Winter Haven, FL Homes for Sale with Pool

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  /80

  $354,000

  • 3 Beds
  • 2 Baths
  • 2,045 Sq Ft

  1819 Sandhill Ln, Winter Haven, FL 33884

  Welcome to Cypresswood Golf & Country Club, a gated and guard-gated community offering resort-style living in a beautiful golf course setting. This well-maintained 3-bedroom, 2-bathroom home is ideally situated at the end of a quiet cul-de-sac, providing one of the most desirable locations on the street. Inside, you'll find a spacious open-concept floor plan designed for comfortable living and

  Lori Roberts GOLD HEART REALTY LLC

  1819 Sandhill Ln, Winter Haven, FL 33884
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  /48

  $145,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  447 Village Cir SW, Winter Haven, FL 33880

  This home is a must see!! Very well maintained home located in Village Park, a 55+ community where dogs are allowed. The home features new thermal efficient windows and all new plumbing. The vapor barrier is also new. The kitchen is very open and functional. The living room is comfortable and inviting. The primary bath has a new vanity and the bedroom carpet is new. Plus, the laundry is located

  Kathy Devor COLDWELL BANKER REALTY

  447 Village Cir SW, Winter Haven, FL 33880
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  /30

  $285,900

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft

  1518 Fuji Ct, Winter Haven, FL 33881

  Discover resort-style living in this charming 3-bedroom, 2-bath home built in 2023, nestled in the amenity-rich Villages at BridgeWater community. Boasting 1,537 sq ft of modern comfort on a 5,998 sq ft lot, enjoy an open floor plan with vaulted ceilings, a modern kitchen with large island, and a private primary suite. Community perks include a pool, fitness center, tennis courts, and a

  John Crusinberry MARK SPAIN REAL ESTATE

  1518 Fuji Ct, Winter Haven, FL 33881
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  /16

  $239,990

  New Construction $4K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,423 Sq Ft

  3060 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 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

  3060 Captain Jax Way, Winter Haven, FL 33884
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  /78

  $125,000

  • 2 Beds
  • 2.5 Baths
  • 1,184 Sq Ft

  2500 21st St NW Unit 50, Winter Haven, FL 33881

  Priced to Sell — Bring Your Vision (and Your Toolbelt) Opportunity is knocking at 2500 21st St NW, #50 in Winter Haven, and it’s asking for someone ready to turn sweat into serious equity. This lake view property is priced well below its true value for the location and community the kind of deal that rewards buyers who see potential where others see a to-do list. Location is everything here:

  Jason Prieto LPT REALTY, LLC

  2500 21st St NW Unit 50, Winter Haven, FL 33881
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  /16

  $360,000

  $30K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,806 Sq Ft

  1501 7th St SE, Winter Haven, FL 33880

  Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven. Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT,2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shakercabinets, quartz countertops and stainless steel appliances. The bathrooms have been fully renovated as well and feature

  Laura Auten ELEVATE REALTY LLC

  1501 7th St SE, Winter Haven, FL 33880
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  /32

  $98,800

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  502 Leyland Cypress Way Unit 61, Winter Haven, FL 33881

  CYPRESS CREEK VILLAGE #61 / 2 BED / 2 BATH / 1,344 SF / $98,800 POND VIEW HOME with Double Driveway! This Large WELL MAINTAINED updated home is partially furnished and move-in-ready for you! This 2006 Nobility Home features an open floor plan and large two-level lanai overlooking a pond! Lanai includes tile floors, vinyl windows, roman shades, and a covered patio that is perfect for grilling out!

  Jennifer Meyers CRF Communities

  502 Leyland Cypress Way Unit 61, Winter Haven, FL 33881
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  /50

  $71,500

  • 2 Beds
  • 2 Baths

  739 Red Cypress Ln, Winter Haven, FL 33881

  Discover the perfect blend of relaxation, recreation, and carefree Florida living in this beautifully updated 2-bedroom, 2-bath home located in the highly sought-after gated 55+ community of Cypress Creek Village! Ideally situated in Central Florida, you'll enjoy easy access to scenic lakes, botanical gardens, parks, museums, shopping, dining, and world-famous attractions. Whether you're seeking

  Linda Wilson Sunset Home Sales

  739 Red Cypress Ln, Winter Haven, FL 33881
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  /43

  $98,900

  $11K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  1511 Aberdeen Ln Unit 198, Winter Haven, FL 33881

  This Immaculate 1260 sq ft home features two bedrooms and two full baths, with a lanai under central AC, a screened-in sunroom overlooking the 9th tee of an outstanding 18-hole Championship Golf Course in Four Lakes Golf Club 55+ Community in Central Florida. The master suite features a large walk-in closet and an en suite bath with a walk-in shower. The second bedroom is across from a full bath

  Deb Bartholomew Sunset Home Sales

  1511 Aberdeen Ln Unit 198, Winter Haven, FL 33881
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  /86

  $750,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  7 Lake Arrowhead Dr, Winter Haven, FL 33880

  EXECUTIVE POOL HOME SITUATED ON 2.39 ACRES HORSE FARM. 4 BEDROOMS, 3 BATHS, including 2 barns. Well built and maintained barn with 4 stalls, tack room and hay and feed room. Additional barn with two overhead doors for tractors and equipment as well as workshop. Both barns have metal roofs.Seller currently has a horse and donkey on the property. Property is beautifully landscaped with an

  Sharon Watson CENTURY 21 WATSON & MYERS REALTY

  7 Lake Arrowhead Dr, Winter Haven, FL 33880
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  $465,990

  New Construction $3K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,787 Sq Ft

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

  Harmony at Lake Eloise presents The Camden, available to build in Winter Haven, FL. This all-concrete block constructed, one-story multi-gen layout offers two homes under one roof. As you enter the foyer you are greeted with two guest bedrooms that share an en suite bathroom with a double vanity. Making your way down the hall you will find a large dining room perfect for the whole family. The

  D.R. Horton Builder

  1651 Hummingbird Rd Unit 39009648, Winter Haven, FL 33880
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  /2

  $333,375

  New Construction

  • 4 Beds
  • 2 Baths
  • 2,005 Sq Ft

  525 Vittorio Dr, Winter Haven, FL 33884

  Brand-new 4-bedroom home for sale in Winter Haven, Florida! This beautiful home features a sunny, open living area with luxury vinyl plank flooring and volume ceilings, opening to outdoor living space on a large covered lanai. Relax in your spacious owner's suite with an elegant tray ceiling, two walk-in wardrobes, and a large en-suite bath with dual vanities, a decorative tiled shower with glass

  Highland Homes Builder

  525 Vittorio Dr, Winter Haven, FL 33884
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  /18

  Price To Be Determined

  New Construction

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

  Aria Plan at Annabelle Estates, Lake Wales, FL 33859

  The Aria is one of our one-story floorplans featured in Annabelle Estates in Winter Haven, Florida. With multiple exteriors to choose from, the Aria is a popular home. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,672 square feet of comfortable living. This all-concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area,

  D.R. Horton Builder

  4019 Penelope Ave Unit 36202722, Lake Wales, FL 33859
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  /28

  $148,900

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

  1221 Cypress Vine Rd Unit 256, Winter Haven, FL 33884

  Lot #256 - 2 Bed /2 Bath + Den /1,568 Sq. Ft./$148,900.00 Spectacular Pond Views from this 2016 Ashley Model in beautiful Cypress Creek Village! This spacious home is located on a waterfront lot with breathtaking views! It offers a double carport with an additional golf cart path! This gorgeous home offers: *Vaulted Ceilings *Kitchen with coffee station and pantry *French doors into large den

  Jennifer Meyers CRF Communities

  1221 Cypress Vine Rd Unit 256, Winter Haven, FL 33884
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  Price To Be Determined

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,415 Sq Ft

  Plan 1415 at Villamar, Winter Haven, FL 33884

  Adams Homes Builder

  836 Vienna Dr Unit 36466636, Winter Haven, FL 33884
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  /4

  $89,900

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  333 Lake Howard Dr NW Unit 302D, Winter Haven, FL 33880

  Virtually Staged. Welcome to maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. This 3rd floor 2-bedroom, 2-full-bath condo offers the relaxed lifestyle many buyers look for, complete with elevator access for easy entry. You are greeted by views of the community pool and cabana area right from your front entrance, while the interior features a bright Florida Room

  Natalie Elson REGAL REAL ESTATE LLC

  333 Lake Howard Dr NW Unit 302D, Winter Haven, FL 33880
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  /33

  $259,900

  $10K PRICE DROP

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

  29 Enclave Dr, Winter Haven, FL 33884

  New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit has just undergone a professional interior paint job. Enjoy Easterly pasture and sunrise views from the lanai. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  29 Enclave Dr, Winter Haven, FL 33884
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  Price To Be Determined

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  Plan 1820 at Villamar, Winter Haven, FL 33884

  Adams Homes Builder

  836 Vienna Dr Unit 36445791, Winter Haven, FL 33884
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  $289,990

  New Construction

  • 5 Beds
  • 2 Baths
  • 1,708 Sq Ft

  DUNDEE Plan at Willowbrook South, Winter Haven, FL 33881

  Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Willowbrook South in Winter Haven, Florida. Choose between three thoughtfully designed exterior styles. This spacious 5-bedroom, 2-bathroom home offers 1,708 square feet of modern, comfortable living. Step inside to an inviting open-concept layout where the kitchen, living, and dining areas flow

  D.R. Horton Builder

  2815 Adeline Ave Unit 38507577, Winter Haven, FL 33881
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  /86

  $482,000

  • 4 Beds
  • 3 Baths
  • 2,550 Sq Ft

  1814 Sandhill Ln, Winter Haven, FL 33884

  Here is your opportunity to own an immaculate home in the sought after community of Cypresswood Golf and Country Club. Consistently voted the Number 1 Golf Course in the area. This vibrant community has it all. Aside from the fantastic course right out your door, enjoy everything else it has to offer. A wonderful restaurant and Club House where they host live music 3 nights a week and top notch

  Stacy Tuttle REMAX EXPERTS

  1814 Sandhill Ln, Winter Haven, FL 33884
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  /19

  $90,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  4165 Rolling Oaks Dr, Winter Haven, FL 33880

  Priced to sell, Home has a new metal roof, CHA is approximately five years old, and you will feel right at home from the moment you walk in. Come enjoy the beautiful Florida sunsets in this 55+ gated, five-star park.

  Rita Stead SOUTHERN BELLE REALTY

  4165 Rolling Oaks Dr, Winter Haven, FL 33880
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  /24

  $150,000

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

  622 Ridge Terrace, Winter Haven, FL 33881

  Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite

  Diana Acosta TRUE FLORIDA REALTY LLC

  622 Ridge Terrace, Winter Haven, FL 33881
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  /89

  $89,000

  $6K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  325 Lakeview Ln SE, Winter Haven, FL 33884

  ** Exclusive Listing! Age 55+ Land Lease Community with monthly lot rent. Contact listing agent below for ALL showings and offers.** You'll soon have your very own slice of Florida paradise as the new owner of this super spacious and exceptionally well maintained 1985 Fuqua. Priced right at $89,000, and measuring 25x52, plus the 10x25 Florida room, this home will provide approximately 1550 total

  Shawna Kemp Mobile Home Spot Inc.

  325 Lakeview Ln SE, Winter Haven, FL 33884
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  /40

  $56,900

  • 2 Beds
  • 2 Baths
  • 784 Sq Ft

  715 Century Ln Unit 715, Winter Haven, FL 33881

  2 Bed | 2 Bath | 784 square foot | $56,900 (Hidden Golf Club- Lot 715) Located in highly sought after 55+ community! This well-maintained furnished home offers a bright, open layout. Highlights include- No rear neighbors! All new windows, AC (5 years), Inside laundry, spacious lanai. Home also has large carport with golf cart parking in rear. Enjoy the beautifully maintained 18-hole golf course.

  Brandi Sappington CRF Communities

  715 Century Ln Unit 715, Winter Haven, FL 33881
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  /56

  $215,000

  • 3 Beds
  • 2.5 Baths
  • 1,549 Sq Ft

  2216 Starboard, Winter Haven, FL 33881

  Check out this wonderful opportunity to own a spacious 3-bedroom, 2.5-bath home in the desirable 55+ community of Hartridge Landings! This well-maintained community offers a low HOA fee that includes access to the community pool and a private boat ramp on Lake Hartridge, providing access to Winter Haven's renowned Chain of Lakes. Step inside to an open and versatile floor plan featuring two

  Bree Allison KELLER WILLIAMS TAMPA CENTRAL

  2216 Starboard, Winter Haven, FL 33881
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  /22

  $139,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,077 Sq Ft

  689 Lake Howard Dr NW Unit 2D, Winter Haven, FL 33880

  Price Improvement!! Welcome to this Charming 2-bedroom 2 bath move-in-ready condo in the well-established 55+ Wellington Community. This community has a beautiful lake front with a private dock and access to Lake Howard that connects to the Chain of Lakes. This spacious home provides plenty of living space, with large bedrooms, and sliding doors that lead to a screened in lanai with a side rear

  Rick Hemenway CROSBY & ASSOCIATES, INC.

  689 Lake Howard Dr NW Unit 2D, Winter Haven, FL 33880
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  /73

  $325,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,011 Sq Ft

  5264 Green Dr, Winter Haven, FL 33884

  5264 Green Drive Winter Haven, Florida is a 3 Bedroom/2 Bath Provence floor plan located in Lake Ashton, a gated and guarded Florida 55+ community with resort style amenities and activities. This spacious and split floor plan home offers a Formal Dining Area, Living Room, Primary Suite, Guest Bedroom and Bedroom 3 is a Flex Room that could be an Office or additional Entertainment area. There is a

  Lori Raath LAKE ASHTON REALTY INC.

  5264 Green Dr, Winter Haven, FL 33884
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  /37

  $48,000

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,484 Sq Ft

  277 Alpine Dr Unit 277, Winter Haven, FL 33881

  Swiss Village / Lot #277 / 2 Bed/2 Bath / 1,484 Sq. Ft. / LAKE VIEW FOR $48,000.00 PRICE HAS BEEN REDUCED ALMOST 5K!!! 4 POINT INSPECTION HAS ALREADY BEEN DONE!! This spacious home is right across from the water and on a corner lot. It provides: New Gutters & Fascia, Double carport, New Appliances, Refreshed Kitchen (with new countertops, paint, hardware), New Kitchen/bathroom LVP flooring &

  Jennifer Torres CRF Communities

  277 Alpine Dr Unit 277, Winter Haven, FL 33881
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  /38

  $99,500

  $6K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  188 Sweet Cir, Winter Haven, FL 33884

  Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away

  Chris Cain MOSAIC SERVICES LLC

  188 Sweet Cir, Winter Haven, FL 33884
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  /29

  $284,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  4811 Khloe Ct, Winter Haven, FL 33884

  The property is located at 4811 Khloe Court WINTER HAVEN FL 33884 priced at 284900, the square foot and stories are 1504, 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

  4811 Khloe Ct, Winter Haven, FL 33884
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  /38

  $358,500

  $39K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,257 Sq Ft

  896 Vienna Dr, Winter Haven, FL 33884

  PRICE ADJUSTMENT LOWERED BY $11,500...YOU DON'T WANT TO MISS THIS OPPORTUNIY!!!LOOK AT THIS AMAZING MOVE IN READY HOME. Owner is ready to sell! This beautiful high-end Adams built home is located in SE Winter Haven. It is a stunning one story 4/3 move in ready home that was built in April 2022, less than a year old! When you enter the home, you will feel the magnitude of the open floor plan with

  Sherry Sapp COLDWELL BANKER REALTY

  896 Vienna Dr, Winter Haven, FL 33884
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  /31

  $254,900

  New Construction $9K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,673 Sq Ft

  2711 Gladiola Rd, Winter Haven, FL 33884

  Under Construction. The Glen is one of our two-story townhome floorplans featured in our Harmony at Lake Eloise community in Winter Haven, Florida. Welcome to this stylish and modern townhome nestled in a serene community. Boasting three spacious bedrooms, two and a half luxurious baths, and a convenient two-car garage, this residence offers the perfect blend of comfort and functionality. This

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  2711 Gladiola Rd, Winter Haven, FL 33884
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  /25

  $125,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  1700 6th St NW Unit B23, Winter Haven, FL 33881

  This beautifully maintained **DELUXE UNIT** is move-in ready and offers everything you’ve been searching for—located in a desirable **55+ community**, perfect for comfortable and peaceful living! What sets this unit apart is its **private in-unit laundry room**, a rare and valuable upgrade compared to other units in the community—adding both convenience and functionality. Enjoy improved energy

  Jean Julme CENTRIC REALTY SERVICES LLC

  1700 6th St NW Unit B23, Winter Haven, FL 33881
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  /5

  $319,990

  New Construction

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

  Hibiscus Plan at VillaMar - Signature Series, Winter Haven, FL 33884

  Open floor plan creates a unified living space with a large great room that overlooks the kitchen and dining area. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076787, Winter Haven, FL 33884
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  /29

  $279,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  4815 Khloe Ct, Winter Haven, FL 33884

  The property is located at 4815 Khloe Court WINTER HAVEN FL 33884 priced at 279900, the square foot and stories are 1504, 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

  4815 Khloe Ct, Winter Haven, FL 33884
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  /30

  $242,990

  New Construction

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

  4607 Linda Dr, Lake Wales, FL 33859

  The property is located at 4607 Linda Drive LAKE WALES FL 33859 priced at 232990, 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

  4607 Linda Dr, Lake Wales, FL 33859
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  /39

  $296,490

  New Construction

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

  ARIA Plan at VillaMar, Winter Haven, FL 33884

  The Aria is one of our one-story floorplans featured in Villamar in Winter Haven, Florida. With multiple exteriors to choose from, the Aria is a popular home. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,672 square feet of comfortable living. This all-concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room,

  D.R. Horton Builder

  3744 Giorgio Dr Unit 36202850, Winter Haven, FL 33884
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  /51

  $155,700

  $12K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  6308 Bayberry Blvd NE, Winter Haven, FL 33881

  LOW-COST YEAR AROUND LIVING! VERY WELL MAINTAINED! Fully Furnished everything stays! Pet Friendly lot. Gorgeous updating, Very Clean & Move-In ready! Brookhaven Village Resident Owned and located in the heart of Central Florida is a well-established and maintained age 55+ community. You Own your Lot! Perfect for winter months or year around living. Very affordable $34.00 monthly HOA which

  Don Cleveland COLDWELL BANKER REALTY

  6308 Bayberry Blvd NE, Winter Haven, FL 33881
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  /41

  $56,900

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft

  374 Putter Cir, Winter Haven, FL 33881

  2 Bed | 2 Bath | 950 square foot | $56,900 (Swiss Golf and Tennis- Lot 374) Fully furnished, tastefully updated and turn-key home in highly sought after 55+ community! Highlights include- Roof and AC replaced in 2024 for peace of mind- New Fridge- New Flooring- Starlink. Home features guest room at rear that has its own entry door and full bath with walk in shower. Plus, bonus room as you come in

  Brandi Sappington CRF Communities

  374 Putter Cir, Winter Haven, FL 33881
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  /33

  $300,990

  New Construction

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

  4045 Giorgio Dr, Winter Haven, FL 33884

  Under Construction. Introducing the Harper floorplan at Villamar, where every square foot is put to use with sophistication and comfort. Inside this 4 bedroom, 2 bathroom home, you’ll find 1,665 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. As you step inside, you are

  Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4045 Giorgio Dr, Winter Haven, FL 33884

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