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

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: 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: 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: 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: ***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: 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: 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)

Remarks: Under contract-accepting backup offers. Short Sale. One of the most sought-after floor plans, this 4-bedroom, 2-bathroom home boasts numerous charming features and is set on an oversized lot with no rear neighbors and a serene water view. As you enter, you'll find three spacious bedrooms and a modern bathroom. To the left, the inviting, contemporary kitchen showcases a large pantry offering ample storage space. The open dining area flows seamlessly into the airy living room, creating a perfect space for gatherings. Step outside to your private screened-in patio and enjoy the expansive yard with a tranquil, picturesque view. The luxurious Master Suite features dual sinks and a generous walk-in closet. The kitchen island and open layout are perfect for entertaining. This home comes complete with all major appliances, blinds, and is equipped with Smart Home Technology, including Alexa. Conveniently located near I-4, shopping, and entertainment, and offering access to a community pool. All of this at an unbeatable price in an up-and-coming location!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Krichely Gonzalez Rodriguez (407-953-4377)

Remarks: Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)

Remarks: Short Sale. "SHORT SALE!! Seller accepting CASH ONLY!! APPROVED SHORT SALE PRICE BY LIEN HOLDER. Needs TLC. This midcentury POOL home has much potential. It features 3 bedrooms and 3 baths. It has a formal living room area, an office area and a large dining/family room for family gatherings. The fireplace has been converted to gas. Pool enclosure can be developed to be an amazing outdoor space. There is NO HOA, NO CDD and NO FLOOD ZONE is this well-established neighborhood. Located close to popular restaurants, shopping centers, and Legoland Florida Resort & Park, banks and lakes. It is tucked away, yet close to it ALL.

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

Listing Agent: Kelly Hansell (863-557-1784)