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Winter Haven, FL Homes for Sale with Pool

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  • /44

    $99,900

    $25K PRICE DROP
    • 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
  • /20

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,697 Sq Ft

    1109 Brimstone Cir, Winter Haven, FL 33884

    LOCATION, LOCATION, LOCATION! Best Deal in Harmony on Lake Eloise!!! The Seller has upgraded everything with custom finishes throughout! The seller will also assist with buyer's closing cost. The open, light and bright floor plan is perfect for entertaining with a welcoming kitchen that is the heart of the home & features a solid-surface island large enough to seat six guests. Stainless

    Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    1109 Brimstone Cir, Winter Haven, FL 33884
  • /20

    $29,000

    $11K PRICE DROP
    • 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
  • /6

    $255,999

    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
  • /25

    $267,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft

    5560 Taverna Loop, Winter Haven, FL 33884

    The property is located at 5560 Taverna Loop WINTER HAVEN FL 33884 priced at 267900, the square foot and stories are 1302, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

    D.R. Horton Builder
    5560 Taverna Loop, Winter Haven, FL 33884
  • /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
  • /25

    $425,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,734 Sq Ft

    1151 Carefree Cove Dr, Winter Haven, FL 33881

    Looking for a peaceful lakefront pool home or well appointed AibBnB property? This beautiful 3-bedroom, 2-bath home sits on Lake Connie in Winter Haven’s northern Chain of Lakes and has been completely renovated to include a brand new roof, 4-ton A/C, luxury vinyl plank flooring, interior / exterior paint, and new water heater all installed in 2025. The interior living area includes new fixtures,

    Jonathan Minerick HOMECOIN.COM

    1151 Carefree Cove Dr, Winter Haven, FL 33881
  • /59

    $69,900

    $9K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,380 Sq Ft

    196 Fairway Cir, Winter Haven, FL 33881

    2 Bed | 2 Bath | 1380 square foot | $69,900 (Swiss Golf and Tennis- Lot 196) Price Drop! Located in highly sought after 55+ community! Location, Location! This gorgeous fully furnished, move-in-ready home offers a bright and open layout on a prime lot in the community. Enjoy peace of mind with updated interior and thoughtful custom touches throughout. Highlights include- New Appliances - Roof 2

    Brandi Sappington CRF Communities

    196 Fairway Cir, Winter Haven, FL 33881
  • /67

    $1,195,000

    • 5 Beds
    • 5.5 Baths
    • 3,235 Sq Ft

    250 Brigham Rd NW, Winter Haven, FL 33881

    Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end

    David Small KELLER WILLIAMS REALTY SMART 1

    250 Brigham Rd NW, Winter Haven, FL 33881
  • /74

    $124,900

    • 2 Beds
    • 2 Baths
    • 1,403 Sq Ft

    4158 Rolling Oaks Dr, Winter Haven, FL 33880

    Walk right in to this fully furnished home located in Oakwood Estates, a 55+ community. The kitchen is laid out perfect for entertaining and contains a large pantry for storage. The living area is open and spacious with cathedral ceilings to make it feel even more open. The area currently used for a dining area could also be used as a family room or second living area. The primary bedroom can

    Kathy Devor COLDWELL BANKER REALTY

    4158 Rolling Oaks Dr, Winter Haven, FL 33880
  • /29

    $243,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,464 Sq Ft

    4715 Tony St, Lake Wales, FL 33859

    The property is located at 4715 Tony Street LAKE WALES FL 33859 priced at 243990, the square foot and stories are 1464, 2.The number of bath is 2, halfbath is 1 there are 3 bedrooms and 1 garages. For more details please, call or email.

    D.R. Horton Builder
    4715 Tony St, Lake Wales, FL 33859
  • /27

    $287,900

    New Construction $7K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,498 Sq Ft

    2791 Adeline Ave, Winter Haven, FL 33881

    The property is located at 2791 Adeline Ave WINTER HAVEN FL 33881 priced at 287900, 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
    2791 Adeline Ave, Winter Haven, FL 33881
  • /64

    $279,000

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,693 Sq Ft

    1303 Stately Oaks Dr NW, Winter Haven, FL 33881

    Welcome to this beautifully refreshed 3-bedroom, 2-bath pool home in Winter Haven with NO HOA! Situated on a spacious lot in the established Stately Oaks community, this move-in ready property offers comfort, flexibility, and the Florida lifestyle buyers are looking for. Inside, you’ll find bright updated living spaces with fresh finishes, abundant natural light, and a functional layout designed

    Chelsey Palmowski CENTURY 21 MYERS REALTY

    1303 Stately Oaks Dr NW, Winter Haven, FL 33881
  • /12

    $388,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,387 Sq Ft

    3964 Giorgio Dr, Winter Haven, FL 33884

    Open first floor creates a unified living space with a large great room that overlooks the kitchen and dining area. Upstairs loft can be used to best fit your needs and tech area is perfect for a home office.

    Meritage Homes Builder
    3964 Giorgio Dr, Winter Haven, FL 33884
  • /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
  • /78

    $589,000

    Open Sat 10AM - 12:30PM
    • 3 Beds
    • 2 Baths
    • 2,526 Sq Ft

    6209 Pinehurst Loop, Winter Haven, FL 33884

    Modern Elegance! 6209 Pinehurst Loop Winter Haven, Florida 33884. Built in 2021, this custom designed home is located in Lake Ashton, one of Central Florida's Premier 55 Plus community. Perfectly positioned on a quiet street this exceptional home with Northwest exposure offers effortless luxury with modern upgrades. Offering excellent curb appeal with a well manicured lawn and mature landscape

    Lori Raath LAKE ASHTON REALTY INC.

    6209 Pinehurst Loop, Winter Haven, FL 33884
  • /49

    $43,500

    • 2 Beds
    • 1.5 Baths
    • 784 Sq Ft

    882 Century Dr Unit 882, Winter Haven, FL 33881

    2 Bed | 1 1/2 Bath | 784 square foot | $43,500 (Hidden Golf Club- Lot 882) Enjoy the Florida lifestyle in this highly sought after 55+ community. This beautifully maintained home is on a nice corner lot. Home Highlights - Indoor laundry, Roof (2023), AC (2021), New Windows (2024) Dishwasher, stove and fridge all within the past 2 years, updated high toilets (2025) and much more! You will love the

    Brandi Sappington CRF Communities

    882 Century Dr Unit 882, Winter Haven, FL 33881
  • /31

    $229,900

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,368 Sq Ft

    14 Enclave Dr, Winter Haven, FL 33884

    This meticulously maintained and professionally updated 2 bedroom 2 bath villa is 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 and dryer, screened

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    14 Enclave Dr, Winter Haven, FL 33884
  • /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
  • /57

    $120,000

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    4242 Cedarwood St, Winter Haven, FL 33880

    Pack your bags and move right into this fully furnished home. You won't find any carpet in this well maintained home with new vinyl plank flooring in the living room, dining room, and kitchen. The refrigerator, dishwasher, and washer and dryer have been updated in the last few years. Sit on the bright and inviting front porch with your morning coffee. Oakwood Estates, a 55+ community offers many

    Kathy Devor COLDWELL BANKER REALTY

    4242 Cedarwood St, Winter Haven, FL 33880
  • /10

    $309,100

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft

    3924 Giorgio Dr, Winter Haven, FL 33884

    Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet.

    Meritage Homes Builder
    3924 Giorgio Dr, Winter Haven, FL 33884
  • /61

    $429,500

    • 4 Beds
    • 3.5 Baths
    • 2,766 Sq Ft

    139 Woden Way, Winter Haven, FL 33884

    DONT MISS THIS RARE LAKEVIEW OPPORTUNITY IN DESIRABLE VALHALLA GATED COMMUNITY. THIS 2 STORY TOWNHOME OFFERS OVER 2700 LIVING AREA WITH STUNNING VIEWS OF LAKE ELOISE. THIS HOME FEATURES4BR/3.5BA WHICH INCLUDES A DOWNSTAIRS PRIMARY SUITE AND A SECONDARY UPSTARS PRIMARY. THIS CUSTOM JOHN TOUCHTON BUILT HOME BOASTS OF STUNNING QUALITIES THROUGHOUT.THE KITCHEN HAS PORCELAIN TILE FLOORING,

    Glenda Pruitt FLORIDA HOME CHOICE REALTY

    139 Woden Way, Winter Haven, FL 33884
  • /37

    $349,500

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    1558 Drexel Ave NE, Winter Haven, FL 33881

    Virtually Staged. HUGE PRICE DROP! Completely renovated Gene Leedy home and move-in ready, this beautifully updated home combines modern style with everyday comfort in the heart of Central Florida. Step inside to a bright, open floor plan filled with natural light from large floor-to-ceiling windows throughout—including in the bedrooms. The spacious living areas flow seamlessly, creating a warm

    David Small KELLER WILLIAMS REALTY SMART 1

    1558 Drexel Ave NE, Winter Haven, FL 33881
  • /13

    $365,000

    • 4 Beds
    • 2 Baths
    • 2,460 Sq Ft

    302 Sterling Dr, Winter Haven, FL 33884

    Short Sale. Located in Winter Haven, this 4-bedroom, 2-bath home offers approximately 2,460 square feet of living space with a two-car garage, spacious layout, and private pool. The home's generous floor plan provides multiple living areas and ample space for everyday living, entertaining, or accommodating a variety of household needs. Based on available information and photographs, the property

    Jonathon, PA McLeod KELLER WILLIAMS ELITE REALTY

    302 Sterling Dr, Winter Haven, FL 33884
  • /71

    $290,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,887 Sq Ft

    142 Morning Glory Cir, Winter Haven, FL 33884

    You will be impressed the moment you walk through the door! It’s so clean, polished and move-in ready! This home is a beautifully maintained 3-bedroom, 2-bath home located in the desirable Morningside neighborhood within the gated Winterset community. This thoughtfully designed split-bedroom floor plan offers both comfort and functionality, featuring a formal living room, formal dining room, and

    Karen Myers CENTURY 21 MYERS REALTY

    142 Morning Glory Cir, Winter Haven, FL 33884
  • /19

    $219,990

    New Construction $4K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,386 Sq Ft

    3013 Captain Jax Way, Winter Haven, FL 33884

    This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor.

    Lennar Builder
    3013 Captain Jax Way, Winter Haven, FL 33884
  • /18

    $277,490

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

    Columbus Plan at Villa Mar, 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
  • /21

    $105,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,252 Sq Ft

    404 Country Ln NE Unit 404, Winter Haven, FL 33881

    Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary

    Casandra Vann KELLER WILLIAMS REALTY SMART

    404 Country Ln NE Unit 404, Winter Haven, FL 33881
  • /32

    $119,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,697 Sq Ft

    1806 Belfry Ln Unit 539, Winter Haven, FL 33881

    2 Bedroom | 2 Bath | 1,697 Sq Ft | $119,000 Four Lakes Golf Club Lot 539 From the moment you arrive, this home captures your attention with its impeccable landscaping and charming front sitting area-the perfect place to relax and enjoy the Florida lifestyle. Beautifully maintained inside and out, this fully furnished, turnkey home is packed with thoughtful upgrades and inviting spaces. Step

    Cheryl Dobbs CRF Communities

    1806 Belfry Ln Unit 539, Winter Haven, FL 33881
  • /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
  • /28

    $215,000

    $5K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,312 Sq Ft

    2330 SE Royal Isle, Winter Haven, FL 33880

    Beautifully updated 2 bed, 2 1/2 bath townhome in the desirable Park Lake Community. Enjoy a modern kitchen (2023) plus a new A/C, renovated master bathroom with a relaxing soaking tub (2024). Located in a quiet neighborhood just minutes from downtown, shopping, restaurants, hotels and only 10 minutes to Legoland. Right next to the Advent Sports Complex. Great location with recent upgrades, bring

    Janet Lynn LPT REALTY, LLC

    2330 SE Royal Isle, Winter Haven, FL 33880
  • /12

    $334,950

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,679 Sq Ft

    Tourmaline Plan at Annabelle Estates, Lake Wales, FL 33859

    The two-story Tourmaline plan greets guests with a charming covered entry. On the main floor, you’ll find a private study and convenient powder room that can be optioned as an additional bedroom and bathroom. A spacious great room, a dining nook and a well-appointed kitchen featuring an island and center-meet doors leading onto a relaxing patio are also included. Upstairs, discover a laundry, a

    Richmond American Homes Builder
    4130 Old Bartow Lake Wales Rd Unit 36431505, Lake Wales, FL 33859
  • /50

    $219,900

    $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,045 Sq Ft

    23 Casarena Ct, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of Winter Haven's Chain of Lakes. This spacious 2BR/2.5BA townhome that offers approximately 2,045 sq ft of living space featuring vaulted ceilings, abundant natural light & a functional two-story layout. The main level

    Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

    23 Casarena Ct, Winter Haven, FL 33881
  • /2

    $334,999

    New Construction $14K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,226 Sq Ft

    5381 San Pietro Dr, Winter Haven, FL 33884

    Welcome to The Azure, where modern design meets practical living in a home that has it all. With 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home is crafted for comfort and style. The extraordinary elevation and professionally designed landscaping create a captivating first impression. Step through the front door to discover luxurious vinyl plank flooring that extends throughout the

    Casa Fresca Homes Builder
    5381 San Pietro Dr, Winter Haven, FL 33884
  • /18

    $349,521

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,077 Sq Ft

    5347 Mickey Ave, Winter Haven, FL 33884

    This home offers, 9"4' ceilings and 8' doors, 42' cabinets, white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home, all bedrooms, family room, and covered lanai are prewired for ceiling fans, secondary bedroom with its own bathroom. Special financing rates and closing cost assistance may be available. Options may vary by community and offers are

    Stephanie Morales AXEN REALTY, LLC

    5347 Mickey Ave, Winter Haven, FL 33884
  • /35

    $79,900

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

    209 Fairway Cir, Winter Haven, FL 33881

    2 Bed | 2 Bath | 1248 square foot | $79,900 (Swiss Golf and Tennis- Lot 209) 14K Price Drop- Don't miss this one! Beautifully updated home featuring a new A/C (2026) and roof (2019), with updated electrical and plumbing throughout. Interior upgrades include all-new flooring, new appliances, and fresh paint, creating a bright, move-in-ready space. Additional highlights include a new tankless water

    Brandi Sappington CRF Communities

    209 Fairway Cir, Winter Haven, FL 33881
  • /50

    $189,900

    • 2 Beds
    • 2 Baths
    • 930 Sq Ft

    7902 Waterview Way Unit 7902, Winter Haven, FL 33884

    Welcome to 7902 Waterview Way, a beautifully maintained low-maintenance condo nestled within a desirable gated community. Offering a perfect blend of comfort and convenience, this home features tasteful upgrades, modern finishes, and a functional layout designed for easy everyday living. Enjoy a carefree lifestyle with exterior maintenance taken care of while taking advantage of the community's

    Kimberly Cabrera LA ROSA REALTY PRESTIGE

    7902 Waterview Way Unit 7902, Winter Haven, FL 33884
  • /39

    $355,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 2,110 Sq Ft

    Poinciana Plan at Willowbrook North, Winter Haven, FL 33881

    The Poinciana floorplan offers a well-designed, one-story layout that includes 4 bedrooms and 2 bathrooms, complete with a spacious two-car garage. This home is centered around a sizable great room, which seamlessly connects to the open kitchen and cozy cafe area, making it ideal for family gatherings and entertaining. The owner's suite, located at the back for added privacy, includes a walk-in

    Dream Finders Homes Builder
    0 Fl-544 St Unit 37521595, Winter Haven, FL 33881
  • /28

    $188,500

    $1K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    6450 Hollyberry Ln NE, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Welcome to 6450 Hollyberry Lane in Brookhaven Village—a highly sought-after 55+ community where you own your land, making this a rare opportunity! This beautifully updated, move-in ready home features new luxury vinyl flooring (2025) and a bright, open layout perfect for everyday living and entertaining. The upgraded kitchen offers butcher block

    David Small KELLER WILLIAMS REALTY SMART 1

    6450 Hollyberry Ln NE, Winter Haven, FL 33881

Showing Results 241 - 280, Page 7 of 18

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