Homes For Sale in Winter Haven 33880 - 249 homes

Remarks: Experience lakeside living in this custom-built home, perfectly situated on the shores of Lake Grassy. As you approach the property, you are greeted by a sprawling 13’x60’ front porch complete with a charming swing and ample space for entertaining. Imagine hosting gatherings here, with tables lined up as you enjoy views of the beautifully landscaped front yard. Step inside through a wide foyer that seamlessly flows into a spacious family room, where soaring ceilings amplify the sense of openness and elegance. The heart of the home is the newly renovated kitchen, featuring hickory wood cabinets with convenient roll-out drawers, modern appliances, and an eat-in area framed by a picture window offering breathtaking lake views. Adjacent to the kitchen, the formal dining room features sliding glass doors that open to a cozy back porch, creating the perfect indoor-outdoor flow for dining and relaxation. The home boasts 180 feet of lake frontage, complete with a private boat dock and concrete retaining wall, inviting endless water activities and lakeside enjoyment. Eco-friendly and cost-efficient, this home is equipped with fully paid solar panels and a private well, ensuring significant savings no utility bills. The expansive laundry room provides additional storage space, enhancing functionality. The main bedroom is a serene sanctuary with its own private lake view and sliding glass door that opens to a private lanai, offering a tranquil space to unwind. The main bedroom has on-suite bathroom, separate water closet, double sinks, jacuzzi tub, separate shower and double sinks. The second bedroom is thoughtfully designed with a dog door leading to secure dog fencing, making pet care effortless. The second and third bedrooms have walk in closets and share a convenient 2nd bathroom. Car enthusiasts or hobbyists will appreciate the oversized 35’x38’ garage, perfect for a workshop or extra storage, and includes a full bathroom. Additionally, a detached building is primed to become an in-law suite or a private home office, adapting to your changing needs. Don’t miss the opportunity to own this lakefront gem. Call for your private viewing today and start living your dream on Lake Grassy!

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Kelley Blackburn (813-478-0023)

Remarks: ***Investor Special*** Welcome to this 2 bedroom 1 bath home. It is in need of some work but not out of range for the right do it your self investor. It is situated on .6 acres of land with room on the back of the lot for a garden, chickens or storage building. This property is located in Winter Haven and is close to everything you need.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Craig Burke (863-899-5010)

Remarks: Pack your bags and move right into this very well maintained home located in Oakwood Estates, a 55+ community. The floorplan offers two living areas with nice sized bedroom. The cathedral ceilings make the living area feel spacious. The functional kitchen provides lots of storage with the built-in in the dining area offering more storage. The home features all new windows, with acrylic windows in the front porch area. The HVAC is one year old. The roof-over was installed approximately 2017. This home comes furnished right down to the dishes, silverware, pots and pans. Oakwood Estates offers many amenities and activities to keep you as busy as you would like, or just sit on the front porch and enjoy the view of the lake.

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

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

Remarks: Welcome to maintenance-free living in the heart of Winter Haven! This darling 2-bedroom, 2-bath villa is perfectly located in the desirable Imperial Villas a 55+ residential community, sitting within a short walking distance to beautiful Lake Howard. Inside, you’ll find updated flooring throughout and both bathrooms tastefully renovated, giving the home a fresh, move-in-ready feel. The open layout flows seamlessly to a peaceful sitting lanai overlooking the heated community pool—the perfect spot to enjoy your morning coffee or unwind in the evenings. Major updates add peace of mind, including a resurfaced roof with a 15-year warranty, a tankless hot water heater, and an updated electrical system. The low HOA fee of just $270/month covers water, high-speed internet, cable, gas, and all grounds maintenance—you only pay for electric! The property includes 2 assigned parking spaces, with one under a carport, and the community has ample visitor parking. Enjoy easy access to shopping, dining, and downtown Winter Haven events, all while embracing a relaxed, low-maintenance lifestyle close to the lake. Whether you’re downsizing, snowbirding, or looking for carefree Florida living, this villa checks all the boxes. Property is eligible for FHA Financing! Move in, relax, and enjoy the best of Winter Haven living!

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

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

Remarks: Under contract-accepting backup offers. Enjoy this clean 2 bedroom, 2 bath villa in the community of Mayfair Place. Step into a spacious great room with soaring ceilings and all ceramic tile floors throughout, offering both style and ease of maintenance. The open kitchen includes plenty of counterspace, gas range/stove, and breakfast bar. The primary suite features sliding glass doors leading to a peaceful back patio, the perfect spot for morning coffee or winding down in the evening. Inside utility room with extra cabinet and counter space, plus an additional storage closet for even more convenience. Just minutes from downtown, this villa provides easy access to local dining, shopping, and medical facilities.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Check out this wonderfully maintained home located in Oakwood Estates, a 55+ community. The HVAC has just been replaced and the roof is 3 years old. The living room is spacious and comfortable. Both bedrooms have walk in closets with lots of storage. The side and front porches provide additional living space. The home will be sold furnished less personal items with everything you will need to move right in. The amenities at Oakwood Estates include two clubhouses, two pools, a fishing pier, shuffleboard, tennis courts, miniature golf, and much more. You can join in of the many activities offered or just sit back and enjoy the peaceful community. Call today for your appointment to see this amazing home.

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

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

Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 3-bath home located in one of Winter Haven’s most established and sought-after neighborhoods. Situated on a spacious 0.26-acre lot, this property offers timeless character, mature surroundings, and a location rich in local history. A standout feature of the home is the private suite with its own entrance and full bathroom, ideal for guests, extended family, or a flexible work-from-home space. The layout provides both privacy and functionality, making it a rare find in this area. Recent updates include a newer roof (approx. 1 year old), updated electrical, a new water heater, and a newer A/C unit (2018), offering peace of mind on major systems. Enjoy the unique setting with nearby views of Lake Elbert to the north and Lake Otis to the south, surrounded by well-established homes and nearby lakefront properties. The home offers great bones and classic charm, presenting an excellent opportunity for buyers to update and personalize while investing in a premier location. Conveniently located near downtown Winter Haven, shopping, dining, and more.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Dave Westphal (863-287-3302)

Remarks: Location, Location! This charming 3-bedroom, 2-bath home, large living room and a huge family room ( could be a 4th bedroom) is situated in the vibrant and growing Winter Haven area. Conveniently close to LEGOLAND, shopping centers, hospitals, and medical offices, it offers both comfort and accessibility. Solar Panels( worth $44K) will be paid by seller at closing ! This home has a nice back yard and side porch. The spacious living and dining areas are perfect for family gatherings and entertaining friends. With generously sized bedrooms, tiled floors, and a custom-built kitchen, this home is ready for you to add your personal touch. With a bit of creativity and effort, this house has the potential to become your dream home. Motivated sellers.

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Lucy Martinez (863-521-4156)

Remarks: Charm and curb appeal abound for this Winter Haven home! Step inside into the inviting foyer and into the well-appointed living room, positioned at the center of the home. The kitchen boasts a 4-piece appliance package, ample storage, hard surface countertops, and an eat-in dining room. This split floorplan offers the primary bedroom on one side of the home and two secondary on the other. Come and see for yourself the possibilities that this home has to offer!

Listing is courtesy of: EVERYSTATE INC. (501-725-1234)

Listing Agent: Blake Keathley (661-900-9145)

Remarks: Welcome home to this beautiful 2-story BLOCK HOME built in 2022 - still feels LIKE NEW and full of warmth and charm! This home offers INCREDIBLE SPACE, BRIGHT ROOMS, and a PEACEFUL WATER VIEW - perfect for family living and entertaining. Step inside to a welcoming foyer that opens to a FLEX ROOM - perfect for a formal dining room, formal living room or office. The kitchen is truly the HEART OF THE HOME, featuring a WALK-IN PANTRY, PLENTY OF CABINETS, LOTS OF COUNTER SPACE, a BREAKFAST BAR for quick meals, and an EAT-IN DINING AREA that opens to the FAMILY ROOM and SLIDING GLASS DOORS that lead to a FULLY FENCED BACKYARD with LAKE VIEWS. Downstairs also includes a FULL BEDROOM and FULL BATHROOM, great for GUESTS or IN-LAWS. Upstairs, you’ll find a LARGE MASTER SUITE with TWO WALK-IN CLOSETS and DOUBLE SINKS. There’s also an additional BONUS/FLEX ROOM that can be used as a game room, family room and/or den/office. Four additional SPACIOUS BEDROOMS, a FULL HALL BATHROOM, and a CONVENIENT UPSTAIRS LAUNDRY ROOM make this home as functional as it is beautiful. MODERN UPGRADES include UPDATED LIGHT FIXTURES, LUXURY VINYL FLOORING, FRESH DESIGNER TOUCHES, and PLENTY OF NATURAL LIGHT throughout. With a 2-CAR GARAGE, FRONT PORCH, and HUGE BACKYARD overlooking the WATER, this home has everything your family needs! DON’T MISS OUT - homes with THIS MUCH SPACE, in LIKE-NEW CONDITION, and on THE WATER, don’t last long! Schedule your showing TODAY before it’s gone!

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: Yanery Perez (863-838-9091)

Remarks: Welcome to this beautifully renovated home located in a secure gated community, offering not only privacy and peace of mind but also a low annual HOA fee. This spacious property features 4 bedrooms plus a versatile bonus room and 3 fully remodeled bathrooms, thoughtfully designed to provide comfort for everyday living and privacy for guests. As you enter, you are welcomed by high ceilings and an open-concept layout filled with natural light, creating a bright and inviting atmosphere throughout the home. The interior showcases new flooring, fresh paint, and modern finishes that elevate every space. The kitchen has been fully updated with elegant cabinetry, gold hardware, spacious countertops, stainless steel appliances, and stylish lighting, all seamlessly connected to the main living areas, making it ideal for both daily use and entertaining. Both the kitchen and bathroom countertops feature high-quality quartz, offering durability, low maintenance, and a clean, modern look that enhances the overall design of the home. The primary bathroom offers a true luxury experience with floor-to-ceiling tile, a freestanding soaking tub positioned under a large window, a frameless glass shower with modern gold finishes, and a double vanity with contemporary mirrors and lighting. The additional bathrooms have also been completely renovated with clean, modern designs and high-quality materials. The home also includes a three-car garage and a large driveway, providing ample parking and storage space. The backyard offers a private outdoor area with plenty of potential for relaxation or future enhancements. Located in a quiet and well-maintained community, this property combines modern upgrades, functional layout, and an excellent location, making it a perfect option for both homeowners and investors seeking a move-in ready home.

Listing is courtesy of: AVENUE HOMES LLC (833-499-2980)

Listing Agent: Jorge Orama (813-753-4656)

Remarks: Price to sell. Manufactured home located in Winter Haven on approximately 0.23 acres of owned land, offering privacy and spacious outdoor area. The property has been well maintained and features recent updates including a new roof (2025), new water heater, and updated bathroom. Front concrete slab provides functional outdoor space and convenient parking. Conveniently located near major roads, shopping, schools, and everyday amenities. Excellent opportunity to own land with no lot rent.

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

Listing Agent: Idalgisa De Jesus (347-797-7849)

Remarks: Walk right into this open and spacious home. The kitchen is perfect for entertaining with newer cabinets and cooktop. The cathedral ceilings in the living room give the feel of lots of space. The floorplan offers 2 living areas. The guest bedroom has the main bathroom attached which is perfect for those overnight guests. The primary bedroom is spacious with two separate closets for him and her with a nice sized shower stall in the primary bathroom. The shingle roof was installed in 2021. The vapor barrier was replaced in 2023 and the home has new skirting. The side porch offers more living space and is backed with a great workshop area. The laundry is inside the home. If all that isn't enough there is an EV charging port installed. This home is located in Oakwood Estates, a 55+ community offering many activities or just sit back and enjoy the peaceful community. Make your appointment today!! This home will be sold unfurnished with appliances only.

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

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

Remarks: PRE-FORECLOSURE - 3 Bedroom/2 Bath Home in a gated community. This home is only 4 years old, but it needs a lot of cosmetic work. The Buyers may assume the current mortgage at 3% interest.

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

Listing Agent: Linda Andre (863-294-7541)

Remarks: Welcome to paradise, in this 2/2 with a enclosed front porch, to watch the beautiful Florida sunsets. The gated 55 plus community offers many amenities such as tennis, fishing pier, two heated pools, shuffle board, miniature golf, bocce ball, two club houses, fishing pier, plus many planned activities.

Listing is courtesy of: SOUTHERN BELLE REALTY (863-299-7800)

Listing Agent: Reta Stead (863-299-7800)

Remarks: This home is a MUST SEE? You will find many updates in this home from the beautiful granite counters in the kitchen and new kitchen cabinets to the remodeled bathrooms. All flooring is either ceramic or vinyl flooring. The Singled roof is approximately 11 years old and the ac was installed in 2025. The water heater was installed in 2024. This home will be sold mostly furnished. If that isn't enough, from the carport area there is a beautiful view of the lake and lakeside amenities. Oakwood Estates is a very active 55+ community offering many amenities including two pools, two clubhouses, miniature golf, tennis courts, shuffleboard and more. You can be as busy as you want, or just sit back and enjoy peaceful Florida living. Visit the Oakwood website for more info on the community and to see the governing docs.

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

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

Remarks: Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend of comfort and convenience in this beautiful Winter Haven property. Nestled in a peaceful neighborhood, this property offers spacious living areas and a welcoming atmosphere. Enjoy bright living, a well-appointed kitchen, and generously sized bedrooms. Don't miss out- schedule a showing today!

Listing is courtesy of: RIVERA & ASSOCIATES REALTY (813-443-5031)

Listing Agent: Maria Rivera (813-842-7399)

Remarks: Move right into this fully furnished home. This home offers lots of space with walk in closets in both bedrooms and a new vanity in the primary bathroom. Plus the lanai offers extra living space as well as the bonus room on the front of the home. The refrigerator and washer and dryer are newer. The metal roof was installed in 2024. Oakwood Estates, a 55+ community, offers many activities and amenities, so you can be as busy as you would like, or just sit back and enjoy the peaceful community. The rocker recliner in the living room and TVs do not convey.

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

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

Remarks: PRICE REDUCTION!!! Bring your buyers. Great opportunity at new price.... Welcome to 740 Squires Grove Dr. This beautiful 5 bedroom, 3 bath residence offers the space you've looking for, filled with natural light and and large fenced backyard ideal for gatherings, pets or relaxing outdoors. Well located near shopping, dining, hospitals, major highways, and just minutes from LEGOLAND. Book your showing today!.

Listing is courtesy of: NORTHGROUP REAL ESTATE, INC (561-222-1850)

Listing Agent: Lulis Batista (407-969-2098)

Remarks: Short Sale. Requires a some TLC & Refresh. Pool Home.

Listing is courtesy of: WESTBAY REAL ESTATE (813-833-2045)

Listing Agent: Randy Patrick (813-833-2045)