Winter Haven, FL Homes for Sale under $500,000

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  $500,000

  • 4 Beds
  • 2 Baths
  • 1,842 Sq Ft

  1400 Axel Cir, Winter Haven, FL 33880

  Beautiful 4 bedrooms, 2 bathrooms home built in 2022, offered fully furnished and move-in ready — just bring your toothbrush. Located in Winter Haven, FL, only a few miles from LEGOLAND. Modern open floor plan, spacious kitchen, and comfortable living areas, perfect as a primary residence, vacation home, or short-term rental investment. Enjoy a great location near attractions, shopping, dining,

  Domingo Hernandez Ugarit Realty

  1400 Axel Cir, Winter Haven, FL 33880
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  /72

  $439,000

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

  1209 Sawgrass Dr, Winter Haven, FL 33884

  Your Florida Dream Home Awaits in Lake Ashton, an exclusive gated 55+ community. A golf membership (expires Sept. 30, 2026) for a single golfer will convey. Discover this beautiful 3 bedroom, 2 bathroom Sebastian Floor Plan home with an oversized backyard with pond and trees beyond. This PET FREE home is perfectly positioned; one home removed from a cul-de-sac. With over 2,045 sq. ft. living

  Lori Raath LAKE ASHTON REALTY INC.

  1209 Sawgrass Dr, Winter Haven, FL 33884
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  /43

  $459,900

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

  6308 Pinehurst Loop, Winter Haven, FL 33884

  Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton 55+ golf community—where luxury meets an active, resort-style lifestyle. This thoughtfully designed home features top-notch upgrades throughout, including an additional sliding glass door leading to the back patio, flooding the living space with

  Cliff Glansen FLATFEE.COM

  6308 Pinehurst Loop, Winter Haven, FL 33884
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  /47

  $429,900

  • 3 Beds
  • 2 Baths
  • 2,319 Sq Ft

  106 Jardin Ln, Winter Haven, FL 33884

  Located in the desirable Gardens of Interlochen, this beautifully renovated and impeccably maintained 3-bedroom, 2-bath residence at 106 Jardin Lane offers thoughtful upgrades, timeless finishes, and a functional open layout designed for both everyday comfort and effortless entertaining. At the heart of the home is a stunning renovated kitchen featuring granite countertops, LG black stainless

  Deanna Stone THE STONES REAL ESTATE FIRM

  106 Jardin Ln, Winter Haven, FL 33884
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  /25

  $440,000

  • 4 Beds
  • 3 Baths
  • 2,206 Sq Ft

  252 Lake Link Rd, Winter Haven, FL 33884

  SELLER IS OFFERING $5,000 towards closing depending on offer!!! Welcome to this beautifully updated 4 bedroom, 3 bath pool home, ideally positioned on a half-acre lot in the highly desirable gated community of Lake Link. Surrounded by oak-lined streets and refreshing lake breezes, this home combines elegant updates with a functional layout designed for everyday living and entertaining. Inside, an

  Katie Melson THE STONES REAL ESTATE FIRM

  252 Lake Link Rd, Winter Haven, FL 33884
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  /25

  $434,900

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  240 Santa Rosa Dr, Winter Haven, FL 33884

  *** Motivated seller! Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! *** Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the

  Brian Surrency LIVE FLORIDA REALTY

  240 Santa Rosa Dr, Winter Haven, FL 33884
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  $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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  /99

  $469,000

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

  6165 Pebble Beach Blvd, Winter Haven, FL 33884

  Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained 3-bedroom, 2-bath home awaits. From the stone on the front elevation and bronze screened front entry to the 32’ x 18’ bronze screened veranda, the home impresses in every way. It is situated on a quiet cul-de-sac with views of a large pond and

  Brad Kirwan GLOBAL LIFESTYLE LLC

  6165 Pebble Beach Blvd, Winter Haven, FL 33884
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  /25

  $439,000

  • 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
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  /65

  $445,000

  • 3 Beds
  • 2 Baths
  • 2,354 Sq Ft

  4048 Phoenician Way, Winter Haven, FL 33884

  Lake Ashton is a 55+ golf community with all the amenities you could ask for including movie theatre, bowling alley, pickle ball, tennis, bocce, fitness centers, two clubhouses and so much more! This highly upgraded 3-bedroom, St John floor plan home is breathtaking! Once inside the elegant beveled double French glass door entry you will be amazed at the impeccably executed home finish. Such as,

  Armando Perez HEROES REAL ESTATE GROUP LLC

  4048 Phoenician Way, Winter Haven, FL 33884
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  /26

  $479,900

  • 3 Beds
  • 2 Baths
  • 2,023 Sq Ft

  3971 Island Lakes Dr, Winter Haven, FL 33881

  2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step

  Keith St. Onge LA ROSA REALTY PRESTIGE

  3971 Island Lakes Dr, Winter Haven, FL 33881
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  /24

  $465,000

  • 4 Beds
  • 3.5 Baths
  • 2,722 Sq Ft

  2014 8th Terrace SE, Winter Haven, FL 33880

  Experience the best of Winter Haven living in this beautifully updated 4 bedroom, 3.5 bath home offering Lake Lulu views and a prime central location just minutes from downtown, dining, and the Chain of Lakes. Thoughtfully designed with flexible spaces, you’ll find two primary suites, a warm family room with lake views, and French doors opening to a wrap-around screened porch—perfect for morning

  Chad Lindsey LOKATION

  2014 8th Terrace SE, Winter Haven, FL 33880
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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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  $499,000

  • 4 Beds
  • 3.5 Baths
  • 3,377 Sq Ft

  824 Lake Elbert Ct, Winter Haven, FL 33881

  Welcome to 824 Lake Elbert Ct, a beautifully updated 4 bedroom, 3.5 bathroom pool home offering over 3,300 sq. ft. of living space near Lake Elbert. This spacious two-story home is designed for both everyday living and entertaining, with multiple areas to gather and relax. The main level features a formal living room, formal dining room, a bright breakfast nook, and a large family room that can

  Lizzette Crispin EMPIRE NETWORK REALTY

  824 Lake Elbert Ct, Winter Haven, FL 33881
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  /29

  $449,000

  • 5 Beds
  • 5 Baths
  • 3,015 Sq Ft

  724 W Central Ave, Winter Haven, FL 33880

  Great investment opportunity! Tenant-occupied property in a central location with strong rental demand. Short sale subject to lender approval. Sold as-is, no repairs. Do not disturb tenants. No seller/creative financing.

  Miraya Lane KELLER WILLIAMS ADVANTAGE III

  724 W Central Ave, Winter Haven, FL 33880
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  /63

  $500,000

  • 5 Beds
  • 2 Baths
  • 2,006 Sq Ft

  1818 6th St SE, Winter Haven, FL 33880

  ***FULLY RENOVATED***Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 3-bedroom, 2-bathroom home.This beautiful property fully renovated with the total 5 bedrooms, new kitchen, new living room, new floor, new bathrooms and the best new backyard in the city. Nestled between Orlando and Tampa with no HOA or CDD, this property offers unmatched freedom and

  Erika Pinto GARCIA REALTY GROUP

  1818 6th St SE, Winter Haven, FL 33880
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  /71

  $420,000

  • 3 Beds
  • 2 Baths
  • 2,031 Sq Ft

  5225 Pebble Beach Blvd, Winter Haven, FL 33884

  HUGE PRICE ADJUSTMENT — MOTIVATED SELLER! Welcome to this beautifully, open-concept Sebastian model FULLY FURNISHED and TURNKEY, allowing you to settle in and start enjoying the Lake Ashton lifestyle from day one. Grand, high ceilings immediately draw your eyes to the serene 17th-hole golf view, offering a peaceful backdrop perfect for relaxed living. The living room is anchored by a stunning

  Candra Alston LAKE ASHTON REALTY INC.

  5225 Pebble Beach Blvd, Winter Haven, FL 33884
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  /79

  $412,000

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  6212 Pinehurst Loop, Winter Haven, FL 33884

  Welcome to this modern residence at 6212 Pinehurst Loop Winter Haven, Fl. 33884, designed with 3 Bedrooms and 2 full bathrooms PLUS an additional room that could be used as a Den/Office. Seller to pay off the CDD Debt Balance at the time of Closing. SAVING YOU THOUSANDS!!! This delightful Sebastian home, with screened entry was BUILT in 2022 and features a spacious living area with abundant

  Lori Raath LAKE ASHTON REALTY INC.

  6212 Pinehurst Loop, Winter Haven, FL 33884
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  /35

  $434,900

  • 3 Beds
  • 2 Baths
  • 1,475 Sq Ft

  4273 Stafford Dr, Winter Haven, FL 33880

  This 3 bedroom 2 bath home is located in an established neighborhood close to the Polk parkway for easy access to Orlando or Tampa. The Kitchen is equipped with stainless steel appliances, wood cabinets, granite counter tops, breakfast bar. There is a fire place and a wet bar in the large living room with beautiful tile & wood flooring throughout the home. The back porch is screened and the

  Phillip Thomas THOMAS REALTY

  4273 Stafford Dr, Winter Haven, FL 33880
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  /49

  $405,000

  • 3 Beds
  • 2 Baths
  • 2,218 Sq Ft

  104 Woden Way, Winter Haven, FL 33884

  Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single family home. This special villa has a functional layout with updated features throughout. A screened entry with leaded glass doors opens to vaulted ceilings and custom architectural touches.The open concept kitchen includes granite countertops,

  Karen Myers CENTURY 21 MYERS REALTY

  104 Woden Way, Winter Haven, FL 33884
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  /18

  $475,000

  • Land
  • 11.52 Acres
  • $41,233 per Acre

  0 Lucerne Park Rd Unit MFRO6281805, Winter Haven, FL 33881

  Prime Investment Opportunity! This 11+ acre vacant lot is zoned R-3 multi-family and residential, providing exceptional potential for development. Featuring approximately 1,047 feet of frontage along State Road 544, the property is situated in a rapidly growing area—ideal for investors and developers. Nearby utilities include electric, water, and sewer for convenient access. All dimensions are

  Cardichon Christloudjy EXP REALTY LLC

  0 Lucerne Park Rd Unit MFRO6281805, Winter Haven, FL 33881
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  /10

  $400,000

  • Land
  • 0.39 Acre
  • $1,025,641 per Acre

  152 & 148 Avenue D SW, Winter Haven, FL 33880

  Two previously residential lots combined to make .39 Acres of land in heart of Downtown Winter Haven. The lots are leveled and ready to build. The current zoning on the property is MX within the Primary Urban Core which allows for multi-family, various commercial and mixed-use opportunities. Combined frontage on Ave D and 2nd Street with an alley off the south end of the property allowing

  Erik Polumbo POLK REALTY ADVISORS LLC

  152 & 148 Avenue D SW, Winter Haven, FL 33880
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  /17

  $495,000

  • Land
  • 4.27 Acres
  • $115,925 per Acre

  0 Pollard Rd, Winter Haven, FL 33884

  This property is located on Pollard Road, which has just been repaved. With the new easement, acquired by the City of Winter Haven, street lights have been added and also City water and City sewer is available. And best of all there is NO HOA. This property is in a rural setting, with the occasional train passing by, yet, less than 5 miles from Publix or the local theme park. Currently, this

  Jim Campbell CENTURY 21 MYERS REALTY

  0 Pollard Rd, Winter Haven, FL 33884
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  $442,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,490 Sq Ft

  1753 Hummingbird Rd, Winter Haven, FL 33884

  The property is located at 1753 Hummingbird Road WINTER HAVEN FL 33884 priced at 442990, the square foot and stories are 2490, 1.The number of bath is 3, halfbath is 0 there are 5 bedrooms and 3 garages. For more details please, call or email.

  D.R. Horton Builder

  1753 Hummingbird Rd, Winter Haven, FL 33884
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  /29

  $420,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,336 Sq Ft

  1749 Hummingbird Rd, Winter Haven, FL 33884

  The property is located at 1749 Hummingbird Road WINTER HAVEN FL 33884 priced at 420990, the square foot and stories are 2336, 1.The number of bath is 3, halfbath is 0 there are 4 bedrooms and 3 garages. For more details please, call or email.

  D.R. Horton Builder

  1749 Hummingbird Rd, Winter Haven, FL 33884
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  /18

  $450,000 New Construction

  • 4 Beds
  • 4 Baths
  • 2,804 Sq Ft

  306 Avenue P NW, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Brand-New 2025 Duplex Appraised @$484,000 walk into this with equity build in– An exceptional investment opportunity in the thriving heart of Winter Haven, just minutes from world-renowned theme parks. Each unit showcases a spacious, modern design with 2 bedrooms and 2 bathrooms, offering the perfect balance of style, comfort, and functionality for

  Amalia Lucena TRUE FLORIDA REALTY LLC

  306 Avenue P NW, Winter Haven, FL 33881
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  /31

  $409,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,244 Sq Ft

  1774 White Elephant Loop, Winter Haven, FL 33884

  Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home perfectly positioned on a corner lot with no side neighbors and no front neighbors. Located right next to the community playground, this home offers both privacy and convenience for families. As you step inside, a long and welcoming foyer sets the stage for the open and thoughtfully designed

  Gayle Van Wagenen LGI REALTY- FLORIDA, LLC

  1774 White Elephant Loop, Winter Haven, FL 33884
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  /25

  $403,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,244 Sq Ft

  1790 White Elephant Loop, Winter Haven, FL 33884

  Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home designed for modern living. Conveniently located close to the community playground, this home offers easy access to outdoor fun while maintaining a peaceful setting. As you enter, a long and inviting foyer leads into the heart of the home. The first floor boasts a bright and open family room,

  Gayle Van Wagenen LGI REALTY- FLORIDA, LLC

  1790 White Elephant Loop, Winter Haven, FL 33884
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  $464,990 New Construction

  • 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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  /27

  $411,950 New Construction

  • 4 - 6 Beds
  • 2.5 - 3.5 Baths
  • 3,030 Sq Ft

  Ammolite Plan at Annabelle Estates, Lake Wales, FL 33859

  The main floor of the inviting Ammolite plan offers a private study and versatile flex space, which can be optioned as an additional bedroom and bathroom or a guest suite, complete with living room. You'll also appreciate a convenient powder room; a nook; a great room and a well-appointed kitchen with a center island, a large pantry and optional additional cabinets. Upstairs, discover an airy

  Richmond American Homes Builder

  4130 Old Bartow Lake Wales Rd Unit 37335446, Lake Wales, FL 33859
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  /9

  $403,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,244 Sq Ft

  Spring Plan at Peach Crossings, Winter Haven, FL 33884

  The Spring plan by LGI Homes is a beautiful five-bedroom, two-story home. The first floor of this home features a spacious family room and chef-ready kitchen, along with a guest bedroom and full bath. The master retreat and three secondary bedrooms are found upstairs. You will love having a large laundry room with exceptional storage space!

  LGI Homes Builder

  1609 Nantucket Way Unit 36502866, Winter Haven, FL 33884
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  $434,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,490 Sq Ft

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

  Find all the space you need in our popular one-story Covington floorplan in Harmony at Lake Eloise, one of our communities in Winter Haven, Florida. This unique 5 bedroom, 3 bathroom and 3 car garage floorplan is available in 3 different modern exteriors. As you enter the foyer you are greeted with bedrooms 2 and 3 that are separated by a full bathroom complete with quartz countertops. As you

  D.R. Horton Builder

  1651 Hummingbird Rd Unit 36202782, Winter Haven, FL 33880
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  $477,990 New Construction

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

  1745 Hummingbird Rd, Winter Haven, FL 33884

  The property is located at 1745 Hummingbird Road WINTER HAVEN FL 33884 priced at 477990, the square foot and stories are 2787, 1.The number of bath is 3, halfbath is 1 there are 4 bedrooms and 3 garages. For more details please, call or email.

  D.R. Horton Builder

  1745 Hummingbird Rd, Winter Haven, FL 33884
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  /35

  $400,000

  • 5 Beds
  • 3 Baths
  • 2,579 Sq Ft

  129 Lake Otis Rd, Winter Haven, FL 33884

  Short Sale. This charming home is a diamond in the rough, waiting for the right owner to unlock its full potential. Located in a sought-after neighborhood of picturesque red brick homes, this property offers a unique opportunity for those with vision and ambition. This home is being sold as a short sale, making it an ideal project for those looking to invest in a renovation loan and transform it

  Kelley Vogel Blackburn COLDWELL BANKER REALTY

  129 Lake Otis Rd, Winter Haven, FL 33884
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  $495,000

  • 3 Beds
  • 2 Baths
  • 1,589 Sq Ft

  4129 Limerick Dr, Lake Wales, FL 33859

  IDEAL LOCATION! AMAZING VIEW!!!! 4129 Limerick Drive Lake Wales, Florida is located on the 1st hole of Lake Ashton's East Golf Course. The location of this DeSoto RV home is desirable and offers a spectacular view of the morning sunrise over Lake Ashton. You'll enjoy the unobstructed golf and water views from one of the best lots in Lake Ashton. This 3 Bedroom / 2 Bath RV home offers a double car

  Lori Raath LAKE ASHTON REALTY INC.

  4129 Limerick Dr, Lake Wales, FL 33859
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  /98

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,255 Sq Ft

  4152 Dunmore Dr, Lake Wales, FL 33859

  LAKE WALES – GATED LAKE ASHTON GOLF CLUB 55+ RESORT WITH A FAIRWAY VIEW – HUGE CLASS A RV, BOAT, OR CLASSIC CAR STACKING GARAGE - Enjoy resort-style living in the highly sought-after, active adult community of Lake Ashton Golf Club. This impeccably maintained RV home is perfectly situated along the 18th fairway, offering picturesque golf course views and stunning sunsets. Conveniently located

  Amie Samuel-Hall CHARLES RUTENBERG REALTY INC

  4152 Dunmore Dr, Lake Wales, FL 33859
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  $495,000

  • 3 Beds
  • 3 Baths
  • 1,511 Sq Ft

  4152 Limerick Dr, Lake Wales, FL 33859

  CDD DEBT PAID IN FULL! Beautiful water view from the Screened Lanai on the back of this RV HOME in Lake Ashton! Welcome to your ideal seasonal home located in Lake Ashton, a premier 55+ community. Offering security with a guarded and gated entrance, year round activities and amenities exclusive for the residents, this RV Home, a Desoto Floor Plan, features 3 Bedrooms and 3 Baths. The RV garage

  Lori Raath LAKE ASHTON REALTY INC.

  4152 Limerick Dr, Lake Wales, FL 33859

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