Winter Haven Homes under $350,000

Winter Haven Homes under $350,000

Welcome to Winter Haven, Florida, a hidden gem nestled in the heart of Polk County! Known for its stunning chain of lakes, vibrant community, and charming downtown area, Winter Haven offers an idyllic setting for families, retirees, and everyone in between. With its warm climate, abundant recreational opportunities, and a rich history, it's no wonder that Winter Haven is becoming a sought-after destination for homebuyers.

One of the most appealing aspects of Winter Haven is the availability of beautiful homes under $350,000. Whether you’re a first-time homebuyer, looking to downsize, or seeking an investment property, the diverse real estate market here has something for everyone. From cozy single-family homes to modern townhouses, you’re sure to find a property that meets your needs without breaking the bank.

Imagine living just minutes away from the picturesque lakes, where you can enjoy boating, fishing, and picnicking with family and friends. The local parks, such as the popular Lake Howard Park, provide ample space for outdoor activities, while the downtown area boasts charming shops, delightful eateries, and a welcoming community vibe.

Winter Haven is also conveniently located near major highways, making it easy to explore nearby attractions like Legoland Florida Resort and the bustling city of Orlando. With its blend of natural beauty, affordable housing options, and a friendly atmosphere, Winter Haven is the perfect place to call home. Discover your dream home in this enchanting city today!

Newest Winter Haven Homes under $350,000

420 Avenue U Ne, Winter Haven
$155,900
3 Beds ⋅ 2 Baths ⋅ Eula Vista Sub SubDv. ⋅ 33881 Zip Code
Welcome to this charming 3-bedroom, 1.5 bathroom solid block home offering a comfortable 1,216 square feet of living space in an established, NO-HOA neighborhood. Built in 1960 and situated on a 0.14-acre lot, this property features a fully fenced front-to-back yard with a massive backyard and generous front yard. Step inside to enjoy a bright interior complemented by fresh paint, new flooring, spacious closets, convenient linen closets for extra storage, and a delightful enclosed Florida room with French doors. Major peace of mind comes with a brand-new roof installed in 2022. Perfectly positioned just minutes from local lakes, parks, recreation centers, magnet schools, and public transit, this home combines timeless character with modern updates. Schedule your showing today!

420 Avenue U Ne, Winter Haven
183 Osprey Heights Drive, Winter Haven
$189,900
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
6159 Coronari Lane, Winter Haven
$336,990
5 Beds ⋅ 3 Baths ⋅ Villamar Phase 7 SubDv. ⋅ 33884 Zip Code
Under Construction. The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a spacious living and foyer space to utilize for work or play. The primary bedroom one is located just off the loft space and features a spacious walk-in closet as well as ensuite bathroom with double vanity and all the space you need to get ready in the morning. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Villamar, the Robie includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *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.*

6159 Coronari Lane, Winter Haven
113 Nemo Lane, Winter Haven
$239,900
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
$119,000
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
2415 Brassie Court, Winter Haven
$279,000
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 3 SubDv. ⋅ 33884 Zip Code
Virtually Staged. Situated in desirable southeast Winter Haven, this EcoSmart 3-bedroom, 2-bath home offers the best of small-town living with convenient access to shopping, restaurants, Legoland, and major routes. This smart home features a Qolsys IQ Panel that allows you to check in on your home anytime, anywhere. The panel serves as the control center for the security system and allows you to manage lights, locks, thermostats, security, and more. Upon arrival, you are welcomed by a charming front porch. The spacious foyer features a coat closet, tile flooring, and a transom window. The spacious living room offers high ceilings and a glass sliding door leading to the Florida room. The eat-in kitchen features stylish gray cabinetry, a stainless steel appliance package, and a huge walk-in pantry. The center island provides convenient seating for casual dining. The open-concept floor plan offers a seamless flow between the kitchen, dining area, and living room, creating an ideal space for entertaining family and friends. The primary bedroom suite is privately located at the back of the home and overlooks the backyard. A walk-in closet provides ample storage. The primary en-suite bathroom features a comfort-height vanity with dual sinks, a linen closet, and a walk-in shower with safety grab bars. A private water closet includes a comfort-height toilet with a safety grab bar. Two additional guest bedrooms share a guest bathroom with a tub/shower combination. The Florida room features hurricane-impact windows and doors, allowing you to enjoy the outdoors even during inclement weather. Situated on a premium corner lot, this home also features an irrigation system with a rain sensor. Additional amenities include a laundry room with washer and dryer, smart front-door lock, Netatmo smart video doorbell, Honeywell smart thermostat, exterior carriage light, double-pane windows, two-car garage with garage door opener, and keyless entry pad. The lovely community of Villamar offers sidewalks, tree-lined streets, a playground, and a resort-inspired swimming pool. The seller is offering the future buyer a $5,000 credit that can be applied toward closing costs and prepaids. This exceptional home combines smart-home convenience, comfort, energy efficiency, and an excellent location.

2415 Brassie Court, Winter Haven
2433 Avenue F Nw, Winter Haven
$294,997
3 Beds ⋅ 2 Baths ⋅ Inwood SubDv. ⋅ 33880 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. VACANT AND READY FOR IMMEDIATE OCCUPANCY! Built in 2022, this attractive single-story home offers three bedrooms, two full bathrooms, a functional open layout and a two-car garage. The modern kitchen features granite countertops and a complete appliance package, while durable vinyl flooring makes everyday maintenance easy. Additional highlights include central air conditioning, a paver driveway, public water, a private septic system and no HOA. Conveniently located near shopping and dining along Havendale Boulevard, downtown Winter Haven, Winter Haven Hospital, Polk State College, local schools and the city’s popular Chain of Lakes, parks and recreational trails. Move-in ready and easy to show—schedule your private tour today!

2433 Avenue F Nw, Winter Haven
640 Avenue I Nw, Winter Haven
$325,000
3 Beds ⋅ 3 Baths ⋅ Villa Park Or Stone & Manns SubDv. ⋅ 33881 Zip Code
GREAT OPPORTUNITY to own this unique property. If you have a strong vision for remodeling and a passion for a project, this is the perfect property for you to restore to it's full potential! The main house and the duplex in the back of the property combine a total of over 3700 sq ft of living. The main house could be your residence while the duplex offers flexibility- ideal as an in-law suite, a rental income, or both. It could even be a place to live while you renovate the main house. The possibilities are endless with this fixer upper. The Location is OUSTANDING: walk to downtown, grocery stores, bus terminal, medical facilities, Hospital, restaurants, and shopping. With the RIGHT vision, this property can be used in a variety of ways and may even generate income to help cover the mortgage while using the main house as your primary residence. Please schedule your showing and contact your lender for information about a reno loan today so you don't miss the chance to own this property!

640 Avenue I Nw, Winter Haven
504 Ituna Circle, Winter Haven
$331,020
4 Beds ⋅ 2 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code
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!

504 Ituna Circle, Winter Haven
732 Bayside Boulevard, Winter Haven
$281,900
3 Beds ⋅ 2 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code
New construction home with 1,486 square feet on one-story including 3 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, pantry, and a spacious counter height bar, 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 decor do not convey."

732 Bayside Boulevard, Winter Haven
736 Bayside Boulevard, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ Harbor At Lake Henry SubDv. ⋅ 33881 Zip Code
New construction home with 1,479 square feet on one-story including 3 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, pantry, and a spacious counter height bar, 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 a tiled shower and linen closet. 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."

736 Bayside Boulevard, Winter Haven
1831 Carnostie Road, Winter Haven
$279,000
4 Beds ⋅ 2 Baths ⋅ Villamar Ph 3 SubDv. ⋅ 33884 Zip Code
Welcome home to this well maintained residence in the highly sought-after VillaMar community of Winter Haven! Built with modern energy-efficient construction and design, this home offers the perfect blend of comfort, convenience, and Florida lifestyle living. Featuring an open-concept floor plan, spacious living areas, a private owner’s suite, and a covered patio ideal for entertaining, this property is designed for both everyday living and memorable gatherings. Location is everything, and this home delivers! Situated just minutes from major transportation corridors including US Highway 27, Highway 60, and SR-17, residents enjoy quick access to Orlando, Lakeland, Tampa, and Central Florida’s growing employment centers. The community’s strategic location makes commuting simple while keeping you close to everything Winter Haven has to offer. Families will appreciate proximity to excellent area schools, including Chain Of Lakes Elementary School, Denison Middle School, and Lake Region High School. Shopping, dining, and entertainment are just around the corner with convenient access to Walmart Supercenter, local restaurants, grocery stores, medical facilities, and everyday conveniences. Residents are also minutes from Winter Haven’s famous Chain of Lakes, boating and fishing opportunities, and world-renowned attractions such as LEGOLAND Florida Resort and Peppa Pig Theme Park Florida. Community amenities and nearby nature views create a relaxed Florida atmosphere, while the home’s newer construction provides peace of mind with modern systems, energy efficiency, and low-maintenance living. Whether you’re a first-time homebuyer, growing family, seasonal resident, or investor, this property presents an exceptional opportunity in one of Winter Haven’s fastest-growing areas.

1831 Carnostie Road, Winter Haven
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