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Cypresswood Homes for Sale

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  • /39

    $182,000

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

    307 Eagle Pond Dr, Winter Haven, FL 33884

    PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings.Inside, you'll love the bright, open layout with 10' ceilings, rich wood

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    Mabel Vassallo

    CENTURY 21 MYERS REALTY

    (863) 431-4399

    307 Eagle Pond Dr, Winter Haven, FL 33884
  • /35

    $280,000

    • 3 Beds
    • 2 Baths
    • 1,891 Sq Ft

    606 Turnberry Ct, Winter Haven, FL 33884

    Looking for a gated community, 3 bedroom home with a bonus room? No need to look any further! Welcome to the highly sought-after Cypresswood Golf Community, where comfort, security, and convenience come together in this spacious 3-bedroom, 2-bath home with an added air conditioned Florida Room that offers a flexible bonus space perfect for anything your lifestyle calls for. Enjoy beautiful golf

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    Daniel Rodriguez

    NEW HEIGHTS REALTY GROUP

    (863) 334-3846

    606 Turnberry Ct, Winter Haven, FL 33884
  • /15

    $250,000

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

    3180 Country Club Cir, Winter Haven, FL 33881

    BANKRUPTCY SHORT SALE! 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 Kitchen Overlooking The Main Living Space.

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    Jon McCall PA

    Dalton Wade Inc

    (863) 250-1507

    3180 Country Club Cir, Winter Haven, FL 33881
  • /47

    $245,500

    • 3 Beds
    • 2 Baths
    • 1,602 Sq Ft

    2805 Wingfoot Ct, Winter Haven, FL 33884

    Fully Renovated Golf Course Home – Perfect for Full or Part-Time Living Located directly on the golf course in Cypress Woods Golf & Country Club, this beautifully renovated home is a 2 bedroom, 2-bath home with an optional 3rd bedroom or sunroom. Home showcases quality craftsmanship and modern upgrades throughout — ideal for both full-time residents and seasonal owners.The open floor plan

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    Lynn Arthur

    FAITH AND FAMILY REALTY LLC

    (863) 845-1955

    2805 Wingfoot Ct, Winter Haven, FL 33884
  • /100

    $1,895,000

    • 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
  • /24

    $369,000

    • 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

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    Rafael Ortiz

    KELLER WILLIAMS LEGACY REALTY

    (863) 375-8538

    814 Turner Ln, Winter Haven, FL 33881
  • /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

    $383,900

    • 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
  • /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
  • /13

    $295,990 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft

    3108 Country Club Cir, Winter Haven, FL 33881

    Beautiful home featuring 3 spacious bedrooms and 2 full bathrooms, with a large backyard and no rear neighbors for added privacy. Located in the growing city of Winter Haven, this property is surrounded by new commercial development and is just minutes from schools and hospitals. Conveniently located only 5 minutes from US Hwy 27. Enjoy a low HOA of just $30/month and a community with no CDD

    Zonybeth Gonzalez Rodriguez LPT REALTY, LLC

    3108 Country Club Cir, Winter Haven, FL 33881
  • /47

    $382,000 New Construction

    • 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
  • /51

    $335,000

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

    731 Canberra Rd, Winter Haven, FL 33884

    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 ensuite bath

    Melissa Witter KELLER WILLIAMS REALTY SMART 1

    731 Canberra Rd, Winter Haven, FL 33884
  • /43

    $297,000

    • 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
  • /41

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,892 Sq Ft

    720 Overlook Grove Dr, Winter Haven, FL 33884

    Welcome to 720 Overlook Grove Dr in beautiful Winter Haven!This move-in ready home has just received a fresh interior and exterior paint update, giving it a clean, modern feel throughout. Enjoy peace of mind with a new roof (2023) and numerous upgrades that make this property truly stand out.The updated kitchen features modern finishes, refreshed cabinetry, and upgraded

    Jenny Nguyen LOKATION

    720 Overlook Grove Dr, Winter Haven, FL 33884
  • /39

    $285,000

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

    610 Grove St, Winter Haven, FL 33881

    This 3 YEAR YOUNG, 4 bedroom, 2 bath single-family home built by DR Horton offers 1,867 square feet of thoughtfully designed living space and a 2-car ATTACHED GARAGE with OPENER and NO SOLAR PANELS!! The open floorplan features a seamless kitchen, dining area, and family room combination, ideal for both everyday living and entertaining. The kitchen includes a CENTER ISLAND, GRANITE countertops,

    Pat Pearson VIEWPOINT VALUE REALTY

    610 Grove St, 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
  • /23

    $310,000

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

    715 Grove St, Winter Haven, FL 33884

    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 MONTHLY..averaging $30-$83 a month ***=SAVINGS***, this newer construction home

    Jannese Garcia LPT REALTY, LLC

    715 Grove St, Winter Haven, FL 33884
  • /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

    • 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
  • /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

    $230,000

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

    2813 Wingfoot Ct, Winter Haven, FL 33884

    Welcome to 2813 Wingfoot Court in the sought-after Cypresswood Golf Villas! Perfectly positioned along the 8th fairway of Cypresswood Golf & Country Club, this guard-gated community offers peaceful golf course views and a relaxed Florida lifestyle.This beautifully maintained 2-bedroom, 2-bathroom villa is being sold fully furnished and truly turn-key — just bring your suitcase. The professionally

    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
  • /37

    $179,000

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

    332 Siberian Cypress Cir, Winter Haven, FL 33881

    **CHARMING 3B/3B HOME IN A 55+ PET FRIENDLY GATED COMMUNITY! ** Welcome to your new sanctuary in a vibrant 55+ gated community in beautiful Winter Haven Florida! This stunning like new 2022 Scot Built Manufactured Home offers a generous 1,749 sq. ft. of thoughtfully designed living space, perfect for enjoying your golden years. This home features a spacious master suite where you can indulge in

    Mary Sergent USA Mobile & Manufactured Home Sales, LLC.

    332 Siberian Cypress Cir, Winter Haven, FL 33881
  • /32

    $269,900

    • 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

    • 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

    • 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

    • 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
  • /42

    $250,000

    • 2 Beds
    • 2 Baths
    • 1,571 Sq Ft

    730 Canberra Rd, Winter Haven, FL 33884

    Buyer defaulted, yall come back to this under appraisal, ready to move into home. The property you are inquiring about is located in Winter Haven, FL, in the Cyresswood area of Polk County. Walk in with $25,000 equity as this home is vacant and ready to close in 10! This is located in Cypresswood, the gated, golfing community that has a clubhouse and many activities. The home features 2 bedrooms,

    Renee Butler BROKERS REALTY OF CENTRAL FLOR

    730 Canberra Rd, Winter Haven, FL 33884
  • /31

    $239,900

    • 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

    $199,000

    • 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

    • 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
  • /30

    $249,900

    • 2 Beds
    • 2 Baths
    • 1,328 Sq Ft

    634 Wexford Ct, Winter Haven, FL 33884

    MOVE IN CONDITION! Nestled on a beautifully landscaped and tree shaded lot this well maintained 2 bedroom 2 bathroom patio home features split bedrooms with ample closets, an expansive great room with space for living and dining areas, breakfast nook in the kitchen and an attached 2 car garage. Additional amenities include an oversized rear screened porch overlooking a picturesque greenspace with

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    634 Wexford Ct, Winter Haven, FL 33884
  • /49

    $499,900

    • 4 Beds
    • 3 Baths
    • 2,467 Sq Ft

    1936 Crossroads Blvd, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Welcome to 1936 Crossroads Blvd in the highly sought-after gated community of Crossroads at Lake Region. This exquisite entertainer’s paradise comes partially furnished, features a private screened pool and spa, upgraded finishes throughout, and a fully fenced backyard designed for relaxation and entertaining. This meticulously upgraded Rockingham

    Craig Murrell REMAX EXPERTS

    1936 Crossroads Blvd, Winter Haven, FL 33881
  • /20

    $87,900

    • 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
  • /52

    $135,000

    • 3 Beds
    • 3 Baths

    136 Monterey Cypress Blvd, Winter Haven, FL 33881

    Enjoy peaceful living in this beautifully maintained Nobility Erica home, perfectly situated in desirable Cypress Creek Village with serene water views and ultimate privacy!- Step inside to a bright and spacious 17' x 15'5" living room, featuring gorgeous laminate wood flooring and a ceiling fan, flowing seamlessly into the open dining area-ideal for entertaining.- The 9' x 11'5" dining

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

    136 Monterey Cypress Blvd, Winter Haven, FL 33881
  • /42

    $599,900

    • 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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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 $299,000. If you put a 20% down payment of $59,800 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $1,490 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $64K 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.

Home Trends in Cypresswood, FL

Housing Trends

Median Sale Price
$278,000
Median Single Family Sale Price
$290,000
Median 2 Bedroom Sale Price
$170,000
Average Price Per Sq Ft
$171
Number of Homes for Sale
53
Last 12 months Home Sales
91
Months of Supply
7.00
Median List Price
$299,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-4%
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