Winter Haven Homes For Sale & Real Estate - 982 homes

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: 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: Discover this must-see Tarragon home. Included features: an inviting covered entry; an expansive great room; a quiet study; a well-appointed kitchen offering quartz countertops, stainless-steel appliances, 42" cabinets, a walk-in pantry, a center island and an adjacent dining area; a convenient laundry; an impressive primary suite showcasing a spacious walk-in closet and a private bath; a mudroom and an extended covered patio. This could be your dream home! *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and two private outdoor living areas. An attached two-car garage provides added convenience. Upstairs, you’ll find two spacious bedroom suites each with a private en-suite bath, as well as a versatile loft area. Step out to the screened balcony or the open upper deck, perfect for enjoying tranquil lake views and evening breezes. Community amenities include a swimming pool with spa, tennis court, lakeside dock, beach area, and a gated entry with electronic access. Whether you're seeking a seasonal retreat or a full-time residence, this unique property offers comfort, style, and a desirable location.

Listing is courtesy of: DREAM BUILDERS REALTY (407-847-5428)

Listing Agent: Tim Weisheyer (407-847-5428)

Remarks: Under contract-accepting backup offers. Great investment opportunity just minutes from downtown Winter Haven. This well-maintained, fully leased duplex offers immediate cash flow with strong rental demand in a prime location near shopping, dining, and major roadways—a turnkey property ideal for investors seeking stable income and long-term appreciation. Seller is willing to provide the buyer with credit toward a roof replacement if necessary.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Joshua Taylor (863-651-5471)

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: This 4/2 home has a renovated interior showcasing modern upgrades throughout. The home features stunning new 36" x 24" porcelain tile flooring, offering a sleek, contemporary look with durability and easy maintenance. Move-in ready and designed for comfortable, stylish living. Dual access bedroom and bath provides the bedroom with private ensuite access while allowing the bathroom to serve as a main or guest bathroom from the hall, featuring two doors to maximize access and functionality. Large kitchen with island and lots of cabinet space and large pantry. Sliding doors leading to covered screened in porch with additional concreted tiled patio area that leads to a large backyard. Seller will consider contributing toward buyer’s closing costs.

Listing is courtesy of: EASY REALTY (321-895-4636)

Listing Agent: Greg Owen (321-360-4434)

Remarks: Under contract-accepting backup offers. BEAT NEW CONSTRUCTION COSTS! Seller offering up to $7,000 toward closing costs, prepaid expenses, or interest rate buydown; helping reduce your cash to close and monthly payment. Move-in ready with NO CDD!This beautifully updated 3-bedroom, 2-bathroom home with a bonus room is ideally located just minutes from LEGOLAND Florida, as well as shopping, restaurants, hospitals, and major attractions. Whether you're looking for a primary residence, vacation home, or investment opportunity, this property delivers comfort, space, and modern upgrades. Step inside to a bright, interior featuring new ceramic tile flooring throughout the entire home (absolutely NO carpet), offering easy maintenance and a clean, modern look. The homehas been freshly painted and thoughtfully updated to feel truly move-in ready. The renovated kitchen features new cabinetry, granite countertops, stainless steel appliances, a spacious pantry, and a breakfast nook perfect for casual meals. For hosting and special occasions, enjoy a formal dining room that adds both function and elegance.The spacious primary suite is a true retreat, offering a beautifully appointed en-suite bathroom with double sinks (ideal for busy mornings), granite countertops, an enclosed shower, and a relaxing garden tub.Both bathrooms have been upgraded with new cabinets and granite countertops, adding a cohesive and modern finish throughout the home. A versatile bonus room provides the perfect space for a home office, playroom, gym, or guest area. For added convenience, the laundry room is located inside the home.Step outside to the screened lanai, overlooking a generous lot being an ideal setting for weekend BBQs, family gatherings, or simpl enjoying Florida?s indoor-outdoor lifestyle.This home combines modern upgrades, flexible living spaces, and an unbeatable location near LEGOLAND Florida. With both roof & HVAC replaced in 2024 there is reassurance of major system being warranted - A must-see property!

Listing is courtesy of: EASY REALTY (321-895-4636)

Listing Agent: Greg Owen (321-360-4434)

Remarks: Short Sale. Welcome to this charming three-bedroom, two-bathroom home, perfectly situated for comfortable living. The inviting open concept layout seamlessly integrates the kitchen, living, and dining areas, adorned with luxury vinyl plank flooring that adds both style and durability. The well-appointed kitchen features beautiful granite countertops, complemented by sleek black appliances, crisp white cabinets, and a classic white subway tile backsplash, along with a convenient counter-height breakfast bar for casual dining. With significant updates including a new roof, air conditioner, and water heater all installed in 2022, this home offers peace of mind for future years. Enjoy the ease of laundry access off the carport and relax in the privacy of the fenced backyard. With a one-car carport and a warm, welcoming ambiance, this home is a delightful find for anyone seeking a cozy retreat.

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

Listing Agent: David Small (407-601-8351)

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 3 bedroom 2 bath home is located in an established neighborhood close to the Polk parkway for easy access to Orlando or Tampa. The Kitchen is equipped with stainless steel appliances, wood cabinets, granite counter tops, breakfast bar. There is a fire place and a wet bar in the large living room with beautiful tile & wood flooring throughout the home. The back porch is screened and the entire backyard is beautifully landscaped with mature landscaping, various trees and surrounded with a brick wall. There is also a detached workshop that is completely finished with tile floors and air conditioning. The home features a gas tankless hot water heater and smart lock on the doors.

Listing is courtesy of: THOMAS REALTY (863-412-4253)

Listing Agent: Phillip Thomas (863-412-4253)

Remarks: Short Sale. ***Short sale***Spacious 4-bedroom, 2-bathroom manufactured home with strong bones and endless potential! Featuring a newer AC unit and a roof less than 5 years old, this property is a great opportunity for a savvy buyer ready to bring their vision to life. Whether you're looking to create your forever home or an investment property, this one is worth a look. The primary suite offers a walk-in closet and a luxurious garden tub, perfect for relaxing after a long day. Situated on just under half an acre, there’s ample space for outdoor living, gardening, or future enhancements. Bring your eye for design and turn this home into something truly special!

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Tony Acosta (863-224-5956)

Remarks: A Cozy Condo nestled in the back corner of the popular community of Winterset. Forgot your key, no problem, you have a coded keyless entry. Your tour begins entering through your covered screened front porch into a Ground level 2 bed/2bath home with an open floor plan. Beautiful Laminate wood flooring accentuates the space. The conveniently centered kitchen boasts a neutral decor with tile backsplash and a newer Stainless side by side fridge. A Nice size Patio is accessed from Livingroom for Barbecuing or just relaxing, enjoying the Florida weather. The split bedroom design offers added privacy to The Master Bedrm with en suite, spacious Walkin closet, Stackable washer/dryer and private screened in patio area which continues to enhance this space. The master bath has separate tub/shower access. The Nest thermostat allows you to monitor and change settings via a phone app. When you Plan your day trips.... You're Only minutes from Lego Land and convenient to Disney & other Florida amusement parks, Beaches, Shopping, Restaurants & More. Or, stay at home, relax and enjoy amenities of the community with Heated Pool, Spa, Tennis, Shuffleboard, Fishing Pier and Clubhouse! Walk the family pet across the street in the expansive green space. All Furniture negotiable!

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

Listing Agent: Catrina Marshall (813-377-7380)

Remarks: Amazing potential. This 2-bedroom, 2-bathroom townhouse features a spacious 1,252 square foot floor plan and is located in the established Stonebridge community.

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

Listing Agent: Sarah Armstrong (863-287-0252)

Remarks: One or more photo(s) has been virtually staged. Charming single-story home located in Winter Haven with a functional layout and comfortable living spaces throughout. This 3-bedroom, 1-bath property features an inviting living area filled with natural light, a spacious kitchen with ample cabinet and counter space, and tile flooring throughout for easy maintenance. The home also offers a covered parking area, paved driveway, and a generously sized yard with room to enjoy outdoor living. Conveniently located near shopping, dining, parks, lakes, and major roadways for an easy commute throughout Polk County.

Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)

Listing Agent: Raquel Littlejohn (470-279-6333)

Remarks: One or more photo(s) has been virtually staged. Welcome to 306 Ave P NW – a fantastic opportunity for first-time home buyers or savvy investors! Now offered as separate units for added affordability and flexibility, this property is perfect for buyers looking to own instead of rent. This well-maintained home features bright living spaces, functional layouts, and great potential to personalize and build equity. Whether you’re looking for your first home, a mortgage helper opportunity, or an affordable investment, this property checks all the boxes. Located in a convenient neighborhood close to schools, parks, shopping, and everyday amenities, you’ll love the value and potential this property offers. Why rent when you can own? Don’t miss your chance to get into the market with this affordable and versatile property. Quick possession available — motivated seller!

Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)

Listing Agent: Ricky Miller, Jr (407-453-8679)

Remarks: Welcome to 3588 Raleigh Dr! Located within the gated 55+ community of Traditions, this well-maintained corner-lot home offers a blend of comfort, functionality, and resort-style living. The residence features two bedrooms, two bathrooms, and more than 1,700 square feet of open living space designed to accommodate both everyday living and entertaining. It boasts an open floor plan with spacious living & dining areas flowing directly into the fully equipped kitchen. The entire area creates the heart of the home and lends ample room for gathering. Each bedroom is spacious and a split layout provides privacy for everyone. You'll especially love the master suite which has brand new carpet, a walk-in closet, a full private bathroom with dual sink vanity, a step-in shower, and a siding glass door leading out to the lanai. An enclosed lanai extends the living space and offers a relaxing spot to enjoy the outdoors year-round. A pavered courtyard with established landscaping adds privacy and a peaceful atmosphere. Major system updates include a new roof (2023), water heater (2023), and A/C (2021). Traditions offers an impressive selection of amenities, highlighted by a 19,000-square-foot lakefront clubhouse featuring a heated swimming pool, spa, fitness center, sauna, billiards room, craft rooms, library, and ballroom. Residents also enjoy walking trails, tennis and pickleball courts, shuffleboard, and basketball courts. Direct lake access includes a community boat ramp and docks, ideal for boating and fishing enthusiasts. The monthly HOA fee includes lawn maintenance, cable, internet, and exterior home painting, supporting a low-maintenance lifestyle. Located close to Hwy 27, golf courses, restaurants, and anticipating a brand new Publix just around the corner, this place truly offers Adult Florida living lifestyle at its finest!

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

Listing Agent: Cindy Strouse (863-581-1605)

Remarks: Welcome to 2213 Rose Blvd in Winter Haven—a beautifully maintained and like-new 4 bedroom, 2 bath home offering over 1850 square feet of comfortable living within the Buckeye Ridge community. Perfectly positioned on a corner lot, this home showcases outstanding curb appeal and evident pride of ownership, enhanced by a freshly painted exterior accents, well cared for landscaping, decorative gable vents and carriage-style garage hardware for a custom look. A thoughtfully designed split-bedroom layout with open-concept living at its core, offering a seamless flow for everyday living and entertaining while maintaining privacy with a well-separated primary suite and generously sized secondary bedrooms. Tile flooring leads from the foyer into the great room and kitchen area, where brand-new wood laminate flooring and roomy dimensions provide an ideal level of easy living. The kitchen features an abundance of cabinetry and counter space, breakfast bar/center island, a walk-in pantry and included appliances. Dining space sits just off the kitchen with tranquil backyard views. The triple split-bedroom layout provides privacy and flexibility, highlighted by a generously sized primary suite with brand-new carpeting, a walk-in closet, and an en-suite bath complete with dual vanities, walk-in shower, large linen closet and private water closet. All guest bedrooms also have brand new carpeting and are spacious with easy access to the full guest bath. Step outside to your private outdoor oasis—featuring a screened patio that opens to a fully fenced backyard with vinyl fencing and irrigation system with timer to keep the yard green and lush—perfect for relaxing or hosting gatherings year-round. Additional notable features include an inside laundry room, double-pane windows, two-car garage, warranties on the new flooring, both gas and battery generator connections and a transfer switch for added peace of mind. Location is everything, and this home delivers—just minutes from vibrant downtown Winter Haven, Polk State College, medical facilities, shopping, restaurants as well as multiple golf courses and lakes to fully enjoy the Central Florida lifestyle. Centrally located between Orlando and Tampa, Winter Haven offers the perfect balance of small-town charm with convenient access to major roadways, shopping, dining, and world-class attractions. Homes in this condition with an ideal combination of upgrades and location are hard to find—schedule your private showing today!

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

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

Remarks: Under contract-accepting backup offers. Beautifully renovated property in an excellent and highly desirable location. This home features modern finishes throughout, including a stunning quartz kitchen countertop and brand-new appliances. Conveniently located near hospitals, medical offices, major avenues, schools, restaurants, and shopping centers. Its strategic location offers great versatility, making it ideal for both residential living and potential commercial use. A rare opportunity to own a fully updated property in a prime area.

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Graceshaly Collazo (939-441-3991)

Remarks: WELCOME HOME to this beautifully updated 3-bedroom, 2-bath residence located in the pristine gated community of Cypresswood! From the moment you enter the neighborhood, you’ll feel the charm of this private, resort-style community nestled in the heart of Polk County—just minutes from US Hwy 27, providing easy access to all that Central Florida has to offer. Step through the front door into a grand foyer with soaring ceilings that opens to a spacious, light-filled living room—perfect for entertaining guests or enjoying quiet evenings at home. The kitchen is designed to impress, featuring beautiful cabinetry, abundant pantry space, and brand-new stainless steel appliances that elevate both style and functionality. Just off the kitchen, the oversized laundry room offers even more storage along with a convenient laundry sink. On the opposite side, a charming breakfast nook overlooks the large backyard—ideal for morning coffee or casual dining. The generously sized primary suite is a true retreat, complete with an expansive walk-in closet, dual vanities, a walk-in shower, and private access to the screened lanai—perfect for enjoying Florida evenings. Bedrooms two and three both feature double closets, providing plenty of storage space for family or guests. Major updates give you peace of mind for years to come, including the roof (2021), new A/C (2024), gas water heater 2021, new stainless appliances. This move-in-ready gem offers comfort, style, and thoughtful upgrades in one of the area’s most desirable golf communities which include an 18 hole champion designed course, pro shop, wellness center, Pub/restaurant, clubhouse, swimming pool and more! Don’t miss your opportunity to make it yours—schedule your private showing today!

Listing is courtesy of: INFINITE REAL ESTATE POWERED BY ILIST (321-689-8731)

Listing Agent: Michelle Keohane (850-866-5905)