Homes For Sale in Winter Haven 33880 - 234 homes

Remarks: New - New - New! This 3 bedroom 2 bath features a beautiful lake view and has been completely remodeled. Updates include a new HVAC system, new metal roof, new kitchen with granite counters, new bathrooms, new flooring, and new septic system. No HOA means you can store your boat. Can be purchased together with 73 High Street to make a family compound or have an income producing property. (MLS P4937859)

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

Listing Agent: Dwight Head (863-965-0207)

Remarks: Welcome to the heart of Winter Haven — famously known as the Chain of Lakes City! This charming, established neighborhood offers NO CDD fees, a very low annual HOA, and the kind of character you simply won’t find in new construction communities. Major updates have already been completed, including a NEW ROOF (2022), NEW FLOORING (2024), a beautifully renovated primary bathroom, and fresh interior paint throughout. Inside, the home is filled with natural light and features a comfortable, functional layout designed for everyday living. Step outside to a peaceful backyard highlighted by a large mature shade tree that adds privacy, character, and the perfect setting for relaxing, entertaining, or enjoying Florida evenings outdoors. Unlike many new construction options with higher monthly fees and smaller lots, this home delivers affordability, long-term value, and lower carrying costs — all in a well-established community. Conveniently located near shopping, dining, schools, medical facilities, and major highways, it also offers an easy commute to both Tampa and Orlando. Homes with NO CDD, low HOA, and major updates already completed are becoming increasingly rare in today’s market. Whether you’re a first-time buyer, downsizing, investing, or simply looking to enjoy the Florida lifestyle near Winter Haven’s famous chain of lakes, this is an exceptional opportunity at an accessible price point.

Listing is courtesy of: MARZUCCO REAL ESTATE (813-679-1365)

Listing Agent: Vicki Carden (813-340-4563)

Remarks: Welcome to this stunning 4-bedroom, 3-bath split floor plan home with tile flooring throughout. The open kitchen features a breakfast bar, brand-new stainless steel appliances, and plenty of storage. You’ll love the formal living room and a dedicated laundry room. Sliders from both the master suite and living room lead to a peaceful lanai. The master bath boasts dual sinks, a garden tub, and a separate shower. Plus, one of the bathrooms conveniently opens to the lanai. The lanai floor and garage floor was recently painted for that added style. The home is located in Winter Haven in between Orlando and Tampa close to all of the amenities you would need. Don’t miss this gem!

Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)

Listing Agent: Annie Wood (321-229-1913)

Remarks: This home is a must see!! Very well maintained home located in Village Park, a 55+ community where dogs are allowed. The home features new thermal efficient windows and all new plumbing. The vapor barrier is also new. The kitchen is very open and functional. The living room is comfortable and inviting. The primary bath has a new vanity and the bedroom carpet is new. Plus, the laundry is located inside a closet in the hall bath. The vaulted ceilings give the feel of spaciousness. Outside you will find a double shed which opens to the the front and back. Sit on the front porch and enjoy your morning coffee or evening cocktail. The community features a clubhouse, pool, and shuffleboard. There are many activities available, or you can just sit back and enjoy the peaceful community. This home is a must see!

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

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

Remarks: NO LOT RENT. Welcome to your slice of Florida living in Winter Haven! This well-maintained 2-bedroom, 2-bath home offers 1,620 sq ft of comfortable living space and is packed with valuable upgrades, including the ROOF 2023 and 4 ton A/C 2023, Water Heater 2024 or 2025, water softener, reverse osmosis system, and rain gutters with leaf guards for added peace of mind. Step inside to find a spacious floor plan. Relax and unwind in the large screened-in lanai, ideal for enjoying Florida’s beautiful weather year-round. The property also features a large storage shed with air conditioning, giving you plenty of room for tools, hobbies, or seasonal items and an inside laundry with washer and dryer included. Located in the desirable Village Park community for those 55+ years young, residents enjoy an incredibly low HOA fee of just $55 a month, which includes access to a sparkling pool and community amenities. Best of all—you own the land! Limited trailer/RV storage is also available on a first-come basis. Perfectly situated between Tampa and Orlando, this home offers convenient access to world-renowned attractions like LEGOLAND Florida Resort, Walt Disney World, Universal Studios Florida, Busch Gardens Tampa Bay, ZooTampa at Lowry Park, and Seminole Hard Rock Hotel & Casino Tampa. You’re also just minutes from shopping, dining, grocery stores, hospitals, golf courses, nature parks, and Florida’s beautiful beaches. With both Tampa and Orlando international airports within about an hour’s drive, travel is incredibly convenient. Whether you're looking for a full-time residence or a seasonal retreat, this home checks all the boxes. Don’t miss your opportunity to live in Village Park—schedule your private showing today!

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

Listing Agent: Carolyn Christian, Llc (863-514-6378)

Remarks: Charming and well maintained! 2-Bedroom 2- Bath Home in Desirable 55+ Community – You Own the Land with low HOA fees! This inviting home features fresh interior and exterior paint and a newly screened-in front porch, perfect for enjoying your morning coffee, afternoon tea or just relaxing in the Florida breeze. The property also offers a fenced-in backyard, ideal for pets to play or gardening. Additional highlights include a one-car carport and a spacious 22x11 workshop/storage area, providing plenty of room for hobbies, tools, or extra storage. Residents enjoy access to a community clubhouse and sparkling pool, perfect for socializing and staying active in this welcoming neighborhood. Conveniently located near shopping, dining, and local amenities, this home offers both comfort and convenience. Don’t miss this opportunity to own an affordable home with land ownership in a vibrant 55+ community!

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

Listing Agent: Michelle Armbruster (863-521-6879)

Remarks: Under contract-accepting backup offers. Welcome to 8 The Village Blvd—nestled in a highly desirable gated community in Winter Haven with exclusive access to beautiful Spirit Lake! This well-maintained former model home offers 3 bedrooms, 2 baths, and a 2-car garage, combining comfort, style, and thoughtful upgrades throughout. Step inside to an inviting open floorplan featuring gleaming wood floors, a formal dining area overlooking the spacious front yard, and a stunning magnolia tree that enhances the home’s curb appeal. The kitchen is designed to impress with Corian countertops, upgraded appliances, and abundant cabinet and counter space, flowing seamlessly into a bright breakfast nook with views of the backyard and large screened lanai. The split-bedroom layout provides privacy, with two generously sized guest bedrooms and a full bath (with lanai access) tucked away on one side of the home. The spacious primary suite is located on the opposite side and features sliding glass doors to the lanai, dual walk-in closets, and a luxurious en-suite bath complete with a garden tub, separate shower, and ample counter space. Major updates offer peace of mind, including a new roof (May 2023), upgraded 50-gallon water heater (2021), new garage door opener (2022), upgraded main electrical panel (2024), and a Brinks Home Security System and Goodman AC (2025) with transferable warranty. The 2-car garage includes a Chamberlain opener (2022), built-in shelving, and a pegboard—perfect for organization. Enjoy all the amenities this sought-after gated community has to offer, including a clubhouse, recently refinished pool, tennis and basketball courts, updated exterior lighting, and a freshly painted entrance and clubhouse. Residents also enjoy private access to Spirit Lake via a boat ramp and dock. This move-in-ready home is truly “neat as a pin” and ready for its next owner. Survey and floorplan available—schedule your private showing today!

Listing is courtesy of: HOUWZER INC (267-765-2080)

Listing Agent: Daniel Robinson (904-447-8922)

Remarks: This property NOW INCLUDES 20 STORAGE UNITS and nearly 3 acres of land, creating a truly rare lakefront development opportunity within the Winter Haven Downtown CRA District. Enjoy beautiful views of Lake May with direct access to the Winter Haven Chain of Lakes — a prime location for growth and investment. Current DOR use code (0852) permits duplexes, triplexes, and quadplexes — up to 9 units — throughout the Polk City, Auburndale, Lake Alfred, and Winter Haven areas. The property also features a 1,208 sq. ft. concrete block structure built in 1955, offering additional utility or potential for redevelopment. The value lies in the land, location, and flexibility of use. Possible future options include multi-family housing, office/professional, or light industrial projects (subject to approvals). Conveniently close to downtown Winter Haven’s shopping, dining, parks, and major roadways, this site is positioned perfectly for future growth. A rare opportunity to invest, develop, or hold in one of Central Florida’s fastest-growing markets.

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

Listing Agent: Veronica Bard (863-670-7526)

Remarks: One or more photo(s) has been virtually staged. Welcome to maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. This 3rd floor 2-bedroom, 2-full-bath condo offers the relaxed lifestyle many buyers look for, complete with elevator access for easy entry. You are greeted by views of the community pool and cabana area right from your front entrance, while the interior features a bright Florida Room and a relaxed lakeside atmosphere. Best of all, the monthly HOA fee covers everything except your electric bill, making your budget completely stress-free. Enjoy premier amenities like a private boat ramp and fishing pier right on Winter Haven's popular Chain of Lakes. Located just across the water from downtown shopping and dining, this well-established, owner-occupied neighborhood is ready to welcome you home to a truly wonderful community lifestyle!

Listing is courtesy of: REGAL REAL ESTATE LLC (863-660-7927)

Listing Agent: Natalie Elson (863-709-3516)

Remarks: Under contract-accepting backup offers. Fully remodeled two story 4 bedrooms 3 bathrooms home featuring a modern neutral color palette, white cabinets, vinyl plank flooring throughout, and brand new stainless steel appliances. Bright and updated interior with a clean contemporary feel. Move-in ready and designed for low-maintenance living.

Listing is courtesy of: NUMBER ONE CHOICE REALTY CORP (352-404-5638)

Listing Agent: Daulis Webb Gagnon (407-234-9789)

Remarks: Seller will entertain any reasonable offer!!** Beautiful 3-bedroom, 2-bath ranch home built in 2022 offering modern design and easy one-level living. Open concept layout with spacious living areas, contemporary finishes, and abundant natural light. Well appointed kitchen and comfortable bedroom split for added privacy. Move-in ready and perfect for today's lifestyle.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: Under contract-accepting backup offers. Don’t miss your chance to own this fully rented quadplex offering immediate cash flow. All four units are currently occupied with month-to-month tenancies paying $1200 per month, giving a new owner flexibility to increase rents to market value or renovate units for added equity and higher returns. Each unit features: 2 Bedrooms / 1 Bathroom, spacious living and dining room combination, dedicated laundry room with washer/dryer hookups, gas stoves and hot water heaters. The roof is only 5 years old. Whether you’re looking to expand your portfolio or secure a strong income-producing property, this quadplex checks all the boxes with built-in upside potential.

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

Listing Agent: Harold Baker (863-604-6272)

Remarks: Come check out this like-new 4-bedroom, 2-bathroom home with unbeatable value, priced to sell under $300k! If that's not enough, this newer community has absolutely NO CDD fees and a very low HOA, making this a great starter or investment home. Get instant equity on day one! Watch gorgeous sunsets over the water right from your private, covered lanai, and fully Fenced back yard with a high-quality, durable metal fence. Inside, this meticulously maintained home features the highly sought-after open-concept Valeria floor plan, complete with a spacious 2-car garage, contemporary kitchen finishes, sleek solid-surface quartz countertops, and included appliances. The large primary suite is tucked away for ultimate quiet, featuring an oversized walk-in closet and a dual-vanity bath. Located in a pristine, quiet community just minutes from Legoland, top schools, and major roadways. Turn-key, and priced for an immediate sale—schedule your private tour today.

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

Listing Agent: Richard Rung (727-272-0267)

Remarks: The property you are inquiring about is located in Winter Haven, FL in the Emerald Acres/Grassy/Lake Estates area of Polk County. This beautiful lakefront, 4+ bedrooms, 2-bath home is situated on over 2 acres on Grassy Lake! Just needs a little TLC and a new owner to enjoy a relaxed lifestyle with a beautiful view! Call, text, and see! *Agents, please read MLS Remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Under contract-accepting backup offers. Short Sale. MAKE AN OFFER ON This better than new construction stunning 4-bedroom, 3-bathroom home is just 2 years young and beautifully maintained—ready for you to move right in! Step into a bright and spacious open-concept layout featuring luxury vinyl flooring throughout, soaring high ceilings, and a seamless flow between the living room and kitchen. The kitchen boasts elegant cabinetry, sleek countertops, and modern finishes. Energy-efficient solar panels help keep utility costs low, and the property is fully enclosed with a new vinyl fence for added privacy. The master suite offers a spacious walk-in closet and a spa-like bathroom complete with an extended walk-in shower, dual sink vanity, and a dedicated towel closet. A second bedroom features its own private ensuite, while a third full bathroom is ideal for guests or inlaws. Relax in your fenced in back patio and enjoy the peace and privacy of your surroundings. Conveniently located near shopping where more stores are being built like a new Target, dining, hospitals, schools and top Central Florida attractions—Legoland is 15 minutes away--this home has it all and more. Don’t miss the opportunity to make it yours!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Marisol Rivera (407-607-5201)

Remarks: Under contract-accepting backup offers. PRICE REDUCTION!!! MOTIVATED SELLER!!! Discover this exceptional income-producing property perfectly situated on a spacious 0.48-acre lot in the heart of Winter Haven. This versatile property features two separate living spaces, one currently rented—providing immediate income and excellent long-term investment potential. The main home which is now vacant and ready for it's new owners or tenants offers 3 bedrooms and 2 bathrooms, including a generous master suite with an en-suite bath. The open and functional layout makes it ideal for families or long-term tenants. Attached to the main residence is a 484 sq. ft. in-law suite currently rented, complete with a full kitchen, bedroom, bathroom, and private entrance. This flexible space can serve as an additional rental unit, private guest quarters, or be seamlessly integrated into the main living area for multi-generational living. This home was recently appraised above the asking price, giving buyers instant equity and outstanding value. Whether you’re an investor seeking steady cash flow or a homeowner looking for flexibility, this property is a rare find. Take advantage of strong rental demand, potential appreciation, and the benefits of owning in one of Florida’s fastest-growing counties, consistently rated among the best places to live. Don’t miss your chance to own this unique multi-unit property—schedule your private showing today!

Listing is courtesy of: BRIGHT REALTY (941-552-6036)

Listing Agent: Jen Victor (941-587-2787)

Remarks: Looking for the perfect starter home or turnkey investment? Welcome to 117 4th Ave N! This well-maintained 3-bedroom, 1.5-bath home has been lovingly cared for by the same family for over 40 years and is now ready for its next chapter. Situated just minutes from shopping and dining, this property delivers both comfort and convenience in the heart of Winter Haven. Recent updates include a brand-new roof (2025), providing peace of mind and long-term value. For investors, current tenants are interested in staying—offering an immediate income opportunity if desired. Inside, you'll find an open and inviting floor plan where the kitchen flows seamlessly into the spacious living room. Each bedroom offers generous space with nice-sized closets, perfect for growing families or long-term renters. But here's the bonus: attached to the back of the home is additional flex space not included in the square footage. This area could easily be converted into a 4th bedroom, mother-in-law suite, home office, or studio—adding even more value and versatility to the property. Parking is another standout feature with a covered carport plus a detached garage—ideal for extra vehicles, storage, or workshop space. Priced to sell and brimming with potential, this gem won't last long.

Listing is courtesy of: FIVE STAR REAL ESTATE OF FLORIDA LLC (904-539-3336)

Listing Agent: Arina Reid-Martin (770-500-0514)

Remarks: Welcome to this spacious 3-bedroom, 2-bathroom home located in the desirable Winter Haven area. This residence offers a great floor plan with plenty of natural light, a kitchen with ample storage, and a layout ideal for both everyday living and entertaining. The owner’s suite features a private bath and walk-in closet, while the three additional bedrooms provide flexibility for family, guests, or a home office. The property is conveniently situated near major Central Florida attractions, including LEGOLAND Florida Resort, and is just a short drive from Walt Disney World and Universal Orlando Resort. Residents will also enjoy proximity to shopping at Posner Park Village, diverse dining options, and excellent medical facilities such as BayCare Winter Haven Hospital. For outdoor enthusiasts, nearby Lake Eloise, Chain of Lakes Park, and Bok Tower Gardens brings ample recreation and leisure opportunities. With its prime location and easy access to highways connecting Orlando and Tampa, this property offers the perfect combination of comfort and convenience. Don’t miss the opportunity to make this beautiful Winter Haven home yours. Roof (2017) Water heater (2025)

Listing is courtesy of: OAK AVENUE REAL ESTATE LLC (407-720-5000)

Listing Agent: Vivian Ortiz (863-514-7641)

Remarks: Charming and well-maintained home in Winter Haven featuring gorgeous wood flooring throughout the main living areas and porcelain ceramic tile in the kitchen. The beautifully updated kitchen features stainless steel appliances, a gas stove, soft-close cabinets, and ceramic tile flooring, offering both style and functionality. The front enclosed sunroom is filled with beautiful natural morning light through surrounding windows, creating the perfect space to relax, enjoy your coffee, or unwind throughout the day. Conveniently located near several beautiful lakes; including Lake Howard, this property offers the best of Florida living while being situated in a FEMA-designated dry zone outside of the flood area for added peace of mind. Enjoy major energy savings with the fully paid-off solar panel system already in place, helping keep electric bills low for the new owner. Additional updates include a newer roof and AC system, along with a full-house gas generator capable of powering the entire home during storms or outages with the flip of a switch. The spacious backyard workshop provides ample room for tools, hobbies, storage, or workspace needs. Conveniently located near shopping, dining, parks, and recreational opportunities, this property is ideal for buyers seeking comfort, efficiency, preparedness, and functionality all in one. Schedule your private showing today!

Listing is courtesy of: SOUTHERN PINE REALTY GROUP, LLC (813-525-7313)

Listing Agent: Elda Romero (813-957-1212)

Remarks: Under contract-accepting backup offers. Welcome home to 541 Adriel Avenue — where Florida living meets wide-open space. Set on an expansive 0.69-acre estate-style lot, this 4-bedroom Florida ranch offers a rare combination of privacy, square footage, and modern peace of mind. Step through the arched entry into a sun-filled great room with soaring vaulted ceilings, elegant archways, and a thoughtfully designed open floor plan. The kitchen features rich granite countertops, stainless steel appliances, oak cabinetry, and a center island built for entertaining. The primary suite includes a private bath with a garden soaking tub and separate walk-in shower. Beyond the formal dining room, French doors open to a generous Florida room with a full secondary kitchen — granite counters, gas range, and abundant cabinetry. The fully fenced backyard backs to open land with no rear neighbors, offering room for RVs, trailers, or future expansion. New roof and AC in 2025. USDA-eligible. Schedule your private showing today.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Javier Herrera Jimenez (863-259-9010)