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Southeast Winterhaven Homes for Sale

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  • /56

    $744,900

    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    226 Ruby Lake Ln, Winter Haven, FL 33884

    Welcome to this stunning 3 bedroom, 3 bathroom pool home offering gorgeous views of Lake Ruby. Set on a prime waterfront lot, the property includes an oversized 3-car garage and a private boat dock complete with an automated boat lift, making it ideal for boating and lakefront living.Designed with entertaining in mind, the open layout seamlessly blends indoor and outdoor spaces. Sliding

    Eric Chastain THE STONES REAL ESTATE FIRM

    226 Ruby Lake Ln, Winter Haven, FL 33884
  • /70

    $289,000

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

    6654 Crescent Loop, Winter Haven, FL 33884

    Discover this charming home nestled in desirable Southeast Winter Haven area, perfectly located within the Chain Of Lakes Elementary School zone. This well maintained, one-owner features a spacious split floor plan with 1820 Sq Ft Living, 4 bedrooms/2 baths offering ample space for families or guest. Home features Large kitchen with an inviting eat-in breakfast area, ideal for casual dining,

    Cindy Thornton AGILE GROUP REALTY

    6654 Crescent Loop, Winter Haven, FL 33884
  • /54

    $230,000

    • 2 Beds
    • 2 Baths
    • 1,078 Sq Ft

    715 Magnolia Place, Winter Haven, FL 33884

    Beautiful waterfront views, nightly sunsets, and direct access to the world-famous Winter Haven Chain of Lakes—welcome to this beautifully updated condo in the gated lakeside community of Winterset. Offering 2 bedrooms, 2 bathrooms, and its own private one-car garage, this residence blends comfort, style, and the relaxed Central Florida lakefront lifestyle. Step inside to discover an open and

    Michael Stone THE STONES REAL ESTATE FIRM

    715 Magnolia Place, Winter Haven, FL 33884
  • /95

    $695,000

    • 3 Beds
    • 2 Baths
    • 2,773 Sq Ft

    1336 Oakmont Dr, Winter Haven, FL 33884

    Welcome to your personal haven and next chapter in beautiful Lake Ashton—Central Florida’s premier 55+ active-adult community. This immaculate oasis radiates style, elegance, and Florida charm at every turn. From the striking bronze facia and windows to the fresh paint scheme and professional landscaping with concrete curbing, to the panoramic bronze-domed screened lanai with custom outdoor

    Brad Kirwan GLOBAL LIFESTYLE LLC

    1336 Oakmont Dr, Winter Haven, FL 33884
  • /57

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,847 Sq Ft

    4429 Turnberry Ln, Lake Wales, FL 33859

    Resort-Style Living in Lake Ashton's 55+ Community Golf, Pools & More! The CDD bond is paid in full! This move-in ready 3-bedroom, 2-bath home features a stunning decorative glass entry door with twin sidelights and an arched transom window that welcomes you into the grand foyer filled with natural light. The open floor plan features ceramic tile throughout the main living areas, beautiful crown

    Julie Seay COLDWELL BANKER REALTY

    4429 Turnberry Ln, Lake Wales, FL 33859
  • 4019 Penelope Ave Unit 37619581, Lake Wales, FL 33859

    $272,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    ARCHER II Plan at Annabelle Estates, Lake Wales, FL 33859

    The Archer II is one of our one-story floorplans features in our Annabelle Estates community in Lake Wales, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It

    D.R. Horton Builder
    4019 Penelope Ave Unit 37619581, Lake Wales, FL 33859
  • 4019 Penelope Ave Unit 37619580, Lake Wales, FL 33859

    $299,990 New Construction

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

    DUNDEE Plan at Annabelle Estates, Lake Wales, FL 33859

    Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Annabelle Estates in Lake Wales, 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
    4019 Penelope Ave Unit 37619580, Lake Wales, FL 33859
  • 4019 Penelope Ave Unit 37619577, Lake Wales, FL 33859

    $282,990 New Construction

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

    FREEPORT II Plan at Annabelle Estates, Lake Wales, FL 33859

    The Freeport II floorplan at Annabelle Estates offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with a

    D.R. Horton Builder
    4019 Penelope Ave Unit 37619577, Lake Wales, FL 33859
  • /21

    $299,999 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,039 Sq Ft

    5528 Taverna Way, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every

    Dale Human CASA FRESCA REALTY

    5528 Taverna Way, Winter Haven, FL 33884
  • /22

    $29,900

    • 1 Bed
    • 1 Bath
    • 618 Sq Ft

    5601 Cypress Gardens Rd Unit M14B, Winter Haven, FL 33884

    Cozy Retreat for Seniors - Move-In Ready & Fully Furnished! Located in Hammondell, a pet friendly, 55+ community situated in Winter Haven, Florida. Homes in this community are on lot leased land. Owning the home, but not the land, you pay a monthly lot rent of $640.00 whichgives you and your guest access to the amenities of the community, Lawn Mowing & Basic Cable TV are also included in the lot

    Bette Johnson Renee's Resales

    5601 Cypress Gardens Rd Unit M14B, Winter Haven, FL 33884
  • /5

    $1,490,000

    • Land
    • 8.01 Acres
    • $186,017 per Acre

    1030 Chalet Suzanne Rd, Lake Wales, FL 33859

    COMMERCIAL SITE READY FOR DEVELOPMENT...Existing building could have potential for remodel or demolished for new development. Located in growing area of Lake Wales with multi use allowed. Just off of Highway 27 and on North side of Chalet Suzanne Road from Eagle Ridge Mall. Don't miss this opportunity to secure this prime real estate. Call today for viewing appointment.

    Vicky Holloway LEGACY REAL ESTATE CENTER INC

    1030 Chalet Suzanne Rd, Lake Wales, FL 33859
  • /36

    $400,000

    • 3 Beds
    • 2 Baths
    • 2,035 Sq Ft

    353 Mandolin Ln, Winter Haven, FL 33884

    This beautiful 3-bedroom, 2-bath home with a den is located in the highly desirable gated community of Mandolin.From the moment you arrive, the charming front porch welcomes you—a perfect spot to sit and relax. Inside, the split bedroom floor plan ensures privacy for the entire family, while the spacious great room, filled with natural light, features a striking reclaimed wood accent wall

    Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

    353 Mandolin Ln, Winter Haven, FL 33884
  • /23

    $43,500

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    224 Hummingbird Ln Unit 25, Winter Haven, FL 33884

    This Beautiful 2 bedroom 2 bath home is located on Lake Winterset, chain of Lakes in Winter Haven Florida. The roof was updated 3/9/23 and the HVAC Approximately a couple years old. As you enter the home, there is a separate living space and straight ahead is the spacious Florida room. If you turn to the right and go up the stairs you come to another formal living space dining room area into the

    Joanne Gauthier Four Star Homes, Inc.

    224 Hummingbird Ln Unit 25, Winter Haven, FL 33884
  • /71

    $715,000

    • 4 Beds
    • 3 Baths
    • 2,591 Sq Ft

    105 Wyndham Dr, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Gated and guarded waterfront property in the prestigious community of Wyndham at Lake Winterset—welcome to 105 Wyndham Drive. This premium residence is ideally positioned within one of the area’s most desirable executive enclaves. From the moment you arrive, you’re greeted by an elegant brick-paved entry, stately wrought-iron gates, and manicured

    Michael Stone THE STONES REAL ESTATE FIRM

    105 Wyndham Dr, Winter Haven, FL 33884
  • /13

    $235,000

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

    656 W Date St W, Lake Wales, FL 33859

    Welcome to this warm and cozy home located right in Waverly, FL. This home is perfect for first-time buyers, families, or anyone wanting to enjoy some quiet in this calm neighborhood. This home has an open layout that allows so much natural light, and the spacious backyard is perfect for gardening, farming and so much more! Taking a step into the home you you will see that this beautiful home has

    Daniela Larin SANTIAGO & VAZQUEZ REAL ESTATE LLC

    656 W Date St W, Lake Wales, FL 33859
  • /22

    $269,900

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

    3832 Giorgio Dr, Winter Haven, FL 33884

    Immaculate, move in ready, 3bedroom/2 bath home. All appliances included with home. Blinds/curtains included. Open Floorplan great for Family get togethers. Neighborhood has 2 community pools, Clubhouse and playgrounds for your family ready to use. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include

    Alfredo Lopez FIERCE REALTY

    3832 Giorgio Dr, Winter Haven, FL 33884
  • /46

    $322,900

    • 3 Beds
    • 2 Baths
    • 1,871 Sq Ft

    4009 Bedford Ave, Winter Haven, FL 33884

    This fabulous Eco-Smart home is nestled in the highly desirable, maintenance-free, gated community of Traditions at Lake Ruby. Upon arrival, you’ll be welcomed by a charming front patio adorned with pavers, setting the stage for this beautifully maintained residence. Inside, the spacious great room boasts diagonally set tile flooring, crown molding, and oversized glass sliding doors that open to

    Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

    4009 Bedford Ave, Winter Haven, FL 33884
  • /13

    $289,380 New Construction

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

    3881 Giorgio Dr, Winter Haven, FL 33884

    Open kitchen flows to the dining space, great room and outside patio.

    Meritage Homes Builder
    3881 Giorgio Dr, Winter Haven, FL 33884
  • /100

    $625,000

    • 2 Beds
    • 2 Baths
    • 2,328 Sq Ft

    4276 Dunmore Dr, Lake Wales, FL 33859

    Welcome to your personal haven and next chapter in beautiful Lake Ashton—Central Florida’s premier 55+ active-adult community, home to the LA Travelers, the largest Family Motor Coach Association chapter in the southeastern United States. Designed as both a luxurious retreat and a stunning travel base, this immaculate home radiates style, elegance, and Florida charm while offering unmatched

    Brad Kirwan GLOBAL LIFESTYLE LLC

    4276 Dunmore Dr, Lake Wales, FL 33859
  • /73

    $448,900

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

    5225 Pebble Beach Blvd, Winter Haven, FL 33884

    This fully furnished, turnkey Lake Ashton retreat has everything you need to move in and start living immediately. From the moment you arrive, you'll appreciate the thoughtful upgrades and seamless flow of this 3-bedroom, 2-bath Sebastian model. The open-concept design showcases soaring ceilings, crown molding, and tile flooring throughout the main living areas, with triple sliders that lead to

    Candra Alston LAKE ASHTON REALTY INC.

    5225 Pebble Beach Blvd, Winter Haven, FL 33884
  • /17

    $327,728 Open Sun 12PM - 6PM

    • 4 Beds
    • 2 Baths
    • 1,919 Sq Ft

    5183 Kinsley Dr, Lake Wales, FL 33859

    **Take advantage of special financing + Flex Funds on quick move-in homes** This beautiful Ruby floorplan boasts an upgraded "C" elevation with laytite stone and 8' exterior doorway. The kitchen is highlighted with preeminent quartz countertops, upgraded 42" cabinets, and a stainless GE dishwasher, microwave, and stovetop. Contemporary 7"x22" wood grain tile adorns the entry way, great room,

    Stephanie Morales THE REALTY EXPERIENCE POWERED BY LRR

    5183 Kinsley Dr, Lake Wales, FL 33859
  • /17

    $334,965 Open Sun 12PM - 6PM

    • 4 Beds
    • 2 Baths
    • 1,919 Sq Ft

    5303 Mickey Ave, Lake Wales, FL 33859

    **Take advantage of special financing + Flex Funds on quick move-in homes** This beautiful Ruby floorplan boasts an upgraded "C" elevation with laytite stone and 8' exterior doorway. The kitchen is highlighted with preeminent quartz countertops, upgraded 42" cabinets, and a stainless GE dishwasher, microwave, and stovetop. Contemporary 7"x22" wood grain tile adorns the entry way, great room,

    Stephanie Morales THE REALTY EXPERIENCE POWERED BY LRR

    5303 Mickey Ave, Lake Wales, FL 33859
  • /55

    $399,900

    • 4 Beds
    • 3 Baths
    • 3,034 Sq Ft

    5392 Chandler Dr, Winter Haven, FL 33884

    Peaceful Waterfront Living! Many Beautiful Features & Oversized Living Areas Great for Entertaining! 3.2 Miles to Legoland! Formal Living & Dining Rooms, Family Room, and Bonus Room Upstairs great for crafts, reading, or toys. Oversized Primary Suite offers sitting area & plenty of closet space. Beautiful Kitchen with Cooking Island & Large Walk-in Pantry! Enjoy the Chain of Lakes in the

    Jenni Thompson KELLER WILLIAMS REALTY SMART

    5392 Chandler Dr, Winter Haven, FL 33884
  • /64

    $419,900

    • 3 Beds
    • 2 Baths
    • 2,312 Sq Ft

    4496 Strathmore Dr, Lake Wales, FL 33859

    THIS IS THE ONE YOU HAVE BEEN WAITING FOR!! CDD Bond PAID IN FULL! This beautifully upgraded 3-bedroom, 2-bath home in Lake Ashton Golf Community blends comfort, elegance, and lifestyle. Nestled on a desirable corner lot, it welcomes you with a screened front porch perfect for enjoying peaceful mornings and Florida breezes. Step inside to discover a thoughtfully designed split floor plan with

    Candra Alston LAKE ASHTON REALTY INC.

    4496 Strathmore Dr, Lake Wales, FL 33859
  • /76

    $412,000

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

    6212 Pinehurst Loop, Winter Haven, FL 33884

    PRICE REDUCED! 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. This delightful Sebastian home, with screened entry was BUILT in 2022 and features a spacious living area with abundant natural light, an upgraded kitchen paired with a Large Island (Great for

    Lori Raath LAKE ASHTON REALTY INC.

    6212 Pinehurst Loop, Winter Haven, FL 33884
  • /31

    $269,000

    • 3 Beds
    • 2 Baths
    • 1,914 Sq Ft

    131 Ruby Lake Dr, Winter Haven, FL 33884

    LOVELY HOME IN GATED COMMUNITY-Located in Ruby Lake this spacious home boasts high ceilings, throughout its 1,917 sq. ft. of living area. The layout features a formal living room, formal dining room, large family room, and a split-plan for the 3 bedrooms and 2 baths. The centrally located kitchen offers plenty of cabinet and counter space with the conveniences of a closet pantry, breakfast bar,

    Erin Floyd COLDWELL BANKER REALTY

    131 Ruby Lake Dr, Winter Haven, FL 33884
  • /20

    $289,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    6524 Domizio Dr, Winter Haven, FL 33884

    Move-in Ready! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. Personalize your home by

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 617-7929

    6524 Domizio Dr, Winter Haven, FL 33884
  • 0 Coming Early 2025 St Unit 37331381, Lake Wales, FL 33859

    $261,990 New Construction

    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    CAMERON Plan at Leoma's Landing, Lake Wales, FL 33859

    The Cameron is a thoughtfully designed one-story floorplan available in the beautiful Leoma's Landing community in Lake Wales, Florida. Homebuyers can choose from three modern exterior designs; each paired with a convenient one-car garage. This new construction home features 4 bedrooms, 2 bathrooms, and 1,560 square feet of open, comfortable living space. The open-concept design connects the

    D.R. Horton Builder
    0 Coming Early 2025 St Unit 37331381, Lake Wales, FL 33859
  • 0 Coming Early 2025 St Unit 37331376, Lake Wales, FL 33859

    $272,990 New Construction

    • 5 Beds
    • 2 Baths
    • 1,739 Sq Ft

    ALFORD Plan at Leoma's Landing, Lake Wales, FL 33859

    The Alford is one of our thoughtfully designed one-story floorplans, available in Leoma's Landing in Lake Wales, Florida. Choose from three modern exterior options, each paired with a convenient one-car garage. This spacious home offers 5 bedrooms, 2 bathrooms, and 1,739 square feet of comfortable living. Its open-concept design creates a seamless flow between the kitchen, dining, and living

    D.R. Horton Builder
    0 Coming Early 2025 St Unit 37331376, Lake Wales, FL 33859
  • /4

    $289,990 New Construction

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

    FREEPORT II Plan at Leoma's Landing, Lake Wales, FL 33859

    The Freeport floor plan at Leoma's Landing offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with a

    D.R. Horton Builder
    0 Coming Early 2025 St Unit 37331380, Lake Wales, FL 33859
  • 0 Coming Early 2025 St Unit 37331375, Lake Wales, FL 33859

    $299,990 New Construction

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

    DUNDEE Plan at Leoma's Landing, Lake Wales, FL 33859

    Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Leoma's Landing in Lake Wales, 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 seamlessly

    D.R. Horton Builder
    0 Coming Early 2025 St Unit 37331375, Lake Wales, FL 33859
  • 0 Coming Early 2025 St Unit 37331382, Lake Wales, FL 33859

    $248,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,223 Sq Ft

    GREENBRIAR Plan at Leoma's Landing, Lake Wales, FL 33859

    Discover the Greenbriar, a one-story home offered in the sought-after Leoma's Landing community in Lake Wales, Florida. This thoughtfully designed floorplan blends style, comfort, and functionality. Choose from three contemporary exterior elevations, each with a convenient one-car garage for everyday ease. Inside, the Greenbriar offers 3 bedrooms, 2 bathrooms, and 1,223 square feet of smart

    D.R. Horton Builder
    0 Coming Early 2025 St Unit 37331382, Lake Wales, FL 33859
  • /4

    $279,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    ARCHER II Plan at Leoma's Landing, Lake Wales, FL 33859

    The Archer II is one of our one-story floorplans features in our Leoma's Landing community in Lake Wales, Florida. Take your pick between three sleek exterior options when choosing this floorplan. Inside this 3-bedroom, 2-bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It

    D.R. Horton Builder
    0 Coming Early 2025 St Unit 37331374, Lake Wales, FL 33859
  • /89

    $497,900

    • 3 Beds
    • 2 Baths
    • 2,652 Sq Ft

    4315 Ashton Club Dr, Lake Wales, FL 33859

    CDD Debt Paid in Full. 3780 square feet under roof. Additional 423 sq. ft. air-conditioned & heated bonus room with vinyl windows — perfect as a sunroom. “Ready to Live Where Others Vacation?” Reduced to sell, bring your offers today. Do not miss this opportunity! Breathtaking Lake Ashton Home with Golf Course View, 55+ Community| Move-In Ready | Bonus: Furniture purchased in 2024 is

    Laurie Creel KELLER WILLIAMS REALTY SMART 1

    4315 Ashton Club Dr, Lake Wales, FL 33859
  • /25

    $788,670 New Construction

    • 5 Beds
    • 3 Baths
    • 2,907 Sq Ft

    1576 Ashton Covey Blvd, Winter Haven, FL 33884

    Pre-Construction. To be built. Welcome to Ashton Covey in Winter Haven! Discover the ultimate Florida lifestyle in this stunning community. Perfectly situated just off US Highway 27, your new home offers seamless access to work, outdoor recreation, shopping, dining, and more. Imagine being less than 15 minutes from Downtown Winter Haven, where charming local shops and restaurants await your

    Agent Photo

    William Maltbie

    MALTBIE REALTY GROUP

    (863) 431-3898

    1576 Ashton Covey Blvd, Winter Haven, FL 33884
  • /8

    $334,950 New Construction

    • 4 Beds
    • 3 Baths
    • 2,050 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
  • /14

    $365,900 New Construction

    • 4 - 5 Beds
    • 3.5 Baths
    • 2,819 Sq Ft

    Westbrooke II Plan at VillaMar - Highland Homes at VillaMar, Winter Haven, FL 33884

    Welcome home to the Westbrooke II by Highland Homes, a spacious two-story Florida home featuring an open living area on the first story and a flexible second-story layout! Downstairs, you will find a fully open living area including: A spacious gathering room. An open kitchen with a counter-height island, a large walk-in pantry, and a sunny dining cafe. A convenient powder room. The option to add

    Highland Homes Builder
    521 Vittorio Dr Unit 37316192, Winter Haven, FL 33884

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