Winter Haven Homes under $400,000

Winter Haven Homes under $400,000

Welcome to Winter Haven, Florida—where sunshine meets serenity! Nestled in the heart of Polk County, Winter Haven is a charming city known for its picturesque lakes, friendly community, and vibrant culture. With over 50 lakes, including the stunning Chain of Lakes, outdoor enthusiasts will find plenty of opportunities for fishing, boating, and enjoying the beautiful Florida weather.

Winter Haven boasts a rich history, showcased through its delightful downtown area filled with boutique shops, local eateries, and art galleries. The city also hosts various events throughout the year, from lively festivals to farmer's markets, fostering a strong sense of community among residents.

For those seeking a new home in this idyllic locale, Winter Haven offers an array of options, particularly for buyers looking for homes under $400,000. The real estate market here is diverse, featuring charming single-family homes, modern townhouses, and spacious condos. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find properties that cater to your needs without breaking the bank.

With affordable housing options combined with the allure of a laid-back lifestyle, Winter Haven is an ideal place to call home. Imagine sipping your morning coffee on your porch while enjoying serene lake views or taking leisurely strolls through the local parks. Experience the warmth and charm of Winter Haven—where your dream home awaits!

Newest Winter Haven Homes under $400,000

213 Lakeside Ranch Circle, Winter Haven
$54,900
2 Beds ⋅ 1 Baths ⋅ Lakeside Ranch For Mobile Homes SubDv. ⋅ 33881 Zip Code
Have you seen Lakeside Ranch? It is a desirable 55+ community in Winter Haven. This charming 2-bedroom, 1-bath home offers the added benefit of land ownership with NO lot rent! Features include a newer roof and hurricane shutters for added peace of mind. Enjoy a relaxed Florida lifestyle with lake access and community boat ramps, perfect for boating, fishing, and enjoying the outdoors. A great opportunity for year-round living or a seasonal Florida retreat.

213 Lakeside Ranch Circle, Winter Haven
6066 Se Southern Oaks Drive, Winter Haven
$129,900
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
Morning coffee on a shaded screened porch, room for your favorite hobbies, and a community pool beside the lake. Welcome to life at Garden Grove Oaks! Located in a quiet 55+ community tucked away in the southeast Winter Haven/Garden Grove area, this 2-bedroom, 2-bath home offers the benefit of owning your land.Step inside to a dining area conveniently positioned near the kitchen, which includes a refrigerator, range, microwave, and dishwasher. Cathedral ceilings create an open, spacious feel, while ceiling fans serve the living room, kitchen, and both bedrooms. The primary bedroom includes an en-suite bathroom with a step-in shower.Two screened porches give you options for enjoying the outdoors. The front porch welcomes morning shade and a pleasant breeze, while the side porch behind the carport features tile flooring. An adjoining storage area with two workbenches provides useful space for tools, projects, and hobbies. Laundry hookups are available in an interior closet and on the screened porch behind the carport. The washer and dryer do not convey.A roof approximately two years old, vinyl siding, a carport, and a long driveway add everyday convenience. Enjoy a nicely sized backyard and an open feel to the east, where the neighboring vacant lot is owned by the next-door neighbor. Garden Grove Oaks offers shuffleboard and a pool next to the community lake, completing the setting for relaxed Florida living. Come see how this home fits your next chapter!

6066 Se Southern Oaks Drive, Winter Haven
395 San Jose Dr, Winter Haven
$170,000
2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Patio Homes SubDv. ⋅ 33884 Zip Code
Charming 2 bedroom, 2 bath home with a 1 car garage in Orchid Springs! The expansive main living space flows effortlessly into a dedicated dining area, creating a bright and airy atmosphere perfect for effortless entertaining. Slightly tucked away, the kitchen boasts ample counter space, tons of cabinets, and even a closet pantry for extra storage. The primary bedroom is located at the rear of the home, complete with its own bathroom and large closet. The laundry area can be found in the garage for added convenience. The rear screened porch, great for relaxation. Don't delay; make your appointment today.

395 San Jose Dr, Winter Haven
3944 Giorgio Drive, Winter Haven
$275,000
4 Beds ⋅ 2 Baths ⋅ Villamar SubDv. ⋅ 33884 Zip Code
Brand new, energy-efficient home available by Aug 2026! An open floorplan that makes entertaining easy in the open kitchen, dining, and great room that flow to the patio. The primary suite is tucked in the rear of the home offering plenty of privacy and features a spacious walk-in closet and shower. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

3944 Giorgio Drive, Winter Haven
7060 Fairview Village Circle, Winter Haven
$134,990
1 Beds ⋅ 1 Baths ⋅ Fairview Village SubDv. ⋅ 33881 Zip Code
Welcome Home to Easy Florida Living! Come discover this beautifully maintained 2023 Skyline Park Model, installed in August 2022 and thoughtfully designed with comfort, convenience, and relaxation in mind. From the moment you arrive, you?ll appreciate the new concrete driveway, newer roof, central air, spacious storage, and inviting outdoor living opportunities. Inside, the home offers an open and comfortable layout with a large pantry, dining island, electric fireplace, walk-in shower, and a bedroom spacious enough for a king-size bed. The home is being offered with many furnishings and features, including a French-door refrigerator, electric range, microwave, washer/dryer combo, water softener, blinds, generator ready and more. The lifestyle is just as appealing! The 99-year perpetual lease is renewable for only $1, while the current $90 monthly association fee includes water, sewer, trash, seasonal lawn maintenance, heated pool access, clubhouse, and a variety of community activities. Enjoy shuffleboard, horseshoes, billiards, ping pong, and a community dock with direct canal access to Lake Henry, complete with a pier bench and fire pit. Whether you?re looking for a seasonal retreat, a comfortable Florida getaway, or a place to enjoy the relaxed community lifestyle, this one is ready for you to come see and fall in love with it! Financing Available!

7060 Fairview Village Circle, Winter Haven
1354 Haines Drive, Winter Haven
$295,000
3 Beds ⋅ 2 Baths ⋅ Lakes/Lucerne Park Ph 6 SubDv. ⋅ 33881 Zip Code
Welcome to 1354 Haines Dr in Winter Haven—a charming, modern home that offers the comfort and convenience of newer construction without the wait. Built in 2020, this thoughtfully designed 3-bedroom, 2-bathroom home features 1,292 square feet of living space, making it an excellent option for first-time homebuyers, downsizers, or investors looking for an opportunity in Central Florida. Step inside and discover a practical layout designed for everyday living, with a combination of tile and carpet flooring that brings both functionality and comfort to the home. The open feel and efficient use of space make it easy to envision your own furniture, personal style, and everyday routines here. Outside, the stucco exterior and manageable lot of approximately 6,621 sqft appeal of a newer Florida home with outdoor space to enjoy. Whether you're looking for a place to call your own or an investment opportunity, this property offers a solid starting point in an established Winter Haven neighborhood. Conveniently located in the heart of Polk County, you'll have access to the area's shopping, dining, and everyday essentials while enjoying the Central Florida lifestyle. With its newer construction, functional floor plan, and inviting potential, 1354 Haines Dr is ready for its next chapter. Your opportunity to make it home starts here.

1354 Haines Drive, Winter Haven
306 Eagle Pond Drive Unit 306, Winter Haven
$211,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Beautiful completely updated condo in the highly desirable gated community of Cypresswood Golf and Country Club. It features tile flooring throughout the whole condo, marble kitchen countertops with an extended breakfast island, new water heater, matching marble on both bathroom vanities, upgraded lighting fixtures/ceiling fans, interior laundry with washer and dryer, pond view, and so much more. The master bedroom features an en suite bathroom while both bedrooms have a walk-in-closet. Additional linen storage exists in the main bedroom and hallway, plus an additional outside storage closet with shelves. The Cypresswood community features an 18-hole championship golf course designed by Ron Garl, junior Olympic sized community pool, lighted tennis courts, clubhouse with a restaurant, event space and more. Minutes from Hwy 27 and the I-4 corridor, Winter Haven's chain-of-lakes for the water enthusiast, Legoland Fl Park and Resort, Bok Tower gardens, and a brand new Publix shopping center within 2 miles and much more. Centrally located between Orlando and Tampa. Schedule your private showing today.

306 Eagle Pond Drive Unit 306, Winter Haven
4956 Jackson Street, Winter Haven
$295,000
4 Beds ⋅ 2 Baths ⋅ Jackson Lndg SubDv. ⋅ 33884 Zip Code
Built in 2023, this 4-bedroom, 2-bath Winter Haven home combines modern design with ultimate convenience. The bright, open-concept interior features ceramic tile floors and a chef-inspired kitchen with a large island. Relax on your screened-in lanai overlooking a private backyard. Located minutes from shopping, schools, and attractions—this move-in-ready gem is a must-see!

4956 Jackson Street, Winter Haven
503 William Avenue, Winter Haven
$269,900
3 Beds ⋅ 2 Baths ⋅ Jan Phyl Village SubDv. ⋅ 33880 Zip Code
Be the First to Enjoy This Beautifully Renovated Home! Featuring brand-new paint, flooring, kitchen, bathrooms, windows, doors and AC. This home offers modern finishes and a bright, open layout with granite countertops, new cabinetry, and stainless-steel appliances. Situated on an oversized lot in a quiet, established neighborhood with NO HOA, enjoy a spacious yard, ample parking, and plenty of room to entertain. Conveniently located near shopping, dining, and major roadways, this move-in-ready home is a must-see!

503 William Avenue, Winter Haven
1358 Buckeye Trace Boulevard, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Buckeye Trace SubDv. ⋅ 33881 Zip Code
Short Sale. SHORT SALE!! Looking for a home that offers more space without stretching your budget? This beautifully maintained 4-bedroom, 2-bath home in the gated Buckeye Trace community deserves a spot on your must-see list! With 1,820 square feet of living space, an open floor plan, updated flooring, and a two-car garage, this home offers the kind of practical, comfortable layout that makes everyday living easy. Whether you're hosting friends, enjoying a quiet evening at home, or turning that fourth bedroom into the office or hobby space you've been wanting, there's room to make it your own. And the location? That's another reason to love it! Winter Haven has so much to offer, from afternoons on the Chain of Lakes and waterfront dining to the locally owned restaurants, shops, and events in Downtown Winter Haven. LEGOLAND Florida Resort is nearby, and you'll have convenient access to shopping, schools, and everything you need for day-to-day living. Priced at $270,000, this home offers a competitive opportunity in Buckeye Trace, especially for buyers looking for four bedrooms in a gated neighborhood. It's well cared for, move-in ready, and waiting for its next chapter. This property is offered as a short sale, subject to mortgage lender approval. Don't let the short sale designation keep you from taking a look — schedule your showing and see what this home has to offer!

1358 Buckeye Trace Boulevard, Winter Haven
4043 Bedford Avenue, Winter Haven
$359,900
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
UPGRADED HOME IN THE GATED RESORT-STYLE COMMUNITY OF TRADITIONS: Meticulously maintained and thoughtfully upgraded 2 bedroom, 2 bath home with a versatile den that can easily serve as a 3rd bedroom, located in the desirable Traditions at Lake Ruby community. Enjoy comfortable living and an active lifestyle in this gated 55+ community in Winter Haven. This beautifully maintained home features extensive improvements, generous outdoor living space and transferable home warranty until April of 2030. The open floor plan brings the great room and kitchen together for easy everyday living and entertaining. New laminate flooring adds warmth, while the kitchen features quartz countertops, an island with seating and pendant lighting, stainless steel appliances including a double oven with air-frying and microwave capabilities and a closet pantry. An adjoining dinette provides a casual dining spot, while the formal dining room offers an inviting setting for intimate dinners and holiday gatherings. The spacious primary suite features a tray ceiling, a walk-in closet with custom built-ins and an ensuite bath with a quartz countertop, dual sinks, a handicap accessible walk-in shower and a private water closet. The comfortably sized secondary bedroom is conveniently situated near the guest bathroom, which features a new walk-in shower. An interior laundry room with storage cabinets adds everyday convenience. Three sets of sliding doors create a natural connection to the expansive covered and screened lanai. Finished with paver flooring, this generous outdoor space offers room for relaxing, dining and hosting larger gatherings. A separate paver patio just outside the enclosure provides a convenient grilling area, while refreshed tropical landscaping enhances the setting. Enjoy added peace of mind in Florida with a new roof installed in 2024 and a 2024 Generac 24kW whole-house generator with a transferable warranty and powered by a 500-gallon buried propane tank capable of providing up to three weeks of backup power eliminating much of the stress and uncertainty associated with unexpected power outages, whether short-term or extended. Additional significant improvements made in 2023/2024 include new interior and exterior paint, new laminate flooring and a Puragain water purification system with reverse osmosis in the kitchen. The two-car garage features screen doors, epoxy flooring, a 240-volt connection for electric vehicle charging and attic stairs. Additional features include surround sound, an ADT security system, an irrigation system with a separate irrigation meter, rain gutters, a paver driveway and walkway and more. The monthly maintenance fee of $485 includes lawn care, bush and hedge trimming, exterior home painting, cable TV, internet, trash removal and access to the clubhouse and community amenities. Just a short walk from the home, the lakefront clubhouse offers a heated pool and spa, fitness center, ballroom, library, dance studio, arts and crafts studio and a computer room. Outdoor amenities include shuffleboard, basketball, tennis and bocce ball, along with a community boat ramp, dock and dog park. A new Publix located just outside the community gate makes everyday errands especially convenient, with dining and medical facilities only minutes away. Centrally located between Tampa and Orlando, this thoughtfully improved home offers an inviting opportunity to enjoy the maintenance-free lifestyle of Traditions at Lake Ruby.

4043 Bedford Avenue, Winter Haven
2021 Canton Park Drive, Winter Haven
$325,000
3 Beds ⋅ 2 Baths ⋅ Canton Park SubDv. ⋅ 33881 Zip Code
"PROFESSIONAL PHOTOS COMING SOON." Welcome to 2021 Canton Park, a charming 3-bedroom, 2-bathroom home in Winter Haven. This inviting property offers a comfortable and functional floor plan, with well-proportioned living spaces that make everyday living and entertaining easy. The kitchen provides a practical space for preparing meals and gathering, while the bedrooms offer comfortable accommodations for family, guests, or a home office. Enjoy the convenience of being located in Winter Haven, with easy access to shopping, dining, schools, parks, and major roadways. Whether you are looking for a primary residence, a second home, or an investment opportunity, this property offers a great opportunity to own in Central Florida.

2021 Canton Park Drive, Winter Haven
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