Winter Haven / Cypress Gardens Homes under $250,000

Winter Haven / Cypress Gardens Homes under $250,000

Welcome to Winter Haven, Florida – a charming city nestled in the heart of Polk County, renowned for its stunning lakes, vibrant community, and rich history. Often referred to as the “Chain of Lakes City,” Winter Haven is a picturesque destination that offers a unique blend of natural beauty and modern conveniences. With its lush landscapes and friendly atmosphere, it’s no wonder that families and retirees alike are drawn to this enchanting locale.

One of the most appealing aspects of Winter Haven is its diverse range of housing options, particularly for those seeking affordable homes under $250,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Winter Haven has something to offer everyone. From cozy single-family homes to charming townhouses, you’ll find a variety of properties that cater to different lifestyles and budgets.

Imagine waking up to the serene views of sparkling lakes or enjoying a leisurely afternoon at the nearby Cypress Gardens, which has been transformed into a beautiful botanical garden and adventure park. With a plethora of recreational activities, including fishing, boating, and hiking, Winter Haven is a haven for outdoor enthusiasts.

In addition to its natural allure, Winter Haven boasts excellent schools, shopping centers, and dining options, making it a well-rounded community for residents. With affordable homes and a welcoming atmosphere, Winter Haven is not just a place to live; it’s a place to thrive. Explore the possibilities today and discover why so many are calling Winter Haven home!

Newest Winter Haven / Cypress Gardens Homes under $250,000

1643 Linz Court, Winter Haven
$197,000
2 Beds ⋅ 2 Baths ⋅ S5160341 MLS
Discover the comfort and convenience of this inviting 2-bedroom, 2-bathroom Villa featuring an open-concept layout designed for easy everyday living. The seamless flow between the living spaces creates a welcoming atmosphere, while the screened-in porch offers the perfect spot to enjoy your morning coffee, unwind, or relax outdoors. A convenient laundry closet located in the kitchen adds everyday practicality, and the attached two-car garage provides ample space for parking and storage. Whether you're looking for a comfortable place to call home or a great opportunity to make your own, this property is ready for its next chapter. Don't miss out—schedule your private showing today! The home is being Sold in As Is condition without any Warranty nor Guarantee by seller. The buyer is responsible for verifying ALL property information, room sizes, utilities and condition. HUD Case#: 093-871881

1643 Linz Court, Winter Haven
3115 Captain Jax Way, Winter Haven
$201,790
3 Beds ⋅ 3 Baths ⋅ O6453785 MLS
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3115 Captain Jax Way, Winter Haven
1606 Eagle Pond Drive, Winter Haven
$155,000
2 Beds ⋅ 2 Baths ⋅ S5160340 MLS ⋅ 1606 BLDG.
Step into an inviting opportunity and a genuine deal at this price in the desirable Cypresswood Golf & Country Club. Whether you’re seeking a comfortable full-time residence, a relaxing winter retreat, or a place to embrace an active Florida lifestyle, this second-floor 2-bedroom/2-bathroom condo delivers warmth, convenience, and a true sense of community.Enjoy the privacy of an upper-level location with a practical, easy-flow layout designed for comfortable living, plus a convenient storage room for extra belongings. Maintenance-free ownership means the HOA handles exterior and ground maintenance, community pool access, 24-hour security, common-area upkeep, trash service, exterior pest control, and private road maintenance—so you can simply enjoy your home.The convenient location, a short drive to Legoland Florida Resorts, and offers easy access to Hwy 27, making shopping, dining, medical facilities, and everyday errands quick and simple while still keeping you nestled in a peaceful community setting. Residents are welcomed into a lifestyle filled with amenities: a championship 18-hole golf course, on-site restaurant & clubhouse for dining & events, sparkling community swimming pool, tennis courts & pickleball courts, and fitness center. Perfectly positioned for those who value both relaxed living and an active community atmosphere, this condo offers exceptional value and an immediate sense of belonging in one of Winter Haven’s most appealing settings. Schedule your private showing today and experience the lifestyle for yourself. All buyers must provided a pre-approval letter or proof of funds. Buyers are responsible for verifying the accuracy of all information.

1606 Eagle Pond Drive, Winter Haven
3969 Cypress Landing W, Winter Haven
$250,000
2 Beds ⋅ 2 Baths ⋅ L4966038 MLS
**More PhotosComing** Comfortable, Simple Living in Cypress Landing on Lake Dexter. This 2 Bedroom, 2 Bath Home Has a Vaulted Ceiling Over the Living and Dining Area, and It Makes the Whole Space Feel Open the Minute You Walk In. The Kitchen Has Light-Bright Cabinets, Tile Floors, a Stainless Refrigerator and Dishwasher, a Built In Oven, Cooktop and Microwave, with Sliders Out to the Screened Lanai. The Primary Bedroom Has a Walk In Closet and a Walk In Shower in the Bath. Need More Room? The Enclosed Lanai Gives You Extra Space for a Den, Hobby Room or Home Office. Crown Molding and Ceiling Fans Throughout, a Two Car Attached Garage with Opener and Storage Cabinets, and a Fenced Backyard with Low Maintenance Rock Landscaping. Home Electrical is Generator Ready. The Home Includes Hurricane Shutters - Easy Up And Down Installation. Cypress Landing Offers a Clubhouse, Community Pool, Tennis and Pickleball Courts, Boat Storage, a Private Boat Ramp and a Dock on the Lake. Minutes from Legoland, Shopping and Dining. Schedule Your Showing Today! All Sizes Approximate. Buyer to Verify.

3969 Cypress Landing W, Winter Haven
4925 Cypress Gardens Road Unit 97, Winter Haven
$180,000
2 Beds ⋅ 2 Baths ⋅ P4940253 MLS
Welcome to this meticulously maintained 2-bedroom, 2-bathroom double-wide mobile home located in a 55+ co-op community. The home features brand-new vinyl plank flooring in the main living area and a newly remodeled kitchen, giving the interior a fresh, updated feel. Outside, a long attached carport provides ample covered parking, while an attached storage shed offers additional space for tools and equipment. The community offers a variety of amenities and activities, including a heated swimming pool, shuffleboard courts, a pickleball court, a basketball court, an exercise room, a woodshop, a dog park, and a pond. With plenty of opportunities for recreation, hobbies, and socializing, this community offers an active lifestyle with something for everyone. Furniture is negotiable and may be included if desired by the buyer.

4925 Cypress Gardens Road Unit 97, Winter Haven
3084 Captain Jax Way, Winter Haven
$209,990
3 Beds ⋅ 3 Baths ⋅ O6452374 MLS
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3084 Captain Jax Way, Winter Haven
3437 Grenville Drive, Winter Haven
$223,000
2 Beds ⋅ 2 Baths ⋅ P4940235 MLS
Discover this 2-bedroom, 2-bath home filled with potential and ready for its next owner. Located in Traditions at Lake Ruby, a maintenance-free, gated 55+ community, this thoughtfully designed home combines comfort, functionality, and style for relaxed Florida living. The kitchen features maple wood cabinetry, an updated microwave, reverse osmosis at the kitchen sink, and a convenient closet pantry. The dining area is highlighted by vaulted ceilings and a decorative arched pass-through to the kitchen, adding character and charm. The open-concept floor plan offers a spacious living room with a decorative planter shelf and triple sliding glass doors leading to the Florida room, where tranquil garden views create a peaceful setting. The primary bedroom suite offers serene backyard views and a walk-in closet. The en-suite primary bathroom is designed for comfort, featuring a comfort-height vanity, tile flooring, and a walk-in shower with a glass door. Enjoy outdoor living even during inclement weather from the Florida room, while the low-maintenance courtyard, enhanced with pavers and Florida-friendly landscaping, provides a private and inviting outdoor retreat. The fenced backyard with mature plantings offers additional outdoor space. Additional features include a laundry pantry with washer and dryer, architectural shingle roof (2020), HVAC system (2017), exterior lighting, water softener system, gutters, a glass entry storm door, and a two-car garage. A paved driveway and walkway further enhance the home's curb appeal. Traditions at Lake Ruby offers an impressive array of amenities, including a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, tennis and basketball courts, bocce, shuffleboard, fitness center, and aerobics studio. Residents can also enjoy a variety of planned community activities. Monthly HOA fees cover front-yard lawn service, cable tv, internet, exterior house painting, and community clubhouse amenities helping provide a convenient, low-maintenance lifestyle. Ideally located near shopping, restaurants, medical facilities, Legoland, and major routes, this home offers a wonderful combination of comfort, convenience, and vibrant community living.

3437 Grenville Drive, Winter Haven
251 Greenfield Road, Winter Haven
$224,900
2 Beds ⋅ 2 Baths ⋅ TB8561003 MLS
VACANT AND PRICED TO SELL! NEW ROOF 2025! 2 BED 2 BATH CONCRETE BLOCK STUCCO (CBS) HOME IN GUARD GATED CYPRESSWOOD GOLF AND COUNTRY CLUB, WINTER HAVEN FL 33884. Vacant single story home on a 0.44 acre lot with an attached garage, central air, and no CDD. Roof replaced 2025 and water heater 2017. The home needs some work and is priced for its condition. Seller is open to making repairs needed for FHA or conventional loan approval. Cypresswood is a golf cart friendly golf course community with a 24 hour guard gate, 18 hole championship golf course, clubhouse, community pool, and tennis. Located in Polk County near Legoland Florida, Cypress Gardens, the Chain of Lakes, shopping, dining, US 27, and the I-4 corridor between Orlando and Tampa. FHA, VA, conventional, and cash welcome. Sold as is.

251 Greenfield Road, Winter Haven
100 El Camino Drive Unit 208, Winter Haven
$139,900
1 Beds ⋅ 1 Baths ⋅ O6451540 MLS ⋅ 100 BLDG.
OWNER MOTIVATED Beautiful Condo, Tastefully remodeled, completely updated in 2023. All new appliances, granite counter tops, remote controlled fans, Kitchen and bathroom new cabinets. Come enjoy Florida Living or just retire in style or enjoy it as your Winter Getaway. A small Bonus space may be used as a second sleeping quarters for additional guests. Conveniently located near shopping centers, restaurants, hospitals, churches and more. HOA fees cover your cable, internet, water, sewer, trash pick up and natural gas. Exclusive Carport. Seller will assist you with closing costs or interest rate buy down if needed.

100 El Camino Drive Unit 208, Winter Haven
100 El Camino Drive Unit 103, Winter Haven
$59,000
1 Beds ⋅ 1 Baths ⋅ L4965857 MLS ⋅ 1 BLDG.
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
6066 Se Southern Oaks Drive, Winter Haven
$126,900
2 Beds ⋅ 2 Baths ⋅ S5159435 MLS
Motivated Seller! Let's make a deal. Welcome to life at Garden Grove Oaks, a quiet 55+ community tucked away in the Southeast Winter Haven/Garden Grove area. Step inside this 2 bed/2 bath home to an open floor plan with a dining area conveniently to the right and the kitchen on your left, which includes a refrigerator, range, microwave, and dishwasher. Cathedral ceilings create an open, spacious feel, leading into the living room. The primary bedroom includes an en-suite bathroom with a step-in shower. Fans throughout the house help keep it cool. Two screened porches (front and side) give you options for enjoying the outdoors. Enjoy a morning coffee on the front screened porch which provides shade and a cool breeze and room for your favorite hobbies. The side porch behind the carport features tile flooring. Behind the side porch is an adjoining storage area with two work benches 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. Enjoy the newer roof (2024), vinyl siding, a carport, and a long driveway, adding everyday convenience. Plenty of outdoor space with a nice sized backyard and the neighboring lot is vacant and owned by the next-door neighbor. Garden Grove Oaks low community fees offer a nice pool, shuffleboard 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 ⋅ P4940202 MLS
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
Start Your Search

How much is your home worth?

Get instant property value now!