private

    Cristina de Oliveira Miami New Realty

    934 Cattleman St, Winter Haven, FL 33884
  • /54

    $419,900

    $55K 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
  • /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
  • /43

    $292,900

    $6K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,836 Sq Ft

    1864 Emily Dr, Winter Haven, FL 33884

    Come to see this move-in-ready, 4-bedroom 2-bath home located in the Beautiful Community of Emily Estates!! Featuring shiny new stainless steel appliances, fresh interior and exterior paint, and brand new plumbing fixtures, this home feels like it was just built! You will love everything about this house, but especially its light and bright floorplan, showering sunlight on the wide open living

    octavia Cheveresan RE/MAX ACTION FIRST OF FLORIDA

    1864 Emily Dr, Winter Haven, FL 33884
  • /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
  • /37

    $289,000

    • 2 Beds
    • 2 Baths
    • 1,621 Sq Ft

    428 Gleneagles Ct, Winter Haven, FL 33884

    Now is your chance! Come and be a part of this active, Golf Course community and live in this beautifully maintained, updated home. Enjoy the peaceful screened courtyard with your cup of coffee, or watch the gorgeous Florida sunsets. The inside of the home has been lovingly kept up and updated. You won't want for space in this well thought out layout. Plenty of room for entertaining, or a quiet

    Stacy Tuttle REMAX EXPERTS

    428 Gleneagles Ct, Winter Haven, FL 33884
  • /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. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows

    Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

    287 Inman Blvd, Winter Haven, FL 33881
  • /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
  • /39

    $309,900

    • 4 Beds
    • 2 Baths
    • 1,688 Sq Ft

    4856 Summerfield Cir, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Discover the perfect blend of modern updates and serene living in this stunning 4-bedroom, 2-bathroom home. Located in the highly sought-after Country Club Estates, this residence offers the privacy you've been searching for with a screened-in back patio overlooking a peaceful pond-meaning no rear neighbors, just tranquil water views. Step inside to

    Ronald Gentile

    4856 Summerfield Cir, Winter Haven, FL 33881
  • /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
  • /49

    $79,000

    $66K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    397 Siberian Cypress Cir, Winter Haven, FL 33881

    Welcome to this beautifully updated 3-bedroom, 2-bathroom home offering 1,344 square feet of comfortable living in the sought-after 55+ community of Cypress Creek Village in Winter Haven. Built in 2020, this residence is move-in ready and designed for relaxed Florida living. The home features well-manicured landscaping that enhances its curb appeal, along with low-maintenance vinyl siding, a

    Daniel Butler Sun Realty of Florida

    397 Siberian Cypress Cir, Winter Haven, FL 33881
  • /41

    $759,900

    • 4 Beds
    • 3.5 Baths
    • 2,944 Sq Ft

    1787 Lake Hill Dr, Winter Haven, FL 33884

    Be the first to own this stunning 2024-built semi-custom home located in the gated, lakefront community of Woodpointe in Winter Haven’s desirable 33884 zip code. Thoughtfully designed with both comfort and functionality in mind, this spacious residence features 4 bedrooms, 3.5 bathrooms, and an incredibly smart split-bedroom floorplan that offers privacy and flexibility for modern living. The

    Kayly Malinas JOHN WOOD REALTY, INC.

    1787 Lake Hill Dr, Winter Haven, FL 33884
  • /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
  • /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
  • /54

    $215,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,682 Sq Ft

    2813 Wingfoot Ct, Winter Haven, FL 33884

    Welcome to 2813 Wingfoot Court — now one of the best values in Cypresswood Golf & Country Club!Perfectly positioned along the 8th fairway inside this guard-gated golf community, this beautifully maintained 2-bedroom, 2-bath villa offers peaceful views and effortless Florida living—now at an exceptional new price.Being sold fully furnished and truly turnkey, this home is ready for

    Corinna Weaver CROSBY & ASSOCIATES, INC.

    2813 Wingfoot Ct, Winter Haven, FL 33884
  • /42

    $209,800

    • 3 Beds
    • 3 Baths
    • 1,992 Sq Ft

    429 Siberian Cypress Cir Unit 360, Winter Haven, FL 33881

    Lot #360 / 3 B / 3 BA / 1,992 Sq. Ft. / $209,800.00 Beautiful Like New 2023 Home! Builder's Model Showpiece - 2023 Erica Model in popular Cypress Creek Village! This large, one-owner home is located on a pond lot! It has a glass window enclosed screen room overlooking a patio and pond beyond. Enter into the large open concept home and look across the large Living Room, Dining Room, and Kitchen.

    Jennifer Meyers CRF Communities

    429 Siberian Cypress Cir Unit 360, Winter Haven, FL 33881
  • /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
  • /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
  • /24

    $275,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,015 Sq Ft

    584 Cody Caleb Dr, Winter Haven, FL 33884

    Discover this charming three-bedroom, two-bathroom residence in the desirable Savannah Estates, where comfort meets style. This inviting space features laminate flooring throughout, complemented by tile in the bathrooms. The open-concept design showcases a spacious kitchen, complete with ample cabinets, generous counter space, a breakfast bar, and stainless steel appliances, including a gas

    David Small KELLER WILLIAMS REALTY SMART 1

    584 Cody Caleb Dr, Winter Haven, FL 33884
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /83

    $442,000

    $23K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,433 Sq Ft

    2968 Plantation Rd, Winter Haven, FL 33884

    Enjoy serene golf-front living in this beautifully designed 3BR/2BA home, perfectly positioned to capture golf course frontage and tranquil water views—especially from the private screened patio off the primary suite. A versatile bonus room offers the ideal space for a home office or flex use, and the entire home is wired for surround sound. Thoughtfully equipped for comfort and efficiency, the

    Josh Taylor VILLAGE REALTY OF WINTER HAVEN

    2968 Plantation Rd, Winter Haven, FL 33884
  • /25

    $215,000

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

    3147 Whispering Trails St, Winter Haven, FL 33884

    Investor Special - LOW PRICED - SOLD AS IS NEEDS TLC– Endless Potential! Unlock the possibilities with this 3-bedroom, 2-bath home offering 1,303 sq ft in a gated Winter Haven community. Perfect for investors or buyers ready to add their personal touch, this property is a true TLC opportunity with great bones and plenty of upside. The home features a unique layout with a private side-entry front

    Gigi Sevilla NEWBERRY REALTY & DEV GRP INC.

    3147 Whispering Trails St, Winter Haven, FL 33884
  • /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
  • /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
  • /24

    $185,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,439 Sq Ft

    2270 Firestone Place, Winter Haven, FL 33884

    Welcome to this well-kept home in the highly sought-after Cypresswood Golf and Country Club, a gated community known for its beautiful grounds and exceptional amenities. Inside, you’ll find bright, open living spaces that flow seamlessly from the living room to the dining area and kitchen, creating a warm and functional layout for everyday comfort. The kitchen offers ample cabinetry and a

    Darin Dobson COMPASS FLORIDA LLC

    2270 Firestone Place, Winter Haven, FL 33884

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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.

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 1.7 people per acre and a median age of 48. The average household income is $81,127 which is below the national average. College graduates make up 28.2% of residents. A majority of residents in Cypresswood are home owners, with 17.8% of residents renting and 82.2% of residents owning their home. A local real estate agent serving Cypresswood can help you decide if this neighborhood is the right one for you. Learn more on our Cypresswood neighborhood guide.
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 $310,000. If you put a 20% down payment of $62,000 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $1,550 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:
What are the best private schools in Cypresswood?
The best private schools that serve Cypresswood are:
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 33859.
What are the most popular neighborhoods near Cypresswood, Winter Haven, FL?
The most popular neighborhoods near Cypresswood, Winter Haven, FL are Cypress Gardens, Lake Fox, North Winter Haven, Southeast Winterhaven and East Winter Haven.
Are home prices dropping in Cypresswood?
Yes, home prices in Cypresswood are down 4% in the last 12 months.

Home Trends in Cypresswood, FL

Housing Trends

Median Sale Price
$286,650
Median Single Family Sale Price
$303,750
Median 2 Bedroom Sale Price
$160,000
Average Price Per Sq Ft
$169
Number of Homes for Sale
50
Last 12 months Home Sales
100
Months of Supply
6.00
Median List Price
$310,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-1%
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