Winter Haven Homes under $400,000

Winter Haven Homes under $400,000

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County. Known for its picturesque lakes and vibrant community, Winter Haven offers a unique blend of small-town charm and modern conveniences. With over 50 lakes, including the stunning Chain of Lakes, residents enjoy a variety of outdoor activities, from boating and fishing to hiking and biking along scenic trails. The city's warm climate and abundant sunshine make it a year-round paradise for outdoor enthusiasts.

Winter Haven is not just about natural beauty; it also boasts a rich tapestry of culture and entertainment. The historic downtown area is filled with delightful shops, trendy restaurants, and local art galleries, providing a perfect backdrop for leisurely strolls. Families will appreciate the excellent schools, parks, and recreational facilities that contribute to a welcoming community atmosphere.

For homebuyers seeking affordable options, Winter Haven is a hidden gem. With a variety of homes available under $400,000, potential buyers can find their dream home without breaking the bank. From cozy single-family homes to charming townhouses, there’s something for everyone. Many properties feature spacious yards, modern amenities, and proximity to schools and shopping, making them perfect for families or first-time buyers.

Whether you’re looking for a serene lakeside retreat or a vibrant community to call home, Winter Haven has it all. Explore the possibilities and discover why so many people are choosing to make Winter Haven their home sweet home!

Newest Winter Haven Homes under $400,000

1096 Carefree Cove Drive, Winter Haven
$199,000
4 Beds ⋅ 2 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
**PRICED TO SELL! 4 BEDROOMS, 2 BATHROOMS, NO HOA, AND MAJOR UPDATES ALREADY COMPLETED! ** Don't miss this fantastic opportunity to own an affordable home in Winter Haven! This spacious 4-bedroom, 2-bathroom home offers plenty of potential with several major improvements already taken care of, including a **NEW ROOF IN 2022, COMPLETE REPIPE IN 2023, AND NEW WINDOWS IN 2023!** While the home could benefit from some cosmetic updating and personal touches, the big-ticket improvements have already been completed, giving the next owner a great head start. Enjoy the freedom of **NO HOA** and a convenient location near shopping, dining, schools, and major roadways. Whether you're a first-time homebuyer looking to build equity, a buyer wanting to make a home their own, or an investor searching for their next opportunity, this property checks all the boxes! **PRICED EXTREMELY COMPETITIVELY TO REFLECT THE COSMETIC UPDATES NEEDED AND SELL QUICKLY!** Opportunities like this don't come around often at this price point. Schedule your showing today and see the potential for yourself!

1096 Carefree Cove Drive, Winter Haven
221 Mandolin Drive, Winter Haven
$330,000
4 Beds ⋅ 2 Baths ⋅ Mandolin SubDv. ⋅ 33884 Zip Code
LIKE NEW!!! Don't miss this 4 bedroom, 2 bath home centrally located in Winter Haven, FL in the GATED COMMUNITY OF MANDOLIN. So many NOTABLE UPDATES in 2026 including: NEW ROOF, NEW LEVEL 3 GRANITE IN KITCHEN AND BOTH BATHROOMS, NEW SINKS, NEW KOHLER TOILETS, NEW FIXTURES, NEW INTERIOR PAINT, NEW FANS, NEWLY FINISHED GARAGE FLOOR, AND NEWLY LANDSCAPED LAWN! This OPEN CONCEPT, SPLIT PLAN is light and bright and very inviting. The OVERSIZED LOT gives you plenty of room with a length of (125 ft deep and 92 feet in width). This neighborhood is COMPLETELY BUILT OUT and VERY ESTABLISHED. The kitchen features STAINLESS APPLIANCES and is perfect for entertaining guests with it's central location. The back area is COMPLETELY PRIVATE with vinyl fencing for all your friends/family gatherings. Shopping, medical, restaurants, and LEGOLAND, FL are within minutes of this centrally located home with so many updates!!!

221 Mandolin Drive, Winter Haven
241 Volusia Drive, Winter Haven
$339,900
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Mariam Unit SubDv. ⋅ 33884 Zip Code
Timeless charm, exceptional living space and an established SE Winter Haven location! Welcome to 241 Volusia Drive, a beautifully maintained, one-owner, 3 bedroom, 2 bath residence offering 2,273 square feet of living area. From its undeniable curb appeal and mature landscaping to its classic traditional architecture, this home makes a wonderful first impression, with the added freedom of no HOA. Providing valuable peace of mind are several significant improvements, including a remodeled guest bath (2024), 5-ton A/C (2022), new roof (2019), tankless water heater (2017), remodeled kitchen, private 4" irrigation deep well for added efficiency. Beyond these thoughtful improvements, the inviting layout is equally impressive. The home opens to an expansive interior with room to comfortably accommodate both everyday living and entertaining. Just off the welcoming front entry, formal living and dining rooms provide inviting settings for holiday celebrations and memorable gatherings with family and friends. A spacious 16' x 27' family room features tile flooring, wraparound sliding windows and an abundance of natural light. With plenty of room for multiple seating arrangements, weekend sports or relaxing evenings, this is truly a space designed to be enjoyed. Convenient access to the backyard allows for an effortless transition between indoor and outdoor enjoyment. The beautifully updated kitchen features custom cabinetry with a rich wood finish, granite counters, a breakfast bar, double ovens, a flat-top range and pull-out cabinet drawers. A pantry offers additional storage, while the eat-in dinette provides a comfortable setting for casual dining. Designed with privacy in mind, the primary suite is thoughtfully separated from the guest bedrooms and features a generously sized walk-in closet and an ensuite bathroom with dual sinks and a tiled walk-in shower. Both guest bedrooms are comfortably sized with ample closet space and convenient access to the beautifully remodeled guest bathroom, updated with attractive tile finishes, a stunning vanity with a quartz counter, updated fixtures, new lighting and mirror. An interior laundry room with built-in ironing board, cabinetry and a utility sink adds everyday convenience. The oversized, side entry two car garage is another standout feature, offering abundant space for vehicles, hobbies and storage, along with built-in cabinetry and attic access. Step outside to discover a lush, fully fenced backyard framed by mature landscaping and majestic Oak trees. The fully fenced backyard offers plenty of room for family, pets and outdoor activities. A concrete patio is the perfect place for grilling or simply enjoying the peaceful surroundings. Additional highlights include double paned windows, crown molding, rain gutters and more. The location is equally appealing! Situated in an established neighborhood, this home enjoys the charm of a traditional Florida community, where mature trees nd spacious yards create a welcoming atmosphere reminiscent of years gone by. Enjoy convenient access to shopping, dining, medical facilities, schools, lakes and recreational opportunities that make Winter Haven such a wonderful place to call home. Lovingly maintained by its original owner, thoughtfully updated and ideally located, 241 Volusia Drive offers the kind of timeless appeal, comfortable living and neighborhood charm that never goes out of style. Schedule your private showing today.

241 Volusia Drive, Winter Haven
2303 Jagger Lane, Winter Haven
$355,000
4 Beds ⋅ 2 Baths ⋅ Sutton Preserve SubDv. ⋅ 33880 Zip Code
Virtually Staged. Move-in ready and built in 2024! This beautifully maintained 4-bedroom, 2-bath home offers nearly 1,900 sq. ft. of thoughtfully designed living space with an open-concept layout and desirable upgrades throughout. The spacious kitchen features quartz countertops, stainless-steel appliances, a large center island, and pantry, opening seamlessly to the living and dining areas. Tile flooring enhances the main living spaces, with carpet in the bedrooms. Additional features include an epoxy-finished garage floor, rain gutters, security cameras that convey, and solar panels. Enjoy Florida living on the enclosed screened lanai, complete with roll-down shades and patio furniture that convey, overlooking a fully fenced backyard. Located just minutes from Lake McLeod and a public boat dock, with convenient access to shopping, dining, schools, and major roadways. No CDD, low HOA fees that include high-speed internet, and a seller-provided one-year home warranty! A wonderful opportunity to own a move-in-ready home with valuable upgrades already in place. Schedule your private showing today!

2303 Jagger Lane, Winter Haven
6685 Briarhill Drive Ne, Winter Haven
$164,900
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates SubDv. ⋅ 33881 Zip Code
Welcome to Lake 'n Golf Estates, a 55+ lakefront community where YOU OWN THE LAND! No lot rent, no land lease, and an incredibly affordable HOA fee of just $550 annually, approximately $46/month! This beautifully upgraded, spacious double-wide manufactured home offers 1,534 sq ft of living space and 1,930 total sq ft, situated on a desirable corner lot with an oversized driveway, covered carport, enclosed Florida room, and additional bonus room and storage area What truly sets this property apart is the extensive list of improvements and upgrades completed by the current owners, offering tremendous value and peace of mind to the next homeowner. Major improvements include a NEW 2024 ROOF, NEW 2024 AIR CONDITIONING SYSTEM, whole-house DOUBLE-PANE WINDOWS including the sliding glass door, an upgraded 100-amp electrical panel with some new breakers, and significant plumbing improvements throughout the home. The sellers have invested in both the beauty and functionality of this property, a new induction stove, overhead range hood, garbage disposal, odor humidity fans in bathroom, updated bathroom vanities, new bathroom sinks and faucets, shower heads, toilets, interior doors, door hardware, ceiling fans, lighting, smoke detectors, and beautiful new baseboards throughout. Fresh interior paint, updated window coverings, and attractive plank flooring enhance the home's welcoming atmosphere. The spacious kitchen provides abundant cabinetry and counter space, while the open living and dining areas provide an inviting setting for entertaining family and friends. A convenient bar/coffee area with a newly installed sink adds another wonderful feature for gatherings . The large primary suite features a walk-in closet and private bathroom, a california king fits in this room comfortably, while the 2nd bedroom has its own bathroom access. There is an enclosed sunroom, featuring updated flooring, fresh paint, and blackout curtains. Beyond the cosmetic improvements, the owners have also addressed important exterior maintenance and drainage needs, including a French drain system, driveway drains, a new sump pump beneath the home, upgraded exterior plumbing with a convenient water shutoff valve, four new outdoor faucets, rebuilt rain gutters, new access beneath the home, additional ventilation turbines, landscaping, and a new mailbox and exterior lantern. A four-point inspection was completed in February 2025, adding to the property's documented maintenance history. And the lifestyle is just as impressive as the home! Lake 'n Golf Estates offers residents a heated community swimming pool, relaxing hot tub, clubhouse, shuffleboard courts, golf-cart-friendly streets, and community boating amenities with access to beautiful Lake Henry, perfect for fishing and enjoying Florida's waterfront lifestyle. Conveniently located near shopping, restaurants, medical facilities, Highway 27, and major Central Florida attractions, this community offers an appealing combination of recreation, convenience, and affordability. With DEEDED LAND, LOW ANNUAL HOA FEES, extensive upgrades, generous living space, and outstanding community amenities, this home presents an incredible opportunity to enjoy the Florida retirement lifestyle without the burden of expensive monthly lot rent. All appliances inclued and furnishings may be negotiable. Don't miss the opportunity to make this beautifully improved home your own and start enjoying everything Lake 'n Golf Estates has to enjoy!

6685 Briarhill Drive Ne, Winter Haven
2470 Salzburg Loop, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Vienna Square Ph 01 SubDv. ⋅ 33884 Zip Code
Virtually Staged. This property is located in one of the best neighborhoods in Winter haven. A new roof will be installed soon.

2470 Salzburg Loop, Winter Haven
2050 San Marcos Drive Se Unit 211, Winter Haven
$155,000
2 Beds ⋅ 2 Baths ⋅ Park Lake 03 02 Amd SubDv. ⋅ 33880 Zip Code
This 2-bedroom, 2-bath condo located in the heart of Winter Haven is ready for you to make it your home. This unit features carpet and ceramic tile throughout the unit, large family room with fireplace overlooking the pool and baseball fields, and galley kitchen with a pass thru to the dining area. Community features include pool and clubhouse that overlook the newly renovated baseball complex and a community deed on the Lake Lulu of the Chain of Lakes. Located close to many restaurants, shopping, walking trails, this one truly is all about location! Call, text, or email to see it today!

2050 San Marcos Drive Se Unit 211, Winter Haven
260 Greenfield Road, Winter Haven
$349,900
3 Beds ⋅ 2 Baths ⋅ Cypresswood Greenfield Village SubDv. ⋅ 33884 Zip Code
Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed private POOL deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle.Tucked away on the golf course with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando International Airport, and the gulf-side beaches of Tampa/St. Pete! Schedule your private showing today, and don't miss the opportunity to make this incredible home yours.

260 Greenfield Road, Winter Haven
100 El Camino Drive Unit 103, Winter Haven
$59,000
1 Beds ⋅ 1 Baths ⋅ Orchid Spgs Vill 100 Condo SubDv. ⋅ 33884 Zip Code
Clean and move in Ready condo on ground floor. This is part of an estate and ready for immediate sale. No probate will be required. The bedroom features and walk in closet. Great location that is great for year round living or a seasonal escape in a very well maintained community.

100 El Camino Drive Unit 103, Winter Haven
1550 11th Street Ne Unit B3, Winter Haven
$142,500
2 Beds ⋅ 2 Baths ⋅ Lake Buckeye Condo SubDv. ⋅ 33881 Zip Code
The property you are inquiring about is located in Winter Haven, FL, in the Lake Buckeye area of Polk County. This is an incredible value on this ground-level condo at Lake Buckeye. Near PSC, this is a fabulous investment for private or income use. The home features 2 bedrooms, 2 bathrooms, 1,148 sq.ft. living utilized efficiently and within walking distance to the lake. Personable HOA fees to include community pool/ maintenance, maintenance exterior/grounds, clubhouse, fishing, etc. This is a fantastic location for convenience. Call, text, email - ready to move into!

1550 11th Street Ne Unit B3, Winter Haven
5385 Hogan Lane, Winter Haven
$369,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code
Welcome to this stunning Biscayne-model home located at 5385 Hogan Lane, Winter Haven, Florida 33884, within the highly desirable Lake Ashton, a Premier Florida Retirement community in Central Florida. This beautifully maintained property offers premium upgrades, functional spaces, picturesque lake views and gorgeous Florida sunsets. Premium Interior Features include: Gourmet Kitchen with 42" cherry cabinetry with modern crown molding and large metal handles, granite countertops, a breakfast bar, an elegant tile backsplash, and window above the sink. The kitchen cabinet layout includes several banks of drawers, a stainless steel sink and an enlarged open area that flows seamlessly into the breakfast nook. The dedicated den is a highly functional space complete with a built-in Murphy bed and custom desk complex, perfect for a home office or guest room. The wall unit also has a desk that folds out easily. The Primary Suite Bath features comfort height cabinetry, granite countertops, upgraded mirrors and lighting fixtures, a garden tub, and a glass shower door enclosure. The guest bathroom is similarly appointed with a comfort height cabinet, granite counter, upgraded mirrors, and a shower/tub combo. You'll find Upgraded Flooring in the main living, dining, and dinette areas with bamboo flooring, while the kitchen, bathrooms, laundry room and den have tile flooring; plush carpeting is in the bedrooms. This home has a desirable outdoor living area. Relax on the large, screened lanai with tile floor while enjoying beautiful water views and sunsets. A professionally laid paver walkway connects the garage directly to the lanai. This home has double-paned windows, solar tubes for abundant natural light throughout the kitchen, bathrooms, laundry room, and den, and ceiling fans in every room. The Expanded Garage Space is a bonus. The generous double car garage has built-in cabinetry, an extra-long dedicated golf cart garage (8'5x29'11), a utility sink, an exterior window, and a pull-down ladder for attic storage. Additional Home Highlights: Roof Replaced 2025, A/C (2017), Separate Irrigation Meter, Extended Birdcage with Tile Flooring. Located in Lake Ashton, a Florida Retirement community offering Resort style amenities and planned activities. Lake Ashton, a 55 community in Florida, has (2) 18- Hole Golf Courses, Pro Shop, Main Clubhouse with Movie Theater, Bowling Lanes, Grand Ballroom, Card, Craft and Billiards, Outdoor Pool, Bocce, Shuffleboard, Tennis and Fitness Center. The Health and Fitness Center has an Indoor Pool, Card, Craft and Billiards, Multi-Purpose Room, Media Center, Indoor 1/2 Court Basketball, Indoor Full Court Racquetball, Pickle Ball courts and MORE! One Year Home Warranty Included. Call today to tour this home.

5385 Hogan Lane, Winter Haven
128 Lagoon Road, Winter Haven
$340,000
4 Beds ⋅ 2 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
This charming and move-in-ready 4-bed, 2-bath, 2-car garage home offers a blend of modern upgrades and comfortable living spaces. The renovated kitchen features quartz countertops, an oversized copper sink, and abundant storage—perfect for cooking, hosting, or everyday convenience. Throughout the home, new light fixtures add a fresh, stylish touch, and with no carpet, the tile and laminate flooring make maintenance a breeze. The spacious primary bedroom includes direct access to the screened porch, creating a relaxing indoor-outdoor retreat. The remodeled primary bathroom showcases modern finishes and thoughtful design. Step outside to a fully fenced backyard with room for outdoor furniture, gardening, or a future shed. Major updates provide peace of mind, including a new roof (2024) and new plumbing. Located in a quiet neighborhood close to parks, lakes, dining, and everyday conveniences, this home offers comfort, style, and an ideal location for easy living.

128 Lagoon Road, Winter Haven
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