Winter Haven Homes For Sale & Real Estate - 724 homes

Remarks: AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by a bright, open floor plan where the living room, dining area, and kitchen flow together seamlessly ideal for everyday living and effortless entertaining. The kitchen is generously sized, featuring an abundance of cabinetry and two lazy Susan's that maximize every inch of storage. Natural light floods the home through an impressive array of windows, and sliding glass doors in the main bedroom, middle bedroom, and living room all open directly onto the crown jewel of this property: a stunning 47 x 15 screened-in patio complete with a bar area, built-in grill, refrigerator, and cabinetry. Whether you're hosting guests or simply enjoying a quiet Florida evening, this outdoor space delivers. Both bathrooms have been tastefully updated. The guest bath features a brand-new tub and shower installed by Westshore Homes in October 2025, along with a new vanity, mirrored medicine cabinet, cabinet above the toilet, and new toilet. The main bathroom has also been refreshed with a new mirrored medicine cabinet, cabinet above the toilet, and new toilet. Major systems are all squared away brand-new roof in 2025, A/C replaced in 2021, and water heater from 2018 offering true peace of mind from day one. The home is also pre-wired for a generator, a smart bonus for Central Florida living. The attached garage includes a dedicated laundry and storage room with extensive shelving, and the washer and dryer convey with the home. Set on an 8,537 square foot lot at the end of a tucked-away cul-de-sac, this property offers the rare combination of privacy, space, and convenience. Just minutes from US-27, LEGOLAND Florida Resort, Winter Haven Hospital, Polk State College, and the renowned Chain of Lakes, everything Central Florida has to offer is right at your doorstep. Homes this move-in ready, this well-maintained, and this well-located don't stay on the market long schedule your private showing today! Offers may be entered ONLINE through Monday, April 20, 2026 at 2:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.

Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)

Listing Agent: Daniel Rodriguez (407-934-0305)

Remarks: Under Construction. Brand new, energy-efficient home available by Aug 2025! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. 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: REDUCED!! Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets & oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting,pvc plumbing, irrigation well/pump, pole barn for RV parking 28x20’ and outside carport laundry room, This home offers updated plumbing and abundant parking. Pride of Ownership. A must see!

Listing is courtesy of: WATSON & WATSON INC REALTORS (863-294-4149)

Listing Agent: Wendy Gibbs (863-557-5249)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath condominium. It's located in the highly sought-after 55+ Imperial Harbor community of Winter Haven. Convenient elevator access makes daily living effortless in this serene lakefront retreat. Start your mornings with a walk to the private community dock on Lake Howard, where fishing and boating await. Enjoy an array of resort-style amenities, including a heated pool, fitness center, shuffleboard, and billiards, all designed to support an active and relaxed lifestyle. Ideally situated just 45 minutes from both Tampa and Orlando, this central location offers the perfect balance of tranquility and accessibility. Inside, the open and airy floor plan feels inviting and relaxing. Refinished cabinets, fresh paint throughout and new double pane insulated windows make this home move-in ready! The primary suite is bright and spacious and two additional bedrooms provide flexibility for guests, hobbies, or a home office. An in-unit laundry closet with washer and dryer adds everyday convenience. HOA fees also include water, basic cable, and internet—making this an exceptional opportunity for low-maintenance, carefree living. Schedule a private tour today !

Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)

Listing Agent: William Kilpatrick (863-669-8090)

Remarks: Auction Property. ***Auction will run April 27th 2026- May 7th 2026 *** 2 bedroom 1 bathroom house ***All property information to be verified by buyers*** Property is sold with any outstanding code violations, liens, or expired permits. Buyer to do own research prior to bidding.

Listing is courtesy of: A BETTER LIFE REALTY (727-521-7378)

Listing Agent: Tony Kelly (863-287-4672)

Remarks: Under contract-accepting backup offers. This charming Winter Haven home offers comfort, functionality, and a convenient location. Featuring a well-designed layout with spacious living areas and natural light throughout, this property is perfect for homeowners or investors alike. The kitchen provides ample cabinet space and flows easily into the main living area, creating an inviting space for everyday living and entertaining. The bedrooms are comfortably sized, and the home offers a functional floor plan ideal for a variety of lifestyles. Situated in a quiet neighborhood, this property is close to shopping, dining, schools, and major roadways, providing easy access to all that Winter Haven has to give. Whether you’re a first-time buyer, downsizing, or looking for an investment opportunity, this home delivers great value and potential.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Phillip Randall (407-202-2096)

Remarks: Welcome to this newly renovated 3-bedroom, 1-bath home conveniently located near Lake Cannon and just minutes from all the dining, shopping, and entertainment that Winter Haven and Auburndale have to offer! Step through the front door to find fresh interior paint, new carpet in all bedrooms, and inviting living spaces. The kitchen has been refreshed with brand-new appliances, provides plenty of cabinetry storage and counter space, and has a convenient layout for everyday cooking and entertaining. The bathroom is your own personal retreat featuring a new vanity and a walk-in shower with a dual shower head system. Major updates include a new roof and a newer A/C unit, giving you peace of mind and comfort year-round. Outside, the property is truly unique. Enjoy mornings on your screened-in front porch, or host gatherings on the spacious screened-in back porch complete with an attached utility room. The fenced backyard offers plenty of space for pets or play, and comes complete with a firepit, detached shed, and extra covered storage. There is also an extra wide driveway providing plenty of off-street parking. This home is the perfect blend of comfort, outdoor space, and accessibility to the amenities near you. Don’t miss your chance to see this one!

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

Remarks: Perfect for Investors! This duplex is located on a corner lot in a very affordable market. This property features two units, each consisting of two bedrooms and one bathroom. Both units are approximately 1758 ft.² generating roughly 2800 a month rental income. Roof was replaced in 2023, new AC unit in unit two, newly repainted.

Listing is courtesy of: IRON VALLEY REAL ESTATE OSCEOLA (407-698-4663)

Listing Agent: Marcy Smiley Theobald (407-908-4042)

Remarks: One or more photo(s) has been virtually staged. Pictures of plants are staged. LISTED BELOW APPRAISED VALUE!!! Welcome to 626 Pavare Ct, a charming completely remodeled 2-bedroom, 2-bath end unit condo located in the desirable Orchid Springs community. Step inside this 823 sqft second-level residence, where an open floor plan welcomes you with luxury vinyl flooring and soothing neutral paint tones. The living room effortlessly flows into the dining area and kitchen, creating an ideal setting for daily living. The kitchen is well-equipped with a like new range, brand new refrigerator, and like new stackable washer/dryer, elegant tile backsplash, deep sink with island all and bar stools. The primary suite offers a walk-in closet and an ensuite bath with a brand new walk-in shower, while the secondary full guest bath features a brand new tub/shower combo both with sliding glass doors. Condo is elegantly equipped beautiful gold finished faucets, large head showers, and heated/lighted mirrors in both bathrooms. Step out onto the private balcony and enjoy relaxing views of the landscaped grounds. Residents have access to a sparkling community pool, perfect for hot summer days. An assigned parking spot is conveniently located near the condo, and a guest parking spot is also included. Orchid Springs offers a convenient location with easy access to nearby shopping, dining, entertainment, medical facilities, and major transportation routes to Tampa and Orlando. The monthly condo fees of $284 covers ground, exterior building maintenance, and community amenities. The community welcomes a pet and residents over the age of 14, with annual rentals allowed. Whether you're looking for a starter home, a retirement retreat, a secondary residence, or an investment property, this condo has it all. Don't miss out on this opportunity! There is a clubhouse that is available for rent for special events! Call today to schedule a private tour and make this condo your new home.

Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)

Listing Agent: Misty Mcteer (863-557-0641)

Remarks: Welcome to a rare blend of space, flexibility, and opportunity at 525 7th St NE in the heart of Winter Haven. Set on a desirable corner lot with NO HOA, this property invites you in with a bright, open-concept design that feels both airy and welcoming from the moment you arrive. The main living area is thoughtfully designed for everyday comfort and effortless entertaining, featuring three spacious bedrooms and three full bathrooms. The kitchen serves as the centerpiece of the home, showcasing elegant stone (quartz) countertops, stainless steel appliances, updated cabinetry with under-cabinet lighting, and a generous dining area perfect for gathering with family and friends. A standout feature of this property is the private in-law suite, complete with its own entrance, bedroom, bathroom, and built-in kitchenette. Whether you're hosting guests, accommodating multigenerational living, or seeking rental income, this space offers exceptional versatility. Currently leased to a reliable tenant through April 30, 2026 with potential to extend. It provides immediate income potential for investors or future flexibility for homeowners. Significant upgrades add both value and peace of mind, including a new roof (2023), updated HVAC system (2022), smart garage door (2022), and approximately $60,000 in renovations completed between 2022–2023. Additional highlights include new flooring throughout, fresh carpet in key areas, and a custom built-in entertainment center with a Murphy bed for added functionality. Step outside to enjoy a fully fenced yard designed for relaxation and enjoyment. The welcoming front porch sets the tone, while the backyard offers a lush collection of fruit and plantings. You can find in the backyard mango, cherry, banana, lemon, and aloe vera creating your own private oasis. Conveniently located near Lake Elbert, Downtown Winter Haven, Polk State College, and a wide range of shopping, dining, parks, and medical facilities, this home delivers on both lifestyle and location. Whether you're searching for a primary residence, an income-producing property, or a home with flexible living options, this one truly has it all. Schedule a tour today.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Veronica Figueroa (407-519-3980)

Remarks: Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this immaculately maintained three-bedroom, two-bath home with a den offers exceptional comfort and elegance, including a beautiful primary suite with its own relaxing sitting room and a sparkling 7½' x 36' bromine pool awaiting your enjoyment. From the striking stone front elevation and bronze screened front entry to the expansive 51' x 13' bronze screened veranda, this home impresses at every turn. Perfectly positioned on a large pond with a nature preserve beyond, it provides delightful sunrise views and frequent sightings of the abundant wildlife that makes Lake Ashton so special. Step inside through the elegant double glass doors and immediately notice the clean, crisp, and welcoming feel that creates the ideal setting for both relaxed everyday living and gracious entertaining. The interior showcases stunning terraced crown molding, coffered ceilings in both the living room and primary bedroom, and five solar tubes that fill the home with abundant natural light. The kitchen is beautifully appointed with gorgeous cabinetry featuring two glass-front cabinets, a wine rack, and rich black granite countertops, complemented by a large walk-in pantry offering generous storage space. Both bathrooms include walk-in showers and granite counters, adding style and convenience. One of the home’s most remarkable highlights is the expansive screened enclosure with pool at the rear of the property, where the views of the pond, wildlife, and nature preserve are among the finest along Hogan Lane. Additional peace of mind comes from an updated air conditioning system and a roof that is only three years old. Residents of Lake Ashton enjoy unmatched amenities including two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, and so much more, creating an active and fulfilling lifestyle. This exceptional property offers the perfect blend of comfort, convenience, and community—schedule your private showing today and experience the very best of Florida living.

Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)

Listing Agent: Brad Kirwan (863-280-0390)

Remarks: Under Construction. New construction home with 2227 square feet on two-story including 5 bedrooms, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 2 and 3 share a jack-and-Jill bathroom. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and decor do not convey."

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

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

Remarks: BIG PRICE REDUCTION – $7,000! Recently Fully Renovated Townhouse – Move-In Ready! Seller offering $4,000 credit toward buyer’s closing costs or interest rate buydown. Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and worry-free living: All 3 bathrooms fully renovated with fresh, modern finishes Brand-new kitchen featuring stainless steel appliances (refrigerator, gas range, range hood, microwave), new sink & faucet, New A/C system & new gas water heater for comfort and efficiency Fresh paint throughout (walls, doors, and closets), New vertical and window blinds, New ceiling fans with remote controls and stylish light fixtures in every room, balcony, and lanai, Garage floor freshly painted for a clean, polished look, Washer and dryer included. The spacious main living area is filled with natural light and opens to an extra-large screened lanai, perfect for entertaining or relaxing outdoors. Upstairs, both bedrooms are oversized with private bathrooms, and the primary suite features its own screened balcony. All 3 Bathrooms are renovated, brand new vanities. Prime Winter Haven Location! Next to the new collegiate baseball stadium and parks project, bringing $60M in growth to the city, Direct access to Lake Lulu, part of the Chain of 22 Lakes for boating, fishing, and outdoor fun, Walking distance to dining and shopping: Starbucks, Chick-fil-A, Panera, Outback, Red Lobster, Steps from the Rowdy Gaines Olympic Pool and Advent Fieldhouse, This townhouse is truly move-in ready—all major upgrades are already completed. Perfect as a primary residence, vacation home, or investment property in one of Winter Haven’s most desirable communities. Schedule your private showing today!

Listing is courtesy of: HIGDON HOMES REALTY LLC (863-209-2543)

Listing Agent: Fatma Higdon (863-209-5243)

Remarks: Under contract-accepting backup offers. Welcome to this inviting 3 bedroom, 2 bath home with 1,860 sqft of living space in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious family room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a fireplace with built-in bookshelves, creating a warm and welcoming atmosphere. Enjoy a fully fenced backyard, offering privacy and plenty of space for outdoor living, gardening, or pets. Located in a sought-after area, this home combines comfort, character, and convenience—close to schools, shopping, dining, Legoland and all that Winter Haven has to offer. Don’t miss the opportunity to make this beautiful property your own—schedule your showing today!

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this well loved, one owner 2 bedroom 2 bath home. The charming kitchen has a breakfast nook with bay window, breakfast bar, generous countertops, and cabinet space. The bright, and open great room as well as both bedrooms have recently updated Luxury Vinyl Plank floors for easy care. You'll be snug, and secure during storm season with electric hurricane shutters, and a 2020 Generac generator. The roof was replaced in 2024, and a new hot water tank installed in 2024.This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low maintenance lifestyle, in a welcoming setting. The reasonable monthly fee includes all community amenities, lawn mowing, and a Spectrum Internet/Cable/TV package. Residents enjoy access to the community pool, fitness center, billiards, movie theater, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Marti Sutton (863-206-0563)

Remarks: Opportunity is knocking in Winter Haven! This 2-bedroom, 1-bath single-family home offers the perfect canvas for investors, flippers, or buyers looking to build instant equity. The property needs work, which is exactly where the upside lies — bring your vision and your contractor, and turn this into a solid rental or a profitable resale. Located in a quiet, established residential neighborhood with a close-knit community feel, you're just minutes from US Hwy 17, local dining, shops, and all that Winter Haven has to offer. Winter Haven continues to grow, making this an ideal time to plant your flag in Polk County. Priced for the market it is — don't sleep on this one.

Listing is courtesy of: ENCORE INVESTMENT REALTY (407-334-8664)

Listing Agent: Desmond Pollock (407-334-8664)

Remarks: Under contract-accepting backup offers. Welcome to this well-maintained 3-bedroom, 2-bathroom home situated on a desirable corner lot in Winter Haven. Conveniently located in the heart of Central Florida, Winter Haven is known for its Chain of Lakes, Legoland, local parks, shopping, dining, and easy access to both Orlando and Tampa. This property offers a functional layout with thoughtful updates throughout. The updated kitchen features quartz countertops, ample dark wood cabinetry, and a convenient breakfast bar. Recent improvements include tile flooring and an upgraded electrical panel, adding both style and peace of mind. The primary bedroom includes a walk-in closet, while the additional bedrooms provide flexibility for a variety of uses. Step outside to enjoy the large screened-in porch, ideal for relaxing or entertaining, all within a fully fenced yard with durable PVC fencing. The irrigation system is controlled by a Hydrawise WiFi system, allowing for easy and efficient lawn maintenance. Additional highlights include a 2-car garage, a circular driveway for added parking and convenience, and a roof replaced in 2018. With no HOA or CDD fees, this property offers added flexibility and fewer restrictions. Located near Winter Haven’s popular Chain of Lakes, as well as nearby shopping, dining, and major roadways, this home provides both comfort and accessibility.

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

Listing Agent: Garrett Robinson (863-838-5210)

Remarks: Check out this well maintained home located in Oakwood Estates, a 55+ community, located in Sunny central Florida. The home features a very open and inviting kitchen, perfect for entertaining. The cooktop and built in oven have been updated. Step into the primary bedroom to find plenty of space for a king size bed, then step into the remodeled and updated primary bathroom. The split bedroom floor plan offers privacy to guests with a bathroom conveniently located outside the door. All the flooring is a laminate with no carpeting in the home. Enjoy the peaceful screened side porch. The home is located on a corner lot with a Florida room giving views of both streets, a great place for your morning coffee. The double pane windows and window AC offers additional living space when guests arrive. Oakwood Estates offers many amenities and activities. You can be as busy as you would like or enjoy the peaceful community and watch the world go by.

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

Listing Agent: Kathy Devor (573-450-1679)

Remarks: Under contract-accepting backup offers. Looking for a gated community, 3 bedroom home with a bonus room? No need to look any further! Welcome to the highly sought-after Cypresswood Golf Community, where comfort, security, and convenience come together in this spacious 3-bedroom, 2-bath home with an added air conditioned Florida Room that offers a flexible bonus space perfect for anything your lifestyle calls for. Enjoy beautiful golf course views right from your backyard...a peaceful and scenic setting you won’t want to miss! From the moment you arrive, you’ll appreciate the private front patio, offering a peaceful outdoor space to relax or entertain. Step inside to a home that is completely carpet-free, featuring durable laminate and tile flooring throughout, including the garage which is designed for both easy maintenance and a clean, modern feel. The interior layout provides a generous and open living space, with natural flow between the living, dining, and kitchen areas, making it ideal for everyday living and gatherings. One of the standout features is the Florida Room (with A/C), offering incredible flexibility. Whether used as a playroom, home office, guest space, or private suite, this area can easily be adapted to fit your needs complete with the option for a separate private entrance. The garage has been thoughtfully enhanced with a full kitchen setup, creating a unique and functional space perfect for outdoor entertaining, hosting, or extended cooking needs..an efficient and valuable addition. Community features you’ll love living in Cypresswood Golf & Country Club means access to: 24-hour guarded and gated entry,Community pool,Tennis courts,18-hole championship golf course, Clubhouse and on-site restaurant.Prime location conveniently located near U.S. Highway 27, I-4, and the Polk Parkway. This home offers easy access to everything Central Florida has to offer, including:LEGOLAND, Pega Pig Theme Park, Walt Disney World, Orlando International Airport and Tampa International Airport,Gulf Coast beaches near St. Petersburg and Tampa! Surrounded by a growing area filled with shopping, dining, and everyday conveniences, this location supports both lifestyle and accessibility. This home offers versatility, unique features, and access to a lifestyle-rich community—a true opportunity to enjoy the best of Florida living. Don't miss this opportunity! Come see it today!

Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)

Listing Agent: Daniel Rodriguez (407-934-0305)

Remarks: This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)