Winter Haven Homes under $250,000

Winter Haven Homes under $250,000

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County. Known for its picturesque lakes and vibrant community spirit, Winter Haven is a hidden gem that offers a perfect blend of tranquility and excitement. With over 50 lakes, including the famous Chain of Lakes, residents enjoy a wealth of recreational opportunities, from boating and fishing to serene lakeside picnics. The city's rich history is evident in its historic downtown, where you can find quaint shops, delightful cafes, and local art galleries that showcase the talent of the community.

For those seeking an affordable place to call home, Winter Haven boasts an impressive selection of homes priced under $250,000. Whether you're a first-time homebuyer, a growing family, or looking to downsize, this vibrant city has something for everyone. You can find charming single-family homes, cozy townhouses, and even some delightful condos that fit your budget without sacrificing comfort or style.

Living in Winter Haven means embracing a lifestyle filled with outdoor adventures, community events, and a welcoming atmosphere. The city hosts various festivals throughout the year, including the popular Winter Haven Water Ski Show, which brings together residents for a day of fun and entertainment. Additionally, with its convenient location between Orlando and Tampa, Winter Haven offers easy access to major attractions, shopping, and dining options.

Discover the beauty and affordability of Winter Haven, where your dream home awaits! Come experience the warmth of this community and find your perfect piece of paradise today.

Newest Winter Haven Homes under $250,000

183 Osprey Heights Drive, Winter Haven

183 Osprey Heights Drive, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Osprey Landings SubDv. ⋅ 33880 Zip Code

Virtually Staged. Welcome to this inviting 3-bedroom, 2-bathroom home nestled in the serene gated community of Osprey Landing in Winter Haven, offering comfortable living spaces, attractive landscaping, and excellent outdoor living. The bright living room features high vaulted ceilings, a ceiling fan, architectural cutouts, easy-care flooring, and direct access to the private screened-in patio, creating an easy flow between indoor and outdoor living. A BRAND NEW ROOF installed in 2025 adds value and peace of mind The kitchen offers white cabinetry, a double-basin sink, pantry closet, and convenient eating space. The primary bedroom features an ensuite bathroom and walk-in closet, while two additional bedrooms provide flexibility for guests, a home office, or hobbies. One of the bathrooms has been completely remodeled, adding an updated touch to the home's interior. Outside, enjoy the expansive FULLY FENCED backyard. The screened patio overlooks the spacious landscaped yard and offers an ideal setting for relaxing, entertaining, pets, or outdoor activities. A shaded front lawn and mature oak tree enhance the curb appeal, while the 2-car garage provides convenient parking and storage. Located in Winter Haven’s desirable Chain of Lakes area, this home is close to lakes, parks, recreation, shopping, restaurants, and downtown Winter Haven, with convenient access to major roads connecting to Lakeland, Auburndale, and surrounding communities. Central Florida attractions such as LEGOLAND Florida and Walt Disney World are also within an easy drive, making this a wonderful opportunity to enjoy peaceful gated-community living while remaining close to everyday conveniences and entertainment.

183 Osprey Heights Drive, Winter Haven

113 Nemo Lane, Winter Haven

113 Nemo Lane, Winter Haven

3 Beds ⋅ 3 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code

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.

113 Nemo Lane, Winter Haven

444 Avenue I Se, Winter Haven

444 Avenue I Se, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Pine Crest Heights SubDv. ⋅ 33880 Zip Code

INVESTOR OPPORTUNITY with recent systems updates! The costly systems have been updated at this 2-bedroom, 2-bath home at 444 Avenue I SE in Winter Haven: Roof (2025), HVAC (2023), Water Heater (2023), and Plumbing (2023, all except the kitchen). The electrical wiring in the demoed bathroom was also updated in 2023. With these recent updates, more of your renovation budget can go toward finishes and value-adding improvements. Offering approximately 1,036 square feet of living space on a 75 x 140 lot in an established neighborhood close to downtown. Inside, hardwood floors, a wood-burning fireplace, and separate living and dining areas provide character and a solid starting point for your renovation plans. The spacious yard offers room to enjoy the outdoors, while a detached shed provides additional workshop and storage space. No HOA. Located approximately one mile from downtown Winter Haven, the home offers convenient access to Central Avenue's shopping and dining and the historic Ritz Theatre. Winter Haven Hospital and Polk State College's Winter Haven campus are also nearby. Enjoy the area's lakes and outdoor recreation, including South Lake Howard Nature Park, with additional shopping and dining along Cypress Gardens Boulevard and LEGOLAND Florida Resort within driving distance. The home requires repairs and renovation, and is being sold strictly AS-IS. CASH OR HARD MONEY FINANCING ONLY. An opportunity to bring new life to a property with updated systems, character, outdoor space, and proximity to Winter Haven's amenities. Seller makes no representations or warranties regarding condition, square footage, zoning, permitted uses, or future development potential. Buyer and buyer's agent are responsible for conducting their own due diligence. The roof has a hole and requires repairs.

444 Avenue I Se, Winter Haven

6619 Westchester Drive Ne, Winter Haven

6619 Westchester Drive Ne, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates SubDv. ⋅ 33881 Zip Code

Welcome to Lake 'n Golf Estates, a desirable 55+ lakefront, no-pet community offering a wonderful location and relaxed Florida lifestyle! This VERY WELL-MAINTAINED 2-bedroom, 2-bathroom home offers over 1,600 sq. ft. of living space, including a BEAUTIFUL and spacious Florida room under central air and heat, providing valuable additional living space. The bright, open floor plan feels spacious and inviting, while the private setting with no rear neighbors is an added bonus. The kitchen features a breakfast bar, built-in desk, plenty of cabinet and counter space, newer luxury vinyl flooring, and a replaced refrigerator and stove. The generously sized primary bedroom includes a private ensuite bathroom, while a comfortable guest bedroom and second full bathroom provide plenty of room for visitors. This home has been thoughtfully maintained and updated, including the MAIN SHINGLE ROOF APPROXIMATELY 3 YEARS OLD, A/C APPROXIMATELY 4.5 YEARS OLD, replumbing, fresh interior paint, updated blinds, recently replaced washer and dryer, and UPDATED LANDSCAPING that enhances the home's curb appeal. An additional crawlspace access panel has also been installed for easier maintenance. Additional features include an inside laundry room with built-in desk, attached carport and workshop offering plenty of space for hobbies and storage. Best of all, the home is being sold FULLY FURNISHED AND TURNKEY, just bring your suitcase and start enjoying Florida living! Lake 'n Golf Estates offers fantastic amenities including a clubhouse, pool, spa, shuffleboard and community boat slip access (upon availability), perfect for enjoying the beautiful lakefront setting. With OWNED LAND, an established and well-maintained community, and numerous updates already completed, this home offers an excellent opportunity for easy Florida living. Schedule your private showing today!

6619 Westchester Drive Ne, Winter Haven

193 E Sweet Circle, Winter Haven

193 E Sweet Circle, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code

Charming 2 bedroom, 2 bath fully furnished home where comfort meets character. This beautifully appointed residence features custom, hand crafted furniture made by the owner, adding a unique personal touch you won't find in most homes. Enjoy the convenience of a move in ready home in an active park that has many games and activities that allows you to meet and make new friends. This home is located in a welcoming community and comes with one share of Orange Manor Co-Op., giving the owner voting rights within the cooperative. Even better, enjoy the benefit of low monthly HOA fees.

193 E Sweet Circle, Winter Haven

217 Grove Ridge Drive, Winter Haven

217 Grove Ridge Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 33880 Zip Code

HELLO INVESTOR OR FIRST TIME HOME BUYER DON'T MISS THIS FANTASTIC OPPORTUNITY TO OWN YOUR OWN LAND! THIS WELL-MAINTAINED 2 BEDROOM 2 BATH DOUBLE-WIDE MANUFACTURED HOME SITS ON A SPACIOUS 0.26-ACRE OWNED, FULLY FENCED LOT, OFFERING PRIVACY AND PLENTY OF ROOM TO ENJOY THE OUTDOORS. THE HOME FEATURES A BRIGHT AND SPACIOUS LIVING AREA, A LARGE WALK-IN CLOSET IN THE PRIMARY BEDROOM, A NEW WELL WATER SYSTEM, AND RV PARKING. CONVENIENTLY LOCATED CLOSE TO EVERYTHING, THIS PROPERTY IS IDEAL FOR HOMEOWNERS OR INVESTORS SEEKING CONFORT, SPACE, AND VALUE. AGAIN NO LOT RENT. SCHEDULE YOUR PRIVATE SHOWING TODAY.

217 Grove Ridge Drive, Winter Haven

200 El Camino Unit 106, Winter Haven

200 El Camino Unit 106, Winter Haven

1 Beds ⋅ 1 Baths ⋅ Orchid Springs Vill #200 Condominuim SubDv. ⋅ 33884 Zip Code

Seller is ready to negotiate and will entertain all reasonable offers! Welcome home to this charming and spacious first-floor corner condo, offering comfort, convenience, and an inviting community lifestyle. With 1 bedroom, 1 bathroom, and 1,078 square feet of living space, this home offers more room than you might expect. As a corner unit, it offers a comfortable sense of privacy, while its convenient location near the mailboxes and elevators makes everyday living a little easier. The condo also features a stackable washer and dryer conveniently located inside the bathroom. The Florida room provides wonderful additional space and opens toward the community garden area. The current seller is using the Florida room for storage, but this versatile space could easily be transformed into a cozy sitting area, reading nook, hobby space, or simply a peaceful place to enjoy your morning coffee. Enjoy the Florida lifestyle without having to leave home! The community offers a refreshing pool and clubhouse with activities such as bingo, providing opportunities to relax, socialize, and meet your neighbors. This is a pet-friendly community for all ages, making it a welcoming place to call home. And there's even more value in the HOA fee. Water, sewer, trash, and gas are included, along with use and maintenance of the community pool, exterior pest control, and maintenance of the grounds. That's a lot of convenience wrapped into one monthly fee! The location is another plus, with shopping, restaurants, and Central Florida's famous theme parks conveniently nearby. Whether you're looking for a full-time residence, a Florida getaway, or a comfortable home in a convenient location, this condo is worth a closer look. With a seller willing to entertain all reasonable offers, don't miss your opportunity to see this condo and discover all it has to offer!

200 El Camino Unit 106, Winter Haven

1331 Haines Drive, Winter Haven

1331 Haines Drive, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Lakes At Lucerne Park SubDv. ⋅ 33881 Zip Code

Welcome to this beautiful 3-bedroom, 2-bath home in Lakes at Lucerne Park, built in 2020 and offering modern comfort, thoughtful upgrades, and beautiful lake views. This move-in-ready home features a desirable split-bedroom floor plan, vaulted ceilings, an open-concept living area, and abundant natural light. With a low HOA and NO CDD FEES, it offers both comfort and value. The upgraded kitchen is designed for everyday living and entertaining, featuring granite countertops, upgraded cabinetry, stainless steel appliances, a center island with breakfast-bar seating, a corner pantry, a convenient coffee bar, and a separate eating area. Tile flooring extends throughout the main living spaces, while the bedrooms are comfortably carpeted. The spacious primary suite includes a large walk-in closet and a private bath with a walk-in shower. The guest bathroom features an extra-deep tub. Sliding glass doors lead to a screened-in lanai overlooking the beautiful lake, creating a peaceful setting for morning coffee, evening relaxation, or entertaining guests. The stunning lake views can be enjoyed from the lanai and backyard, offering a serene backdrop to everyday living. The lanai TV is included. The fully fenced backyard, combining chain-link and white vinyl fencing, provides privacy while allowing you to take full advantage of the picturesque waterfront setting. Additional highlights include a 2025 AC, exterior paint completed in July 2025, 15-year warranties on both the roof and windows, and a washer and dryer that convey with the home. The garage entry also features a screened door, providing added ventilation and convenience. Located in the heart of Winter Haven's Chain of Lakes, Lakes at Lucerne Park offers convenient access to lakes, conserved natural areas, biking and walking trails, golf courses, shopping, dining, parks, recreation, and nearby attractions including historic Bok Tower Gardens. With newer 2020 construction, beautiful lake views, a fully fenced yard, screened outdoor living, an upgraded kitchen, newer AC, and valuable roof and window warranties, this home offers an exceptional combination of comfort, convenience, and peace of mind. Come see for yourself how beautifully this home blends comfortable living with peaceful lake-view living!

1331 Haines Drive, Winter Haven

2426 6th St Ne, Winter Haven

2426 6th St Ne, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Smart Sub Pb 10 Pg 10 SubDv. ⋅ 33881 Zip Code

There’s something special about being the first person to call a house home. At 2426 6th Street NE in Winter Haven, this 2026 new-construction home offers a fresh start without the projects, deferred maintenance, or dated finishes that often come with resale properties. It also includes a 2-10 builder warranty for added peace of mind. Inside, the home feels bright, clean, and easy to live in. Wood-look flooring, neutral finishes, and recessed lighting create a modern backdrop that is easy to personalize. The kitchen stands out with white shaker cabinetry, granite countertops, stainless-steel appliances, and plenty of workspace for everyday cooking and entertaining. The layout makes excellent use of its 1,447 square feet of living area, with three bedrooms and two bathrooms designed around everyday functionality. The primary suite includes its own private bath and closet space, while the secondary bedrooms can easily serve as guest rooms, office space, or additional bedrooms. Outside, the fully fenced backyard is one of the home’s best features. There is room for pets, cookouts, gardening, outdoor games, or simply enjoying your own private piece of Florida. The covered rear patio adds a shaded place to relax, enjoy morning coffee, or unwind at the end of the day. With approximately 1,662 total square feet under roof, this home offers a practical combination of new construction, modern finishes, outdoor space, and warranty protection. For buyers looking for a new construction home in Winter Haven, this one delivers something increasingly valuable: a clean slate, a functional layout, and the opportunity to make it your own from day one.

2426 6th St Ne, Winter Haven

200 El Camino Drive Unit 102, Winter Haven

200 El Camino Drive Unit 102, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Vill 200 Condo SubDv. ⋅ 33884 Zip Code

MOTIVATED SELLER! Welcome to this spacious 2-bedroom, 2-bath condo in desirable Orchid Springs. This well-designed home features a split floor plan, walk-in closets in both bedrooms, and a private en-suite bath in the primary bedroom. Relax in the Florida room while enjoying peaceful views of lush greenery, the lagoon, and a gently flowing fountain. The community offers a pool, clubhouse, and assigned parking conveniently located near the unit. The building has been re-plumbed, and the roof was recently replaced. Ideally located near LEGOLAND, shopping, dining, medical, and everything Central Florida has to explore. Whether you’re looking for a full-time residence or a relaxing Florida retreat, this condo is ready for its next owner. Schedule your private showing today!

200 El Camino Drive Unit 102, Winter Haven

828 30th Street Nw, Winter Haven

828 30th Street Nw, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Westwood Sub SubDv. ⋅ 33881 Zip Code

MOVE-IN-READY 3-BEDROOM, 2-BATH HOME ON A 0.31-ACRE DOUBLE LOT WITH A 2026 ROOF, NEW SEPTIC SYSTEM, AND NO HOA IN WINTER HAVEN! Cosmetic updates include new flooring, fresh paint, refreshed bedrooms and bathrooms, and an updated kitchen with new cabinets, countertops, and appliances. Additional improvements include a water heater replaced within the last few years. The double lot offers plenty of outdoor space for gardening, entertaining, or enjoying the Florida sunshine. Located near Lake Howard, Lake Cannon, and Downtown Winter Haven’s dining, shopping, and entertainment, with access to the Chain of Lakes for boating, fishing, and waterfront recreation. Convenient access to US-17 and US-92 connects you to Auburndale, Lakeland, and surrounding Central Florida destinations. FHA, VA, conventional, USDA financing, and cash offers welcome. Square footage is owner provided. Buyer to verify square footage and all measurements. Schedule your showing today!

828 30th Street Nw, Winter Haven

2352 Isle Royale Court Se, Winter Haven

2352 Isle Royale Court Se, Winter Haven

2 Beds ⋅ 3 Baths ⋅ Townhouses At Park Lake 01 Rep SubDv. ⋅ 33880 Zip Code

This inviting two-bedroom, two-and-a-half-bath townhouse in Winter Haven, Florida, offers comfortable living, convenient amenities, and an exceptional walkability! Enjoy easy access to banks, grocery stores, retail shops, and a variety of restaurants, making everyday errands and dining out wonderfully convenient. Inside, the home features new luxury vinyl plank flooring, providing a fresh, modern look that is both stylish and easy to maintain. The thoughtfully designed two-story layout offers two spacious bedrooms upstairs, each with its own private bath, plus a convenient half bath for guests downstairs. The primary bedroom features a lovely screened in balcony! There is also a very spacious screened in porch off of the living room, perfect for enjoying a beverage while relaxing! A one-car garage provides secure parking and additional storage, while the community amenities add to the appeal. Residents can enjoy a community pool and dock, perfect for relaxing, enjoying the Florida sunshine, or taking in the peaceful surroundings. Located close to the new walking trail behind the Advent Fieldhouse which also offers tons of recreational activities! Whether you're looking for a full-time residence, a low-maintenance Florida home, or an investment opportunity, this townhouse combines comfort, convenience, and an excellent location in the heart of Winter Haven.

2352 Isle Royale Court Se, Winter Haven

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