Cypresswood Homes

• 

  

  

  /12

  Est $295,590 Not Listed For Sale

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

  914 Cattleman St, Winter Haven, FL 33884

  914 Cattleman St, Winter Haven, FL 33884
• 

  

  

  /34

  $205,000

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

  2282 Firestone Place, Winter Haven, FL 33884

  Welcome to Cypresswood Golf & Country Club Living!Discover this charming 2-bed, 2-bath, single-story Golf Villa at 2282 Firestone Pl in the exclusive gated community of Cypresswood in Winter Haven, FL. Boasting 1,164 sq ft of thoughtfully designed living space, this villa offers the perfect blend of comfort, style, and sweeping golf course views.Key Features & Upgrades:Two inviting

  Juan Yglesias KELLER WILLIAMS REALTY SMART 1

  2282 Firestone Place, Winter Haven, FL 33884
• 

  

  

  /62

  $30,000 Sold May 27, 2025

  • 1,008 Sq Ft
  • $30/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 2006

  718 Red Cypress Ln, Winter Haven, FL 33881

  **Unleash Your Vision!** This 2-bedroom, 2-bathroom, 2006 Nobility manufactured home offers a fantastic opportunity to create your dream space. Featuring a desirable split floor plan, perfect for guest privacy, this home boasts 13' x 16' living room with carpeted flooring, a ceiling fan, and an entertainment center. The galley-style kitchen offers ample cabinet space, a pantry, and appliances

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

  718 Red Cypress Ln, Winter Haven, FL 33881
• 

  

  

  /11

  Est $335,054 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,853 Sq Ft

  700 Grove St, Winter Haven, FL 33884

  700 Grove St, Winter Haven, FL 33884
• 

  

  

  /73

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 2,001 Sq Ft

  10 Webb Rd, Winter Haven, FL 33881

  AUCTION!! 10am, Sat. Sept. 13th Secluded 4-Bedroom Ranch on 5 Acres with Pool, Barns & Country Charm! Discover the perfect blend of privacy, convenience, and space with this 4 bedroom, 2.5 bath ranch-style home nestled on 5 acres in East Winter Haven. Tucked away at the end of a quiet road, this former citrus grove offers a peaceful, no-HOA lifestyle with plenty of room for your family,

  Martin E Higgenbotham HIGGENBOTHAM AUCTIONEERS INTERNATIONAL LTD INC

  10 Webb Rd, Winter Haven, FL 33881
• 

  /2

  $240,000 Sold May 23, 2025

  • 1,660 Sq Ft
  • $145/SF
  • 43 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  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
• 

  

  /8

  Est $307,745 Not Listed For Sale

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

  949 Cattleman St, Winter Haven, FL 33881

  949 Cattleman St, Winter Haven, FL 33881
• 

  

  /36

  $450,000

  • Land
  • 4.36 Acres
  • $103,211 per Acre

  2230 Lake Daisy Rd, Winter Haven, FL 33884

  The property you are inquiring about is located in Winter Haven, FL in the Overlook Dr SE area of Polk County. This is 4.37 acres of improved land that has beautiful trees, pond with island, partially fenced, 2-story barn, covered RV parking space, septic system in place to accommodate an additional structure, well house to include pump, bladder tank and electrical panel, 400 Amp beneath ground

  Renee Butler BROKERS REALTY OF CENTRAL FLOR

  2230 Lake Daisy Rd, Winter Haven, FL 33884
• 

  /2

  $150,000 Sold May 21, 2025

  • 3,361 Sq Ft
  • $45/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1983

  3201 Cypresswood Blvd, Winter Haven, FL 33884

  Take advantage of this unique real estate offering in the heart of Winter Haven! This listing includes two parcels of land for a total of 2.94 acres, combining a 2.48-acre lot and an additional adjoining 0.46-acre parcel. The main lot features a previously existing home that was unfortunately damaged by fire, but the land itself is full of potential. Whether you're looking to build your dream

  Robert Johnson REAL BROKER, LLC

  3201 Cypresswood Blvd, Winter Haven, FL 33884
• 

  

  /29

  Est $382,253 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft

  911 Cattleman St, Winter Haven, FL 33881

  911 Cattleman St, Winter Haven, FL 33881
• 

  

  /23

  $229,900

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  4792 Summerfield Cir, Winter Haven, FL 33881

  DRASTIC PRICE REDUCTION! 3 Bedroom, 2 Bath Split bedroom plan in Country Club Estates. Luxury Plank Vinyl throughout. Concrete block stucco construction. Primary bedroom has a tray ceiling & Walk in closet. Large great room, Kitchen with an island. Interior laundry with washer & dryer included. Attached 2 car garage. Close to schools, shopping and restaurants.

  Ronald Gentile ORLANDO REO PROF I INC

  4792 Summerfield Cir, Winter Haven, FL 33881
• 

  /2

  $360,000 Sold May 20, 2025

  • 2,136 Sq Ft
  • $169/SF
  • 75 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  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
• 

  

  /11

  Est $295,676 Not Listed For Sale

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

  846 Turner Ln, Winter Haven, FL 33884

  846 Turner Ln, Winter Haven, FL 33884
• 

  

  /46

  $234,900

  • 2 Beds
  • 2 Baths
  • 1,563 Sq Ft

  1077 Medinah Way, Winter Haven, FL 33884

  HARD TO FIND ...YET EASY TO OWN.!!! ENJOY COMING HOME TO THIS WONDERFUL COMMUNITY IN A TENNIS VILLA. IT IS A SPACIOUS END UNIT IN THE BEAUTIFUL CYPRESSWOOD GOLF AND TENNIS COMMUNITY WITH LOTS OF AMENITIES INCLUDING GATE SECURITY. CALL TO PREVIEW THIS WELL-MAINTAINED 2 BED 2 BATH CB VILLA, WITH FORMAL LIVING AND DINING AREA, SPACIOUS FLORIDA ROOM OVERLOOKING THE TENNIS COURTS AND POOL AREA, NICE

  Heidi Gravel WESTLAKE REAL ESTATE CO., INC.

  1077 Medinah Way, Winter Haven, FL 33884
• 

  

  /34

  $310,000 Sold May 14, 2025

  • 2,200 Sq Ft
  • $141/SF
  • 137 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2005

  1802 Emily Dr, Winter Haven, FL 33884

  Discover your home in Winter Haven with this spacious 4-bedroom, 3-bathroom two-story. As you enter, you're welcomed by a charming formal dining room with convenient access to a well-equipped kitchen, complete with an island, two pantries, and a cozy nook area. The kitchen layout allows you to enjoy serene backyard views while at the sink. The main level also features a great family room, a full

  Johany Utrera AVID REALTY LLC

  1802 Emily Dr, Winter Haven, FL 33884
• 

  

  /11

  Not Listed For Sale

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

  942 Cattleman St, Winter Haven, FL 33884

  942 Cattleman St, Winter Haven, FL 33884
• 

  

  /46

  $264,900

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  13 Enclave Dr, Winter Haven, FL 33884

  Welcome to this maintained 3 bedroom, 2 bath one-story villa/townhouse located in Enclave, a quiet and desirable neighborhood within the gated golf community of Cypresswood Golf & Country Club. This spacious end-unit features a functional split-bedroom floor plan, generous living and dining areas, and an inviting Florida room that adds to the overall living space. The kitchen offers ample cabinet

  Suzanna Rudd KELLER WILLIAMS REALTY SMART 1

  13 Enclave Dr, Winter Haven, FL 33884
• 

  

  /34

  $177,000 Sold May 14, 2025

  • 1,422 Sq Ft
  • $124/SF
  • 175 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  2256 Firestone Place, Winter Haven, FL 33884

  SELLER MOTIVATED—Bring your Offer!! The unit requires TLC. It's a Great Flip, Income-Generating, or Primary Residence! Located in the desirable Cypresswood Golf & Country Club, this 2-bedroom, 2-bath end-unit villa is along the 8th fairway of the golf course, offering peaceful views, clubhouse amenities, and an attractive rental investment opportunity.The home itself features vaulted ceilings, a

  Kristen Costa LIVE FLORIDA REALTY

  2256 Firestone Place, Winter Haven, FL 33884
• 

  /2

  Est $309,252 Not Listed For Sale

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

  945 Cattleman St, Winter Haven, FL 33881

  945 Cattleman St, Winter Haven, FL 33881
• 

  

  /28

  $57,500

  • 1 Bed
  • 1 Bath
  • 648 Sq Ft

  4320 Dundee Rd Unit 61, Winter Haven, FL 33884

  Live Your Florida Dream You Deserve! Welcome to SOUTHERN DUCKS RV RESORT, an ACTIVE ADULT, PET-FRIENDLY community where you own your home and LEASE THE LAND in Winter Haven, Florida. MONTHLY LOT RENT is approximately $595, which includes WATER, SEWER, TRASH PICKUP, LAWN CARE, along with a wide range of amenities for you and your guests to enjoy. This 648 sq. ft, fully FURNISHED 1993

  Tammy Barnhart Renee's Resales

  4320 Dundee Rd Unit 61, Winter Haven, FL 33884
• 

  /2

  $256,000 Sold May 09, 2025

  • 1,758 Sq Ft
  • $146/SF
  • 19 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1977

  398 Troon Ct, Winter Haven, FL 33884

  Discover the perfect blend of comfort and convenience in this beautifully maintained 2-bedroom, 2-bath patio home nestled in the sought-after golf community of Cypresswood.. Boasting an inviting open floor plan, this home features a spacious living area with abundant natural light, well appointed kitchen and a cozy dining space. The primary suite offers a private retreat with an en-suite bath

  Sherry Hollingsworth RE/MAX HERITAGE PROFESSIONALS

  398 Troon Ct, Winter Haven, FL 33884
• 

  

  /11

  Est $345,214 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,109 Sq Ft

  703 Grove St, Winter Haven, FL 33884

  703 Grove St, Winter Haven, FL 33884
• 

  

  /51

  $152,500

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  268 Monterey Cypress Blvd, Winter Haven, FL 33884

  **Experience Florida Living at Its Finest!** Prepare to be captivated by this immaculate and elegant 2012 Nobility Maria, nestled in the highly sought-after Cypress Creek Village. This mostly furnished and freshly painted home boasts 1196 sq ft of beautifully designed living space, featuring 3 bedrooms, 2 bathrooms, and a delightful rear lanai leading to a bonus patio - all at an unbeatable

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

  268 Monterey Cypress Blvd, Winter Haven, FL 33884
• 

  /2

  $265,000 Sold May 08, 2025

  • 1,560 Sq Ft
  • $170/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2003

  208 Lake Region Blvd S, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to 208 Lake Region Blvd! Tucked away in the gated community of The Gates of Lake Region, this beautiful home offers the perfect blend of comfort, convenience and affordability (low HOA dues). From the moment you arrive, its charming brick accents and manicured landscaping create a warm and inviting first impression, hinting at the thoughtful

  Michael Stone THE STONES REAL ESTATE FIRM

  208 Lake Region Blvd S, Winter Haven, FL 33881
• 

  

  /11

  Est $312,092 Not Listed For Sale

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

  707 Grove St, Winter Haven, FL 33884

  707 Grove St, Winter Haven, FL 33884
• 

  

  /36

  $200,000

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

  1102 Eagle Pond Dr, Winter Haven, FL 33884

  Welcome to the Eagle Pond condominium in the Cypress Woods Golf and Country Club community. This coveted community is gated with 24-hour security guard. This bottom floor condo boasts 10-foot ceilings, open floor plan and two bedrooms with walk-in closets. The primary bedroom has an ensuite bathroom. The condo is newly painted with tile flooring in the Livingroom and kitchen. The bedrooms

  Robin McClendon CENTURY 21 MYERS REALTY LAKE WALES

  1102 Eagle Pond Dr, Winter Haven, FL 33884
• 

  /2

  $255,000 Sold May 07, 2025

  • Land
  • 0.79 Acre
  • $322,785 per Acre

  • 100 Days On Market

  0 Dundee Rd Unit MFRP4929882, Winter Haven, FL 33881

  Don't miss out on the opportunity to grab this vacant, commercial lot in a rapidly expanding area.!This lot is centrally located on Dundee Rd in Winter Haven with sever large new developments within 2 miles. The annual average daily traffic for this part of Dundee Rd is over 16,000 cars per day! making this a perfect location for most businesses. The owner already has drafted plans for a 5,000 sq

  Stetson Russell REAL FLORIDA REALTY LLC

  0 Dundee Rd Unit MFRP4929882, Winter Haven, FL 33881
• 

  

  /10

  Est $331,994 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,853 Sq Ft

  850 Turner Ln, Winter Haven, FL 33884

  850 Turner Ln, Winter Haven, FL 33884
• 

  

  /43

  $194,500

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

  1507 Eagle Pond Dr Unit 1507, Winter Haven, FL 33884

  Welcome to the Eagle Pond condominium in the Cypress Woods Golf and Country Club community. This coveted community is gated with 24-hour security guard. The condo boasts 10-foot ceilings, open floor plan and two bedrooms with walk-in closets. The primary bedroom has an ensuite bathroom. The condo is newly painted with updated flooring. There is a spacious storage closet on the exterior to

  Robin McClendon CENTURY 21 MYERS REALTY LAKE WALES

  1507 Eagle Pond Dr Unit 1507, Winter Haven, FL 33884
• 

  /2

  $290,000 Sold May 05, 2025

  • 2,140 Sq Ft
  • $136/SF
  • 149 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  645 Augusta Rd, Winter Haven, FL 33884

  New price reduction BELOW APPRAISED VALUE. The seller is willing to negotiate an interest rate buy-down. Discover this exceptionally charming 3-bedroom, 2-bathroom home nestled on the 10th fairway of Cypresswood Golf Course! From the paved driveway and walkway, enter through the foyer into a welcoming living room with dramatic vaulted ceilings, flowing into a spacious dining area. The large den

  Barbara Downs CENTURY 21 WATSON & MYERS REALTY

  645 Augusta Rd, Winter Haven, FL 33884
• 

  

  /8

  Est $320,437 Not Listed For Sale

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

  747 Grove St, Winter Haven, FL 33881

  747 Grove St, Winter Haven, FL 33881
• 

  

  /13

  $269,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  381 Troon Ct, Winter Haven, FL 33884

  Updated and beautifully maintained 2bd/2bath plus Bonus Room. Definitely one of the loveliest houses in Cypresswood. Golf and Country Club located on the 11th tee. The home offers exceptional views of the Fairway. Mature Landscaping and circular paved driveway. Welcome your buyer to this beautiful, maintained home. Large Living Room and adjacent dining room offers ample room for furnishings. The

  Barbara Downs CENTURY 21 WATSON & MYERS REALTY

  381 Troon Ct, Winter Haven, FL 33884
• 

  /2

  $499,900 Sold May 01, 2025

  • 2,335 Sq Ft
  • $214/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  3001 Plantation Rd, Winter Haven, FL 33884

  Discover the perfect blend of comfort and luxury in this beautifully maintained 3 bedroom 2 bathroom pool home nestled within the sought after Cypresswood Golf and Country Club community with a 24-hour guarded entrance gate, 18-hole championship golf course, Jr. Olympic sized swimming pool, tennis/pickle-ball, and clubhouse with a Pro-shop and restaurant. Designed for both relaxation and

  Kimberly Dinkel RE/MAX HERITAGE PROFESSIONALS

  3001 Plantation Rd, Winter Haven, FL 33884
• 

  

  /26

  Est $314,142 Not Listed For Sale

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

  937 Cattleman St, Winter Haven, FL 33881

  937 Cattleman St, Winter Haven, FL 33881
• 

  

  /42

  $157,500

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

  244 Siberian Cypress Cir Unit 345, Winter Haven, FL 33881

  STUNNING DESIGN • High-End Finishes • BUILT IN 2019 • NEW ROOF in 2024 Welcome to CYPRESS CREEK VILLAGE, one of the newest 55+ Active Adult communities...and PETS are welcome! Homes in CYPRESS CREEK VILLAGE, a 55+ PET-FRIENDLY community in Winter Haven, Florida, are on lot LEASED LAND. Owning the home, but not the land, you pay a monthly LOT RENT of $684 which gives you and your guest

  Tammy Barnhart Renee's Resales

  244 Siberian Cypress Cir Unit 345, Winter Haven, FL 33881
• 

  /2

  $370,000 Sold Apr 28, 2025

  • 2,002 Sq Ft
  • $185/SF
  • 36 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  762 Canberra Rd, Winter Haven, FL 33884

  THIS OUTSTANDING AND WELL MAINTAINED 2,002 SF 3 BR/2.5 BA POOL HOME IS LOCATED ON A CUL-DE-SAC OVERLOOKING THE GOLF COURSE IN THE WELL ESTABLISHED GATED COMMUNITY OF CYPRESSWOOD IN WINTER HAVEN, FLORIDA. As you step inside you will note views of the golf course ...from the living room, dining room, kitchen, primary bedroom, Florida/bonus room and the screened-in pool. The home was designed with a

  Carol Sheil JUDY B CLEAVES PROPERTIES INC

  762 Canberra Rd, Winter Haven, FL 33884
• 

  

  /29

  Est $380,370 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft

  919 Cattleman St, Winter Haven, FL 33881

  919 Cattleman St, Winter Haven, FL 33881
• 

  

  /33

  $94,900

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

  305 Midnight Cypress Dr Unit 2, Winter Haven, FL 33881

  Amazing Opportunity - FULLY FURNISHED Florida Dream Home! Homes in CYPRESS CREEK VILLAGE, a 55+ PET-FRIENDLY community in Winter Haven, Florida, are on lot LEASED LAND. Owning the home, but not the land, you pay a monthly LOT RENT of $657 which gives you and your guest access to the amenities of the community. Step into this SPACIOUS and beautifully maintained 3-BEDROOM, 2-bathroom 2005

  Tammy Barnhart Renee's Resales

  305 Midnight Cypress Dr Unit 2, Winter Haven, FL 33881
• 

  /2

  $270,000 Sold Apr 25, 2025

  • 1,533 Sq Ft
  • $176/SF
  • 35 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2016

  3272 Whispering Trails Ave, Winter Haven, FL 33884

  Fresh and Modern 2018 Home is awaiting its’ new owner. Step inside this IMMACULATLY MAINTAINED Open Floor plan home that'sAiry and Inviting with Hight Celling and crown molding throughout, NO CARPET, 3 Bedrooms, 2 Baths. Master Suite offers a tranquilescape with ensuite bathroom. Split Floor plan gives guests and other's privacy with Guest Bathroom and Plenty of Storage. Kitchenhas upgraded

  Troy Udit ENGEL & VOLKERS ORLANDO DR PHILLIPS

  3272 Whispering Trails Ave, Winter Haven, FL 33884
• 

  

  /29

  Est $377,578 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft

  915 Cattleman St, Winter Haven, FL 33881

  915 Cattleman St, Winter Haven, FL 33881

Showing Results 121 - 160, Page 4 of 18