Winter Haven Homes For Sale & Real Estate - 866 homes

Remarks: Beautiful two-story single-family home built in 2023. Featuring a modern and functional design, this home offers 5 bedrooms and 3 full bathrooms, spread across 2,284 square feet of living space. The ground floor includes a spacious living room, a kitchen equipped with modern appliances (refrigerator, washer, dryer, dishwasher, and more), and a bedroom with a full bathroom, ideal for guests or as an office. The second level features the remaining bedrooms, including the master suite, which is equipped with a walk-in closet. Interior finishes feature ceramic and carpet flooring, thermal windows with blinds, and a central electric HVAC system. The property includes an attached two-car garage and sits on a 5,500-square-foot lot. Located in the Canton Park community, with low HOA fee and not CDD. This home represents an excellent opportunity for those seeking comfort and style in a prime location close to Tampa, Orlando and Lakeland. More pictures coming soon.

Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)

Listing Agent: Brigida Lopez (321-945-3989)

Remarks: Welcome to Garden Grove Oaks – a friendly, active 55+ community in beautiful Winter Haven and you OWN THE LAND! This well-maintained 2-bedroom, 2-bathroom manufactured home with a bonus office/den and Florida room offers the perfect blend of comfort, functionality, and easy Florida living. Step inside and you’ll immediately appreciate the bright, open layout, featuring a spacious living area ideal for relaxing or entertaining. The kitchen provides ample storage and prep space, while the adjoining dining area creates a natural flow for everyday living. Outside, you’ll enjoy a low-maintenance yard, covered parking, and plenty of room for outdoor seating. Garden Grove Oaks residents love the clubhouse, community pool & hot tub, social activities, and peaceful setting, all while being close to shopping, dining, medical facilities, and the best of Winter Haven. Whether you’re seeking a seasonal retreat or a year-round home, this charming property is move-in ready and waiting for you!

Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)

Listing Agent: Nicole Castro (863-547-5647)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2-bath home located in the desirable community of Winter Haven! Built by the reputable local builder Southern Homes, this residence showcases quality craftsmanship and thoughtful design throughout. This spacious split floor plan offers both privacy and functionality, ideal for everyday living and entertaining. Step inside to find soaring ceilings in the main living area, creating an open and airy feel that enhances the home’s natural light and livability. The large kitchen provides ample space for cooking and gathering, with tile flooring that extends through the kitchen, dining area, laundry room, and both bathrooms for durability and easy maintenance. The primary suite serves as a true retreat, featuring a tray ceiling with elegant crown molding, two walk-in closets, and a well-appointed en-suite bathroom. The primary bath includes a dual vanity, relaxing garden tub, and a separate step-in shower, offering both comfort and convenience. Additional interior highlights include indoor laundry and well-sized secondary bedrooms that provide flexibility for guests, family, or office space. Outside, enjoy a screened-in covered lanai overlooking a fully fenced backyard—perfect for entertaining, pets, or quiet evenings outdoors. The front landscaping has been freshly updated just in time for spring, giving the home outstanding curb appeal while maintaining a move-in ready interior. The garage is a standout feature, offering an epoxy-coated floor, an extra-long extension for added space, and a convenient man door for easy access. All information and property details are deemed reliable but not guaranteed and Buyer/Buyer's Agent is responsible for their own due diligence including but not limited to verifying HOA, Community Info, Rules, Leasing Requirements, Sqft, Lot Size, Room Dimensions, and Taxes.

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

Listing Agent: Ashli Smith (863-248-9438)

Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept floorplan, perfect for entertaining or just hanging out, is complemented by stylish luxury vinyl plank flooring. The kitchen and throughout the home feature elegant quartz countertops, while the stainless-steel appliances and smart thermostat with voice control add a touch of modern technology. The laundry room features a new washer and dryer and is conveniently located upstairs with all the bedrooms. The owner’s suite is situated at the back of the home with a spa-like owner’s bathroom and spacious walk-in closet. Completing this home is beautifully designed landscaping curated for the Florida lifestyle. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Beautifully maintained home located in the sought after community of Mandolin. This generous open floor plan is great for entertainment.

Listing is courtesy of: ILLUSTRATED PROPERTIES LLC (CO (561-626-7000)

Listing Agent: Cheryl Rubman (954-254-1844)

Remarks: One or more photo(s) has been virtually staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a layout that stands out from the rest. Offering high ceilings and a well-designed flow from the L-shaped formal living room that transitions into the formal dining area, creating a defined yet open feel. The kitchen sits at the center with a dinette overlooking the family room. A standout feature is the seamless connection to the outdoor space, with three separate access points to the 33x10 screened-in lanai, from the dinette, formal dining area, and primary suite—creating true indoor-outdoor living. The kitchen has been tastefully updated with brand new granite countertops, new range, and new microwave, along with ample cabinetry, a closet pantry, and breakfast bar. The primary suite is generously sized and opens into an en-suite featuring dual walk-in closets, split vanities, a garden tub, walk-in tile shower, and a private water closet. The split-bedroom floor plan offers privacy, while all bedrooms include walk-in closets. Recent improvements make this one stand out from others in the neighborhood, including brand new carpet throughout, fresh interior paint, and a new water heater, giving buyers peace of mind from day one. Located in the gated Ruby Lake community in Southeast Winter Haven, just minutes from convenient access to shopping, dining, Publix, Walmart, Legoland, and Hwy 27 for an easy commute.

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

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

Remarks: Under contract-accepting backup offers. PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings. Inside, you'll love the bright, open layout with 10' ceilings, rich wood cabinetry, and a breakfast-bar kitchen—ideal for casual meals, morning coffee, or entertaining. Both bedrooms feature spacious walk-in closets, plus you'll appreciate the extra outdoor storage for bikes, golf gear, and more. Enjoy the benefits of a low HOA that covers exterior maintenance, landscaping, pest control, and trash, along with access to the community pool and tennis courts. Cypresswood residents also enjoy resort-style amenities, including an 18-hole Ron Garl-designed golf course, clubhouse, restaurant, and junior Olympic pool. Ideal for first-time buyers, families, professionals, golf enthusiasts, seasonal residents, or investors seeking a turnkey rental in a premier gated community. Prime location: Minutes to I-4 and Hwy 27 for easy commuting. Close to LEGOLAND, Bok Tower Gardens, shopping, dining, medical facilities, and entertainment. Centrally located between Tampa and Orlando—the best of Central Florida at your doorstep. Don't miss this opportunity! Pond-view units in Cypresswood are highly desirable and move quickly. Schedule your private showing today and see why Cypresswood is such a wonderful place to call home.

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Mabel Vassallo (863-604-0499)

Remarks: Step into comfort at 201 maple st! This cozy Winter Haven home offers a welcoming atmosphere with a roomy living areas and spacious yard ready for your personal touch. Enjoy the convenience of nearby shopping, parks, and schools- all within a quiet, established neighborhood. A perfect place to start your next chapter

Listing is courtesy of: ELEVE REAL ESTATE LLC (407-743-7472)

Listing Agent: Nicki Salas Fuentes (863-205-4995)

Remarks: Discover this thoughtfully designed Moonstone home. Included features: an inviting covered entry; a quiet study; a spacious great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a walk-in pantry, a center island and an adjacent dining area; a convenient laundry; a lavish primary suite showcasing a generous walk-in closet and a deluxe bath with double sinks; an airy loft; a mudroom and a covered patio. This home also offers ceramic tile flooring and ceiling fan prewiring in select rooms. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: This move-in-ready home features fresh interior paint, updated countertops, brand-new cabinets, and renovated bathrooms, offering a clean, modern feel throughout. The open-concept floor plan creates a bright and inviting living space, perfect for entertaining or relaxing. Upstairs, a versatile loft provides the ideal spot for a home office, guest area, or flex space to fit your lifestyle. Enjoy low-maintenance living with fantastic community amenities, including a sparkling pool and lake access — perfect for soaking up the Florida sunshine. Ideal for first-time homebuyers, investors or anyone looking for comfort, convenience, and location all in one, this condo offers the perfect blend of style and lifestyle in the heart of Winter Haven. Some photos have been virtually staged to illustrate the property’s potential. Furnishings, décor, and enhancements shown in staged images are for marketing purposes only.

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

Listing Agent: Marquita Smith (863-289-3343)

Remarks: Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years old and have been gently used. ***Please note that the chandeliers and corner hanging lamps do not convey with the sale.**** Residents of this active retirement community enjoy a wide range of amenities, including fishing, a pool and spa, card room, billiards room, social events, fitness center, cable, internet, front lawn maintenance, irrigation, boat dock access (for an additional fee), and boat slips. Don’t miss this opportunity to own your own piece of Florida paradise!

Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)

Listing Agent: Beena Kokeram (813-458-6634)

Remarks: 55+ PLUS COMMUNITY! Corner unit! Features granite countertops, marble kitchen flooring, and wood laminate floors throughout the living room, dining area, and hallway. Interior utility area includes washer and dryer for extra convenience. The primary bedroom opens to a screened-in balcony. This amenity-rich community offers a large heated pool, pickleball and shuffleboard courts, a grilling area, and a clubhouse with a fitness center, perfect for staying active or socializing with neighbors. Additional conveniences include a common laundry room, a secure storage area, reserved covered parking, and elevator access. Ideally located in central Winter Haven, this condo is just minutes from downtown, shopping, dining, hospitals, and medical facilities, with easy access to I-4, placing you perfectly between Orlando and Tampa. Enjoy a vibrant lifestyle in a prime location.

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

Listing Agent: Rosa Suarez (954-682-2633)

Remarks: This meticulously maintained 3-bedroom, 3-bath home showcases eco-smart features and true pride of ownership, all within the sought-after 55+ gated community of Traditions. Thoughtfully designed and beautifully upgraded, this residence offers comfort, efficiency, and a relaxed Florida lifestyle. Upon arrival, you’re greeted by Florida-friendly landscaping accented with stone curb edging and a decorative paved walkway. The welcoming foyer features a transom window and a convenient coat closet. The spacious living and dining areas offer an open-concept layout enhanced with tile flooring—ideal for entertaining. Oversized sliding glass doors open to an extended screened-in lanai, seamlessly expanding the living space outdoors. The well-equipped kitchen features 42" upper cabinetry trimmed with crown molding, a stainless steel appliance package, and a walk-in pantry to meet all your culinary needs. A center island adorned with quartz countertops perfectly complements the glass tile backsplash, adding both function and style. The generously sized primary bedroom suite is a luxurious retreat, offering wall-to-wall carpeting and dual walk-in closets. The primary bath impresses with a handicap-accessible tiled shower featuring decorative listello tile, a comfort-height double-sink vanity, and a linen closet. A junior bedroom suite includes a private en-suite bath with a comfort-height vanity and quartz countertop—ideal for guests or extended stays. Step outside to your private oasis, where the paved screened lanai provides a peaceful setting for outdoor entertaining. This premium lot with no rear neighbors enhances privacy and tranquility. Additional Features & Upgrades Screened-in front entrance with paved walkway, Smart thermostat and smart home technology, Hybrid water heater, Low-E double-pane windows, Ring doorbell and MyQ garage door opener, Laundry room with washer and dryer, In-wall pest control system and termite bait traps, Exterior carriage lighting, Gutters, Two-car garage with epoxy finished floor. The picturesque Community of Traditions offers Planned Community Activities and an array of amenities such as a Lake Front Clubhouse, Dock & Boat Ramp, Heated Swimming Pool and Spa, Ballroom, Billiards, Meeting Room, Library, Computer Room, Craft Room, Dog Park, Tennis Courts, Basketball Court, Bocce, Shuffleboard, Fitness Center, and Aerobics Studio. Conveniently located near Shopping, Restaurants, Legoland and Major Routes, this home offers the perfect combination of luxury, comfort, and convenience.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Eileen Belanger (863-221-0229)

Remarks: Welcome home to this charming 3-bedroom, 2-bath residence nestled on a spacious lot in the heart of Winter Haven. Offering nearly 1,300 square feet of comfortable living space, this well-maintained home features a functional layout with a kitchen and family room combination, ceiling fans throughout, and plenty of natural light. Step outside to your private backyard oasis complete with an in-ground pool—perfect for relaxing, entertaining, or enjoying Florida’s sunshine year-round. A one-car garage adds convenience, while the absence of HOA fees provides flexibility and freedom. Ideally located near schools, shopping, dining, and major roadways, this home is a wonderful opportunity for homeowners or investors alike. NEW ROOF 2020, NEW AC 2022. Don’t miss your chance to make this inviting Winter Haven property your own!

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

Listing Agent: Melissa Mottern (863-860-1808)

Remarks: Brand new, energy-efficient home available NOW! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. 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: ALMOST BRAND NEW!! Check out this CHARMING 3 bedroom, 2 bath manufactured home perfectly situated within a fully fenced-in yard! Step inside to find an Open Floor Plan featuring a cozy living room that flows seamlessly into the dining area and kitchen, creating a warm and inviting space. Split Bedroom Plan with the primary bedroom located just off the kitchen, boasting its own bathroom and a walk-in closet! The separate laundry area provides added convenience - even the washer and dryer are included! Enjoy the front covered porch with side screens while having your morning coffee or just to relax after a long day! Additionally, includes a shed, which is great for your storage needs. Don’t miss your chance to see this delightful home — call today to schedule your appointment!

Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)

Listing Agent: Chrissi Jasso (863-618-4000)

Remarks: One or more photo(s) has been virtually staged. BRAND NEW A/C installed 4/7/2026 and NEW ROOF to be installed 4/16/2026! The moment you walk up you’ll discover your own private & peaceful setting under the paved Pergola area incorporated with a running fountain pond awaiting more koi fish. You’ll enjoy your shaded space with the feel & sounds of nature surrounding you. Your entire home is equipped with installed roll-up hurricane shutters (some are hardwired for a flip of a switch, and some are manual). If you love to cook, you’ll love this chef’s dream kitchen offering plenty of cooking/prepping countertop space. Kitchen has an island with electric, gas range, wide breakfast bar open to the living areas and a walk-in pantry. This home offers a split plan layout, wide hallways, ceiling fans, recessed lighting, large closets, high 10 ft ceilings throughout. You will find you have multiple uses of living/family/dining /office areas. The options are endless. Main bedroom has 2 walk-in closets and access to the nice screened-in back patio. The main bedroom bathroom offers a double sink make-up vanity, walk-in shower, and a linen closet. The 2nd full bathroom offers a shower/tub combo with access to the back screened-in patio. The half bathroom is located off the entry to bedroom #3. The inside utility room is equipped with shelving, a utility sink, a cabinet unit, and a built-in ironing board. New luxury vinyl plank flooring in the utility room and bedroom #3. If all this wasn’t enough there is more…. You will love enjoying the 11x25 covered & screened-in back patio. Your front entryway is also covered. The 2-car garage has a newer electric garage door opener, shelving on both sides & a cabinet for storage. It also provides a keyless touchpad for access from the outside. NEW A/C April 2026. Ring doorbell. You won’t want to miss the 12x14 workshop/shed equipped with electric, a work bench, storage shelving, and an access ramp. Your home is situated on a beautiful lot with mature landscaping. The lawn and landscaping is beautiful and will snap back as we just had the FL record-breaking cold front when pictures were taken so see past that. It will all green up beautifully in no time. Lawn irrigation is on a well water system equipped with a timer system. NO HOA!!! Home has been overhead plumbed. All of this conveniently located close to the 570 Toll Rd taking you to Orlando/Tampa. Be sure to check back for the virtual tour link coming soon and will be attached to the listing. Welcome Home!

Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)

Listing Agent: Jennifer Smith (863-559-1229)

Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom manufactured home with an office in the desirable 55+ community of Brookhaven Village, where you OWN your land! Situated on a large lot with no rear neighbors, this property offers an incredible sense of privacy and tranquility. From the moment you enter, you’ll notice the care and updates that have gone into this home over the years. Features include updated windows, fresh interior paint, and modern flooring throughout. Both the roof and AC were replaced within the last 5 years, ensuring peace of mind for years to come. The water heater was just replaced (02/2026). At the front of the home, the Florida room is fully enclosed and equipped with central air and heat, making it a comfortable year-round living space. The open floorplan flows seamlessly into a spacious living room, dining room with built-ins, and a bright kitchen offering ample cabinet and countertop space. The refrigerator was replaced 2 years ago, and the kitchen and bathroom cabinets have been repainted with updated hardware and modern light fixtures added for a fresh look. Down the hallway, you’ll find a dedicated office, ideal for working from home or enjoying a favorite hobby. The guest bedroom includes a walk-in closet, and the guest bath has been tastefully updated. The oversized primary suite is located at the back of the home and features a large walk-in closet and an ensuite bathroom with dual sinks and a walk-in shower. Step outside to your screened-in lanai, perfect for morning coffee or afternoon relaxation. Beyond that, the backyard oasis features a paved patio and serene views; your own private retreat. Hurricane shutters were just installed, adding extra protection and value. The low $34/month HOA fee includes access to the clubhouse, heated pool, shuffleboard courts, and storage area (upon availability). Brookhaven Village offers a prime Central Florida location close to HWY-27, providing easy access to I-4, Tampa, Orlando, and both Gulf and Atlantic beaches. Be sure to explore the 3-D virtual tour, then come see this wonderful home in person. Whether you’re escaping cold winters or seeking an affordable year-round lifestyle, this home is ready for you to enjoy the Florida sunshine. Schedule your private showing today!

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy and a peaceful feel while enjoying the security and convenience of community living. Inside you will find updated luxury vinyl flooring, windows, stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer and AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Enjoy effortless living in this beautifully updated condo perched on the 8th floor, offering breathtaking views of Spring Lake. This spacious residence features 2 bedrooms and 2 bathrooms, including a master suite with a walk-in closet and private bath. The custom kitchen is a standout with granite countertops, wainscoting ceiling, and a convenient bar, complemented by updated appliances and a new LG washer/dryer tower. Flooring includes ceramic tile, laminate, and cozy carpet in the bedrooms, while new windows with motion solar shades bring in natural light and comfort. Located in a desirable 55+ gated community, residents enjoy resort-style amenities including a heated pool, tennis courts, shuffleboard, and a welcoming social room with kitchen. Additional conveniences include 2 elevators, a covered parking space, and monthly fees that cover water, cable, internet, and community amenities.

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

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