Quick Winter Haven FL MLS Search

Browse All Winter Haven FL Under $200K Properties for Sale

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

6733 Kensington Drive Ne, Winter Haven
$165,500
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates SubDv. ⋅ 33881 Zip Code
Charming 2-Bedroom, 2-Bath Home on a Corner Lot Near Lake Henry! Welcome to this beautifully maintained 2-bedroom, 2-bathroom home, where pride of ownership shines from the moment you arrive! From the unique guitar-themed driveway artwork to the immaculate interior, this inviting home is ready for you to move in and enjoy. A new HVAC system installed in 2026 adds to the home's appeal. Situated on a desirable corner lot, the home is located on a street leading directly to the community boat dock overlooking scenic Lake Henry. Whether you enjoy spending time on the water, participating in community activities, or simply relaxing and socializing with neighbors, this location offers plenty of opportunities to enjoy the Florida lifestyle. Inside, the thoughtfully designed floor plan features a bright kitchen with white cabinetry, white appliances, and a convenient center island with seating—perfect for casual meals or morning coffee. Just off the kitchen, the indoor laundry area offers upper cabinets for added storage and organization. The formal dining room features a built-in china cabinet, providing a lovely setting for entertaining family and friends. Adjacent to the dining area, the family room flows seamlessly into the home's entertaining spaces, with sliding glass doors leading to an oversized lanai that spans nearly the entire width of the home. This generous outdoor living area offers plenty of room to relax, entertain, and enjoy Florida's beautiful weather. Both bedrooms offer convenient access to their own bathrooms, providing added privacy and comfort for residents and overnight guests alike. Residents enjoy an active community lifestyle with a variety of amenities and social events offered throughout the month. Conveniently located near shopping, medical facilities, restaurants, and live entertainment, this home also provides easy access to the recreational opportunities and social activities available within the community. Come discover the charm, comfort, and lifestyle this inviting home has to offer!

6733 Kensington Drive Ne, Winter Haven

183 Osprey Heights Drive, Winter Haven
$189,900
3 Beds ⋅ 2 Baths ⋅ Osprey Landings SubDv. ⋅ 33880 Zip Code
Under contract-accepting backup offers. 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

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

6619 Westchester Drive Ne, Winter Haven
$155,990
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

200 El Camino Unit 106, Winter Haven
$75,900
1 Beds ⋅ 1 Baths ⋅ Orchid Springs Vill #200 Condominuim SubDv. ⋅ 33884 Zip Code
***JUST REDUCED***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

10 Lychee Drive, Winter Haven
$130,000
1 Beds ⋅ 2 Baths ⋅ Clearview Estates SubDv. ⋅ 33881 Zip Code
Under contract-accepting backup offers. LAKE VIEWS & FUNCTIONAL FLEXIBLE SPACE—ALL IN ONE! Welcome to 10 Lakeview Drive in Winter Haven, a charming 1-bedroom, 1.5-bath 720 sq. ft home in the quaint 55+ Clearview Estates community, where peaceful lake views and laid-back Florida living come together. Step inside and you’ll immediately notice the natural light filling the open living and dining area that flows seamlessly to the kitchen which offers ample cabinetry and generous counter space making it both functional and inviting. One of the home’s most versatile features is the oversized laundry room (complete with a front load washer and dryer) that could double as a bonus room, home office, hobby space, or easily be transformed into a second guest bedroom to create even more flexibility! An additional enclosed Florida room provides even more living space and is perfect for relaxing, enjoying your morning coffee, pursuing hobbies, or simply soaking up the Florida lifestyle. Outside, the possibilities continue. Unwind in the evening from the front porch with a serene view of Lake Mariana. The Community also offers dock access, giving you an opportunity to enjoy the water and wildlife. A covered carport, additional storage areas, and a detached garage with roll-up doors on both ends provide plenty of room for vehicles, equipment, tools, recreational items, and personal belongings. The garage also features its own half bath, an especially convenient touch for anyone working on cars, projects, with tools, or equipment. No need to track through the house when you need to wash up or use the restroom—just another thoughtful feature that makes this property exceptionally functional. And for added efficiency, the home features Tesla solar panels, which can provide significant monthly savings on electricity costs! If you’ve been looking for a cozy Winter Haven home to settle down in, you've found it!

10 Lychee Drive, Winter Haven

5850 Cypress Gardens Boulevard Unit 303, Winter Haven
$179,000
3 Beds ⋅ 3 Baths ⋅ Royal Crescent Condo SubDv. ⋅ 33884 Zip Code
3 BEDROOM 2.5 BATH CONDO ON CYPRESS GARDENS BLVD: Affordable, spacious and move-in ready, this 3-bedroom, 2.5-bath condo offers more than 1,500 square feet of living space in Royal Crescent, directly across from LEGOLAND in the heart of SE Winter Haven. The residence features an updated kitchen and bathrooms, double-pane windows and sliding doors, a private outdoor patio and two assigned parking spaces. Royal Crescent offers an established residential setting just off Cypress Gardens Boulevard, with classic traditional architecture, columned entries, a large central green shaded by mature trees and a newly remodeled community swimming pool—all at a price point that makes comfortable, convenient living surprisingly affordable. Inside, the two-story floor plan provides generous living spaces downstairs with the bedrooms privately situated upstairs. The main level includes formal living and dining areas, a separate family room, half bath and multiple storage closets, with warm wood flooring extending throughout much of the home. The kitchen features updated white cabinetry, abundant counter and storage space and a full complement of like-new appliances. An interior laundry closet with Maytag washer and dryer adds everyday convenience. Upstairs, the spacious primary suite includes two closets and a private en-suite bath. Two additional bedrooms are comfortably sized with generous closets, ceiling fans and convenient access to the full guest bath. Wood flooring continues into the bedrooms, and the upper level enjoys elevated views across the community and surrounding area. One of the home's most enjoyable features is the private rear patio. Fully enclosed for privacy and large enough for an outdoor dining table and additional seating, it provides genuine outdoor living space for morning coffee, grilling or relaxing in the Florida sunshine. Royal Crescent's location places an impressive amount of everyday life within a very small radius. Legoland Florida Resort is directly across Cypress Gardens Boulevard, with Publix, Starbucks, restaurants, shopping, fitness and entertainment nearby. Downtown Winter Haven is just a short drive away, while Highway 27 provides convenient access toward the greater Orlando and Tampa areas. Beyond its convenience, Winter Haven is a city defined by its lakes. The area's Chain of Lakes provides miles of interconnected waterways for boating, fishing, watersports and waterfront dining, while downtown offers locally owned restaurants, coffee shops, breweries, boutiques, parks and community events. It is a distinctly Central Florida lifestyle with many of the conveniences of a larger city without losing Winter Haven's established, small-city character.

5850 Cypress Gardens Boulevard Unit 303, Winter Haven

100 El Camino Drive Unit 301, Winter Haven
$149,900
3 Beds ⋅ 3 Baths ⋅ Orchid Spgs Vill 100 Condo SubDv. ⋅ 33884 Zip Code
Welcome to 100 El Camino Drive, Unit 301, a spacious corner-unit condominium located in the established Orchid Springs community of Winter Haven. As one of the larger residences in the building, this home offers an appealing combination of generous living space, privacy, convenience, and low-maintenance Florida living. The thoughtfully designed floor plan provides each bedroom with its own private full bathroom, making the home especially well suited for guests, multi-generational living, or owners who simply appreciate added privacy. As a corner unit, the residence benefits from an enhanced sense of separation and space, while additional storage provides room for seasonal items and everyday necessities. Major improvements include a 2023 Heating system and the home has been replumbed throughout, offering valuable updates for the next owner. Additional conveniences private storage, elevator access, and a designated parking space. Orchid Springs offers a peaceful residential setting highlighted by beautifully maintained grounds and scenic water features, along with access to a private community pool and clubhouse. The monthly association fee provides exceptional convenience by including water, gas, cable, internet, and trash service, helping simplify monthly expenses. Community amenities also include pool and clubhouse access, with association services supporting an easy, low-maintenance lifestyle. The location places you in the heart of everything Winter Haven has to offer. Enjoy convenient access to shopping, dining, medical services, downtown Winter Haven, LEGOLAND® Florida Resort, and the famous Winter Haven Chain of Lakes. Known as the “Chain of Lakes City,” Winter Haven offers abundant opportunities for boating, fishing, kayaking, waterfront dining, and other outdoor recreation while remaining conveniently positioned within Central Florida. Spacious, updated, and packed with included amenities, Unit 301 offers an excellent opportunity to enjoy comfortable condominium living in one of Winter Haven’s most distinctive established communities.

100 El Camino Drive Unit 301, Winter Haven

1100 Martinique Drive Unit 220, Winter Haven
$149,900
3 Beds ⋅ 2 Baths ⋅ Orchid Spgs Vill 300 Barcelona SubDv. ⋅ 33884 Zip Code
Welcome to easy Florida living in the desirable community of Orchid Springs! This beautifully updated second-floor CORNER/END-UNIT condo offers a wonderful sense of privacy along with an abundance of natural light. Featuring a spacious, open split-bedroom floor plan with 3 bedrooms, 2 bathrooms, an enclosed bonus room and a dedicated inside laundry room, this modern-looking unit provides plenty of comfortable & flexible living space. Thoughtful updates and custom touches can be found throughout, including crown molding and stylish finishes. The beautiful kitchen features granite countertops, updated stainless steel appliances and plenty of cabinet and counter space, creating a functional and inviting space for everyday living and entertaining. The spacious primary suite offers a walk-in closet and private ensuite bathroom with a step-in shower and granite countertop. The split-bedroom layout provides added privacy for family or guests, while the enclosed bonus room adds valuable additional living space and can easily serve as a home office, den, hobby room or additional sitting area. Additional conveniences include a full inside laundry room with washer and dryer included, as well as assigned covered parking. Some of the furniture may also be negotiable, making this an excellent option for buyers looking for an easier transition into their new Florida home. One of the many benefits of Orchid Springs is the affordable condo fee, which includes water, gas, sewer, trash, exterior building maintenance and grounds maintenance, providing for a convenient, low-maintenance lifestyle. Residents also enjoy access to the community clubhouse and swimming pool. Ideally located in SE Winter Haven near Highway 27, this condo provides convenient access to shopping, restaurants, medical facilities, LEGOLAND Florida Resort and everyday necessities. Winter Haven's Central Florida location between Tampa and Orlando also makes it convenient for enjoying everything the region has to offer. Whether you are looking for a full-time residence or a seasonal Florida retreat, this beautifully updated corner unit combines privacy, natural light, modern finishes, additional living space and a convenient location. Schedule your private showing today!

1100 Martinique Drive Unit 220, Winter Haven

1711 Garden Lake Drive Unit 1711, Winter Haven
$170,000
1 Beds ⋅ 1 Baths ⋅ Winterset 02 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to a little slice of Florida paradise in Winterset, a GATED WATERFRONT COMMUNITY nestled along Winter Haven’s famous Chain of Lakes. This charming 1-bedroom, 1-bathroom condominium offers something truly special: a relaxed lakeside lifestyle, resort-style community amenities, and a home filled with unique spaces and thoughtful updates. Inside, the primary bedroom is wonderfully spacious and features a huge walk-in closet and en suite bathroom. But, one of the home's most delightful surprises is the fun overhead loft, creating flexible bonus space that could be the perfect home office, media area, reading nook, hobby space—or simply your own cozy hideaway. And when it comes to storage, you'll have plenty of room for all the things you don't want taking up your living space, thanks to additional interior AND exterior storage. Major updates mean you can settle in with confidence, too. The HVAC SYSTEM and WATER HEATER were both REPLACED in 2024, giving you two important big-ticket improvements already taken care of. Then there's the lifestyle... Step outside and enjoy everything Winterset has to offer. Take advantage of the community dock and lake access on the SE Chain's coveted Lake Winterset, spend a sunny afternoon at the pool and spa, meet friends at the clubhouse, or enjoy a friendly game of tennis or shuffleboard. When you're ready to get out on the water, Winter Haven's interconnected Chain of Lakes offers endless opportunities for boating, fishing, relaxing, and enjoying those beautiful Florida sunsets. The location is another reason to love this home. You're conveniently close to LEGOLAND Florida Resort, restaurants, grocery shopping, medical facilities, and everyday essentials, while downtown Winter Haven and its lakeside dining and local attractions are also just a few minutes away--whether by boat or by car. Whether you're searching for a full-time Florida home, a weekend retreat, a place to escape the cold, or simply a low-maintenance home where there's always something fun to do, this Winterset condo offers an appealing blend of comfort, character, recreation, and location.

1711 Garden Lake Drive Unit 1711, Winter Haven

1776 6th Street Nw Unit 304, Winter Haven
$92,900
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven

Start Your Search

Under $200K Winter Haven Real Estate

Our website features the best real estate search for under $200k properties available in Winter Haven and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

How much is your home worth?

Get instant property value now!