Homes for Sale Near Denison Middle in Winter Haven - 174 homes

Remarks: Under contract-accepting backup offers. Discover Florida living at its finest in this beautifully maintained single-story pool home located in the desirable Hamilton West community of Winter Haven. Situated on an impressive ¼-acre lot with no rear neighbors, this property offers both privacy and space with approximately 2,000 heated square feet designed for comfortable living and effortless entertaining. This 4-bedroom, 2-bathroom home has been meticulously cared for and thoughtfully updated. Major improvements include a new roof installed in 2020 and HVAC replaced in 2017, giving buyers peace of mind. Inside, the home was freshly painted in 2022 and enhanced with numerous tasteful upgrades including taller baseboards, updated lighting, doorknobs, faucets, showerheads, towel bars, and toilet paper holders. Additional updates include a new garbage disposal (2022), new cabinet and mirror in the guest bathroom, a new ceiling fan in one of the bedrooms, and a wine cooler added to the dry bar area—perfect for entertaining guests. Step outside and experience a backyard designed for making memories. The sparkling pool is enclosed with brand-new screening (2023) and complemented by a fully installed outdoor kitchen (2023) that creates the ultimate space for weekend cookouts and gatherings. Paver sidewalks and portions of the backyard were added in 2023, enhancing both style and functionality, while a white privacy fence installed in 2022 neatly conceals the garbage cans and pool equipment. The interior features honeycomb shades and curtains throughout, with room-darkening shades in the bedrooms for added comfort and relaxation. The lush landscaping has been lovingly expanded by the homeowners with additional foliage and fruit-bearing trees including key lime, lime, lemon, and banana, bringing a touch of Florida’s natural beauty right to your backyard. With its spacious lot, private setting, inviting pool area, and extensive updates, this home is ideal for relaxing evenings, lively gatherings, and enjoying the Florida lifestyle year-round. Located near parks and outdoor recreation, it’s a place where family and friends will always want to visit.

Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)

Listing Agent: Greg Staker (407-589-1600)

Remarks: FOR SALE-2 Bedroom/1 Bathroom Single Family Home with a 1l/4 of an acre of land. This is a cute home that has had some remodeling done. It's close to the Polk Parkway to the West and close to Highway 27 to the East not to mention that it's only minutes from Bartow which is the County Seat. Come take a look at this cozy home!

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

Listing Agent: Linda Andre (863-852-5747)

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: *** Motivated seller! Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! *** Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.

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

Listing Agent: Brian Surrency (863-204-4298)

Remarks: Under contract-accepting backup offers. Welcome to 1622 Klatt St SE in Winter Haven, a unique opportunity offering business residential zoning ideal for homeowners, investors, or small business use. This property provides flexibility for residential living, home office, rental income, or professional services in a growing and centrally located area. Situated on high and dry land, this property offers added peace of mind with no flood concerns. The lot and location make it well-suited for long-term ownership, redevelopment, or income-producing potential. Conveniently located near major roadways, shopping, dining, and local amenities, this property benefits from strong accessibility and visibility while still maintaining a residential feel. The surrounding area continues to see growth, making this an attractive option for buyers looking to secure property in a developing corridor. This property is priced appropriately for today’s market, creating an excellent opportunity for buyers seeking value, flexibility, and location in Winter Haven.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Sellers Preferred Lender. Stylish spaces, flexible floor plans, and all the modern amenities—this home is built for your vibe. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, this home is sure to check all your boxes. The front door opens to luxury vinyl plank flooring and soaring ceilings that flows seamlessly to the main living areas. Off the foyer is a secluded in-law suite, providing privacy and comfort for family or visitors. The sliding glass doors off the kitchen offer an easy escape to the Florida sunshine. The second floor features the additional bedrooms, a laundry room equipped with new washer and dryer, and a large bonus room for efficient family living. The owner's suite is a true retreat, featuring a walk-in shower, a spacious walk-in closet and a double vanity. With 5-bedrooms, 3-bathrooms, and a 2-car garage, the Indigo is the perfect home for growing families or those who enjoy entertaining. Contact or make an appointment for more details on interest rates. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

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

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

Remarks: Under contract-accepting backup offers. Welcome home to Ruby Lake, an established gated neighborhood of only 214 executive homes nestled between beautiful Lake Ruby and Lake Bess in Winter Haven. Known for its peaceful setting and pride of ownership, this sought after community captures the charm of lake life. This beautifully renovated pool home has been thoughtfully updated from top to bottom and offers incredible features rarely found in this price point, including a full, private entry in-law suite and fully paid solar panels for remarkable low energy costs. Sitting on a pristine quarter acre lot, several tall palm trees and mature landscaping welcome your arrival. Once inside, you have a clear view of the sparkling pool and lush green yard beyond the double sliding glass doors, connecting indoor-outdoor living. Durable easily maintained laminate flooring flows throughout most of the home, with upgraded LVP in the in-law suite and neutral porcelain tiles at the entry and kitchen. Entirely carpet free for clean, easy living. Privately positioned at the front of the home, the primary suite serves as a quiet retreat tucked away from the main living area. The fully renovated ensuite bathroom is striking, featuring designer finishes throughout – including bohemian-inspired tile flooring, dramatic floor to ceiling shower tile, a custom shower bench and niches, matte black fixtures and a stunning arched window that fills the space with natural light. Dual vanities, a dedicated vanity space and additional overhead storage complete the bathroom. The standout feature of this home is the versatile in-law wing. With its own private entrance and driveway, spacious bedroom, full bath, personal living room with lanai access, and a full kitchen with all appliances included, this private suite offers endless possibilities. It’s ideal for extended guests, multigenerational living, or even a private retreat. The main kitchen is both stylish and functional, featuring quartzite countertops and tiled backsplash, freshly painted wood cabinetry, farm sink, stainless steel appliances and a deep built-in pantry with charming barn door access. A breakfast bar under custom pendant lights provides casual seating, while the sunny breakfast nook with built-in bench seating offers a relaxed spot to start the day. Sliders from the master, living, and family room all open to the screened lanai, showcasing beautiful pool views. The saltwater pool is surrounded by plenty extra deck space for both alfresco dining and pool side sunbathing. Outdoors, the fully fenced yard is over a quarter acre and has room to relax, play or garden. The home backs up to the neighborhood retention space, providing added privacy with no rear neighbors. Nestled in Ruby Lake, a peaceful and well-established neighborhood with no CDD and a low HOA, residents enjoy proximity to the area’s beautiful lakes while remaining centrally located between Tampa and Orlando’s shopping, dining and world-class attractions. Experience the comfort, flexibility and Florida lifestyle this exceptional home has to offer. Welcome home!

Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)

Listing Agent: Beth Stevens, Pa (813-967-0772)

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: Check out this upgraded Columbus on a corner lot! 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, which has upgraded contertops, dining room and family room, with a patio extending the interior space outdoors, patio has also been upgraded with a 12x8 concrete flooring perfect for a lania or sunroom. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite with upgraded master bath and closet. Completing the home is a convenient two-car garage. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

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

Listing Agent: Garrett Collins (623-466-3925)

Remarks: Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!

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

Listing Agent: Chris Sakamoto (904-200-7535)

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)

Remarks: WELCOME HOME TO THIS MOVE IN READY LAKEFRONT CONDO. 2BEDROOM - 2 BATH WITH 1252 SQ FT OF LIVING AREA , PLUS A FLORIDA ROOM OVERLOOKING LAKE BUCKEYE. THIS CONDO UNIT HAS STORAGE THROUGHOUT, GREAT STORAGE CLOSET OFF THE FLORIDA ROOM, ALSO INSIDE UTILITY WITH WASHER/DRYER HOOKUPS AND THE PRIMARY BEDROOM HAS A WALK IN CLOSET. YOU HAVE THE PRIVACY OF THIS UPSTAIRS UNIT WITH A BEAUTIFUL VIEW, NEW CARPET & INTERIOR PAINT,. IT ALSO FEATURES CONVENIENT COVERED PARKING AND COMMUNITY POOL & TENNIS. LOCATED NEAR POLK STATE COLLEGE , YOU CAN ENJOY A WALK AROUND NEARBY LAKE ELBERT OR DRIVE JUST MINUTES TO DOWNTOWN WINTER HAVEN FOR SHOPPING, RESTAURANTS AND COMMUNITY EVENTS. DON'T MISS OUT ON THIS LAKEFRONT VIEW OF LAKE BUCKEYE .

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)

Remarks: Welcome to maintenance-free living nestled in the thriving community of Cypresswood Golf and Country Club that offers an unparalleled lifestyle and peace of mind with a 24-hour guard at the gated entrance, perfect for year-round living or a worry-free seasonal getaway. This second-floor condo boasts a world of comfort and convenience with the A/C having been replaced entirely in 2024, giving you one less worry, tons of storage in generously-sized walk-in closets that both bedrooms offer as well as additional linen storage in the hallway and primary bedroom that will keep your space organized and clutter-free effortlessly. Dive into relaxation and fun at the community pool or host gatherings, socialize with neighbors, or simply unwind in the inviting communal spaces of the clubhouse. The on-site restaurant offers convenient and flavorful dining options, perfect after a tennis or pickleball match on the community's courts or day of golf on Cypresswood's 18-hole championship course. The low monthly HOA fee includes all exterior maintenance, landscaping, pest control, trash collection, and the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual memberships! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today, and make this lovely condominium yours.

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)