Winter Haven Homes For Sale & Real Estate - 995 homes

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: SELLER MOTIVATED. MAKE OFFER! Looking for an affordable, move-in ready home under $250k with a fenced yard and no HOA in central Winter Haven? This updated 3-bedroom, 1-bath concrete block home offers 1,191+ square feet of easy living—plus a bright Florida bonus room and a private backyard that's fully fenced, perfect for pets, gardening, or relaxing outdoors. Inside, you'll find a modern kitchen with granite countertops, stainless steel appliances, open shelving, and deep teal subway tile that pops. The layout is open and airy with luxury vinyl plank floors, fresh paint, and natural light throughout. Major updates are already done for you—new roof (2023), updated electrical and panel (2023), PVC plumbing (2025), and a new tankless water heater (2025). There's also a detached shed with laundry and extra storage, plus room to park a boat, RV, or trailer—no HOA rules to worry about. Located across from public lakes and close to downtown Winter Haven, the Winter Haven Hospital, Polk State College, parks, trails, and transit, this home makes it easy to live, work, and play in one of the most walkable parts of town. If you've been searching for a 3-bed home with updates and a fenced yard near the heart of Winter Haven, 104 Avenue K NE is ready to welcome you home.

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

Listing Agent: April Spaulding (863-866-1044)

Remarks: Welcome to 1716 Terry Circle NE, Winter Haven, FL 33881, a beautifully maintained and fully furnished home offering the perfect blend of comfort, convenience, and investment potential. This move-in-ready property features ceramic tile flooring throughout, updated bathrooms, and a bright, open floor plan with spacious living and dining areas that flow seamlessly into a large kitchen with breakfast bar seating and all stainless steel appliances included. The thoughtfully designed layout provides privacy for the primary bedroom, separating it from the additional bedrooms to create a peaceful retreat. Tasteful furnishings and décor are included, making this a truly turnkey opportunity for homeowners, seasonal residents, or investors alike. The neutral color palette, abundant natural light, and functional layout create a warm and inviting atmosphere ideal for everyday living or entertaining guests. Adding to the home's value and peace of mind is a roof that is only five years old. One of the property's most attractive features is the absence of HOA fees and restrictions, offering greater flexibility and freedom for the new owner. Conveniently located in the heart of Winter Haven, the property is just minutes from LEGOLAND Florida Resort and Peppa Pig Theme Park Florida, making it an excellent choice for vacation home buyers and visitors. Residents will also enjoy easy access to the Winter Haven Chain of Lakes, offering endless opportunities for boating, fishing, and outdoor recreation. Nearby shopping, dining, schools, medical facilities, and the vibrant downtown district provide everything needed for comfortable Florida living. With convenient access to major highways connecting Orlando and Tampa, this fully furnished home presents a rare opportunity to own a turnkey property in one of Central Florida’s fastest-growing and most desirable locations. Showings will begin next week, so don't miss your chance to explore all that this exceptional home has to offer and schedule your private tour today.

Listing is courtesy of: EXIT REALTY 4CORNERS (863-344-3948)

Listing Agent: Carlos Dejesus (407-818-6868)

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: AROD PARTNERS REALTY (407-627-7621)

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

Remarks: Under contract-accepting backup offers. Better than new! Completely Remodeled! This 3 bedroom 2 bath home has been completely remodeled, to include a new a/c, new water heater, a beautiful new kitchen, new flooring, new lights & fixtures, and new paint, and the roof was replaced in 2023.

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Dwight Head (863-965-0207)

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)

Remarks: Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida — an updated and spacious 2 bedroom, 2 bath patio home tucked away on a quiet cul-de-sac street with no through traffic. A private walled walkway leads to a charming front porch with sitting area, creating a warm and welcoming approach. Step inside the foyer to discover a clean, updated interior offering more than 1,600 square feet of comfortable living space, highlighted by beautiful new flooring, a freshly painted interior, and a long list of thoughtful improvements. All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive, and easy-to-maintain property. The roof was replaced in 2020 for added peace of mind, and gutters have also been installed for convenience and functionality. The great room design creates a spacious and open feel, accentuated by built-in shelving and large glass sliders that bring in natural light while offering the perfect space to showcase personal décor and seasonal accents. Sliding glass doors open to the enclosed, air-conditioned Florida room, seamlessly expanding the living area and creating an easy indoor-outdoor lifestyle that can be enjoyed year-round. The great room also offers space for formal dining in addition to the casual eat-in area found within the kitchen. The generously sized kitchen features abundant real wood cabinetry, a large breakfast bar, closet pantry, and an inviting dining area ideal for casual meals and everyday living. The primary suite offers comfortable dimensions, a walk-in closet, and an en-suite bath complete with a tiled walk-in shower. The guest bedroom is also nicely sized and features its own walk-in closet along with convenient access to the full guest bathroom with tub and shower. Storage is abundant throughout the home with multiple interior closets, garage storage closets, and a spacious 2-car garage with laundry connections, helping keep everything neatly organized and out of sight. Additional features include an irrigation system and low-maintenance exterior living. Beyond the home, Cypresswood delivers one of Winter Haven’s most enjoyable golf community lifestyles. Residents enjoy access to the 18-hole championship golf course, originally opened in 1969 and designed by award-winning architect Ron Garl. Known for its rolling fairways and mature landscaping, the course also features a pro shop, driving range, putting green, and dedicated short-game practice areas. Just a short stroll from the home, residents can enjoy the recently refurbished junior Olympic-sized swimming pool, tennis courts, pickleball courts, and Wellness Center. The Cypresswood Pub & Restaurant serves as the social heart of the community, offering planned events, a full bar, great food, and live weekend music in a relaxed setting overlooking the golf course. Whether you are searching for a full-time residence, winter retreat, or low-maintenance golf community home, 460 Pinehurst Ct offers an exceptional opportunity to enjoy the Florida lifestyle in one of Winter Haven’s most established gated golf communities.

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

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

Remarks: Under contract-accepting backup offers. Offers should be submitted on the most recent/updated FAR-BAR As-Is contract & be accompanied by signed addenda (available via MLS attachment), as well as pre-qualification/approval letter or Proof of Funds. Customers are NEVER allowed on the property without their agent present. This includes showings, inspections, appraisals, etc. Lockbox and/or gate codes should NEVER be provided to customers. See attachments in MLS for information on the HOA/COA.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Oscar Allende Melendez (787-409-2175)

Remarks: Welcome to a home that offers more than just space — it delivers lifestyle, efficiency, and long-term value. Situated on a premium oversized corner lot, this 5-bedroom, 3-bathroom residence in Winter Haven is designed for those who appreciate both comfort and smart living. From the moment you enter, the clean, elegant tile flooring sets the tone for a modern and refined experience. The kitchen serves as the heart of the home, featuring soft-close cabinetry and elevated finishes — perfect for both everyday living and hosting guests. Step outside and envision your custom outdoor oasis. With hot and cold water lines already installed, your future outdoor kitchen is ready to come to life — ideal for entertaining and enjoying Florida living at its finest. But what truly sets this home apart is its fully paid-off solar panel system at closing — giving you immediate energy savings and a significant financial advantage from day one. Homes that combine space, upgrades, and built-in efficiency like this are rare. If you're looking for a move-in-ready property that delivers both lifestyle and smart investment value, this is one you don’t want to miss.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Oscar Allende Melendez (787-409-2175)

Remarks: Single wide mobile home situated on a spacious half acre double lot lot with two storage sheds offering plenty of extra storage space. Property is in need of repairs and updates. This is an ideal opportunity for investors, flippers, or buyers looking for a project. Plenty of potential to make it your own!

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

Listing Agent: Ben Becton (863-617-0232)

Remarks: Under contract-accepting backup offers. Check out this well-maintained 4-bedroom, 2-bath home featuring a desirable split floor plan, built in 2002 and situated on a spacious half acre fully fenced lot. The home offers vinyl plank flooring throughout, providing a modern look and easy maintenance. The roof was replaced just 3 years ago adding peace of mind for the next owner. The property is on septic, offering lower utility costs. Enjoy plenty of outdoor space for pets, entertaining, or future additions. Conveniently located close to public transportation, shopping, dining, and everyday amenities, this home offers both space and accessibility. A great opportunity for homeowners or investors alike.

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

Listing Agent: Katherine Montana - De Jesus (863-508-3000)

Remarks: Like-new 2022-built home on a desirable corner lot in the heart of 33884, located in a community loaded with amenities! This beautifully maintained 3-bedroom, 2-bath home offers modern living with an open, functional layout and split floorplan. A standout feature is the upgraded enclosed patio/all-seasons room, complete with windows and screens—perfect for relaxing year-round, entertaining guests, or enjoying Florida living without the bugs. The home shows like new and offers peace of mind with newer construction, while the community amenities add incredible value and lifestyle appeal. Conveniently located near shopping, dining, and everything Winter Haven has to offer. Move-in ready and priced to sell—don’t miss this one!

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

Listing Agent: Katherine Montana - De Jesus (863-508-3000)

Remarks: PRICE IMPROVEMENT! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home offers a modern split floorplan that provides privacy and functionality, perfect for everyday living or entertaining. The open layout creates a bright and airy feel throughout, with generous room sizes and excellent flow. Furniture is negotiable, making this a flexible move-in-ready opportunity for buyers. Enjoy outdoor living with a screened-in patio/lanai overlooking a fully fenced backyard—ideal for pets, play, or relaxing in privacy. Situated in a well-maintained community featuring a pool, playground, and clubhouse, this home offers both comfort and convenience. Enjoy the benefits of newer construction paired with desirable neighborhood amenities, all just minutes from shopping, dining, and major roadways. A great opportunity to own a nearly new home in a fantastic Winter Haven location.

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

Listing Agent: Katherine Montana - De Jesus (863-508-3000)

Remarks: Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and two private outdoor living areas. An attached two-car garage provides added convenience. Upstairs, you’ll find two spacious bedroom suites each with a private en-suite bath, as well as a versatile loft area. Step out to the screened balcony or the open upper deck, perfect for enjoying tranquil lake views and evening breezes. Community amenities include a swimming pool with spa, tennis court, lakeside dock, beach area, and a gated entry with electronic access. Whether you're seeking a seasonal retreat or a full-time residence, this unique property offers comfort, style, and a desirable location.

Listing is courtesy of: DREAM BUILDERS REALTY (407-847-5428)

Listing Agent: Tim Weisheyer (407-847-5428)

Remarks: Under Construction. This BEATIFUL ROBIE Model home has 5 bedrooms, 3 baths & a 2-car garage-2447 SqFt. NEWLY UPGRADED! Large 2-STORY open floor plan with Living & Dining room & Kitchen to entertain & enjoy the company of your guests. One bedroom located in the first floor, W/FULL BATH. Your very spacious master suite located on the 2nd floor with a large walk-closet & a double sink vanity with stall shower. This Home provides Stainless Appliances which include range, hood microwave, refrigerator, dishwasher and much more. We also provide Smart Home Technology which allows you to set the scene and connect to your home with your voice, from your smart phone, or through the smart panel interface. Your Smart Home comes with Alarm app, Echo Dot, Kwikset Smart Front Lock, IQ Panel, SkyBell, Z-Wave Thermostat, and a Z-Wave Light Switch. *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: Welcome to 207 Winter Ridge Blvd – A Serene Lakeside Retreat! This charming end-unit condo is a peaceful lakeview haven. Features; 2 spacious bedrooms, 2 bathrooms, and an open-concept living and dining area that flows effortlessly into an enclosed Florida room—ideal for soaking in breathtaking sunsets over Lake Conine. The kitchen features a built-in desk and a convenient closet pantry, while the master suite boasts a generous walk-in closet. Additional highlights include: Two dedicated parking spaces (one covered), brick paved front patio for outdoor enjoyment, high-end windows and doors, Hurricane shutters for peace of mind, new roof installed in 2024. Located within city limits, this quiet and well-maintained community offers resort-style amenities including a clubhouse, sparkling pool, shuffleboard courts, and access to a community dock and boat slip on Lake Smart. Whether you're fishing off the pier or strolling to nearby shops and restaurants in downtown Winter Haven, you'll love the blend of convenience & charm.

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

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

Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: Short Sale. Welcome to this beautiful Winter Haven home! Villamar This property offers a spacious layout, abundant natural light, and comfortable living areas ideal for everyday living and entertaining. The backyard provides great outdoor potential. Conveniently located near shopping, dining, schools, and major highways. Short Sale opportunity — perfect for buyers looking for value and investment potential.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Yoja Mirabal (407-543-7789)

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

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

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