Homes for Sale Near Denison Middle in Winter Haven - 252 homes

Remarks: Don't miss this rare opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas complete with a kitchen breakfast bar. All NEW luxury vinyl flooring, NEW windows and sliding glass patio door, NEW kitchen countertops, and fresh interior paint offer efficiency, comfort, and modern elegance. Walk-in closets in both bedrooms offer an abundance of space for organizing your belongings, and an en suite bathroom in the main bedroom for privacy and convenience with a serene pond view from the primary bedroom. Enjoy the open-concept living area for entertaining friends and family and a private patio further compliment this delightful property. Immerse yourself in the outdoors on your private gated patio or take a walk, run, or bike ride to enjoy the natural scenery that abounds in this community. Cypresswood Golf and Country Club features a 24-hour manned guard gate, 18-hole championship golf course designed by Ron Garl, junior Olympic-sized community pool, lighted tennis/pickleball/basketball courts, clubhouse, restaurant, pro-shop, event space, and so much more. The low monthly HOA fee includes all exterior and grounds maintenance, pest control, trash collection, and use of the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual membership! 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!

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

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

Remarks: This property is eligible under the 30 Day Freddie Mac First Look Initiative through 05/28/2026. OWNER OCCUPIED BUYERS and NSP offers will only be considered the first 30 days from initial MLS input date. Investors are encouraged to make an offer and will be considered after the First Look Initiative period has expired. Buyer pays Doc Stamps on deed. This 2022 home is barely lived in, Island kitchen opens to the great room plan, hard surface counter tops in the baths, 2 car garage, water filtration system. Home is in great condition. Call today to preview this home.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Barry Macchione (863-604-7455)

Remarks: Virtually Staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept floorplan, perfect for entertaining or just hanging out, is complemented by stylish luxury vinyl plank flooring. The kitchen and throughout the home feature elegant quartz countertops, while the stainless-steel appliances and smart thermostat with voice control add a touch of modern technology. The laundry room features a new washer and dryer and is conveniently located upstairs with all the bedrooms. The owner’s suite is situated at the back of the home with a spa-like owner’s bathroom and spacious walk-in closet. Completing this home is beautifully designed landscaping curated for the Florida lifestyle. 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: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,625 square feet of living space, and provides excellent curb appeal in it's 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: If you want a property perfect for first time homeowners or investors that needs a bit of tender, love, and care this is the home for you! Located in Winter Haven, be near of several Florida’s major attractions and major cities! The home has a wooden fence that surrounds the back of the property, be filled with serenity thanks to having a private porch that can be access through wonderful French doors. Enter the home and be greeted by the open floor plan and the fireplace; with three bedrooms and two bathrooms there is room for everyone. With no HOA come use your imagination and make your future dream home!

Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)

Listing Agent: Blanca Armada (407-908-2846)

Remarks: Discover your dream home without the hassle! This stunning two-year old construction features all the modern upgrades you desire. Why buy new when you can purchase this like-new home with so many stylish finishes and energy efficient appliances. Welcome home to this immaculate 4 bedroom / 2 bathroom / 2 car garage home in Winter Haven! Shows like a model! No CDD! Low HOA fees, and lower taxes. GREAT OPEN FLOORPLAN with lots of living space, this home was BUILT IN 2024 and has plenty of features throughout. The home has upgraded tiled flooring throughout the main living areas and a huge great room, perfect for entertaining! The kitchen features a spacious center island, granite countertops, stainless steel appliances, tiled backsplash, and plenty of cabinetry space. There are 4 spacious bedrooms. The owner's suite boasts an en suite bathroom with dual sinks. The backyard is generously sized and is FULLY FENCED and includes a screened patio and a shed for a perfect outside living experience whether you are relaxing, entertaining or hosting family gatherings. Lots of upgrades! Close to shopping, dining, and Legoland. Perfectly situated between Orlando and Tampa .

Listing is courtesy of: RIGHT TRACK REALTY (953-437-4747)

Listing Agent: Phyllis Haigler (804-641-9763)

Remarks: Welcome to this stunning Dream Finders Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,589 square feet of living space and boasts excellent curb appeal due to its impressive elevation. Inside, you'll find gorgeous Gray 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.

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

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

Remarks: DON'T WAIT OPPORTUNITY IN CEDAR COVE Inside, the home offers a thoughtful split of comfort and function with 3 bedrooms and 2 baths, including a private primary suite featuring dual walk-in closets and a beautifully updated bath with a sleek tiled walk-in shower and designer-inspired finishes. Secondary bedrooms include built-ins, creating versatile space for a home office, hobby room, or guest accommodations. The kitchen is designed for both everyday living and entertaining, offering abundant cabinetry, generous prep space, stylish finishes, and an oversized secondary pantry for exceptional storage. Throughout the home, natural light pours in through skylights and expansive windows, highlighting soaring ceilings, durable hard-surface flooring, and a warm fireplace that anchors the main living space. Step outside and feel the difference. This is where Florida living shines. A spacious fenced backyard shaded by majestic oak trees creates a private retreat, complete with a screened lanai, brick paver patio, storage shed, and double gate access. It's ideal for weekend gatherings, quiet evenings, and effortless indoor-outdoor living. VALUE AND PEACE OF MIND ARE BUILT IN: With an acceptable offer, the seller will provide a NEW ROOF before closing and a NEW WATER HEATER already installed, making this a rare, move-in-ready opportunity with major updates already handled. Located just minutes from Tampa and Orlando, this SE Winter Haven cul-de-sac home offers quick access to major airports, world-famous attractions, top dining, shopping, schools, medical facilities, and LEGOLAND Florida. Whether for commuting or weekend escapes to Gulf or Atlantic beaches, the location delivers unmatched convenience and lifestyle flexibility. Homes with this combination of location, outdoor space, and upgrades are hard to find. Schedule your showing before it's gone.

Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)

Listing Agent: John Evans (813-992-3483)

Remarks: This two-story Georgia will definitely be on your mind… This beauty highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family members and guests alike. 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: Welcome to the Spring model in Peach Crossings, a spacious five-bedroom, three-bathroom, two-story home perfectly positioned on a premium corner lot with no rear neighbors, offering added privacy and an open, peaceful setting. From the moment you walk through the door, you’re greeted by a long, inviting foyer that sets the tone for this warm and welcoming home. The first floor features a bright, open-concept family room that’s perfect for entertaining or everyday living. The modern kitchen is designed with both style and function in mind, showcasing a large island with breakfast bar seating, plenty of cabinet space, and brand-new Whirlpool appliances. A downstairs guest bedroom and full bathroom provide the perfect setup for visitors, multigenerational living, or a private home office. Upstairs, the spacious owner’s suite offers plenty of room for a king-sized bed, additional furniture, and even a cozy sitting area or reading nook. The en-suite bathroom includes dual vanities, a linen closet, and an oversized walk-in closet with ample storage. The additional bedrooms are all generously sized, giving everyone their own comfortable space while also offering flexibility for a playroom, gym, office, or hobby room. With three full bathrooms throughout the home, busy mornings are made easy. You’ll also love the oversized upstairs laundry room complete with extra storage and a dedicated closet for added convenience. Step outside and enjoy the covered back patio and charming covered front porch ideal for relaxing with your morning coffee or entertaining guests year-round. Located in the highly desirable Peach Crossings community, this move-in-ready home offers easy access to top-rated Polk County schools, shopping, dining, and local attractions. Best of all, all upgrades are already included, making this home truly turnkey. Schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Kennia Lozada Rivera (407-259-9096)

Remarks: Virtually Staged. Fully occupied 5-unit multifamily investment property located minutes from Downtown Winter Haven in a high-demand rental market. Zoned multifamily and currently producing immediate cash flow with all units leased. Strong location near major thoroughfares, retail, and ongoing residential development, including a planned townhome project that is expected to support future rental demand. Opportunity exists for additional income growth through rent optimization. Situated in one of Central Florida's fastest-growing submarkets, this stabilized asset offers current income, long-term appreciation potential, and portfolio expansion opportunities. Contact for rent roll and financial information.

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

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

Remarks: Welcome to Garden Grove Oaks – a friendly, active 55+ community in beautiful Winter Haven and you OWN THE LAND! This well-maintained 2-bedroom, 2-bathroom manufactured home with a bonus office/den and Florida room offers the perfect blend of comfort, functionality, and easy Florida living. Step inside and you’ll immediately appreciate the bright, open layout, featuring a spacious living area ideal for relaxing or entertaining. The kitchen provides ample storage and prep space, while the adjoining dining area creates a natural flow for everyday living. Outside, you’ll enjoy a low-maintenance yard, covered parking, and plenty of room for outdoor seating. Garden Grove Oaks residents love the clubhouse, community pool & hot tub, social activities, and peaceful setting, all while being close to shopping, dining, medical facilities, and the best of Winter Haven. Whether you’re seeking a seasonal retreat or a year-round home, this charming property is move-in ready and waiting for you!

Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)

Listing Agent: Nicole Castro (863-547-5647)

Remarks: PRICE REDUCTION! Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage, tankless water heater, and leaf filter gutter guards. Ready for your finishing touches!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Under Construction. *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: Virtually Staged. Under Construction. Welcome to this stunning Poinciana floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2,110 square feet of living space, and provides excellent curb appeal in it's 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.

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

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

Remarks: Virtually Staged. Under Construction. Hillcrest floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,758 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.

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

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

Remarks: Virtually Staged. Under Construction. Ready by August 2026 The Bradley looks and feels bigger than 1,625 Sq. Ft. Is an open concept floor plan. Spacious master bathroom, dual vanity and a nice size closet. Nice upgrades included stone counters in kitchen and in all bathroom counters, tile in wet and common areas, 9'4" ceiling height and a lot more. Sample Image

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

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

Remarks: Under Construction. Brand new, energy-efficient home available by Jul 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. 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: Beautiful lake-view condo in Winterset! This ground-floor 2-bedroom, 2-bath residence offers amazing views of Lake Winterset, part of the renowned Winter Haven Chain of Lakes. The spacious great room features tile flooring, sliding glass doors to the screened porch, and stunning lakefront vistas. Just off the kitchen is a comfortable dining area, creating an inviting space for everyday living and entertaining. The kitchen is beautifully appointed with custom Kraft Maid wood cabinetry, granite countertops, a breakfast bar, and a complete appliance package. The primary bedroom enjoys peaceful lake views and includes plush carpeting with a gel pad, a large 11' X 7' walk-in closet, a ceiling fan, sliding doors to the patio, and an en-suite bath featuring dual sinks, quartz countertops, and an oversized walk-in shower with a seamless glass door. The guest bedroom is generously sized at 13' x 10', offering ample closet space and convenient access to the guest bathroom, which features quartz countertops and tile flooring. The screened porch is the perfect place to relax and enjoy breathtaking lakefront views and spectacular sunsets. Residents enjoy true resort-style living with access to a community clubhouse, pool, spa, shuffleboard courts, tennis & Pickleball courts. The highly desirable location offers close proximity to shopping, dining, schools, medical facilities, and LEGOLAND Florida Resort. Additional features include a private storage room off the patio, inside laundry, a tile roof, air conditioning, 24-hour security, meticulously maintained grounds, assigned parking, and ample guest parking. This is Florida lakefront living at its finest.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Chip Fortenberry, Iii (863-673-9368)

Remarks: NO CDD Fees • Low HOA • *Lower Taxes • Luxury Heated Pool • Resort-style backyard • Move-In Ready Home. Welcome to this beautifully maintained and gently lived-in upscale home situated on an oversized 70’ wide homesite in a desirable community offering low HOA fees and *lower property taxes. Designed for both comfort and entertaining, this expansive 4-bedroom, 3.5-bath, two-story home has approximately 2,894 sq. ft. of thoughtfully designed living space, including TWO primary suites — one conveniently located on the first floor with a luxury bath and spacious walk-in closet, and a second upstairs primary suite featuring its own full bath and walk-in closet. The first floor also includes a versatile enclosed flex room which can be used as a home office, guest room, or potential 5th bedroom. The second floor has three other bedrooms with walk-in closet and oversized loft about 21'x17'. Step outside into your private resort-style backyard featuring a heated, fully automated full-size pool and spa with premium PebbleTec finish, already prepped for expansion with a concrete footer for future screen enclosure installation, upgraded pavers, large covered lanai, gutters and downspouts for improved drainage, fully fenced yard and extended front porch — creating the perfect Florida outdoor living experience— for entertaining, relaxing, pets, and family gatherings. Inside, the open-concept kitchen is beautifully upgraded with: • premium color cabinets, • oversized island, • stylish backsplash, • single-bowl sink, • granite countertops, • pendant lighting, • and stainless-steel appliances. Additional interior highlights include: • recessed LED lighting throughout, • tile flooring in wet areas, kitchen, hallway, and gathering room, • exterior-vented microwave, • and abundant natural light throughout. This truly move-in-ready home includes: • first-floor family room sofa set with wall-mounted 75” TV, • upstairs loft recliner sofa set with wall-mounted 75” TV, • refrigerator, washer, dryer, and window blinds, • home alarm system, • outdoor security cameras, • video doorbell, • and remote thermostat. Additional peace of mind includes: • transferable Pulte Homes 5/10-year warranty, • and 1 year of complimentary pool maintenance. This home has the perfect blend of luxury, functionality, and convenience in a family-friendly community with a safe small-town feel while remaining close to shopping, dining, everyday amenities and just minutes away from Legoland. READY TO MOVE IN. *Some photos have been virtually rendered.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)