Homes For Sale in Winter Haven 33881 - 281 homes

Remarks: One or more photo(s) has been virtually staged. This Fully Renovated Gem is ready to go! New Roof at Closing! This beautifully renovated 3-bedroom, 2 bathroom home in Winter Haven, Florida, offers modern living in a serene neighborhood near shopping and seasonal markets. The open-concept layout features a spacious living area, a new kitchen with brand-new stainless steel appliances, and stylish finishes throughout. Each bedroom is generously sized, with the master suite boasting a luxurious walk in Closet. The home also includes a cozy backyard, perfect for relaxation and large shed. Located in a quiet neighborhood, this home combines comfort, convenience, and contemporary charm, making it the perfect place to settle down.

Listing is courtesy of: ALIGN RIGHT REALTY LLC (727-264-6800)

Listing Agent: Austin Williams (516-782-1553)

Remarks: Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, and unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses and open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway and an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Lakefront living with a proper sunset! Down a private road with no HOA (because your house shouldn't come with a rule book). This renovated home offers direct frontage 80' on Lake Pansy and a bonus 80' of canal frontage across the street. The property provides excellent water access and endless sunset views. Outside is where this home really shows off with amenities including a heated saltwater pool / lap pool with markers on the bottom, lighting and water features, added style with a surfboard outdoor shower, screened in with panoramic panels because this view deserves center stage. The outdoor summer kitchen is outfitted with a refrigerator, table top ice chest, bar area, and a grill supplied by a 99-gallon propane tank, making it well-suited for entertaining all year round. The lanai is glassed in with cedar tongue and groove ceiling wrapped with motorized retractable sunshades, while enhanced landscape lighting and mature palm trees set the tropical tone. Additional exterior upgrades include a composite dock, fenced in yard, seamless gutters with leaf filters, and recently replaced garage and front entry doors. Inside, the vibe continues with an electric fireplace with customizable lighting (because ambiance matters). Live-edge floating shelves with integrated lighting adds a designer touch. Double-pane replacement windows, custom drapes, California Closets, luxury vinyl and ceramic tile throughout, laundry closet for added convenience. The kitchen brings the function and the flair with an island, generous storage, new cabinetry, quartz countertops, a natural gas range with hood ventilation, along with a built in microwave, electric oven, and refrigerator/freezer. Culligan water treatment. The roof and HVAC system are approximately 10 years old. Additional features include LRE foundation improvements, and well-fed irrigation. Prewired generator hook-up installed in garage. The boat ramp is located on the west side of lake Pansy. Conveniently Located 20 minutes from Lego Land, 7 minutes from Publix Super Market, 5 minutes to Home Depot, 3 minutes to the nearest boat ramp to access the Winter Haven Chain of Lakes. This is a rare opportunity to own a turnkey lakefront property with endless sunsets, extensive upgrades, and no HOA restrictions.

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

Listing Agent: Olivia Boggs

Remarks: Under contract-accepting backup offers. This Beautiful 4-bedroom,3-bath home with additional office offers the perfect blend of style and comfort. Featuring hardwood floors and tile throughout the main living areas, cozy carpeted bedrooms, and an open floor plan with high ceilings that fill the home with natural light. The kitchen boasts elegant granite countertops, while the renovated master bathroom showcase a huge glass shower, double vanity sinks and solid surface countertops. Step outside to your backyard oasis with a gorgeous Pool and Jacuzzi, complete with stone Pebble Tec finish - perfect for relaxing or entertaining. Outside also includes a well for lawn watering & landscape lighting. Enjoy the added bonus of a community pool and clubhouse. Conveniently located near downtown Winter Haven with easy access to Tampa and Orlando, this home truly has it all. Call today for your private showing!!!

Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)

Listing Agent: Cindy Thornton (863-287-8223)

Remarks: Beautiful 3BR/2BA home in desirable College Grove, just off Lake Elbert with its new walking trail. Prime location (with NO HOA) close to downtown Winter Haven, shopping, hospitals, and Polk State College Open floor plan with separate living, dining, and family room featuring cathedral ceilings and a gas fireplace. Updated kitchen with island, breakfast bar, granite countertops, stainless appliances, recessed lighting, and closet pantry. Split bedroom plan for added privacy. Spacious primary suite with walk-in closet, dual sinks, and tub/shower combo. French doors from primary bedroom, living, and family rooms lead to screened lanai with spa and waterfall—perfect for relaxing or entertaining. New Roof 2021. NEW AC 2020. Additional features include luxury vinyl flooring throughout, walk-in closets in all bedrooms, tankless water heater, and irrigation system. Situated on a .30-acre fenced lot with plenty of room for outdoor activities. Schedule your showing today!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Under contract-accepting backup offers. Welcome to this well-located single-family home situated on a quiet cul-de-sac in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 3 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living. 2 car garage and a large driveway. Newer Shingle Roof 2023. Inside, the living area provides a straightforward, open flow into the dining space and kitchen, making it easy to stay connected whether you’re relaxing at home or hosting guests. The bedrooms are nicely sized, and the two full bathrooms add convenience and functionality. Out back, you’ll find a fully fenced backyard that offers privacy and room to enjoy the outdoors. The covered lanai is a great spot for casual outdoor seating, weekend barbecues, or simply spending time outside regardless of the weather. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.

Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)

Listing Agent: Gabriel Silva Andrada (321-666-0301)

Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!

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

Listing Agent: Casandra Vann (863-546-5446)

Remarks: Beautiful two-story single-family home built in 2023. Featuring a modern and functional design, this home offers 5 bedrooms and 3 full bathrooms, spread across 2,284 square feet of living space. The ground floor includes a spacious living room, a kitchen equipped with modern appliances (refrigerator, washer, dryer, dishwasher, and more), and a bedroom with a full bathroom, ideal for guests or as an office. The second level features the remaining bedrooms, including the master suite, which is equipped with a walk-in closet. Interior finishes feature ceramic and carpet flooring, thermal windows with blinds, and a central electric HVAC system. The property includes an attached two-car garage and sits on a 5,500-square-foot lot. Located in the Canton Park community, with low HOA fee and not CDD. This home represents an excellent opportunity for those seeking comfort and style in a prime location close to Tampa, Orlando and Lakeland. More pictures coming soon.

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Brigida Lopez (321-945-3989)

Remarks: 55+ PLUS COMMUNITY! Corner unit! Features granite countertops, marble kitchen flooring, and wood laminate floors throughout the living room, dining area, and hallway. Interior utility area includes washer and dryer for extra convenience. The primary bedroom opens to a screened-in balcony. This amenity-rich community offers a large heated pool, pickleball and shuffleboard courts, a grilling area, and a clubhouse with a fitness center, perfect for staying active or socializing with neighbors. Additional conveniences include a common laundry room, a secure storage area, reserved covered parking, and elevator access. Ideally located in central Winter Haven, this condo is just minutes from downtown, shopping, dining, hospitals, and medical facilities, with easy access to I-4, placing you perfectly between Orlando and Tampa. Enjoy a vibrant lifestyle in a prime location.

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

Listing Agent: Rosa Suarez (954-682-2633)

Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom manufactured home with an office in the desirable 55+ community of Brookhaven Village, where you OWN your land! Situated on a large lot with no rear neighbors, this property offers an incredible sense of privacy and tranquility. From the moment you enter, you’ll notice the care and updates that have gone into this home over the years. Features include updated windows, fresh interior paint, and modern flooring throughout. Both the roof and AC were replaced within the last 5 years, ensuring peace of mind for years to come. The water heater was just replaced (02/2026). At the front of the home, the Florida room is fully enclosed and equipped with central air and heat, making it a comfortable year-round living space. The open floorplan flows seamlessly into a spacious living room, dining room with built-ins, and a bright kitchen offering ample cabinet and countertop space. The refrigerator was replaced 2 years ago, and the kitchen and bathroom cabinets have been repainted with updated hardware and modern light fixtures added for a fresh look. Down the hallway, you’ll find a dedicated office, ideal for working from home or enjoying a favorite hobby. The guest bedroom includes a walk-in closet, and the guest bath has been tastefully updated. The oversized primary suite is located at the back of the home and features a large walk-in closet and an ensuite bathroom with dual sinks and a walk-in shower. Step outside to your screened-in lanai, perfect for morning coffee or afternoon relaxation. Beyond that, the backyard oasis features a paved patio and serene views; your own private retreat. Hurricane shutters were just installed, adding extra protection and value. The low $34/month HOA fee includes access to the clubhouse, heated pool, shuffleboard courts, and storage area (upon availability). Brookhaven Village offers a prime Central Florida location close to HWY-27, providing easy access to I-4, Tampa, Orlando, and both Gulf and Atlantic beaches. Be sure to explore the 3-D virtual tour, then come see this wonderful home in person. Whether you’re escaping cold winters or seeking an affordable year-round lifestyle, this home is ready for you to enjoy the Florida sunshine. Schedule your private showing today!

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Enjoy effortless living in this beautifully updated condo perched on the 8th floor, offering breathtaking views of Spring Lake. This spacious residence features 2 bedrooms and 2 bathrooms, including a master suite with a walk-in closet and private bath. The custom kitchen is a standout with granite countertops, wainscoting ceiling, and a convenient bar, complemented by updated appliances and a new LG washer/dryer tower. Flooring includes ceramic tile, laminate, and cozy carpet in the bedrooms, while new windows with motion solar shades bring in natural light and comfort. Located in a desirable 55+ gated community, residents enjoy resort-style amenities including a heated pool, tennis courts, shuffleboard, and a welcoming social room with kitchen. Additional conveniences include 2 elevators, a covered parking space, and monthly fees that cover water, cable, internet, and community amenities.

Listing is courtesy of: NEXTHOME NORRIS & COMPANY REAL (863-875-5583)

Listing Agent: Michael Norris (863-287-3105)

Remarks: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout(optional first floor layout with den)and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.

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

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

Remarks: Under Construction. Introducing the Cali floorplan at Harmony at Lake Eloise, in Winter Haven, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,828 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and luxury vinyl plank floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The kitchen is a true highlight, including quartz countertops, sleek stainless-steel appliances, a walk-in pantry and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms have flexibility for various lifestyles. The primary suite located in the rear of the home is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Laundry won't be a chore with its dedicated space convenient to all bedrooms. Like all homes in Harmony at Lake Eloise, the Cali includes smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under contract-accepting backup offers. Accepting Backup Offers. Cash-flowing block duplex in Winter Haven, FL offering immediate income and upside, with (2) 2 bed / 1 bath units currently leased at $1,150/month & $1,200/Mo ($2,350/month total) to long-term tenants, providing stable day-one cash flow. Recent improvements include a brand-new roof (2023), privacy fence, and on-site storage shed with potential for additional income, while rents remain below market, presenting a straightforward opportunity to increase NOI through rent growth. Conveniently located near The Home Depot and major retail corridors, the property benefits from strong tenant demand, making it an attractive low-risk, value-add workforce housing investment in a growing Polk County submarket.

Listing is courtesy of: HANCO & ASSOCIATES (813-833-2185)

Listing Agent: Matthew Greezicki (813-833-2185)

Remarks: Under contract-accepting backup offers. Accepting Backup Offers** Cash-flowing block duplex in Winter Haven, FL offering immediate income and upside, with (2) 2 bed / 1 bath units currently leased at $1,050/month each ($2,100/month total) to long-term tenants, providing stable day-one cash flow. Recent improvements include a brand-new roof (2023), white vinyl privacy fence, and on-site storage shed with potential for additional income. Rents remain below market, presenting a straightforward opportunity to increase net income through rent growth. Conveniently located near The Home Depot and major retail corridors, the property benefits from strong tenant demand, making it an attractive low-risk, value-add workforce housing investment in a growing Polk County submarket.

Listing is courtesy of: HANCO & ASSOCIATES (813-833-2185)

Listing Agent: Matthew Greezicki (813-833-2185)

Remarks: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features an extended lot, a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.

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

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.

Listing is courtesy of: WF REALTY CORP. (407-994-2900)

Listing Agent: Adriana Sanchez (321-947-4014)

Remarks: MOVE-IN READY! Step inside this stunning one-story Castaway home feel right at home. As you enter through the front door, a welcoming foyer sets the tone for the open and inviting layout. Two spacious bedrooms are tucked at the front of the home and share a beautifully designed full bathroom, perfect for family or guests. A third bedroom with its own private bath offers comfort and privacy, ideal for visitors or a home office setup. Continue down the hallway and the home opens up into a wide, light-filled living area where the kitchen, dining, and family room seamlessly connect. The kitchen features sleek gray cabinets, quartz countertops, and a large island that overlooks the gathering spaces, making it the heart of the home—perfect for cooking, dining, and entertaining all at once. At the back of the home, the private primary suite provides a peaceful retreat with a spacious bathroom featuring double vanities, a walk-in shower, and a generous walk-in closet. Step outside through the sliding doors to a covered lanai, where you can relax and enjoy Florida’s sunshine year-round. Situated on a desirable corner homesite in Willowbrook North, this beautifully designed home offers modern finishes, an open concept layout, and a lifestyle made for comfort and connection.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: MOVE-IN READY! Beautiful 2 Level, Coastal elevation, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! The inviting front porch opens to a gracious foyer that leads you to the open main living space. The family room is open to the dining area and adjacent kitchen. The primary suite boasts an ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The second level offers a spacious loft and 2 secondary bedrooms each with walk-in closets and a full bathroom.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: LOCATION, LOCATION! 17 minutes from Cypress Gardens! 8.2 miles away from LEGOLAND! 6 mins from Winter Haven Airport! 11 miles from I-4 east Ramp! 5 mins from Publix and many local restaurants, parks, lakeside views and much more. Located on a quiet road, the newly built 1550 sq ft modern home includes continuous luxury vinyl flooring on both floors, luxury quartz countertops with matching backsplash, two tone kitchen cabinets, neutral paint throughout , high ceilings. Ceiling fans throughout, with glass front door accent. Two tone exterior with ambient lighting and black and gold accents throughout the home. Kitchen includes Calacatta quartz countertop on 6 ft island and backsplash with off white uppers and oak lowers, half bathroom downstairs includes a black and gold designer vanity, upstairs guest bathroom has a pop of black and white arched mosaic detail in the shower included in the vanity mirror as well as the vanity. Master bathroom includes a double fluted wood vanity with drawers and shelves, LED light up mirror and large format black and white Calacatta porcelain tile in entire shower. Chic exterior with a pop of sage green on the front door. Chrome and brush nickel finishings, matching interior lower cabinets and all bathroom vanities are with a pop of color modern finishing included throughout such as LED lights, curved mirrors and matching bathroom tiles.

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Lajuan Chambers (321-477-8805)