Homes For Sale in Winter Haven 33884 - 443 homes

Remarks: Crescent Pointe is a brand new community located in Winter Haven, FL, conveniently situated off State Rd 653 and boasting easy access to a range of nearby attractions. For residents who enjoy outdoor activities, the Winter Haven Chain of Lakes is nearby. It offers opportunities for boating, fishing, and other recreational activities. The community is also close to the bustling downtown area, where residents can explore local shops, dining venues, and family events. With NO CDD and low HOA, Crescent Pointe is an ideal place to call home in Winter Haven.

Listing is courtesy of: VANTAGE PROPERTY MANAGEMENT LLC (863-687-2700)

Listing Agent: Ed Laderer (863-640-3461)

Remarks: Under Construction. Welcome to the Lakeside, one of our one-story floorplans featured in our Harmony at Lake Eloise community in Winter Haven, Florida. Take your pick between two artfully designed exteriors. Inside this beautiful 5 bedroom, 3 bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. The kitchen features modern cabinets, quartz countertops, and sleek stainless-steel appliances, which are sure to both turn heads and make meal prep easy. You'll never be too far from the action with the living and dining area right there. Find luxury vinyl plank flooring throughout a majority of the home including the family room, primary bedroom, kitchen, bathrooms, laundry and foyer. Bedrooms 2,3,4 and 5 will have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Privacy is guaranteed with a separate door for the toilet and shower. Contact us today and find your home at Harmony at Lake Eloise. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy atmosphere created by large windows that allow natural light to flood the home. The home features stunning luxury vinyl plank flooring and a beautiful brick fireplace, adding warmth and character to the space. The kitchen is of good size and boasting sleek countertops, new modern appliances, and ample cabinet space. Enjoy casual meals in the eat-in kitchen or step outside to the screened-in porch, an ideal spot for dining al fresco or simply relaxing while overlooking the expansive backyard and pool. Come add your personal touches and make this house your beautiful home!

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

Listing Agent: Michelle Armbruster (863-521-6879)

Remarks: Light and bright 2/2/1 in The Verandah's at Lake Reeves. The Verandahs offers a community pool and fishing dock on Lake Reeves. The low HOA fee includes ground maintenance, basic cable and internet, exterior painting and more. Easy access to shopping, Legoland, chain of lakes. Light and bright, move in ready. Dual master bedroom set up. Den/office off of main living area. Vaulted ceilings, large kitchen, open living plan.

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

Listing Agent: Cliff Glansen

Remarks: This 3-bedroom, 2-bathroom home located in the Florida Highland Co neighborhood. This residence offers a classic and straightforward layout that provides a comfortable living environment for a variety of lifestyles. The heart of the home features a kitchen equipped with a mix of black and white appliances, complemented by durable laminate countertops that offer plenty of workspace for daily meal preparation. The interior transitions smoothly between living areas, maintaining a functional sense of space throughout. Situated in a convenient location, this property offers easy access to local amenities and major regional hubs, ensuring a simplified commute for those working in the surrounding areas. Schedule your private showing today!

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

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

Remarks: Welcome to 103 Morning Glory Circle in the highly desirable Morningside at Winterset community in Winter Haven. As you step inside, you’ll be greeted by soaring vaulted ceilings, abundant natural light, neutral paint tones and immense charm. The spacious living room is the heart of the home, featuring a cozy fireplace and custom built-in shelving, creating the perfect space to relax or entertain. The home’s layout flows seamlessly, offering both functionality and style, while the tile roof adds durability and long-term value. New HVAC was installed in 2025 and water heater in 2020 along with all new appliances within the last few years. Step outside to your large screened-in patio, ideal for enjoying Florida’s outdoor lifestyle year-round, whether you’re hosting guests or unwinding in your private retreat. Located in a gated community with low HOA and no CDD, homeowners of Morningside at Winterset enjoy access to resort-style amenities including a community pool, clubhouse, tennis courts, private-community boat ramp, and direct lake access to Lake Winterset, perfect for boating, fishing, and soaking up the Florida sunshine. Conveniently situated near LEGOLAND Florida Resort, the Chain of Lakes, shopping, dining, medical facilities, and major highway access, this home offers the perfect blend of peaceful living and everyday convenience. If you’ve been searching for a home that combines character, community, and location, this one checks all the boxes. Schedule your showing today!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Eric Gross (513-907-4271)

Remarks: Welcome to this charming and updated, move-in ready 2-bedroom, 1.5-bath condo nestled right on Cypress Gardens Blvd in Winter Haven — just minutes from world-class shopping, dining, and the famous LEGOLAND Florida Resort! This well-maintained two-story unit has been tastefully updated throughout. Rich dark luxury vinyl plank flooring flows through the spacious living areas, giving the home a modern, cohesive feel. The kitchen is fully equipped with rich wood cabinetry, stainless steel appliances including a dishwasher, range, and refrigerator, and tile flooring — with a sliding glass door that brings in great natural light. A convenient half bath on the main level is fully updated with a new vanity and brushed nickel fixtures. Upstairs you'll find two generously sized bedrooms. The dedicated laundry closet plumbed and ready for your washer and dryer is on the first floor. The classic brick exterior and covered front porch add great curb appeal and a welcoming first impression. Whether you're a first-time buyer, downsizer, or investor looking for a rental in a high-demand location, this one checks all the boxes. Schedule your showing today — this one won't last!

Listing is courtesy of: HAVEN REALTY & INVESTMENTS (863-333-5053)

Listing Agent: Vincent Reina (863-398-6243)

Remarks: New construction home with 1857 square feet on one-story including 4 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty ***Please note - Virtual Tour/Photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

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

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

Remarks: Experience resort-style living in the prestigious gated community of Winterset, just minutes from Legoland. This captivating 3-bedroom, 2-bath villa, featuring Mediterranean-inspired architecture, offers the perfect blend of elegance, comfort, and tranquility. Upon arrival, you’re welcomed by a charming covered screened porch accented with a leaded glass entry door, setting the tone for the inviting interior. The thoughtfully designed split-bedroom floor plan includes a spacious great room highlighted by a wood-burning fireplace, a decorative built-in media center, and glass sliders that open to the Florida room—seamlessly blending indoor and outdoor living. Easy-to-maintain solid surface flooring flows throughout the home. The well-appointed kitchen showcases white cabinetry with crown molding, an upgraded stainless steel appliance package including a gas range and beverage cooler. Granite countertops that adorn the expansive breakfast bar and a double-bowl sink with a gooseneck faucet adds both style and functionality. The open-concept layout is ideal for entertaining, with the formal dining room flowing effortlessly into the living area. The primary bedroom suite serves as a luxurious retreat, featuring laminate flooring, a spacious walk-in closet, and a glass slider providing private access to the Florida room. The primary bathroom offers a granite-topped vanity, upgraded brushed nickel fixtures, a comfort-height toilet, and a tub/shower combination with a decorative tile surround. Both guest bedrooms are generously sized and include walk-in closets, providing ample storage. Outdoor living is elevated with an extended Florida room offering peaceful pond views—an ideal space to relax and unwind. Additional Features: Laundry room with washer and dryer, New ceiling fans throughout with remote controls, new water heater, Updated AC system (2021), Epoxy-finished flooring in the Florida room and garage, Exterior carriage lighting, Gutters, Tile roof, One-car garage with garage door opener. The Winterset community offers an exceptional array of amenities, including a lakefront clubhouse, tennis courts, shuffleboard, a heated pool, hot tub, and access to Lake Winterset, part of the renowned Winter Haven Chain of Lakes. HOA fees include exterior maintenance, grounds maintenance, security, and access to community amenities, ensuring truly carefree living. Conveniently located near shopping, dining, medical facilities, and entertainment, this villa provides a lifestyle defined by 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 to this charming and versatile 2-bedroom, 2-bath home offering 1,706 square feet of living space in Winter Haven. This property features a spacious combined living and dining area, ideal for both everyday living and entertaining. The home also offers a flexible bonus room that can easily be converted into a third bedroom, home office, hobby space, or guest area, along with a bright sunroom at the back—ideal for relaxing and enjoying backyard views year-round. Step outside to a screened-in back porch, ideal for unwinding or outdoor dining, and take advantage of the backyard shed for additional storage. With its adaptable spaces and inviting indoor-outdoor features, this home is a must-see—schedule your private showing today and discover all it has to offer! The home is being Sold in As Is condition without any Warranty nor Guarantee by seller. The buyer is responsible for verifying ALL property information, room sizes, utilities and condition. All buyers must view the home before submitting an offer. HUD CASE: 098-116683 FINANCE ESCROW MAY APPLY FINANCE CODE: IE

Listing is courtesy of: REALTYCITY INC (863-438-6605)

Listing Agent: Jesse Carriedo (863-438-6605)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Short Sale. Short Sale opportunity on a 2023-built 3BR/2BA home offering modern design, open living space, indoor laundry, and a 2-car garage. A rare chance to own newer construction at an affordable price point. Ideal for first-time buyers or investors seeking strong long-term potential. Conveniently located near shopping, dining, and major roadways. Lender approval required.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Wanda Turner (407-756-2194)

Remarks: One or more photo(s) has been virtually staged. Under Construction. This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. Villa Mar is a masterplan community of new single-family homes. Near Historic downtown Winter Haven. There are lots of shops, restaurants, bike paths, and easy access to nearby highways. Close to Legoland and Bok Tower Gardens. The much anticipated “Villar Mar” community is what you have been looking for. A safe small town feel with convenience.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

Remarks: Short Sale. Welcome home to this inviting 5-bedroom, 3-bath family home offering 2,601 sq. ft. of comfortable living on an oversized lot. This move-in ready home is priced to sell fast, and the seller is motivated; don’t wait on this one! Step inside and enjoy the spacious, open-concept layout designed with families in mind. The main floor features a bedroom and office/bonus room, perfect for guests, remote work, or playtime. The family-style kitchen is both beautiful and functional, showcasing granite countertops, upgraded cabinetry, and stainless steel appliances; the perfect space for cooking and connecting. Upstairs, the primary suite offers a comfortable retreat with dual vanities and two walk-in closets, while the loft and three additional bedrooms provide plenty of room for everyone to spread out and enjoy. This home has it all, space, comfort, and convenience, in one of the area’s most desirable communities. Don’t miss your chance to make it yours! The fenced backyard offers privacy for entertaining and is spacious enough for a future pool. A 10-year builder warranty provides added peace of mind. The community residents enjoy a lakeside pool and playground, all conveniently located near US-27 and Thompson Nursery Road. Priced to sell, don’t miss this opportunity!

Listing is courtesy of: ASCENSION REALTY INTERNATIONAL (863-513-0208)

Listing Agent: Sharonda Lawrence (863-513-0208)

Remarks: One or more photo(s) has been virtually staged. This beautifully maintained 2-bedroom, 2-bath home with a 2-car garage offers the perfect blend of comfort, smart updates, and lifestyle perks. There’s something about 4454 Glenns Landing that feels like home before you even step inside. Maybe it’s the quiet charm of the neighborhood — families out walking at sunset, riding bikes, neighbors waving as they pass. Maybe it’s knowing you’re not just buying a house…you’re stepping into a true community. Inside, enjoy the natural light through new windows installed in 2021 and the roof was also replaced in 2020, giving you peace of mind and eliminating two major expenses right from the start. The kitchen has a quaint eat-in area as well as great counter space for food prep and stainless steel appliances. The seamless flow between the living room and dining area creates a spacious feel while keeping everything connected — perfect for entertaining guests, hosting family dinners, or simply enjoying a cozy night at home. The primary suite is a relaxing retreat, featuring a spacious walk-in closet and a private bath with solid surface countertops that add both durability and elegance. The secondary bathroom also showcases matching solid surface countertops, creating a cohesive and polished feel throughout. One of the home’s best surprises, the fully enclosed porch with its own air vent, seamlessly adding extra square footage of living space. Whether you envision a sunroom, home office, reading nook, or second living area, this flexible space gives you room to live the way you want. Step outside your front door and enjoy a neighborhood designed for connection. Residents enjoy access to: a clubhouse with a sparkling pool, a fishing pier and dock, boat slips available on a first-come, first-serve basis, a vibrant social club that plans activities year-round.

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

Listing Agent: Tisha Talbot (863-236-7610)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated home tucked away on a quiet cul-de-sac in the well-established Cedar Cove community, just moments from the scenic shores of Lake Eloise. Set on over a quarter-acre lot, this property offers more than 2,000 sq ft of thoughtfully designed living space, featuring 3 bedrooms, 3 full bathrooms, and an enclosed bonus room that can easily function as a 4th bedroom. Inside, bright formal living and dining areas flow effortlessly into a spacious open-concept kitchen, recently remodeled with granite countertops, modern shaker-style cabinetry, and stainless steel appliances. Dual breakfast bars overlook the inviting family room and dining space, creating the perfect setup for entertaining or everyday living. The family room impresses with soaring ceilings and a striking stone wood-burning fireplace, while luxury vinyl plank flooring and upgraded bathroom vanities elevate the home’s style throughout. A convenient third full bath located near the laundry area is ideal for guests or for future pool-day use, just imagine the possibilities. Step out onto the screened porch and enjoy a generously sized backyard—perfect for gatherings or peaceful relaxation. Additional highlights include an oversized garage with ample storage and workspace, brand-new windows for enhanced energy efficiency and natural light, plus a newer roof and A/C system for added peace of mind. Ideally located near local amenities, downtown Winter Haven, and Legoland, with world-famous theme parks just 40 miles away, this home truly has it all. Don’t miss this rare opportunity to own a standout home in one of Winter Haven’s most desirable neighborhoods!

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

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

Remarks: One or more photo(s) has been virtually staged. Waterfront Serenity Meets Effortless Living in the Heart of Winter Haven. Step into a lifestyle where your biggest daily decision is whether to enjoy coffee overlooking the lagoon or take a refreshing dip in the heated community pool. Nestled on the second floor of the meticulously maintained 55+ Granada Building, Unit 202 is more than just a home; it’s your private sanctuary in the sought-after Orchid Springs community. A Layout Designed for Connection and calm. Experience an open-concept living and dining area bathed in Florida’s natural light. The expansive Florida Roomacts as your front-row seat to nature, offering tranquil water views and lush landscapes that make every sunset feel like a private event. The Primary Retreat: A generously sized suite featuring a massive walk-in closet for ultimate organization. Modern Flexibility: Enjoy the convenience of an elevator and on-site laundry, with the rare added potential to install your own in-unit washer/dryer hookup. Seamless Comfort: A brand-new AC system ensures year-round peace of mind. The Gold Standard of HOA Value. Rarely does an HOA work this hard for you. This "all-inclusive" lifestyle eliminates the stress of multiple bills, saving you hundreds monthly. High-Tech Package: Includes Premium Cable and High-Speed Internet (a $250/month value). Total Utility Coverage: Gas, water, sewer, and trash removal are all covered. Maintenance-Free: Pest control, exterior upkeep, and grounds care are included, so you can spend your weekends at the private park or the clubhouse instead of mowing the lawn. The Best of Winter Haven at Your Doorstep. Beyond the gates of Orchid Springs, you are minutes from the vibrant energy of downtown Winter Haven. Indulge in local favorites like Nutwood or LoveBird, explore the world-famous Chain of Lakes, or enjoy the convenience of being just a stone's throw from LEGOLAND® Florida. Claim Your Piece of Paradise. With a recently adjusted price of $64,900, this move-in-ready residence offers a rare combination of waterfront beauty and unbeatable financial value. Schedule your private tour today and discover why life is better at Orchid Springs.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Carlos Diez Cordova (813-694-6208)

Remarks: Priced to Sell! Fully furnished! Excellent opportunity in the desirable 55+ community of Garden Grove Oaks where you own your land and enjoy low HOA fees. Located at 6133 Grand Oaks Dr SE in Winter Haven, this home offers a great layout with spacious living and dining areas and plenty of natural light. The kitchen provides ample cabinet and counter space, and the primary bedroom includes a private en-suite bath. A second bedroom and bath provide space for guests or a home office. Enjoy relaxing on the screened porch overlooking the peaceful community setting.This home is being sold AS-IS and offers a fantastic opportunity for buyers looking to update and add their own personal touches. Garden Grove Oaks is a well-maintained community conveniently located near shopping, dining, medical facilities, and Winter Haven’s Chain of Lakes with easy access to major highways to Orlando and Tampa.Great value and priced for a quick sale — don’t miss this opportunity!

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

Listing Agent: Anita Lowe (863-269-6461)

Remarks: THIS HOME QUALIFIES FOR 0% DOWN !! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also perfect for walking or biking through beautifully maintained grounds. This home enjoys serene views of the golf course, pond, and stunning sunsets—plus a front-row seat to Legoland’s nightly fireworks. Inside, you’ll find cathedral ceilings, abundant natural light, a split-bedroom layout, and an eat-in kitchen. The laundry room is conveniently located off the kitchen. The screened lanai, featuring new lighting and a ceiling fan, is the perfect spot to enjoy your morning coffee or relax while taking in the wildlife and golf course views. Recent updates include a newer roof (2024), HVAC system, and upgraded electrical, giving you peace of mind. Cypresswood is one of Winter Haven’s most established and picturesque communities, making this home a rare opportunity.

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

Listing Agent: Malak Hassani Benbachir (863-624-7266)

Remarks: BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Square, centrally located in Winter Haven, FL. Before entering this beautiful residence, you will notice the BRICK PAVERED driveway/walkway leading through the MATURE LANDSCAPE and CUSTOM LIGHTING to the front SCREENED LANAI. Walk right into this very OPEN FLOORPLAN with HIGH CEILINGS and SPLIT BEDROOM CONCEPT. The kitchen is a CHEF'S DREAM, featuring UPGRADED STAINLESS APPLIANCES, IMPRESSIVE WINE FRIG., and BREAKFAST BAR. The CASCADING WATERFALL EDGE QUARTZ COUNTERTOPS add a MODERN, ELEGANT and LUXURIOUS focal point to this AMAZING KITCHEN!!! The adjoining great room is very spacious and overlooks the rear SCREENED LANAI with a view of the pond. The primary en-suite will not disappoint which also features QUARTZ COUNTERTOPS and an UPGRADED WALK-IN SHOWER with GLASS DOOR. CUSTOM PLANTATION SHUTTERS in the kitchen and bedrooms ensure you have the privacy you deserve! Don't forget about the second bathroom that has also been UPGRADED with QUARTZ COUNTERTOPS as well. This residence is truly TURN-KEY and one of the most WELL KEPT, ONE-OWNER homes you'll find anywhere. The reasonable monthly HOA dues include: ROOF REPLACEMENT, EXTERIOR PAINTING, YARD MAINTENANCE, LAWN IRRIGATION, and INTERNET/TV PACKAGE! Enjoy the other amenities including, but not limited to: pool/hot tub, tennis/pickle ball, gym, craft room, billiard room, movie room, and large meeting room with remodeled kitchen area. This wonderful property is in close proximity to medical, restaurants, shopping, worship, and LEGOLAND, FL. Winter Haven is well-known for it's beautifully interconnected lakes and being centrally located between the Tampa International and Orlando International Airports.

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

Listing Agent: Bryan Dicks (863-287-7851)

Remarks: This thoughtfully designed Slate home opens with two bedrooms flanking a full hall bath. Beyond the entry, you’ll find an open layout with a dining nook, a great room with access to an inviting covered patio, and a kitchen with a center island, walk-in pantry and abundant cabinetry. The owner’s suite is nearby, offering a generous walk-in closet and a private bath with optional dual sinks, a shower and a separate soaking tub. A laundry room and a fourth bedroom with its own private bath complete the home. *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)