Cypresswood Homes for Sale

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  /42

  $619,000

  • 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
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  /24

  $200,000

  • 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
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  /30

  $184,900

  • 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 Florida

  Jennifer Meyers CRF Communities

  440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881
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  /17

  $229,000

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

  374 Troon Ct, Winter Haven, FL 33884

  BRAND NEW ROOF 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 front courtyard wall.The

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  374 Troon Ct, Winter Haven, FL 33884
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  /19

  $279,900

  • 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. This beautiful Central Florida 4 BDR/2BA home is in pristine condition and truly move-in ready! Located in the desirable Overlook Ridge community in Winter Haven, you’ll enjoy convenient access to Highway 27 with easy commutes to Lake Wales and north to I-4. Perfectly positioned near everything that makes Central Florida special — golf courses,

  Team Papin FLORIDA LUXURY REALTY INC

  780 Overlook Grove Dr, Winter Haven, FL 33884
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  /46

  $469,990

  • 4 Beds
  • 3 Baths
  • 2,697 Sq Ft

  2512 Sherwood St, Winter Haven, FL 33881

  A beautiful family home is now available in the desirable gated community of Crossroads at Lake Region. This 4-bedroom, 3-bath property feels like new. The welcoming covered entry features 8-foot glass doors with sidelights that fill the space with natural light and open into the foyer, great room, and kitchen area with impressive 13' ceilings. The well-designed 3-way split floor plan offers

  Brian Cox KELLER WILLIAMS REALTY SMART 1

  2512 Sherwood St, Winter Haven, FL 33881
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  /15

  $250,000

  • Land
  • 0.79 Acre
  • $316,456 per Acre

  0 Dundee Rd Unit P4924283, Winter Haven, FL 33881

  Just Reduced! Stop by and check on this vacant lot in an area that is growing with new expanded roads. More than 3/4-acre zone C3 lot on Dundee Rd Hwy 542 with approx. 143 feet of road frontage. Ideally positioned in front of the 16th St intersection. The Department of Transportation finished up the Dundee Rd expansion improvements further to the East. This project has given this lot multiple

  Michael Brenner CENTURY 21 MYERS REALTY

  0 Dundee Rd Unit P4924283, Winter Haven, FL 33881
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  /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 LIFESTYLE INTERNATIONAL REALTY

  2893 Whispering Trails Dr, Winter Haven, FL 33884
• 

  

  /98

  $799,900

  • 4 Beds
  • 3 Baths
  • 2,397 Sq Ft

  3050 Crump Rd, Winter Haven, FL 33881

  ** This home can be purchased with no income verification needed!** Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor

  Lisa Matheny ENGEL & VOELKERS LAKELAND

  3050 Crump Rd, Winter Haven, FL 33881
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  /42

  $370,000

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft

  652 Grove St, Winter Haven, FL 33884

  Welcome to 652 Grove St, a versatile and spacious 'Freedom' model home in the heart of Winter Haven! This unique property has a main residence featuring 3 bedrooms, 2 bathrooms, a dedicated office space, and a private laundry room. The open-concept layout includes a 2-car garage and plenty of natural light throughout. What sets this home apart is the fully independent Annex/Guest House. This

  Lizandra Troisi Passos MY REALTY GROUP, LLC.

  652 Grove St, Winter Haven, FL 33884
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  /50

  $393,000

  • 3 Beds
  • 2 Baths
  • 1,947 Sq Ft

  260 Greenfield Rd, Winter Haven, FL 33884

  Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed

  Kayly Malinas JOHN WOOD REALTY, INC.

  260 Greenfield Rd, Winter Haven, FL 33884
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  /35

  $59,900

  • 1 Bed
  • 1 Bath

  4320 Dundee Rd Unit 36, Winter Haven, FL 33884

  This IMMACULATE - 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 convenience, tastefully

  Linda Wilson Sunset Home Sales

  4320 Dundee Rd Unit 36, Winter Haven, FL 33884
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  /53

  $400,000

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

  126 Lake Region Cir, Winter Haven, FL 33881

  ALMOST PARADISE! 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

  Carol Sheil JUDY B CLEAVES PROPERTIES INC

  126 Lake Region Cir, Winter Haven, FL 33881
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  /62

  $749,900 New Construction

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

  4030 Palma Ceia Cir, Winter Haven, FL 33884

  Luxury New Construction in Cypresswoods! MAJOR PRICE REDUCTION! 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

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  4030 Palma Ceia Cir, Winter Haven, FL 33884
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  /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
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  /46

  $198,000

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

  683 Broadmoor Cir, Winter Haven, FL 33884

  NEW, NEW, NEW...this villa has recently been renovated. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. This beautiful home is located directly on golf course frontage and has newer metal roof. You will be living in a community with a manned guard gate and your villa is only a short walk to the clubhouse, restaurant, and pool. Don't miss out on this one,

  Darlene Bice BHHS FLORIDA PROPERTIES GROUP

  683 Broadmoor Cir, Winter Haven, FL 33884
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  /51

  $75,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  707 Red Cypress Ln, Winter Haven, FL 33881

  2006 home in Cypress Creek Village, a premier 55+ community, will allow 40+! Super cute home with split bedroom plan with 2 large bedrooms, 2 baths, and a den! Spacious and open floor plan with an open-concept living area. Fully furnished with laminate flooring in the main areas, all window treatments remain. LIVING ROOM 17' 6 X 15' 9 Welcome to your new home! Spacious, Bright, and Open to the

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

  707 Red Cypress Ln, Winter Haven, FL 33881
• 

  

  /43

  $379,950

  • 2 Beds
  • 2 Baths
  • 2,523 Sq Ft

  241 Greenfield Rd, Winter Haven, FL 33884

  Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot on the 13th green. This charming 2-bedroom, 2-bathroom residence features a bright and open layout with a large living area plus an additional family room accented by a cozy brick fireplace and floor-to-ceiling wood built-ins. The brand-new kitchen has

  Angie Reynolds PORCHLIGHT HOMES LLC

  241 Greenfield Rd, Winter Haven, FL 33884
• 

  

  /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
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  /53

  $439,000

  • 4 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  108 Lake Region Blvd N, Winter Haven, FL 33881

  Gated custom home in the Gates of Lake Region! This quiet and highly-desirable neighborhood has the look, feel and privacy of an age-restricted community, but it is open to all ages. This property was constructed as a builder’s model home so it offers numerous upgrades and architectural details that can be found throughout. Located within the quaint, gated community of The Gates of Lake Region

  Michael Stone THE STONES REAL ESTATE FIRM

  108 Lake Region Blvd N, Winter Haven, FL 33881
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  /2

  $150,000

  • Land
  • 0.32 Acre
  • $468,750 per Acre

  1776 Lake Hill Dr, Winter Haven, FL 33884

  Large residential lot that will accommodate a variety of floor plans. Builder and building plans must be approved by Owner.

  John Wood, JR JOHN WOOD REALTY, INC.

  1776 Lake Hill Dr, Winter Haven, FL 33884
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  /25

  $184,900

  • 2 Beds
  • 2 Baths
  • 1,410 Sq Ft

  2274 Firestone Place, Winter Haven, FL 33884

  ON THE GOLF COURSE. GORGEOUS VIEWS AND SUNSETS!Well maintained 2 bed / 2 bath golf villa overlooks the 8th fairway and features split bedrooms, large living /dining combo, enclosed lanai with heat and air, partially covered courtyard, rear patio and carport parking space.

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  2274 Firestone Place, Winter Haven, FL 33884
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  /50

  $229,900

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft

  459 Pinehurst Ct, Winter Haven, FL 33884

  Welcome to this beautifully maintained patio home located in a desirable gated golf community, offering comfort, convenience, and exceptional value. Nestled on a quiet dead-end street, this charming residence features 2 bedrooms, 2 bathrooms, and a spacious 2-car garage. Property Highlights2 Bedrooms | 2 Bathrooms2-Car GarageNew Roof (2024)New Gutters (2025)New Hot Water

  Debbie Bradbury REAL ESTATE BROKERS USA, INC.

  459 Pinehurst Ct, Winter Haven, FL 33884
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  /16

  $348,000 New Construction

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

  643 Grove St, Winter Haven, FL 33881

  Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quarz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and en-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!

  Martha Leighton MIHOUSE REALTY LLC

  643 Grove St, Winter Haven, FL 33881
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  /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
• 

  

  /21

  $281,300

  • 4 Beds
  • 2 Baths
  • 1,782 Sq Ft

  4872 Summerfield Cir, Winter Haven, FL 33881

  Charm and curb appeal abound for this Winter Haven Home! Step inside into the inviting foyer, which is flanked on the right by the three secondary bedrooms. Through the well-appointed living room you'll find the kitchen, which boasts stainless steel appliances, hard surface countertops, and ample storage. Rounding out this ranch style floorplan is the dining room and the primary suite. Come and

  Blake Keathley EVERYSTATE INC.

  4872 Summerfield Cir, Winter Haven, FL 33881
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  /33

  $240,000

  • 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
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  /63

  $174,900

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

  416 Siberian Cypress Cir, Winter Haven, FL 33881

  Step into this beautifully maintained home in the sought-after 55+ gated community of Cypress Creek Village in Southeast Winter Haven. The open-concept kitchen, dining, and living areas are bright and airy, perfect for everyday living and entertaining. The kitchen features stainless steel appliances, a farmhouse sink overlooking the carport, and a center island with ample storage and seating. The

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

  416 Siberian Cypress Cir, Winter Haven, FL 33881
• 

  

  /30

  $334,900

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  416 Sandestin Dr, Winter Haven, FL 33884

  UPSCALE HOME IN CYPRESSWOOD GOLF COMMUNITY. REDUCED! Beautifully remodeled and ready for the discerning buyer. Large 3 BR/2BA patio home located in beautiful Cypresswood Golf Community. This home features updated gourmet kitchen, remodeled baths, newer roof, whole house Generac generator with new 10 year warranty, natural gas instant hot water heater, new refrigerator 2022, new gas range, new

  Sharon Watson CENTURY 21 WATSON & MYERS REALTY

  416 Sandestin Dr, Winter Haven, FL 33884
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  /61

  $260,000

  • 2 Beds
  • 2 Baths
  • 1,444 Sq Ft

  47 Enclave Dr, Winter Haven, FL 33884

  Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale, FULLY FURNISHED, and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, New Furniture,

  David Shippey XCELLENCE REALTY, INC

  47 Enclave Dr, Winter Haven, FL 33884
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  /34

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft

  2036 Whispering Trails Blvd, Winter Haven, FL 33884

  Charming 3-bedroom, 2-bath home located in a desirable HOA community in Winter Haven! This well-maintained residence offers 1,148 square feet of comfortable living space with a functional layout designed for everyday living. Enjoy the convenience of an interior laundry area and a spacious living room that flows into the dining and kitchen areas. The primary suite features a private bathroom,

  Marisela Quintero LA ROSA REALTY PRESTIGE

  2036 Whispering Trails Blvd, Winter Haven, FL 33884
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  /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
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  /70

  $199,000

  • 3 Beds
  • 3 Baths
  • 1,716 Sq Ft

  352 Siberian Cypress Cir, Winter Haven, FL 33881

  STOP and TAKE A LOOK INSIDE! LOW LOT FEE $604/month, 55 Plus Active Lifestyle Community in Cypress Creek Village. 3 bedroom/3 bath home. The beautiful double wide home is spacious, has a Water Filtration System, is sold with all appliances, MOVE IN READY, Central Air, Storage Shed, Sunroom, Ceiling Fans, Walk In Closet, Ensuite Bathroom, Tray Ceiling, Removable Electric Fireplace, Gutters, Newer

  Daniel Butler Sun Realty of Florida

  352 Siberian Cypress Cir, Winter Haven, FL 33881
• 

  

  /23

  $129,900

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

  1201 Cypress Vine Rd, Winter Haven, FL 33881

  CYPRESS CREEK VILLAGE #297 - 2BED / 2 BATH / 1,200 SF. / $129,900 POND VIEW HOME with Double Driveway! 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 split floor plan

  Jennifer Meyers CRF Communities

  1201 Cypress Vine Rd, Winter Haven, FL 33881
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  /58

  $187,900

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

  1012 Medinah Dr, Winter Haven, FL 33884

  Fresh new price — NOW OFFERING A HOME WARRANTY! Your opportunity to own in Cypresswood just got better! 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, creating a

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  1012 Medinah Dr, Winter Haven, FL 33884
• 

  

  /32

  $374,900

  • 5 Beds
  • 3 Baths
  • 2,696 Sq Ft

  204 Inman Blvd, Winter Haven, FL 33881

  Relocating to Florida? This pristine 5-bedroom, 3-bath home offers nearly 2,700 square feet of thoughtfully designed living space in the heart of Central Florida, providing the space, flexibility, and value many buyers from northern states and high-cost markets are seeking.Priced at $379,000—approximately $140 per square foot—this home delivers exceptional value compared to similar properties

  Veronica Bard LA ROSA REALTY PRESTIGE

  204 Inman Blvd, Winter Haven, FL 33881

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