Cypresswood Houses for Sale

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  /36

  $274,900

  • 2 Beds
  • 2 Baths
  • 1,755 Sq Ft

  602 Turnberry Ct, Winter Haven, FL 33884

  Welcome to 602 Turnberry Court, a beautifully updated home in the sought-after Cypresswood Golf & Country Club community! This 2-bedroom, 2-bathroom home has been thoughtfully upgraded with all-new flooring, a brand-new roof, a new hot water heater, and all-new appliances. The freshly painted kitchen cabinets give the space a modern and inviting feel, while the freshly painted interior adds a

  

  Manny Quiros

  RE/MAX HERITAGE PROFESSIONALS

  (863) 275-2333

  602 Turnberry Ct, Winter Haven, FL 33884
• 

  

  

  /36

  $350,000

  • 3 Beds
  • 2 Baths
  • 2,048 Sq Ft

  409 Greenfield Rd, Winter Haven, FL 33884

  ***Vacant No Notice Required to see! Your not the only one thinking about it, Act Quick!*** Discover 409 Greenfield Rd—an updated, move-in-ready home located in the gated community of Cypresswood Meadows. This 3-bedroom, 2-bathroom property has been thoughtfully improved with a modern eye for style and functionality. Step inside and enjoy a bright, open layout featuring brand new luxury vinyl

  Chad Lindsey KELLER WILLIAMS REALTY SMART 1

  409 Greenfield Rd, Winter Haven, FL 33884
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  /63

  $320,000

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  571 Saint Andrews Rd, Winter Haven, FL 33884

  "Seller Motivated!!" Welcome to 571 St Andrews Rd in Winter Haven, a beautifully updated 3-bedroom, 2-bathroom home in the highly sought-after Cypresswood Golf & Country Club, a gated community with 24/7 security. This 1,872 sq. ft. residence features an open-concept, split-bedroom floor plan designed for comfort and functionality. The stunning 2022 kitchen boasts solid wood, soft-close cabinets,

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  571 Saint Andrews Rd, Winter Haven, FL 33884
• 

  

  

  /20

  $370,000

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

  830 Turner Ln, Winter Haven, FL 33884

  This stunning 5-bedroom, 2.5-bathroom home, built in 2023, offers 2,254 sq. ft. of modern living space in the growing city of Winter Haven. Featuring brand-new impact windows. The upstairs windows in the front of the home are tinted and have child safety locks. Energy-saving solar panels and a Ring security system are also included. What's not to love about a home that combines style, safety, and

  Ziesha Williams Gatlin EXP REALTY LLC

  830 Turner Ln, Winter Haven, FL 33884
• 

  

  

  /46

  $325,000

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

  312 Inman Blvd, Winter Haven, FL 33881

  Welcome to the home you've been waiting for! This charming, energy-efficient gem is barely two years old and has been meticulously maintained, making it move-in ready. Inside, you’ll be greeted by beautiful tile flooring that flows seamlessly through the main living areas, with carpet in the bedrooms creating a warm, cozy atmosphere. The open-concept kitchen is truly the heart of the home, with

  Kaitlin Sidders

  312 Inman Blvd, Winter Haven, FL 33881
• 

  

  /45

  $399,000

  • 5 Beds
  • 2.5 Baths
  • 2,215 Sq Ft

  271 Inman Blvd, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Room for everyone and peaceful views!! Welcome to 271 Inman Blvd, a pristine 5 bedroom, 2.5 bath home in the new solar-friendly community of Inman Groves, where modern design meets energy efficiency with solar panels that keep utility costs remarkably low. Built in 2024, this better-than-new home sits on a premium corner lot with no rear neighbors,

  Michael Stone THE STONES REAL ESTATE FIRM

  271 Inman Blvd, Winter Haven, FL 33881
• 

  

  /15

  $320,000

  • 3 Beds
  • 2 Baths

  906 Cattleman St, Winter Haven, FL 33884

  Magnificent home located in the Winter Haven community, offering plenty of privacy and tranquility, close to excellent restaurants and amenities. It has three bedrooms and two bathrooms. The property is practically new and the community has a small lake. Geographically close to Lake Hamilton, this is an excellent community for living or renting. It's just a few miles from US27, a major route to

  Guillermo Silva PFS Realty LLC

  906 Cattleman St, Winter Haven, FL 33884
• 

  

  /42

  $334,800

  • 3 Beds
  • 2 Baths
  • 1,605 Sq Ft

  692 Augusta Rd, Winter Haven, FL 33884

  Family home with high end remodel. OPEN CONCEPT! MOVE IN READY! Beautiful 3 bedroom 2 baths plus an additional Florida den room. OPEN FLOOR PLAN in gated and guarded Cypresswood Golf and Country Club Subdivision, one of the best communities in Winter Haven, with views of the 18th hole. Gourmet kitchen offers shaker style all wood cabinets, quartz countertop, tile backsplash and new appliances, as

  Mary Dorsey S & D REAL ESTATE SERVICE LLC

  692 Augusta Rd, Winter Haven, FL 33884
• 

  

  /43

  $329,900

  • 3 Beds
  • 2 Baths
  • 1,940 Sq Ft

  204 Lake Region Blvd S, Winter Haven, FL 33881

  20K Price Drop!!! Welcome to this beautifully updated 3-bedroom, 2-bathroom home with a bonus room in the sought-after Lakes of Gate Region gated community. Nestled among mature landscaping, this home boasts stunning curb appeal, a low HOA, and modern finishes throughout. Step inside to discover a spacious open floor plan filled with natural light and luxury vinyl plank flooring. The gourmet

  Tyler Labod COLDWELL BANKER REALTY

  204 Lake Region Blvd S, Winter Haven, FL 33881
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  /50

  $310,000

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

  1917 Emily Blvd, Winter Haven, FL 33884

  Solar Power Home Enjoy the Low Monthly Electricity bills ---This 4 bedroom home has an open kitchen overlooking the Family room which leads to the back enclosed patio to enjoy the Florida lifestyle. The kitchen includes a breakfast bar. The master bath has a garden tub and a separate shower stall with a large walk in closet. The Roof was REPLACED 2022 when the SOLAR was Installed. Enjoy the large

  Michael Huculak PREFERRED RE BROKERS III

  1917 Emily Blvd, Winter Haven, FL 33884
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  /24

  $329,990

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

  3308 Country Walk Club Cir, Winter Haven, FL 33881

  Currently leased until March 2026. In a vibrant neighborhood, a stunning home built in 2020 awaits. With four spacious bedrooms and two beautifully designed bathrooms, this residence offers comfort and elegance, perfect for families. As you enter, the expansive open floor plan welcomes you. The kitchen features rich espresso-colored cabinets and gleaming granite countertops, complemented by

  Humberto Cuevas LA ROSA REALTY LLC

  3308 Country Walk Club Cir, Winter Haven, FL 33881
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  /37

  $365,000

  • 3 Beds
  • 2 Baths
  • 2,136 Sq Ft

  734 Canberra Rd, Winter Haven, FL 33884

  Welcome to 734 Canberra Rd, Winter Haven, a beautifully remodeled 3-bedroom, 2-bathroom home in the highly desirable Cypresswood Golf & Country Club, a gated community with 24/7 security. This 2,136 sq. ft. residence offers an open-concept design with a split-bedroom floor plan, featuring an amazing chef's kitchen which has been fully remodeled and spacious primary suite with an ensuite recently

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  734 Canberra Rd, Winter Haven, FL 33884
• 

  

  /31

  $340,000

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

  296 Inman Blvd, Winter Haven, FL 33881

  PRICED TO SELL!! SELLER IS VERY MOTIVATED! Say hello to Winter Haven, the vibrant spot between Tampa and Orlando that’s just waiting for you! This area has it all—beautiful lakes, a fun tower, and the world’s largest LEGOLAND nearby. Plus, you’re only a quick drive away from all the attractions and stunning beaches of Central Florida. This home, built in 2023, is practically brand new and

  Rhansel Acevedo Rodriguez EXP REALTY LLC

  296 Inman Blvd, Winter Haven, FL 33881
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  /65

  $338,000

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  768 Canberra Rd, Winter Haven, FL 33884

  ***SELLER IS OFFERING $2,000 TOWARDS AN INTEREST RATE BUYDOWN or TOWARDS BUYER'S CLOSING COSTS and a 1-YEAR HOME WARRANTY (with an acceptable offer)!*** Welcome to 768 Canberra Rd, located in the highly sought-after, gated/guarded community of Cypresswood, where country club living meets comfort and convenience. This beautifully updated 3-bedroom, 2-bathroom home sits on a generous 1/3-acre lot,

  Deanna Stone THE STONES REAL ESTATE FIRM

  768 Canberra Rd, Winter Haven, FL 33884
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  /15

  $350,000

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

  811 Turner Ln, Winter Haven, FL 33881

  This home features a spacious open floor plan, ideal for cooking in the kitchen while entertaining family and friends. The large master bedroom boasts a generous walk-in closet. Located just minutes from world-renowned theme parks and attractions, Inman Groves offers the perfect blend of convenience and Florida’s vibrant lifestyle. Enjoy stunning local lakes right in your backyard, and take

  Yanira Suarez LPT REALTY, LLC

  811 Turner Ln, Winter Haven, FL 33881
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  /73

  $339,000

  • 3 Beds
  • 2 Baths
  • 2,086 Sq Ft

  3226 Oak Tree Ln, Winter Haven, FL 33884

  Price improvement!! Motivated sellers!! Welcome to this beautiful and very well maintained, one owner home with a genuine pride of ownership! Which is located in the Oak Grove area in Cypreswood! This is a very well established, gated, golf community with A 24 hour security guard at the front gate. This home was custom built by John Wood. It is the Breezewood model. 3bedrooms 2 full baths and a

  Ann Heaton CHARLES RUTENBERG REALTY ORLANDO

  3226 Oak Tree Ln, Winter Haven, FL 33884
• 

  

  /22

  $309,400

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

  3136 Country Club Cir, Winter Haven, FL 33881

  The sellers are motivated and just reduced the price. Are you looking for your dream home, look no further. This 3 bedroom 2 bath 2 car garage home is move-in ready. It looks like the day it was built and still offers the bonded builder warranty. As you walk in the front door your hallway leads into the open floorplan. This makes the home perfect for entertaining your guests. The kitchen features

  Stephanie Fitzgerald HARPER REALTY FL, LLC

  3136 Country Club Cir, Winter Haven, FL 33881
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  /43

  $330,000

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft

  680 Augusta Rd, Winter Haven, FL 33884

  PRICE REDUCTION. SELLERS OFFERING $5,000 CONCESSION TOWARD INTEREST RATE BUY DOWN, CLOSING COSTS OR CASH BACK AT CLOSING. Beautiful home in Cypresswood gated community. Twenty four hour manned gate. Home has newly installed ADT system. This is a golf community with club house, restaurant, bar, pool and tennis/pickle ball courts. THIS HOME COMES FULLY FURNISHED!!! Home could be sold

  Darlene Bice TOWN & COUNTRY REAL ESTATE

  680 Augusta Rd, Winter Haven, FL 33884
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  /49

  $284,500

  • 2 Beds
  • 2 Baths
  • 1,367 Sq Ft

  628 Wexford Ct, Winter Haven, FL 33884

  LIVE THE FLORIDA LIFESTYLE IN CYPRESSWOOD - Make every moment count in this beautifully updated two-bedroom, two-bath home in the resort-style community of Cypresswood Golf and Country Club. Step into the bright and spacious interior, featuring a contemporary open-concept layout, designed for effortless entertaining, and truly the heart of this home. Warm wood laminate floors flow throughout,

  Joy Desmond REMAX EXPERTS

  628 Wexford Ct, Winter Haven, FL 33884
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  /46

  $300,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,725 Sq Ft

  375 Troon Ct, Winter Haven, FL 33884

  The property you are inquiring about is located in Winter Haven, FL in the community of CypressWood Golf and Country Club Community, Polk County. This is a picturesque property with the backyard Lanai overlooking the 11th Green of an 18-hole golf course, driving range also has The Cypresswood Pub and Eatery with a patio. This home is situated near the amenities of the pool, tennis courts,

  Joan Diaz REMAX EXPERTS

  375 Troon Ct, Winter Haven, FL 33884
• 

  

  /23

  $199,900

  • 2 Beds
  • 2 Baths
  • 1,139 Sq Ft

  697 Broadmoor Cir Unit O71, Winter Haven, FL 33884

  Welcome to 697 Broadmoor Circle—an immaculately kept 2-bedroom, 2-bathroom villa offering maintenance-free living right on the 10th tee of Cypresswood’s beautiful golf course. This home blends comfort, style, and leisure in one of Winter Haven’s most desirable gated golf communities. Step inside to a bright, inviting interior where the spacious living room features a wet bar, perfect for

  Andrew Fearn BHHS FLORIDA PROPERTIES GROUP

  697 Broadmoor Cir Unit O71, Winter Haven, FL 33884
• 

  

  /15

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,262 Sq Ft

  2792 Whispering Trails Dr, Winter Haven, FL 33884

  This 3-bedroom, 2-bathroom home is located in the gated Whispering Trails community and offers a distinctive design with unique floor tiles throughout. The open layout provides a spacious feel, while the well-sized bedrooms ensure comfort and functionality.The kitchen is equipped with modern appliances, making meal preparation easy and efficient. The home’s thoughtful design allows for

  Gladys Burgos FCG REALTY

  2792 Whispering Trails Dr, Winter Haven, FL 33884
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  /18

  $249,000

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

  3115 Whispering Trails St, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Fantastic home in sought after location! This home has Fresh Interior Paint, Fresh Exterior Paint. Discover a bright interior tied together with a neutral color palette. Relax in your primary suite with a walk in closet included. The primary bathroom features plenty of under sink storage waiting for your home organization needs. The back yard is the

  GREGORY BLACKALL OPENDOOR BROKERAGE LLC

  3115 Whispering Trails St, Winter Haven, FL 33884
• 

  

  /13

  $245,000

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

  423 Greenfield Rd, Winter Haven, FL 33884

  Nice Patio home in gated Cypresswood neighborhood. Home has newer ac, tankless hot water heater, large room on back that could be converted to a third bedroom or used as an office. Golf Course neighborhood, you can hop on your golf cart and be at the course within 3 minutes! Great place to retire in the Florida sun. Come take a look and see for yourself.

  Chace Vaughn TOWN & COUNTRY REAL ESTATE

  423 Greenfield Rd, Winter Haven, FL 33884
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  /67

  $1,399,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 3 Baths
  • 3,309 Sq Ft

  3640 Crump Rd, Winter Haven, FL 33881

  LAKEFRONT PARADISE WITH RESORT-STYLE AMENITIES! Nestled on Lake Hamilton with NO HOA, this 4-bed, 3-bath home on 1.23 acres offers the ultimate lakeside lifestyle. Bring your boat and jet skis and enjoy the convenience of a dock with an electric, covered BOAT LIFT, and built-in bench—perfect for fishing!Step through the French doors to the sparkling SALTWATER PebbleTec pool, featuring iridescent

  Laura Kettle REGENCY REAL ESTATE LLC

  3640 Crump Rd, Winter Haven, FL 33881
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  /27

  $279,900 Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,746 Sq Ft

  579 Saint Andrews Rd, Winter Haven, FL 33884

  Enjoy unobstructed fairway views from this well maintained and updated 2 bedroom 2 bath home located on the 11th Fairway at Cypresswood Golf and Country Club in Southeast Winter Haven.Enjoy your morning coffee in the air conditioned Florida room as the sun rises over the golf course along with an occasional visit from the Sandhill Cranes.Features include ceramic tile flooring throughout,

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  579 Saint Andrews Rd, Winter Haven, FL 33884
• 

  

  /39

  $247,500

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  2246 Firestone Place, Winter Haven, FL 33884

  FANTASTIC GOLF VIEW...PICTURE PERFECT HOME. NEW KITCHEN APPLIANCES, GRANITE COUNTERS, AND NO CARPETING. SPLIT BEDROOM PLAN WITH TWO FULL BATHROOMS AND PLENTY OF STORAGE. BIG FLORIDA/FAMILY ROOM WITH GORGEOUS VIEWS OF THE GOLF COURSE. REAR PATIO PERFECT FOR GRILLING OUT. DRIVE UP TO YOUR HOME IN YOUR GOLF CART! FRONT COURTYARD IS PRIVATE AND CHARMING. THE COVERED PARKING CARPORT IS DIRECTLY IN

  Patricia France HAPPY DAYS REALTY LLC

  2246 Firestone Place, Winter Haven, FL 33884
• 

  

  /33

  $260,000

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

  2809 Wingfoot Ct, Winter Haven, FL 33884

  AWESOME GOLF VILLA WITH FAIRWAY VIEW 8TH HOLE. WELL MAINTAINED HOME. ALL APPLIANCES REMAIN. TANKLESS WATER HEATER. FRESH PAINT. GENEROUS SIZED ROOMS, BEAUTIFUL SUNROOM/FAMILY ROOM WITH OUTDOOR PATIO OVERLOOKS GOLF. FRONT COURTYARD IS PRIVATE AND INVITING. YOUR OWN COVERED PARKING, CARPORT KEEPS CAR PROTECTED. PRIVATE ENTRANCE. GUARD GATED COMMUNITY, LOW HOA. COMMUNITY POOL, TENNIS AND GOLF. GOLF

  Patricia France HAPPY DAYS REALTY LLC

  2809 Wingfoot Ct, Winter Haven, FL 33884
• 

  

  /19

  $260,000

  • 2 Beds
  • 2 Baths
  • 1,660 Sq Ft

  460 Pinehurst Ct, Winter Haven, FL 33884

  CYPRESSWOOD GOLF CLUB PATIO HOME! Come enjoy the beautiful weather of Central Florida in an affordable golf community home. Large 2BR/2BA home on quiet street. Walt to the pool, tennis courts, and pickleball. Stroll to the clubhouse pub for lunch or dinner and enjoy the sunset over the golf course. Large (1660 SF MOL) home with real wood kitchen cabinets, built in bookshelves in the living

  Sharon Watson CENTURY 21 WATSON & MYERS REALTY

  460 Pinehurst Ct, Winter Haven, FL 33884
• 

  

  /91

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  121 Greenfield Rd, Winter Haven, FL 33884

  Truly one of a kind home in the sought after neighborhood of Cypresswood Golf and Country Club. This is the only home with a fenced in yard that is on the award winning golf course! Enjoy your morning coffee out by the pristine pool that overlooks the course. This beautifully maintained home has something for everyone. The spacious kitchen with multiple upgrades and new appliances in the last

  Stacy Tuttle REMAX EXPERTS

  121 Greenfield Rd, Winter Haven, FL 33884
• 

  

  /22

  $259,900 Open Sat 11AM - 1PM

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

  2076 Whispering Trails Blvd, Winter Haven, FL 33884

  You will love: BRAND NEW FLOORING THROUGHOUT! ~ Freshly painted ~ New roof (2022) ~ HVAC (2023) ~ Solar attic fan for energy efficiency ~ Transferable warranty covering all appliances, including the water heater ~ Just 10 minutes from Legoland! ~ No rear neighbors! ~ No long-term rental restrictions! ~ NO CDD! ~ Not in a flood zone! ~ GATED COMMUNITY with LOW HOA! ~ Motivated sellers!Welcome home

  Yaima Noa Oliva MARK SPAIN REAL ESTATE

  2076 Whispering Trails Blvd, Winter Haven, FL 33884
• 

  

  /29

  $444,000

  • 4 Beds
  • 3 Baths
  • 2,328 Sq Ft

  141 Greenfield Rd, Winter Haven, FL 33884

  Offering $5,000 in seller concessions! Welcome to your dream home! Nestled on a picturesque golf course, this beautiful 4-bedroom, 3-bathroom home offers the perfect combination of space, comfort, and tranquility. Step inside to discover a spacious open floor plan featuring lots of natural light and breathtaking views of the lush greens and fairways out of the back. The kitchen has a passthrough

  Aaron Clark COVENANT REALTY

  141 Greenfield Rd, Winter Haven, FL 33884
• 

  

  /58

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,764 Sq Ft

  2350 Crump Rd, Winter Haven, FL 33881

  EXTRAORDINARY RESIDENCE ON LAKE HAMILTON is inviting and spacious with classy finishes throughout its 2,764 sq ft living area. This pool home provides 4BD/ 3BA, great entertaining space and is situated on .83 acres waterfront property. A gracious foyer leads into the home's fabulous layout of grand openness linking the formal living room and formal dining room to the centered kitchen. The living

  Erin Floyd COLDWELL BANKER REALTY

  2350 Crump Rd, Winter Haven, FL 33881
• 

  

  /15

  $230,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  2284 Firestone Place, Winter Haven, FL 33884

  **"Embrace comfort and elegance in this beautiful 2-bedroom, 2-bathroom villa, offering nearly 1,400 sq. ft. of well-designed living space. Enjoy a spacious living and dining combo, a bright Florida room, and a master suite with a walk-in closet that opens to the Florida room—showcasing breathtaking golf course views and a peaceful ambiance. Situated in an exclusive, gated community with manned

  Sherifa Campbell MERVIN MORGAN REALTY & PROPERTY MANAGEMENT LLC

  2284 Firestone Place, Winter Haven, FL 33884
• 

  

  /26

  $290,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 3 Baths
  • 2,370 Sq Ft

  42 Enclave Dr, Winter Haven, FL 33884

  Luxury, Leisure & Little Maintenance—Welcome to Cypresswood Living!?2 primary suites! ?Excellent floorplan! ?Private screened porch/patio! ?Low maintenance home!Nestled in the highly coveted Cypresswood Golf and Country Club community, this charming 3-bedroom, 3-bathroom home is where elegance meets ease. Step inside through your very own 2-car garage or follow your private sidewalk to

  Andrea Anderson S & D REAL ESTATE SERVICE LLC

  42 Enclave Dr, Winter Haven, FL 33884
• 

  

  /13

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft

  201 Cleveland Ave, Winter Haven, FL 33881

  Here's a chance to purchase a home with 7 lots + 15' of another lot to the north of the 7 lots. Home has had some birthdays & needs renovation/repairs in several areas. All lots are included and part of the land is partially chain-link fenced. Property is located near Dundee Road which provides access to Winter Haven to the west or US 27 to the east. While some may call this home a

  Tim Irby TOWN & COUNTRY REAL ESTATE

  201 Cleveland Ave, Winter Haven, FL 33881
• 

  

  /19

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft

  620 Wexford Ct, Winter Haven, FL 33884

  Welcome to your dream home-Step inside to discover this spacious and stunning MOVE-IN READY 2 bed/ 2 bath with an oversize 2 car garage located in the desirable 24hr Gated Cypress Club Neighborhood. Which offers the perfect blend of comfort and convenience with an array of neighborhood amenities including an amazing golf community, a park, pool, tennis courts, fitness center, dine-in-club house

  Pamela Brady LPT REALTY, LLC

  620 Wexford Ct, Winter Haven, FL 33884
• 

  

  /55

  $590,000

  • 4 Beds
  • 3 Baths
  • 3,257 Sq Ft

  19 Meadowlake Ct, Winter Haven, FL 33884

  Step into luxury with this stunning ranch-style home in the gated Cypresswood golf community! Nestled on a peaceful cul-de-sac, this spacious 4-bedroom home blends modern elegance with timeless charm, making it the perfect retreat.Inside, wood-look tile flooring flows throughout the main living areas, offering both durability and style. The gourmet kitchen is a dream, featuring brand-new

  Rebecca Redman Hamaoui REAL BROKER, LLC

  19 Meadowlake Ct, Winter Haven, FL 33884
• 

  

  /53

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,590 Sq Ft

  2214 Palma Ceia Rd, Winter Haven, FL 33884

  Welcome to 2214 Sawgrass Ct, a meticulously maintained 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Built in 1987, this 1,590 square-foot residence offers a harmonious blend of comfort, style, and convenience, making it an ideal choice for those seeking a serene yet active lifestyle. Upon entering, you're greeted by a

  Jared Dunn LPT REALTY, LLC

  2214 Palma Ceia Rd, Winter Haven, FL 33884
• 

  

  /25

  $287,000

  • 4 Beds
  • 2.5 Baths
  • 2,237 Sq Ft

  2320 Whispering Trails Place, Winter Haven, FL 33884

  $21,000 PRICE REDUCTION! Stunningly Refreshed & Move-In Ready! Welcome to your dream home in the exclusive gated community of Whispering Trails! This ABSOLUTELY BEAUTIFUL residence is brimming with upgrades, including a brand new A/C for year-round comfort. As you step inside, you’ll be greeted by gleaming laminate floors that flow seamlessly throughout the first floor, setting the stage for

  Donald Toldson OLYMPUS EXECUTIVE REALTY INC

  2320 Whispering Trails Place, Winter Haven, FL 33884

Showing Results 1 - 40, Page 1 of 2

About 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

Home Trends in Cypresswood, FL

On average, homes in Cypresswood, Winter Haven sell after 72 days on the market compared to the national average of 47 days. The average sale price for homes in Cypresswood, Winter Haven over the last 12 months is $328,866, up 1% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)

$284,500

Median Single Family Price

$309,000

Median 2 Bedroom Price

$189,750

Average Price Per Sq Ft

$183

Number of Homes for Sale

66

Last 12 months Home Sales

80

Months of Supply

9.90

Median List Price

$308,000

Median Discount From 1st List Price

4%

Median Home Sale Price YoY Change

-11%