Homes For Sale in Winter Haven 33881 - 346 homes

Remarks: MOVE-IN READY! Discover lakeside living at Willowbrook North in Winter Haven, where modern single-family homes meet scenic Florida charm. Nestled near beautiful Lake Fannie and adjacent to the Willowbrook Golf Course, this boutique community offers thoughtfully designed homes with open-concept layouts, energy-efficient features, and stylish finishes. Residents enjoy convenient access to Hwy 27, Downtown Winter Haven, shopping, dining, entertainment, and the new Haines City Target & Crossroads Village. Community highlights include low HOA fees, scenic surroundings, and select homesites with water views. Experience comfort, convenience, and connectivity in one of Winter Haven’s most desirable new home communities.

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

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

Remarks: Under contract-accepting backup offers. Welcome to this 2-bedroom, 2-bathroom ground-floor condo in the desirable Lake Buckeye community. This home features a bonus room and includes the washer and dryer for move-in ease. Step inside and enjoy seamless indoor-outdoor living with a cozy open patio off the dining area. The community enhances your lifestyle with amenities such as a sparkling pool, fishing pier, dock all while showcasing tranquil views of Lake Buckeye that make every day feel like a retreat. Ideally located just minutes from Polk State College, Winter Haven Hospital, Bond and Gessler Clinics, and the lively downtown of Winter Haven, you’ll enjoy easy access to dining, breweries, shopping, the farmers market, and seasonal events. Publix and the Diamond plex sports complex are less than 10 minutes away, Legoland Resort is only 15 minutes, and world-class attractions like Walt Disney World and Universal Studios are about an hour’s drive. With leasing permitted and no age restrictions, this property is an excellent choice for both homeowners and investors. Don’t miss your chance to make it yours.

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

Listing Agent: Brian Cox (863-559-3627)

Remarks: Welcome to this beautifully maintained waterfront home on an oversized lot in the desirable Island Lakes community. This contemporary residence combines comfort, functionality, and breathtaking lake views. Step inside to discover an open-concept floor plan with soaring cathedral ceilings, abundant natural light, and a desirable split-bedroom layout. The spacious primary suite has views of the lake and access to the screened in back porch. The ensuite includes a large walk-in closet, dual vanity, soaking tub, shower and private water closet. The comfortable great room flows seamlessly into the kitchen and dining areas, creating the perfect setting for everyday living and entertaining. Secondary bedrooms are generously sized and perfect for family and guests. The true highlight of this property is the direct frontage on Lake Rochelle, part of Winter Haven's renowned Chain of Lakes. Your private dock is perfect for fishing or parking your boat. Enjoy peaceful views and breezes from the screened rear porch overlooking the water. Roof replaced in 2024, all new LVP in the family and dining rooms. Whether you enjoy boating, fishing, water sports, or simply relaxing by the lake, this property offers the Florida lifestyle you've been dreaming of. Pack your bags and move in today!

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

Listing Agent: Amy Moline (407-506-7447)

Remarks: Here we go, back to market, Buyer default! The property you are inquiring about is located in Winter Haven, FL, in the Winter Haven Harbour area of Polk County. Now conveniently located is this corner unit with beautiful window views from the third floor, and with recent updates. The A/C is newly installed (Dec 2025). Two bedrooms, 1 bath, with every square inch utilized for practical purposes. The community is a 55+ and is conveniently located in the heart of convenience. The HOA fees are low by comparison to what is included in the fee. Vacant and ready for occupancy. Text or call for your private viewing. *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: Location is Key! NO HOA! New Roof, New AC, 3 New Bathrooms, New Front Door, New Floors etc. Next to Polk State College, Lake Elbert Walking Path, Boat Launch and only 2 miles from Downtown Winter Haven. Fresh paint inside and out. The West side of the house has its own access if you want to use the 3rd bedroom as a mother-in-law suite or rent it out privately. The house access is through the newly paved back alley with a large carport in a quiet neighborhood. This house is a great place for a family or someone looking to enjoy the lake, walking path, quiet neighborhood or outdoors.

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

Listing Agent: Keith St. Onge (863-651-1397)

Remarks: Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. In addition to the home’s like-new condition and thoughtful upgrades, qualified buyers may also have the rare opportunity to assume the seller’s existing 5.125% mortgage — potentially creating estimated monthly savings of more than $250 compared to many current market interest rates. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows seamlessly, making it perfect for both everyday living and entertaining. The kitchen is a standout feature, enhanced with a stylish backsplash on the island and throughout, complemented by upgraded light fixtures that add a polished, custom feel. The home also features low-maintenance quartz countertops as well as stainless steel appliances. This home has already been elevated beyond builder-grade with valuable improvements, including solar panels for energy efficiency, a vinyl privacy fence for added outdoor enjoyment, and upgraded ceiling fans and lighting throughout. Tile flooring in the wet areas offers durability and easy maintenance, while cozy carpeting in the bedrooms creates a comfortable retreat at the end of the day. Step outside and enjoy a backyard space that’s ready for relaxing evenings, pets, or gatherings—fully enclosed for privacy and convenience. Location is where this home truly shines. Situated just about one and a half miles from the soon-to-open Publix shopping plaza, you’ll have everyday essentials right around the corner. Plus, you’re only minutes from downtown Winter Haven, known for its charming local shops, dining, and access to the Chain of Lakes lifestyle. Commuters will appreciate the quick access to US-27, making travel to surrounding areas simple and efficient. If you’ve been searching for a move-in-ready home with upgrades already done, modern finishes, and a prime location, this is one you don’t want to miss.

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

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

Remarks: Don’t miss this beautifully renovated 2-bedroom, 1-bath home conveniently located near downtown Winter Haven and just minutes from Polk State College. Whether you’re a first-time homebuyer, downsizing, or looking for a great investment property, this home offers exceptional value and is priced to sell. Recent updates provide a fresh, modern feel throughout, making this property truly move-in ready. Enjoy the convenience of a covered carport, a spacious screened patio perfect for relaxing or entertaining, and a large backyard with plenty of room for outdoor activities, pets, or future improvements. With its prime location, updated condition, and strong rental potential, this home is an excellent opportunity for both homeowners and investors alike. Schedule your private showing today before it’s gone! Some photos have been virtually staged

Listing is courtesy of: OFFERPAD BROKERAGE FL, LLC (813-534-6326)

Listing Agent: James Wible (813-440-0477)

Remarks: Brand-new 3-bedroom, 2.5-bath two-story townhome with garage in Winter Haven, FL. The open-concept main level features a spacious living area, flex space, powder room, and private covered lanai. The professionally designed kitchen includes a breakfast bar, 36-inch soft-close birch cabinets, premium laminate countertops, walk-in pantry, and Samsung stainless steel appliances. Upstairs, the owner’s suite offers a walk-in closet and en-suite bath with dual vanities and a tiled shower, while two additional bedrooms share a dual-vanity hall bath. Features include luxury vinyl plank flooring in main areas and baths, stain-resistant carpet in bedrooms, LED lighting, built-in pest control, and energy-efficient construction with Low-E windows, R-30 insulation, and a programmable thermostat. Move-in ready and easy to maintain.

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Under Construction. New construction home with 1715 square feet on one-story including 4 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty ***Please note - Virtual Tour/Photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!

Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL (863-797-4999)

Listing Agent: George Lindsey, Iii (863-797-4999)

Remarks: Great opportunity to obtain a house at a lower price. The house has new kitchen and new bathroom. No HOA fees. Can be purchase with a low monthly mortgage payment.

Listing is courtesy of: RODRIGUEZ PROPERTY MANAGEMENT (407-936-4061)

Listing Agent: Ivette Graves (407-936-4061)

Remarks: Explore this charming 2-bedroom, 1-bath residence set in a peaceful and well-located Winter Haven community. Large lot with great potential. Bring your paint brush and toolbox and make it your own or make it your next investment.

Listing is courtesy of: THE WILMOTH GROUP (813-471-2503)

Listing Agent: Jen Wilmoth (239-233-4586)

Remarks: Welcome to this beautifully refreshed 3-bedroom, 2-bath pool home in Winter Haven with NO HOA! Situated on a spacious lot in the established Stately Oaks community, this move-in ready property offers comfort, flexibility, and the Florida lifestyle buyers are looking for. Inside, you’ll find bright updated living spaces with fresh finishes, abundant natural light, and a functional layout designed for everyday living and entertaining. The kitchen features clean modern updates, ample cabinetry, and flows seamlessly into the main gathering areas. Step outside to your private backyard retreat featuring a sparkling pool, covered outdoor space, and plenty of room to relax, entertain, and enjoy year-round outdoor living. The oversized driveway offers additional parking and convenience. Additional features include public water and public sewer connections and no HOA restrictions. Conveniently located near shopping, dining, schools, recreation, and major roadways with easy access throughout Central Florida. Schedule your private showing today!

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

Listing Agent: Chelsey Palmowski (863-326-2279)

Remarks: Unlock Incredible Income Potential in Winter Haven! This unique property at 1101 28th St NW is the ultimate value-add or "house-hack" opportunity you’ve been waiting for! While public records show a 2/1, the property features a spacious 3-bedroom, 2-bathroom layout, completely optimized with a separate, income-producing apartment unit that is currently rented. Whether you are looking to offset your mortgage by living in one side and renting the other, accommodating multi-generational living, or adding an asset to your portfolio, this property delivers. Sold AS-IS—bring your vision and capitalize on this rare find today!

Listing is courtesy of: OUTLET REALTY (407-353-5518)

Listing Agent: Yulimar Machado (407-485-1239)

Remarks: Schedule your showing before it’s gone!! Check out this beautiful custom home. It sits on a big corner lot and it is the newest house in the neighborhood. Some of the items this home comes with include 9’4 ceilings, 8ft doors, open floor concept, crown molding, St. Augustine grass, irrigation system, insulation injected into the block, custom stone back wall in the living room, ceramic tile, granite counter tops, custom closets, a range hood, real wood cabinets, a back patio pergola, gutters,LED lighting throughout the home and so much more!! So schedule your showing to see this beauty before its to late.

Listing is courtesy of: FREEDOM PROPERTY AGENT LLC (407-530-4600)

Listing Agent: Santiago Arroyo (863-307-5212)

Remarks: Cute as a button. Great starter home or investment property. Large corner lot. Featuring NEW ROOF, NEW SEPTIC, NEW ELECTRICAL PANELS. This three bedrooms one & one half bathroom has a new modern eat in kitchen and laminate floors. Open spacious living and dining room. Covered front porch. Why rent just buy. Adjoining vacant lot is not included in the sale and has been removed from the legal description. Lot maybe purchased separately.

Listing is courtesy of: CAPITAL REALTY GROUP FLORIDA (407-447-7253)

Listing Agent: Angela Chapman (407-447-7253)

Remarks: Nestled on beautiful Lake Hartridge, is this completely remodeled and move-in ready, stunning 2-bedroom, 2.5-bath condo in Casa Del Sol Village. This unit offers modern updates and a comfortable layout in the heart of Winter Haven. Every inch has been refreshed — featuring luxury vinyl flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living area and guest half bath downstairs make entertaining easy, while both upstairs bedrooms feature private ensuite baths for added convenience. Enjoy low-maintenance living with a 2-car attached garage, access to the community pools, and a location that’s close to shopping, dining, and the Chain of Lakes. Perfect as a primary home, seasonal retreat, or investment property — this move-in-ready condo combines style, comfort, and convenience in one incredible package.

Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)

Listing Agent: Nikki James (863-581-3499)

Remarks: This property is eligible under the 30 Day Freddie Mac First Look Initiative through 05/28/2026. OWNER OCCUPIED BUYERS and NSP offers will only be considered the first 30 days from initial MLS input date. Investors are encouraged to make an offer and will be considered after the First Look Initiative period has expired. Buyer pays Doc Stamps on deed. This 2022 home is barely lived in, Island kitchen opens to the great room plan, hard surface counter tops in the baths, 2 car garage, water filtration system. Home is in great condition. Call today to preview this home.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Barry Macchione (863-604-7455)

Remarks: Welcome to this beautifully maintained home offering 2 bedrooms and 2 bathrooms plus an office in the desirable 55+ community of Brookhaven Village, where you OWN your land! Situated on a large lot with NO rear neighbors, this property offers an incredible sense of privacy & tranquility. From the moment you enter, you’ll notice the care and updates that have gone into this home over the years. Features include updated windows, fresh interior paint, and modern flooring throughout. Both the roof & the AC were replaced within the last 5 years, ensuring peace of mind for years to come. The water heater was just replaced (02/2026). At the front of the home, the Florida room is fully enclosed and equipped with central air & heat, making it a comfortable year-round living space. The open floorplan flows seamlessly into a spacious living room, dining room with built-ins, and a bright kitchen offering ample cabinet & countertop space. The refrigerator was replaced 2 years ago, and the kitchen and bathroom cabinets have been repainted with updated hardware and modern light fixtures added for a fresh look. Down the hallway, you’ll find a dedicated office, ideal for working from home or enjoying a favorite hobby. The guest bedroom includes a walk-in closet, and the guest bath has been tastefully updated. The oversized primary suite is located at the back of the home and features a large walk-in closet and an ensuite bathroom with dual sinks and a walk-in shower. Step outside to your screened-in lanai, perfect for morning coffee or afternoon relaxation. Beyond that, the backyard oasis features a paved patio and serene views; your own private retreat. Hurricane shutters were just installed, adding extra protection and value. The low $34/month HOA fee includes access to the clubhouse, heated pool, shuffleboard courts, and storage area (upon availability). Brookhaven Village offers a prime Central Florida location close to HWY-27, providing easy access to I-4, Tampa, Orlando, and both Gulf and Atlantic beaches. Be sure to explore the 3-D virtual tour, then come see this wonderful home in person. Whether you’re escaping cold winters or seeking an affordable year-round lifestyle, this home is ready for you to enjoy the Florida sunshine. Schedule your private showing today!

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

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

Remarks: Welcome to this stunning Bradley floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 2-bath home offers 1,625 square feet of living space, and provides excellent curb appeal in it's elevation. Inside, you'll find gorgeous White cabinets complemented by sleek quartz countertops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests. This home is ideally situated just minutes from the scenic Port 27 and downtown Winter Haven, making it convenient for shopping, dining, and entertainment. Additionally, it's only a short drive to Highway 27 and about 20 minutes to I-4, providing easy access to nearby cities and attractions. Don’t miss the chance to own this beautiful home in a prime location—schedule your tour today!

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

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

Remarks: Let's make a deal!! Bring them an OFFER!! Turn Key House on the North Chain of Lakes. 2023 Roof, 2022 POOL! Welcome to this pristine, beautifully maintained home in the quiet and highly desirable Island Lakes community—where there’s no through traffic and peaceful living comes naturally. Gorgeous real hardwood floors, stand up tub for the later years, huge shed and a low HOA fee. Step outside and you’ll fall in love with the vinyl-planked dock that gives you direct access to the Chain of Lakes, making it ideal for boating, fishing, and sunset cruises. Whether you prefer relaxing in the screened-in outdoor area or lounging by the sparkling pool, this home is designed for anyone who loves outdoor living. Inside, the home is in immaculate condition. It offers three bedrooms, including a spacious master suite complete with a walk-in tub for easy washing and added convenience. Every room feels well cared for, move-in ready, and prepared for its next owner to enjoy. This stunning property truly has it all—comfort, water access, serenity, and style. It’s ready and waiting for the next buyer who wants to fully embrace lakeside living.

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

Listing Agent: Keith St. Onge (863-651-1397)