Homes for Sale Near Winter Haven Senior in Winter Haven - 121 homes

Remarks: PRICE REDUCED on this wonderful opportunity! Welcome to Winter Ridge Condominiums — Lakeside Living on the Winter Haven Chain of Lakes. Discover the charm of Winter Ridge, a desirable waterfront condominium community offering direct access to Lake Smart, part of the renowned Winter Haven Chain of Lakes. This inviting 2-bedroom, 2-bath home features an open floor plan with ceramic tile throughout, a galley-style kitchen equipped with a refrigerator, range, microwave, and dishwasher, plus a walk-in pantry/utility room with in-unit laundry hookups. Relax and unwind on the oversized screened lanai while taking in peaceful views of Lake Conine, perfect for morning coffee or evening unwinding. The home also includes two assigned parking spaces directly in front of the unit, with additional guest parking conveniently located near the clubhouse. Community amenities include a heated swimming pool, clubhouse, shuffleboard courts, and a fishing and boat dock—perfect for enjoying the waterfront lifestyle. The HOA takes care of exterior maintenance, roof upkeep, lawn care, common area landscaping, road maintenance, and pool and dock care, offering truly low-maintenance living. Outdoor enthusiasts will appreciate the public boat ramp across the street providing access to Lake Conine, and the nearby Lake Conine Nature Park (just 0.5 miles away), featuring walking trails, picnic areas, and scenic lake views. Centrally located near shopping, dining, and medical facilities, this property is also just minutes from Legoland and Highway 27, with easy access to Tampa and Orlando. Enjoy comfort, convenience, and lakeside living in one of Winter Haven’s most sought-after condo communities—Winter Ridge.

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

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

Remarks: Under contract-accepting backup offers. Step into a home where every space invites you to stay and every corner is designed to create beautiful memories. This stunning, well-cared-for 4-bedroom, 2-bath single-family home is located in a quiet and peaceful area of Winter Haven, Florida, offering the perfect balance of comfort, warmth, and everyday tranquility. From the very first moment, this home welcomes you with an open, light-filled layout that brings the living and dining areas together—ideal for laughter-filled gatherings, special celebrations, and cozy nights at home. This is where life happens. At the heart of the home, the modern kitchen stands out with a spacious center island and drop-in sink, creating the perfect setting to cook, connect, and share unforgettable moments with family and friends. Just beyond, the screened porch becomes your personal retreat—perfect for morning coffee, evening conversations, or simply unwinding as the day fades away. The primary suite is a true private escape, offering space, comfort, and serenity. Enjoy an elegant ensuite bathroom with an oversized shower and a generous walk-in closet designed to make daily living effortless and enjoyable. Thoughtfully designed extras—including an indoor laundry room, a two-car garage, and a 6-speaker sound system throughout the home—add comfort, convenience, and the perfect atmosphere for every occasion. Located less than 13 minutes from downtown Winter Haven, you’re close to everything you need—shopping, dining, schools, and services—while still enjoying the peace of a calm, welcoming neighborhood.

Listing is courtesy of: PRESTIGE LEGACY REALTY (407-760-1521)

Listing Agent: Gil Medina (407-760-1521)

Remarks: This 3-bedroom, 2-bathroom home located in the Florida Highland Co neighborhood. This residence offers a classic and straightforward layout that provides a comfortable living environment for a variety of lifestyles. The heart of the home features a kitchen equipped with a mix of black and white appliances, complemented by durable laminate countertops that offer plenty of workspace for daily meal preparation. The interior transitions smoothly between living areas, maintaining a functional sense of space throughout. Situated in a convenient location, this property offers easy access to local amenities and major regional hubs, ensuring a simplified commute for those working in the surrounding areas. Schedule your private showing today!

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

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

Remarks: One or more photo(s) has been virtually staged. Downtown Winter Haven condo located in one of Winter Haven’s most iconic hotels, The Haven. This residence has been transformed into boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. With its blend of vintage charm, modern updates, and low-maintenance living, this 1-bedroom, 1-bath unit is ideal for first-time buyers, investors, seasonal residents, or anyone seeking an affordable condo with great rental potential. Located on the 3rd floor, the residence features tall ceilings, large windows, and bright natural light with elevated views of downtown. The updated kitchen offers granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets—perfect for maximizing storage in a condo setting. The spacious primary bedroom boasts oversized historic windows, a walk-in closet, and room for a king-sized bed. The bathroom has been refreshed with granite counters, a tiled tub surround, and a traditional tub/shower combo. The Haven provides sought-after condo amenities, including secure key-fob access, elevators, a community pool, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby. Residents also enjoy a private pool courtyard surrounded by lush landscaping, creeping fig walls, palm trees, and peaceful lounging areas—ideal for relaxation or working remotely outdoors. This walkable location offers the best of downtown Winter Haven living. Enjoy immediate access to dining, shopping, entertainment, and lakefront walking paths. With 50 lakes—including the world-famous Winter Haven Chain of Lakes—you’re minutes from boating, fishing, skiing, and sunset views. Everyday conveniences like Publix, Walmart, Aldi, TJ Maxx, medical facilities, and LEGOLAND Florida Resort are all close by. If you’re looking for an affordable, updated, low-maintenance condo with historic character and the convenience of downtown living, this stylish unit at The Haven checks every box.

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. One or more photo(s) has been virtually staged. Experience refined living in this beautifully renovated residence designed for both elegance and comfort. This exceptional 4-bedroom, 3-bath home has a newer roof and AC as well as featuring a desirable split floor plan, soaring ceilings in select areas, and an abundance of natural light that enhances the home’s open, airy feel. The designer kitchen is a true showpiece, appointed with all-new custom cabinetry, sleek quartz countertops, premium appliances, and an expansive peninsula ideal for upscale entertaining and casual dining alike. Luxury vinyl flooring flows seamlessly throughout, complemented by new designer fans, fixtures, and finishes. The primary suite serves as a private retreat, offering a spacious walk-in closet and a spa-inspired en-suite bath with double vanities and an oversized walk-in shower. A second en-suite bedroom provides the perfect guest or multi-generational suite, thoughtfully positioned for privacy. Step outside through two sets of sliding glass doors to your own resort-style oasis. The covered lanai overlooks a private, fully screened swimming pool with an in-ground spa, creating the ultimate setting for relaxation and outdoor entertaining. The fully fenced backyard enhances privacy while maintaining a serene atmosphere. Additional highlights include an indoor laundry room, an attached two-car garage, and an oversized driveway providing ample parking. This move-in-ready home offers sophisticated finishes, functional design, and luxurious indoor-outdoor living.

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

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

Remarks: PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Step inside and be greeted by a bright and open first floor layout designed for effortless living and entertaining. The spacious great room flows seamlessly into the stunning kitchen, featuring QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, A LARGE CENTER ISLAND, SPACIOUS PANTRY, and ABUNDANT CABINET SPACE. The adjacent dining area makes gathering and conversation feel natural and inviting. A HALF BATH and INSIDE LAUNDRY ROOM add everyday convenience. Upstairs, a VERSATILE LOFT offers the perfect second living space ideal as a TV lounge, playroom, homework hub, or home office. Tucked away in its own private corner is the PRIMARY BEDROOM, complete with an oversized WALK-IN CLOSET and spa-inspired en-suite bathroom with DUAL SINKS, QUARTZ VANITY, and an elegant WALK-IN TILE SHOWER. FOUR SPACIOUS SECONDARY BEDROOMS are thoughtfully arranged around a full bathroom with dual sinks, making room for everyone. Step outside to your FENCED BACKYARD, where a patio awaits—perfect for grilling, lounging, and enjoying Florida’s year-round sunshine. Enjoy low utility costs with your energy-efficient SOLAR PANELS leased at only $93/month. Home is located just off Dundee Road and gives you quick access to Hwy 27, Hwy 17 and Polk Parkway, theme parks like Legoland, Disney and Universal. Close to Winter Haven downtown, hospitals, restaurants, breweries, Chain of lakes and Florida beaches. With contemporary design, energy savings, and an unbeatable location, this home checks every box. Don’t miss your chance to make 271 Inman Blvd your New Haven—schedule your private showing today!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (352-688-2227)

Listing Agent: Isabelle Maye (540-840-8849)

Remarks: One or more photo(s) has been virtually staged. Hillcrest 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 1,758 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: Welcome to this charming and versatile 2-bedroom, 2-bath home offering 1,706 square feet of living space in Winter Haven. This property features a spacious combined living and dining area, ideal for both everyday living and entertaining. The home also offers a flexible bonus room that can easily be converted into a third bedroom, home office, hobby space, or guest area, along with a bright sunroom at the back—ideal for relaxing and enjoying backyard views year-round. Step outside to a screened-in back porch, ideal for unwinding or outdoor dining, and take advantage of the backyard shed for additional storage. With its adaptable spaces and inviting indoor-outdoor features, this home is a must-see—schedule your private showing today and discover all it has to offer! The home is being Sold in As Is condition without any Warranty nor Guarantee by seller. The buyer is responsible for verifying ALL property information, room sizes, utilities and condition. All buyers must view the home before submitting an offer. HUD CASE: 098-116683 FINANCE ESCROW MAY APPLY FINANCE CODE: IE

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

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

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: 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: FOR SALE-2 Bedroom/1 Bathroom Single Family Home with a 1l/4 of an acre of land. This is a cute home that has had some remodeling done. It's close to the Polk Parkway to the West and close to Highway 27 to the East not to mention that it's only minutes from Bartow which is the County Seat. Come take a look at this cozy home!

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

Listing Agent: Linda Andre (863-852-5747)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Short Sale. Short Sale opportunity on a 2023-built 3BR/2BA home offering modern design, open living space, indoor laundry, and a 2-car garage. A rare chance to own newer construction at an affordable price point. Ideal for first-time buyers or investors seeking strong long-term potential. Conveniently located near shopping, dining, and major roadways. Lender approval required.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Wanda Turner (407-756-2194)

Remarks: *** Motivated seller! Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! *** Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.

Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)

Listing Agent: Brian Surrency (863-204-4298)

Remarks: Under contract-accepting backup offers. Welcome to 1622 Klatt St SE in Winter Haven, a unique opportunity offering business residential zoning ideal for homeowners, investors, or small business use. This property provides flexibility for residential living, home office, rental income, or professional services in a growing and centrally located area. Situated on high and dry land, this property offers added peace of mind with no flood concerns. The lot and location make it well-suited for long-term ownership, redevelopment, or income-producing potential. Conveniently located near major roadways, shopping, dining, and local amenities, this property benefits from strong accessibility and visibility while still maintaining a residential feel. The surrounding area continues to see growth, making this an attractive option for buyers looking to secure property in a developing corridor. This property is priced appropriately for today’s market, creating an excellent opportunity for buyers seeking value, flexibility, and location in Winter Haven.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Michael Hochadel (863-604-0018)

Remarks: One or more photo(s) has been virtually staged. This beautifully maintained 2-bedroom, 2-bath home with a 2-car garage offers the perfect blend of comfort, smart updates, and lifestyle perks. There’s something about 4454 Glenns Landing that feels like home before you even step inside. Maybe it’s the quiet charm of the neighborhood — families out walking at sunset, riding bikes, neighbors waving as they pass. Maybe it’s knowing you’re not just buying a house…you’re stepping into a true community. Inside, enjoy the natural light through new windows installed in 2021 and the roof was also replaced in 2020, giving you peace of mind and eliminating two major expenses right from the start. The kitchen has a quaint eat-in area as well as great counter space for food prep and stainless steel appliances. The seamless flow between the living room and dining area creates a spacious feel while keeping everything connected — perfect for entertaining guests, hosting family dinners, or simply enjoying a cozy night at home. The primary suite is a relaxing retreat, featuring a spacious walk-in closet and a private bath with solid surface countertops that add both durability and elegance. The secondary bathroom also showcases matching solid surface countertops, creating a cohesive and polished feel throughout. One of the home’s best surprises, the fully enclosed porch with its own air vent, seamlessly adding extra square footage of living space. Whether you envision a sunroom, home office, reading nook, or second living area, this flexible space gives you room to live the way you want. Step outside your front door and enjoy a neighborhood designed for connection. Residents enjoy access to: a clubhouse with a sparkling pool, a fishing pier and dock, boat slips available on a first-come, first-serve basis, a vibrant social club that plans activities year-round.

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

Listing Agent: Tisha Talbot (863-236-7610)

Remarks: Check out this upgraded Columbus on a corner lot! This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, which has upgraded contertops, dining room and family room, with a patio extending the interior space outdoors, patio has also been upgraded with a 12x8 concrete flooring perfect for a lania or sunroom. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite with upgraded master bath and closet. Completing the home is a convenient two-car garage. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

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

Listing Agent: Garrett Collins (623-466-3925)

Remarks: Short Sale. We are in the process of getting a short sale approved. So expect delays. Welcome to 29 Golfview Circle NE, a beautifully modernized Winter Haven property offering a rare combination of charm, flexibility, and income-producing potential. The main residence features 3 bedrooms and 2 baths with an open, inviting layout that includes spacious living and dining areas, stainless steel appliances, and a comfortable primary suite with a walk-in closet. Enjoy outdoor living from the covered front porch, the screened back patio, and the fully fenced yard. Additional updates— including a 2021 roof and numerous interior improvements—add peace of mind and long-term value. What truly sets this property apart is the detached 1BR/1BA guest house, completed in 2022 and designed as an ideal in-law suite or rental unit. This private space features polished concrete floors, a sleek updated kitchen, a modern bathroom with a large walk-in shower, an oversized closet with washer/dryer hookups, stainless steel appliances, its own fenced yard, and dedicated parking. Together, both structures offer approximately 2,228 sq. ft. of combined living space and 2,573 sq. ft. total under roof. Located on a corner lot directly across from Polk State College, this home delivers outstanding convenience with exceptional versatility—perfect for multigenerational living, additional income, or both. Opportunities like this are hard to find. Come see everything this remarkable property has to offer!

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

Listing Agent: Chris Sakamoto (904-200-7535)

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: 2021 built beautiful house with 4 beds and 2 baths and inside laundry room and double car garage totaling 2395 Sqft under roof. Centrally located in a very nice, quiet community on a dead-end road. Plenty of open air as there is no neighboring house on one side and back of the house. Open floor plan with Master in one side and other three bedrooms are located on the other side of the house. Stainless appliances are in the kitchen with a large spacious island for meal preparation and breakfast. Master bath with his and her walk-in closet with separate door for the toilet. Double sink and standing shower in the master and tub in the other bath. Tiles in all wet areas and waterproof wood like vinyl flooring throughout the living area and bedrooms floor. Dishwasher (not included with this sale) has power but not hooked up with water (buyer will have to try as is or get their own dishwasher). House is AS IS and buyer to verify as seller never lived on this property.

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

Listing Agent: Mohammad Iqbal (813-494-8864)

Remarks: WELCOME HOME TO THIS MOVE IN READY LAKEFRONT CONDO. 2BEDROOM - 2 BATH WITH 1252 SQ FT OF LIVING AREA , PLUS A FLORIDA ROOM OVERLOOKING LAKE BUCKEYE. THIS CONDO UNIT HAS STORAGE THROUGHOUT, GREAT STORAGE CLOSET OFF THE FLORIDA ROOM, ALSO INSIDE UTILITY WITH WASHER/DRYER HOOKUPS AND THE PRIMARY BEDROOM HAS A WALK IN CLOSET. YOU HAVE THE PRIVACY OF THIS UPSTAIRS UNIT WITH A BEAUTIFUL VIEW, NEW CARPET & INTERIOR PAINT,. IT ALSO FEATURES CONVENIENT COVERED PARKING AND COMMUNITY POOL & TENNIS. LOCATED NEAR POLK STATE COLLEGE , YOU CAN ENJOY A WALK AROUND NEARBY LAKE ELBERT OR DRIVE JUST MINUTES TO DOWNTOWN WINTER HAVEN FOR SHOPPING, RESTAURANTS AND COMMUNITY EVENTS. DON'T MISS OUT ON THIS LAKEFRONT VIEW OF LAKE BUCKEYE .

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)