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Cypresswood Homes for Sale

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  • /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
  • /20

    $215,000

    • 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
  • /34

    $230,000

    • 3 Beds
    • 2 Baths
    • 1,268 Sq Ft

    2893 Whispering Trails Dr, Winter Haven, FL 33884

    This cozy home offers a warm and inviting layout, perfect for anyone who prefers comfort and easy living. It features a functional floor plan with a modern kitchen, bright bedrooms, and low-maintenance spaces that make everyday life simple. Ideally located near US-27, US-17, SR-540, and with quick access to I-4, you’re just a short drive from Orlando, Tampa, Disney, Legoland, lakes, parks,

    Jenny Caso MY REALTY GROUP, LLC.

    2893 Whispering Trails Dr, Winter Haven, FL 33884
  • /34

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,376 Sq Ft

    3201 Oak Tree Ln, Winter Haven, FL 33884

    Schedule your showing now for this bright and airy 3-bedroom, 2-bath split-plan gem in the coveted, guard-gated community of Cypresswood Golf and Country Club. Reroof was completed in 2019 as well as the installation of a quadruple water filtration system, and upgraded irrigation system. The home features a screeded in Lanai, 2 car garage, indoor laundry room off of garage, and the primary

    Shalisa Muehlberger S & D REAL ESTATE SERVICE LLC

    3201 Oak Tree Ln, Winter Haven, FL 33884
  • /15

    $299,000

    • 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
  • /51

    $399,800

    • 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
  • /49

    $324,000

    • 3 Beds
    • 2 Baths
    • 2,076 Sq Ft

    533 Saint Andrews Rd, Winter Haven, FL 33884

    Florida living at its best! The spacious golf course home has three bedrooms two baths and is located in the gated, guarded, golf course community of Cypresswood. Situated on an oversized, landscaped lot on the 11th tee, this home boast soaring ceilings, open floor plan and a bright airy eat in kitchen. The luxurious master garden bath features dual sink vanity with solid surface top and large

    Lynn Arthur FAITH AND FAMILY REALTY LLC

    533 Saint Andrews Rd, Winter Haven, FL 33884
  • /45

    $129,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    284 Siberian Cypress Creek Cir, Winter Haven, FL 33881

    This 2022 home offers 1344 sq ft of living space, Immaculate and well-maintained. It has three bedrooms and two bathrooms with an open floor plan, perfect for entertaining family/friends or just relaxing. Additional living space can be found in the raised Florida room, along with the covered patio outdoors. Have a cookout and invite neighbors and friends! Key features of this home include a large

    Cynthia Cole Sunset Home Sales

    284 Siberian Cypress Creek Cir, Winter Haven, FL 33881
  • /70

    $139,900

    • 3 Beds
    • 3 Baths
    • 1,988 Sq Ft

    164 Monterey Cypress Blvd Unit 121, Winter Haven, FL 33881

    THIS EXTRA LARGE, VERY WELL CARED FOR, UPDATED, 2010 NOBILITY ERICA IS JUST WAITING FOR YOUR ARRIVAL WITH 3 BEDROOMS, 3 BATHS, TOTALING 1848 INTERIOR SQUARE FT, PLUS A LARGE ENCLOSED FLORIDA ROOM WITH BEAUTIFUL VIEWS, MAKING THE SQUARE FOOTAGE OVER 1900! This Home has 3 Bedrooms and 3 Full Baths. The 2nd and 3rd Bedrooms are Tucked Away in the Rear left of The Home. Perfect for Long-Term Guests

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

    164 Monterey Cypress Blvd Unit 121, Winter Haven, FL 33881
  • /19

    $300,000

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

    780 Overlook Grove Dr, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Smart & Sustainable: Fully Updated 4BD/2BA Home with $30 Electric Bill!780 Overlook Grove Drive, Winter Haven, FL Welcome home to this beautifully renovated 4-bedroom, 2-bathroom single family residence, perfectly situated on a prime corner lot within a tranquil cul-de-sac. This property is not just gorgeous; it's designed for exceptional

    Team Papin FLORIDA LUXURY REALTY INC

    780 Overlook Grove Dr, Winter Haven, FL 33884
  • /28

    $229,990

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

    1062 Medinah Dr, Winter Haven, FL 33884

    Location, Lifestyle & Leisure — All in One!Discover the perfect blend of comfort, convenience, and community in this beautifully maintained villa located in a sought-after gated Cypresswood Community with 24-hour security. Enjoy resort-style living with access to championship golf, tennis courts, a fitness center, community pool, on-site restaurant, and so much more — all just steps from your

    Doug DeWitt NEW HOME ADVANTAGE LLC

    1062 Medinah Dr, Winter Haven, FL 33884
  • /59

    $150,000

    • 2 Beds
    • 2 Baths

    353 Siberian Cypress Cir, Winter Haven, FL 33881

    Welcome home to this impeccable 2-bedroom 2-bath sanctuary awaiting your arrival! This STUNNING 2023-built residence is nestled in one of Winter Haven's most sought-after 55+ communities, Cypress Creek Village. **LOW LOT LEASE $660** and Close to all! With Palm trees lining the streets, this lovely community offers resort-style living at its finest. FULLY FURNISHED with well-appointed features,

    Linda Wilson Sunset Home Sales

    353 Siberian Cypress Cir, Winter Haven, FL 33881
  • /100

    $575,000

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

    1988 Crossroads Blvd, Winter Haven, FL 33881

    This Beautiful 4-bedroom,3-bath home with additional office offers the perfect blend of style and comfort. Featuring hardwood floors and tile throughout the main living areas, cozy carpeted bedrooms, and an open floor plan with high ceilings that fill the home with natural light. The kitchen boasts elegant granite countertops, while the renovated master bathroom showcase a huge glass shower,

    Cindy Thornton AGILE GROUP REALTY

    1988 Crossroads Blvd, Winter Haven, FL 33881
  • /32

    $240,000

    • 2 Beds
    • 2 Baths
    • 2,394 Sq Ft

    241 Greenfield Rd, Winter Haven, FL 33884

    Tee up your creativity with this spacious 2 bedroom, 2 bath home offering over 2,400 sq ft of living space right on the 13th green! Set on an oversized lot in a gated and guarded community, this home is packed with potential and ready for your personal touch. From the grand double-door entry to the beautiful brick fireplace, there’s timeless charm waiting to shine again. The gourmet kitchen is

    Jackie Mazurowski KELLER WILLIAMS REALTY SMART 1

    241 Greenfield Rd, Winter Haven, FL 33884
  • /71

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,465 Sq Ft

    10 Meadowlake Ct, Winter Haven, FL 33884

    This property located in the gated golf community of Cypresswood is the perfect home for the family to settle in and enjoy. This home is a 4-bedroom, 2.5- bath pool home located on a corner lot and sitting in front of 13th Fairway. This home has had recent luxury vinyl throughout the house, new kitchen countertops, new ceiling fans, and fresh paint on the interior. Exterior uplifts are new

    Renee Butler BROKERS REALTY OF CENTRAL FLOR

    10 Meadowlake Ct, Winter Haven, FL 33884
  • /42

    $629,000

    • 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
  • /53

    $400,000

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

    126 Lake Region Cir, Winter Haven, FL 33881

    Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a study, library

    Carol Sheil JUDY B CLEAVES PROPERTIES INC

    126 Lake Region Cir, Winter Haven, FL 33881
  • /45

    $325,000

    • 3 Beds
    • 2 Baths
    • 2,004 Sq Ft

    708 Canberra Rd, Winter Haven, FL 33884

    Welcome Home! Step into this beautiful 3-bedroom, 2-bath home located in the heart of Winter Haven — nestled in a stunning golf course community with breathtaking views right from your backyard. As you enter, you’ll find a spacious guest bedroom and full guest bathroom to your left, along with an additional room that can serve as a home office or extra bedroom. Continue into the open-concept

    Stephanie Class Cordero EXP REALTY LLC

    708 Canberra Rd, Winter Haven, FL 33884
  • /18

    $238,500

    • 2 Beds
    • 2 Baths
    • 1,634 Sq Ft

    374 Troon Ct, Winter Haven, FL 33884

    BRAND NEW ROOF AND NEW WATER HEATER TO BE INSTALLED NOVEMBER, 2025.Enjoy the Florida Country Club Lifestyle in this 2 bedroom patio home featuring a foyer with wet bar, spacious living room, dining area, kitchen with wood cabinets and converted Florida room, ideal as a den, office or play room.Additional amenities include an expansive master bedroom, 2 car garage with door opener and

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    374 Troon Ct, Winter Haven, FL 33884
  • /51

    $139,900

    • 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
  • /18

    $220,000

    • 2 Beds
    • 2 Baths
    • 1,432 Sq Ft

    423 Greenfield Rd, Winter Haven, FL 33884

    Great house in gated Cyrpresswood neighborhood, close to US 27 and I 4, gplf community with multiple courses in the neighborhood. Fresh paint on the house, roof is right at 10 years old, A/C is about 7 years old estimated. Great place to live with clubhouse and restaurant in neighborhood, community pool, no need to leave the neighborhood. Nice 2 bed/2bath with Florida room that has the

    Chace Vaughn TOWN & COUNTRY REAL ESTATE

    423 Greenfield Rd, Winter Haven, FL 33884
  • /33

    $149,000

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

    1222 Cypress Vine Rd Unit 287, Winter Haven, FL 33884

    CYPRESS CREEK VILLAGE #287 - 2 BED + DEN / 2 BATH / 1,647 SF. / $149,900 CUSTOM BUILT HOME with Double Driveway! This OPEN FLOOR PLAN home is furnished and move-in-ready! This immaculately maintained home is VERY SPACIOUS! It features an open floor plan, integrated Florida Room, and screened front porch. This sought after Model has large rooms throughout. The spacious master

    Jennifer Meyers CRF Communities

    1222 Cypress Vine Rd Unit 287, Winter Haven, FL 33884
  • /33

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,776 Sq Ft

    368 Niblick Cir, Winter Haven, FL 33881

    Welcome to this immaculate one-owner home. Purchased as a second home, this was rarely used and is in like-new condition! Located in the sought-after Gates of Lake Region community, this home offers comfort, style, and peace of mind in a well-established neighborhood. Step through the screened front entry into a welcoming foyer that opens to a spacious living and dining area. The large kitchen

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 663-2067

    368 Niblick Cir, Winter Haven, FL 33881
  • /52

    $495,000

    • 4 Beds
    • 2 Baths
    • 2,756 Sq Ft

    2405 Melrose St, Winter Haven, FL 33881

    Welcome to this stunning 4-bedroom, 2-bath pool home that blends elegance, comfort, and functionality. From the moment you enter through the double doors, you’re greeted with an open floor plan and wood plank laminate flooring throughout, creating a warm and inviting atmosphere. The home features multiple living and dining spaces, including a formal living room, formal dining room (or

    Stacey Towns STACEY TOWNS REALTY LLC

    2405 Melrose St, Winter Haven, FL 33881
  • /32

    $98,800

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

    502 Leyland Cypress Way, 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

    Jennifer Meyers CRF Communities

    502 Leyland Cypress Way, Winter Haven, FL 33881
  • /20

    $89,500

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

    1008 Heartwood Cypress Dr, Winter Haven, FL 33881

    CYPRESS CREEK VILLAGE #222 / 2 BED / 2 BATH / 1,000 SF / $89,500 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 breakfast nook, living room, and light filled

    Jennifer Meyers CRF Communities

    1008 Heartwood Cypress Dr, Winter Haven, FL 33881
  • /25

    $264,000

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft

    511 Pebble Springs Ct, Winter Haven, FL 33884

    Experience refined living in this beautifully updated 2-bedroom residence, perfectly situated within the coveted gated community of Cypresswood Golf & Country Club. The home has been thoughtfully maintained and enhanced with a long list of valuable updates, including a Roof (2019), A/C (2023), Tankless Water Heater (2024), Washer & Dryer (2024), Dishwasher (2024), Range (2024), and Microwave

    Gina Morgando MORGANDO REALTY SERVICES, LLC

    511 Pebble Springs Ct, Winter Haven, FL 33884
  • /26

    $136,900

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

    1201 Cypress Vine Rd Unit 297, Winter Haven, FL 33881

    CYPRESS CREEK VILLAGE #297 - 2BED / 2 BATH / 1,200 SF. / $136,900 POND VIEW HOME with Double Driveway! Golf cart included! This MODERN, TURNKEY HOME is furnished and move-in-ready for you! This immaculately maintained home is only 5 years old! It features an open floor plan, air-conditioned four-season Florida Room and lower screened lanai - all of which have a tranquil pond view. This home has a

    Jennifer Meyers CRF Communities

    1201 Cypress Vine Rd Unit 297, Winter Haven, FL 33881
  • /62

    $785,000 New Construction

    • 3 Beds
    • 3 Baths
    • 2,541 Sq Ft

    4030 Palma Ceia Cir, Winter Haven, FL 33884

    Luxury New Construction in Cypresswoods!Discover the perfect blend of modern design and upscale living in this brand-new 3-bedroom, 3-bath home with a bonus room and over 2,450 sq. ft. of heated space. Crafted with attention to detail, this residence showcases soaring ceilings, designer tile floors, granite countertops, and a sleek open-concept layout. The heart of the home flows effortlessly

    Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

    4030 Palma Ceia Cir, Winter Haven, FL 33884
  • /34

    $234,900

    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft

    749 Overlook Grove Dr, Winter Haven, FL 33884

    Welcome to 749 Overlook Grove Dr in Winter Haven! This charming home offers a desirable split floor plan with 3 bedrooms and 2 bathrooms, providing both comfort and functionality. The open layout makes it easy to entertain, while the spacious kitchen flows seamlessly into the living and dining areas. The primary suite includes its own private bathroom. Outside, you’ll find a fenced backyard—ideal

    Derek McGehee ALL COUNTY POLK PROPERTY MANAG

    749 Overlook Grove Dr, Winter Haven, FL 33884
  • /35

    $59,900

    • 1 Bed
    • 1 Bath

    4320 Dundee Rd Unit 36, Winter Haven, FL 33884

    This IMMACULATE Beach Bungalow is the Perfect Dream Home come true! Located in the Pristine ALL-AGE community of Southern Duck RV Resort in central Florida! With Exquisite curb appeal, first notice the pristine landscaping, clean-coated driveway under carport, and outdoor back patio with raised pavers for an evening under the warm Florida stars! This adorable cottage offers every modern

    Linda Wilson Sunset Home Sales

    4320 Dundee Rd Unit 36, Winter Haven, FL 33884
  • /44

    $153,900

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

    220 Monterey Cypress Blvd Unit 145, Winter Haven, FL 33884

    SPACIOUS, STYLISH & SERENE ... Your PEACE CREEK RETREAT Welcome to CYPRESS CREEK VILLAGE, one of Central Florida's NEWEST 55+ active ADULT, PET-FRIENDLY communities, where lifestyle comes first. Located in WINTER HAVEN, this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $804.00, which includes full access to RESORT-STYLE amenities for you and

    Tammy Barnhart Renee's Resales

    220 Monterey Cypress Blvd Unit 145, Winter Haven, FL 33884
  • /45

    $110,000

    • 2 Beds
    • 2 Baths
    • 1,184 Sq Ft

    1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881

    WELCOME to Your Stunning DREAM HOME... Welcome to CYPRESS CREEK VILLAGE, one of Central Florida's NEWEST 55+ active ADULT, PET-FRIENDLY communities, where lifestyle comes first. Located in WINTER HAVEN, this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $724, which includes full access to RESORT-STYLE amenities for you and your guests to enjoy.

    Tammy Barnhart Renee's Resales

    1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881
  • /65

    $139,900

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

    1182 Heartwood Cypress Dr, Winter Haven, FL 33884

    MUSTANG RED GOLF CART INCLUDED. FRESHLY PAINTED INSIDE, 55 Plus Active Lifestyle Community. Seller is motivated. Only 6 years old which mean there is still plenty of life on the roof. LOW LOT FEE $521/month. This home has furniture that you can keep or can be removed if you have no need for it. You'll have all matching appliances, spacious shed, Golf CART INCLUDED, all season sunroom, laundry

    Daniel Butler Sun Realty of Florida

    1182 Heartwood Cypress Dr, Winter Haven, FL 33884
  • /24

    $390,000

    • 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

    Agent Photo

    Rafael Ortiz

    KELLER WILLIAMS LEGACY REALTY

    (863) 375-8538

    814 Turner Ln, Winter Haven, FL 33881
  • /54

    $319,500

    • 2 Beds
    • 2 Baths
    • 1,922 Sq Ft

    560 Saint Andrews Rd, Winter Haven, FL 33884

    Fresh new price — your opportunity to own in Cypresswood just got better! Welcome to 560 St Andrews Rd in Cypresswood Golf & Country Club!This beautiful patio home is truly move-in ready, offering 2 bedrooms, 2 bathrooms, and plenty of stylish updates.From the moment you arrive, you’ll be impressed by the brick-paver driveway, lush landscaping, and inviting curb appeal. Inside, the spacious

    Corinna Weaver CROSBY & ASSOCIATES, INC.

    560 Saint Andrews Rd, Winter Haven, FL 33884
  • /58

    $203,000

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

    1012 Medinah Dr, Winter Haven, FL 33884

    Fresh new price — your opportunity to own in Cypresswood just got better! Seller will pay the first year’s HOA fees! Welcome to The Tennis Villas! Nestled in the highly desired Cypresswood Golf & Country Club, this gated community with 24/7 security offers the perfect blend of comfort, convenience, and resort-style living.At the entry, a classic wrought iron gate opens to a private front patio,

    Corinna Weaver CROSBY & ASSOCIATES, INC.

    1012 Medinah Dr, Winter Haven, FL 33884
  • /22

    $249,900

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

    2033 Whispering Trails Blvd, Winter Haven, FL 33884

    Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 15 minutes from the exciting attractions of Legoland, and less than an hour from the magical world of Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and amenities. This

    Vivian Ortiz OAK AVENUE REAL ESTATE LLC

    2033 Whispering Trails Blvd, Winter Haven, FL 33884
  • /33

    $255,000

    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft

    3025 Silverado Terrace, Winter Haven, FL 33884

    THIS HOME QUALIFIES FOR 0% DOWN !! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also

    Malak Benbachir KELLER WILLIAMS REALTY SMART 1

    3025 Silverado Terrace, Winter Haven, FL 33884
  • /69

    $385,000

    • 5 Beds
    • 2.5 Baths
    • 2,254 Sq Ft

    950 Cattleman St, Winter Haven, FL 33884

    Welcome to this charming corner lot home in the heart of Winter Haven! Featuring a bright and open floor plan, this residence offers comfortable living with modern touches throughout. The spacious kitchen seamlessly connects to the dining and living areas, making it ideal for both everyday living and entertaining. Retreat to the primary suite with its own private bath, while additional bedrooms

    Gisele Abrantes Trautman SERHANT

    950 Cattleman St, Winter Haven, FL 33884

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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 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 $311,500. If you put a 20% down payment of $62,300 and had a 30-year fixed mortgage with an interest rate of 6.26%, 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:
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 33880.
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
$291,250
Median Single Family Sale Price
$310,000
Median 2 Bedroom Sale Price
$176,250
Average Price Per Sq Ft
$170
Number of Homes for Sale
55
Last 12 months Home Sales
88
Months of Supply
7.50
Median List Price
$311,500
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-1%
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