Winter Haven Homes For Sale & Real Estate - 1041 homes

Remarks: Under contract-accepting backup offers. Welcome to this immaculately maintained 4-bedroom, 3-bathroom home with a spacious 3-car garage, perfectly situated in the highly desirable Country Club area of Northeast Winter Haven. Located within a gated community, this home offers both privacy and peace of mind. Backing up to an 11-acre jurisdictional wetland, the property provides complete rear privacy with a beautiful natural landscape—no rear neighbors, just serene views and tranquil surroundings. Inside, you’ll find a thoughtfully designed split floor plan with upgraded flooring, modern cabinetry, and stylish countertops throughout. The layout offers both functionality and comfort, ideal for those who love to entertain. Step outside to your private screened back porch retreat and fully fenced yard—perfect for relaxing evenings or weekend gatherings while enjoying the quiet, natural backdrop. This home truly combines luxury, privacy, and location—don’t miss the opportunity to make it yours.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Joshua Taylor (863-651-5471)

Remarks: LOOKING FOR THAT AMAZING HOME? Discover it in this fully renovated 3-bedroom, 2-bathroom beauty featuring a NEW roof (2025), NEW A/C unit (2026), NEW water heater (2025), and NEW electrical service panel (2026)—perfectly positioned just opposite Jewett Middle Academy. Enjoy your morning coffee on the radiant front porch before stepping into a bright and welcoming interior where the living room and kitchen greet you the moment you enter. The home is complemented by new vinyl flooring throughout and a cozy rug in the primary closet. The kitchen shines with a fresh, modern update, showcasing brand-new appliances, new cabinetry, and sleek quartz countertops. Whether you’re hosting guests or enjoying a quiet evening, the living room serves as the perfect centerpiece for everyday living. The primary suite offers a serene escape, highlighted by a fully remodeled ensuite bathroom and a spacious walk-in closet. The Fenced backyard is perfect for gatherings and outdoor enjoyment, with the added convenience of being close to shopping, schools, dining, and Winter Haven Hospital. Don’t miss this opportunity to own your happy place. Schedule your showing today

Listing is courtesy of: SUNSHINE LIFE REALTY LLC (321-229-0627)

Listing Agent: Sarita Khan (407-385-2077)

Remarks: Discover this beautifully remodeled home located in the desirable Jan Phyl Village community. This property offers the perfect combination of comfort, functionality, and space to enjoy Florida living. The home features 3 bedrooms, 2 bathrooms, a cozy wood-burning fireplace, and a versatile bonus room that can be adapted to fit a variety of needs. The interior provides a warm and inviting atmosphere filled with natural light. Step outside to enjoy a private pool and a fully fenced backyard, ideal for entertaining, relaxing, or enjoying the Florida sunshine. The property includes two lots, offering added privacy and flexibility for future possibilities. Conveniently located near shopping, dining, entertainment, and everyday conveniences. With no HOA restrictions, this property offers greater flexibility for both homeowners and investors. A wonderful opportunity to own a move-in-ready home in a prime Winter Haven location.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Julimar Barreiro Pastrana (407-590-8604)

Remarks: Virtually Staged. Beautifully remodeled in 2024, this move-in ready home offers modern updates, energy efficiency, and timeless comfort—all with no HOA. Step inside to an open-concept floor plan featuring high ceilings and abundant natural light. The brand-new kitchen impresses with contemporary finishes, while the updated bathrooms offer a fresh, stylish feel. A desirable split floor plan provides added privacy, making the home ideal for both families and guests. Major improvements include a newer roof and full re-plumbing, giving peace of mind for years to come. The home is also equipped with solar panels for low-cost energy, along with a natural-gas stove and gas water heater—perfect for efficiency and everyday convenience. Outside, enjoy great curb appeal, a fully fenced backyard for pets or play, and a spacious attached 2-car garage. With no HOA restrictions, you have the freedom to personalize, park, and use your property exactly the way you want. This beautifully updated home truly checks every box—style, function, efficiency, and freedom.

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

Listing Agent: David Small (407-601-8351)

Remarks: Under contract-accepting backup offers. Calling all investors, flippers, landlords, and buyers looking for an affordable property with room to add value. Home was previously rented at $1150 in the current condition and could easily bring in $1500 with completed renovations. NO SIGHT UNSEEN OFFERS!!! Situated on a generously sized lot shaded by mature trees, this charming bungalow-style home is full of potential and ready for its next chapter. As you arrive, you'll appreciate the spacious lot, long driveway, and inviting covered front porch that adds to the home's timeless appeal. A major improvement has already been completed with a newer roof installed in 2026 featuring hurricane clips, along with a newer water heater, which may help reduce homeowners insurance costs. The seller is also including two brand-new window A/C units (see photos). Inside, you'll find a functional layout featuring a living area, eat-in kitchen, two bedrooms, and one bathroom. The home offers a solid foundation for renovations and personal touches, providing an excellent opportunity to create value and maximize its potential. The home will require a new kitchen , bath, flooring, and cosmetic work. One of the property's standout features is the expansive backyard, offering plenty of room for gardening, entertaining, pets, storage, or future improvements. Large lots like this are becoming increasingly difficult to find at this price point. The lot is also mostly fenced. The property is being sold as-is and will require repairs and updates. Buyers are encouraged to independently verify the condition and functionality of all appliances and systems. If you're searching for an affordable property with a large yard, key capital improvements already completed, and excellent upside potential Conveniently located just minutes from Winter Haven's Chain of Lakes, shopping, restaurants, medical facilities, parks, downtown Winter Haven, and major transportation routes, this property provides easy access to everything Central Florida has to offer.

Listing is courtesy of: COLDWELL BANKER REALTY (813-289-1712)

Listing Agent: Christopher Copenhaver (813-786-9224)

Remarks: Recently refreshed home in Central Florida featuring luxury vinyl flooring, fresh interior paint, redesigned kitchen and bathrooms, a spacious backyard, and a single-car garage. This property offers a great opportunity for those looking to transition toward homeownership with flexible options available. Conveniently located and ideal for buyers looking for space, updates, and long-term potential. Contact for additional details and showing availability.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Chad Lindsey (863-660-7837)

Remarks: Under contract-accepting backup offers. Under Contract. Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets, eat-in kitchen & gas oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting,pvc plumbing, irrigation well/pump, pole barn for RV parking 28x20’, carport, brand new hot water heater, enclosed concrete outside laundry room. This home offers updated plumbing and abundant parking. Pride of Ownership. A must see!

Listing is courtesy of: WATSON & WATSON INC REALTORS (863-294-4149)

Listing Agent: Wendy Gibbs (863-557-5249)

Remarks: Brand-new, 3-bedroom home for sale! Say hello to life in the Sophia, featuring an open living area with luxury vinyl plank flooring, under an airy volume ceiling! Unwind in your spacious owner's suite complete with a private en-suite bath including a decorative tiled shower, dual vanities, a convenient linen closet, and a walk-in wardrobe! Plus, enjoy outdoor living on your covered lanai! This home includes features and finishes hand-selected by our professional designers to provide you with enduring style, move-in convenience, and easy home maintenance: Beautiful, open kitchen with: A counter-height island Quartz countertops 36-in. shaker-styler cabinets with crown moulding and decorative knobs/pulls Stainless steel undermount sink with a pull-down faucet Walk-in pantry Samsung stainless steel appliances: 5-burner smooth-top electric range with wi-fi smart controls Fingerprint-resistant microwave with ventilation system ENERGY STAR® quiet-operation dishwasher ENERGY STAR® side-by-side refrigerator Low-maintenance luxury vinyl plank flooring throughout the living areas, kitchen, laundry room and all bathrooms Mohawk stain-resistant carpet in all bedrooms Energy-efficient LED lighting in the kitchen and gathering room Custom-fit 2-in. faux wood window blinds Built-in pest control Architectural shingles with limited-lifetime warranty Fully sodded with Florida-friendly landscaping and irrigation system ...and much more! Save on utilities with energy-efficient R-30 insulation, foam-injected block insulation, double-pane Low-E windows, and a programmable thermostat.

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

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

Remarks: USDA financing may be available for qualified buyers, potentially allowing 100% financing with no down payment. Buyers should verify eligibility with their lender. Welcome to your slice of country living with room to breathe! Situated on approximately 0.65 acres, this well-maintained 3-bedroom, 2-bath home offers the perfect blend of privacy, functionality, and convenience. Step inside to find comfortable living spaces designed for everyday living and entertaining. Outside, the possibilities are endless. The oversized lot provides ample space for gardening, pets, recreational vehicles, boats, or simply enjoying the Florida lifestyle without the restrictions often found in subdivision communities. One of the standout features is the large detached metal building/workshop, offering incredible flexibility for hobbyists, contractors, mechanics, small business owners, or anyone needing additional storage space. Whether you’re looking for a workshop, home business setup, equipment storage, or the ultimate man cave, this structure adds tremendous value and versatility. Enjoy the peace and quiet of a larger homesite while remaining just a short drive from shopping, dining, schools, medical facilities, and major commuter routes. If you’ve been searching for a property with space, freedom, and a workshop that’s hard to find in today’s market, this is one you won’t want to miss.

Listing is courtesy of: MILLSHIRE REALTY (863-815-8000)

Listing Agent: Robert Miller, Jr (863-899-9324)

Remarks: Honey, stop the car! This home truly has it all. Featuring 5 bedrooms, 4 full baths, a spacious loft, and a 3-car garage, this property offers room for everyone. Your 68,132 sq. ft. homesite (1.56 acres) is a little piece of heaven—flat, open space with no rear neighbor, perfect for privacy and endless possibilities. Inside, you’ll find an entertainer’s paradise: a double oven, a kitchen sink plus an additional prep sink in the island, two corner pantries, and over 3,000 sq. ft. of living space to spread out and enjoy. Outside, there’s ample parking for guests and a charming front porch where you can relax and watch the clouds go by.

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Paul Shearn (407-713-2127)

Remarks: One or more photo(s) has been virtually staged. Welcome to 718 Eagle Landing Blvd, a home that instantly feels peaceful, private, and easy to love. Built in 2023 and perfectly positioned on one of the best lots in the community, this home offers something buyers are always hoping to find but rarely do at this price point: beautiful open green space behind the home with no rear neighbors. No back windows staring into yours. No boxed-in feeling. Just quiet views, extra privacy, and room to breathe. From the moment you arrive, the home feels fresh, clean, and cared for. Recently refreshed with fresh interior paint, pressure washing, updated landscaping, and new mulch, it is truly move-in ready and shows beautifully. Inside, natural light fills the open-concept floor plan, creating a bright and welcoming space that feels comfortable the second you walk in. The layout is modern, functional, and easy to live in, with open living and dining areas that are perfect for everyday life, family time, and entertaining. The kitchen flows effortlessly into the main living space, making it easy to stay connected whether you are cooking dinner, hosting friends, or enjoying a quiet night at home. The spacious primary suite is tucked away as a private retreat, featuring dual closets and a large walk-in shower. The additional bedrooms offer flexibility for guests, family, a home office, playroom, gym, or hobby space. But the backyard is where this home truly separates itself. With peaceful open views and no rear neighbors, this lot gives you the kind of privacy and possibility that makes a house feel like home. Imagine morning coffee outside, weekend barbecues, a future pool, a garden retreat, or simply enjoying the quiet without looking directly into another home. Rear fencing is permitted, giving the next owner even more freedom to create the outdoor space they have been dreaming of. Located in a growing and convenient area near shopping, dining, the Chain of Lakes, LEGOLAND Florida Resort, and the future SEA LIFE Florida Aquarium, this home offers the perfect combination of newer construction, privacy, location, and long-term potential. Homes like this do not come around often, especially newer homes on premium lots with no rear neighbors. Schedule your private showing today and experience the privacy, space, and move-in-ready feel this home has to offer.

Listing is courtesy of: M2M REALTY (407-401-2275)

Listing Agent: Micaela Navarra (407-761-5501)

Remarks: Pool pump replaced in 2026, hot water tank and HVAC unit 5 years old, 10 year old roof! Welcome home to this well-maintained 3-bedroom, 2-bath plan offering 1,666 square feet living on over a 1/2 acre of land, and no HOA!!! The desirable split floor plan provides privacy and functionality, while the spacious living area is perfect for everyday living and entertaining. The kitchen comes complete with all appliances, indoor central vacuum system, and the home includes a security camera system for added peace of mind. Step outside to enjoy the large screened lanai overlooking a sparkling in-ground saltwater pool, complete with a solar heating system to extend your swimming season. Bring all your toys-there is plenty of parking, including a large camper/RV carport 29x11 and an additional storage shed. The fully fenced backyard offers privacy and ample space for pets, outdoor activities, and family gatherings. Conveniently located and move-in ready, this property combines comfort, flexibility, and outdoor enjoyment without the added expense of HOA fees. Schedule your private showing today!

Listing is courtesy of: GOLD HEART REALTY LLC (863-224-2419)

Listing Agent: Lori Roberts (863-224-2419)

Remarks: Welcome to this spacious and well-maintained villa in Cypresswood Golf & Country Club, offering comfortable living in one of Winter Haven's established gated golf communities. Please note: The professional photos currently showing blue carpet were taken before the recent flooring update. New flooring has now been installed in the living room, dining room, kitchen, hallway, and Florida room. Inside, you'll find an oversized living area filled with natural light, a functional kitchen with ample cabinet space, generously sized bedrooms, and an enclosed Florida room that provides valuable additional living space. The new flooring gives the main living areas a fresh, updated look while maintaining the home's warm and inviting feel. The home has been lovingly cared for over the years and offers a wonderful opportunity for its next owner to move right in or personalize it to their own style over time. The split-bedroom floor plan provides privacy and flexibility, while covered parking and low-maintenance exterior living make everyday life easy and convenient. Residents of Cypresswood enjoy access to golf, tennis, a clubhouse with restaurant, and beautifully maintained grounds, all just minutes from shopping, dining, medical facilities, and major roadways. If you've been searching for space, value, and a relaxed Florida lifestyle in a gated golf community, this home deserves a spot on your must-see list.

Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)

Listing Agent: Darin Dobson (407-947-6773)

Remarks: Your perfect home with a Poolside Paradise Awaits! This stunning five-bedroom, three-bathroom home boasts an inviting screened-in pool area, perfect for relaxation and entertainment. Nestled in a prime location with convenient access to Highway 27, this residence offers an exceptional living experience that blends elegance and practicality. As you step through the impressive double door entry, you’ll be greeted by an expansive open floor plan that invites you to explore. The luxury vinyl plank flooring flows seamlessly throughout the main living areas, while plush carpeting in the bedrooms and sleek tile in the bathrooms add just the right touch of warmth and style. High ceilings adorned with double crown molding elevate the ambiance, making each room feel spacious and airy. A formal dining room and living room provide elegant spaces for entertaining, while the eat in kitchen offers a cozy spot for casual meals. The thoughtful split bedroom plan, provides both privacy and convenience. At the heart of this home lies a large open kitchen that’s sure to delight both casual cooks and culinary aficionados alike. Featuring beautiful granite countertops and a massive island that comfortably seats six, this kitchen is perfect for entertaining friends and family. The sleek black stainless appliances add a modern flair, ensuring both functionality and style. The primary bedroom is a true retreat, flooded with natural light from its abundant windows and featuring sliding glass doors that lead you directly to the covered deck and your gorgeous pool area. The en suite bathroom is a sanctuary of relaxation, boasting a luxurious garden tub, a stand-up shower, and a walk-in closet equipped with thoughtful built-ins for all your organizational needs. Step outside, and you'll discover your private paradise! The screened pool area is a stunning highlight of this home, featuring a serene water feature fountain and a built-in table with stools under a charming tiki umbrella ideal for sunny afternoons and casual gatherings. The saltwater pool is heated for year-round enjoyment and includes a safety child fence for peace of mind. As the sun sets, the marine-grade privacy curtains and LED lighting create an enchanting atmosphere for evening swims and entertaining. Additionally, the back patio is thoughtfully plumbed and wired for an outdoor kitchen, making it an ideal spot for summer barbecues and family gatherings. The entire backyard is securely enclosed with a durable vinyl fence, ensuring privacy and a safe space for little ones and furry friends to play. Adding even more value, the property includes a dedicated irrigation meter for the lawn, allowing the irrigation system and exterior water hose conveniently located beside the water softener to operate without sewer charges from the city. In addition to its many impressive features, this home is equipped with solar panels, offering an eco-friendly energy solution that can significantly reduce your utility costs. The current lease is assumable, with a monthly payment of just $145 and an approximate balance of $20,000. This means you can enjoy the benefits of renewable energy without the upfront costs typically associated with solar installations. It's a fantastic opportunity to embrace sustainability while potentially lowering your monthly expenses—an ideal complement to this already remarkable home! This property is an ideal blend of comfort, modern upgrades and outdoor living, making it a must see!

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

Listing Agent: David Small (407-601-8351)

Remarks: Welcome to 7902 Waterview Way, a beautifully maintained low-maintenance condo nestled within a desirable gated community. Offering a perfect blend of comfort and convenience, this home features tasteful upgrades, modern finishes, and a functional layout designed for easy everyday living. Enjoy a carefree lifestyle with exterior maintenance taken care of while taking advantage of the community's exceptional amenities, creating the perfect setting to relax or stay active. Ideally located near shopping, dining, entertainment, and major roadways, this move-in-ready condo offers the perfect opportunity to enjoy low-maintenance living in a secure and welcoming neighborhood.

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

Listing Agent: Kimberly Cabrera (863-398-4008)

Remarks: Welcome to this beautifully maintained 2 Bedroom 2 Bath home offering the perfect blend of comfort, style, and functionality. A transferable warranty covers your 2.5 ton Carrier A/C unit until 2035! From the moment you arrive, you’ll appreciate the inviting curb appeal and thoughtfully designed layout. Inside, you’ll find spacious living areas filled with natural light & generously sized bedrooms designed for everyday living and entertaining alike. Step outside and discover one of this home’s standout features — a fully equipped 1,500 sqft man cave/workshop in the backyard complete with its own powerful 5-ton A/C unit, and full bath making it the perfect space for entertaining, hobbies, a game room, home gym, or additional workspace year-round. Or a possible income opportunity! Conveniently located near shopping, dining, schools, and major roadways, this home combines peaceful living with everyday convenience. Whether you’re a first-time buyer, growing family, or looking for your next investment opportunity, this property is one you won’t want to miss. Schedule your private showing today!

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

Listing Agent: Candice Knoll (863-608-5114)

Remarks: Virtually Staged. This home offers the perfect blend of comfort, convenience, and modern living in one of Winter Haven's growing communities. Built in 2019 with solid construction, the thoughtfully designed open floor plan creates a natural flow between the living, dining, and kitchen spaces, making everyday living and entertaining feel effortless. Step inside and imagine mornings filled with natural light, evenings spent gathering with friends, and the ease of a home designed for today's lifestyle. A dedicated laundry area helps keep daily routines organized, while the attached two car garage provides plenty of space for parking, storage, or weekend projects. An affordable Homeowners Association adds to the home's overall value. Located between Tampa and Orlando, this property offers convenient access to major employment centers, entertainment, and travel while allowing you to enjoy the relaxed atmosphere that makes Winter Haven so appealing. Spend weekends exploring the renowned Chain of Lakes, visiting nearby LEGOLAND Florida Resort, or discovering local parks, dining, and outdoor recreation. Everyday conveniences are just minutes away, including Publix, Walmart, medical facilities, Polk State College, shopping, restaurants, and a variety of essential services. With easy access to major roadways, commuting and exploring Central Florida is simple. Whether you are searching for a home that combines modern comfort with everyday convenience, this property is ready to welcome you.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Stacey Vazquez (407-874-5751)

Remarks: NEW PRICING!! FRESH INTERIOR PAINT July 2026, NEW INSTALLED ROOF July 2026, NEW AC UNIT INTERIOR AND EXTERIOR June 2026 NEW APPLIANCES 2026, KITCHEN FAUCET JUNE 2026. Discover the potential in this charming 3-bedroom, 2-bath home nestled within a gated Winter Haven community. Offering 1,303 square feet, this property features a unique side-entry front door connected by a private walkway, creating added character and curb appeal. Enjoy the comfort of an established neighborhood with long-term residents and a welcoming community feel. Conveniently located just minutes from Walmart, shopping, dining, entertainment, and Legoland, this home offers both location and opportunity. Residents also enjoy access to the community pool. Priced to sell and ready for your personal touch!

Listing is courtesy of: NEWBERRY REALTY & DEV GRP INC. (321-607-2354)

Listing Agent: Gylwerd Sevilla Oviedo (305-989-7853)

Remarks: Under contract-accepting backup offers. Come and make this move-in ready three-bedroom, two-bathroom home your own in Central Pointe! The interior features two spacious living areas with vaulted ceilings and plenty of natural light, creating an airy atmosphere. The main living areas flow seamlessly with the kitchen and dining area, perfect for everyday living and entertaining. The primary bedroom offers ample storage space with a large walk-in closet and beautifully updated ensuite with large soaking tub and walk-in shower. Step outside to enjoy the privacy of a fully fenced-in backyard that overlooks serene waterfront views. Conveniently located near shopping, restaurants, schools, and medical facilities, this home also provides quick access to major highways for an easy commute to Tampa or Orlando. Schedule your private showing today!

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

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

Remarks: PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy the view from your Screened Porch. The Home is located close to Shopping (New Publix), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!

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

Listing Agent: David Shippey (863-521-4517)