Homes for Sale Near Winter Haven Senior in Winter Haven - 143 homes

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)

Remarks: Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale, FULLY FURNISHED, and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, New Furniture, and the Interior was Freshly Painted. The owners are including the 75 Inch TV with the Entertainment Center in the Living Room. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy your favorite show on TV. The Home is located close to Shopping (New Publix opening soon), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!

Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)

Listing Agent: David Shippey (863-521-4517)

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: 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: **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: One or more photo(s) has been virtually staged. Short Sale. Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, offering 1,512 square feet of comfortable living space in a desirable gated community in Winter Haven. Built just two years ago, this nearly new home blends modern design with a warm, family-friendly feel. Step inside to find vaulted ceilings and tile flooring throughout the main living areas, creating a bright and open atmosphere. The spacious kitchen features stainless steel appliances, a large island, and ample cabinet space, perfect for everyday living or gathering with friends and family. The split floor plan provides privacy, while the generous primary suite includes double sinks, a garden tub, separate shower, and walk-in closet. Enjoy Florida living outdoors on the covered lanai, with a backyard perfect for relaxing afternoons or weekend playtime. Conveniently located near Downtown Winter Haven, Polk State College, Winter Haven Hospital, shopping, dining, and major attractions like LEGOLAND. For those who love lifestyle and entertainment, the home is also just about 15 minutes from the popular Port 27, a vibrant waterfront destination known for its live music, great food, desserts, and beautiful lake scenery—the perfect place to unwind and enjoy time with family and friends. This move-in ready home offers comfort, style, and location all in one. Schedule your showing today!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Carolina Flores, Llc (954-471-5909)

Remarks: Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage. Ready for your finishing touches!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: MOVE-IN READY! Beautiful 2 Level, Coastal elevation, 2 Car Garage Home with Open Concept Living and 3 Bedrooms! The inviting front porch opens to a gracious foyer that leads you to the open main living space. The family room is open to the dining area and adjacent kitchen. The primary suite boasts an ensuite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet. The second level offers a spacious loft and 2 secondary bedrooms each with walk-in closets and a full bathroom.

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

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

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: Motivated seller— presenting a great opportunity for new buyers! Enjoy true waterfront living with direct Chain of Lakes frontage on Lake Hartridge in this beautifully updated 3-bedroom, 2.5-bath townhome-style condo. Located in the highly desirable Casa Del Sol community in Winter Haven, this spacious two-story residence offers breathtaking panoramic lake views and direct water access. The interior features wood laminate and tile flooring, a formal dining room, and an updated kitchen complete with stainless steel appliances and solid surface countertops. The expansive living room overlooks the water, creating a perfect setting for both relaxing and entertaining. Unwind in the Florida room or take in stunning sunrise and sunset views from your screened lakefront lanai. Upstairs, the generous primary suite offers a walk-in closet, an ensuite bath with granite countertops, and a private enclosed balcony showcasing incredible lake views. Two additional bedrooms, a full bath, and an upstairs laundry area complete the second floor. An attached two-car garage adds everyday convenience. Residents of Casa Del Sol enjoy access to exceptional amenities, including a lakefront recreation area, pool, clubhouse, tennis courts, and a private dock. The HOA covers water, lawn care, and full use of community amenities, providing a truly maintenance-free lifestyle. Experience the best of waterfront living with endless opportunities for boating, fishing, and enjoying the beautiful Winter Haven Chain of Lakes.

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

Listing Agent: Irene Bryan (863-289-6789)

Remarks: Welcome home! Your forever home is located near downtown Winter Haven and just a short distance from Polk State College. Completely remodeled in 2021 with a New Roof, New A/C, New Water Heater, New Electrical system, new windows new kitchen (Quartz Countertops), new appliances, new floors (Vinyl). This home has a huge, oversized corner lot and with summer around the corner, this will be the place for all the summer BBQ's.

Listing is courtesy of: FLATFEE.COM (954-965-3990)

Listing Agent: Cliff Glansen

Remarks: ***SELLER INCENTIVE! Seller offering $3,000 credit to buyer that can be used toward closing costs or interest rate buy-down.*** Welcome home to this beautifully maintained 3-bedroom, 2-bath residence in the desirable Peace Creek Reserve community of Winter Haven! This inviting home features an open, split-bedroom floor plan with plenty of natural light and modern finishes throughout. The kitchen offers ample counter space, stainless steel appliances, and a breakfast bar that overlooks the spacious living and dining areas perfect for entertaining. The owner’s suite provides a peaceful retreat with a private bath and generous closet space. Step outside to enjoy your fully fenced backyard ideal for pets, play, and outdoor gatherings. Additional highlights include a two-car garage, covered entry, and a convenient location near shopping, dining, and top-rated schools. Don’t miss the chance to make this move-in ready gem your new home!

Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)

Listing Agent: Stephanie Florez (407-810-5874)

Remarks: This newer, well-maintained 3-bedroom, 2-bath manufactured home offers a practical layout with a split-bedroom design and open living, dining, and kitchen areas. The interior provides a functional flow that is perfect for easy living. Located on a fully fenced lot with no HOA, the property offers usable outdoor space and added flexibility. Additional features include a screen entry area, an indoor laundry area with a washer and dryer included, and a storage shed for extra space. Great investment opportunity.

Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)

Listing Agent: Chrissi Jasso (863-618-4000)

Remarks: Beautifully remodeled 4-bedroom, 1-bath home featuring an open floor plan, bright living spaces, and a modern kitchen with brand-new stainless steel appliances. Spacious bedrooms filled with natural light and a large backyard perfect for outdoor enjoyment. Conveniently located near parks, schools, and shopping. Schedule your showing today!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Jose Ferrer (787-238-6505)

Remarks: Already appraised for the listing price, this home is a great opportunity for massive savings every month on utility bills. Current owners typical electric bill in heat of summer is approx. $16 Solar panels WILL be PAID IN FULL by Sellers at closing. 4 BR/2.5 BA w/NEW ROOF 2025, NEW AC 2024. Durable porcelain wood plank-look floors throughout. Stone, wood burning fireplace in great room. Very private, screened 32 x 16 HEATED pool with large covered seating area, cabana bath, outdoor shower and and roomy storage. Well established, small gated community convenient to shopping, downtown WH, chain-of-lakes recreation. Easy going HOA. Pet friendly! Safe concrete block/stucco construction and NO CDD. Don't miss this opportunity to protect yourself from future electric rate hikes. It's move in ready!

Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)

Listing Agent: Julie Phillips (561-906-1118)

Remarks: Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quarz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and en-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!

Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)

Listing Agent: Martha Leighton, Pa (407-223-7767)

Remarks: Under contract-accepting backup offers. WELCOME TO THIS AMAZING POOL HOME SITUATED ON AN OVERSIZED (.43) ACRE LOT LOCATED IN HAMILTON POINTE, AN ESTALISHED LAKEFRONT COMMUNITY IN WINTER HAVEN, FL! As you enter, you will immediately notice the NATURAL LIGHT, HIGH CEILINGS, OPEN CONCEPT FLOORPLAN and BEAUTIFUL POOL VIEW. The spacious eat-in kitchen features lots of built-in cabinetry, granite countertops, stone backsplash, double ovens, island with cooktop, large double sink and another great view of the pool area! The primary en-suite has an oversized soaking tub for relaxing, double sinks, large walk-in-shower with built-in-seating, 2 huge walk-in closets with custom shelving, and plantation shutters. The 2 additional bedrooms are very spacious and feature built-in closet shelving. The second full bath has been tastefully updated with granite countertops, canned lighting and large walk-in shower with corner seating. The oversized and fully screened pool and patio area is perfect for all your entertaining! Thanks to the solar/electric heated pool, you will be able to enjoy swimming year-round. The 1/2 bath is conveniently located just in from the screened lanai, making it convenient for guests. Don't forget about the spacious 3 car (25 x 35) garage and circle drive for visitor parking. The inside laundry room has cabinetry for extra storage and also features a utility sink. Save $$ on your water bill with your very own irrigation well. A newer hot water heater installed (2024) will also add to the home's efficiency. Don't miss out on this meticulously maintained property centrally located between Tampa International and Orlando International Airport! The Country Club of Winter Haven, shopping, medical and LEGOLAND, FL are just minutes from this wonderful property that has been lovingly cared for.

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

Listing Agent: Wanda Dicks (863-287-7846)

Remarks: CORNER UNIT WITH VAULTED CEILINGS AND PRIVATE BALCONY- Welcome to your new retreat in the highly sought-after chain of lakes community of Park Lake — where comfort, style, and location come together beautifully. Step inside this charming one-bedroom, one-bath home and you’ll immediately notice the open feel created by vaulted ceilings and luxury vinyl flooring throughout the main living areas. The kitchen is a true highlight, featuring quartz countertops, sleek cabinets, stylish backsplash a modern tile floor, and all-new stainless steel appliances — including a five-burner stove, low-profile microwave, and refrigerator with exterior ice-maker. Thoughtful upgrades like new sinks, faucets, a garbage disposal, and modern lighting add both function and sophistication. The bathroom feels spa-like with a sleek tile shower, coordinating tile floor, quartz countertop, new sink, fixtures, and an elegant multi-illuminating with anti fog mirror that provides perfect lighting for any time of day. Two sliding glass doors — one from the living room and another from the bedroom — open to your private screened balcony, filling the home with natural light and offering peaceful outdoor views. The spacious bedroom includes a large closet, providing plenty of storage. This home also features a 2026 hot water heater, 2021 roof, and 2017 AC- offering peace of mind for years to come. Updated blinds, modern ceiling fans, and an inside utility with a washer/dryer combo add even more comfort and convenience. Just five minutes from vibrant downtown Winter Haven and next door to the state-of-the-art Advent Health Field House — complete with basketball courts and an Olympic-size swimming pool — this home’s location can’t be beat. Park Lake sits on the shores of beautiful Lake Lulu, where residents can fish from the pier or enjoy skiing right on the water. Perfectly centered near shopping, dining, and grocery stores, this prime location truly offers it all — comfort, convenience, and the best of the Florida lifestyle. Listing agent is owner. Seller Financing Available.

Listing is courtesy of: LIONHEART BROKERS (321-214-4640)

Listing Agent: Claudia Centesimo (407-383-8882)

Remarks: Welcome to this charming three-bedroom, two-bath home nestled in the desirable Lake Daisy Wood neighborhood. Featuring a practical open concept floor plan with tile throughout, this residence is designed for comfortable living. The inviting living room seamlessly connects to a screened porch lanai through sliding glass doors, providing a perfect view of the spacious, fenced backyard—ideal for gatherings or relaxation. The kitchen boasts a convenient breakfast bar and a separate eating area, while a dedicated laundry room connects the garage to the home for added convenience. The generous primary bedroom offers an en suite bath complete with a tub, separate shower, and a large walk-in closet, with its own sliding glass doors leading to the screened lanai. As an added benefit, with a full-price offer, the seller will pay off the solar system in full. This home combines functionality with a welcoming atmosphere, perfect for everyday living.

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

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