Homes For Sale in Winter Haven 33881 - 306 homes

Remarks: BACK ON MARKET — NOW PRICED UNDER $300K! Seller offering a $5,000 buyer closing cost credit. Occupied Winter Haven duplex generating $2,550/month in gross rental income. Both units are 2 bed / 1 bath and feature stone countertops, laminate flooring, and separate living spaces. No carpet. No HOA. No current vacancy. This property offers immediate income from day one with a practical two-unit setup for long-term rental demand. Located in a quiet residential area less than 2 miles from public schools, near Winter Haven’s Chain of Lakes, Lake Shipp Park, public boat ramps, trails, shopping, dining, and approximately 20 minutes from LEGOLAND Florida. Investors looking for an income-producing asset under $300K should take a serious look. Schedule your showing today.

Listing is courtesy of: BANERSY REAL ESTATE, LLC (407-962-6201)

Listing Agent: Enrique Ojeda (321-946-8241)

Remarks: Welcome to 2436 Edwin St NE, Winter Haven, FL 33881(POLK COUNTY). This beautifully designed 4-bedroom, 2-bathroom brand-new manufactured home offers a spacious, open floor plan ideal for modern living. Designed for the modern lifestyle, the spacious open floor plan is bathed in natural light and features durable, high-end vinyl flooring throughout (no carpet!). The massive living room transitions seamlessly into the dining area and kitchen, creating an ideal layout for entertaining. Need extra space? The separate family room provides the perfect footprint for a home office, media room, or playroom. The heart of the home is a chef-inspired kitchen that checks every box: Brand-new stainless-steel appliances, Oversized central island with breakfast bar seating, Stylish shaker-style cabinets with ample storage. The master suite is a private sanctuary, featuring a massive walk-in closet and a luxurious en-suite bath complete with a modern walk-in shower. Three additional generously sized guest bedrooms and a second full bathroom with a soaking tub ensure plenty of room for family and guests. Home also features Sliding Glass door. Enjoy the peace of country living while staying minutes away from Winter Haven’s Chain of Lakes, shopping, dining, and major Central Florida attractions (LEGOLAND, DISNEY, UNIVERSAL STUDIOS). With a dedicated utility/laundry room and a brand-new energy-efficient build, this home is move-in ready and built to last. Schedule your private tour today and experience the best of Florida living! Schedule your private tour today and experience the best of Florida living!

Listing is courtesy of: J&T PROPERTY SOLUTIONS GROUP LLC (863-440-3603)

Listing Agent: Jennifer Daniell (863-440-3603)

Remarks: Welcome to this 2-bedroom, 2-bathroom ground-floor condo in the desirable Lake Buckeye community. This home features a bonus room and includes the washer and dryer for move-in ease. Step inside and enjoy seamless indoor-outdoor living with a cozy open patio off the dining area. The community enhances your lifestyle with amenities such as a sparkling pool, fishing pier, dock all while showcasing tranquil views of Lake Buckeye that make every day feel like a retreat. Ideally located just minutes from Polk State College, Winter Haven Hospital, Bond and Gessler Clinics, and the lively downtown of Winter Haven, you’ll enjoy easy access to dining, breweries, shopping, the farmers market, and seasonal events. Publix and the Diamond plex sports complex are less than 10 minutes away, Legoland Resort is only 15 minutes, and world-class attractions like Walt Disney World and Universal Studios are about an hour’s drive. With leasing permitted and no age restrictions, this property is an excellent choice for both homeowners and investors. Don’t miss your chance to make it yours.

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

Listing Agent: Brian Cox (863-559-3627)

Remarks: Here we go, back to market, Buyer default! The property you are inquiring about is located in Winter Haven, FL, in the Winter Haven Harbour area of Polk County. Now conveniently located is this corner unit with beautiful window views from the third floor, and with recent updates. Two bedrooms, 1 bath, with every square inch utilized for practical purposes. The community is a 55+ and is conveniently located in the heart of convenience. The HOA fees are low by comparison to what is included in the fee. Vacant and ready for occupancy. Text or call for your private viewing. *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: Lakefront living on beautiful Lake Cannon! Wake up every day to sparkling water views and enjoy peaceful sunsets from this charming 2-bedroom, 1-bath waterfront retreat. Perfectly positioned to take advantage of the scenery, the home features a bright and inviting interior with a spacious living area and an oversized picture window that frames the lake like artwork. Natural light pours in, creating a warm and cheerful atmosphere throughout. Outside, enjoy the easy Florida lifestyle with plenty of yard space, covered parking, and direct lakefront access on one of the most desirable lakes in the Winter Haven Chain of Lakes. Whether you love boating, fishing, kayaking, or simply relaxing with your morning coffee while taking in the view, this property delivers. A rare opportunity to own affordable lakefront in Central Florida—ideal as a full-time residence, winter getaway, or investment property. Bring your boat, bring your fishing pole, and start enjoying life on Lake Cannon!

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

Listing Agent: Michele Elchin (863-514-6880)

Remarks: Come see 1100 Carefree Cove Dr, recently improved with a new roof, fresh exterior paint, and fresh interior paint, presenting a comprehensively refreshed presentation. Partial flooring replacement further updates the interior living spaces, while a fenced in backyard provides practical outdoor areas. This property embodies a fresh approach to comfortable living. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Welcome to this spacious and recently upgraded home sitting on a rare 0.40-acre corner lot with NO HOA and NO CDD, giving you the freedom and space you’ve been looking for. Major recent improvements include updated HVAC, electrical, and plumbing systems for added peace of mind, along with attractive interior upgrades featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary tile finishes. The oversized lot offers endless possibilities and plenty of room to park your RV, boat, jet ski, work vehicles, or recreational toys worry-free — something hard to find in today’s market. Conveniently located near major supermarkets, restaurants, schools, and main roads for easy commuting, this property is ideal for homeowners seeking space and flexibility or investors looking for a strong opportunity. Schedule your private showing today and discover the value, freedom, and potential this unique property has to offer!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Jose Hooker-Gomez (407-272-6986)

Remarks: Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive, you’re welcomed by a handsome paver driveway that adds both charm and curb appeal. Step inside to soaring vaulted ceilings and an open-concept floor plan, ideal for both everyday living and entertaining. Expansive living and dining areas flow effortlessly, creating a bright, airy feel throughout the home. The oversized primary suite, located just off the main living area, is a true retreat. It features a luxurious en suite bathroom complete with a large soaking tub, separate walk-in shower, dual sinks, and a spacious walk-in closet. Fresh interior paint gives the home a crisp, updated look, and a new roof provides added peace of mind. A private office offers the perfect space to work from home or can easily flex to fit your lifestyle. This home is situated just a short distance away from the community pool and hot tub. This one checks all the boxes!

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

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

Remarks: One or more photo(s) has been virtually staged. Waterfront view from your porch. Affordability, low-maintenance comfort, & strong rental income potential. Waterfront view from your porch. Discover serene living at this charming 2-bedroom, 2-bathroom condo offering stunning sunset water views from its screened lanai. The home has a functional layout, it includes a combination of living & dining area, a large master suite with a walk-in closet, & a sliding glass door towards your comfortable back porch overlooking the canal water view; the kitchen has sufficient space; & there is a large storage room. Enjoy your Florida lifestyle, this welcoming community with built-in amenities, has direct lakefront access via a community dock for boating, fishing, and water sports on the connected Chain of Lakes. For only $253 a month, HOA covers your home's exterior maintenance. Location is accessible to nearby shopping, hospitals, medical offices, schools, and about an hour drive Tampa or Orlando. To schedule a showing, provide your realtor your pre-approval letter or proof of cash funds. At this price range, this move-in ready condo is your best choice.

Listing is courtesy of: MAZELG REALTY (863-399-0226)

Listing Agent: Lienyvette Grimaldo (863-399-0226)

Remarks: New Price and $2500 Seller Credit!! Relocating to Florida? This pristine 5-bedroom, 3-bath home offers nearly 2,700 square feet of thoughtfully designed living space in the heart of Central Florida, providing the space, flexibility, and value many buyers from northern states and high-cost markets are seeking. Priced at $374,900—approximately $140 per square foot—this home delivers exceptional value compared to similar properties in California and many northern metro areas. The well-planned layout includes five true bedrooms, three full bathrooms, and a versatile flex space that could easily be converted into a sixth bedroom. This additional space makes the home ideal for growing families, multigenerational living, aging parents, young adults living at home, or a private home office or hobby room. A guest suite on the first floor adds even more functionality and convenience. The main living areas feature upgraded tile flooring, while the kitchen is finished with granite countertops and ample workspace for everyday living and entertaining. The home has been meticulously maintained and is in pristine, move-in-ready condition. Outdoors, enjoy added privacy with no rear neighbors, creating a peaceful and open backdrop rarely found in newer communities. Located just 5 minutes from downtown Winter Haven, residents enjoy easy access to historic charm, the Ritz Theatre, Saturday farmers markets, a beautiful public library, and a growing selection of high-end and locally owned dining options. A brand-new Publix grocery store is currently under construction within walking distance, adding everyday convenience and long-term appeal. The community features a very low HOA and no CDD fees, helping keep ownership costs manageable—an important advantage for relocating buyers. Ideally positioned just 5 minutes from Legoland Florida and approximately 30 minutes from Disney, the home offers access to Central Florida attractions while maintaining a comfortable residential setting. With generous square footage, flexible living spaces, privacy, and proximity to downtown amenities, this home is an outstanding opportunity for buyers ready to trade cold winters or high housing costs for a more flexible and comfortable Florida lifestyle.

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. Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. Roof 2020 - - Repipe 2025 - The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Daniel Araque (321-276-0747)

Remarks: Welcome to 255 Haines Boulevard, Winter Haven, Florida! This beautifully maintained home offers the perfect blend of comfort, convenience, and Florida living. Featuring a spacious floor plan with plenty of natural light, this property is ideal for families, first-time homebuyers, or investors alike. The kitchen provides ample cabinet and counter space and flows seamlessly into the living and dining areas, making it perfect for entertaining guests. Step outside and enjoy the generous yard with room for outdoor activities, gardening, or future enhancements. Conveniently located near shopping, dining, schools, medical facilities, and major roadways, this home provides easy access to everything in Winter Haven. Whether you're looking for a primary residence, seasonal home, or investment property, this move-in-ready opportunity is one you won't want to miss. Schedule your private showing today!

Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)

Listing Agent: Sean Denney (863-602-0424)

Remarks: ***SELLER'S ARE VERY MOTIVATED DUE TO JOB TRANSFER***Welcome to this updated 4-bedroom, 2.5 bath Winter Haven home! This home offers modern living, featuring new flooring, appliances, new windows with pull-out panes for easy access and cleaning along with new Plantation Shutters on all windows! You will also enjoy the stylish bathroom/kitchen renovations featuring in the kitchen beautiful backsplash and new pantry door, new tile in guest bath and new shower in primary bathroom! Centrally located near Legoland, shopping, and all your medical facilities, the property includes a new fenced back yard and new storage shed, HOA/City approved.

Listing is courtesy of: STACEY TOWNS REALTY LLC (863-422-1585)

Listing Agent: Cathy Stripling (863-422-1585)

Remarks: Experience elevated living in this beautifully maintained 3 bedroom, 2 bathroom residence located in the highly desirable Country Walk community in Winter Haven. Designed with style and comfort in mind, this home showcases custom luxury finishes throughout the living room and bedrooms, creating an elegant and inviting atmosphere. The open concept layout offers the perfect blend of functionality and sophistication, while the modern kitchen serves as the centerpiece of the home with sleek cabinetry, quartz countertops, and ample space for cooking and entertaining. The spacious primary suite provides a private retreat with a walk in closet and a beautifully appointed bathroom. Step outside and enjoy the extended paver patio, an ideal space for relaxing or hosting family and friends, all enclosed by a white PVC privacy fence that enhances both comfort and privacy. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this home is also just minutes from LEGOLAND Florida Resort and many of Central Florida’s most popular attractions. Combining stylish interior design, exceptional outdoor living, and a prime location, this residence offers an outstanding opportunity to enjoy the best of the Florida lifestyle.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Maria Santacruz (407-552-8213)

Remarks: Fall in love with this stunning 5-bedroom, 3-bath home with a 3-car garage, perfectly situated on one of the largest lots in the neighborhood. Combining luxury, comfort, and functionality, this spacious home offers an open-concept layout with split bedrooms for added privacy, creating the perfect balance of space and efficiency. The heart of the home is a bright, wide-open living area flowing into a stunning gourmet kitchen featuring a massive island, 42-inch upper cabinets, a large pantry, and top-of-the-line stainless steel appliances. Whether you’re relaxing, entertaining, or cooking, this home offers endless space to move and gather. High-end finishes are showcased throughout, including quartz countertops in the kitchen, luxury tile flooring in the main living areas, premium carpeting in the bedrooms, crown molding, and elegant window shutters. This is more than just a home, it’s an investment, with over $60,000 in upgrades available for review. For added comfort and convenience, the home includes a water softener system and reverse osmosis filtration. Step outside to your private outdoor retreat featuring an oversized screened-in lanai, summer kitchen, and a fully fenced backyard on an expansive lot, perfect for enjoying the Florida lifestyle year-round. Located in a quiet, peaceful Polk County community near Highway 27, you are just a short drive to Disney, Orlando International Airport, shopping, dining, and more. Best of all, there are NO CDD fees and a low HOA. This home is being sold AS IS and is truly move-in ready. Schedule your private showing today!

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

Listing Agent: Deep Mehta, Pa (407-702-7029)

Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,625 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. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

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

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

Remarks: Discover this stunning 2023-built home in the growing Lucerne Park area of Winter Haven, offering the perfect blend of space, comfort, and modern design. Situated on an oversized lot, this 4-bedroom, 3-bath home with a 3-car garage features over 3,000 square feet of living space with an open and functional floor plan ideal for entertaining and everyday living. The large kitchen overlooks the main living area, creating a bright and welcoming space for gatherings. The spacious primary suite features a walk-in closet and private bathroom, while the additional bedrooms provides flexibility for family, guests, or a home office. Enjoy the oversized backyard with plenty of room to relax, entertain, or create your dream outdoor oasis. Conveniently located near shopping, dining, schools, and just minutes from LEGOLAND Florida Resort, this move-in ready home is a fantastic opportunity in one of Winter Haven’s growing communities.

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

Listing Agent: Jessica Delgado (407-520-0159)

Remarks: This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and a large backyard—ideal for entertaining or relaxing outdoors. This home is light and bright and move-in ready just for you! The kitchen features white raised-panel PVC cabinetry, black tile countertops, a closet pantry, and updated appliances including a refrigerator (2026) and stove (2022). Major system upgrades include a new 3.5-ton A/C system with new ductwork and a roof replaced in 2022. The split-bedroom layout offers privacy, with both bathrooms very nicely updated. The spacious primary suite includes a beautiful bath with stone floors, a quartz vanity with integral sink and wall-mounted faucet, and a walk-in shower with new tile, glass doors, and drain pan—part of a $15,000 renovation. Additional highlights include a garage with mini-split A/C, insulated garage door, pull-down ladder for attic access, washer/dryer hookup, and laundry sink. Outside you will have a 10’x12’ shed with electric, and a well house with a Culligan water softener system. A new black aluminum fence surrounds the property, with vinyl PVC privacy fencing along the left side, 12-foot gates on both sides plus a 6-foot front gate—perfect for storing a boat, RV, or extra vehicles. A covered rear carport adds even more flexibility. Conveniently located on a large corner lot near lakes, parks, recreation areas, LEGOLAND, Hwy 27 & I-4, and all that Central Florida has to offer. Welcome home!

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

Listing Agent: Russ Rhoads (863-604-1570)

Remarks: One or more photo(s) has been virtually staged. Short Sale. Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, offering 1,512 square feet of comfortable living space in a desirable gated community in Winter Haven. Built just two years ago, this nearly new home blends modern design with a warm, family-friendly feel. Step inside to find vaulted ceilings and tile flooring throughout the main living areas, creating a bright and open atmosphere. The spacious kitchen features stainless steel appliances, a large island, and ample cabinet space, perfect for everyday living or gathering with friends and family. The split floor plan provides privacy, while the generous primary suite includes double sinks, a garden tub, separate shower, and walk-in closet. Enjoy Florida living outdoors on the covered lanai, with a backyard perfect for relaxing afternoons or weekend playtime. Conveniently located near Downtown Winter Haven, Polk State College, Winter Haven Hospital, shopping, dining, and major attractions like LEGOLAND. For those who love lifestyle and entertainment, the home is also just about 15 minutes from the popular Port 27, a vibrant waterfront destination known for its live music, great food, desserts, and beautiful lake scenery—the perfect place to unwind and enjoy time with family and friends. This move-in ready home offers comfort, style, and location all in one. Schedule your showing today!

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

Listing Agent: Carolina Flores, Llc (954-471-5909)

Remarks: Welcome home to Brenton Manor! This move-in ready 3-bedroom, 2-bathroom split-plan home checks every box — and then some. The open-concept kitchen flows seamlessly into the great room, creating the perfect space for entertaining or relaxing after a long day. Step outside to your private, fully fenced backyard with no rear neighbors — your own Florida oasis. Big-ticket updates have already been done for you: brand-new 2026 HVAC with UV ray lights and professionally cleaned ductwork, 2026 whole-home water softener system, 2025 tankless water heater, 2025 fresh exterior paint, 2025 gutters, and a 2023 roof. Both bathrooms feature updated showers, so all you need to do is move in and enjoy. Conveniently located near top medical facilities, BayCare Winter Haven Hospital just minutes away, and the nationally recognized Lakeland Regional Health nearby. Everyday conveniences are just as close, with shopping, dining, and retail options all within a short drive. Ideally located for commuters and travelers, this community offers. Ideally located for commuters and travelers, this community offers quick access to Interstate 4, the Polk Parkway (SR-570), and US-27—placing Tampa and Orlando approximately 30 to 40 minutes away and the world-famous theme parks just 35 miles away. Schedule your private showing today!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Cynthia Davis (407-619-2937)