Winter Haven Homes For Sale & Real Estate - 971 homes

Remarks: Welcome to your own slice of paradise on the private shores of Lake Lewis located in the highly sought-after gated community of Orchid Springs Estates! This stunning Mediterranean-style estate offers the perfect blend of luxury, comfort, and timeless elegance. Boasting 4 spacious bedrooms and 4 full baths, this custom-designed home features a beautifully appointed kitchen ideal for entertaining, a dedicated pool bath for added convenience, and multiple living spaces filled with natural light. Step outside to your private screened-in pool oasis, where tranquil lake views and tropical landscaping create the ultimate Florida lifestyle experience. Enjoy fishing, kayaking, or simply relaxing by the water in this serene, private lakefront setting. With premium finishes throughout and exceptional attention to detail, this home offers everything you need in one of the area's most distinguished neighborhoods. Don’t miss this rare opportunity—schedule your private tour today!

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton 55+ golf community—where luxury meets an active, resort-style lifestyle. This thoughtfully designed home features top-notch upgrades throughout, including an additional sliding glass door leading to the back patio, flooding the living space with natural light and creating a seamless indoor-outdoor living experience. The spacious kitchen is a standout, boasting abundant cabinet storage with extended cabinetry along the back wall, perfect for entertaining, organization, and everyday convenience. Smart hybrid water heater and water softener system as well The open and inviting floor plan provides generous living and dining areas, while the private primary suite offers comfort and tranquility. Two additional bedrooms are ideal for guests, hobbies, or a home office. Both bathrooms are well-appointed, and the home’s layout is designed for easy living. Located within Lake Ashton, residents enjoy world-class amenities including championship golf courses, clubhouses, fitness centers, pools, tennis and pickleball courts, planned activities, and a vibrant social calendar. Experience the best of Florida living in this exceptional home—schedule your private showing today and discover everything Lake Ashton has to offer.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: Short Sale. Motivated Sellers- well below appraisal price - Price requires bank approval - Located in the growing Villa Mar community, this Cali floor plan offers 1,828 square feet of modern comfort in a location that blends resort-style amenities with everyday convenience. Residents enjoy a sparkling pool with a second on the way, a playground, and a planned dog park, creating an active and welcoming neighborhood lifestyle. Just minutes from Legoland, Highway 27, shopping, schools, medical centers, and dining, this home offers both accessibility and charm. The open kitchen is a chef’s delight with granite countertops, a generous island, upgraded cabinetry, and stainless-steel appliances, all connecting to bright and spacious living and dining areas. The primary suite easily fits a king bed and features a walk-in closet and a large walk-in shower for ultimate comfort. Outside, a covered lanai offers a peaceful water view with no rear neighbors for complete privacy. Schedule your private tour today and discover why Villa Mar is the perfect address for you.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Christian Clay (863-509-7466)

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 Casa Del Sol, a desirable lakefront community on Lake Hartridge with access to the Winter Haven Chain of Lakes. This spacious 2bd/2.5 bath condo offers 1,334 sq. ft. of comfortable living with a smart two-story layout—main living areas downstairs and both bedrooms upstairs. The home incorporates rustic farmhouse design elements throughout, including decorative farmhouse wall paneling that adds warmth, texture, and character to the living spaces. Natural wood furnishings and neutral tones complement the farmhouse aesthetic, blending comfort with timeless style. This bedroom features a relaxed coastal design with soothing blue tones and nautical accents that create a bright, airy retreat. A bold navy accent wall highlights the space, complemented by decorative fishing net wall art and seaside décor. Large windows dressed in sheer navy curtains allow natural light to fill the room, enhancing the breezy coastal vibe. A second bedroom showcases a soft coastal palette with tranquil turquoise walls and light, breezy window treatments. The rustic whitewashed headboard adds a beach-cottage feel while coordinating with the natural textures and pastel bedding. The room’s calming color scheme and light-filled atmosphere create a peaceful, seaside-inspired retreat perfect for guests or family. The bathroom is enhanced with a sliding barn door, a popular farmhouse feature that combines charm with functionality. The door’s rustic wood finish and exposed hardware create a stylish focal point while maximizing space and adding a touch of modern farmhouse appeal. Enjoy low-maintenance living with HOA fees covering city water, sewer/garbage, exterior building maintenance, grounds care, and pool service. Community amenities include a clubhouse, two pools, tennis courts, shuffleboard, and a community dock with direct Lake Hartridge access. A rare bonus in condo living—an attached 2-car garage. Centrally located near major roadways for easy commuting to Lakeland, Auburndale, and the I-4 corridor, yet tucked into a peaceful residential setting close to downtown events, waterfront paths, and local dining. Ideal as a primary residence, seasonal home, or investment property. Opportunities like this don’t last—schedule your private showing today.

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

Listing Agent: Tomi Miller-Troupe (863-287-0231)

Remarks: Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

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

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

Remarks: EASY TO SEE, SCHEDULE YOU'RE VIEWING NOW! NO LOT RENT HERE....YOU OWN IT! OFFERED PARTIALLY FURNISHED, KITCHEN APPLIANCES AND INSIDE LAUNDRY WASHER, DRYER ALSO INCLUDED. THIS HOME FEATURES UPDATES INCLUDING NEW CENTRAL A/C /Heat pump 2026, NEW ALUMINUM ROOF 2024, PVC/CPVC WHOLE HOUSE PLUMBIMG. ALSO FEATURING 12X40 CARPORT AND 13x10 SOUTH FACING SCREEN ENCLOSED PORCH PLUS A 14x10 COVERED PATIO. BROOKHAVEN VILLAGE A STABLE WELL ESTABLISHED AND-MAINTAINED COMFORTABLE AND QUIET, AGE 55+ CENTRAL FLORIDA COMMUNITY. VERY AFFORDABLE HOA FEE JUST $34.00 MONTHLY (PAID ANNUALLY) INCLUDES USE OF COMMUNITY CLUBHOUSE, HEATED POOL and SHUFFLEBOARD. THE COMMNUITY ALSO HAS AN RV, BOAT/TRAILER, FENCED STORAGE PARKING AREA. THIS HOME IS PERFECT FOR SUNNY SEASONAL OR YEAR AROUND LIVING! QUICK RESPONSE TO OFFERS. TAKE A LOOK!

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

Listing Agent: Don Cleveland, Jr (863-206-4953)

Remarks: Beautifully Maintained 2 bedroom, 2 bath home with a large 2 car garage, perfectly situated on a corner lot. Nestled in Lake Dexter Moorings with a Low Monthly HOA fee! Enjoy access to the neighborhood amenities - a sparkling community pool, a private boat ramp, and a dock. Freshly painted interior! Spanning just over 2,000 square feet of living space, this home offers a spacious great room, an expansive Florida room, and a bright and airy kitchen with a cozy dinette. Large sliding doors open up to the Florida room, creating a seamless transition, allowing easy access to additional space for your entertainment needs. The primary bedroom is complete with an en suite bathroom featuring dual sinks and a walk-in shower. Step outside to your custom brick paver patio, perfect for savouring your morning coffee, having a weekend BBQ, or simply relaxing after a long day. Don't miss this WONDERFUL home, call today!

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

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

Remarks: Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.

Listing is courtesy of: HOMETRUST REAL ESTATE & PTY MGT (863-450-0602)

Listing Agent: Kami Rickert (954-629-7828)

Remarks: Welcome home to Peach Crossings, a brand-new community in Winter Haven! This stunning three-bedroom, two-bathroom home is designed for modern living, featuring an open-concept layout and stylish finishes. The kitchen is a chef’s dream, offering plenty of counter space for meal prep and entertaining. It comes fully equipped with Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave—all included at no extra cost! The granite countertops and sleek cabinetry add a touch of elegance and timeless appeal. This home also features high ceilings, enhancing the open and airy feel throughout the living spaces. Step outside to the covered patio, a perfect spot for relaxing, dining, or enjoying the beautiful Florida weather. This home is also packed with energy-efficient upgrades, including double-pane windows, a programmable thermostat, coach lighting, and a Wi-Fi-enabled garage door opener for added convenience. A mudroom located off the garage provides a dedicated space to store shoes, bags, and coats, keeping your home neat and organized. Plus, it’s conveniently placed next to the laundry room for maximum functionality. Nestled in Polk County, Peach Crossings offers a perfect blend of serene lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, while the community itself features a playground and a picnic area for residents to enjoy. This home is move-in ready with all upgrades included! Schedule your tour today

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Welcome to the Summit model in Peach Crossings, a beautiful brand-new home featuring four bedrooms and two bathrooms with an inviting open-concept design. This home boasts high ceilings, enhancing the spacious and airy feel throughout. The master retreat is a true sanctuary, offering a generously sized bedroom that connects to a luxurious en-suite bathroom with a dual sink vanity for added convenience and a step-in shower for a spa-like experience. The kitchen is designed for both function and style, featuring exceptional counter space and brand-new Whirlpool appliances, including a refrigerator, stove, dishwasher, and microwave. A spacious hall closet provides extra storage, keeping everything organized. The family room is the perfect space for cozy movie nights, with ample room for a large sectional and entertainment setup. Whether it’s a movie marathon or a casual night in, this space is designed for relaxation, laughter, and quality time with loved ones. Step outside to the lanai, an ideal spot for enjoying warm Florida evenings with family and friends. The home also features professional front yard landscaping, adding to its curb appeal. Located in the heart of Polk County, Peach Crossings offers the best of lake living with easy access to shopping, dining, and top attractions. Families will love the highly-rated Polk County schools, and the community features a children’s playground and picnic area for added enjoyment. With all upgrades included, this home is move-in ready! Schedule your showing today!

Listing is courtesy of: LGI REALTY- FLORIDA, LLC (904-449-3938)

Listing Agent: Gayle Van Wagenen (904-449-3938)

Remarks: Under contract-accepting backup offers. This 2022-built 'Hayden' model in Squires Grove surpasses new construction, offering five generously sized bedrooms and a flexible open-concept floor plan. The property features a bright, south-facing backyard, ideal for enjoying Florida afternoons, a contemporary kitchen equipped with granite countertops, and the assurance of a low-risk Flood Zone X designation. Avoid the typical waiting period for new construction and transition into this energy-efficient smart home promptly. This residence is perfectly suited for either a primary dwelling or an investment opportunity. We encourage you to schedule an appointment to view the home today.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Delaindse Leon (407-791-7595)

Remarks: Welcome to your new home, located in Dove's Rest, a 55+ community. This home features an open living area with a new refrigerator and stove. The Air Conditioner was installed in 2024 and the roof is 2021. The windows are a double pane window for added insulation value. The washer and dryer are located inside the home for convenience. This home will be sold mostly unfurnished with the bed in the second bedroom, bar stools, kitchen table, and mounted TV remaining. One dog under 20 lb is allowed. The community offers many activities and amenities including a clubhouse, pool, and shuffleboard. Join in with the many activities or just enjoy the peaceful community.

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

Listing Agent: Kathy Devor (573-450-1679)

Remarks: One or more photo(s) has been virtually staged. This Fully Renovated Gem is ready to go! New Roof at Closing! This beautifully renovated 3-bedroom, 2 bathroom home in Winter Haven, Florida, offers modern living in a serene neighborhood near shopping and seasonal markets. The open-concept layout features a spacious living area, a new kitchen with brand-new stainless steel appliances, and stylish finishes throughout. Each bedroom is generously sized, with the master suite boasting a luxurious walk in Closet. The home also includes a cozy backyard, perfect for relaxation and large shed. Located in a quiet neighborhood, this home combines comfort, convenience, and contemporary charm, making it the perfect place to settle down.

Listing is courtesy of: ALIGN RIGHT REALTY LLC (727-264-6800)

Listing Agent: Austin Williams (516-782-1553)

Remarks: Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Jenna Henderson (850-524-3843)

Remarks: Under contract-accepting backup offers. Welcome to this well-located single-family home situated on a quiet cul-de-sac in Winter Haven, offering a comfortable layout and enjoyable outdoor space. This home features 3 bedrooms and 2 bathrooms with a practical floor plan that supports everyday living. 2 car garage and a large driveway. Newer Shingle Roof 2023. Inside, the living area provides a straightforward, open flow into the dining space and kitchen, making it easy to stay connected whether you’re relaxing at home or hosting guests. The bedrooms are nicely sized, and the two full bathrooms add convenience and functionality. Out back, you’ll find a fully fenced backyard that offers privacy and room to enjoy the outdoors. The covered lanai is a great spot for casual outdoor seating, weekend barbecues, or simply spending time outside regardless of the weather. 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: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!

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

Listing Agent: Casandra Vann (863-546-5446)

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: 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: Under Construction. 2-story new construction townhome with 1,604 square feet, 3 bedrooms, and a covered lanai, located in the brand-new Harbor of Lake Henry community. Downstairs, enjoy an open layout(optional first floor layout with den)and a gourmet kitchen with, shaker-style wood cabinets, Samsung stainless steel appliances, including a pantry. The spacious gathering room opens to your covered lanai. The entire lower level and upstairs baths are finished with luxury vinyl plank flooring, with stain-resistant carpet in the bedrooms. Upstairs, you'll find three spacious bedrooms including your owner's suite complete with a walk-in wardrobe, linen closet, and a private en-suite bath with dual vanities and a tiled shower. Additional features for your convenience include a half bath downstairs, upstairs hall bath for the secondary bedrooms, energy-efficient insulation and windows, and a full builder warranty.

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

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