Homes For Sale in Winter Haven 33881 - 342 homes

Remarks: ALMOST PARADISE! Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a study, library and/or den), family room and interior laundry room. Note the Curb Appeal of the landscaping, TILE ROOF and BRICK paver driveway and walkway! The inviting and covered front porch provides respite from inclement weather. As you enter the entry foyer, the living room will be to the immediate left and the dining room to the right. Straight ahead is the family room with a set of sliding glass doors that opens onto the screened in lanai. Settle back, listen to the birds singing and observe the cows on the adjacent ranch property! To the left of the family room are bedrooms #2 and #3 and to the right is the kitchen, dining nook, primary bedroom suite, bedroom #4 and the laundry room! The well planned kitchen has a breakfast bar, white cabinetry with neutral colored solid countertop and stainless steel appliances. The kitchen appliances have been updated from 2018-2025. The spacious primary suite has sliding glass doors leading to the lanai, two walk-in closets and an ensuite bathroom with dual vanities and sinks, jetted tub, separate shower and a water closet! Bedroom #4 is currently used as a home office. The floor plan allows creativity in use. Most recent updates include: Water Heater replaced Feb. 2026; AC/Heat system April 2025; garbage disposal and microwave 2025; and lanai screen & door 2025. The PERIMETER 90 X 120 lot is a generous in size. There is room to add a pool, outdoor kitchen, play area and/or garden! The HOA fee provides re-use irrigation water and maintenance of the gate and common areas. Perfect for a year round or winter residence, this home is a blank canvas just waiting for YOUR decorating touches! For those who enjoy golf and/or tennis, the Country Club of Winter Haven is just 2 Blocks away! Publix Supermarket is conveniently located within 0.8 mile with additional stores and a bank currently under construction! Easy access to downtown Winter Haven, HWY 27 and I-4. Legoland, Bok Tower, world-famous theme parks of Disney, Universal Orlando, Sea World, water adventure parks, downtown Orlando and various other nature parks are within a 7 to 60 mile drive. Be sure to make your appointment to view this outstanding property! Measurements are approximate. All information is believed to be accurate but not guaranteed.

Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)

Listing Agent: Carol Jean Sheil (863-412-3801)

Remarks: Under Construction. New construction home with 2227 square feet on two-story including 5 bedrooms, 3.5 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, and a tiled shower. Bedrooms 2 and 3 share a jack-and-Jill bathroom. 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 decor do not convey."

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

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

Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Casandra Vann (863-546-5446)

Remarks: One or more photo(s) has been virtually staged. Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of Winter Haven's Chain of Lakes. This spacious 2BR/2.5BA townhome that 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 a breakfast bar and a convenient half bathroom. 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 & hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor & 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 & 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: Location Location!! NO HOA, NO CDD, Built in 2020. QUIET, YET CONVENIENT LOCATION! Whether you're shopping for a first home, Investment or last home, this beauty is just what you’ve been looking for! Beautiful 3BR/2BA home open floor plan, living room/dinning groom /family room kitchen combo. located in NE Winter Haven. Large walk in closet in the Master Bedroom/Bath. Master bath contains a shower and tub, as well as double vanity. Kitchen comes equipped with stainless steel appliances, Vinyl flooring consistent through entire home, central a/c and heating. All stainless-steel appliances convey. This home will not last long, call today for your private showing.

Listing is courtesy of: VYLLA HOME (813-947-7996)

Listing Agent: Manny Duran, Jr (407-334-8893)

Remarks: Welcome to this charming 3 bedroom, 1 bath home ideally located in the heart of Winter Haven, just minutes from shopping, dining, and schools. From the moment you arrive, you’ll be greeted by a lush, established front garden, perfect for those who enjoy outdoor living or gardening. The home features a covered front porch, ideal for relaxing mornings or unwinding in the evenings, along with a convenient one-car carport. Inside, you’ll find a warm and inviting living space highlighted by durable wood-look tile flooring that flows seamlessly throughout the main areas. The kitchen and dining room combination offers a functional layout with plenty of room for everyday living and entertaining. Tucked away at the rear of the home, the spacious primary bedroom provides added privacy and a generously sized closet. Two additional bedrooms offer flexibility for guests, a home office, or hobby space. The full bathroom includes a single-sink vanity and a tiled tub/shower combo. Additional features include an exterior storage/laundry room located under the carport with washer and dryer hookups. Whether you're a first-time homebuyer, investor, or looking to downsize, this home offers great potential and opportunity. Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Casandra Vann (863-546-5446)

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: 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: 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: Investors Only. Leased through August 31, 2027, at $2,575/month. Landlord provides lawn care. No rear neighbors and entirely fenced for privacy! Low HOA dues and bonus room/loft plus office space. Open concept with luxury laminate flooring throughout including stairs. Full-sized kitchen island with seating and plenty of counter space for food prep. Stainless steel appliances. The dining and family room combo offers plenty of natural lighting with slider glass doors leading to your outdoor patio overlooking the conservation area. The master bathroom features two (2) walk-in closets. Enjoy the early morning sunrises sitting under your custom-built pergola in back. Screened front porch. Located 6 miles from Legoland Theme Park and Water Park.

Listing is courtesy of: 3% REAL E$TATE (407-479-0076)

Listing Agent: Ray Guenther (407-479-0076)

Remarks: Experience luxury living in this newly built (2023) modern style home featuring breathtaking views of Lake Jessie and no HOA! This spacious 4-bedroom, 4-bath single-family residence offers an expansive open floor plan, soaring ceilings, and porcelain tile throughout. The elegant living room features a dramatic porcelain tile fireplace, creating a warm and stylish focal point. The chef’s kitchen is designed to impress with quartz countertops, stainless steel appliances, sleek modern cabinetry, and ample storage. A spacious indoor laundry room adds everyday convenience. Additional highlights include a 3-car garage, durable tile roof, whole-home water filtration system, and pre-wiring for a security camera system. Enjoy year-round outdoor living with a fully enclosed porch and large paver patio—perfect for relaxing or entertaining. Conveniently located directly across from a public boat ramp, offering easy access to boating and recreation without the upkeep of lakefront ownership. An exceptional opportunity to own a move-in-ready home with thoughtful upgrades, modern design, and a prime location near the water. Schedule your private showing today!

Listing is courtesy of: LANTES REAL ESTATE LLC (813-408-0980)

Listing Agent: Asley Garcia (813-613-2666)

Remarks: LEASE to OWN option available!!! Welcome to 2826 Ave Q NW in Winter Haven — a beautifully remodeled 3-bedroom, 1-bath home designed for comfort, functionality, affordable and modern living. This move-in-ready property features a brand-new roof, updated HVAC system, and new energy-efficient windows, new stainless steel appliances, new granite countertops, new porcelain tile flooring, and so much more! This home offers both peace of mind and long-term value. Inside, you’ll find a thoughtfully refreshed interior with clean finishes and a layout that maximizes space and natural light. Ample storage is a standout feature throughout the home, making it easy to stay organized and clutter-free. The attached carport provides convenient parking along with additional storage space, ideal for tools, equipment, or seasonal items. Situated in a well-connected area of Winter Haven, this home places you close to a variety of everyday conveniences and lifestyle destinations. Enjoy easy access to shopping, dining, and local favorites, as well as major roadways for commuting. Nearby attractions include LEGOLAND Florida Resort, offering entertainment and recreation just a short drive away. The property is also located near reputable healthcare facilities such as Winter Haven Hospital, ensuring accessibility to medical services when needed. A variety of restaurants, parks, and outdoor spaces are within reach, providing options for dining and leisure. Whether you're looking for a primary residence or an investment opportunity, this updated home offers a solid combination of location, upgrades, and everyday convenience. Schedule your private showing today.

Listing is courtesy of: OPULENT REALTY INTERNATIONAL (863-323-7778)

Listing Agent: Alicia Self (863-450-8394)

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: Charming 3-bedroom, 1-bath home with no HOA, offering a great opportunity for investors or first-time buyers alike. Conveniently located in Winter Haven with easy access to shopping, dining, schools, major roadways, and everyday amenities. This property offers plenty of potential and is ideal for those looking to expand their portfolio or create a place to call home.

Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)

Listing Agent: Scott Fader (248-294-7850)

Remarks: OWNER FINANCING AVAILABLE ~ LAKEFRONT 3 BEDROOM / 2 BATH HOME WITH PICTURESQUE OPEN WATER VIEWS AND PRIVATE 30 FT DOCK! Located directly on Lake Pansy in the gated subdivision of Hartridge Hills, a quaint lakefront community of approximately 60 homes. NEWER ROOF 2022 and NEWER GENERAC GENERATOR 2020. Lot size is 150 X 83 ft directly on Lake Pansy. Additional lot size in records of 2.44 acres includes riparian or water rights into the lake. Beautiful stone working fireplace with vaulted ceiling in the great room. Spacious kitchen with plenty of storage and breakfast area overlooking tranquil water views. Home was originally constructed with 2,247 sq ft and later the expansive back porch was enclosed bringing the total to 2,958 sq ft of air-conditioned living space under roof. Large windows and sliding glass doors frame panoramic vistas, infusing the space with a sense of tranquility and connection to nature. Attached 2-car garage with large storage room. HOA fees include lawn care, trimming and fertilizer to give you more time to relax. Access to Lake Hartridge and the ‘Chain of Lakes’, a navigable canal system connecting 15 lakes, is obtained from the private community boat ramp and dock. This community is well known and desired by aircraft owners and flying enthusiasts as it is near Gilbert Field-Winter Haven Regional Airport, a city-owned airport that supports over 80,000 flights a year. It is also home to the Jack Brown Seaplane Base renowned as the largest and one of the oldest seaplane training and base operations in the world. Conveniently located between Orlando and Tampa with great attractions, waterfront restaurants, shopping, and some of the best fishing and ski lakes available! Welcome home to endless days of sunshine and relaxation. Please see the interactive 3D virtual tour and floor plan. Virtually staged photos are included.

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

Listing Agent: Kay Szinegh (813-918-0624)

Remarks: Welcome to 239 Sunfish Dr, a 4-bedroom, 2-bath home in one of Winter Haven’s growing communities, offering modern comfort, thoughtful upgrades, and outdoor spaces designed to be enjoyed year-round. Built in 2021 and offering nearly 2,000 square feet of living space, this home is move-in ready and packed with value for homeowners and investors alike. Inside, you’ll find a spacious open-concept layout with a split-bedroom floor plan that offers both functionality and privacy. The kitchen opens seamlessly to the main living and dining areas, creating the perfect flow for everyday living and entertaining. With four full bedrooms, there is plenty of space for a growing household, guests, or a home office setup. What truly sets this home apart is the outdoor living experience. Enjoy a fully screened-in back porch, perfect for relaxing in the evenings without worrying about bugs, plus an extended outdoor living area ideal for grilling, gathering, or simply unwinding. A custom paver walkway leads to a charming gazebo, creating the perfect shaded retreat to enjoy the outdoors while staying out of the Florida sun. Whether you're hosting friends or enjoying a quiet morning coffee, this backyard was designed to be used and enjoyed. Additional upgrades include a full gutter system for added function and protection, helping direct water away from the home and adding peace of mind during Florida’s rainy season. Located in a growing area of Winter Haven with convenient access to shopping, dining, schools, and major roadways, 239 Sunfish Dr offers the perfect blend of newer construction, smart upgrades, and comfortable Florida living. Whether you're looking for your next home or a strong long-term investment, this one is easy to love.

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

Listing Agent: Noah Stevens (863-400-1172)

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: 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: Under contract-accepting backup offers. Short Sale. ***SHORT SALE*Discover Your Dream Home at Lakeside Landing! Welcome to this immaculate home in the picturesque community of Lakeside Landing! This property offers the ultimate in modern living, combining comfort, style, and functionality. It's move-in ready and equipped with smart home technology, energy-efficient windows, and SOLAR PANELS to help you save on energy costs. Plus, enjoy the privacy of having no rear neighbors and a fully fenced large yard. Recent Upgrades and Features Flooring: Experience the elegance of luxury vinyl flooring throughout the home, with upgraded plush carpeting in the primary bedroom. The bathrooms boast stylish tile flooring. Bathroom Updates: Enjoy the convenience of brand-new toilets and an updated guest bathroom that features a new vanity and mirror. Kitchen Enhancements :Crown molding on kitchen cabinets Added cabinet hardware, Stunning new backsplash, Farm-style door leading to the pantry New wooden pantry shelves Additional Interior Features: Ceiling fans in both the primary bedroom and living area Neutral color scheme with fresh, whole-house interior paint Outdoor Living Relax and unwind on your screened-in porch while overlooking your spacious, fenced yard. It's the perfect spot for enjoying a morning coffee or evening gatherings with friends and family. Community Amenities Lakeside Landing offers a variety of community features to enhance your lifestyle, including: Resort-style pool: Dive into relaxation and enjoy the sun by the pool. Ideal Location Convenience is at your doorstep with easy access to major highways like 27 and I-4. Nearby attractions include Legoland, Disney World, and Universal Studios, making this home an ideal location for entertainment enthusiasts. Additionally, Posner Park is just around the corner for all your shopping needs. Don't miss the opportunity to make this like-new, energy-efficient home yours. Come check it out and experience the best of Lakeside Landing living!*CDD INCLUDED IN TAXES . OWNER MOTIVATED

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Brenda Anglada (407-493-3464)

Remarks: This dynamically unique home in Winter Haven offers waterfront living, with direct access to the renowned Chain of Lakes. Ideally situated on Lake Cannon, the property delivers stunning water views and a peaceful setting that’s hard to match. Located within a gated, low-maintenance community, this home allows you to enjoy all the perks of ownership without the added upkeep. The community pool and hot tub sits just steps away—offering the feel of a personal pool without the responsibility. Residents also enjoy access to a community dock with first-come, first-served boat slips, making it easy to embrace the lake lifestyle. The property itself features a fenced yard, and a beautiful pergola—perfect for relaxing, entertaining, or enjoying the serene lakefront setting. The garage is equipped with a 2021 split-unit AC system, creating a versatile space ideal for a workshop, gym, or even additional living area. For added peace of mind, the home includes a gas-powered generator that automatically kicks on when needed. Inside, the home is nothing short of impressive—boasting soaring cathedral ceilings, expansive balconies with breathtaking views, and a layout that is both majestic and thoughtfully designed. The primary suite is a true retreat, featuring a private balcony, dual vanities, and a luxurious soaking tub designed for relaxation. Additional office and bonus spaces offers flexibility and can easily be converted into extra bedrooms to fit your needs. Updates include two AC units installed in 2017, along with a durable metal roof added in 2021 and the roof tiles were sealed and coated for an extra long life. Whether you’re looking for a full-time residence, a seasonal getaway, or a place to gather with family and friends, this home delivers a warm, inviting atmosphere with unique architectural character throughout. Enjoy peaceful mornings overlooking the lake, afternoons gardening in your yard, or evenings unwinding on the balcony while taking in the surrounding wildlife. Conveniently located near shopping, grocery stores, and Home Depot, this is more than just a home—it’s a lifestyle. A property like this must be seen in person to truly appreciate the grandeur and exceptional living experience it offers.

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

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