Cypresswood Homes

• 

  

  

  /19

  $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

  Vivian Ortiz OAK AVENUE REAL ESTATE LLC

  2033 Whispering Trails Blvd, Winter Haven, FL 33884
• 

  

  

  /16

  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,511 Sq Ft
  • House for Rent

  2700 Crump Rd, Winter Haven, FL 33881

  Lakefront Living at Its Finest!Discover the perfect blend of comfort, convenience, and stunning natural beauty with this 3-bedroom, 2-bath home located on the highly sought-after Lake Hamilton. This property offers unbeatable location — just minutes from shopping, dining, and entertainment, yet far enough to enjoy peace and privacy away from the city bustle.Recently updated, this home delivers

  Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

  2700 Crump Rd, Winter Haven, FL 33881
• 

  

  /2

  $242,500 Sold Jun 27, 2025

  • 1,176 Sq Ft
  • $206/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2013

  713 Overlook Grove Dr, Winter Haven, FL 33884

  Motivated Seller – Priced to Sell! Bring All Offers!Welcome to 713 Overlook Grove Dr in Winter Haven – a beautifully maintained open-concept home that offers both comfort and value. The seller is extremely motivated, and this home is priced to move quickly, so don’t wait—schedule today!This spacious residence features a brand-new roof and comes with paid-off solar panels at

  Austin Waters KELLER WILLIAMS REALTY SMART 1

  713 Overlook Grove Dr, Winter Haven, FL 33884
• 

  

  

  /35

  Est $244,241 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,253 Sq Ft

  2873 Whispering Trails Dr, Winter Haven, FL 33884

  2873 Whispering Trails Dr, Winter Haven, FL 33884
• 

  

  

  /33

  $269,900

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

  3025 Silverado Terrace, Winter Haven, FL 33884

  THIS HOME QUALIFIES FOR 0% DOWN and seller willing to give 2% in closing cost assistant!! 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

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  3025 Silverado Terrace, Winter Haven, FL 33884
• 

  

  /12

  $2,200 per month

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • House for Rent

  3240 Country Walk Club Cir, Winter Haven, FL 33881

  Brochure Available, Docs Available, Floor Plan Available

  Moises Dominguez, LLC TBO REAL ESTATE PARTNERS INC

  3240 Country Walk Club Cir, Winter Haven, FL 33881
• 

  /2

  $254,500 Sold Jun 27, 2025

  • 1,432 Sq Ft
  • $178/SF
  • 78 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  2076 Whispering Trails Blvd, Winter Haven, FL 33884

  BRING YOUR OFFERS! 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

  Yaima Noa Oliva MARK SPAIN REAL ESTATE

  2076 Whispering Trails Blvd, Winter Haven, FL 33884
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  /8

  Est $309,829 Not Listed For Sale

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

  404 Chance Ave, Winter Haven, FL 33881

  404 Chance Ave, Winter Haven, FL 33881
• 

  

  /38

  $439,000

  • 3 Beds
  • 2 Baths
  • 2,603 Sq Ft

  2997 Plantation Rd, Winter Haven, FL 33884

  BEAUTIFULLY MAINTAINED, ONE OWNER POOL HOME IN DESIRABLE CYPRESSWOOD GOLF & COUNTRY CLUB PLANTATIONS!!! The Plantations is known for its charming setting, large lots, mature landscaping, friendly neighbors and peaceful streets to walk or bike ride! The entry into Cypresswood is manned with a 24hr security guard. You will want to call this property "home" the moment you arrive in the driveway

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  2997 Plantation Rd, Winter Haven, FL 33884
• 

  

  /3

  $3,400 per month

  • 5 Beds
  • 3 Baths
  • 2,845 Sq Ft
  • House for Rent

  740 Grove St, Winter Haven, FL 33881

  Nestled in the serene location of Winter Haven; beautiful house conveniently located near Lego Land. 5 bedrooms, 3 bathrooms, 2-car garage, stainless steel appliances. Fenced-in backyard offering space and privacy. Includes smart home technology so that you can connect to your home via smartphone. Enjoy Winter Haven's main attractions and sights such as boating on the Chain of Lakes and Antique

  Claudia Pulgarin Capital Nest Realty, LLC

  740 Grove St, Winter Haven, FL 33881
• 

  /2

  $699,000 Sold Jun 26, 2025

  • 2,764 Sq Ft
  • $253/SF
  • 57 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1970

  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
• 

  

  /26

  Est $322,000 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  408 Chance Ave, Winter Haven, FL 33881

  408 Chance Ave, Winter Haven, FL 33881
• 

  

  /25

  $224,900

  • 2 Beds
  • 2 Baths
  • 1,625 Sq Ft

  2243 Firestone Place Unit GP4, Winter Haven, FL 33884

  MAINTENANCE FREE SPACIOUS GOLF VILLA - END UNIT WITH 2 BEDROOMS & 2 BATHS, LOCATED IN THE GATED & MANNED GOLF COMMUNITY OF CYPRESSWOOD GOLF & COUNTRY CLUB!!! 18-hole golf course, Pro shop, pool, tennis, fishing, wellness center, clubhouse, restaurant, pub and activities for an active lifestyle! The open floor plan features living room open to dining and enclosed family room with access to the

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  2243 Firestone Place Unit GP4, Winter Haven, FL 33884
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  /24

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Condo for Rent

  1005 Eagle Pond Dr, Winter Haven, FL 33884

  MOVE-IN READY Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club available beginning 12/1/2023. This meticulously-maintained condo features hard floors throughout (no carpet!), new interior paint, NEW kitchen appliances, interior laundry (with brand new front load LG washer/dryer provided), and so much more. The spacious master bedroom features an

  Kayly Malinas JOHN WOOD REALTY, INC.

  1005 Eagle Pond Dr, Winter Haven, FL 33884
• 

  /2

  $182,500 Sold Jun 25, 2025

  • 1,017 Sq Ft
  • $179/SF
  • 51 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  703 Eagle Pond Dr Unit 7C, Winter Haven, FL 33884

  Immaculate GROUND Floor Eagle Pond Condo in Cypresswood Golf & Country Club. SELLER TO PROVIDE CREDIT TOWARD BUYER'S CLOSING COSTS - ASK FOR DETAILS!Don’t miss your chance to own this charming 2-bedroom, 2-bathroom ground-floor condo in the highly sought-after, gated Cypresswood Golf & Country Club community. Perfectly maintained, this move-in-ready home features an open-concept living

  Claudette Biaggi CENTURY 21 MYERS REALTY

  703 Eagle Pond Dr Unit 7C, Winter Haven, FL 33884
• 

  

  /17

  Est $306,593 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,546 Sq Ft

  4850 Hwy 550, Winter Haven, FL 33884

  4850 Hwy 550, Winter Haven, FL 33884
• 

  

  /39

  $280,000

  • 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 REALTY

  2817 Wingfoot Ct, Winter Haven, FL 33884
• 

  /2

  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • House for Rent

  3268 Country Walk Club Cir, Winter Haven, FL 33881

  Discover this charming 3-bedroom, 2-bath single-family home located in the desirable Country Walk community of Winter Haven. This property offers comfort, style, and a prime location. Its open-concept design features ceramic tile and carpet flooring, solid surface countertops, energy-efficient windows, and an inside laundry room. The primary suite includes a spacious walk-in closet and a private

  Arlenys Oviedo EXP REALTY LLC

  3268 Country Walk Club Cir, Winter Haven, FL 33881
• 

  

  /26

  $38,000 Sold Jun 20, 2025

  • 960 Sq Ft
  • $40/SF
  • 235 Days On Market

  • 2 Beds
  • 2 Baths

  340 Siberian Cypress Cir, Winter Haven, FL 33881

  MOTIVATED SELLERS! All reasonable offers considered. LOT RENT PAID THROUGH AUGUST! Perfect sized double wide manufactured home in the 55+ community of Cypress Creek Village. Built in 2019, the home is in great shape and offers a low LOT RENT of $600 and comes with the golf cart! The area is beautifully developed and with the multitude of things to do such as enjoying the Heated Pool,

  Hope Isaacs The SWANS Mobile Home ReSale Specialists LLC

  340 Siberian Cypress Cir, Winter Haven, FL 33881
• 

  

  /26

  Est $321,124 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  412 Chance Ave, Winter Haven, FL 33881

  412 Chance Ave, Winter Haven, FL 33881
• 

  

  /32

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  676 Augusta Rd, Winter Haven, FL 33884

  Welcome to 676 Augusta, a charming and well-maintained home nestled on a beautifully landscaped 0.18-acre lot with majestic oak trees and a serene backyard setting. The tiled entry foyer leads into a spacious living and dining area with updated carpeting, which opens seamlessly to an enclosed Florida room—perfect for relaxing or entertaining. The kitchen features stainless steel appliances, a

  Dee Norris NEXTHOME NORRIS & COMPANY REALTY

  676 Augusta Rd, Winter Haven, FL 33884
• 

  /2

  $470,000 Sold Jun 20, 2025

  • 2,552 Sq Ft
  • $184/SF
  • 23 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1994

  3158 Beauchamp Ct, Winter Haven, FL 33884

  NEW PRICE POINT!!! IMPECCABLY MAINTAINED COUNTRY CLUB RESIDENCE IN THE PLANTATIONS OF CYPRESSWOOD!! A beautiful home that is situated on a quiet cul-de-sac with lush landscaping and extensive curb appeal, with 4 bedrooms and 3 baths that offers an open concept with split bedrooms, volume ceilings, crown molding, and hickory scraped wood look tile throughout! The large eat-in kitchen features

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  3158 Beauchamp Ct, Winter Haven, FL 33884
• 

  

  /40

  Est $738,320 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,733 Sq Ft

  1834 Woodpointe Dr, Winter Haven, FL 33884

  1834 Woodpointe Dr, Winter Haven, FL 33884
• 

  

  /31

  $279,900

  • 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
• 

  /2

  $325,000 Sold Jun 16, 2025

  • 2,086 Sq Ft
  • $156/SF
  • 150 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  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
• 

  

  /45

  Est $265,437 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,435 Sq Ft

  732 Overlook Grove Dr, Winter Haven, FL 33884

  732 Overlook Grove Dr, Winter Haven, FL 33884
• 

  

  /26

  $200,000

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

  1606 Eagle Pond Dr, Winter Haven, FL 33884

  This is Eagle Pond, a beautiful section of the Cypress Woods Golf and Country Club. This secure, gated community offers around-the-clock security for added peace of mind. Situated on the second floor, this condo showcases impressive 10-foot ceilings and a spacious open layout. It features two bedrooms, walk-in closets, ceiling fans and the primary bedroom includes a private ensuite bath. The

  Juan Yglesias KELLER WILLIAMS REALTY SMART 1

  1606 Eagle Pond Dr, Winter Haven, FL 33884
• 

  /2

  $450,000 Sold Jun 13, 2025

  • 2,710 Sq Ft
  • $166/SF
  • 1 Day On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  2987 Plantation Rd, Winter Haven, FL 33884

  If you've been searching for the perfect home to raise a family, where every room feels just right and the neighborhood is full of charm, you have found it. This spacious, lovely 4-BEDROOM, 2.5 BATH home is located in the sought-after Cypresswood Golf & Country Club, a guard gated community known for its peaceful streets, friendly neighbors, and family-friendly lifestyle. As you pull up you are

  Tisha Talbot CENTURY 21 MYERS REALTY

  2987 Plantation Rd, Winter Haven, FL 33884
• 

  

  /26

  Est $318,510 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  752 Grove St, Winter Haven, FL 33881

  752 Grove St, Winter Haven, FL 33881
• 

  

  /39

  $190,977

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

  307 Eagle Pond Dr, Winter Haven, FL 33884

  Price update!!! This beautiful condo in the 24/7 guard-gated Cypresswood Golf & Country Club offers peaceful pond views you’ll love, visible from both bedrooms and the living room. With tall 10-foot ceilings and warm wood cabinets, the open living and dining area flows right into the breakfast bar kitchen, perfect for relaxing or hosting friends. Both bedrooms have roomy walk-in closets, plus

  Mabel Vassallo CENTURY 21 MYERS REALTY

  307 Eagle Pond Dr, Winter Haven, FL 33884
• 

  /2

  $278,000 Sold Jun 13, 2025

  • 1,367 Sq Ft
  • $203/SF
  • 23 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  628 Wexford Ct, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. 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

  Joy Desmond REMAX EXPERTS

  628 Wexford Ct, Winter Haven, FL 33884
• 

  

  /12

  Est $295,003 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft

  328 Inman Blvd, Winter Haven, FL 33881

  328 Inman Blvd, Winter Haven, FL 33881
• 

  

  /54

  $469,000

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

  1908 Crossroads Blvd, Winter Haven, FL 33881

  SELLER MOTIVATED! Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive,

  Jill Lingenfelter CENTURY 21 MYERS REALTY

  1908 Crossroads Blvd, Winter Haven, FL 33881
• 

  /2

  $270,000 Sold Jun 11, 2025

  • 2,237 Sq Ft
  • $121/SF
  • 90 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2006

  2320 Whispering Trails Place, Winter Haven, FL 33884

  $$PRICE REDUCTION! New Roof in 2023. 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

  Donald Toldson OLYMPUS EXECUTIVE REALTY INC

  2320 Whispering Trails Place, Winter Haven, FL 33884
• 

  

  /26

  Est $321,777 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  425 Chance Ave, Winter Haven, FL 33881

  425 Chance Ave, Winter Haven, FL 33881
• 

  

  /59

  $112,000

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

  203 Monterey Cypress Blvd Unit 174, Winter Haven, FL 33881

  **Charming Waterfront Retreat in Florida!** NEW ROOF 2025! Discover your dream home with this stunning 2008 Fleetwood model that boasts breathtaking views of a serene lake. Imagine sipping your morning coffee while watching Florida's vibrant birds from your cozy dining area or spacious living room. This meticulously maintained residence features an inviting vinyl-windowed Florida room, perfectly

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

  203 Monterey Cypress Blvd Unit 174, Winter Haven, FL 33881
• 

  /2

  $205,000 Sold Jun 11, 2025

  • 1,563 Sq Ft
  • $131/SF
  • 221 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  1086 Pelham Ct, Winter Haven, FL 33884

  Welcome to this stunning 2-bedroom, 2-bathroom villa located in the highly sought-after community of Cypresswood. The Villas on the Green are an ALL-AGES WELCOME and PET-FRIENDLY community. This home offers a perfect blend of modern updates and low-maintenance living. Step inside to discover gorgeous laminate flooring installed throughout the entire condo in 2020, giving the home a fresh,

  Minoo Brown LA ROSA REALTY PRESTIGE

  1086 Pelham Ct, Winter Haven, FL 33884
• 

  

  /49

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  376 Midnight Cypress Dr, Winter Haven, FL 33884

  376 Midnight Cypress Dr, Winter Haven, FL 33884
• 

  

  /30

  $199,500

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

  440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881

  Lot #97 / 3 B / 3 BA / 1,988 Sq. Ft. / $199,500.00 Spectacular Home! Completely Remodeled 2009 Erica Model in popular Cypress Creek Village! This large home is located on a spacious corner lot. It has a double carport with extra covered golf cart parking. Professionally remodeled upgrades include: - New Architectural Shingle Roof - New Air Conditioner and New Mr. Cool a/c for the tiled

  Jennifer Meyers CRF Communities

  440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881
• 

  /2

  $260,000 Sold May 29, 2025

  • 1,755 Sq Ft
  • $148/SF
  • 58 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  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

  Chris Loschiavo RE/MAX HERITAGE PROFESSIONALS

  602 Turnberry Ct, Winter Haven, FL 33884

Showing Results 81 - 120, Page 3 of 18