A Homes for Sale in Winter Haven - 26 homes

Remarks: Income-producing 5-unit multifamily property in Winter Haven with 3 units currently leased and one vacant unit offering additional income potential. Recent improvements include a new metal roof, updated HVAC system, and interior/exterior upgrades completed within the past year. Located near shopping, dining, schools, and major roadways in a strong rental market. Ideal for investors seeking cash flow, portfolio expansion, or value-add potential.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Brand-New NO HOA, NO CDD, 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 long-term tenants or short-term guests. Built with quality craftsmanship, this property features luxury vinyl plank flooring, sleek granite countertops, and premium stainless steel appliances (including refrigerator, range hood, and microwave) in both units. The open-concept layout, combined with abundant natural light, creates a warm and contemporary living environment. Adding to its value, each unit comes with separate electric and sewer meters—a rare and highly desirable feature that enhances convenience for both owners and tenants. Whether you’re seeking a turnkey rental investment, a vacation property near top Florida attractions, or a low-maintenance income-producing duplex, this brand-new build delivers it all. Don’t miss out—schedule your private tour today!

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

Listing Agent: Amalia Lucena (904-614-1930)

Remarks: Under contract-accepting backup offers. RARE OPPORTUNITY! Situated on a sprawling 2.5-acre parcel, 232 Cutrone Rd presents a rare opportunity with exceptional potential. Offered as-is, the true value lies in the land, making it ideal for investors, builders, or buyers seeking space and flexibility. The property opens the door to a variety of possibilities, including potential subdivision, redevelopment, or the creation of a private compound. The existing home is in distressed condition and will require significant renovation or may be best suited for a complete rebuild, providing a blank canvas to bring your vision to life. Large parcels with this level of versatility are becoming increasingly scarce. Don’t miss your chance to capitalize on this unique offering. The Seller does not guarantee these possibilities, must be verified with the county directly. ***Buyer to perform all due diligence regarding zoning, subdivision, and future use; seller makes no representations***

Listing is courtesy of: RE/MAX COLLECTIVE (813-438-7841)

Listing Agent: Carrissa Henshaw (813-419-3154)

Remarks: CHAIN OF LAKES THREE BEDROOM TOWNHOME!!! Beautiful views & wildlife abound at this low-maintenance home on the water that has been updated, remodeled & ready to move in! You'll enjoy the open floor plan with modern, updated kitchen, stainless appliances and Corian countertops, spacious living area & downstairs powder room. French doors open to a tiled & screened lakefront lanai, and the sunsets are absolutely breathtaking from the back yard! Enjoy fishing, grilling or take your boat out for a cruise after a "dip" in the lakefront community pool. The townhome features a large private primary bedroom with an en-suite bath and lakefront balcony that offers incredible water views. There are two additional bedrooms & the guest bath is located on the second floor. There is an attached one-car garage, and the community offers additional fee-based recreational vehicle parking. Location, location! This gem is centrally located, and you can walk to local restaurants & Publix, and it's close to medical and a vibrant downtown Winter Haven area where you can enjoy the local farmers market, night life and great dining. This property is a slice of "Lakefront Paradise"! Call today to see this rare property!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: Under contract-accepting backup offers. Charming and efficient 1-bedroom, 1-bath home in Winter Haven, perfect for simple living or an investment opportunity. With 480 sq ft, this home offers a functional layout that makes the most of the space, including a cozy living area, kitchen, and private bedroom. The property sits on a spacious lot, giving you room to expand, add outdoor features, or simply enjoy extra space — a rare find for a home this size. Conveniently located near shopping, dining, and major roads, this home is ideal for buyers looking for an affordable option or investors seeking rental potential. Great opportunity with plenty of possibilities—schedule your showing today.

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

Listing Agent: Malak Hassani Benbachir (863-624-7266)

Remarks: One or more photo(s) has been virtually staged. Welcome to 306 Ave P NW – a fantastic opportunity for first-time home buyers or savvy investors! Now offered as separate units for added affordability and flexibility, this property is perfect for buyers looking to own instead of rent. This well-maintained home features bright living spaces, functional layouts, and great potential to personalize and build equity. Whether you’re looking for your first home, a mortgage helper opportunity, or an affordable investment, this property checks all the boxes. Located in a convenient neighborhood close to schools, parks, shopping, and everyday amenities, you’ll love the value and potential this property offers. Why rent when you can own? Don’t miss your chance to get into the market with this affordable and versatile property. Quick possession available — motivated seller!

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

Listing Agent: Ricky Miller, Jr (407-453-8679)

Remarks: Discover this charming first-floor corner unit condo in the highly sought after Orchid Springs community in SE WInter Haven. This 2 bedroom 2 bathroom condo features a desirable split floor plan with an oversized living area perfect for entertaining or relaxing. Both bedrooms boast generous walk-in closets , and offers abundant storage throughout. Enjoy the convenience of a first floor corner location with a covered parking spot. The nice open layout makes every day maintenance free living easy and comfortable. Residents of Orchid Springs love the prime location minutes from shopping,dining, medical facilities, and Legoland, while being centrally situated between Tampa and Orlando for easy access to everything Central Florida has to provide. The HOA takes care of the details including grounds maintenance, water , sewer and gas giving you more time to enjoy the Florida Lifestyle. Whether you are looking for a primary residence or a winter retreat , this first floor corner unit is a fantastic opportunity in a desirable community. Schedule your showing today and make this condo your new home!

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Rosalia Abreu (954-854-3694)

Remarks: One or more photo(s) has been virtually staged. Welcome to 306 Ave P NW – a fantastic opportunity for first-time home buyers or savvy investors! Now offered as separate units for added affordability and flexibility, this property is perfect for buyers looking to own instead of rent. This well-maintained home features bright living spaces, functional layouts, and great potential to personalize and build equity. Whether you’re looking for your first home, a mortgage helper opportunity, or an affordable investment, this property checks all the boxes. Located in a convenient neighborhood close to schools, parks, shopping, and everyday amenities, you’ll love the value and potential this property offers. Why rent when you can own? Don’t miss your chance to get into the market with this affordable and versatile property. Quick possession available — motivated seller!

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

Listing Agent: Ricky Miller, Jr (407-453-8679)

Remarks: Welcome to true lakefront living on the renowned Chain of Lakes in Winter Haven, perfectly positioned on Lake Shipp with approximately 500 feet of waterfrontage, an extremely rare offering that creates the feel of your own private park right in your backyard. Built in 2021 with block-on-slab construction and a durable metal roof, this 3-bedroom, 3-bathroom home was designed to maximize water views and effortless indoor-outdoor living. Inside, you’ll find soaring ceilings and an open layout that flows seamlessly into the kitchen, featuring 42-inch cabinetry, quartz countertops, a large island, pantry, and a dine-in area—ideal for entertaining or everyday living. Large 8-foot sliding glass doors open out to a fully screened lanai that spans the entire width of the living area, creating a true extension of the home and the perfect place to relax while overlooking the water. The split floor plan offers privacy, with a spacious primary suite positioned to capture lake views, complete with a large walk-in closet and a spa-style en-suite bathroom featuring double vanities and a walk-in shower. One of the additional bedrooms also features its own en-suite bathroom, creating a secondary primary suite—ideal for guests or multi-generational living. The remaining bedroom is well-sized and positioned for convenience. Step outside and embrace the lifestyle this property was built for. With your own private dock, you can moor your boat and enjoy direct access to the Chain of Lakes. Cruise across to local favorites like Harborside Restaurant and take in some of the best sunsets Central Florida has to offer. Additional features include plantation shutters on the front of the home, a spacious indoor laundry room, a detached storage shed, and a rare drive-through 3-car garage with access from the front all the way to the backyard—perfect for boats, trailers, or additional vehicles. With no HOA and close proximity to downtown Winter Haven, this property delivers a unique combination of space, convenience, and true waterfront living. This is more than just a home—it’s a rare opportunity to own a standout piece of lakefront property on the Chain.

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

Listing Agent: David Small (407-601-8351)

Remarks: Under Construction. PRICE REDUCED $9,600 FOR QUICK SALE !!!!!!!! Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.

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

Listing Agent: Juan Carrion (863-581-6028)

Remarks: Under Construction. PRICE REDUCED $9,600 FOR QUICK SALE !!!!!!!! Discover this stunning brand-new construction 3-bedroom, 2-bath home with an open living space and a convenient 2-car garage, this move-in-ready gem boasts elegant granite countertops in the kitchen for a touch of luxury and everyday functionality. The bright, airy layout offers three spacious bedrooms, two full baths, and a peaceful setting perfect for relaxing or family life—ideal for first-time buyers or those seeking fresh, contemporary Florida living. Minutes from shopping, dining, parks, and the Chain of Lakes, this serene location combines tranquility with easy access to everything Central Florida offers. Don't miss this pristine new build—schedule your private tour today! All measurements and sizes are deemed to be accurate but not guaranteed; any information contained here that is critical to buyers' purchasing decisions must be verified by the buyers. Private financing is available to qualified buyers.

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

Listing Agent: Juan Carrion (863-581-6028)

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: THE PROPERTY ADVISERS (863-651-5691)

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

Remarks: Beautiful lakefront living awaits in the gated community of Winterset! This beautifully maintained 2-bedroom, 2-bathroom condo with an attached one-car garage offers stunning lake views, abundant natural light, and unique architectural details throughout. Inside, you’ll find beautiful cork flooring, specialty tray ceilings, and a cozy library area complete with custom built-in shelving. The spacious enclosed Florida room is a true showstopper, featuring floor-to-ceiling windows overlooking the lake, creating the perfect space to relax and enjoy breathtaking water views year-round. The oversized primary suite offers a spacious layout with dual sinks, a walk-in closet, and a peaceful retreat-like feel. The large custom kitchen is a chef’s dream, complete with a gas stove, ample cabinetry, generous counter space, and plenty of storage for all your culinary needs. Enjoy the beautiful community amenities that include a pool, tennis courts, and the security and privacy of this sought-after gated neighborhood. Conveniently located near Legoland, shopping, dining, and everyday conveniences. This lakefront condo perfectly blends comfort, elegance, and Florida lifestyle living.

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Jill Lingenfelter (863-242-0900)

Remarks: Location Location!! NO HOA, NO CDD, Built in 2020. QUIET, YET CONVENIENT LOCATION! Whether you're shopping for a first home, Investment or last home, this beauty is just what you’ve been looking for! Beautiful 3BR/2BA home open floor plan, living room/dinning groom /family room kitchen combo. located in NE Winter Haven. Large walk in closet in the Master Bedroom/Bath. Master bath contains a shower and tub, as well as double vanity. Kitchen comes equipped with stainless steel appliances, Vinyl flooring consistent through entire home, central a/c and heating. All stainless-steel appliances convey. This home will not last long, call today for your private showing.

Listing is courtesy of: VYLLA HOME (813-947-7996)

Listing Agent: Manny Duran, Jr (407-334-8893)

Remarks: Welcome to Brandy Chase Village!! This well desired 55+ community located in Winter Haven Florida is centrally located between Tampa and Orlando. The beautiful 2 bedroom and 2 bathroom home is well maintained and ready for you! Enjoy your oversized sunroom that adds extra square footage of living space for you to enjoy. Updated appliances and a new AC was installed in 2021 , as well as it was replumbed in 2021. Assigned covered parking space with additional guest parking spot. Are looking for a new primary residence , to downsize or a winter getaway? Either way you will not be disappointed with everything this property offers. Beautiful grounds and low cost HOA fee which includes water/sewer, garbage,lawn care, clubhouse and pool maintenance. Minutes from the Polk Parkway and the neighboring cities of Lakeland , Auburndale and Bartow this is the perfect location for you! Call today for your showing , don't miss out on your opportunity to call Brandy Chase your home!

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Rosalia Abreu (954-854-3694)

Remarks: Under contract-accepting backup offers. Cute home in a great central location. It has served as a great rental property for 20 years. The back patio has a lot of potential for private outdoor space

Listing is courtesy of: COLLANY PROPERTIES (863-295-9886)

Listing Agent: Christopher Collany (863-412-2170)

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: Need space? This private gated 2.38-acre Winter Haven property with NO HOA offers room to live, play, and grow—bring your RV, boat, ATV, and all your toys. Set well back from the road behind a remote-operated gated entry, this property delivers the privacy and convenience buyers are actively searching for in Winter Haven and throughout Polk County. The fully fenced acreage gives you the freedom to create the lifestyle you want—whether it’s kids playing football or volleyball, evenings around a fire-pit, playground, space for a future pool, or planting your own fruit trees and garden. Inside, the home features an open floor plan with a desirable split-bedroom layout, offering both functionality and comfort. Enjoy formal living and dining spaces for hosting, plus a spacious family room that flows into the kitchen—perfect for everyday living and gatherings. The kitchen is equipped with abundant cabinetry, hardwood flooring, a breakfast bar overlooking your private backyard. The owner’s suite is a peaceful retreat, featuring French doors leading to the screened back porch, a large walk-in closet, and a spa-style bathroom with soaking tub and separate shower. A flexible fourth bedroom near the primary suite provides the ideal space for a home office, nursery, or hobby room. Step outside and experience true Florida living from your 42’ covered front porch or 34’ screened back porch, surrounded by mature trees and open space. This property offers the perfect balance of cleared land for activities and wooded areas for added privacy. Additional features include: * Remote-operated gate for easy access and security * New roof in 2023 * Side-entry 2-car garage + metal carport * Inside laundry room * Well for irrigation & water softener * High and dry acreage *New AC, Well Pump & Water Heater in 2018 *Septic Pumped 2026 Located just minutes from the Polk Parkway, with convenient access to Lakeland, Tampa, and Orlando, this home combines privacy, land, and accessibility—a rare opportunity in today’s market. If you’ve been searching for a gated acreage property in Winter Haven with no HOA and true outdoor living potential, this one checks all the boxes.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Kimberly Davis (850-625-8855)

Remarks: Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist. The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends luxury with everyday livability. Designed for both entertaining and comfortable living, the open-concept layout showcases luxury vinyl plank flooring throughout, expansive living areas, and a beautifully upgraded chef’s kitchen that serves as the heart of the home. With 4 bedrooms and 4 full bathrooms, the residence provides generous space for family and guests alike. Outdoors, a private pool invites relaxation while remaining surrounded by peaceful, natural views. Adding exceptional value and versatility, the property includes a 1,300 sq ft detached guest house featuring 2 bedrooms and 2 bathrooms, along with an upgraded kitchen and bath—ideal for extended family, long-term guests, or a private work-from-home or creative space. The land itself is what truly sets this property apart. The nearly 11-acre setting offers a thoughtful balance of open usable acreage, mature landscaping, and a scenic private pond, creating a sense of separation and tranquility that enhances both privacy and lifestyle. Multiple outbuildings, including a barn/garage and lean-to structure, provide ample room for storage, hobbies, equipment, or future expansion. In a market where acreage is disappearing and privacy is priceless, properties offering this scale of land, level of renovation, and proximity to town are exceptionally rare. This is not just a home—it’s a private retreat, a long-term asset, and an opportunity to own something truly irreplaceable.

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Brock Jennings (863-990-5846)

Remarks: One or more photo(s) has been virtually staged. Short Sale. Back on the market with renewed opportunity! Enjoy peaceful lakefront living in this beautiful updated 2 bedroom, 2 bath condo located in the gated Winterset community. Featuring an open floor plan granite countertops, stainless steel appliances, upgraded cabinetry, and a cozy breakfast nook, this home offers both comfort and style. The enclosed balcony showcases stunning views of Garden Lake, perfect for quiet mornings or relaxing evenings. Recent updates include plumbing, electrical, lighting, bathroom vanities, and updated flooring throughout, making this home truly move-in ready. Winterset offers resort - style amenities including pool, spa, clubhouse, tennis and pickleball courts, and a private lakefront pier. Conveniently located just minutes from LEGOLAND and under an hour to Orlando attractions. Short sale- priced in alignment with lender expectations. A great opportunity for buyers looking for value, a primary residence, or an investment property.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Valerie Howze (863-604-9080)