Winter Haven Homes For Sale & Real Estate - 1034 homes

Remarks: Built in 2024, this stunning home showcases a modern open-concept kitchen that flows effortlessly into the dining area, spacious great room, and private outdoor patio—ideal for entertaining and everyday luxury living. Located in the desirable Villamar community, residents enjoy access to two resort-style amenity centers featuring clubhouses, sparkling pools, and playgrounds. Set in the heart of Winter Haven, this home is surrounded by beautiful lakes, waterfront dining, and a vibrant arts scene, with top attractions like LEGOLAND® Florida and Peppa Pig Theme Park just minutes away. Villamar is located in Winter Haven on State Road 653, a north-south connector road between SR-60 to the south and CR-540A to the north, providing easy access to major employment centers. This community is only two miles from Legoland and in close proximity to Posner Park which offers many stores, restaurants and entertainment for your family, as well as the Orlando's theme parks. Designed with innovative, energy-efficient features, this home delivers exceptional comfort, long-term savings, and peace of mind. Best of all, furniture and appliances included—making this a truly move-in-ready opportunity you won’t want to miss.

Listing is courtesy of: PRIVILEGE REAL ESTATE & INVESTMENTS INC (407-791-4909)

Listing Agent: Oscar Isaac (321-697-2109)

Remarks: Located in the heart of downtown Winter Haven, FL, this versatile R-3 zoned property presents an excellent opportunity for homeowners, investors, or those seeking future development potential! This charming residence features 2 bedrooms and 1 full bathroom, offering a functional layout with comfortable living spaces. The home includes a spacious kitchen with ample cabinetry and room for dining, perfect for everyday living or rental use. A dedicated utility room adds convenience and extra storage space. Connected to city water and sewer, this property provides reliable infrastructure and ease of maintenance. The R-3 zoning allows for a variety of potential uses (buyer to verify with city) making this a flexible investment in a growing and desirable downtown location. Enjoy close proximity to local shops, dining, parks, and all that Winter Haven has to offer, including its renowned chain of lakes! Whether you're looking for a primary residence, rental property, or future development opportunity - this property checks all the boxes!

Listing is courtesy of: RE/MAX REALTY PLUS (863-385-0077)

Listing Agent: Emily Jones (863-446-3246)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. THREE BEDROOM--TWO AND A HALF BATH CORNER UNIT--DOWNSTAIRS--COVERED PARKING IN FRONT OF UNIT. Welcome to the "SEVILLE" located in beautiful Orchid Springs. This building has a brand new roof (2025) and all new exterior painting is coming soon. This is a large (1,617 sq ft) triple-split bedroom plan condo. This is a three bedroom, two and one half bath corner-unit residence located on the ground floor. The home offers loads of upgrades--remodeled kitchen and baths, new roof, all new plumbing, newer appliances including washer and dryer. Appliances installed in 2021. All double pane windows with privacy tint and the a/c and heater were installed in 2022. The living area is quite spacious and looks out to the rear yard that is beautifully landscaped like a tropical oasis. The remodeled galley kitchen has a breakfast bar great for morning coffee and a nice pantry. The large primary bedroom has an ensuite bath with bidet, large shower and a walk-in closet. The second bedroom and second bath are secluded by a new barn door that makes it a second primary bedroom. This second remodeled bath has a bidet and a tub and shower. The third bedroom has a half bath and linen closet close to it....giving all parties access to their own bath. There is also an inside laundry area with a full size washer and dryer that is included in the sale. The community clubhouse and pool are close by for your enjoyment. There is also an open porch area at the rear of the condo for relaxing and enjoying our beautiful weather. Monthly maintenance fee includes the use of the clubhouse and pool, exterior building maintenance, lawn care, water, sewer, gas and trash. Come and enjoy this "maintenance free" lifestyle.

Listing is courtesy of: QUINN & COMPANY REALTORS, LLC (863-412-2287)

Listing Agent: Brenda J Quinn (863-412-2287)

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! Open first floor creates a unified living space with a large great room that overlooks the kitchen and dining area. Upstairs loft can be used to best fit your needs and tech area is perfect for a home office. 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! Retreat to your primary suite located 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 contract-accepting backup offers. Pre-Construction. To be built. New construction home with 2005 square feet on one-story including 3 bedrooms, 2 baths, den, 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: Under contract-accepting backup offers. Pre-Construction. To be built. New construction home with 2005 square feet on one-story including 3 bedrooms, 2 baths, den, 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: Fully renovated 3BR/2BA home with an open space perfect for office or extra space located in Winter Haven NO HOA! New Roof, New AC, New Water Heater, New Flooring, New Kitchen Cabinets, updated bathrooms cabinets, and modern finishes throughout. Turn-key and move-in ready with a spacious yard and great location. Huge fenced backyard with banana trees Plus, NO HOA — enjoy more freedom and lower monthly costs Don’t miss it!

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

Listing Agent: Karina Turcios (407-346-7606)

Remarks: Just reduced approx. $30,000 below appraised value to allow for remodeling! This 2 Bedroom, 2 Bath home is located in Brandy Chase Village, a well-maintained 55+ community with clubhouse and heated pool. This home is surrounded on each side by green space views and conveniently located directly across from the community center. Open floor plan. Large, screened porch on back with utility room as well as screened porch at entry. Includes assigned covered parking in front. NEW ROOF 2022 and home RE-PIPED in 2024. Residents can take advantage of the clubhouse for social gatherings and events plus enjoy the heated community pool. Besides the recreational facilities, the HOA includes lawn maintenance, trash, water and sewage. Schedule a tour today to see this charming home and community.

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Donna Sealy (863-206-5328)

Remarks: Under Construction. Brand-new 3-bedroom, 2-story townhome with garage in Winter Haven, FL! This professionally designed home features an open-concept main level with a spacious gathering room, flex space, powder room, and private covered lanai. The modern kitchen offers shaker-style soft-close cabinets, premium laminate countertops, stainless steel Samsung appliances, a breakfast bar, and walk-in pantry. Upstairs includes a private owner’s suite with walk-in closet and dual-vanity en-suite bath, plus two generous secondary bedrooms sharing a dual-vanity hall bath. Enjoy low-maintenance luxury vinyl plank flooring, stain-resistant carpet, energy-efficient LED lighting, built-in pest control, and energy-saving features including R-30 insulation, Low-E windows, and a programmable thermostat—move-in ready with style and efficiency.

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

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

Remarks: Under Construction. Brand-new 3-bedroom, 2.5-bath two-story townhome with garage in Winter Haven, FL. The open-concept main level features a spacious living area, flex space, powder room, and private covered lanai. The professionally designed kitchen includes a breakfast bar, 36-inch soft-close birch cabinets, premium laminate countertops, walk-in pantry, and Samsung stainless steel appliances. Upstairs, the owner’s suite offers a walk-in closet and en-suite bath with dual vanities and a tiled shower, while two additional bedrooms share a dual-vanity hall bath. Features include luxury vinyl plank flooring in main areas and baths, stain-resistant carpet in bedrooms, LED lighting, built-in pest control, and energy-efficient construction with Low-E windows, R-30 insulation, and a programmable thermostat. Move-in ready and easy to maintain.

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

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

Remarks: EXCELLENT INVESTMENT OPPORTUNITY IN THE HEART OF WINTER HAVEN! LOCATED AT 601 AVE U NE, THIS PROPERTY OFFERS INCREDIBLE POTENTIAL FOR RENTAL INCOME OR FUTURE DEVELOPMENT. WITH A SPACIOUS LOT AND SOLID STRUCTURE, IT'S PERFECT FOR INVESTORS LOOKING TO RENOVATE, RENT, OR FLIP. CONVENIENTLY SITUATED NEAR DOWNTOWN WINTER HAVEN, SCHOOLS, SHOPPING, AND MEDICAL FACILITIES, THIS LOCATION IS IDEAL FOR LONG-TERM TENANTS OR RESALE VALUE. BENEATH THE EXISTING CARPETING, YOU WILL FIND WELL-PRESERVED HARDWOOD FLOORING READY TO BE DISCOVERED AND ENJOYED. DO NOT MISS YOUR CHANCE TO OWN A PIECE OF RAPIDLY GROWING WINTER HAVEN-OPPORTUNITIES LIKE THIS DO NOT LAST LONG!

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

Listing Agent: Brian Reeves (877-366-2213)

Remarks: Under Construction. Indigo BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  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 updated 2 bed, 2 1/2 bath townhome in the desirable Park Lake Community. Enjoy a modern kitchen (2023) plus a new A/C, renovated master bathroom with a relaxing soaking tub (2024). Located in a quiet neighborhood just minutes from downtown, shopping, restaurants, hotels and only 10 minutes to Legoland. Right next to the Advent Sports Complex. Great location with recent upgrades, bring your offers.

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

Listing Agent: Janet Lynn (407-314-6198)

Remarks: Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood with a welcoming atmosphere and a beautiful lake view to enjoy. Recent updates include new kitchen and bathroom flooring, new windows, and new interior and exterior doors, along with a roof that is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

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

Listing Agent: Jody Pagan (863-604-2367)

Remarks: Short Sale. This charming home is a diamond in the rough, waiting for the right owner to unlock its full potential. Located in a sought-after neighborhood of picturesque red brick homes, this property offers a unique opportunity for those with vision and ambition. This home is being sold as a short sale, making it an ideal project for those looking to invest in a renovation loan and transform it into one of the best investments on the street. Surrounded by beautiful homes with strong property values, this two-level home boasts 5 bedrooms (with potential for a 6th), three bathrooms, and 2579 square feet of living space. Inside, you'll find real hardwood floors, double-paned windows, a cozy wood-burning fireplace, and a double car garage, all situated on a spacious 0.32-acre lot. With a little TLC and creativity, this property has the potential to become a stunning showcase home that stands out in the neighborhood. Don't miss this opportunity to own a piece of Winter Haven's red brick charm and create the home of your dreams. Schedule a showing today and start envisioning the possibilities that await.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Kelley Blackburn (813-478-0023)

Remarks: Come see this gorgeous 4-Bedroom Home in the beautiful community of Lucerne Park Reserve, Winter Haven, FL – a beautifully designed 4-bedroom, 2.5-bathroom home located in the amazing Lucerne Park Reserve community. Located in a prime corner lot, this home provides you a modern design, spacious living, and an incredible community that is perfect for families who are looking for comfort. Key Features: Spacious & Functional Layout: This is a designed 2,340 sq. ft. home with an open-concept living space, perfect for entertaining. It is located in a big Corner Lot with a Huge Fenced Backyard. It is perfect for you if you need some extra privacy or space for outdoor activities, pets, and even to build a pool! In addition, the property has an Air-Conditioned 2-Car Garage and some Extra Driveway Parking. In the second floor you will find the Loft that would be perfect for entertainment. You cannot miss the incredible Master Suite with a custom walk-in closet, designed for ultimate storage and organization. The property offers a beautifully upgraded open kitchen with a big island, perfect for family gatherings and entertaining guests. One of the most important features is that you will enjoy a Brand-New AC Unit. The property is Located in Winter Haven, Lucerne Park Reserve that is a peaceful, family-friendly community with beautiful surroundings, great amenities, and easy access to major attractions. The community is just Minutes away from LEGOLAND Florida Resort. You will get a close Access to the Winter Haven Chain of Lakes. The community is in an amazing location that is close to Downtown Winter Haven where you can Enjoy boutique shopping, fine dining, and cultural venues like The Ritz Theatre and Theatre Winter Haven. You will get into the major highways in just a few minutes with Easy access to Orlando, Tampa, and other major cities for work or entertainment. Don't miss the opportunity to see this beautiful corner lot property before it is gone! You can be the next owner and live in the after sought community of Lucerne Park Reserve! Come see it today!!

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

Listing Agent: Carlos Carreno Ledezma (407-580-2914)

Remarks: Welcome to Brandy Chase Village!! This well desired 55+ community located in Winter Haven Florida is centrally located between Tampa and Orlando. The beautiful 2 bedroom and 2 bathroom home is well maintained and ready for you! Enjoy your oversized sunroom that adds extra square footage of living space for you to enjoy. Updated appliances and a new AC was installed in 2021 , as well as it was replumbed in 2021. Assigned covered parking space with additional guest parking spot. Are looking for a new primary residence , to downsize or a winter getaway? Either way you will not be disappointed with everything this property offers. Beautiful grounds and low cost HOA fee which includes water/sewer, garbage,lawn care, clubhouse and pool maintenance. Minutes from the Polk Parkway and the neighboring cities of Lakeland , Auburndale and Bartow this is the perfect location for you! Call today for your showing , don't miss out on your opportunity to call Brandy Chase your home!

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Rosalia Abreu (954-854-3694)

Remarks: Experience lakeside living in this custom-built home, perfectly situated on the shores of Lake Grassy. As you approach the property, you are greeted by a sprawling 13’x60’ front porch complete with a charming swing and ample space for entertaining. Imagine hosting gatherings here, with tables lined up as you enjoy views of the beautifully landscaped front yard. Step inside through a wide foyer that seamlessly flows into a spacious family room, where soaring ceilings amplify the sense of openness and elegance. The heart of the home is the newly renovated kitchen, featuring hickory wood cabinets with convenient roll-out drawers, modern appliances, and an eat-in area framed by a picture window offering breathtaking lake views. Adjacent to the kitchen, the formal dining room features sliding glass doors that open to a cozy back porch, creating the perfect indoor-outdoor flow for dining and relaxation. The home boasts 180 feet of lake frontage, complete with a private boat dock and concrete retaining wall, inviting endless water activities and lakeside enjoyment. Eco-friendly and cost-efficient, this home is equipped with fully paid solar panels and a private well, ensuring significant savings no utility bills. The expansive laundry room provides additional storage space, enhancing functionality. The main bedroom is a serene sanctuary with its own private lake view and sliding glass door that opens to a private lanai, offering a tranquil space to unwind. The main bedroom has on-suite bathroom, separate water closet, double sinks, jacuzzi tub, separate shower and double sinks. The second bedroom is thoughtfully designed with a dog door leading to secure dog fencing, making pet care effortless. The second and third bedrooms have walk in closets and share a convenient 2nd bathroom. Car enthusiasts or hobbyists will appreciate the oversized 35’x38’ garage, perfect for a workshop or extra storage, and includes a full bathroom. Additionally, a detached building is primed to become an in-law suite or a private home office, adapting to your changing needs. Don’t miss the opportunity to own this lakefront gem. Call for your private viewing today and start living your dream on Lake Grassy!

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Kelley Blackburn (813-478-0023)

Remarks: Clean, clean, clean. Welcome to 356 Sterling Drive — a meticulously maintained 3-bedroom, 2-bath pool home that truly shows like a model. Pride of ownership is evident from the moment you arrive, where outstanding curb appeal showcases fresh exterior paint, hurricane-rated double-pane windows and sliding doors, lush landscaping, and a welcoming front lawn. This move-in ready residence offers extensive recent updates, including a brand-new roof with Heritage Proline Titan XT shingles (2025), refinished pool, new stainless steel appliances (2023), water heater (2023), new double-hung hurricane rate double pane windows (2024), updated bathroom vanities, new interior and exterior paint (2023), upgraded door hardware and electrical faceplates (2023), and more. Inside, an open and airy layout features tile flooring throughout, elevated ceilings, and an inviting great room designed for both relaxed living and entertaining while capturing tranquil views of the screened pool. The eat-in kitchen provides generous workspace, ample cabinetry, newer stainless appliances, and a charming bay-window dinette ideal for everyday dining. A desirable split bedroom plan ensures privacy. The spacious primary suite offers generous closet space and a well-appointed en-suite bath with dual sinks, updated finishes, and a tiled walk-in shower. Secondary bedrooms are nicely sized and provide convenient access to the full guest bath. Outdoor living is where this home truly shines. The screened pool and fully fenced backyard create the perfect setting for enjoying Florida’s year-round lifestyle, offering privacy, space for pets or play, and fruit trees that add beauty and a touch of nature. A two-car garage provides additional storage and everyday convenience. Located in the established Berryhill community of southeast Winter Haven, the home offers convenient access to shopping, dining, schools, medical facilities, and everyday essentials. Winter Haven’s central location between Tampa and Orlando makes commuting and travel easy while still enjoying the relaxed lifestyle the area is known for — including the Chain of Lakes, boating, recreation, and a vibrant community atmosphere. A beautifully updated home, thoughtfully cared for, and ready for its next chapter.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)