Homes For Sale in Winter Haven 33880 - 244 homes

Remarks: Discover the perfect blend of character, comfort, and convenience at this charming mid-century modern home near beautiful Lake Lulu! Featuring 3 bedrooms and 3 bathrooms, this unique property offers flexible living space with a private mother-in-law suite complete with its own entrance through the carport — ideal for multi-generational living, a young adult retreat, guest quarters, or even a spacious primary suite. Inside, you’ll find timeless mid-century charm paired with thoughtful updates, including newer double-pane windows and sliding glass doors that bring in natural light while improving energy efficiency. The AC and roof are both only 8 years old, and the home also features a newer water heater for added peace of mind. Located just moments from shopping, dining, and the renowned Chain of Lakes, this home puts you close to everything Winter Haven has to offer — all with NO HOA and NO CDD fees! Whether you’re looking for a primary residence, an investment opportunity, or a home with room to grow, this one is full of possibilities and ready for you to make it your own.

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

Listing Agent: Daniel Cook (863-430-8338)

Remarks: 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: Welcome to your own private backyard retreat in the heart of Winter Haven! This beautifully maintained 3-bedroom, 2-bath pool home sits on a spacious .31-acre lot with NO HOA and offers the perfect blend of comfort, convenience, and Florida living. The true showstopper is the incredible approximately *983-square-foot covered lanai*, creating an expansive outdoor living space rarely found in homes of this size. Perfect for entertaining, relaxing, outdoor dining, or even a home gym, this massive covered retreat overlooks the sports-style pool, oversized fenced backyard, custom playground, firepit, raised irrigated garden beds, and turf-and-tile entertaining area. Best of all, enjoy spectacular *LEGOLAND fireworks* views right from your own backyard. Inside, you'll find a bright and inviting floor plan with generous living spaces, comfortable bedrooms, and a well-appointed kitchen that flows seamlessly into the living and dining areas. Recent updates provide peace of mind, including a New Roof (2023), New Covered Lanai (2023), whole-home re-plumbing (2024), reverse osmosis system in the kitchen (2024), stainless steel dishwasher (2021), gas water heater (2021), irrigation system for yard (2023), updated light fixtures throughout, Ring security system with automatic flood lights, and added recessed lighting in the living room and kitchen. The outdoor space was thoughtfully enhanced in 2024 with stained fencing, rocked and irrigated landscape borders, a fully sealed playground, and beautifully designed gathering spaces that make this property ideal for everyday living and entertaining alike. Conveniently located just minutes from Downtown Winter Haven, LEGOLAND Florida Resort, major hospitals, shopping, dining, and everyday conveniences, this move-in-ready home offers the perfect combination of location, lifestyle, and value. Don't miss this rare opportunity to own a beautifully updated pool home with an extraordinary outdoor living experience. Schedule your private showing today!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: Location! Location! Location! This beautiful fully furnished home in Oakwood Estates is located next to the pool, tennis courts, and smaller clubhouse. Walk into the lanai as you enter the home. Once inside the home you will find a cozy family room and an open and and appealing kitchen just perfect for entertaining. The living room beyond the kitchen is open and spacious. The refrigerator was new in 2025. The guest bedroom opens onto the guest bath giving your overnight guest their own bathroom. The primary bedroom is large enough for a king sized bed, plus lots of closet storage space. The laundry with new washer and dryer is located inside the home. The roof was done in 2019 and the air conditioner in 2024. And if that isn't enough, there is new carpet throughout the home. Oakwood Estates is a 55+ community offering many activities and amenities. You can stay as busy as you would like, or just sit back and watch the world go by.

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

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

Remarks: Under contract-accepting backup offers. Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!

Listing is courtesy of: LPT REALTY LLC (386-388-7877)

Listing Agent: Trent Shackelford (941-518-7875)

Remarks: Welcome to 814 Sunset Cove Drive in Winter Haven! This move-in ready 4-bedroom, 2-bathroom home offers the perfect combination of comfort, style, and convenience. Nestled in a wonderful neighborhood, this well-maintained property features a spacious and functional floor plan designed for both everyday living and entertaining. Step outside to your own private retreat and enjoy the beautiful pool area, perfect for relaxing on sunny Florida days, hosting family gatherings, or creating lasting memories with friends. The backyard provides an inviting outdoor space to enjoy year-round. Inside, you’ll find generously sized bedrooms, comfortable living spaces, and a layout that makes you feel at home the moment you walk through the door. Whether you’re looking for your first home, a place to grow, or simply a move-in ready property with an exceptional outdoor living area, this home checks all the boxes. Don’t miss the opportunity to make this beautiful Winter Haven home your own!

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

Listing Agent: Ricky Catanzano, Jr (352-359-8991)

Remarks: Under contract-accepting backup offers. 3 bedroom, 2 bathroom concrete block home with a 1-car garage situated on a corner lot in the Jan Phyl Village area of Winter Haven with NO HOA. Several major updates were completed in 2021 including the roof, kitchen, flooring, guest bathroom flooring, and hot water heater. The home also features a newer dishwasher and new garage door. The backyard provides a great space for relaxing or entertaining. Conveniently located near Polk Parkway access, shopping, dining, schools, and surrounding Central Florida areas for an easier commute. Located in an established neighborhood with friendly neighbors and just a short distance from Winter Haven’s Chain of Lakes area. A solid option for a primary residence or investment property at an affordable price point.

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

Listing Agent: Aubrie Flint (863-618-6347)

Remarks: Under contract-accepting backup offers. 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: Charming 3-Bedroom, 2-Bathroom Home – Move-In Ready! Welcome to this well- maintained, single-family home, located in the desirable Squires Grove subdivision in Eagle Lake. Step inside to find brand new commercial-grade, waterproof, laminate flooring throughout. The spacious living room is perfect for relaxing and entertaining, while the kitchen includes a cozy dinette area. Enjoy Florida living at its best with a screened-in back patio, complete with lighting and tile flooring. The patio opens up to your large back yard. This home also includes a two-car garage. BRAND NEW A/C system installed in March 2025, ensuring comfort year-round and a NEW roof coming soon!

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Tony Fridovich (863-698-4267)

Remarks: Welcome to this spacious home Located in the gated community of The Gardens, this spacious 4-bedroom, 2-bath home offers an open layout designed for comfortable living and entertaining. The large primary suite features a tray ceiling, two walk-in closets, dual sinks, a tile shower, and a garden tub. Step outside to enjoy a generous backyard with an outdoor kitchen/BBQ area, above-ground pool, storage shed, and plenty of room to relax or entertain.

Listing is courtesy of: ORCHARD BROKERAGE, LLC (844-515-9880)

Listing Agent: Ray Garza (407-607-9382)

Remarks: Condo located in Winter Haven FL, the Water Ski Capital of the World and only 6 minutes from Legoland! Ground-floor, furnished condo in Sandy Cove, a lakefront community on the beautiful Winter Haven Chain of Lakes. This furnished 2-bedroom, 1-bath unit offers low-maintenance living that’s ideal for full-time residents, seasonal owners, retirees, or anyone seeking a convenient Florida lifestyle. The layout offers comfortable living with a spacious great room featuring laminate flooring, a ceiling fan, and sliding doors leading to the enclosed Florida room. The adjacent dining space is cozy and ideal for entertaining or quiet nights in. The kitchen is complete with quartz countertops, included appliances, and a stackable washer and dryer. The unit also features double-pane windows for improved energy efficiency, comfort, and noise reduction. The primary bedroom is generously sized and features a ceiling fan, walk-in closet, and direct access to the bathroom. The guest bedroom is also comfortably sized with a built-in closet, ceiling fan, and en-suite-style bathroom access. The bathroom has been updated with an upgraded vanity, solid-surface countertop, and walk-in shower. Enjoy outdoor living from the enclosed Florida room with screens and vinyl windows, perfect for relaxing or entertaining year-round. This ground-floor unit is ideally positioned just steps from the community clubhouse, grill area, and heated pool maintained at approximately 85 degrees for year-round enjoyment. Sandy Cove also offers a community dock on Lake Lulu, one of twenty+ lakes on the Winter Haven Chain, providing a peaceful setting to unwind, enjoy waterfront views, and take in beautiful Florida sunsets. Residents enjoy the relaxed lifestyle that makes Winter Haven so desirable, including boating, fishing, lakeside dining, golf courses, walking paths, and year-round community events. Conveniently located near everyday essentials and recreation, the condo is just minutes from Publix Super Markets, CVS Pharmacy, restaurants, banks, medical offices, and Walmart shopping. Nearby public boat access on Lake Summit makes it easy to enjoy the Chain of Lakes lifestyle, while several local golf courses are only a short drive away. The location also provides convenient access to both Orlando and ,making this an excellent choice for easy, low-maintenance Central Florida living.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

Remarks: EXECUTIVE POOL HOME SITUATED ON 2.39 ACRES HORSE FARM. 4 BEDROOMS, 3 BATHS, including 2 barns. Well built and maintained barn with 4 stalls, tack room and hay and feed room. Additional barn with two overhead doors for tractors and equipment as well as workshop. Both barns have metal roofs. Seller currently has a horse and donkey on the property. Property is beautifully landscaped with an abundance of tropical plants under large spreading oak trees. Plenty of parking spaces for your recreational vehicles and toys. This beautiful home has been meticulously maintained thru out the years with lots of upgrades. Wood look tile throughout, salt water inground pool overlooks the pasture. Stone fireplace welcomes you into the family room. Large gourmet kitchen with lots of room for the family cooks. Two master suites or use one for an in-law suite. House roof is shingle and was replaced in 2017 and AC is 3-4 years old. This property is one of a kind and hard to find so convenient to Winter Haven and Lakeland. These properties rarely come on the market so don’t wait to see this one.

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

Listing Agent: Sharon Watson (863-557-4800)

Remarks: Completely renovated and move in-ready Large 4 bedroom, 2 bathroom house awaits your family! On a desirable corner lot, in a quiet neighborhood. New Roof, New Paint, New Flooring all through the house, New Stainless Steel Appliances, New Kitchen Faucet, Like a New Home!! Master Bath has a walk in closet and Garden Tub and Seperate Shower with a Seat. This home offeres a Separate Dining area and a Office or Playroom. Close to the new Polk Parkway extension, so travel to schools, shopping, restaurants and entertainment is super convenient. Great school district and priced to sell quickly. Call today for a showing!

Listing is courtesy of: AVERY PROPERTIES INC. (863-682-1902)

Listing Agent: Anne Greenhow (863-698-4562)

Remarks: Welcome to this spacious 3-bedroom, 2-bath home with a dedicated office/flex room in the Oak Preserve neighborhood of Winter Haven. Offering a popular split-bedroom floor plan, generously sized rooms, an open-concept layout, and attached two-car garage, this home provides the space and flexibility today's buyers are looking for. The kitchen serves as the heart of the home, featuring abundant cabinet and counter space, two pantries, a breakfast bar, and a large dining nook with room for a full-sized table and chairs. The kitchen flows seamlessly into the living room and formal dining area, creating an ideal setup for entertaining guests, hosting holidays, or simply enjoying everyday life. The private primary suite offers a spacious retreat with a large walk-in closet and an ensuite bath featuring dual sinks, a soaking tub, and a separate shower. Two additional bedrooms and a generously sized office/den provide plenty of room for family, guests, remote work, hobbies, or a playroom. Outside, the fenced backyard offers privacy and space to enjoy the Florida lifestyle. A standout feature of the property is the detached 10' x 20' workshop complete with electricity and its own mini-split air conditioning system. Whether you need a workshop, home gym, studio, storage space, or a place to pursue your hobbies, this versatile building provides endless functionality. The home has been well maintained, and the sellers plan to install a new roof prior to closing, providing added value and peace of mind for the future owner. The yard is ready for a fresh landscaping vision, creating an opportunity to personalize the outdoor space and enhance the home's curb appeal. Conveniently located near shopping, dining, medical facilities, schools, and major roadways, this Winter Haven home combines a functional floor plan, flexible living spaces, a fenced yard, detached workshop, and an excellent location. If you've been searching for a move-in ready home with space to spread out and room to make it your own, this property deserves a closer look.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Lindsey Haubner (863-640-1181)

Remarks: Welcome to this stylish and energy-conscious 4-bedroom, 2-bath home located in the highly desirable Eagles Landing Community, located in beautiful Winterhaven Florida. Built just three years ago, this home offers a spacious open-concept floor plan that’s perfect for both everyday living and entertaining. The large windows throughout the home allow for an abundance of natural light, creating a warm and inviting atmosphere. The heart of the home features a modern kitchen that flows seamlessly into the dining and living areas, creating a bright and welcoming space. The primary suite includes a generous en-suite bathroom, while three additional bedrooms that offer plenty of room for family, guests, or a home office. One of the standout features of this home is the solar panels. These solar panels not only reduce energy costs but also contribute to a more sustainable lifestyle. You'll have the opportunity to benefit from lower energy bills and a reduced carbon footprint while enjoying the modern amenities of this home. Another feature of this beautiful home is the water filtration system, which provides clean and healthy water for you and your family. This added convenience ensures that you can enjoy fresh purified water right from your tap Outside, you'll find a well-maintained yard, perfect for enjoying the Florida weather. While the home does offer a comfortable and inviting space to call home. Additionally, there’s ample room for installing a luxurious underground pool to enjoy the delightful Florida Climate. Plus, the backyard is partially fenced for added privacy and security. Great for First Time Homebuyers, Vacation Home or Investment Property Don't miss the chance to make this wonderful property in Winterhaven, Florida your new home. Also with easy access to shopping, dining, and local attractions.

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

Listing Agent: Deana Lainhart (239-289-1195)

Remarks: Stunning 3-Bedroom, 2-Bath Home – Move-In Ready! Welcome to this move-in ready home in a prime location! Boasting a spacious and open floor plan, this 3-bedroom, 2-bathroom gem offers the perfect blend of comfort and style. Enjoy An extra-large back patio for these summer evening BBQ's! The well-appointed kitchen features stainless steel appliances, a convenient breakfast bar, a closet pantry, and ceramic tile flooring, all complemented by a cozy breakfast nook. With both a large living room and a separate family room, there’s ample space for relaxing and entertaining. The versatile living/dining room combo offers a seamless flow for hosting guests. Enjoy the privacy and tranquility of the split-bedroom design, with the expansive master suite serving as your personal retreat. The primary bath is a true highlight, featuring a dual vanity, walk-in closet, and a relaxing garden tub—perfect for unwinding after a long day. Key Features: Bright and open floor plan with plenty of natural light Large primary suite with luxurious en-suite bath Spacious living and family rooms for flexible living Well-equipped kitchen with modern stainless steel appliances Great location with easy access to both Tampa and Lakeland All of this at an incredible price! Don’t miss your chance to call this home yours. Call today to schedule your private showing!

Listing is courtesy of: CITRAVEST MANAGEMENT LLC (407-495-4744)

Listing Agent: Lesley Guarino (315-783-4744)

Remarks: Under contract-accepting backup offers. MAJOR PRICE ADJUSTMENT!!! VERY MOTIVATED SELLER!! Walk right into this well maintained home. The furnishings you see will remain with the home. The kitchen is large and very functional with lots of cabinets and counter space. Enjoy the open and inviting living area, perfect for entertaining. Sit on the screened front porch enjoying your morning coffee with a nice view of the lake. There is no carpet in this home with laminate flooring in all the living areas. Oakwood Estates, a 55+ community offers many amenities and activities. Get your coffee and donuts every Wednesday morning at Koffee Klatch, enjoy an ice cream sundae twice a month or dance to the music at any of the dances held during the winter months. In addition to the many activities, there are two pools and two clubhouses, shuffleboard, miniature golf, bocci ball, tennis courts, and much more. You can be as busy as you would like or just sit back and enjoy the peaceful community.

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

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

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: Come and see this move-in ready four-bedroom, two-bathroom home in the lovely Coventry Cove neighborhood. This home features a spacious open floor plan that seamlessly connects the living spaces for a highly functional and airy feel. The updated kitchen boasts beautiful granite countertops and stainless steel appliances, keeping the chef of the family engaged with the rest of the home. A well-appointed bathroom includes the convenience of a double vanity. Step outside to enjoy a private, fully fenced-in backyard that serves as a perfect space for outdoor entertaining or relaxing. Ideally located in Winter Haven, this home offers easy access to excellent shopping, dining, and vibrant local attractions. Schedule your private showing today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Check this out!! The home has new vinyl plank and new carpet in the bedrooms and a new roof in 2025. Enjoy the nice sized living room with relaxing cool blue paint and chair rail. Additionally there is a built in for additional storage and display area for your trinkets. The kitchen offers a nice flooring, with upgraded countertops and lots of cabinets and storage. The hall bathroom has been upgraded with vinyl plank and a custom shower. The primary bathroom offers nice space and a walk in closet. All the floors have plywood subfloors with vinyl plank or carpet. The back porch on the home has been framed in and divided into two office spaces. The walls at the back of the house are freestanding and can be easily removed revealing the glass behind them. Step out the back door onto a covered porch area allowing access to the shed that houses the washer and dryer. Oakwood Estates, a 55+ community, offers many activities and amenities. You can be as active as you would like or just sit back and watch the world go by. The Seller is a smoker inside the home. Please beware if you have smoke allergies.

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

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