Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: Whether you're a first-time buyer, downsizing, or investing, this canal-front townhome is an opportunity you don't want to miss. Enjoy access to Winter Haven's Chain of Lakes at a fraction of typical waterfront prices. This home features an open layout with modern finishes, ideal for everyday living and entertaining. A private lanai and second-story balcony overlook the canal, which connects to Lake Lulu, Lake Roy, Lake Eloise, and the 15 interconnected lakes of the Southern Chain of Winter Haven's Famous Chain of Lakes spanning over 9,000 acres of waterways. Or take some time for yourself to relax at the community pool on the banks of Lake Lulu. This townhome is centrally located near shopping, dining, and major roadways, offering convenient access to all things Winter Haven. Schedule your showing today.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Jay Scharff, Jr (863-651-5691)

Remarks: This property is eligible under the 30 Day Freddie Mac First Look Initiative through 05/28/2026. OWNER OCCUPIED BUYERS and NSP offers will only be considered the first 30 days from initial MLS input date. Investors are encouraged to make an offer and will be considered after the First Look Initiative period has expired. Buyer pays Doc Stamps on deed. This 2022 home is barely lived in, Island kitchen opens to the great room plan, hard surface counter tops in the baths, 2 car garage, water filtration system. Home is in great condition. Call today to preview this home.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Barry Macchione (863-604-7455)

Remarks: Virtually Staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept floorplan, perfect for entertaining or just hanging out, is complemented by stylish luxury vinyl plank flooring. The kitchen and throughout the home feature elegant quartz countertops, while the stainless-steel appliances and smart thermostat with voice control add a touch of modern technology. The laundry room features a new washer and dryer and is conveniently located upstairs with all the bedrooms. The owner’s suite is situated at the back of the home with a spa-like owner’s bathroom and spacious walk-in closet. Completing this home is beautifully designed landscaping curated for the Florida lifestyle. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Welcome to 1985 Sarah Street, a 2025-built home in Winter Haven that perfectly blends modern design, functional space, and move-in-ready convenience. Situated on a premium corner lot with a fully fenced backyard, this 4-bedroom, 2.5-bathroom home offers 1,874 square feet of thoughtfully designed living space—ideal for both everyday living and entertaining. Step inside and immediately feel the difference. The entire first floor is designed for connection, featuring a bright, open-concept layout where the kitchen, dining, and living areas flow seamlessly together. The kitchen is bright and spacious—complete with upgraded stone countertops, modern finishes, and a clean, fresh look that feels straight out of a model home. Tile flooring throughout the main level adds both style and durability. Upstairs, the home continues to impress. A cozy loft space creates the perfect flex area—ideal for a second living room, home office, media space or home gym. The spacious bedrooms deliver comfort for everyone, while the owner’s suite provides a true retreat with a walk-in closet and an upgraded modern shower door in the primary bathroom. Step outside and you’ll find one of this home’s standout features—a large, fully fenced backyard, offering privacy, space to play, entertain, or simply unwind. The corner lot positioning adds extra breathing room and curb appeal that’s hard to find. Located in the desirable Peace Creek Reserve community, you’ll enjoy the benefits of newer construction living in a growing area known for its natural beauty and proximity to Winter Haven’s famous Chain of Lakes, shopping, and dining. Why wait for new construction when you can have better than new—right now? This home is upgraded and move-in-ready immediately.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Tyler Wampler (863-577-1234)

Remarks: Filled with potential and flexibility, this home is perfect for buyers looking to add their own style and create value. "A great opportunity for buyers or investors to customize and build equity. The layout includes 4 bedrooms, 2 full bathrooms, a living room, kitchen, den, And a laundry room. Ideal for a family with a growing household. This home offers 1,437 sq ft of living space on a 7,148 sq ft lot, with a new roof installed in 2023 and HVAC updated in 2022. Make this home yours today!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Mikisha Joseph (813-810-8576)

Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully maintained 2018-built single-family home located at 1327 Salisbury Drive in Winter Haven, the best value for this size in the area! Offering approximately 2,300 square feet of living space, this spacious residence features 5 bedrooms, 3.5 bathrooms, and a two-car garage. The primary suite is conveniently located on the first floor, providing privacy and comfort, while the upstairs bedrooms are carpeted for a warm, cozy feel. The interior has been freshly painted, creating a bright and move-in-ready atmosphere throughout. Enjoy Florida living year-round from the screened-in back patio, perfect for relaxing or entertaining. It is conveniently located just minutes from downtown Winter Haven and close to the area’s picturesque lakes, shopping, dining, and major roadways. This home combines modern construction, generous space, and an excellent location. Schedule your private showing today!

Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)

Listing Agent: Joshua Nogowski (754-234-9626)

Remarks: Under contract-accepting backup offers. Welcome to refined Florida living in the serene, gated, 55+ community of Preserve at Lakeside Landings. This community designed with enjoying your Florida lifestyle, is home to 44 residences, 2 pools, a playground, and sidewalks to keep you active. HOA includes lawn maintenance which allows you to relax in your stunning new home! Thoughtfully designed with a triple-split floorplan, this residence offers exceptional privacy and versatility—ideal for multi-generational living. Manicured tropical landscaping and pristine sidewalks lead you inside, where the first split features two guest bedrooms and a shared bathroom. Continuing into the main corridor, you’ll find the third bedroom or office along with the conveniently located laundry room.The home then opens into a bright, airy living space with 9-foot ceilings and tile flooring. An elegant dining area overlooks the pool, while the beautifully appointed kitchen showcases solid wood cabinetry, granite countertops, stainless steel appliances, and a generous island perfect for entertaining. The primary suite serves as a peaceful retreat with updated flooring, a walk-in closet, and a spa-inspired bath complete with dual sinks, granite, and a glass walk-in shower. Outdoors, the property transforms into a true tropical sanctuary. A stunning saltwater pool with a cascading waterfall is framed by lush landscaping that is home to several citrus trees. This secluded, spa-like atmosphere is ideal for relaxation or entertaining. With a tranquil natural backdrop and effortless indoor-outdoor flow, this home blends elegance, comfort, and resort-style appeal. Fresh interior paint, an immaculate garage, energy-efficient insulation, and lawn care included in the HOA make this home truly move-in ready—offering a lifestyle of ease, beauty, and authentic Florida living. Upgrades include kitchen appliances 2025, new disposal, Pentair salt system is 4 years old. Pool deck was sealed one year ago. Don't hesitate, opportunities like this are rare, so make your appointment today!

Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)

Listing Agent: Cyleste Goodson (863-701-3487)

Remarks: Spacious 3-Bedroom Home with Investment Potential Welcome to this beautifully maintained home featuring three generously sized bedrooms, including a primary suite with a walk-in closet, offering ample storage and comfort. The two additional bedrooms each feature built-in closets, perfect for family, guests, or tenants. Enjoy the convenience of two full bathrooms, a bright and open floor plan, and expansive living and dining areas that create the perfect space for entertaining or relaxing. The modern kitchen is both stylish and functional, ready for daily cooking or hosting gatherings. Additional highlights include a 2-car attached garage for secure parking and storage, and ceiling fans in all bedrooms and the living room, ensuring comfort and energy efficiency year-round. The home is also equipped with seamless gutters around the entire house, offering long-term durability and low maintenance. Whether you're looking for a primary residence or a smart investment property, this home checks all the boxes. With its spacious layout, attractive features, and low-maintenance upgrades, it’s a fantastic opportunity for investors seeking long-term value and strong rental appeal. Don't miss out—schedule your showing today and discover the potential this property offers!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Osvaldo Junior (407-693-3133)

Remarks: Charming & Renovated Single Family Home With NO HOA & Great Investment Potential! Welcome to this cozy 3 Bed, 1 Bath residence that features a seamless open floor plan, with a bright living room and dining room combo that flows into the modern kitchen. The interior has been thoughtfully updated with luxury vinyl and tile flooring throughout, providing a stylish and easy-to-clean environment. The private backyard is spacious and perfect for outdoor gardening or relaxing. Located just 5 miles from LEGOLAND Florida, this property offers excellent access to major highways, hospitals, lakes, and all of Central Florida's top attractions. The home is "rental-ready" and has strong income potential as a short-term or long-term rental. Schedule a private tour and make this beautiful home your new residence or add to your income producing profolio... Matterport 3D tour is available that provide virtual 3D tour & room measurements.

Listing is courtesy of: KN PREMIER REALTY, INC (407-668-8888)

Listing Agent: Guanhua Zhang (407-668-8888)

Remarks: Virtually Staged. Under Construction. Welcome to this stunning Poinciana floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2,110 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous white cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Welcome to the Winter Haven community of Krenson Bay. This 3bd/2ba home was built in 2022 with the property condition like new! Move in ready with an open layout of kitchen/dining/family room combo. The kitchen has stainless steel appliances and a large island to host gatherings. Located close to major highways and LEGOLAND! Schedule your showing today!

Listing is courtesy of: WIN-WIN REAL ESTATE SERVICES LLC (407-271-3069)

Listing Agent: Lisa Manzo (407-271-3069)

Remarks: Welcome to this beautifully maintained 4-bedroom, 3-bathroom pool home situated on a desirable corner lot in Winter Haven! Offering a flexible floor plan, the spacious 4th bedroom can easily serve as a bonus room, home office, playroom or guest suite to fit your lifestyle. Inside, you'll find a stylish luxury vinyl plan flooring throughout and an open-concept living area perfect for everyday living and entertaining. The kitchen features granite countertops, ample cabinetry and an eat-in dining area. Step outside to your private backyard oasis complete with a sparkling pool, ideal for enjoying Florida's year-round sunshine. With a low HOA and a convenient location between Tampa and Orlando, this home offers the perfect combination of comfort, flexibility, and value. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Amanda Plowden (863-224-7088)

Remarks: Brand-new 3-bedroom, 2-story townhome with garage in Winter Haven, FL! This professionally designed home features an open-concept main level with a spacious gathering room, flex space, powder room, and private covered lanai. The modern kitchen offers shaker-style soft-close cabinets, premium laminate countertops, stainless steel Samsung appliances, a breakfast bar, and walk-in pantry. Upstairs includes a private owner’s suite with walk-in closet and dual-vanity en-suite bath, plus two generous secondary bedrooms sharing a dual-vanity hall bath. Enjoy low-maintenance luxury vinyl plank flooring, stain-resistant carpet, energy-efficient LED lighting, built-in pest control, and energy-saving features including R-30 insulation, Low-E windows, and a programmable thermostat—move-in ready with style and efficiency.

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: PRICED TO SELL!! **GORGEOUS VIEWS FROM THIS FURNISHED DIRECT LAKEFRONT CONDO** THE 2ND BEDROOM EXTENDS THE LIVING AREA AND CAN BE CLOSED FOR GUEST BEDROOM USE. THIS BEAUTIFUL CONDO IS ON THE SOUTH "CHAIN OF LAKES" IN WINTER HAVEN, FLORIDA (CENTER OF THE STATE LOCATION). THE NICE QUALITY FURNITURE IS INCLUDED. The monthly fee includes cable, internet, water, sewer, trash removal, roof, building insurance, ground maintenance, use of the pool, recreational room, exercise room, and library. The custom design features in this condominium are; raised panel wood cabinets in the kitchen, beautiful granite countertops, custom tile backsplash, stainless steel appliances, and up to date paint selections. Spring Lake Towers Condominium is an (age 55+) NON-SMOKING, NO PETS complex. BOAT SLIPS are currently available for a reasonable yearly fee. This condo complex is immaculate and conveniently located to grocery, shopping, movie theater, medical, places of worship, restaurants, bus line & downtown Winter Haven. Spring Lake Towers holds occasional social events and planned group activities if you wish to participate. This is truly living the Florida lifestyle with a gorgeous lakefront setting. Make this your full-time residence or a winter home. All information is believed to be accurate but not guaranteed. Make your showing appointment today as it is sure to sell quickly. Measurements are approximate.

Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)

Listing Agent: Chris Goode (863-287-5454)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: One or more photo(s) has been virtually staged. 2-Bedroom, 2-Bathroom Mobile Home in a 55+ Community of ORANGE MANOR WEST-NO LOT RENT!-This spacious 1,352 sq. ft. double wide mobile home located in a 55+ community that offers a wealth of amenities for an active lifestyle. BRAND NEW A/C! The living room features sliding glass doors that open to a front enclosed Florida room, perfect for enjoying the view of your front yard. The kitchen comes fully equipped with all appliances and a separate dining room for your meals. BRAND NEW REFRIGERATOR AND RANGE. The main bedroom boasts an en-suite bathroom and a walk-in closet. The second bedroom is adjacent to a recently updated bathroom. Inside laundry room with additional storage, washer, and dryer included. A long carport that can accommodate two cars, with a garage door leading to extra storage space. Roof: Installed in 2017. Community Amenities: Pool, Clubhouse with billiards and library,Putt-putt golf, Bocce ball and horseshoe fields, Shuffleboard and Basketball court. Please note, this park does not allow pets. Don’t miss out on this wonderful opportunity! Call now for more details.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Kelley Blackburn (813-478-0023)

Remarks: Imagine yourself starting each morning with a cup of coffee on your covered lanai, enjoying the peaceful Florida weather before the day begins. Step inside this beautifully upgraded 3-bedroom, 2-bath split-plan home and you’ll immediately notice the care that’s been put into every detail. From the updated flooring throughout the bedrooms, living room, and dining room to the stunning epoxy countertops in the kitchen and bathrooms, this home blends comfort and style effortlessly. The kitchen has been refreshed with a modern backsplash, while new ceiling fans in the living room and primary bedroom add the perfect finishing touch. Outside, you’ll enjoy the privacy of a fully fenced backyard, a whole-home water filtration system, and the peace of mind that comes with a new roof installed in 2023. Conveniently located just minutes from I-4, shopping, dining, and entertainment, you’ll have everything you need close to home. Plus, enjoy access to two community pools and a community playing field. This isn’t just a house—it’s where movie nights become traditions, morning coffee becomes a ritual, and ordinary moments become memories. Ready to make it yours? Let’s schedule your private showing today.

Listing is courtesy of: OPULENT REALTY INTERNATIONAL (863-323-7778)

Listing Agent: Sara Avellaneda (863-390-1985)

Remarks: 5553 Hogan Lane, Winter Haven, Fl. 33884 is located in Lake Ashton, a Gated and Guarded Premier 55+ community with Resort Style Amenities, Planned Activities, (2)-18 Hole Golf Courses, Pro Shop and Boat Slip Rentals. This St. Croix floor plan home with tile flooring throughout has a view of Lake Hart and has no backyard neighbors. You'll love the unobstructed view of the lake and the tranquil living this home offers. Upon entering you will love the Open and Spacious living area with cathedral ceilings, giving the home an expansive and airy feel. The focal point from the entrance of this home is the water view in the back of the home. Double French Doors open to the covered lanai and extended birdcage. This 2 Bedroom/2 Bath home with Flex Room offers over 1,858 sq. ft. living area. The expanded kitchen with additional cabinetry provides an abundance of storage and counter top space. Kitchen highlights include: granite countertops, tiled backsplash, maple cabinets, gas stove, breakfast bar and pendant lights. Initial Construction upgrades in this home include: pocket doors, 250 gallon propane tank buried to service stove & gas grill hook up, whole house water softener system, fans in all rooms, a whole house (except A/C) generator, the lanai is wired for hurricane shutters. The garage floors have epoxy finish, skeeter beater, wire shelving, attic above garage has flooring with pull down stairs for additional storage. Improvements since 2023 include: A/C Heat Pump and Air Handler have been replaced, Closets added to the Entry way, Guest Room and Flex Room, New Interior Paint, New Bosch Dishwasher, New Hardware on Cabinetry, Recessed Lighting in the Kitchen, New Chandelier, New Door Handles with Locks, New Toilets, Towel Fixtures, New Landscaping with Poured Curbing, New Plants and Rock. Residents in Lake Ashton enjoy a Main Clubhouse with Movie Theater, Bowling Lanes, Card, Craft and Billiard Rooms, Fitness Center and Outdoor Pool. There is also a Health and Fitness Center with Indoor Pool, Card, Craft and Billiard Rooms, Fitness Center with Sauna, Indoor 1/2 Court Basketball, Indoor Racquetball. Bocce Courts, Pickle Ball, and Tennis Courts are Enjoyed by Residents, Too. There is a great variety of clubs & activities available for residents. You can be as active as you like, or stay put & enjoy the serenity of your new home. Make an appointment to tour this home today!

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-409-6899)

Listing Agent: Lori Raath (863-409-6899)

Remarks: This 2 BR, 2 BA home is located near Rotary Park and Kiwanis Park, which is on Lake Martha, both public parks. Each park has room for games and family gatherings. Rotary Park has a baseball field with backstop and other outside activity areas. This home is located near schools, the Winter Haven downtown post office, the Winter Haven (Bay Care Hospital) and several doctors offices and medical clinics. The Winter Haven Public Library is also 6+/- blocks to the west of this property. The home has a metal roof which offers a long life and better storm protection than typical asphalt shingles. The windows have been replaced and the central A/c - Heat system has recently been inspected. A detached storage building provides room for lawn equipment or other items not needed inside the residence, but are more easily accessed than typical attic space provides. The interior of the home has been extensively renovated with both bathrooms remodeled.

Listing is courtesy of: TOWN & COUNTRY REAL ESTATE (863-293-1141)

Listing Agent: Timothy Irby (863-206-4464)

Remarks: Under Construction. Brand new, energy-efficient home available by May 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home providing plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)