Homes For Sale in Winter Haven 33881 - 289 homes

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 1598 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: 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: This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and a large backyard—ideal for entertaining or relaxing outdoors. This home is light and bright and move-in ready just for you! The kitchen features white raised-panel PVC cabinetry, black tile countertops, a closet pantry, and updated appliances including a refrigerator (2026) and stove (2022). Major system upgrades include a new 3.5-ton A/C system with new ductwork and a roof replaced in 2022. The split-bedroom layout offers privacy, with both bathrooms very nicely updated. The spacious primary suite includes a beautiful bath with stone floors, a quartz vanity with integral sink and wall-mounted faucet, and a walk-in shower with new tile, glass doors, and drain pan—part of a $15,000 renovation. Additional highlights include a garage with mini-split A/C, insulated garage door, pull-down ladder for attic access, washer/dryer hookup, and laundry sink. Outside you will have a 10’x12’ shed with electric, and a well house with a Culligan water softener system. A new black aluminum fence surrounds the property, with vinyl PVC privacy fencing along the left side, 12-foot gates on both sides plus a 6-foot front gate—perfect for storing a boat, RV, or extra vehicles. A covered rear carport adds even more flexibility. Conveniently located on a large corner lot near lakes, parks, recreation areas, LEGOLAND, Hwy 27 & I-4, and all that Central Florida has to offer. Welcome home!

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

Listing Agent: Russ Rhoads (863-604-1570)

Remarks: EXCELLENT HOME!!! GREAT INVESTMENT OPPORTUNITY!! MUST SEE THIS HOME!

Listing is courtesy of: ONE TEAM REALTY (407-530-5006)

Listing Agent: Roque Acevedo (347-867-7070)

Remarks: Welcome to 525 Winter Terrace in Winter Haven, an inviting, move-in-ready 2-bedroom, 2-bath, single-level townhouse in a maintenance-free family community with outstanding amenities. Step inside to find ceramic tile throughout the main living areas, spacious bedrooms, and a bright Florida room perfect for relaxing or entertaining. The heart of the home is the completely updated kitchen featuring nice appliances, wood cabinetry, and granite countertops, complemented by neutral interior paint and updated tile. Enjoy even more comfortable living space in the enclosed back room, offering additional air-conditioned square footage. The primary suite has sliding glass doors that lead to your own, private, enclosed porch. Community perks include a clubhouse, solar-heated pool, shuffleboard, and a private boat dock on beautiful Lake Smart. Schedule your showing today because this one won’t last long!

Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)

Listing Agent: Oralis Perez (407-325-1045)

Remarks: Discover the best of retirement living in Brookhaven, a welcoming 55+ community! This partially furnished and well-maintained home sits on a desirable lot with OWNED LAND, offering a peaceful and private retreat.Featuring 1,596 sq. ft. of living space, this home boasts a spacious open-concept layout with 2 bedrooms and 2 bathrooms. Recent updates include a new shingle roof (2024), new A/C unit (2025), and hot water heater (2023). The kitchen offers ample counter space and cabinetry, perfect for everyday living and entertaining.Enjoy plenty of storage throughout, along with sliding doors that lead to the porch—ideal for relaxing or hosting guests. The guest bedroom and bathroom are generously sized, while the oversized primary suite features a private ensuite bath complete with a double-sink vanity, garden tub, and walk-in shower.The laundry area is conveniently located in the spacious workshop and includes a washer, dryer, and utility sink. This home also features two porches—one screened and one enclosed—providing additional living space to enjoy year-round.Surrounded by mature landscaping, the property offers both charm and tranquility. Additional perks include an irrigation system and lawn maintenance already paid through February. This home has recently had a 4-point inspection.Brookhaven residents enjoy fantastic amenities including a pool, clubhouse, and shuffleboard—all with a low HOA fee of just $34 per month. Conveniently located near Hwy 27, shopping, medical facilities, and restaurants, you’re also just about an hour from Disney and 1.5–2 hours from both Florida coasts.Don’t miss your opportunity to own this beautiful home at 6561 Chinaberry Dr NE — schedule your private showing today!

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

Listing Agent: Corinna Weaver (863-258-2901)

Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning Winston floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 5-bedroom, 3-bath home offers 2,531 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz counter tops 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: 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: MULBERRY model is located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2 and a half-bath home offers 1,938 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous gray cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. The open layout is perfect for family gatherings and entertaining guests. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.

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

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

Remarks: Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community — ready for a new owner. Single-level, move-in ready home with a bright, open floorplan, remodeled kitchen and stainless steel appliances. Durable LVP flooring (2021) throughout the main living areas and new carpet in the bedrooms. Laundry includes washer/dryer 2021; refrigerator 2025. Security system installed. Major recent system and structural upgrades for worry-free ownership: HVAC 2023; 40-gal water heater 2023; PEX water lines 2024; new carport roof 2024; new power panel & upgraded wiring 2021; attic insulation & interior paint 2021. Ease of living: Enjoy true low-maintenance, single-level living with HOA exterior care, easy parking under the new carport roof, and modern systems that minimize upkeep and unexpected expenses. The thoughtful updates and security system provide peace of mind and allow you to spend more time enjoying community amenities, nearby lakes, dining, and shopping rather than home maintenance. Location and lifestyle: Conveniently close to Publix, dining, and scenic lakes — ideal for active adults seeking convenience and leisure.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Holly Patterson (717-668-9598)

Remarks: Big Price Drops and Price to sell. Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. This property features a newer roof put on in 2023, a newer in-ground pool put in 2022, and a large backyard shed, offering the perfect blend of comfort, storage, and outdoor enjoyment. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

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

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: Another Great Listing brought to you by Paul Jacques, P.A. EveryThing Real Estate. Gated Community, Like New. Open floor plan. minutes from downtown Winter Haven. Low HOA, you’ll enjoy neighborhood security and amenities without the extra cost. Commuters will love the quick access to Hwy 27, providing an easy drive to area beaches, Orlando’s theme parks, and more. Price To Sell.

Listing is courtesy of: XCELLENCE REALTY INC. (866-595-6025)

Listing Agent: Paul Jacques (561-441-9695)

Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT! SELLER MOTIVATED! Completed in 2020 and ready for immediate occupancy, this property blends modern construction with thoughtful recent upgrades. Notable features include a brand-new roof installed in 2023, fully paid solar panels, a freshly painted interior, and professionally serviced and cleaned air ducts, all contributing to energy efficiency and average utility costs of approximately $85–$100 a month. The home is equipped with smart home technology and constructed with concrete block on both the first and second floors, offering added durability and peace of mind. Inside, the kitchen opens naturally to the main living spaces, creating an inviting layout for everyday living and entertaining. A future flooring update provides an easy opportunity to personalize the space. Bedrooms are generously sized, with the primary suite located upstairs, and a fully fenced backyard enhances privacy and functionality. Ideally positioned within the community, the home is just a short walk to the mailbox, pool, and playground, with convenient access to shopping, dining, grocery stores, major roadways, just a short drive to LEGOLAND® and less then one hour from Walt Disney World.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Kristin Duncan (407-274-5911)

Remarks: This charming 2-bedroom, 2-bath condo offers the perfect blend of comfort and convenience with a layout designed for effortless living. Enjoy a spacious living area, light-filled interiors, and a private outdoor space perfect for morning coffee or evening wind-downs. Located just minutes from Winter Haven’s famous Chain of Lakes, local dining, shopping, and everyday essentials, this is the ideal spot for year-round living, a seasonal retreat, or a smart investment. Low maintenance. Prime location. Relaxed lifestyle. *This home can be purchased with NO INCOME VERIFICATION*

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

Listing Agent: Donna Fiore (904-228-0198)

Remarks: Welcome To Hartridge Hills!! This Gorgeous Gated Community is one of Polk County's Hidden Treasures. An established and well maintained community of charming custom homes, each one uniquely it's own. Nestled between Lake Pansy and Lake Hartridge, this community offers boat lovers their own private boat ramp with access to the Chain of Lakes. This community also has been home to many pilots over the years and is conveniently located beside the Winter Haven Airport and only minutes to Publix and all major medical facilities making this community a perfect location. Situated on a corner lot, this well built home by Ernie White is a split plan offering 3 bedrooms & 2 baths plus a den or office space. The dining room, living area and bedrooms have new luxury vinyl. There is High ceilings throughout, crown molding, updated granite in the kitchen and bathrooms. The roof was replaced in 2017. HOA fee's include lawn care and the irrigation system is on a small well, saving you money on your water bill! Grab your favorite beverage & Relax and Enjoy the water views on your enclosed back lanai. Come check out this beautiful property, You'll love being a part of this quaint community!!

Listing is courtesy of: PREMIER HOMES AND REAL ESTATE (863-937-8942)

Listing Agent: Christy Smith (863-409-8709)

Remarks: Welcome home! This cheerful 3-bedroom, 2-bath beauty is just four years young and sits in the sought-after community of Lucerne Park Reserve. Step inside and you’ll be greeted by bright open spaces and plenty of space for the whole family. The island kitchen is ready for real everyday living with stainless steel appliances and a roomy pantry that keeps everything in its place. The primary suite offers a comfortable retreat with a walk-in closet and a comfortable walk-in shower featuring a dual-sink vanity. With its split floor plan, you’ll also enjoy two additional bedrooms, a second full bath, and the convenience of an indoor laundry room. Out back, the covered porch gives you a relaxing spot to unwind and soak up that famous Florida sunshine. You’ll be less than 10 minutes from Highway 27 and only about 20 minutes from Legoland—making everyday errands and weekend fun easy. This is a solid home in a community people love. Schedule your showing today—you don’t want to let this one slip by.

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

Listing Agent: Luis Colon, Jr (407-748-2765)

Remarks: Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of the Chain of Lakes. This spacious 2BR/2.5BA townhome offers approximately 2,045 sq ft of living space with vaulted ceilings, abundant natural light, and a functional two-story layout. The main level features an open living area with sliding glass doors leading to a private covered patio, plus a well-appointed kitchen with breakfast bar and a convenient half bath. Upstairs, enjoy a versatile loft/bonus space ideal for a home office or additional living area. Both bedrooms offer ensuite bathrooms, including a primary suite with a private screened balcony. Additional highlights include ceramic tile and hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor, and multiple outdoor spaces including three patios. Recent updates include the ROOF (Aug 2023). Owner is offering a $5,000 credit towards flooring. Residents enjoy resort style amenities: community pool, tennis courts, boat slip, and dock with direct access to Lake Cannon and the Chain of Lakes, perfect for boating, fishing, and waterfront living. Prime location near shopping, dining, and major roadways. Low-maintenance living in a secure, gated community.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor living, and boating amenities. The main home features three bedrooms and two bathrooms with an open and functional layout. A bonus room with built in entertainment cabinetry and surround sound opens through double sliding doors to the pool deck, creating seamless indoor-outdoor living. The living room showcases beautiful wood beams, a wood burning brick fireplace, and triple sliding glass doors overlooking the pool and lake. Tile flooring runs throughout the main living areas, with wood flooring in the bedrooms. The kitchen is designed for everyday living and entertaining, featuring granite countertops, updated cabinetry with pullouts, a large island, built in desk space, wine refrigerator, stainless steel appliances, and a built-in oven/microwave combination. A separate guest studio apartment adds flexibility, complete with a kitchenette and triple sliding glass doors leading directly to the pool area. This space is ideal for guests, extended household needs, or flexible use. Outdoor features include a screened pool with new heater and an 8-foot depth, a spa that conveys, and a gas fireplace on the patio with underground piping in place (propane tank has been removed, but can easily be replaced by the new homeowner). The pool screen was recently replaced. The property includes a private boat dock and lift, allowing easy access to Lake Hamilton and nearby lakefront restaurants by water. Additional highlights include fruit trees in the front yard, RV parking for up to 31 feet with additional storage space, and a metal roof. Practical upgrades and systems include a new air conditioning system installed July 2024 with annual maintenance, water softener, well for irrigation, public water for the home, an inside laundry room, and a 2-car garage. The hot water heater was installed in 2011. Septic service was last completed June 2023. Solar panels are leased at $381.75 per month, with an average Duke Energy bill of approximately $30 per month. Televisions in the main living areas convey, excluding bedrooms. This lakefront retreat offers privacy, functionality, and a connection to the water, all set along beautiful winding roads in a peaceful Winter Haven setting.

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

Listing Agent: Lisa Matheny (863-412-6633)

Remarks: Spacious single-family home featuring 4 bedrooms and 2.5 bathrooms with approximately 3,160 sq ft of living space, offering a functional and flexible floor plan. The main level includes a private office with French doors, ideal for use as a home office or optional fifth bedroom. Generous interior spaces provide comfortable living and well-sized bedrooms throughout. Conveniently located in Winter Haven, with easy access to major roads, shopping, dining, and everyday conveniences. This property offers an excellent opportunity for buyers seeking space, versatility, and a well-established residential setting.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Maria Chavez (407-866-4682)

Remarks: Welcome to this charming 3 bedroom, 1 bath home ideally located in the heart of Winter Haven, just minutes from shopping, dining, and schools. From the moment you arrive, you’ll be greeted by a lush, established front garden, perfect for those who enjoy outdoor living or gardening. The home features a covered front porch, ideal for relaxing mornings or unwinding in the evenings, along with a convenient one-car carport. Inside, you’ll find a warm and inviting living space highlighted by durable wood-look tile flooring that flows seamlessly throughout the main areas. The kitchen and dining room combination offers a functional layout with plenty of room for everyday living and entertaining. Tucked away at the rear of the home, the spacious primary bedroom provides added privacy and a generously sized closet. Two additional bedrooms offer flexibility for guests, a home office, or hobby space. The full bathroom includes a single-sink vanity and a tiled tub/shower combo. Additional features include an exterior storage/laundry room located under the carport with washer and dryer hookups. Whether you're a first-time homebuyer, investor, or looking to downsize, this home offers great potential and opportunity. Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Casandra Vann (863-546-5446)