Homes for Sale Near Denison Middle in Winter Haven - 266 homes

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

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

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Welcome to this charming 2 bedroom, 2 bathroom home in Orchid Springs, a non–age-restricted community where all ages are welcome, located in SE Winter Haven. Thoughtfully updated, this home features new wood plank tile flooring. The open floor plan is highlighted by a spacious and light-filled great room with vaulted ceilings creating a warm and inviting space ideal for everyday living. Just off the great room is a beautiful atrium to fill with your favorite plants or enjoy the evenings outside in your private sanctuary. The primary suite includes built-in closets, sliding glass door open to the back courtyard and an en-suite bathroom with updated wood plank tile flooring, updated vanity and mirror the secondary bedroom is generously sized and located next to the guest bathroom, which features updated vanity and tile flooring. Additional highlights include a one-car garage with laundry area Outdoors, enjoy a paver patio courtyard ideal for BBQs and entertaining. There are plenty of private outdoor spaces for relaxing there is are front and rear screened porches as well as the outdoor courtyard. Orchid Springs is a well-established community offering a swimming pool and clubhouse, with lawn maintenance and amenities included for a low monthly fee. Conveniently located within minutes of shopping, dining, medical facilities, and LEGOLAND® Florida, and centrally positioned between Tampa and Orlando for easy access to theme parks and international airports. Call today to schedule your private showing.

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

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

Remarks: PRICE IMPROVEMENT OF $5K MOTIVATED SELLER BEAUTIFUL GATED GOLF COURSE COMMUNITY An exceptional opportunity to own a beautiful 3brm/2.5 bath home nestled on the 4th hole of the highly sought-after Lake Bess Country Club and Golf Course in Winter Haven. As you step inside, you are welcomed by a charming foyer featuring 10-ft ceilings that create an open and airy ambiance throughout the home. The living room, enhanced by a cozy gas fireplace, provides a perfect setting for those cool winter evenings in Florida. This space effortlessly connects to a spacious breakfast nook, both of which open onto a large lanai that offers tranquil views of the golf course, framed by majestic oak trees draped in moss-ideal for an evening glass of wine. Through French doors off the living room, you will find a stunning study\office equipped with built -in wood shelving with additional storage, perfect for work or leisure. The layout thoughtfully includes two generous sized bedrooms and a full bath on this side of the home. At the heart of the house, the well-appointed kitchen is a dream for any cook. It boasts ample space, views of the golf course, and a breakfast nook for casual dining. A bar area allows friends and family to gather and socialize while meals are being prepared. For more formal occasions, the designated dining room offers an elegant setting. The primary suite is an impressive retreat, featuring a tray ceiling, his and hers walk-in closets, and a spacious bathroom equipped with a large shower and vanity. A private water closet and a hidden washer and dryer behind closet doors add to the convenience of this remarkable space. The home also includes an oversized 2-car garage, perfect for tools and a work table. As part of this vibrant community, you'll enjoy access to the clubhouse, community pool and golf course. This hidden gem offers easy access to Legoland, Highway 27, and I-4, making it a prime location for both relaxation and adventure. The purchase price also includes 1 of 49 shares to the golf club which includes 2 free memberships and unlimited Golfing, enhancing the value of this exceptional property. I invite you to discover this property and envision the lifestyle that awaits you at Lake Bess Country Club. Please let me know if you would like to schedule a viewing or if you have any questions.

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

Listing Agent: Christina Ashley (941-780-0291)

Remarks: Brand new, energy-efficient home available by Oct 2025! Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious 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: Like new 5-bedroom, 3.5-bath home with a functional open layout and abundant natural light. The kitchen overlooks the main living area, making it perfect for entertaining. Upstairs, a versatile loft adds valuable extra living space. With generously sized secondary bedrooms, modern finishes, and a 2-car garage, this home is ready for its next owner. Easy to show!

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: William Figueroa (305-662-1502)

Remarks: Under Construction. Brand new, energy-efficient home available by May 2026! Prepare dinner from this home's open kitchen which overlooks a spacious great room. 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: One or more photo(s) has been virtually staged. Welcome to the Mulberry floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2.5-bath home offers 1,938 square feet of living space and provides excellent curb appeal in its elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Short Sale. Discover this beautifully designed 2023-built 5-bedroom, 3-bathroom home located in the highly sought-after Villamar community in Winter Haven, Florida. This spacious two-story home offers the perfect blend of modern style, functional living space, and scenic water views. The welcoming foyer opens into a bright and airy open-concept floor plan ideal for both entertaining and everyday living. The chef-inspired kitchen features plentiful gray cabinetry, a large center island, stainless steel appliances, and an oversized pantry, all overlooking the spacious living room for seamless gathering and conversation. A downstairs bedroom and full bathroom provide the perfect setup for guests, multi-generational living, or a home office. Upstairs, you’ll find a versatile loft space that can be used as a second living area, playroom, media room, or workspace. The spacious primary suite offers a large walk-in closet and private en-suite bathroom complete with double vanities and a walk-in shower. Three additional upstairs bedrooms, another full bathroom, and a convenient upstairs laundry room provide plenty of room for everyone. Step outside and enjoy peaceful water views right from your backyard. Located in the growing Villamar community, residents enjoy amenities including a community pool, clubhouse, playground, and low HOA fees. Conveniently situated near US-27 and I-4, this home provides easy access to shopping, dining, medical facilities, and entertainment. Nearby attractions include the LEGOLAND Florida Resort, the Winter Haven Chain of Lakes, and the Downtown Winter Haven Historic District. This is a fantastic opportunity to own a newer construction home with water views in one of Winter Haven’s fastest-growing communities. Short sale opportunity — don’t miss your chance to make this home yours!

Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)

Listing Agent: Emily Lietz (863-266-9961)

Remarks: Under Construction. Turquesa BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. The Turquesa is the ultimate family haven, a two-story home featuring 4 bedrooms, 2.5 bathrooms and a private 2-car garage. This home offers an open concept living space designed for both relaxation and entertainment. The half bathroom off the foyer ensures every guest feels at home while the extended foyer opens to the main living and dining area. Featuring luxury vinyl plank flooring and convenient indoor-outdoor living with a lanai through sliding glass doors, it’s a haven of comfort and style perfect for gatherings. The kitchen includes stunning quartz countertops and sleek stainless-steel appliances. Enjoy the spacious upstairs recreation room and the convenience of a laundry room just steps away from the bedrooms. Did we mention the brand-new washer and dryer? The owner's suite is a secluded retreat with oversized his-and-her walk-in closets, dual vanity and a walk-in shower. Completing this expansive home is the smart thermostat with voice control and professionally designed landscaping, this is truly the epitome of family-friendly luxury! 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: Under Construction. Valencia BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Prepare to be impressed by the Valencia, a two-story home featuring 5 bedrooms, 3 bathrooms, and a 2-car garage. This floorplan is designed for modern living and effortless entertainment. Step through the elegant foyer into a vibrant main living area, complete with a private guest suite for ultimate comfort. The kitchen shines with sleek quartz countertops, stainless steel appliances, and luxurious vinyl plank flooring overlooking the dining area which flows beautifully to the covered lanai through sliding glass doors. Upstairs, you’ll find the secluded owner’s suite complete with a walk-in shower, dual vanity and spacious walk-in closet. Conveniently located by the additional bedrooms is the cleverly designed oversized laundry room. Another modern feature of the Valencia is the smart thermostat with voice control, making energy efficient living a breeze. Outside, enjoy the chic elevation and professionally curated landscaping that adds the perfect finishing touch to this exceptional home. 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: Under Construction. Azure BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Welcome to The Azure, where modern design meets practical living in a home that has it all. With 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home is crafted for comfort and style. The extraordinary elevation and professionally designed landscaping create a captivating first impression. Step through the front door to discover luxurious vinyl plank flooring that extends throughout the open-concept layout. The kitchen shines with quartz countertops and all-new stainless-steel appliances, overlooking the dining area and patio. A convenient half bath is located downstairs for guests, while the spacious laundry room upstairs comes complete with a brand-new washer and dryer. Upstairs, you’ll find all four bedrooms, including the expansive owner's suite with a walk-in shower, double vanities, and a spacious walk-in closet. A flexible recreation space upstairs provides an ideal spot for family gatherings. With a smart thermostat ensuring energy efficiency and comfort, the Azure seamlessly blends functionality and modern luxury. 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: Like-New Casa Fresca Home with a VA Assumable Rate @ 4.99%! This Jazmin Floorplan in Harmony on Lake Eloise is a must-see! Built in 2025, this stunning 5-bedroom home—with a dedicated separate playroom/office/den—offers 2,457 sq. ft. of thoughtfully designed living space. Set in the highly desirable Harmony on Lake Eloise community, this property stands out as the only Jazmin model currently available. Step inside to find a bright, modern layout ideal for today’s lifestyle. The open-concept living and dining areas flow seamlessly into the stylish kitchen—perfect for family gatherings or entertaining. The 3-car garage features a polyeurethaned floor, adding a durable, finished touch. Outside, enjoy a fully fenced yard that’s perfect for children, pets, and outdoor fun. Harmony is a vibrant community featuring a resort-style pool and walking paths, all just minutes from LEGOLAND, shopping, and dining. Whether you’re looking for space, style, or location, this like-new Casa Fresca home has it all—perfect for a large or growing family.

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

Listing Agent: Katherine Montana - De Jesus (863-508-3000)

Remarks: Welcome to 652 Grove St. TWO living spaces for ONE price. This exceptional property in the heart of Winter Haven offers a spacious main home plus a fully independent Mother-in-Law Suite all under the same roof. The primary residence features 3 bedrooms, 2 bathrooms, a dedicated office/flex space, an open-concept layout filled with natural light, and a 2-car garage designed for comfortable everyday living. What truly makes this property stand out is the private annex/guest house, complete with its own separate entrance, 1 bedroom, 1 bathroom, semi-equipped kitchen, and private laundry area, creating the perfect setup for extended family, guests, multi-generational living, or a private retreat space. This rare “home within a home” offers flexibility, privacy, and functionality that is hard to find at this price point. Conveniently located near US-27, shopping, dining, and everyday essentials, this unique property is a must-see to truly appreciate its layout and possibilities. Schedule your private showing today.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Lizandra Troisi Passos (321-337-9448)

Remarks: 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: 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: 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: 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: 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 home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!

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

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

Remarks: Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist. The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends luxury with everyday livability. Designed for both entertaining and comfortable living, the open-concept layout showcases luxury vinyl plank flooring throughout, expansive living areas, and a beautifully upgraded chef’s kitchen that serves as the heart of the home. With 4 bedrooms and 4 full bathrooms, the residence provides generous space for family and guests alike. Outdoors, a private pool invites relaxation while remaining surrounded by peaceful, natural views. Adding exceptional value and versatility, the property includes a 1,300 sq ft detached guest house featuring 2 bedrooms and 2 bathrooms, along with an upgraded kitchen and bath—ideal for extended family, long-term guests, or a private work-from-home or creative space. The land itself is what truly sets this property apart. The nearly 11-acre setting offers a thoughtful balance of open usable acreage, mature landscaping, and a scenic private pond, creating a sense of separation and tranquility that enhances both privacy and lifestyle. Multiple outbuildings, including a barn/garage and lean-to structure, provide ample room for storage, hobbies, equipment, or future expansion. In a market where acreage is disappearing and privacy is priceless, properties offering this scale of land, level of renovation, and proximity to town are exceptionally rare. This is not just a home—it’s a private retreat, a long-term asset, and an opportunity to own something truly irreplaceable.

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Brock Jennings (863-990-5846)