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

Remarks: Nestled in the heart of Winter Haven just north of Lake Lulu, this charming block home captures the true essence of a hometown retreat. Inside, the 1,338 square feet of living space feels warm and inviting, featuring a classic living and dining layout that flows into a versatile Florida room—currently used as a cozy third bedroom. Peace of mind comes standard here, thanks to a sturdy roof installed in 2019 and a solid construction that has stood the test of time. Step outside into your private sanctuary, where a spacious 0.24-acre fenced yard offers plenty of room for pets to roam or for gardening under the Florida sun. The property is a hobbyist’s dream, equipped with two large storage sheds (240 and 96 square feet) that provide ample space for a workshop, gear, or seasonal decor. The location truly bridges the gap between quiet residential living and urban convenience; you are just a short, breezy walk from the Publix Shopping Plaza, Walmart, and a variety of local restaurants. For those seeking a bit of magic, LEGOLAND Florida Resort is only 15 minutes away, while the vibrant amenities of downtown Winter Haven are practically at your doorstep. This is more than just a house; it’s a place to plant roots in a community that feels like home. Go ahead and schedule a showing today.

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

Listing Agent: Twanna Dewdney (863-207-1634)

Remarks: Under contract-accepting backup offers. Welcome to 1930 Austin Terrace, located in the highly desirable gated community of Woodpointe in SE Winter Haven. Perfectly situated near Hwy 27 and just minutes from LEGOLAND Florida Resort, this home offers both convenience and a peaceful cul-de-sac setting on a spacious fully fenced 0.32-acre lot.This beautifully designed 4-bedroom, 3-bathroom POOL home welcomes you with an elegant entry foyer, soaring specialty ceilings, and wood flooring throughout, complemented by ceramic tile in the foyer, kitchen, breakfast nook, and bathrooms. The thoughtfully designed layout includes a formal dining room and an open, inviting living space ideal for both everyday living and entertaining. The kitchen features granite countertops, a new refrigerator (04/2026), a breakfast bar, and a walk-in pantry, with a cozy breakfast nook overlooking the saltwater pool for relaxed mornings. Step outside to enjoy true Florida living with a screen-enclosed pool, covered lanai, and a beautifully paved pool patio, perfect for hosting or unwinding in your private, fully fenced backyard. The pool system has been well maintained with a new pool pump (09/2025) and recently updated salt cell and WiFi-enabled motherboard (03/2026), offering modern convenience and efficiency. The spacious primary suite serves as a private retreat, complete with an additional office space, fireplace, walk-in closet, and an ensuite bathroom featuring a split sink vanity, garden tub, and separate shower. Additional highlights include a newer AC system (approximately 4 years old), a brick-paved driveway and walkways, and a charming covered front porch accented by columns, adding to the home’s curb appeal. A brand new roof will be put on before closing! This exceptional property offers the perfect combination of space, style, and location in one of SE Winter Haven’s most sought-after gated communities.

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Located in the highly sought-after gated community of Lakewood, this beautifully maintained home offers 4 bedrooms and 3.5 bathrooms, set on a lush, manicured lot with mature trees and attractive landscaping. Inside, you’ll find rich wood flooring throughout the spacious living and dining areas, as well as the kitchen and family room—perfect for both everyday living and entertaining. A standout feature is the expansive 480 sq ft detached game room, included in the total living area, complete with a full bathroom and generous closet space—ideal for conversion into a private guest house, in-law suite, or home office. The primary suite boasts a recently renovated en-suite bathroom and direct access to the large screened lanai and pool area, creating a relaxing retreat. Major updates include a roof replacement in 2017. This exceptional property offers space, flexibility, and charm—don’t miss your opportunity to make it yours!

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

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

Remarks: Under contract-accepting backup offers. Enjoy this clean 2 bedroom, 2 bath villa in the community of Mayfair Place. Step into a spacious great room with soaring ceilings and all ceramic tile floors throughout, offering both style and ease of maintenance. The open kitchen includes plenty of counterspace, gas range/stove, and breakfast bar. The primary suite features sliding glass doors leading to a peaceful back patio, the perfect spot for morning coffee or winding down in the evening. Inside utility room with extra cabinet and counter space, plus an additional storage closet for even more convenience. Just minutes from downtown, this villa provides easy access to local dining, shopping, and medical facilities.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Under Construction. The Freeport II floor plan at Willowbrook South offers the perfect blend of comfort, functionality, and modern design. Built with durable all-concrete block construction, this one-story home maximizes living space with a bright, open-concept layout that’s ideal for everyday living and entertaining. As you enter through the foyer, you’ll find two spacious guest bedrooms and a full guest bath with a modern vanity. A convenient linen closet is positioned between the bathroom and bedrooms for easy storage. Further down the hallway, a third bedroom offers flexibility for a home office or guest space, alongside a private laundry area and direct access to the two-car garage. The heart of the home features a well-appointed kitchen with stainless steel appliances, overlooking the dining area, great room, and covered patio perfect for gatherings and family time. Tucked at the rear of the home, the primary bedroom offers a peaceful retreat with a walk-in closet and a spa-inspired bathroom featuring a double vanity sink and a spacious shower. Every home in Willowbrook South comes equipped with the Home Is Connected Smart Home Technology package, allowing you to control locks, thermostat, and more right from your smartphone whether you’re home or away. With its thoughtful design and modern features, the Freeport makes owning a new home in Winter Haven, FL both easy and enjoyable. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: Under Construction. Let me Introduce you to our 5 Bed 2 Bath 1708sqft floor plan the Dundee. This home provides you with Luxury Vinyl Tile in all the wet areas and the living and dining rooms with Quartz Counter Tops in the Kitchen and Bathrooms. The Kitchen provides Stainless Steel Whirlpool Appliances that Including a Stove, Microwave, Refrigerator and Dishwasher, and a Washer and Dryer in the Laundry room. You have 4 Spare Bedrooms and an Owners Suite that can easily fit a King size bed with walk in closet. Beautiful Master bath with two Adult Vanity sinks and Quartz Countertops.

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Paul King (407-519-3940)

Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 3-bath home located in one of Winter Haven’s most established and sought-after neighborhoods. Situated on a spacious 0.26-acre lot, this property offers timeless character, mature surroundings, and a location rich in local history. A standout feature of the home is the private suite with its own entrance and full bathroom, ideal for guests, extended family, or a flexible work-from-home space. The layout provides both privacy and functionality, making it a rare find in this area. Recent updates include a newer roof (approx. 1 year old), updated electrical, a new water heater, and a newer A/C unit (2018), offering peace of mind on major systems. Enjoy the unique setting with nearby views of Lake Elbert to the north and Lake Otis to the south, surrounded by well-established homes and nearby lakefront properties. The home offers great bones and classic charm, presenting an excellent opportunity for buyers to update and personalize while investing in a premier location. Conveniently located near downtown Winter Haven, shopping, dining, and more.

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

Listing Agent: Dave Westphal (863-287-3302)

Remarks: Located in Osprey Pointe on Lake Ned, 3905 Osprey Pointe Cir. is everything you've been looking for in the heart of Central Florida. This 3 bed, 2 bath home was built to last and withstand anything that comes it's way. Using solid poured concrete tilt walls, the house is incredibly strong and comfortable. Offering over 1700 square feet of air conditioned space, you will never feel confined. The family room, kitchen and dining area have soaring vaulted ceilings, while the primary bedroom feels spacious with a beautiful tray ceiling. The kitchen has many upgrades including solid cabinets, granite counter tops and a natural gas range. You'll also have access to the community clubhouse, pool and dock. With a location just minutes from great shopping, restaurants, grocery stores, medical facilities and Legoland! This home is in great shape and has a wonderful location. It will not last long, come see it before it's gone.

Listing is courtesy of: STRAIGHT UP REALTY & PM LLC (863-698-7547)

Listing Agent: Cole Bataille (863-698-7547)

Remarks: Photos are preoccupancy. Turnkey, Renovated and Occupied Duplex 6.2 miles to Legoland – Make Money From Day 1-Investor Ready! Don't miss this income-producing duplex in a prime Winter Haven location. It is just 15 minutes from Legoland Florida and local shopping plazas. This is the perfect turnkey investment or an excellent opportunity for owner-occupancy with built-in rental income. Enjoy hassle-free ownership with a new roof, new flooring and new, efficient multi mini-split AC systems in both units. Each unit is equipped with new appliances and features modern updates throughout. The property offers a highly desirable configuration: Unit A is a spacious 3 Bed/1 Bath, and Unit B is a comfortable 2 Bed/1 Bath. That is a total of five bedrooms and two bathrooms across two separate units. Located in a high-demand rental market near major employment and amenities, this duplex is ready to generate income from day one. Invest smarter—act now before it's gone!

Listing is courtesy of: SPANN & ASSOCIATES REAL ESTATE (407-468-7512)

Listing Agent: Kal Scarvers (863-617-5236)

Remarks: Welcome to this beautifully renovated 3-bedroom, 2-bath home located in the heart of Winter Haven. Thoughtfully updated with modern finishes while maintaining its charm, this spacious property offers flexible living areas and plenty of room to spread out. Recent renovations provide a fresh, move-in-ready feel throughout the home. Previous owners added extra rooms and expanded living spaces, offering versatility for a home office, guest space, or bonus room. Square footage to be confirmed by buyer, as additions may not reflect current public records. Conveniently located near shopping, dining, schools, and all that Winter Haven has to offer, this property is a fantastic opportunity for homeowners or investors alike.

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

Listing Agent: Patrick Massey (931-337-1678)

Remarks: Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Short Sale. SHORT SALE!! SUBMIT YOUR OFFER & WE WILL SUBMIT TO THE BANK. Welcome to Heather Glen, a gated community in the heart of Winter Haven with an HOA of ONLY $150 A YEAR! This charming 3 bedroom, 2 bathroom home with an attached 2-car garage offers comfort, security, and convenience & ready for a quick close & move in. Featuring neutral gray walls, wood-look tile flooring, and plantation shutters throughout, this open-concept home is filled with natural light and boasts a spacious master suite with walk-in closet and private bath, two additional bedrooms with a guest bath, and a bright kitchen with plenty of counter space, a window over the sink, and a cozy dinette area for your morning coffee. Enjoy the convenience of an interior laundry room, newer roof and A/C unit, and a fully fenced backyard with a separate well for irrigation. Located just minutes from Legoland, Peppa Pig Theme Park, shopping, dining, medical facilities, and downtown Winter Haven, this pristine home is the perfect rental in a sought-after location. Schedule your showing today!

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

Listing Agent: Jeavanna Lanza Pa (585-313-3408)

Remarks: Income-producing 5-unit property located just minutes from downtown Winter Haven in a high-demand rental corridor. This asset is positioned for strong cash flow, operational upside, and long-term appreciation in one of Central Florida’s most active growth markets. The property offers a diversified unit mix with clear value-add potential through rent optimization and continued area development. Ideal for investors seeking to scale a performing portfolio with stable income and future equity growth. Proximity to a planned townhome development introduces an additional demand catalyst, reinforcing long-term rental stability. Convenient access to retail, dining, major thoroughfares, and ongoing redevelopment enhances tenant appeal and occupancy consistency. Units 3 and 4 feature a shared second-floor balcony overlooking the rear grounds, adding a desirable lifestyle element for residents. Located in a high-growth submarket of Winter Haven experiencing sustained residential expansion and increasing rental demand, this is a strategic acquisition opportunity with measurable upside. Contact for full financials, rent roll, and investment details.

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. Discover the perfect blend of modern updates and serene living in this stunning 4-bedroom, 2-bathroom home. Located in the highly sought-after Country Club Estates, this residence offers the privacy you've been searching for with a screened-in back patio overlooking a peaceful pond-meaning no rear neighbors, just tranquil water views. Step inside to find a bright and airy open floor plan, freshly enhanced with new interior and exterior paint. The home is designed for both style and durability: Elegant luxury vinyl plank in all bedrooms and easy-to-maintain ceramic tile throughout the main living areas. Features timeless oak cabinetry, sleek granite countertops, and plenty of prep space. The popular split-bedroom floor plan ensures a private primary retreat, separate from the guest rooms.A dedicated inside laundry room and a spacious 2-car garage provide ultimate functionality. Location is everything! Enjoy the quiet atmosphere of an established community while being just moments away from modern conveniences. The brand-new Publix shopping center is right around the corner, making grocery runs and errands a breeze.Schedule your private showing today and experience Florida living at its finest!

Listing is courtesy of: ORLANDO REO PROF I INC (407-704-6924)

Listing Agent: Ronald Gentile (407-247-0849)

Remarks: Welcome To Hartridge Hills!! This Gorgeous Gated Community is one of Polk County's Hidden Treasures. An established and well maintained community of charming custom homes, each one uniquely it's own. Nestled between Lake Pansy and Lake Hartridge, this community offers boat lovers their own private boat ramp with access to the Chain of Lakes. This community also has been home to many pilots over the years and is conveniently located beside the Winter Haven Airport and only minutes to Publix and all major medical facilities making this community a perfect location. Situated on a corner lot, this well built home by Ernie White is a split plan offering 3 bedrooms & 2 baths plus a den or office space. The dining room, living area and bedrooms have new luxury vinyl. There is High ceilings throughout, crown molding, updated granite in the kitchen and bathrooms. The roof was replaced in 2017. HOA fee's include lawn care and the irrigation system is on a small well, saving you money on your water bill! Grab your favorite beverage & Relax and Enjoy the water views on your enclosed back lanai. Come check out this beautiful property, You'll love being a part of this quaint community!!

Listing is courtesy of: PREMIER HOMES AND REAL ESTATE (863-937-8942)

Listing Agent: Christy Smith (863-409-8709)

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: MULBERRY model is located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2 and a half-bath home offers 1,938 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous gray cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. The open layout is perfect for family gatherings and entertaining guests. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nancy Pruitt, Pa (352-552-7574)

Remarks: Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are newer dual pane windows, tile throughout the living area, and vinyl plank floors in the bedrooms! The air conditioner is only two years old and has a warranty that expires in 2033 and the washer/dryer is only one year old. The interior walls were just painted and this unit is ready for a new owner or tenant! This is one of the nicest units in the complex! Call today to schedule a showing!

Listing is courtesy of: CLARK REALTY LLC (863-345-2155)

Listing Agent: Steven Perkins (863-797-7276)

Remarks: PRE-FORECLOSURE - 3 Bedroom/2 Bath Home in a gated community. This home is only 4 years old, but it needs a lot of cosmetic work. The Buyers may assume the current mortgage at 3% interest.

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

Listing Agent: Linda Andre (863-294-7541)

Remarks: Under contract-accepting backup offers. Welcome to a home where comfort, convenience, and peace of mind come together in one of Winter Haven’s most desirable and evolving areas. Nestled just minutes from the shores of Lake Howard and the charm of Downtown Winter Haven, this property offers the lifestyle so many are seeking—close to it all, yet tucked away in a quiet, established neighborhood.From the moment you arrive, you’ll appreciate the care and updates that make this home truly move-in ready. Major systems have already been taken care of for you, including a brand-new hot water heater installed in 2026, roof and HVAC systems both replaced in 2018, giving confidence for years to come. Inside all-new windows bring in natural light while improving energy efficiency. The home continues to shine with newer cabinets and updated appliances. The interior tells a story of thoughtful updates and everyday functionality—spaces that feel welcoming whether you’re hosting friends, enjoying a quiet evening, or simply living life comfortably. Every improvement has been made with both style and practicality in mind, allowing you to settle in without the stress of immediate projects.Step outside and you’re just moments away from everything that makes Winter Haven special. Spend your weekends enjoying the Chain of Lakes lifestyle at Lake Howard, take in the growing dining and entertainment scene downtown, or simply enjoy the continued growth and investment happening throughout the area—making this not just a great home, but a smart move for the future.If you’ve been looking for a home that blends updated features, prime location, and long-term value, this one checks all the boxes.

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

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