Winter Haven, FL Homes for Sale with Pool

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  $224,900

  • 3 Beds
  • 2.5 Baths
  • 1,407 Sq Ft

  301 Orange Blossom Dr, Winter Haven, FL 33880

  WATERFRONT! ON THE CANAL TO THE CHAIN OF LAKES!! Renovated, updated & remodeled. This townhouse is low-maintenance and offers a tranquil setting right in the middle of town, great location! Features include a neutral color scheme, renovated kitchen with plenty of cabinet space and a convenient pass-through bar leading to an open living room and dining area, primary bedroom with ensuite and

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  301 Orange Blossom Dr, Winter Haven, FL 33880
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  $34,900

  • 2 Beds
  • 2 Baths
  • 896 Sq Ft

  62 Dale Dr, Winter Haven, FL 33880

  Whether you're looking to downsize, retire, or simply embrace the best of Florida's lifestyle, this 2 bedroom|2 bathroom in Winter Haven is the perfect place to make your dreams a reality. Winter Haven MHC is a 55+ pet-friendly community for active seniors. There is plenty of additional living space to entertain family/friends and/or enjoy the Florida weather in the large air conditioned lanai,

  Patti Alvin Sunset Home Sales

  62 Dale Dr, Winter Haven, FL 33880
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  /32

  $119,000

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft

  333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880

  Welcome to 333 Lake Howard Drive, where comfort, convenience, and a vibrant 55+ lifestyle come together in the heart of Winter Haven’s charming lakefront community. Nestled within the desirable Imperial Harbours 55+ community, this spacious and sunlit 3-bedroom, 2-bathroom corner-unit condo that oversees the pool offers the ideal space for those seeking a relaxed, maintenance-free lifestyle. From

  Jason Prieto LPT REALTY, LLC

  333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880
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  /27

  $284,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  4952 Kaia Ave, Winter Haven, FL 33884

  The property is located at 4952 Kaia Avenue WINTER HAVEN FL 33884 priced at 284990, the square foot and stories are 1665, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4952 Kaia Ave, Winter Haven, FL 33884
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  $350,900 New Construction

  • 4 - 5 Beds
  • 3.5 Baths
  • 2,587 Sq Ft

  Wesley II Plan at VillaMar, Winter Haven, FL 33884

  Welcome home to the Wesley II by Highland Homes, a two-story Florida home that lives large with an open living area on the first story and a flexible second-story layout! Downstairs, enjoy a fully open living area with: A large gathering room. An open kitchen with a counter-height buttery island or optional galley island, a walk-in pantry, and a sunny dining cafe. A convenient powder room. An

  Highland Homes Builder

  521 Vittorio Dr Unit 37316138, Winter Haven, FL 33884
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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
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  /39

  $270,000

  • 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 REAL

  2817 Wingfoot Ct, Winter Haven, FL 33884
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  /51

  $39,900

  • 2 Beds
  • 1.5 Baths
  • 672 Sq Ft

  866 Century Dr, Winter Haven, FL 33881

  You don't want to miss this lovely 2-bedroom/1.5-bath home in Hidden Golf Club, a 55+ community conveniently located on Lake Henry in Central Florida! This home comes partially furnished and has many of the extra features Florida living offers, not to mention, it is located in one of the few parks that still have fair monthly lot rent rates. The current lot rent for this home is $588. The home

  Patti Alvin Sunset Home Sales

  866 Century Dr, Winter Haven, FL 33881
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  /18

  $175,000

  • 3 Beds
  • 2 Baths
  • 1,073 Sq Ft

  523 Winter Terrace Unit 523, Winter Haven, FL 33881

  Welcome to this cozy 3-bedroom, 2-bath corner unit condo located in the lakefront community Winter Ridge on Lake Smart. Enjoy added privacy and convenience with two assigned parking spaces and a generously sized enclosed Florida Room—complete with a window unit for extra living space year-round.Inside, you’ll find tile flooring and carpet, and a split floorplan. Outside, take advantage of

  Pat Hancock THOMAS LYNNE REALTY GROUP LLC

  523 Winter Terrace Unit 523, Winter Haven, FL 33881
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  /32

  $119,000

  • 2 Beds
  • 2 Baths
  • 1,179 Sq Ft

  1264 Las Brisas Ln Unit 361, Winter Haven, FL 33881

  1264 Las Brisas Lane - Lot 361 2 Bedrooms | 2 Bathrooms | 1,179 Sq. Ft. | $119,000 Immaculate Home with Incredible Pond & Golf Course Views Welcome to this beautifully maintained, fully furnished Florida retreat located in the desirable Four Lakes community. Immaculate inside and out, this move-in-ready home offers drywall throughout, elegant crown molding, charming wainscoting, and easy-care

  Cheryl Dobbs CRF Communities

  1264 Las Brisas Ln Unit 361, Winter Haven, FL 33881
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  /21

  $115,000

  • 2 Beds
  • 2 Baths
  • 1,347 Sq Ft

  1776 6th St NW Unit 303, Winter Haven, FL 33881

  Improved Price!! All new window in the building...Price improvement...Seller ready to sell! Beautifully maintained 55+ condominium located in Lake Ridge Winter Haven. This is a gated community offering a tranquil living space. Conveniently located near hospitals, restaurants, shopping, entertainment and so much more. This home offers everything you need to live a true Floridian lifestyle.

  Brenda Brooks CENTURY 21 MYERS REALTY

  1776 6th St NW Unit 303, Winter Haven, FL 33881
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  /31

  $59,900

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

  763 Century Ln, Winter Haven, FL 33881

  NEW PRICE! 2/2 home has open floor plan. Large eat-in kitchen has lots of cabinet space and opens into the dining room with built-in China cabinet. Appliances stay including the washer and dryer. Master bedroom has ensuite bathroom with a walk-in shower and added counter and storage space. Home comes furnished. Updated windows, Golf cart garage with negotiable golf cart has space for a workshop

  Leslie Yokshas Flamingo Mobile Home Sales

  763 Century Ln, Winter Haven, FL 33881
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  /26

  $69,500

  • 2 Beds
  • 2 Baths

  218 Green Meadow Dr, Winter Haven, FL 33884

  If you are looking for the perfect retirement home that is fully furnished, this is the one for you. Located in gated Orange Manor West, a very popular 55+ community located in Southeast Winter Haven. This home is on leased land with a monthly fee of $513, which includes cable, internet and trash pickup. Park Lane Mobile Home 2 bedroom/2 bath with approximately 1,152 sf , king sized master

  Emily Muscarella

  218 Green Meadow Dr, Winter Haven, FL 33884
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  /35

  $43,900

  • 2 Beds
  • 2 Baths

  696 Century Ln, Winter Haven, FL 33881

  Enjoy the Florida lifestyle in this this beautifully maintained furnished home with spacious open layout and split floor plan. Home located in highly sought after 55+Community.Golf cart is included in sale! Spacious lanai with newer windows for relaxing. Outdoor concrete patio perfect for grilling and gas grill included! Home is completely turn-key! Home Highlights -Newer AC (2024) -Newer Vapor

  Brandi Sappington CRF Communities

  696 Century Ln, Winter Haven, FL 33881
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  $167,000

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft

  6613 Westchester Dr NE, Winter Haven, FL 33881

  Welcome home to this beautifully updated 2-bedroom, 2-bath residence located in a well-loved 55+, no pet community on sparkling Lake Henry in sunny Winter Haven. Built in 1987 and offering 1,274 square feet, this furnished home has been thoughtfully improved and is truly move-in ready. The updated kitchen and bathrooms feature new cabinetry along with granite and marble countertops, while the

  Laura Villardi COLDWELL BANKER REALTY

  6613 Westchester Dr NE, Winter Haven, FL 33881
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  /40

  $150,000

  • 3 Beds
  • 2 Baths
  • 1,830 Sq Ft

  1727 Glen Abby Ln Unit 802, Winter Haven, FL 33881

  3 Bedroom | 2 Bath | 1,830 Sq Ft | $150,000 Exceptional Corner Lot Home with Split-Bedroom Floor Plan Located on a highly desirable corner lot, this impressive 3-bedroom turn key home features an extra-large decorator driveway and outstanding curb appeal. This spacious 3-bedroom, 2-bath residence offers a desirable split-bedroom floor plan and 1,830 square feet of comfortable, well-designed

  Cheryl Dobbs CRF Communities

  1727 Glen Abby Ln Unit 802, Winter Haven, FL 33881
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  /42

  $165,000

  • 2 Beds
  • 2 Baths
  • 1,525 Sq Ft

  6518 Raintree Ln NE, Winter Haven, FL 33881

  Welcome to this beautifully maintained 2-bedroom, 2-bathroom manufactured home with an office in the desirable 55+ community of Brookhaven Village, where you OWN your land! Situated on a large lot with no rear neighbors, this property offers an incredible sense of privacy and tranquility.From the moment you enter, you’ll notice the care and updates that have gone into this home over the

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  6518 Raintree Ln NE, Winter Haven, FL 33881
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  /8

  $288,500

  • 3 Beds
  • 2 Baths

  3829 Giorgio Dr, Winter Haven, FL 33884

  PROPERTY IS ALMOST BRAND NEW, SO NOTHING NEEDS TO BE DONE, NO REPAIRS!TAKE ADVANTAGE OF THIS GREAT PROPERTY, IN EXCELLENT LOCATION.

  Ivette Loaiza First Pro International Rlty

  3829 Giorgio Dr, Winter Haven, FL 33884
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  /34

  $45,900

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  378 Alpine Dr Unit 378, Winter Haven, FL 33881

  Swiss Village / Lot #378 / 2 Bedroom/2 Bath / 1,320 Sq. Ft. / $45,900.00 PRICE REDUCED TO AN ALL TIME LOW on this gorgeous home, in this much sought after community, with great curb appeal and popular floor plan. This home offers: Freshly Painted Walls, Luxury Vinyl Plank Flooring, Additional Square Footage in Florida Room, Roof Over Roof, Energy efficient French Doors, Irrigation, Screen Around

  Jennifer Torres CRF Communities

  378 Alpine Dr Unit 378, Winter Haven, FL 33881
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  /44

  $109,900

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft

  700 Mirror Terrace NW Unit 303, Winter Haven, FL 33881

  Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second

  Kevin Tison LPT REALTY, LLC

  700 Mirror Terrace NW Unit 303, Winter Haven, FL 33881
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  /32

  $118,000

  • 2 Beds
  • 2 Baths
  • 1,438 Sq Ft

  1255 Las Brisas Ln Unit 415, Winter Haven, FL 33881

  2 Bedroom | 2 Bath | 1,438 Sq Ft |Price Reduced from$121,000 to $118,000! Welcome to your dream home in the heart of Four Lakes Golf Club! This one-of-a-kind property is designed for comfort - perfect for those looking to embrace the next chapter of life. Just walking up to the house, it already feels unique and inviting. As you enter the home, on your left, you will find the guest bedroom,

  Cheryl Dobbs CRF Communities

  1255 Las Brisas Ln Unit 415, Winter Haven, FL 33881
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  /20

  $29,000

  • 2 Beds
  • 2 Baths
  • 975 Sq Ft

  187 Valencia Dr SE, Winter Haven, FL 33884

  Incredible Opportunity! Fixer-Upper with Unlimited Potential & Unmatched Charm! Homes in Orange Manor East, a 55+ pet friendly community are on lot leased land in Winter Haven, Florida. Owning the home, but not the land, you pay a monthly lot rent of $536 which gives you and your guest access to the amenities of the community. Trash also included in the lot fee. Located in Orange Manor East,

  Bette Johnson Renee's Resales

  187 Valencia Dr SE, Winter Haven, FL 33884
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  /6

  $266,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  Denali Plan at VillaMar - Classic Series, Winter Haven, FL 33884

  Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076780, Winter Haven, FL 33884
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  /12

  $293,180 New Construction

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

  3857 Giorgio Dr, Winter Haven, FL 33884

  Open floor plan creates a unified living space with a large great room that overlooks the kitchen.

  Meritage Homes Builder

  3857 Giorgio Dr, Winter Haven, FL 33884
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  $330,000

  • 5 Beds
  • 3 Baths
  • 2,616 Sq Ft

  2005 Carnostie Rd, Winter Haven, FL 33884

  Short Sale. Welcome home to this inviting 5-bedroom, 3-bath family home offering 2,601 sq. ft. of comfortable living on an oversized lot in the sought-after VillaMar community! ? This move-in ready home is priced to sell fast, and the seller is motivated; don’t wait on this one! Step inside and enjoy the spacious, open-concept layout designed with families in mind. The main floor features a

  Sharonda Lawrence ASCENSION REALTY INTERNATIONAL

  2005 Carnostie Rd, Winter Haven, FL 33884
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  /3

  $389,990 New Construction

  • 4 - 5 Beds
  • 3 Baths
  • 2,500 Sq Ft

  Winston Plan at Willowbrook North, Winter Haven, FL 33881

  The Winston floorplan offers a spacious two-story layout with four bedrooms and three full bathrooms. This well-designed home includes a two-car garage and features a functional flex room on the main level, ideal for a home office or extra living space. The first floor includes a cozy great room adjacent to the cafe and covered patio, creating an inviting space for relaxation and entertaining.

  Dream Finders Homes Builder

  0 Fl-544 St Unit 37521594, Winter Haven, FL 33881
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  /25

  $445,000

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  1151 Carefree Cove Dr, Winter Haven, FL 33881

  This beautiful 3-bedroom, 2-bath lakefront home sits on Winter Haven’s northern Chain of Lakes on Lake Conine and has received a first-class renovation including a brand new roof, 4-ton A/C, luxury vinyl plank flooring, and new water heater all installed in 2025. The interior living area includes new fixtures, new front and rear sliding glass doors, and new paint throughout. The kitchen features

  Jonathan Minerick HOMECOIN.COM

  1151 Carefree Cove Dr, Winter Haven, FL 33881
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  /33

  $260,000

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

  2809 Wingfoot Ct, Winter Haven, FL 33884

  GOLF COURSE HOME! WELCOME TO THIS AWESOME GOLF VILLA WITH A FAIRWAY VIEW OF THE 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

  Patricia France HAPPY DAYS REALTY LLC

  2809 Wingfoot Ct, Winter Haven, FL 33884
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  /77

  $421,900

  • 4 Beds
  • 3 Baths
  • 1,927 Sq Ft

  4016 Carteret Dr, Winter Haven, FL 33884

  Welcome to 4016 Carteret Drive — a refined 4-bedroom, 3-bathroom lakefront sanctuary located in the incredible 55+ Traditions Community of Winter Haven. Perfectly positioned on one of the largest lots in the neighborhood and offering sweeping views of Ruby Lake, this exceptional residence blends luxury, comfort, and thoughtful upgrades throughout. From the moment you arrive, you'll appreciate the

  Drew Wilson AMPLIFY REAL ESTATE SERVICES FL

  4016 Carteret Dr, Winter Haven, FL 33884
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  /27

  $333,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,029 Sq Ft

  Shelby II Plan at VillaMar, Winter Haven, FL 33884

  Welcome home to the Shelby II by Highland Homes! This sunny, spacious, open-layout home features large bedrooms, a beautifully designed kitchen, and desirable outdoor living space! The Shelby II features: A sunny kitchen with a large counter-height island, walk-in pantry, and adjacent dining cafe. 4 bedrooms standard, with options for 3 bedrooms plus an open or French-door enclosed den. A

  Highland Homes Builder

  521 Vittorio Dr Unit 39326886, Winter Haven, FL 33884
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  /42

  $292,000

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

  4202 San Rocco Way, Winter Haven, FL 33884

  NEW PRICE! Move-in Ready. This one-story, 4-bedroom, 2-bath home offers 1,851 square feet of well-designed living space and is situated on an oversized corner lot in the VillaMar community. Recent upgrades include a fully vinyl-fenced backyard and a whole-home water filtration system with water softener, providing added comfort and peace of mind.Built in 2023, this Cali floorplan features

  Jennifer NG CANVAS REAL ESTATE

  4202 San Rocco Way, Winter Haven, FL 33884
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  /34

  $350,990 New Construction

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

  HAYDEN Plan at Harmony at Lake Eloise, Winter Haven, FL 33880

  Find all the space you need in our popular two-story Hayden floorplan in Harmony at Lake Eloise, one of our communities in Winter Haven, Florida. Inside this 5-bedroom, 3-bathroom home, you’ll find 2,601 square feet of flexible living space and a two-car garage. Step thru the front foyer and you're greeted with a flex room designed for work or play. Make your way to the kitchen on the first

  D.R. Horton Builder

  1651 Hummingbird Rd Unit 36202783, Winter Haven, FL 33880
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  /27

  $315,740 New Construction

  • 4 Beds
  • 2 Baths
  • 1,498 Sq Ft

  2779 Adeline Ave, Winter Haven, FL 33881

  The property is located at 2779 Adeline Ave WINTER HAVEN FL 33881 priced at 315740, the square foot and stories are 1498, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  2779 Adeline Ave, Winter Haven, FL 33881
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  /31

  $249,900

  • 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
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  Price To Be Determined New Construction

  • 3 Beds
  • 2 Baths
  • 1,970 Sq Ft

  Plan 1970 at VillaMar - Villamar, Winter Haven, FL 33884

  Adams Homes Builder

  836 Vienna Dr Unit 36449687, Winter Haven, FL 33884
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  /28

  $380,000

  • 4 Beds
  • 2 Baths
  • 1,619 Sq Ft

  1731 Avenue C NE, Winter Haven, FL 33881

  Exclusive property in Winter Haven featuring a 4-bedroom main home, private pool, independent studio, and parking for up to 6 cars. Located in a peaceful and welcoming city known for its beautiful lakes and excellent quality of life, this property offers comfort, space, and great potential. The main house includes 4 spacious bedrooms, 2 beautifully updated bathrooms, a fully renovated kitchen

  Paola Millan LA ROSA REALTY LLC

  1731 Avenue C NE, Winter Haven, FL 33881
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  /69

  $98,500

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

  948 Heartwood Cypress Dr, Winter Haven, FL 33881

  This well-maintained 2014 Nobility Lindsay, owned and occupied part-time by its original owner, is perfectly priced and move-in ready. Located in beautiful Cypress Creek Village, a premier 55+ community, this 3-bedroom, 2-bath home offers an affordable and comfortable Florida lifestyle - and it comes fully furnished. The spacious living room (16'6" x 18'2") features an open layout with

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

  948 Heartwood Cypress Dr, Winter Haven, FL 33881
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  /12

  $80,000

  • 3 Beds
  • 2 Baths
  • 1,330 Sq Ft

  333 Lake Howard Dr NW Unit 204C, Winter Haven, FL 33880

  Short Sale. Step into one of the largest units at the vibrant 55+ community of Imperial Harbor in Winter Haven! This spacious 3-bedroom, 2-bath condo also features a bonus room. With three comfortable bedrooms, there’s ample space for guests, a home office, or crafting area. Enjoy an active lifestyle with shuffleboard courts, a well-equipped gym, and a billiard room. The heated pool ensures

  Anthony Giglio REALTY COOPERATIVE

  333 Lake Howard Dr NW Unit 204C, Winter Haven, FL 33880
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  /18

  $299,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,874 Sq Ft

  Columbus Plan at VillaMar, Winter Haven, FL 33884

  This expansive two-story home boasts a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient

  Lennar Builder

  6614 Crescent Loop Unit 38667745, Winter Haven, FL 33884
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  /6

  $323,950 New Construction

  • 4 Beds
  • 3 Baths
  • 2,051 Sq Ft

  Tarragon Plan at Annabelle Estates, Lake Wales, FL 33859

  Richmond American Homes Builder

  4130 Old Bartow Lake Wales Rd Unit 37316200, Lake Wales, FL 33859

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