Homes for Sale Near Winter Haven Senior in Winter Haven - 175 homes

Remarks: Under contract-accepting backup offers. Welcome to this charming 2-bedroom, 1-bathroom home in the West Cannon Heights neighborhood of Winter Haven, an excellent opportunity for first-time buyers or investors. With a really large open kitchen, this home is move-in ready. The exterior features a covered parking area and a workshop with a new roof. This property offers a cozy living space and a convenient location, with no HOA fees. Don't miss the chance to own this piece of Winter Haven.

Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)

Listing Agent: Pablo Lluveras Matos (813-406-3652)

Remarks: Short Sale. APPROVED SHORT SALE AT PRICE! CHAPTER 7 BANKRUPTCY - Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional Kitchen Overlooking The Main Living Space. Fenced Yard. Ideal For Everyday Living And Entertaining. Built In 2019, Conveniently Located Near Shopping, Dining, Schools, And Major Roadways With Easy Access Throughout Winter Haven. Bankruptcy Short Sale — Third-Party Approval Required. Property Sold As-Is. Great Opportunity For Owner-Occupants Or Investors Seeking Value In A Growing Area. Call Today For Details Or To Schedule A Private Showing.

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

Listing Agent: Jon Mccall, Pa (352-725-7206)

Remarks: Under Construction. This two-story home features 4 bedrooms and 2 and a half baths. This Home begins with a two-story foyer opening up to the spacious first floor living spaces. The kitchen shines with abundant counter space and an island perfect for entertaining, Upstairs, you will find all four bedrooms and the designated laundry room. CUSTOM EXTERIOR includes 30-year mildew resistant dimensional shingles Cementitious masonry finish walls & gables, Termite treated with Bora care-renewable after 1st year Designer paint schemes Two convenient garden hose bibs, Dead bolt locks on all exterior doors, Low maintenance aluminum fascia and vinyl soffit Professionally landscaped yards, two exterior weatherproof electrical outlets, Insulated, fiberglass front & rear doors, Decorative coach lights on garage and front entry. EXCEPTIONAL INTERIOR includes Stain resistant designer carpet, Recessed LED lighting in kitchen & family room, Level 1 tile standard in kitchen, laundry, foyer, and bathrooms Prewire for ceiling fan and 4 LED discs in family room, Pre-wiring for ceiling fans in all bedrooms with dual switches LED Disc, with rocker switches in all bedrooms, Doorbell chimes and protective smoke detectors Knock down texture on all interior walls and ceiling, Generous walk in closets with ventilated shelving,6 TV/Cable jacks or phone jacks, Vaulted ceilings, Wood Window Sills Brushed nickel hinges, fixtures and door knobs Indoor laundry room, Upgraded 5 1/4 baseboards throughout,5 panel smooth finish interior doors with brushed nickel, lever door handles, Garage door opener prewire, Two tone Interior paint package 220-volt dryer outlet Custom cased openings, GOURMET KITCHEN includes Designer recessed lighting Custom wood cabinets with adjustable shelves Included 36” upper cabinets with crown molding and custom bump out Stainless steel double bowl sink. Single lever brushed nickel faucet with pull out sprayer, Energy efficient multi-cycle dishwasher, Smooth top stove with self-cleaning feature, Space saver microwave above the range, Ice maker connection Spacious pantry with ventilated shelving. LUXURY BATH AREA includes Easy care garden tub/shower combination in master bath, Elongated toilets, Pull out drawers in most cabinets, Dual rectangle sinks, Upgraded brushed nickel faucets ENERGY EFFICIENCY includes Double pane insulated windows with tilt-in sash for easy cleaning, Energy efficient Whirlpool appliance package,R-38 ceiling insulation, Continuous soffit attic ventilation, Off ridge roof ventilation,15 SEER Heat Pump with digital thermostat Low volume flush toilets CONSTRUCTION QUALITY includes Interior wood studs 16” on center, Professionally engineered roof truss system, Fiber reinforced concrete slabs with vapor barrier 200 AMP service, Engineered to meet or exceed all wind codes 50-gallon water heater, Finished garage interiors Concrete, block construction ,Tax built-in pest control system(tubes in wall) This community is only a short, 10-minute drive to downtown and less than 5 minutes to shopping, schools, and more! Winter Haven is perfectly situated in the middle of Tampa and Orlando, each of which is only an hour's drive away. Villa Mar is perfect for those seeking vacation amenities alongside neighborhood conveniences. Winter Haven is home to Legoland Florida, Willowbrook Golf Course, and Auburndale Speedway. Within Villa Mar itself, there will be many amenities to suit whatever stage of life your family is in.

Listing is courtesy of: ADAMS HOMES REALTY (863-619-8120)

Listing Agent: Claudia Gutierrez Alvarez (602-800-4341)

Remarks: Welcome to your private retreat in the heart of Winter Haven - a beautifully updated 4-bedroom home with a new 2025 roof, solar panels, and a sparking pool on a quiet cul-de-sac with no HOA. Sitting on a generous 0.32-acre lot, this property delivers the space, privacy, and lifestyle buyers are searching for. The main floor features modern updates, an open layout, and a brand-new sliding door (2024) leading to the backyard oasis. Step outside to a large deck overlooking the pool, perfect for entertaining, relaxing, or enjoying Florida evenings. The fully fenced yard includes a farm style barn offering incredible storage, workshop potential, or hobby space. Major improvements have already been completed for you, including foundation work (2024), ensuring long-term stability and peace of mind. This move in ready, feature packed and priced to sell, this is the one you've been waiting for. Property is being sold As-Is.

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

Listing Agent: Daisy Perez (407-951-4218)

Remarks: The seller is OFFERING UP TO $14,000 toward a NEW ROOF or may apply this contribution toward the BUYER'S CLOSING COSTS, providing added flexibility and value. This spacious 4-bedroom, 3-bath ranch-style home offers an impressive amount of living space (2,178 sqft) filled with natural light and designed for comfort and flexibility. The many windows throughout the home create a bright, welcoming atmosphere, while multiple living areas provide room to spread out and enjoy. The remodeled kitchen features a refrigerator, dishwasher, and range, along with a convenient breakfast bar and adjacent dining area—perfect for everyday living and entertaining. A formal living room greets you at the front entry, and the oversized family room offers exceptional gathering space, complete with a built-in desk and direct access to the screened lanai. The generous primary suite includes a walk-in closet, garden tub, separate shower, and an additional wall A/C unit for added comfort. A desirable mini–master suite with its own private bath provides ideal space for guests, extended family, or a private home office. Built-in cabinetry throughout the home adds both character and abundant storage. Situated on a large corner lot, the expansive yard offers endless possibilities for outdoor living, recreation, or future enhancements. The chain-link fenced backyard provides security and functionality while maintaining an open feel. With no HOA restrictions, you’ll enjoy the freedom to personalize the property to suit your needs. Combining space, natural light, a sizable yard, and the advantage of no HOA, this property delivers comfort, flexibility, and room to grow.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Michelle Heath (863-528-3123)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home built in 2021, offering 1,832 sq ft of comfortable living space in the growing area of Winter Haven.This well-kept residence features a functional and open layout with a spacious kitchen that flows seamlessly into the living and dining areas—perfect for both everyday living and entertaining. Oneof the bedrooms offers flexibility and can easily be used as a home office, ideal for today’s lifestyle needs.The home also includes a dedicated laundry room and generously sized primary bedroom, providing comfortand convenience throughout. Located in a rapidly developing area, a new plaza is currently under construction nearby, adding future value and accessibility to shopping and dining options. Plus, LEGOLAND Florida Resort is approximately 20 minutes away, offering fun and entertainment close to home. Don’t miss the chance to own a newer home in a thriving community!

Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)

Listing Agent: Patricia Schraiber (407-413-1801)

Remarks: Built in 2023, this 4-bedroom, 2-bath Winter Haven home combines modern design with ultimate convenience. The bright, open-concept interior features ceramic tile floors and a chef-inspired kitchen with a large island. Relax on your screened-in lanai overlooking a private backyard. Located minutes from shopping, schools, and attractions—this move-in-ready gem is a must-see!

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

Listing Agent: Anthony Medina (863-242-9847)

Remarks: Beautiful single-family home offering 4 bedrooms and 2 bathrooms with approximately 2,012 square feet of heated living space. This spacious residence features high ceilings and a functional layout designed for comfortable living and entertaining. The kitchen includes space for a breakfast table and flows seamlessly into a separate dining room, while an additional family room provides the perfect setting for gatherings. Conveniently located near Cypresswood Golf & Country Club, East Central Park, and Rotary Park, offering access to outdoor recreation, including skating, softball, and picnic areas. The property also provides easy access to U.S. Highway 27, with shopping, dining, and everyday conveniences just minutes away, including Publix and Walmart. The owner is currently in the process of updating the home, including new flooring and additional improvements, all of which will be completed before closing.

Listing is courtesy of: REALTY OF AMERICA (321-732-5369)

Listing Agent: Cisco Romero (407-922-6375)

Remarks: Under contract-accepting backup offers. PRICE REDUCTION!! Welcome to the lakefront community of Edgewater Manor! Come see this awesome custom built 2017 4 bed 3 bath corner lot (1/3 ac.) home with fenced backyard! Located just off Cypress Gardens Blvd., this bright, open floorplan includes combo living and dining area, an office, and a spacious kitchen with white wood cabinets and grey granite counter tops, stainless steel appliances, gas stove, and eat-in area. There is a large family room off the kitchen, crown molding throughout the home, vinyl fencing, and much more, including: gas tankless WH, vinyl planking floor everywhere but bedrooms, plantation shutters, double pane low E windows, a screened lanai. There is even a plug for an electric car built into garage wall, and a shallow well for lawn irrigation. Plus, close to Legoland, restaurants, shopping, and the chain of lakes. A great find!

Listing is courtesy of: STORMS REALTY (813-293-4652)

Listing Agent: Steve Storms (813-293-4652)

Remarks: Under contract-accepting backup offers. Welcome to this inviting 3 bedroom, 2 bath home in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious Florida Room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a decorative fireplace with built-in bookshelves, creating a warm and welcoming atmosphere. Enjoy a fully fenced backyard, offering privacy and plenty of space for outdoor living, gardening, or pets. Located in a sought-after area, this home combines comfort, character, and convenience—close to schools, shopping, dining, Legoland and all that Winter Haven has to offer. Don’t miss the opportunity to make this beautiful property your own—schedule your showing today!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Under contract-accepting backup offers. Welcome to 2813 Wingfoot Court — now one of the best values in Cypresswood Golf & Country Club! Perfectly positioned along the 8th fairway inside this guard-gated golf community, this beautifully maintained 2-bedroom, 2-bath villa offers peaceful views and effortless Florida living—now at an exceptional new price. Being sold fully furnished and truly turnkey, this home is ready for immediate enjoyment—just bring your suitcase. Inside, you’ll find a professionally designed interior with vaulted ceilings that create a bright, open feel throughout the main living spaces. The kitchen includes updated appliances, including a newer stove and microwave, while most windows have been upgraded for improved efficiency and style. A tankless hot water heater adds modern convenience and energy savings. The spacious primary suite features a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and easy access to a second full bath—perfect for hosting family and friends. One of the home’s standout features is the inviting Florida room, ideal for morning coffee or relaxing after a day on the course. Step outside to the stained and stamped patio overlooking the fairway, creating a perfect space for entertaining or unwinding. Major updates include a roof (2019) and A/C (2018), providing added peace of mind. Residents enjoy access to community amenities including a pool, tennis courts, clubhouse, and on-site restaurant—all just minutes from shopping, dining, and major roadways. Now aggressively priced—don’t miss this opportunity to own in Cypresswood at one of the most attractive price points in the community.

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

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

Remarks: MOTIVATED SELLERS...OPPORTUNITY KNOCKS ON THIS SPACIOUS & AFFORDABLE 3 Bedroom/2 Bath Home in the heart of SE Winter Haven located in Lake Daisy Estates is ready for you & your family!!! NO HOA or CDD in this established neighborhood that is within 3 miles of LEGOLAND and close to multiple restaurants, shopping, & parks. The natural light fills each room of the home. Open floor plan with split bedrooms. You'll love the large open backyard that is fully fenced. Newer roof (2023). Schedule a tour today!!!

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

Listing Agent: Cheryl Brewer (863-224-0045)

Remarks: This 3 YEAR YOUNG, 4 bedroom, 2 bath single-family home built by DR Horton offers 1,867 square feet of thoughtfully designed living space and a 2-car ATTACHED GARAGE with OPENER and NO SOLAR PANELS!! The open floorplan features a seamless kitchen, dining area, and family room combination, ideal for both everyday living and entertaining. The kitchen includes a CENTER ISLAND, GRANITE countertops, DOUBLE SINK, and a WALK-IN PANTRY and is ready for your personal touch with NEEDED APPLIANCES (except for the included dishwasher). Ceramic tile flooring runs throughout the main living areas, with carpet in the bedrooms. The PRIMARY BEDROOM boasts a WALK-IN CLOSET and a spacious EN-SUITE BATHROOM featuring a walk-in SHOWER, DUAL SINKS with GRANITE countertops, and a PRIVATE WATER CLOSET. Three additional bedrooms are serviced by BATHROOM #2, which offers a TUB/SHOWER combination, SINGLE SINK VANITY, and GRANITE countertop. An INSIDE LAUNDRY ROOM with washer/dryer HOOK-UPS adds convenience. Additional features include an IRRIGATION SYSTEM and a COVERED concrete LANAI, accessed through sliding glass doors from the family room. This home combines modern design, functionality, and value in a well-built, nearly new property. NOTE: THIS PROPERTY IS NOT FOR RENT!!! DON'T BE SCAMMED BY SOMEONE ADVERTISING THE PROPERTY FOR RENT ON SOCIAL MEDIA!!

Listing is courtesy of: VIEWPOINT VALUE REALTY (863-617-7015)

Listing Agent: Pat Pearson (908-295-7970)

Remarks: Welcome to your Florida escape in the heart of Winter Haven! This beautifully maintained home in the sought-after Grey Heron community offers the perfect blend of comfort, space, and convenience with serene water frontage that creates the ideal backyard retreat. From the moment you arrive, you’ll love the inviting curb appeal, open-concept layout, and natural light that fills every room. Enjoy peaceful water views while relaxing, entertaining, or unwinding after a long day. Whether you’re hosting gatherings, working from home, or simply enjoying quiet evenings, this home was designed for everyday living and unforgettable moments. Conveniently located near shopping, dining, major highways, and Central Florida attractions, this is more than just a house — it’s the lifestyle buyers have been waiting for. Don’t miss the opportunity to make this exceptional waterfront property your next home!

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

Listing Agent: Amalia Lucena (904-614-1930)

Remarks: ANOTHER PRICE REDUCTION! OWNER IS VERY MOTIVATED! Welcome to 6107 Grand Oaks Drive on one of the most beautiful locations in Garden Grove Oaks, an active 55+ community where you own the land! NO LOT RENT HERE! This home has a beautiful extra lot included on the left side of the house for total privacy to the west, as well as there is vacant land behind the house. This extra lot is worth at least $21,000 according to the tax appraiser. That makes the house asking price only $163,900!! The yards on both lots are beautifully landscaped. This home has everything a homeowner could want: 2 bedrooms, 2 bathrooms, a side air-conditioned enclosed porch and an air-conditioned workshop. Inside is a great kitchen with beautiful cabinets (3 with decorative glass doors) and countertops with ceramic tiled borders. There is a gas range for the chef in the family! There is also a gas water heater and clothes dryer as well as natural gas heating! Great energy efficiency! There is a nice closet pantry with hookups for the washer and dryer if you prefer them to be inside the house. New double paned windows installed in 2017 throughout the home that have a lifetime guarantee! Roof has a vinyl single ply roof over, installed in 2013. It has a lifetime warranty! Air conditioner was replaced in 2006. Master bedroom has a nice walk-in closet, 13' x 4'. Master bathroom has a walk-in shower and many nice cabinets for all your needs. Guest bath has a large linen closet and a tub/shower combination. Family room is very large and opens through French doors to a Florida room that could be used for an extra sleeping area. All window treatments stay with the home as well as some of the furniture. Garden Grove Oaks is in a great area of Winter Haven, home to two Chain of Lakes for the boaters in your life. The lot to the left (west side) of the home is a part of this property. It can be your personal oasis for lovely evenings sitting outside under the Pergola! Buyer is able to sell the extra lot if desired. The Pergola has a clay wood-burning Chimenea and two gliders for relaxing outdoors. Electricity is available under the Pergola. A beautiful loquat tree graces the lawn on the extra lot. Much of the yard is shaded. There are many options for this extra property. Let your imagination be your guide! Furniture and items still in house and yard (fountain, etc.) are negotiable for new buyer. Garden Grove Oaks has a great clubhouse where many activities are available to residents. The clubhouse includes a billiards room, cards/game room, a large heated pool and spa, and a screen room with a grill and eating area. There are also shuffleboard courts and a small pond with a fountain. This location is only minutes away from Hwy. 27 and many restaurants, shopping and churches. The home has been well loved and the seller is looking for another great homeowner who will love the home as well. Please make your appointment to see this wonderful home today!

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

Listing Agent: Peggy Lewellen (863-412-7692)

Remarks: Under contract-accepting backup offers. 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)

Remarks: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. In addition to the home’s like-new condition and thoughtful upgrades, qualified buyers may also have the rare opportunity to assume the seller’s existing 5.125% mortgage — potentially creating estimated monthly savings of more than $250 compared to many current market interest rates. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.

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

Listing Agent: Chris Loschiavo (863-280-2201)

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

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

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

Remarks: Exquisitely and completely remodeled residence at 1539 Roselawn, thoughtfully designed to blend modern elegance with everyday comfort. This stunning home showcases high-end finishes throughout, including premium waterproof luxury vinyl flooring that adds both durability and sophistication. The gourmet-inspired kitchen is a true centerpiece, featuring sleek granite countertops, modern cabinetry, and stainless steel appliances that elevate the overall aesthetic and functionality of the space. The home also provides peace of mind with an AC system updated in 2018, ensuring efficient cooling and long-term reliability. Every detail has been carefully selected to create a cohesive and refined living environment. Situated with no HOA restrictions, this property offers exceptional flexibility and freedom, making it ideal for both homeowners and investors. Whether as a primary residence or an income-producing asset, this home represents a rare turnkey opportunity combining style, quality, and value in one package.

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

Listing Agent: Ines Morales (863-738-8794)

Remarks: Welcome to 652 Grove St. TWO living spaces for ONE price. This exceptional property in the heart of Winter Haven offers a spacious main home plus a fully independent Mother-in-Law Suite all under the same roof. The primary residence features 3 bedrooms, 2 bathrooms, a dedicated office/flex space, an open-concept layout filled with natural light, and a 2-car garage designed for comfortable everyday living. What truly makes this property stand out is the private annex/guest house, complete with its own separate entrance, 1 bedroom, 1 bathroom, semi-equipped kitchen, and private laundry area, creating the perfect setup for extended family, guests, multi-generational living, or a private retreat space. This rare “home within a home” offers flexibility, privacy, and functionality that is hard to find at this price point. Conveniently located near US-27, shopping, dining, and everyday essentials, this unique property is a must-see to truly appreciate its layout and possibilities. Schedule your private showing today.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Lizandra Troisi Passos (321-337-9448)