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$185,000
2 Beds ⋅ 1 Baths ⋅ Parkland Village SubDv. ⋅ 33880 Zip Code
Welcome home to this well-maintained 2-bedroom, 1-bath patio home located in the 55+ community of Parkland Village. This move-in-ready home offers numerous recent updates, including a new roof (December 2025), new windows (2024–2025), new A/C (2022), and a new refrigerator and stove (2026), providing comfort and peace of mind for years to come. Inside, you'll find thoughtful features such as vertical blinds, mirrored closet doors, and storm doors and shutters. The home also includes a private courtyard, perfect for relaxing or entertaining, along with a 1-car carport and a storage closet with a washer and dryer. Residents enjoy access to a recreation building and shuffleboard courts, while the low monthly HOA fee of just $110 includes grounds maintenance, making for easy, low-maintenance living. Conveniently located near shopping, banks, and restaurants, this home offers the perfect combination of comfort, convenience, and affordability. Don't miss this opportunity—schedule your private showing today!

790 Avenue Q Se, Winter Haven
$165,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Tennis Villas SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to effortless Florida living in the highly sought-after gated Cypress Wood Golf & Country Club! Perfectly positioned on the beautifully maintained 10th hole, this 2-bedroom, 2-bath villa offers over 1,100 square feet of comfortable living with no close rear neighbors—just breathtaking views of lush fairways, mature oak trees, and Florida wildlife. Inside, you’ll find a bright, open floor plan complete with a spacious Florida room, the perfect place to enjoy your morning coffee or unwind while taking in the peaceful golf course scenery. Offered fully furnished with quick occupancy available, this home is truly move-in ready. Beyond the entrance, experience the exceptional lifestyle that makes Cypress Wood one of Central Florida’s most desirable golf communities. Enter through a 24-hour guard gate and enjoy a scenic drive along beautifully landscaped, tree-lined streets surrounded by meticulously maintained grounds and natural beauty. Residents have access to outstanding amenities including an 18-hole championship golf course, clubhouse, restaurant, community pool, tennis courts, pickleball courts, and a vibrant social atmosphere. The HOA provides lawn maintenance and exterior upkeep, allowing you to spend more time enjoying everything this resort-style community has to offer. Conveniently located just minutes from LEGOLAND Florida Resort, shopping, dining, and everyday conveniences, with easy access to Highway 27 and I-4, offering an easy commute to both Orlando and Tampa. Whether you’re searching for a full-time residence, winter retreat, or investment opportunity, this villa offers the perfect blend of comfort, convenience, and carefree Florida living. Schedule your private showing today !

665 Broadmoor Circle, Winter Haven
$129,500
2 Beds ⋅ 1 Baths ⋅ Orchid Spgs Vill 300 Barcelona SubDv. ⋅ 33884 Zip Code
Virtually Staged. Nestled within the peaceful and highly desirable Orchid Springs Village, this beautifully renovated ground-floor condominium offers the perfect blend of modern style, low-maintenance living, and an unbeatable Winter Haven location. Designed with comfort and functionality in mind, the bright open floor plan seamlessly connects the living and dining areas, creating an inviting space filled with abundant natural light. Beautiful luxury vinyl plank flooring flows throughout the home, while the updated kitchen showcases crisp white cabinetry, stunning stone countertops, stainless steel appliances, and a desirable gas range—combining timeless style with everyday functionality. The spacious bedroom offers a relaxing retreat with generous closet space, while the beautifully remodeled bathroom features an updated vanity and a sleek glass-enclosed tiled shower with tub. Just beyond the main living area, a versatile FLEX ROOM provides the perfect space for a home office, reading nook, hobby room, fitness area, or additional sitting room to suit your lifestyle. Beyond the flex space, the ENCLOSED SUNROOM is surrounded by expansive windows that overlook the lush, manicured grounds, creating a peaceful setting to enjoy your morning coffee, unwind with a good book, or simply relax while taking in the tranquil views, with direct access to the outdoor green space. Residents of Orchid Springs Village enjoy a carefree lifestyle with exceptional community amenities, including a sparkling swimming pool, clubhouse, scenic walking paths, convenient laundry facilities, assigned covered carport parking, and beautifully maintained landscaping. The monthly condominium fee provides outstanding value by covering water, sewer, trash, natural gas, exterior maintenance, and recreational facilities, allowing for truly stress-free ownership. Perfectly positioned in the heart of Winter Haven, this move-in-ready condo is just minutes from Winter Haven Hospital, shopping centers, local restaurants, golf courses, and the vibrant downtown district. Outdoor enthusiasts will appreciate the proximity to Lake Shipp Park and Lake Hartridge Nature Park, while the world-famous LEGOLAND® Florida Resort and Winter Haven's renowned Chain of Lakes are just a short drive away. With easy access to US-27 and the Polk Parkway, commuting to Orlando, Tampa, and surrounding Central Florida destinations is effortless. Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this beautifully updated condo offers the ideal combination of comfort, convenience, and resort-style living.

1100 Martinique Drive Unit 106, Winter Haven
$110,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Move right into this furnished home located in Oakwood Estates, a 55+ community. The carpet throughout the home is in excellent condition. The rooms are very spacious and inviting. The home has been very well maintained. The dishwasher was installed in 2018, the washer and dryer 2020, and the refrigerator in 2024. Enjoy the bonus room on the front of the home or sit and watch the world go by on the comfortable lanai. Oakwood Estates offers many activities and amenities. If you are looking for exercise, you can join in with the pool or indoor aerobics. Chair Yoga is offered twice a week, or play some pool volleyball. The tennis court has recently been refinished and there is a pickle ball group that meets three times a week. During the winter months, there are several exciting dances as well as many activities. If food is your thing, Oakwood offers potluck dinners, ice cream socials, and weekly coffee and donuts. If you are looking for full time or just part time, this is your opportunity to move into a wonderful community, conveniently priced.

4807 Plumwood Street, Winter Haven
$337,000
2 Beds ⋅ 2 Baths ⋅ Lake Dexter Woods Ph Two SubDv. ⋅ 33884 Zip Code
PRESENTING A CHARMING LAKEFRONT RETREAT ON LAKE DEXTER! This beautifully maintained 2-bedroom, 2-bath residence with a 1-car garage offers an exceptional blend of comfort, thoughtful upgrades, and waterfront living. The spacious kitchen flows seamlessly into the open living area, creating an inviting setting for everyday living and entertaining, complete with a modern LED fireplace. Travertine flooring extends throughout most of the home, while the guest bedroom features warm bamboo flooring. Plantation shutters and newer PGT hurricane-impact windows provide added beauty, energy efficiency, and peace of mind. Additional improvements include a three-year-old energy-efficient metal roof, radiant barrier insulation in the attic, an Amarr triple-steel insulated garage door, and low-maintenance composite decking. The primary bedroom offers two custom built-in closets and a comfortable private retreat. Step outside to enjoy the patio, composite deck, private dock, and two boat slips on beautiful Lake Dexter. Whether boating, fishing, kayaking, or simply relaxing while taking in the tranquil lake views, this property provides the perfect opportunity to experience the Florida waterfront lifestyle.

679 Lake Dexter Circle, Winter Haven
$189,900
2 Beds ⋅ 2 Baths ⋅ Jarvis Heights SubDv. ⋅ 33881 Zip Code
Great location just needs some TLC. This 1,110 sq.ft. home is located in the heart of Winter Haven minutes to downtown hospital and walking distance to Polk State College. Featuring 2 bedrooms and 2 bathrooms, this home has undergone some renovations but looking for someone to finish off with their own touches. The property features a new metal roof, new luxury. vinyl flooring, split unit (2022), and full electric and plumbing in 2022. The kitchen has also been updated with new cabinets and stainless appliances. Outside you have plenty of possibilities. The detached building is ready to be made into a mother-in-law suite or perfect man cave. Large back porch and chicken coop are other perks of this listing. Call or text to see it today! *Agents, please read MLS remarks.*

650 9th Street Ne, Winter Haven
$90,500
2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Vill 200 Condo SubDv. ⋅ 33884 Zip Code
Under contract-accepting backup offers. WELCOME TO THE SEVILLE BUILDING IN BEAUTIFUL ORCHID SPRINGS. THIS IS A LARGE (1,378 SQUARE FEET) TWO BEDROOM TWO BATH UNIT LOCATED ON THE THIRD FLOOR. ELEVATORS ARE POSITIONED IN THE CENTER OF THE BUILDING FOR RESIDENTS CONVENIENCE. THIS UNIT HAS BEEN UPGRADED AND IS READY FOR IT'S NEW OWNERS. THIS FLOORPLAN HAS A SPLIT- BEDROOM PLAN. THE RESIDENCE OVERLOOKS A BEAUTIFUL TROPICAL LAGOON. THE ROOF WAS REPLACED IN 2025 AND THE ENTIRE BUILDING IS CURRENTLY BEING PAINTED. THE GALLEY KITCHEN HAS BEEN REDONE AND HAS STAINLESS STEEL APPLIANCES. THE PRIMARY BEDROOM IS SPACIOUS WITH A REMODELED ENSUITE BATH WITH A HUGE WALK-IN CLOSET. THE SECOND BEDROOM HAS ACCESS TO ITS OWN UPDATED BATH ALSO. THE MONTHLY HOA FEE COVERS, GAS, WATER, TRASH, SEWER, CLUBHOUSE & POOL, EXTERIOR MAINTENANCE AND GROUNDS UPKEEP. THIS WELL-KEPT HOME IS PRICED TO SELL.

200 El Camino Drive Unit 311, Winter Haven
$99,000
2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
Peaceful oasis in a premier 55+ community! This lovely 2 bedroom, 1 bath second-floor condo in Winter Haven Harbour Apartments offers a perfect blend of comfort, functionality, and an active, low-maintenance lifestyle. Inside, you will find a spacious living room that flows effortlessly into a dedicated dining room, and a galley-style kitchen that maximizes counter space and storage, making meal preparation a breeze. Step onto your private balcony, where you can enjoy your morning coffee, read a book, or soak in the serene views. This wonderful active community offers fantastic resort-style perks, including a sparkling heated community pool, an active community center, and shuffleboard courts for fun with friends and neighbors. This home provides the ideal setting for your next chapter. Don't miss out, schedule your appointment today.

1700 6th St Nw Unit C24, Winter Haven
$149,900
2 Beds ⋅ 2 Baths ⋅ Spring Lake Towers SubDv. ⋅ 33881 Zip Code
Enjoy maintenance-free lakefront living in this 2-bedroom, 2-bathroom condominium located in the highly sought-after Spring Lake Towers, a premier 55+ active adult community in the heart of Winter Haven. Updated in 2020, this inviting residence offers BREATHTAKING VIEWS OF SPRING LAKE, part of the scenic Spring Lake Meander, and a bright, open living space that feels like an indoor lanai, where walls of windows create the perfect setting to relax while overlooking the tranquil water. Both the primary bedroom and the second bedroom have direct access to this enclosed lakefront space, creating a seamless connection to the serene waterfront and providing the perfect spot to enjoy your morning coffee, unwind with a book, or simply take in the picturesque views of Spring Lake throughout the day. The updated kitchen is designed for both style and function, featuring soft-close cabinetry, porcelain countertops, recessed lighting, a decorative tile backsplash, a convection oven, and a convenient center island cart. Luxury vinyl flooring flows throughout the main living areas, while the bedrooms offer the comfort of carpet. The spacious primary suite features a walk-in closet and an ensuite bath, while the secondary bathroom has been tastefully updated with a beautifully tiled glass-enclosed shower. The all-inclusive condo fee provides exceptional value, covering cable TV, high-speed internet, water, sewer, trash removal, exterior building maintenance, roof maintenance, building insurance, reserve funds, on-site management, groundskeeping, and assigned covered parking. Residents enjoy an impressive selection of community amenities, including a waterfront in-ground concrete pool, fitness center, recreation room with a full kitchen, library, game area, shuffleboard courts, laundry facilities, private boat docks, and a year-round social calendar. Take advantage of the community's private dock, where boat slips are available on a first-come, first-served basis for a minimal monthly fee, offering convenient access to Spring Lake Meander for boating, fishing, or simply enjoying the peaceful waterfront setting. Ideally located just minutes from historic downtown Winter Haven, the renowned Chain of Lakes, shopping, dining, medical facilities, golf courses, and LEGOLAND® Florida Resort, this waterfront condo offers the perfect blend of low-maintenance living, spectacular views, and an active Florida lifestyle.

700 Mirror Terrace Nw Unit 511, Winter Haven
$159,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood Eagle Pond Condominium SubDv. ⋅ 33884 Zip Code
Don't miss the opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Virtually maintenance-free Florida living doesn't get any better. Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas, including a kitchen breakfast bar. Walk-in closets in both bedrooms offer an abundance of space for organizing your belongings, and an en suite bathroom in the main bedroom for privacy and convenience. Enjoy the open-concept living area for entertaining friends and family and a private patio further compliment this delightful property. Immerse yourself in the outdoors on your private patio or take a walk, run, or bike ride to enjoy the natural scenery that abounds in this community. Cypresswood Golf and Country Club features a 24-hour manned guard gate, 18-hole championship golf course, junior Olympic-sized community pool, lighted tennis/pickleball/basketball courts, clubhouse, restaurant, pro-shop, event space, and so much more. The low monthly HOA fee includes all exterior and grounds maintenance, pest control, trash collection, and use of the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual membership! 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. Schedule your private showing today!

1502 Eagle Pond Drive Unit 15, Winter Haven
$174,900
2 Beds ⋅ 2 Baths ⋅ Lake Shipp Heights SubDv. ⋅ 33880 Zip Code
Welcome Home! If you've been dreaming of homeownership but thought it was out of reach, this could be the opportunity you've been waiting for. This charming 2-bedroom, 1.5-bath home also features a versatile bonus room that could be used as a 3rd bedroom, home office, playroom, hobby room, or extra storage space. Situated in a well-established Winter Haven neighborhood, this home offers the perfect chance to begin building equity instead of paying rent. One of the standout features is NO HOA, giving you the freedom and flexibility that so many buyers are looking for. The fully fenced yard provides a great space for pets, kids, entertaining, or simply relaxing in your own private outdoor space. Whether you're a first-time homebuyer looking for a place to call your own or an investor searching for your next rental property, this home offers plenty of potential. The functional layout, cozy feel, and flexible living space make it easy to envision making it your own over time. Conveniently located near shopping, restaurants, schools, and major roadways, you'll enjoy easy access to everything Winter Haven and the surrounding area has to offer. Even better, the seller will be installing a BRAND-NEW ROOF prior to closing, giving the new owner added peace of mind and one less major expense to worry about. Your first home doesn't have to be your forever home—it just has to be your start. Come see the possibilities this home has to offer!

112 Palm Drive, Winter Haven
$165,000
2 Beds ⋅ 2 Baths ⋅ Garden Villas 02 Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to your private Florida condo! Ideally situated just minutes from LEGOLAND and within an hour of both Tampa and Orlando, this unit offers the perfect balance of convenience and serenity. The home features a beautifully updated kitchen and bathrooms, complemented by sleek, modern tile flooring throughout. Positioned at the end of the building with no structures directly in front, this unit provides exceptional privacy. Whether you are looking to expand your investment portfolio or seeking a personal residence, this property is an excellent choice. A definite must-see—come make it your own!

5203 Waterview Way Unit 5203, Winter Haven
$145,000
2 Beds ⋅ 2 Baths ⋅ Winter Rdg Condo SubDv. ⋅ 33881 Zip Code
Enjoy peaceful lakeside living at 207 Winter Ridge Blvd! This 2-bedroom, 2-bath condo is ready to move into. The home features an enclosed Florida room, primary bedroom with walk in closet, open floor plan, and stunning lake views. The community features a pool, clubhouse, shuffleboard, and a lot more. Call, text, or email for your private showing. *Agents, please read MLS remarks.*

207 Winter Ridge Boulevard Unit 4, Winter Haven
$78,800
2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
Virtually Staged. Perched on the third floor, Unit A38 at Winter Haven Condominiums offers the perfect combination of privacy, comfort, and peaceful views. As a desirable end unit, you'll enjoy extra windows that fill the home with natural light along with added privacy from neighboring units. Best of all, elevator access means you can enjoy the top-floor location without worrying about the stairs. Inside, the condo has been thoughtfully updated with newer flooring, fresh interior paint, and modern kitchen cabinetry featuring soft-close doors, creating a bright, inviting space that's truly move-in ready. Just outside your front door, the screened breezeway becomes an extension of your living space. Sip your morning coffee as the day begins, relax with a good book in the afternoon, or unwind in the evening while enjoying Florida's warm breeze and peaceful surroundings. Life here is about more than just the condo. Cool off in the community pool, enjoy a friendly game of outdoor shuffleboard, or take advantage of the community clubhouse, a comfortable, air-conditioned gathering space designed for both relaxation and entertainment. Inside, you'll find a pool table, indoor shuffleboard, fitness equipment, television, and a fully equipped kitchen that's perfect for hosting birthdays, holiday gatherings, game nights, or casual get-togethers. Just bring your favorite food, invite your family and friends, and enjoy the space without the hassle of entertaining at home. Covered, assigned parking is conveniently located just steps from the building, making everyday living even easier. Whether you're looking for a year-round residence or a seasonal escape from colder climates, Unit A38 offers low-maintenance living in a welcoming community where comfort, convenience, and relaxation come together. Schedule your private showing today and experience everything this charming condo has to enjoy.

1700 6th Street Nw Unit A38, Winter Haven
$180,000
2 Beds ⋅ 1 Baths ⋅ Daniels Sub SubDv. ⋅ 33880 Zip Code
Welcome to this charming, move-in ready 2-bedroom, 1-bath home in the heart of Winter Haven! Freshly painted and filled with natural light, this home offers a comfortable layout, a spacious backyard perfect for entertaining or relaxing, and public water and sewer services for added convenience. The roof has been replaced in recent years, providing additional value and peace of mind. Conveniently located near shopping, dining, schools, parks, and major roadways, this property is an excellent opportunity for first-time homebuyers, downsizers, or investors. Schedule your private showing today!

139 Avenue G Se, Winter Haven
$235,000
2 Beds ⋅ 2 Baths ⋅ Yonnally W P Resub SubDv. ⋅ 33881 Zip Code
Beautifully refreshed home located in a quiet, established neighborhood in Winter Haven! Freshly painted and offering spacious living areas, this property provides a comfortable and inviting layout that’s ready for its next owner. Enjoy the freedom of NO HOA while being conveniently located near shopping, restaurants, schools, parks, medical facilities, and major roadways. A great opportunity for first-time buyers, growing families, or anyone looking for generous interior space in a peaceful residential setting. Buyer to verify all measurements and property information. Contact the listing agent for additional details or to schedule a showing.

629 Avenue A Ne, Winter Haven
$162,000
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
NEW LISTING IN CENTRAL FLORIDA. CONDO IN 55+ Gated Community. This condominium provides 1.347 SF of living area 2 bedrooms, 2 baths, Bonus room with views of Spring Lake & is located in the beautiful City of Winter Haven. Lakeridge Condominiums offers a maintenance free lifestyle with heated pool, tennis, shuffleboard, community room, gated secured entrances and covered assigned parking space. Water, sewer, cable, internet, trash removal and use of recreational facilities are included in the monthly fee. This well appointed move in ready condo has a large bright kitchen with lots of cabinets, great counter space, appliances and pantry closet. The kitchen overlooks the great room that also adjoins the additional bonus area and storage closet. The primary bedroom has a walk in closet & bathroom with a walk in shower. Beautiful views of Spring Lake can be enjoyed from the Primary bedroom & living areas. Washer/Dryer are included. Convenient to shopping, groceries & restaurants. Extra assigned storage bin on same floor. Lakeridge Condominiums is an age restricted, well maintained & well managed community.

1776 6th Street Nw Unit 807, Winter Haven
$59,999
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Co-Op Inc SubDv. ⋅ 33884 Zip Code
Under contract-accepting backup offers. Welcome to Orange Manor West in desirable southeast Winter Haven. This spacious 2-bedroom, 2-bathroom home offers comfort and functionality in a quiet neighborhood. The king-sized primary bedroom features dual walk-in closets and an ensuite bathroom with a new vanity sink installed in 2024. The second bedroom also boasts a closet door and easy access to the second bathroom with updated sink. Stylish new flooring was added in the kitchen, dining area, and both bathrooms in 2020. This fully furnished double-wide manufactured home is located in a 55+ gated community. Enjoy year-round comfort with a 2017 AC/furnace heat pump and a roof replaced the same year. Additional upgrades include a water heater installed in 2023 and a washer/dryer set from 2022. Relax or entertain in the air-conditioned bonus patio, perfect for Florida living. The community offers a wide range of amenities including a heated pool, shuffleboard, horseshoes, bingo nights, putt-putt golf, lake access and more. HOA fees conveniently cover cable, internet, trash, and all community amenities making this home an excellent blend of value and lifestyle in a welcoming active neighborhood. Convenient to shopping, hospitals, LEGOLAND, and both Tampa & Orlando International airports and area attractions.

128 Lake Hazel Drive, Winter Haven
$110,000
2 Beds ⋅ 2 Baths ⋅ Imperial Harbours SubDv. ⋅ 33880 Zip Code
Under contract-accepting backup offers. FIRST FLOOR BEAUTY! This move-in-ready 2 bedroom 2 bath condo is just what you've been waiting to find. 2025 was a big year with loads of quality updates in each room. The kitchen boasts updated quartz countertops, sparkling glass backsplash, sleek white soft close Shaker cabinets, and various stainless steel appliances. The stack washer/dryer is @1yr, and is tucked in next to the new hot water tank. Each bathroom has lovely upgrades including cabinets, tile, and luxurious sliding glass shower doors. You'll enjoy the neutral colors throughout, and the lush carpet (1yr) in the main areas will keep your toes cozy. There are 2 designated parking spaces, one covered. The Florida room has a nice walk-in-closet, and is a sunny space for reading or crafts. Imperial Harbours' reasonable monthly fee of $441.05 includes basic cable, water, sewer, garbage, exterior maintenance, and all community amenities. You only pay for your electric. Relax in the heated pool, enjoy fishing or sunrises from the community pier. Extra fun can be found on the shuffleboard courts, billiards room, and tidy exercise room. The convenient location is minutes to restaurants, grocery stores, and charming downtown Winter Haven. Call today for your private viewing. Step inside, fall in love. Make it yours!

333 Lake Howard Dr Nw Unit 102D, Winter Haven
$140,000
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates Add SubDv. ⋅ 33881 Zip Code
Welcome home to this beautifully maintained residence in the highly sought-after Lake-n-Golf Estates, where comfort, convenience, and an active lifestyle come together. From the moment you arrive, you'll appreciate the attractive epoxy-coated driveway and the inviting front sitting area, creating the perfect private retreat to enjoy your morning coffee or unwind with a good book. Step inside to a bright, vibrant interior featuring luxury vinyl plank flooring installed just a few months ago, offering a fresh, modern feel throughout the home. A brand new roof, less than one year old, provides added peace of mind for years to come. Outside, you'll also find a convenient storage shed, offering plenty of space for tools, hobbies, or seasonal items. Lake-n-Golf Estates is a resident-owned 55+ community known for its welcoming atmosphere and outstanding amenities, including a golf course, heated community pool, clubhouse, shuffleboard courts, and a full calendar of social activities. Conveniently located near shopping, dining, medical facilities, and Winter Haven's beautiful Chain of Lakes, this home offers the perfect blend of relaxation and everyday convenience. Come experience all that this wonderful home and community have to offer.

6666 Briarhill Drive Ne, Winter Haven
$189,900
2 Beds ⋅ 2 Baths ⋅ Winterset Garden Villas SubDv. ⋅ 33884 Zip Code
Welcome to 7902 Waterview Way, a beautifully maintained low-maintenance condo nestled within a desirable gated community. Offering a perfect blend of comfort and convenience, this home features tasteful upgrades, modern finishes, and a functional layout designed for easy everyday living. Enjoy a carefree lifestyle with exterior maintenance taken care of while taking advantage of the community's exceptional amenities, creating the perfect setting to relax or stay active. Ideally located near shopping, dining, entertainment, and major roadways, this move-in-ready condo offers the perfect opportunity to enjoy low-maintenance living in a secure and welcoming neighborhood.

7902 Waterview Way, Winter Haven
$36,950
2 Beds ⋅ 1 Baths ⋅ Bookers Sub SubDv. ⋅ 33881 Zip Code
Prime opportunity in Winter Haven — this is primarily a land value play. The lot features an older 1950 wood-frame home in need of significant work, giving buyers two clear paths forward: fully renovate the existing structure or clear the lot and build new. A new single-family home on this site carries an estimated ARV of $260,000, making this an ideal project for investors, builders, or renovators looking to add value in a growing area. Sold as-is — bring your vision and your contractor.

314 Avenue Y Ne, Winter Haven
$125,000
2 Beds ⋅ 3 Baths ⋅ Casa Del Sol Condo Village Ph 01 SubDv. ⋅ 33881 Zip Code
Priced to Sell — Bring Your Vision (and Your Toolbelt) Opportunity is knocking at 2500 21st St NW, #50 in Winter Haven, and it’s asking for someone ready to turn sweat into serious equity. This lake view property is priced well below its true value for the location and community the kind of deal that rewards buyers who see potential where others see a to-do list. Location is everything here: you’re right across the street from the community pool and clubhouse, and the community even features its own dock lakeside living at your doorstep. Step inside and you’ll find durable tile throughout the downstairs, with laminate flooring running up the steps and across the entire upstairs no carpet to worry about. The upstairs master bedroom comes with its own private balcony view of the lake from the balcony, the perfect spot to take in the surroundings. The kitchen shines with stainless steel appliances, solid countertops, and cabinets in great working condition. Yes, she needs some TLC: a little cleaning, a fresh coat of paint, and a new AC unit. But here’s the good part we already have an estimate from a reputable local company ready to install the unit with a warranty. The heavy lifting on the hardest fix is already scoped out for you. The home is vacant and virtually staged, so you can walk in with a blank canvas and picture your own finishing touches (furniture shown is virtual). Homes with this kind of upside, in this location, at this price, don’t sit long. If you’ve been waiting for the chance to build instant equity in a lakeside community steps from the pool, clubhouse, and dock this is it. Bring your imagination, roll up your sleeves, and make it your own. The community offers two pools (one is adult only), shuffleboard, tennis court, clubhouse and dock. Priced to sell. Move fast.

2500 21st Street Nw Unit 50, Winter Haven
$139,900
2 Beds ⋅ 2 Baths ⋅ Lake Kit SubDv. ⋅ 33884 Zip Code
Luxury condo design without the luxury price! Welcome to 626 Pavare Ct in Winter Haven, a beautifully updated 2 bedroom, 2 bathroom condo priced below market! Seller is motivated and ready to sell, making this an incredible opportunity for first-time buyers, down-sizers, or anyone looking for low-maintenance living without sacrificing style or amenities. Step inside to find a move-in ready home with LVP flooring throughout, a gorgeous kitchen featuring quartz counter tops, stainless steel appliances, a custom range hood, and stylish finishes that give the space a modern, elevated feel. All appliances are included, along with the like new washer and dryer, making this home truly ready to be lived in from day one. Enjoy the comfort and convenience of condo living with access to a community pool and a location close to shopping, dining, medical facilities, entertainment, and everything Winter Haven has to offer. Whether you are looking for your first home, simplifying your lifestyle, or searching for an affordable option with a designer touch, this condo checks all the boxes. Community occupancy guidelines require all occupants to be at least 14 years of age. Buyer and buyer?s agent to verify all community rules, restrictions, measurements, and information.

626 Pavare Court, Winter Haven
$159,900
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
CUTE AND COZY 2 BR/2 BA HOME IN GARDEN GROVE OAKS 55+ COMMUNITY! This one-owner home is in one of Winter Haven's most sought-after 55+ communities where you own your land, and the HOA is low at $65/month. You will not be bored living here...activities include dances, birthday and anniversary celebrations, water aerobics, card games, shuffleboard, billiards and more. The community has its own clubhouse, pool and spa, and optional secured RV/boat parking. You will find 6235 Knotty Pine Dr on a quiet cul-de-sac with little traffic.  The bright, open, and spacious floor plan features 1080 sq ft of living area, plus a Florida room, perfect for your morning coffee, relaxing and entertaining.  Inside laundry room located in the hall bathroom. Notable upgrades include NEW ROOF in 2023, NEW A/C in 2025, and a FULL HOUSE GENERATOR. With some cosmetic updates, you can add your final touches to make this home yours!  The home will be pressure washed prior to closing. The community is clean, and pride of ownership is displayed throughout. Florida living at a price you can afford with no lot rent. Conveniently located just a few minutes from Hwy 27, shopping, medical facilities, and restaurants.Schedule your private viewing today!

6235 Knotty Pine Drive Se, Winter Haven
$235,000
2 Beds ⋅ 1 Baths ⋅ Tranquility Park Sub SubDv. ⋅ 33880 Zip Code
Welcome home to this adorable 2 bedroom/ 1 bath residence, centrally located in beautiful Winter Haven. Perfect for a first-time home buyer, this charming home offers numerous updates, including a newer metal roof (2023), newer HVAC, complete replumbing (2026), newer vinyl flooring and fresh new interior and exterior paint. Step outside and enjoy the spacious, fully fenced backyard providing privacy and the perfect retreat for pets, entertaining, or simply relaxing. Conveniently located just minutes from downtown Winter Haven and the Polk Parkway, with easy access to both Tampa and Orlando. Don't miss out on a chance to own this charming home. Schedule your private showing today.

1365 Sheridan Street Sw, Winter Haven
$205,000
2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
Fully remodeled 2-bedroom, 1-bath home in the heart of Winter Haven. This move-in-ready property features a new roof, updated electrical and plumbing, and modern finishes throughout. Situated on a spacious lot with no HOA, it offers both comfort and flexibility. Conveniently located near major roads, shopping, dining, schools, and just minutes from downtown Winter Haven and LEGOLAND Florida Resort, making it an excellent option for homeowners or investors.

3420 Avenue R Nw, Winter Haven
$150,000
2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
Under contract-accepting backup offers. Investor special in the heart of the Inwood neighborhood — solid block construction, new roof (2024), and a location that puts you minutes from everything Winter Haven has to give. This two-bedroom (possibly could be a 3 bedroom), one-bath home sits on a fenced lot with mature shade trees, and the covered, screened front porch gives the place a real homey feel the moment you pull up. Inside you'll find ceramic tile throughout the bedrooms and living areas, ceiling fans in every room, and a converted single-car garage that works well as an additional bedroom or possibly a den, home office, or storage space. The layout is straightforward and functional — living room, eat-in kitchen, two bedrooms with built-in closets, and a full bath with pedestal sink and tiled shower. There's also a linen closet in the hall. A shed out back adds extra storage. And the size of the backyard allows for endless possibilities. The home currently has window AC units but no central air or heat system — a definite opportunity for a buyer to update to their preference and immediately add equity. Dual septic system on site. Water is public. The property is being sold as-is. Convenient to US-17, shopping, dining, Polk State College, the Chain of Lakes trail system, and downtown Winter Haven. No HOA. Great bones, priced to move.

3319 Avenue U Nw, Winter Haven
$225,000
2 Beds ⋅ 1 Baths ⋅ Inwood SubDv. ⋅ 33881 Zip Code
Welcome to your private backyard paradise! This beautiful home features two bedrooms, one bath, no HOA, a relaxing jacuzzi spa, functional greenhouses for gardening, storage sheds, irrigation system and a rare, gated private alley at the rear of the property which provides convenient access to your backyard. The property is currently an active plant nursery and the sale includes everything to continue that if you choose. Inside you will find an open layout perfect for comfortable living. Enjoy total peace of mind with newer appliances, windows (2026), electrical wiring (2025), HVAC (2025) and also an indoor laundry space. This property is conveniently located five minutes from downtown Winter Haven, near dining and shopping, close to the Chain of Lakes, Legoland and many parks and outdoor activities. If your looking for the Florida lifestyle then come tour this unique property.

1405 28th Street Nw, Winter Haven
$125,000
2 Beds ⋅ 2 Baths ⋅ Orchid Spgs Vill 200 Condo SubDv. ⋅ 33884 Zip Code
Under contract-accepting backup offers. Welcome to the Seville Building at Orchid Springs, a serene 52-unit condominium community! This move-in ready, ground-floor 2-bedroom, 2-bath condominium features a freshly painted interior and is located in a building with a new roof (2024), offering added value and peace of mind. Enjoy the convenience of single-level living and relax on your rear lanai overlooking a peaceful pond—an ideal setting for your morning coffee or unwinding at the end of the day. Orchid Springs is one of Southeast Winter Haven's most established condominium communities, known for its mature oak trees, lush landscaping, tranquil ponds, and quiet atmosphere. Residents enjoy a low-maintenance lifestyle in a beautifully maintained community. The monthly HOA fee includes water, sewer, trash, gas, community pool, exterior maintenance, and common area maintenance, making homeownership simple and convenient. Ideally located just minutes from Winter Haven's renowned Chain of Lakes, you'll enjoy easy access to boating, fishing, waterfront parks, golf courses, Winter Haven Hospital, LEGOLAND Florida Resort, shopping, dining, and entertainment along Cypress Gardens Boulevard. Convenient access to the Polk Parkway makes commuting to Lakeland, Orlando, and Tampa a breeze. Whether you're looking for a full-time residence or a seasonal retreat, this well-maintained condo offers the perfect combination of comfort, convenience, and the relaxed Florida lifestyle. Schedule your private showing today!

200 El Camino Drive Unit 111, Winter Haven