Winter Haven Homes For Sale & Real Estate - 1041 homes

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

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

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

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

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

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

Remarks: 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: 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: 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: 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: 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: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully updated three-bedroom, two-bathroom home with a two-car garage, offering 1,866 square feet under roof in the desirable community of Winter Haven. From the moment you arrive, you’ll appreciate the freshly painted exterior and updated landscaping that create strong curb appeal, setting the tone for what awaits inside. Step through the front door into a bright and refreshed interior featuring newly painted walls, updated doors, and modern light fixtures. The great room is highlighted by new luxury vinyl plank flooring that continues into all bedrooms, offering both durability and a clean, contemporary feel. The kitchen is designed for both functionality and style, featuring brand-new stainless-steel appliances and a seamless flow into the main living space—perfect for everyday living and entertaining. The split-bedroom layout provides privacy, with a spacious primary suite that includes updated mirrors and finishes in the en suite bathroom. Two additional bedrooms and a second full bath offer flexibility for family, guests, or a home office. Throughout the home, you’ll find new ceiling fans, updated blinds for window treatments, and thoughtful upgrades that make this home truly move-in ready. Additional improvements include a Brand-new roof, new hot water heater, and a freshly painted garage floor, adding both value and peace of mind. Located in a sought-after area of Winter Haven, this home offers convenient access to shopping, dining, and local attractions, while still being tucked into a welcoming community known for its charm and proximity to the area’s beautiful lakes. This is a fantastic opportunity to own a fully updated home in one of Central Florida’s most desirable and growing locations.

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

Listing Agent: Jason Stone (863-838-8972)

Remarks: Located just minutes from the beautiful Chain of Lakes, public lake access, parks, restaurants, and the vibrant recreational areas of Winter Haven, this property offers both convenience and lifestyle. This 3-bedroom, 2-bath home features a very spacious kitchen with eat-in area, inside laundry, and an oversized family room that offers excellent flexibility and can easily be used as a guest space, office, or potential extra bedroom. Major updates include a metal roof, HVAC replaced in 2023/2024, and water heater from 2015. Currently tenant-occupied, this property also presents an immediate income-producing opportunity for investors or buyers looking for cash flow from day one.

Listing is courtesy of: MBA REALTY GROUP, INC (407-291-4665)

Listing Agent: Paola Arias (407-969-9211)

Remarks: PRICE ADJUSTMENT***Don't Miss This Opportunity! This home offers amazing potential and features 4 bedrooms and 1 full bath, making it ideal for homeowners or investors. The kitchen is just off from the spacious dining area, great for family gatherings, while the spacious living room and family room provides extra space to relax. The primary bedroom as well as the other rooms are generously sized, offering a built-in closets. This home is a great candidate to be transformed into your ideal living space or added to your rental portfolio. Property is being sold As-Is. All buyers MUST view the home in person before submitting an offer. Opportunities like this don't last long, schedule your showing today before it's gone! ** FURNISHINGS, WASHER, DRYER, OR REFRIGERATOR DOES NOT CONVEY WITH THE SALE OF HOME.

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

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: Welcome to this well-located single-family home situated in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 4 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living, along with a 2-car garage and a large driveway. The property also includes a newer shingle roof (2023) and newer LVP flooring. Inside, the living area offers two living room areas, one at the entrance and another one by the kitchen, creating a welcoming space that makes it easy to stay connected whether you’re relaxing at home or entertaining guests. The bedrooms are nicely sized, and the primary suite provides added comfort with a walk-in closet and a private bathroom that features both a bathtub and a separate shower. The second full bathroom add convenience and functionality for the household. Whether you’re searching for a place to make your own or an investment opportunity, this home is worth a look. Schedule your showing today.

Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)

Listing Agent: Gabriel Silva Andrada (321-666-0301)

Remarks: Under contract-accepting backup offers. Located off the southwest side of Rifle Range Rd in Winter Haven, with easy access to Bartow, this property offers a quiet setting with plenty of potential. The existing mobile home has an approximately six-year-old roof and will benefit from updates, including subfloors and AC. Showings of the home are by appointment with an agent. Two additional structures on site offer added storage or future possibilities. No HOA. Buyers and buyer’s agents should verify all measurements, site details, land use, and tax information.

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

Listing Agent: Lorena Alvarez Cordero (863-412-9288)

Remarks: ALMOST PARADISE! Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a study, library and/or den), family room and interior laundry room. Note the Curb Appeal of the landscaping, TILE ROOF and BRICK paver driveway and walkway! The inviting and covered front porch provides respite from inclement weather. As you enter the entry foyer, the living room will be to the immediate left and the dining room to the right. Straight ahead is the family room with a set of sliding glass doors that opens onto the screened in lanai. Settle back, listen to the birds singing and observe the cows on the adjacent ranch property! To the left of the family room are bedrooms #2 and #3 and to the right is the kitchen, dining nook, primary bedroom suite, bedroom #4 and the laundry room! The well planned kitchen has a breakfast bar, white cabinetry with neutral colored solid countertop and stainless steel appliances. The kitchen appliances have been updated from 2018-2025. The spacious primary suite has sliding glass doors leading to the lanai, two walk-in closets and an ensuite bathroom with dual vanities and sinks, jetted tub, separate shower and a water closet! Bedroom #4 is currently used as a home office. The floor plan allows creativity in use. Most recent updates include: Water Heater replaced Feb. 2026; AC/Heat system April 2025; garbage disposal and microwave 2025; and lanai screen & door 2025. The PERIMETER 90 X 120 lot is a generous in size. There is room to add a pool, outdoor kitchen, play area and/or garden! The HOA fee provides re-use irrigation water and maintenance of the gate and common areas. Perfect for a year round or winter residence, this home is a blank canvas just waiting for YOUR decorating touches! For those who enjoy golf and/or tennis, the Country Club of Winter Haven is just 2 Blocks away! Publix Supermarket is conveniently located within 0.8 mile with additional stores and a bank currently under construction! Easy access to downtown Winter Haven, HWY 27 and I-4. Legoland, Bok Tower, world-famous theme parks of Disney, Universal Orlando, Sea World, water adventure parks, downtown Orlando and various other nature parks are within a 7 to 60 mile drive. Be sure to make your appointment to view this outstanding property! Measurements are approximate. All information is believed to be accurate but not guaranteed.

Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)

Listing Agent: Carol Jean Sheil (863-412-3801)

Remarks: The property you are viewing is comprised of four individual parcels all being sold together. Also see MLS B4901531. This property has two parcels with single family homes on it , two vacant parcels, and easement parcel. The two single family homes are both concrete block built, 2 bedrooms and 1 bath room The entire sale parcel is almost 1 acre. These parcels are zoned RL 3 but have the potential to have a future land use zoning change. The corner lot sits across from a commercial store. Located on the corner of Eagle Lake Loop and Rifle Range road this area is rapidly growing with both residential and commercial opportunities. Property location has great opportunities for potential land use change based on surrounding parcels.

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

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

Remarks: Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: Welcome home to this beautifully updated 3-bedroom, 2-bath residence ideally situated in the heart of Winter Haven, just minutes from downtown and surrounded by the area’s picturesque lakes. This move-in ready home has been thoughtfully upgraded throughout, offering stylish vinyl flooring, refreshed bathrooms, modern light fixtures, and a beautifully renovated kitchen featuring granite countertops, updated cabinetry, a trendy backsplash, and stainless steel appliances. The inviting living room is anchored by a cozy fireplace, creating the perfect space to relax or entertain. Step outside to your private, fully fenced backyard complete with a fire pit—ideal for enjoying Florida evenings with family and friends. Additional highlights include a spacious two-car garage with laundry area, a convenient enclosed storage space, and a newer roof (2022) for added peace of mind. With no HOA and a prime location close to shopping, dining, and everything downtown Winter Haven has to offer, this home truly combines comfort, style, and convenience. Don’t miss your chance to make it yours!

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

Listing Agent: Robert Johnson (813-364-2250)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! Retreat to your primary suite that is conveniently situated in the back of the home for plenty of privacy and features a huge walk-in closet. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home providing plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open and airy atmosphere. The eat-in kitchen is a standout with new custom cabinetry, granite countertops, and a convenient closet pantry. Flooring throughout the home includes durable laminate and ceramic tile, with cozy carpeting in the third bedroom. The primary suite offers sliding doors to the patio, a generous walk-in closet, and an updated bathroom. The secondary bedroom also includes a walk-in closet, while the third bedroom features patio access and a European-style A/C unit. Major updates include a roof replacement in 2022, and a new A/C system installed in 2019. Covered parking adds convenience. Enjoy resort-style living with scenic golf course views and access to community amenities, all just minutes from shopping, dining, and major roadways. Whether you're seeking a year-round residence or a seasonal escape, this villa is the perfect place to call home. Community pool, tennis, clubhouse & restaurant.

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

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

Remarks: Welcome to your turn-key Florida retreat! This beautifully reimagined home is a masterclass in modern updates and serene living, nestled within a tranquil, established community. From the moment you arrive, the vibrant curb appeal and crisp, clean lines signal a home that has been maintained with pride. The heart of the residence is an open, sun-drenched kitchen featuring premium stainless-steel appliances, sleek cabinetry, and chic subway tiling—perfect for the culinary enthusiast or the frequent entertainer. With durable wood-look flooring and a versatile, oversized utility suite, this home seamlessly blends style with everyday functionality. Beyond the interior, your private oasis awaits. Relax on the expansive screened-in porch or take advantage of the massive, fully fenced backyard—a rare find that offers limitless potential for a pool, garden, or workshop. The long driveway and integrated carport provide plenty of space for your vehicles and toys, making this the perfect home base for a Central Florida lifestyle. Whether you’re a first-time buyer or a savvy investor looking for a high-quality asset, this property offers an optimistic outlook and incredible value. Opportunity is knocking—book your showing today and claim your piece of paradise!

Listing is courtesy of: MCO REALTY (407-479-8601)

Listing Agent: Vernel Smith (863-224-1942)