Winter Haven Single Family Homes For Sale - 760 homes

Remarks: One or more photo(s) has been virtually staged. Discover the perfect blend of modern updates and serene living in this stunning 4-bedroom, 2-bathroom home. Located in the highly sought-after Country Club Estates, this residence offers the privacy you've been searching for with a screened-in back patio overlooking a peaceful pond-meaning no rear neighbors, just tranquil water views. Step inside to find a bright and airy open floor plan, freshly enhanced with new interior and exterior paint. The home is designed for both style and durability: Elegant luxury vinyl plank in all bedrooms and easy-to-maintain ceramic tile throughout the main living areas. Features timeless oak cabinetry, sleek granite countertops, and plenty of prep space. The popular split-bedroom floor plan ensures a private primary retreat, separate from the guest rooms.A dedicated inside laundry room and a spacious 2-car garage provide ultimate functionality. Location is everything! Enjoy the quiet atmosphere of an established community while being just moments away from modern conveniences. The brand-new Publix shopping center is right around the corner, making grocery runs and errands a breeze.Schedule your private showing today and experience Florida living at its finest!

Listing is courtesy of: ORLANDO REO PROF I INC (407-704-6924)

Listing Agent: Ronald Gentile (407-247-0849)

Remarks: Welcome to 3006 Elm Street in beautiful Winter Haven — a charming home full of potential and perfectly positioned for convenience! This 3-bedroom, 1.5-bath home also features a flexible office space that could easily serve as a 4th bedroom, playroom, hobby room, or home gym. Step inside to find new tile flooring, a remodeled bathroom, a newer roof, and updated ceilings that give the home a fresh and modern feel. The spacious kitchen offers plenty of room to cook, gather, and get creative with your dream design ideas. Outside, the backyard is a blank canvas ready for your personal touch — create the garden, outdoor kitchen, pool area, or entertaining space you've always wanted! Conveniently located near shopping, dining, attractions, and with easy access for commuting to both Tampa and Orlando, this property offers the perfect blend of comfort, opportunity, and location. Whether you're looking for your first home, investment property, or extra space to grow, this Winter Haven gem is ready to welcome you home!

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

Listing Agent: Michele Elchin (863-514-6880)

Remarks: You will be impressed the moment you walk through the door! It’s so clean, polished and move-in ready! This home is a beautifully maintained 3-bedroom, 2-bath home located in the desirable Morningside neighborhood within the gated Winterset community. This thoughtfully designed split-bedroom floor plan offers both comfort and functionality, featuring a formal living room, formal dining room, and a spacious great room ideal for everyday living and entertaining. There is opportunity for lots of natural light with the storm front door and the garage screening. Both the garage and lanai screenings were replaced in 2024 when exterior paint was completed. The kitchen is conveniently positioned with a nearby laundry closet and flows seamlessly into the main living areas. Two secondary bedrooms share a well-appointed hall bath, providing privacy for family or guests. The primary suite is a true retreat, complete with sliding glass doors leading to the Florida room, dual walk-in closets, and a luxurious en-suite bath featuring a soaking tub, separate shower, and ample space. Enjoy year-round relaxation in the expansive Florida room, perfect for a seating area and dining setup, all overlooking a generously sized backyard. This home has been thoughtfully updated and is move-in ready with new carpet throughout (2026), giving it a fresh, like-new feel. Additional updates include: Refrigerator (2023) Garage door opener (2020) Garbage disposal (December 2023) Exterior paint (September 2024) Water heater (September 2024) HVAC system (2014) Winterset offers resort-style amenities including a gated entrance, community pool, tennis courts, scenic lake views, and a private boat ramp. Conveniently located in SE Winter Haven just off Cypress Gardens Blvd, you’ll enjoy easy access to shopping, dining, and local events. Don’t miss the opportunity to own this exceptional home in one of the area’s most sought-after communities!

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

Listing Agent: Karen Myers (863-651-4636)

Remarks: ""SELLER MOTIVATED – PRICE IMPROVEMENT! BRING YOUR OFFER!"" Beautiful and well-maintained home featuring 4 spacious bedrooms and 2 bathrooms, offering plenty of space for comfortable family living and entertaining guests. Sliding glass doors lead to a covered patio and a private grassy backyard, perfect for relaxing and enjoying Florida’s outdoor lifestyle. The kitchen comes fully equipped with all appliances and features beautiful wood cabinetry and granite countertops, offering the perfect blend of style and functionality. The home also includes a 2-car garage and a fully equipped laundry room for added convenience. Located in a desirable community, this property offers comfort, practicality, and excellent investment potential. Conveniently located near LEGOLAND Florida Resort, Chain of Lakes Park, Downtown Winter Haven, shopping centers, restaurants, grocery stores, medical facilities, and provides easy access to Highway 27 for convenient travel to Orlando and Tampa. Winter Haven is also known for its beautiful Chain of Lakes, offering boating, fishing, and outdoor recreation opportunities. Currently tenant-occupied with a lease in place through November 2026 at $2,150 per month. After the lease term ends, the new owner may choose to renew or terminate the lease. Great opportunity for both investors and future homeowners.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Anderson Siqueira, Sr (407-912-4688)

Remarks: Welcome to this beautifully renovated home located in a secure gated community, offering not only privacy and peace of mind but also a low annual HOA fee. This spacious property features 4 bedrooms plus a versatile bonus room and 3 fully remodeled bathrooms, thoughtfully designed to provide comfort for everyday living and privacy for guests. As you enter, you are welcomed by high ceilings and an open-concept layout filled with natural light, creating a bright and inviting atmosphere throughout the home. The interior showcases new flooring, fresh paint, and modern finishes that elevate every space. The kitchen has been fully updated with elegant cabinetry, gold hardware, spacious countertops, stainless steel appliances, and stylish lighting, all seamlessly connected to the main living areas, making it ideal for both daily use and entertaining. Both the kitchen and bathroom countertops feature high-quality quartz, offering durability, low maintenance, and a clean, modern look that enhances the overall design of the home. The primary bathroom offers a true luxury experience with floor-to-ceiling tile, a freestanding soaking tub positioned under a large window, a frameless glass shower with modern gold finishes, and a double vanity with contemporary mirrors and lighting. The additional bathrooms have also been completely renovated with clean, modern designs and high-quality materials. The home also includes a three-car garage and a large driveway, providing ample parking and storage space. The backyard offers a private outdoor area with plenty of potential for relaxation or future enhancements. Located in a quiet and well-maintained community, this property combines modern upgrades, functional layout, and an excellent location, making it a perfect option for both homeowners and investors seeking a move-in ready home.

Listing is courtesy of: AVENUE HOMES LLC (833-499-2980)

Listing Agent: Jorge Orama (813-753-4656)

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 to this beautifully maintained newer home in the desirable Squires Grove community of Winter Haven! Built in 2022, this spacious 3-bedroom, 2-bath residence offers an open-concept layout with a bright living and dining area—perfect for entertaining. The modern kitchen features ample cabinetry, sleek appliances, and a large island overlooking the main living space. A split-bedroom floor plan provides privacy, with a generous primary suite including a walk-in closet and en-suite bath. Enjoy outdoor living in the private backyard with room to relax or host gatherings. Additional highlights include a 2-car garage, indoor laundry, and energy-efficient construction. Conveniently located near shopping, dining, schools, and major roadways, this home offers comfort, style, and convenience in one of Winter Haven’s growing communities.

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

Listing Agent: Danielle Williams (813-297-8258)

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: 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: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 2018-built single-family home located at 1327 Salisbury Drive in Winter Haven. Offering approximately 2,300 square feet of living space, this spacious residence features 5 bedrooms, 3.5 bathrooms, and a two-car garage. The primary suite is conveniently located on the first floor, providing privacy and comfort, while the upstairs bedrooms are carpeted for a warm, cozy feel. The interior has been freshly painted, creating a bright and move-in-ready atmosphere throughout. Enjoy Florida living year-round from the screened-in back patio, perfect for relaxing or entertaining. It is conveniently located just minutes from downtown Winter Haven and close to the area’s picturesque lakes, shopping, dining, and major roadways. This home combines modern construction, generous space, and an excellent location. Schedule your private showing today!

Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)

Listing Agent: Joshua Nogowski (754-234-9626)

Remarks: Seller motivated — great opportunity for investors or future homeowners! This beautiful corner lot home features 4 bedrooms and 2 bathrooms, offering comfort, space, and excellent income potential. The spacious kitchen comes fully equipped with all appliances, including a refrigerator, stove, microwave, and dishwasher, making it move-in ready from day one. The open-concept layout seamlessly connects the living and dining areas, creating the perfect space for entertaining guests or enjoying everyday family life. Sliding glass doors lead to a large backyard, ideal for outdoor activities, gatherings, or simply relaxing. Additional highlights include a 2-car garage, an already equipped laundry room, and a well-designed floor plan that offers both functionality and comfort. Located in the desirable Lake Lucerne community, residents enjoy great amenities, including a clubhouse, swimming pools, playground, and sidewalks for walking. Conveniently situated near Lake Alfred Elementary School, Daniel Jenkins Academy, Haines City Senior High School, as well as shopping, restaurants, and major roads with easy access to US-27, making commuting to Winter Haven, Davenport, and Orlando attractions even more convenient. Investor alert: The property is currently tenant-occupied with a lease in place through November 2026, generating $1,950/month in rental income. After the lease term ends, the new owner may choose to renew the lease or have the tenant vacate. Don’t miss this incredible opportunity!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Anderson Siqueira, Sr (407-912-4688)

Remarks: Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot on the 13th green. This charming 2-bedroom, 2-bathroom residence features a bright and open layout with a large living area plus an additional family room accented by a cozy brick fireplace and floor-to-ceiling wood built-ins. The brand-new kitchen has been thoughtfully updated with stainless steel appliances, quartz countertops, and all new cabinetry, along with a convenient passthrough window to the large glass-enclosed sunroom with A/C, making entertaining effortless while enjoying the view. The interior also features crown molding, new luxury vinyl plank flooring throughout the living areas, and new carpet in the bedrooms. Both bathrooms have been fully updated and include dual sink his-and-her vanities. Additional highlights include a new roof, a formal dining space, a side-entry two-car garage, fresh front landscaping, and a welcoming covered front porch, all combining to create a move-in-ready home in a desirable golf community setting. Cypresswood Golf & Country Club is a gated community with a 24 hour guard that hosts social and recreational events and features an 18-hole championship golf course designed by award-winning designer Ron Garl. In addition to golf, the facilities include a pro shop, wellness center, lounge, dining rooms, swimming pool, tennis courts, and trails. They also offer excellent practice facilities, including a putting green, chipping green and driving range. Golf carts are allowed throughout the community.

Listing is courtesy of: PORCHLIGHT HOMES LLC (863-529-3369)

Listing Agent: Angie Reynolds (863-838-1090)

Remarks: Short Sale. Perfect starter home or investment property! Welcome to this 4-bedroom, 2-bathroom residence located in the desirable Orleans community. Built in 2023, this charming corner-lot home offers an open floor plan with a spacious living area, kitchen, and dinette—all featuring easy-to-maintain tile flooring. A sliding glass door leads to the covered lanai, perfect for relaxing or entertaining. The primary bedroom is privately situated at the back of the home and includes a large walk-in closet and an ensuite bathroom with dual vanities and a separate stand-alone shower. Toward the front of the home, you’ll find three additional bedrooms and a full guest bath, offering plenty of space for family or visitors. Additional highlights include a laundry closet with washer/dryer hookups, a two-car garage, and a spacious backyard thanks to the corner lot. With a low HOA and peace of mind from a newer roof, HVAC, and water heater, this home offers both comfort and value. Conveniently located less than a mile from Legoland Florida Resort, and close to shopping, dining, medical facilities, and hospitals—this property truly has it all.

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

Listing Agent: Veronica Figueroa (407-519-3980)

Remarks: BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Square, centrally located in Winter Haven, FL. Before entering this beautiful residence, you will notice the BRICK PAVERED driveway/walkway leading through the MATURE LANDSCAPE and CUSTOM LIGHTING to the front SCREENED LANAI. Walk right into this very OPEN FLOORPLAN with HIGH CEILINGS and SPLIT BEDROOM CONCEPT. The kitchen is a CHEF'S DREAM, featuring UPGRADED STAINLESS APPLIANCES, IMPRESSIVE WINE FRIG., and BREAKFAST BAR. The CASCADING WATERFALL EDGE QUARTZ COUNTERTOPS add a MODERN, ELEGANT and LUXURIOUS focal point to this AMAZING KITCHEN!!! The adjoining great room is very spacious and overlooks the rear SCREENED LANAI with a view of the pond. The primary en-suite will not disappoint which also features QUARTZ COUNTERTOPS and an UPGRADED WALK-IN SHOWER with GLASS DOOR. CUSTOM PLANTATION SHUTTERS in the kitchen and bedrooms ensure you have the privacy you deserve! Don't forget about the second bathroom that has also been UPGRADED with QUARTZ COUNTERTOPS as well. This residence is truly TURN-KEY and one of the most WELL KEPT, ONE-OWNER homes you'll find anywhere. The reasonable monthly HOA dues include: ROOF REPLACEMENT, EXTERIOR PAINTING, YARD MAINTENANCE, LAWN IRRIGATION, and INTERNET/TV PACKAGE! Enjoy the other amenities including, but not limited to: pool/hot tub, tennis/pickle ball, gym, craft room, billiard room, movie room, and large meeting room with remodeled kitchen area. This wonderful property is in close proximity to medical, restaurants, shopping, worship, and LEGOLAND, FL. Winter Haven is well-known for it's beautifully interconnected lakes and being centrally located between the Tampa International and Orlando International Airports.

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

Listing Agent: Bryan Dicks (863-287-7851)

Remarks: PRE-FORECLOSURE - 3 Bedroom/2 Bath Home in a gated community. This home is only 4 years old, but it needs a lot of cosmetic work. The Buyers may assume the current mortgage at 3% interest.

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

Listing Agent: Linda Andre (863-294-7541)

Remarks: Under contract-accepting backup offers. BEAUTIFUL 3-BEDROOM POOL HOME ~ This inviting residence offers the perfect blend of comfort and functionality, featuring a spacious living room ideal for relaxing or entertaining, expansive kitchen, along with a desirable layout for added privacy. The home includes 3 bedrooms and 2 bathrooms, with a unique primary suite setup that features a private sink area separate from the bathroom for added convenience. Step outside to enjoy a screened-in lanai with a 10,000-gallon in-ground pool, perfect for soaking up the Florida lifestyle year-round. The patio provides additional outdoor space for dining or lounging, while the fully fenced backyard showcases mature landscaping for both beauty and privacy, along with a handy storage shed. This well-maintained property is move-in ready and offers everything you need to enjoy indoor-outdoor living at its finest—schedule your showing today!

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

Listing Agent: Erin Floyd (863-412-2286)

Remarks: Welcome to this Charming and newly remodeled home, located in the heart of Winter Haven! This inviting property offers comfortable living with a functional layout, perfect for both relaxing and entertaining. Whether you’re a first-time homebuyer, downsizing, or looking for an investment opportunity, this home is a must-see!

Listing is courtesy of: TCA REALTY, LLC (407-507-3982)

Listing Agent: Deidre Rios (407-433-6238)

Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, the Indigo brings all the things that matter together. The downstairs guest suite and bathroom are tucked away for added seclusion, while the open concept living space is perfect for entertaining. Upstairs, you'll find a generously sized recreation space, ideal for family time or unwinding. The owner's suite is a true sanctuary, featuring a walk-in shower, double vanities, and a spacious walk-in closet. A laundry room with a new washer and dryer is just off the owner’s suite, conveniently located near the 3 additional bedrooms and full bathroom. The Indigo is as functional as it is stylish, providing the perfect balance of comfort and modern living. 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 Construction. 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! 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: An inviting covered entry welcomes guests to this inspired Tarragon home. Pass two bedrooms, a shared bath, a flex room and a laundry on your way to a spacious great room with an adjacent covered patio. The well-appointed kitchen boasts a center island, a walk-in pantry and a dining nook. Showcasing a generous walk-in closet and an attached bath with double sinks. An additional bedroom and bathroom round out this inspired plan. *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)