Homes for Sale Near Winter Haven Senior in Winter Haven - 177 homes

Remarks: Fully Renovated! Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 5-bedroom, 3-bathroom home. Featuring a brand-new kitchen, updated living spaces, new flooring throughout, and completely renovated bathrooms, this property is truly move-in ready. Recent upgrades include a new roof (2024), new electrical panel, new water heater, fresh interior and exterior paint, and all-new lighting and ceiling fans. The kitchen is a standout, showcasing quartz countertops, new cabinetry, stainless steel appliances, and modern finishes. Enjoy the warmth of a cozy wood-burning fireplace or step outside to your private oasis with a resurfaced pool and a spacious, fully fenced backyard—perfect for entertaining or relaxing. Located between Orlando and Tampa with no HOA or CDD, this home offers flexibility, freedom, and excellent investment potential. Conveniently close to major highways, theme parks, shopping, and dining. Short-term rentals are allowed, making this a great opportunity for both homeowners and investors.

Listing is courtesy of: GARCIA REALTY GROUP (407-920-3616)

Listing Agent: Erika Pinto (407-460-4097)

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: This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and a large backyard—ideal for entertaining or relaxing outdoors. This home is light and bright and move-in ready just for you! The kitchen features white raised-panel PVC cabinetry, black tile countertops, a closet pantry, and updated appliances including a refrigerator (2026) and stove (2022). Major system upgrades include a new 3.5-ton A/C system with new ductwork and a roof replaced in 2022. The split-bedroom layout offers privacy, with both bathrooms very nicely updated. The spacious primary suite includes a beautiful bath with stone floors, a quartz vanity with integral sink and wall-mounted faucet, and a walk-in shower with new tile, glass doors, and drain pan—part of a $15,000 renovation. Additional highlights include a garage with mini-split A/C, insulated garage door, pull-down ladder for attic access, washer/dryer hookup, and laundry sink. Outside you will have a 10’x12’ shed with electric, and a well house with a Culligan water softener system. A new black aluminum fence surrounds the property, with vinyl PVC privacy fencing along the left side, 12-foot gates on both sides plus a 6-foot front gate—perfect for storing a boat, RV, or extra vehicles. A covered rear carport adds even more flexibility. Conveniently located on a large corner lot near lakes, parks, recreation areas, LEGOLAND, Hwy 27 & I-4, and all that Central Florida has to offer. Welcome home!

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

Listing Agent: Russ Rhoads (863-604-1570)

Remarks: PRICE REDUCTION! 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, tankless water heater, and leaf filter gutter guards. Ready for your finishing touches!

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

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

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: New Price! Move-in ready Central Florida home featuring an open-concept floor plan, high ceilings, and fresh interior paint. Recent upgrades include luxury vinyl plank flooring throughout the main living areas and durable vinyl flooring in all bedrooms—no carpet. The modern kitchen offers quartz countertops, espresso cabinets with crown molding, a center island, and Samsung stainless steel appliances. The spacious primary suite includes dual vanities, a walk-in closet, and a private en-suite bath. Additional features include a whole-home water softener and filtration system, custom blinds, ceiling fans, washer and dryer, programmable thermostat, and Ring doorbell system. Enjoy a fully fenced backyard with updated landscaping and irrigation, plus a covered patio for outdoor living. Built with energy-efficient windows and insulation, this home also offers a two-car garage, architectural shingles, and access to community amenities including a pool and playground. Conveniently located and ready for its next owner—schedule your private showing today.

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

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

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

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

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

Remarks: Welcome home to this newer 3-bedroom, 2-bath residence built in 2020, offering 1,672 square feet of thoughtfully designed living space. The open-concept layout creates a bright and inviting atmosphere, with the living, dining, and kitchen areas flowing together to accommodate both everyday living and entertaining. The primary suite features a walk-in closet, while the primary bathroom is equipped with dual sinks and a walk-in shower for added convenience. With a functional floor plan and modern design, this home provides the ideal blend of comfort and practicality. The home is ready to be converted into your ideal living space. Don't miss your opportunity to make this home yours—schedule your private showing today! The 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. Enclosed Saltwater Pool | Corner Lot | 4 Bedrooms in Winter Haven - New Roof May 2026! Welcome to 310 17th St NE in Winter Haven, FL — a charming 4-bedroom, 2.5-bath pool home set on a spacious 0.28-acre corner lot in an established neighborhood. This home offers a blend of character, space, and opportunity for the next owner. Inside, you'll find nearly 1,800 sq ft of living space with a functional layout that includes four bedrooms, 2 full bathrooms and a convenient half bath, offering flexibility for guests, home office space, or everyday living. The kitchen and bathrooms retain their original style, giving buyers the chance to update and personalize over time. Step outside and enjoy the enclosed saltwater pool (installed in 2018), creating a private outdoor space for relaxing or gathering with friends. The fenced backyard and large corner lot provide room to spread out and enjoy outdoor living. Major systems have already been updated, including AC (2020) and water heater (2018). The home also offers 2,267 total square feet under roof, adding additional usable space. FHA Appraisal came in at $322k! Conveniently located near shopping, dining, schools, and major roadways, this property combines the charm of an established Winter Haven neighborhood with everyday convenience.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Jenelle Grabowicz (863-604-0834)

Remarks: Beautiful 4 bedroom, 2 1/2-bathroom, 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: POOL HOME ON AN OVERSIZED CORNER LOT WITH A SCREENED LANAI, DETACHED SHE SHED/MAN CAVE, AND A FULLY FENCED BACKYARD! Tucked beneath mature shade trees in Winter Haven's established High Point community, this well-maintained home offers the space, flexibility, and outdoor living opportunities that many buyers have been searching for. From the inviting covered front porch to the multiple outdoor gathering areas, every part of this property is designed to be enjoyed. Step inside to a bright and welcoming interior where natural light fills the living spaces and creates a comfortable atmosphere throughout. The living room serves as the heart of the home and flows effortlessly into the dining area and kitchen, creating a layout that feels connected and functional for both everyday living and entertaining. The kitchen features ample cabinetry, generous countertop space, stainless steel appliances, breakfast bar seating, and easy access to the home's outdoor living areas. The home offers three comfortable bedrooms, each providing flexibility for family, guests, hobbies, or a home office. The centrally located bathroom features a dual-sink vanity with ample storage and countertop space. An indoor laundry room adds everyday convenience, and an additional flexible room currently used for storage offers opportunities for future use based on your needs. One of the home's standout features is the expansive screened lanai stretching across the rear of the property. This impressive outdoor living space creates the perfect setting for morning coffee, outdoor dining, game days, or relaxing evenings while enjoying Florida's beautiful weather. Beyond the lanai, the fully fenced backyard offers multiple areas to gather, entertain, and unwind. The above-ground pool creates a refreshing backyard retreat surrounded by mature landscaping and outdoor living spaces. A detached 12x20 she shed/man cave provides exceptional flexibility and can easily be utilized as a hobby room, creative studio, fitness space, game room, workshop, or private retreat. The property also features two separate carports, providing covered parking and additional space for vehicles, equipment, projects, and everyday convenience. The oversized corner lot offers additional outdoor space and versatility rarely found in many homes of this size. Whether you're hosting family gatherings, working on hobbies, gardening, relaxing by the pool, or simply enjoying the shade of the mature trees, this property provides room to live, work, and play. Conveniently located near shopping, dining, parks, schools, medical facilities, Winter Haven's renowned Chain of Lakes, Legoland Florida Resort, downtown Winter Haven, and major roadways connecting throughout Central Florida, this home offers convenient access to everyday essentials and local recreation. If you've been searching for a property that offers more than just a house—a place with room to gather, relax, create, and enjoy the Florida lifestyle—this home is ready to welcome its next owner.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Simi Lakhani (407-408-7393)

Remarks: Don't miss this rare opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas complete with a kitchen breakfast bar. All NEW luxury vinyl flooring, NEW windows and sliding glass patio door, NEW kitchen countertops, and fresh interior paint offer efficiency, comfort, and modern elegance. Walk-in closets in both bedrooms offer an abundance of space for organizing your belongings, and an en suite bathroom in the main bedroom for privacy and convenience with a serene pond view from the primary bedroom. Enjoy the open-concept living area for entertaining friends and family and a private patio further compliment this delightful property. Immerse yourself in the outdoors on your private gated patio or take a walk, run, or bike ride to enjoy the natural scenery that abounds in this community. Cypresswood Golf and Country Club features a 24-hour manned guard gate, 18-hole championship golf course designed by Ron Garl, junior Olympic-sized community pool, lighted tennis/pickleball/basketball courts, clubhouse, restaurant, pro-shop, event space, and so much more. The low monthly HOA fee includes all exterior and grounds maintenance, pest control, trash collection, and use of the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual membership! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today!

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: Under Construction. The Ponte Vedra floor plan at Willowbrook North offers spacious two-story living with 5 bedrooms, 3 full baths, and approximately 2,371 square feet of thoughtfully designed space. This open-concept home features a modern kitchen overlooking the great room and dining area, a spacious primary suite, flexible living areas, and available options. Located near Lake Fannie and adjacent to Willowbrook Golf Club, Willowbrook North offers scenic surroundings with convenient access to shopping, dining, parks, downtown Winter Haven, and major commuter routes to Orlando and Tampa. Buyers will also enjoy energy-efficient features and modern interior finishes.

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

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

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Newly renovated 2 bedroom, 2 bathroom home with all the major updates already done for you — new roof, new floors ,new AC, and new water heater. This is a boater and fisher’s dream property located on beautiful Lake Dexter, Enjoy boating, water skiing, and freshwater fishing right from your backyard playground. The community offers a dock with boat slips available on a first-come, first-served basis, perfect for boats up to 24 feet. Residents also enjoy a clubhouse, pickleball courts, and tennis courts, making it easy to enjoy the Florida lifestyle. Whether you're looking for a full-time residence or a weekend lake retreat, this home offers the perfect mix of updates, amenities, and waterfront living.

Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)

Listing Agent: Danielle Davis (813-526-5002)

Remarks: Back on market buyers financing fell through. 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: This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearly non-existent electric bills thanks to a fully paid-off SolarEdge solar system, complemented by a whole-house 22 kW Generac generator with a 250-gallon propane tank, hurricane-rated windows, a 5-year-old architectural shingle roof, and a Rinnai tankless water heater. The spacious interior boasts a large galley kitchen with stainless steel appliances and a gas stove, a convenient indoor laundry room with extra storage, a 2-car garage, and a versatile 16x12 climate-controlled Florida room. This property has been an Airbnb and can be purchased fully furnished, making it a turnkey investment or a move-in-ready retreat!

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buyers are searching for in Polk County. If you've been looking for a move-in ready home with a private pool, screened spa, modern finishes, and no rental restrictions, this property deserves a spot at the top of your list.Located in the established Buckeye Pointe community, this spacious two-story home features 5 bedrooms, 2.5 bathrooms, and more than 2,500 square feet of living space. The versatile floor plan includes a first-floor bedroom, making it ideal for multigenerational living, visiting guests, a private home office, or a fitness room.From the moment you step inside, you'll notice the extensive updates throughout. The entire first floor showcases oversized 24x36 porcelain tile, creating a clean, modern look that is both stylish and easy to maintain. The renovated kitchen serves as the heart of the home with updated cabinetry, a large center island, upgraded lighting, and newer appliances including the refrigerator and dishwasher. Every bathroom has been remodeled, while fresh interior and exterior paint give the home a bright, updated feel throughout.Step outside and enjoy the Florida lifestyle year-round. The screened and heated pool and spa create the perfect setting for relaxing after work, entertaining family and friends, or enjoying weekend gatherings. The vinyl fenced backyard offers privacy, while mature fruit trees provide character and charm that are increasingly difficult to find. Major improvements include a newer 2023 roof and a 2020 water heater, giving buyers added confidence and helping reduce future maintenance concerns. One of the most attractive features of this property is the absence of rental restrictions. Buyers searching for an Airbnb-friendly home in Winter Haven, a Florida vacation home, a second home near Orlando attractions, or an income-producing investment property will appreciate the flexibility this community offers. Conveniently located near shopping, restaurants, medical facilities, schools, and major transportation routes, this home provides easy access to everything Central Florida has to offer. Whether you're commuting to Orlando, exploring nearby lakes, visiting world-famous attractions, or simply enjoying the growing Winter Haven lifestyle, this location puts you close to it all.Buyers frequently searching for "homes with pools in Winter Haven," "5-bedroom homes in Polk County," "updated homes near Orlando," "Airbnb investment properties in Central Florida," "homes with no rental restrictions," or "move-in ready Florida homes with a pool" will find everything they're looking for at 3097 Buckeye Pointe Drive. This is more than just a house. It's a move-in ready Florida lifestyle with room to grow, space to entertain, and the flexibility to fit your future plans.

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

Listing Agent: Desiree Carlson (541-743-1985)

Remarks: ~2/2 Winter Haven residence Offered for Sale~ Great opportunity for a first-time home buyer or an investor! This adorable 2/2 property features 1396 square feet of living area, a split plan, two bonus rooms which could be used as bedrooms, vaulted ceilings, primary bedroom with walk-in closet and en-suite bath, wood burning fireplace, large, screened patio and a one car garage. Roof and A/C are less than 5 years old and water heater is newer. Convenient to fishing, dining, shopping, and medical/educational facilities. Monthly HOA fee covers grounds maintenance, streetlights and community pool care.

Listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM (863-940-3756)

Listing Agent: Andrea Muzzy (863-430-1733)

Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.

Listing is courtesy of: WF REALTY CORP. (407-994-2900)

Listing Agent: Adriana Sanchez (321-947-4014)

Remarks: Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite serves as a private retreat and features sliding glass doors leading to a screened and covered lanai. A portion of the lanai has been enclosed to create a flexible bonus room—ideal for a home office, reading nook, fitness area, or hobby room. Step outside to your private tiled patio, the perfect place to enjoy your morning coffee, unwind after a long day, or host family and friends. This sought-after community offers amenities rarely found at this price point, including assigned covered parking, a sparkling community pool, and direct access to beautiful Lake Smart with a private boat ramp. Whether you enjoy boating, fishing, kayaking, or simply watching the sunset over the water, you'll love the lifestyle this community provides. Located just minutes from shopping, restaurants, medical facilities, and major roadways, this move-in-ready home offers the convenience buyers are looking for and the Florida lifestyle they dream about. Opportunities like this don't come along often. Schedule your private tour today and discover why this could be the perfect place to call home.

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

Listing Agent: Diana Acosta (914-562-3386)