Homes for Sale Near Winter Haven Senior in Winter Haven - 155 homes

Remarks: Under contract-accepting backup offers. Welcome to 960 Wedgewood Dr SE, a one-owner, mid century ranch home offering over 2,300 square feet of living space with original vintage character, ideally situated on a spacious ¼+ acre cul-de-sac lot with no HOA. This 3-bedroom, 2-bath residence offers a functional and inviting layout with formal living and dining rooms, with the dining room offering flexibility as a potential 4th bedroom thanks to its walk-in closet. The large formal living room provides ample space to host many guests and creates the perfect setting for intimate gatherings and conversation while the comfortable family room features a brick wood-burning fireplace surrounded by built-in shelving and cabinetry, creating a warm and welcoming focal point. The kitchen is generously sized with wood cabinetry, abundant counter space, ample storage, and a closet pantry—ready to serve as the heart of the home. The primary suite includes an en-suite bath with an updated walk-in shower and a spacious walk-in closet. Two additional bedrooms provide plenty of space for family or guests. A secondary bath with a tub is conveniently located by the bedrooms and the hallway features two linen closets, offering great storage throughout the home. A front bonus room creates a welcoming entry and is perfect for a piano or flex space. Additional highlights include a screened rear lanai ideal for morning coffee or entertaining, a charming covered front porch, a fenced backyard, and a storage shed with built-in shelving. The home is equipped with two A/C units plus a mini-split in the primary bedroom, allowing you to keep the home extra cool during Florida’s summer months. The oversized two-car garage offers built-in shelving, a storage closet, washer and dryer, and attic access via pull-down stairs for additional storage. Additional features include rain gutters, a separate irrigation water meter, and a location on a dead-end road with minimal traffic, offering added privacy and quiet enjoyment. Major updates have already been completed, including a new electrical panel and breakers (2024), partial re-plumbing (2021), roof (2016) with 50-year shingles, A/C units (2015 & 2018), and a natural gas water heater (2016). With new flooring and cosmetic updates, this home offers the perfect opportunity to create a charming and beautiful space to enjoy for years to come. Conveniently located just minutes from Publix, restaurants, schools, medical facilities, and LEGOLAND Florida Resort, with easy access to both Tampa and Orlando, offering quick trips to world-class theme parks and Florida’s east and west coast beaches. Located on a highly sought-after street, this is a rare opportunity to purchase a well-built home with great bones, space, and location—ready for its next chapter.

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

Listing Agent: Deanna Stone (863-412-2080)

Remarks: SHORT SALE!! Welcome to Heather Glen, a gated community in the heart of Winter Haven with an HOA of ONLY $150 A YEAR! This charming 3 bedroom, 2 bathroom home with an attached 2-car garage offers comfort, security, and convenience & ready for a quick close & move in. Featuring neutral gray walls, wood-look tile flooring, and plantation shutters throughout, this open-concept home is filled with natural light and boasts a spacious master suite with walk-in closet and private bath, two additional bedrooms with a guest bath, and a bright kitchen with plenty of counter space, a window over the sink, and a cozy dinette area for your morning coffee. Enjoy the convenience of an interior laundry room, newer roof and A/C unit, and a fully fenced backyard with a separate well for irrigation. Located just minutes from Legoland, Peppa Pig Theme Park, shopping, dining, medical facilities, and downtown Winter Haven, this pristine home is the perfect rental in a sought-after location. Schedule your showing today!

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

Listing Agent: Jeavanna Lanza Pa (585-313-3408)

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: 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: Welcome to 22 Lake Link in Winter Haven, where space, lifestyle, and location come together in one exceptional opportunity. Situated on a large corner lot, this 4-bedroom, 2-bathroom home with a 2-car garage offers the perfect combination of comfort, functionality, and Florida living. Step inside to a bright and open floor plan designed for modern living and entertaining. The spacious layout flows seamlessly from the living and dining areas to the kitchen, creating the perfect environment for hosting family and friends. Enjoy your mornings on the front balcony and unwind in the evenings on the screened-in patio, overlooking your huge fenced-in backyard—ideal for pets, gatherings, or even adding a pool. Additional highlights include a durable metal roof for long-term value and a large driveway with plenty of space for multiple vehicles, guests, or recreational toys. This home is perfectly positioned to give you access to everything that makes Central Florida one of the most desirable places to live. Convenient access to major highways including Interstate 4, US Route 27, and Florida State Road 540 for easy commuting to Orlando, Tampa, and beyond. Just a short drive to world-famous attractions like Walt Disney World, Universal Orlando Resort, and LEGOLAND Florida Resort. Enjoy weekend trips to Florida’s beautiful beaches including Clearwater & St. Pete Beach (west coast) and Cocoa Beach (east coast). Living in Winter Haven means you’re close to a growing scene of local favorites and everyday conveniences such as, Coffee spots like Richard's Fine Coffees and Starbucks. Popular dining options including Harborside, Tanners Lakeside Restaurant & Bar, Aria and Azteca D'Oro. Shopping and entertainment nearby at Winter Haven Central Park and Eagle Ridge Mall. Minutes from Lake Link and the Chain of Lakes of Winter Haven, Florida.

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

Listing Agent: Omar Andreasen (407-883-2989)

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: 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: **Location, Location, Location! Seller offering $10,000 toward buyer closing costs, prepaid items, or interest rate buy-down with acceptable offer!** Beautifully maintained 3-bedroom, 2-bath home situated on an expansive oversized corner lot in desirable Southeast Winter Haven with **no city taxes — county taxes only**. Major updates have already been completed, including a **2024 A/C**, **2019 roof**, **new drain field**, and recent **septic inspection/pump-out** for added peace of mind. Inside, you'll find luxury laminate flooring throughout the main living areas with ceramic tile in wet areas, creating a clean and modern feel. Enjoy outdoor living in the private rear courtyard shaded by mature landscaping and beautiful trees, plus a stunning oak tree that enhances the curb appeal of this spacious corner homesite. A rare bonus is the **704 sq. ft. detached garage/workshop**, offering endless possibilities for storage, hobbies, vehicles, or workspace. Conveniently located near shopping, dining, schools, **only 2.1 miles from LEGOLAND Florida Resort**, close to Chain of Lakes access, near Freedom Boat Club, and just minutes from the new Chain of Lakes Baseball Complex. Don’t miss this opportunity!

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: John Calhoun (863-528-7973)

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 your turn-key Florida retreat! This beautifully reimagined home is a masterclass in modern updates and serene living, nestled within a tranquil, established community. From the moment you arrive, the vibrant curb appeal and crisp, clean lines signal a home that has been maintained with pride. The heart of the residence is an open, sun-drenched kitchen featuring premium stainless-steel appliances, sleek cabinetry, and chic subway tiling—perfect for the culinary enthusiast or the frequent entertainer. With durable wood-look flooring and a versatile, oversized utility suite, this home seamlessly blends style with everyday functionality. Beyond the interior, your private oasis awaits. Relax on the expansive screened-in porch or take advantage of the massive, fully fenced backyard—a rare find that offers limitless potential for a pool, garden, or workshop. The long driveway and integrated carport provide plenty of space for your vehicles and toys, making this the perfect home base for a Central Florida lifestyle. Whether you’re a first-time buyer or a savvy investor looking for a high-quality asset, this property offers an optimistic outlook and incredible value. Opportunity is knocking—book your showing today and claim your piece of paradise!

Listing is courtesy of: MCO REALTY (407-479-8601)

Listing Agent: Vernel Smith (863-224-1942)

Remarks: ***This home can be yours for 4.75% Interest rate on a assumable loan*** Located in the desirable Inman Grove solar community in Winter Haven, this 3 bedroom, 2 bathroom home with a fully fenced backyard offers the perfect combination of energy efficiency, modern design, and convenient Central Florida living. Built in 2023, NO CDD, LOW HOA of less than $45.00 a month, LOW ELECTRIC BILL MONTHLY..averaging $30-$83 a month ***=SAVINGS***, this newer construction home features solar power to help reduce monthly utility costs, making it an excellent option for buyers searching for energy-efficient homes in Polk County. ****Inside, the home offers a bright open floor plan with tile flooring throughout the main living areas and carpet in the bedrooms for added comfort. The kitchen overlooks the living and dining space and features quartz countertops, stainless steel appliances, modern cabinetry, and plenty of counter space, ideal for everyday living or entertaining guests. Natural light fills the main living area, creating a clean and inviting feel throughout the home. The split bedroom layout provides privacy, with the primary suite located toward the rear of the home and secondary bedrooms positioned near the front. The primary bedroom includes a private bathroom with updated finishes and generous closet space. Both bathrooms feature contemporary vanities and quartz countertops, giving the home a modern clean look buyers are searching for. Enjoy the outdoors in the fenced backyard, perfect for pets, gatherings, or relaxing evenings. The yard offers space to personalize while still being easy to maintain. Inman Grove is known for its solar-powered homes, newer construction, and peaceful residential setting, while still being close to everyday conveniences. The home is conveniently located near LEGOLAND, shopping centers, restaurants, schools, medical facilities, and major roadways, with easy access to Orlando, Lakeland, and Tampa. This property is ideal for buyers looking for.... New construction homes in Winter Haven, Solar homes in Florida, Move-in ready homes near Legoland, Fenced yard homes in Polk County Energy-efficient homes with low utility costs Schedule your showing today and see why so many buyers have chosen this Winter Haven community.

Listing is courtesy of: NORKIS & CO REALTY (407-506-7070)

Listing Agent: Jannese Garcia Vazquez Pa (407-921-4418)

Remarks: MOVE-IN READY! Step inside this stunning one-story Castaway home feel right at home. As you enter through the front door, a welcoming foyer sets the tone for the open and inviting layout. Two spacious bedrooms are tucked at the front of the home and share a beautifully designed full bathroom, perfect for family or guests. A third bedroom with its own private bath offers comfort and privacy, ideal for visitors or a home office setup. Continue down the hallway and the home opens up into a wide, light-filled living area where the kitchen, dining, and family room seamlessly connect. The kitchen features sleek gray cabinets, quartz countertops, and a large island that overlooks the gathering spaces, making it the heart of the home—perfect for cooking, dining, and entertaining all at once. At the back of the home, the private primary suite provides a peaceful retreat with a spacious bathroom featuring double vanities, a walk-in shower, and a generous walk-in closet. Step outside through the sliding doors to a covered lanai, where you can relax and enjoy Florida’s sunshine year-round. Situated on a desirable corner homesite in Willowbrook North, this beautifully designed home offers modern finishes, an open concept layout, and a lifestyle made for comfort and connection.

Listing is courtesy of: DRB GROUP REALTY, LLC (407-270-2747)

Listing Agent: Adam Schott (407-270-2747)

Remarks: Under contract-accepting backup offers. Beautifully maintained 4-bedroom, 2-bathroom home with a 2-car garage, situated on a spacious corner lot of over a quarter acre in desirable Winter Haven. The primary suite features an en suite bathroom with a walk-in shower, while three additional generously sized bedrooms and a second full bath provide comfortable accommodations for family or guests. The inviting kitchen offers ample space with a breakfast bar and adjacent dining area, perfect for everyday living and entertaining. An inside laundry room adds convenience. Enjoy outdoor living in the fully fenced backyard, complete with plenty of room to relax, play, or entertain, and a perfectly sized patio for gatherings. Ideally located close to shopping, dining, entertainment, medical facilities, and the world-famous Plant City Strawberry Festival

Listing is courtesy of: JT REALTY & ASSOCIATES (352-279-2640)

Listing Agent: Lindsey Funderburk (352-606-9639)

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

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

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

Remarks: Welcome to this charming two-story townhome located in the Casarena gated community in Winter Haven, offering 2 bedrooms and 2.1 bathrooms designed for comfort and flexibility. The inviting main living area features a cozy fireplace, perfect for relaxing or entertaining, while the functional layout flows seamlessly into the dining and kitchen spaces. Upstairs, enjoy your own private second-floor balcony—an ideal spot for morning coffee or unwinding in the evening. Enjoy family gatherings in the large screened in patio that is ready to be converted into your ideal outdoors living space. Additional highlights include a convenient laundry closet in the garage and ample storage throughout. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this home checks all the boxes—schedule your private showing today and make it yours! This home is being sold in As Is condition. All buyers must view the home before submitting an offer.

Listing is courtesy of: REALTYCITY INC (863-438-6605)

Listing Agent: Jesse Carriedo (863-438-6605)

Remarks: Move-in ready single-story home with NO HOA! This 3-bedroom, 2-bathroom gem features low-maintenance tile flooring throughout the entire home—no carpet here! The kitchen is stylishly appointed with stainless steel appliances and crisp painted cabinets. Enjoy outdoor privacy in the fully fenced backyard, perfect for relaxing or entertaining. Complete with a 1-car garage. A fantastic opportunity for easy living!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)