Winter Haven Homes For Sale & Real Estate - 708 homes

Remarks: Under contract-accepting backup offers. Discover the perfect blend of modern living and convenience in this brand new 3-bedroom, 2-bathroom home located in the heart of Winter Haven, just minutes from the serene shores of Lake Hartridge. Best of all, there’s NO HOA to worry about! As you step inside, you’ll be greeted by a bright and airy open floor plan that flows seamlessly throughout the home. The luxury vinyl plank flooring adds both elegance and durability, making it a great choice for busy households. The heart of the home is undoubtedly the beautiful kitchen, which features stainless-steel appliances, quartz countertops, and plenty of cabinetry to store all your cooking essentials. The kitchen design allows for easy interaction with guests in the spacious living room, ensuring you never miss a moment while entertaining. Retreat to the primary bedroom, a sanctuary designed for relaxation. This inviting space comes complete with a generous walk-in closet and a luxurious ensuite bathroom, featuring dual sinks and a modern walk-in shower—providing a perfect spot to unwind after a long day. The two additional bedrooms are thoughtfully designed with equal sizing and each boasts a walk-in closet, ideal for family members or guests. The second bathroom, conveniently located near the entrance of the home, includes a shower and tub combination, offering both comfort and functionality. Situated in the heart of WinterHaven, this home places you in close proximity to a variety of retailers, restaurants, and shops, ensuring you have everything you need right at your fingertips. Plus, the adjacent home is also available for sale and currently under construction, offering a unique investment opportunity. Don’t miss your chance to own this exceptional new home in Winter Haven—schedule a tour today and envision the possibilities!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: John Hubbert, Jr (863-243-4024)

Remarks: Welcome to your own 3/4-acre mini farm oasis! This fully fenced and gated property is a secure haven offering space for a variety of living needs, farm animals and plenty of room for parking. Large carport with garage attached. Mature trees provide serene shade on this picturesque retreat. The property includes a shed with chicken coops and pig pens, perfect for your feathered and four-legged friends. Updated remodeled 3BR, 1.5BA mobile home with an open floor plan, new fixtures, and an inside laundry room for convenience. Plenty of room for dogs, goats, boats, and RVs with electric hookup. Grow your garden with crystal clear well water. Enjoy the front porch with rocking chairs in screened room. Experience farm living with modern comfort and affordability. Welcome to your peaceful country sanctuary! Cash Only Sale. The info provided herein is subject to errors, omissions or changes without notice, and Seller expressly disclaim any warranty or representation regarding the Property Information. You must independently verify the Property Information prior to purchasing the Property.

Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)

Listing Agent: Camilo Perez (833-700-2782)

Remarks: SOLID CONCRETE BLOCK 10-PLEX CONSISTING OF TWO TRIPLEXES CONNECTED ONLY BY A ROOF OVER A WALKWAY AND A TWO STORY QUADPLEX. ALL THE UNITS ARE FULLY OCCUPIED. ALL TEN UNITS ARE ONE BEDROOM WITH ONE BATH AVERAGING ABOUT $ 875/MONTH IN RENT. MOST OF THE UNITS HAVE CERAMIC TILE LOW MAINTENANCE FLOORS. ALL UNITS HAVE WINDOW A/Cs. THE QUADPLEX HAS A NEW (MARCH, 2025) TAMCO TITAN SHINGLE ROOF RATED AT 160 MPH. THE ROOF ALSO HAS PEEL AND STICK UNDERLAYMENT INSTEAD OF THE TYPICAL 15 OR 30 POUND CRAYPE PAPER. THIS BASICLY MEANS YOU HAVE A SECOND ROOF UNDER THE SHINGLES. PROPERTY IS PROFESSIONALLY MANAGED AND WELL MAINTAINED. THE RENTS CONTINUE TO INCREASE AS THE CONDITION AND LOCATION OF THE UNITS MAKE THEM VERY POPULAR. INSPECTIONS AFTER ACCEPTED OFFER. LISTING BROKER HAS A SIGNIFICANT FINANCIAL INTEREST IN THE OWNING ENTITY.

Listing is courtesy of: HOSANNA REAL ESTATE SERVICES (863-698-7858)

Listing Agent: Tom Novack (541-606-4316)

Remarks: 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: Welcome to a wonderful new chapter in Lake Ashton, Central Florida’s premier fifty-five plus active adult community, where this thoughtfully maintained two bedroom, two bath home offers comfort, style, and peace of mind. Recently refreshed with exterior and interior paint, enhanced energy-saving features include additional attic foil insulation, and surrounded by pristine landscaping, the home immediately makes a welcoming impression with its screened front entry, elegant stone veneer, and newly sealed veneer and pavers. Inside, the living room feels open and inviting beneath a cathedral ceiling and new vinyl plank flooring, while the spacious primary suite and separate guest bedroom and bath provide privacy and relaxation for both owners and visitors. The kitchen is both functional and attractive with solid wood cabinetry and granite countertops, and the generously sized screened veranda creates the perfect setting for quiet mornings, relaxed evenings, or easy entertaining. This home truly shines when experienced in person, and life at Lake Ashton extends far beyond the front door with two championship golf courses, an expansive clubhouse, fitness center, theater, pickleball courts, bowling alley, on-site restaurant, and an array of activities that make every day feel full and rewarding. Blending comfort, convenience, and an exceptional sense of community, this inviting property is ready to welcome you home and offer the very best of Florida living.

Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-455-2709)

Listing Agent: Brad Kirwan (863-280-0390)

Remarks: Experience timeless elegance in this executive Mediterranean-style home, where refined architecture meets luxurious living. Welcome to Heron Cay, an exclusive retreat comprised of just two dozen custom homes tucked away near Lake Eloise. Make your way through the gate and wind around to the cul-de-sac where this exceptional home stands ready to welcome and impress you. Upon entering through the double doors, prepare to be captivated by the grand scale of this home's living spaces and rich textures. Open-concept design flows seamlessly into expansive living and dining areas, highlighted by soaring ceilings, a travertine fireplace, and windows that bathe the home in natural light. The gourmet chef’s kitchen is a true showpiece, featuring premium stainless-steel appliances including a gas range, beautiful cabinetry, a wine refrigerator, an island, and elegant granite countertops—ideal for both everyday living and upscale entertaining. Be sure to take note of the ample storage and rolling ladder in the well appointed butler's pantry, and the custom coffee station. Retreat to the lavish primary suite, complete with a spa-inspired bathroom, walk-in shower, separate steam shower, dual vanities, and an expansive custom closet. The remaining bedrooms are generously sized and thoughtfully designed spaces to ensure comfort for family and visitors alike. Step outside to your own private oasis—lush landscaping, an enclosed pool and patio, and ample space for outdoor dining and relaxation create the ultimate setting for year-round enjoyment. On a practical note, the home is equipped with a 22KW Generac generator, which is sure to provide peace of mind during storm season. Combining Mediterranean charm with executive-level finishes, this extraordinary home offers privacy, prestige, and craftsmanship in one of the area’s most desirable gated communities. Request your private tour today, and ask about the seller's assumable incredible interest rate!

Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)

Listing Agent: Misty Mccracken (863-289-0735)

Remarks: ***BELOW MARKET VALUE*** New Construction 3 Bedrooms 2 Baths built by the best builder in the area WCM Construction! This home is built with high quality kitchen and bathroom cabinetry, Level 3 Granite counters throughout kitchen and baths, high end appliances, beautiful wood grain tile throughout the entire home - no carpet or wood. Built with perfection, yet affordably priced! Check out the complete walk-thru video or better yet, call for an appointment to see this beauty in person!

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

Listing Agent: Barry Macchione (863-604-7455)

Remarks: Impeccably maintained home in the sought-after Traditions 55+ community in Winter Haven! This spacious 2-bedroom, 2-bath home with a dedicated office/den offers over 1,500 square feet of open-concept living space, designed for both comfort and functionality. The home features new flooring throughout, upgraded countertops, 36-inch kitchen cabinets, and modern lighting fixtures, creating a bright and inviting kitchen and living area perfect for everyday living or entertaining. Both bathrooms have been tastefully upgraded, and additional improvements include a new water heater and recently replaced AC coil for added efficiency and peace of mind. The home was freshly painted inside and out in 2023, giving it a clean, modern feel throughout. Step outside to enjoy the new screened-in porch, ideal for relaxing mornings or evening gatherings while overlooking the newly installed sod that enhances the home’s curb appeal. The extended driveway provides additional parking and convenience, and the home is handicap accessible, offering added functionality and ease of living. Residents of Traditions enjoy resort-style amenities, including community boat ramp access, fishing, dock, and private water access, along with a community pool and recreational facilities. The HOA includes cable TV, internet, exterior, grounds maintenance, pool maintenance, recreational facilities, and security, making this a truly low-maintenance lifestyle. Located just minutes from shopping, dining, and major roadways, this move-in ready home combines modern updates, accessibility, and the vibrant lifestyle of one of Winter Haven’s most desirable active adult communities.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Nathan Mercado (407-353-8612)

Remarks: Under contract-accepting backup offers. Fully Renovated Golf Course Home – Perfect for Full or Part-Time Living Located directly on the golf course in Cypress Woods Golf & Country Club, this beautifully renovated home is a 2 bedroom, 2-bath home with an optional 3rd bedroom or sunroom. Home showcases quality craftsmanship and modern upgrades throughout — ideal for both full-time residents and seasonal owners. The open floor plan features updated flooring, designer lighting, and a completely remodeled kitchen with premium cabinetry, Corian countertops, stainless-steel appliances, new hot water heater and air conditioning system. Both bathrooms have been tastefully renovated with stylish, high-end finishes. The spacious primary suite offers a beautifully updated en-suite bath and its own private porch, creating a peaceful retreat. Positioned on the golf course, the home enjoys a prime setting within this desirable Central Florida community. Community amenities include championship golf, clubhouse dining, fitness center, and a resort-style pool. This move-in ready home offers comfort, quality, and convenience in a highly sought-after location.

Listing is courtesy of: FAITH AND FAMILY REALTY LLC (863-712-1991)

Listing Agent: Lynn Arthur (336-596-5547)

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: Discover the best of retirement living in Brookhaven, a welcoming 55+ community! This partially furnished and well-maintained home sits on a desirable lot with OWNED LAND, offering a peaceful and private retreat.Featuring 1,596 sq. ft. of living space, this home boasts a spacious open-concept layout with 2 bedrooms and 2 bathrooms. Recent updates include a new shingle roof (2024), new A/C unit (2025), and hot water heater (2023). The kitchen offers ample counter space and cabinetry, perfect for everyday living and entertaining.Enjoy plenty of storage throughout, along with sliding doors that lead to the porch—ideal for relaxing or hosting guests. The guest bedroom and bathroom are generously sized, while the oversized primary suite features a private ensuite bath complete with a double-sink vanity, garden tub, and walk-in shower.The laundry area is conveniently located in the spacious workshop and includes a washer, dryer, and utility sink. This home also features two porches—one screened and one enclosed—providing additional living space to enjoy year-round.Surrounded by mature landscaping, the property offers both charm and tranquility. Additional perks include an irrigation system and lawn maintenance already paid through February. This home has recently had a 4-point inspection.Brookhaven residents enjoy fantastic amenities including a pool, clubhouse, and shuffleboard—all with a low HOA fee of just $34 per month. Conveniently located near Hwy 27, shopping, medical facilities, and restaurants, you’re also just about an hour from Disney and 1.5–2 hours from both Florida coasts.Don’t miss your opportunity to own this beautiful home at 6561 Chinaberry Dr NE — schedule your private showing today!

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: Under Construction. New construction home with 2587 square feet two-story including 4 bedrooms with loft, 3.5 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, and a tiled shower. Bedrooms 3 and 4 share a jack-and-Jill bathroom. Plus, enjoy a 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty. “Please note, virtual tour/photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey."

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

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

Remarks: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.

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

Listing Agent: Chris Loschiavo (863-280-2201)

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: Welcome to this fully upgraded 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. Sellers are highly motivated!

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

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

Remarks: DON'T MISS THIS 3 BEDROOM 2.5 BATH HOME CENTRALLY LOCATED IN WINTER HAVEN, FL ON AN OVERSIZED (.39 ACRE) LOT WITH NO HOA!!! Featuring nearly 2,000 SqFt. of heated and cooled living space, this 2-owner home was constructed of BLOCK AND BRICK! The OPEN-CONCEPT, SPLIT BEDROOM PLAN, and CENTRALLY LOCATED KITCHEN share both privacy and convenience. There is plenty of natural light in the main living area and especially through the glass sliders leading to the back yard. In the event more privacy is preferred, just hit the remote button for the MOTORIZED BLINDS, which are also INCLUDED IN THE SALE. For those looking for an OVERSIED GARAGE, this one plenty of workspace for several different hobbies. There is no shortage of parking whatsoever on this HUGE CORNER LOT! Opportunity awaits at this lovely residence, which is located in close proximity to LEGOLAND, FL, medical, shopping, dining, schools, and the many freshwater lakes Winter Haven features. Winter Haven is also located between ORANDO INTERNATIONAL and TAMPA INTERNATIONAL AIRPORT, and the most recently added AVELO AIRLINE in LAKELAND, FL!!!

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

Listing Agent: Wanda Dicks (863-287-7846)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bathroom home situated on a desirable corner lot in Winter Haven. Conveniently located in the heart of Central Florida, Winter Haven is known for its Chain of Lakes, Legoland, local parks, shopping, dining, and easy access to both Orlando and Tampa. This property offers a functional layout with thoughtful updates throughout. The updated kitchen features quartz countertops, ample dark wood cabinetry, and a convenient breakfast bar. Recent improvements include tile flooring and an upgraded electrical panel, adding both style and peace of mind. The primary bedroom includes a walk-in closet, while the additional bedrooms provide flexibility for a variety of uses. Step outside to enjoy the large screened-in porch, ideal for relaxing or entertaining, all within a fully fenced yard with durable PVC fencing. The irrigation system is controlled by a Hydrawise WiFi system, allowing for easy and efficient lawn maintenance. Additional highlights include a 2-car garage, a circular driveway for added parking and convenience, and a roof replaced in 2018. With no HOA or CDD fees, this property offers added flexibility and fewer restrictions. Located near Winter Haven’s popular Chain of Lakes, as well as nearby shopping, dining, and major roadways, this home provides both comfort and accessibility.

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

Listing Agent: Garrett Robinson (863-838-5210)

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: Lovely 3-bedroom, 2-bath home with a 2-car garage located in the gated golf course community of Lake Bess Country Club in sunny Winter Haven, FL! Perfectly situated on the 9th fairway, this home offers breathtaking golf course views with no rear neighbors—providing both privacy and a serene backdrop. From the moment you arrive, you’ll appreciate the upgraded builder features, including a beautiful tile roof, separate garage entries, and lush, mature landscaping. Just a few doors down from the clubhouse and community pool, the location within the community is ideal. Step inside to cheerful, light-filled interiors with a welcoming open view straight through to the backyard. The thoughtfully designed floor plan includes a formal dining room, a spacious living area with vaulted ceilings, and a separate kitchen dinette complete with a built-in hutch. The screened lanai is the perfect place to enjoy Florida living year-round while taking in the peaceful golf course scenery. The oversized primary suite is privately located and features its own sitting area or study, creating a true retreat. The en suite bathroom offers a soaking tub, separate shower, water closet, and dual sinks in one large vanity, along with a spacious walk-in closet with ample storage. Elegant molding details throughout the home add a touch of sophistication. The kitchen is a chef’s dream, showcasing warm wood cabinetry, tile countertops, a coordinating backsplash, stainless steel appliances, and a built-in wine rack for added charm and functionality. On the opposite side of the home, you’ll find two spacious guest bedrooms and a well-appointed guest bathroom full of character. The indoor laundry room is conveniently located just off the kitchen and leads to the garage, which features a separate single garage door for added convenience. Additional updates include a new HVAC system (2024), and the washer and dryer are included with the sale. Monthly fees cover lawn maintenance (mowing, shrub trimming, fertilization, and weed control), access to the community pool and clubhouse, plus unlimited golf and use of the driving range—offering exceptional value and a true resort-style lifestyle. Conveniently located just minutes from Legoland, the interstate, Tampa and Orlando airports, Disney attractions, shopping, dining, medical facilities, and the Chain of Lakes—perfect for boating, fishing, or simply relaxing. This well loved home offers comfort, convenience, and incredible views—schedule your private showing today!

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

Listing Agent: John Manibusan (863-307-2792)

Remarks: Welcome to this beautiful fully renovated 3-bedroom, 2-bath home offering 1,485 square feet of stylish, move-in-ready living in the heart of Winter Haven, Florida. Every detail has been thoughtfully updated to deliver modern comfort and peace of mind. Enjoy brand-new doors and windows that fill the home with natural light, along with a completely new kitchen featuring contemporary finishes and new appliances—perfect for everyday living and entertaining. Both bathrooms have been fully renovated, offering fresh, modern design and functionality. New flooring throughout ties the home together with a clean, cohesive look. Adding even more value, a brand-new roof has been installed, providing long-term durability and confidence for the next homeowner. AC Replaced in 2020, Whole Home re-pipe with PEX and PVC/CPVC in 2020. Conveniently located near shopping, dining, schools, and Winter Haven’s renowned lakes, this turnkey property blends modern upgrades with Florida charm. Don’t miss the opportunity to own a fully updated home ready for immediate enjoyment.

Listing is courtesy of: DOWNTOWN REALTY (407-989-8881)

Listing Agent: Mark Rankin (407-989-8881)