Winter Haven Condos For Sale - 62 condos

Remarks: 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, 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.

Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)

Listing Agent: Amy Sullivan (863-280-3633)

Remarks: Welcome to this 2-bedroom, 2-bathroom ground-floor condo in the desirable Lake Buckeye community. This home features a bonus room and includes the washer and dryer for move-in ease. Step inside and enjoy seamless indoor-outdoor living with a cozy open patio off the dining area. The community enhances your lifestyle with amenities such as a sparkling pool, fishing pier, dock all while showcasing tranquil views of Lake Buckeye that make every day feel like a retreat. Ideally located just minutes from Polk State College, Winter Haven Hospital, Bond and Gessler Clinics, and the lively downtown of Winter Haven, you’ll enjoy easy access to dining, breweries, shopping, the farmers market, and seasonal events. Publix and the Diamond plex sports complex are less than 10 minutes away, Legoland Resort is only 15 minutes, and world-class attractions like Walt Disney World and Universal Studios are about an hour’s drive. With leasing permitted and no age restrictions, this property is an excellent choice for both homeowners and investors. Don’t miss your chance to make it yours.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Brian Cox (863-559-3627)

Remarks: Here we go, back to market, Buyer default! The property you are inquiring about is located in Winter Haven, FL, in the Winter Haven Harbour area of Polk County. Now conveniently located is this corner unit with beautiful window views from the third floor, and with recent updates. Two bedrooms, 1 bath, with every square inch utilized for practical purposes. The community is a 55+ and is conveniently located in the heart of convenience. The HOA fees are low by comparison to what is included in the fee. Vacant and ready for occupancy. Text or call for your private viewing. *Agents, please read MLS remarks.*

Listing is courtesy of: BROKERS REALTY OF CENTRAL FLOR (863-294-6773)

Listing Agent: Renee Butler (863-294-6773)

Remarks: One or more photo(s) has been virtually staged. Welcome to maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. This 3rd floor 2-bedroom, 2-full-bath condo offers the relaxed lifestyle many buyers look for, complete with elevator access for easy entry. You are greeted by views of the community pool and cabana area right from your front entrance, while the interior features a bright Florida Room and a relaxed lakeside atmosphere. Best of all, the monthly HOA fee covers everything except your electric bill, making your budget completely stress-free. Enjoy premier amenities like a private boat ramp and fishing pier right on Winter Haven's popular Chain of Lakes. Located just across the water from downtown shopping and dining, this well-established, owner-occupied neighborhood is ready to welcome you home to a truly wonderful community lifestyle!

Listing is courtesy of: REGAL REAL ESTATE LLC (863-660-7927)

Listing Agent: Natalie Elson (863-709-3516)

Remarks: One or more photo(s) has been virtually staged. Short Sale. Back on the market with renewed opportunity! Enjoy peaceful lakefront living in this beautiful updated 2 bedroom, 2 bath condo located in the gated Winterset community. Featuring an open floor plan granite countertops, stainless steel appliances, upgraded cabinetry, and a cozy breakfast nook, this home offers both comfort and style. The enclosed balcony showcases stunning views of Garden Lake, perfect for quiet mornings or relaxing evenings. Recent updates include plumbing, electrical, lighting, bathroom vanities, and updated flooring throughout, making this home truly move-in ready. Winterset offers resort - style amenities including pool, spa, clubhouse, tennis and pickleball courts, and a private lakefront pier. Conveniently located just minutes from LEGOLAND and under an hour to Orlando attractions. Short sale- priced in alignment with lender expectations. A great opportunity for buyers looking for value, a primary residence, or an investment property.

Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)

Listing Agent: Valerie Howze (863-604-9080)

Remarks: Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second bedroom adjacent to guest bathroom with tub/shower, and a versatile 7' x 23' Florida room perfect for home office, hobbies, or relaxation. The all-inclusive condo fee covers cable TV, internet, water, sewer, trash removal, building maintenance (exterior, roof, insurance), reserve funds, common area upkeep, on-site management, and access to all community amenities including swimming pool, exercise room, recreation room with kitchen, library, game area, shuffleboard, laundry facilities, and active social calendar with enhanced security features. Situated on the "Chain of Lakes" for fishing, boating, and water activities with boat slips available for a reasonable fee (verify with management), this property boasts a rare assigned covered parking space in close proximity to the unit and is adjacent to Northgate shopping plaza featuring Publix, restaurants, and services, minutes from medical facilities, Winter Haven Hospital, places of worship, and downtown. No pets or smoking permitted. This perfect full-time residence or seasonal retreat (measurements approximate, information believed accurate but not guaranteed).

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Kevin Tison (863-206-5755)

Remarks: Wake up to views of Lake Howard and enjoy maintenance-free Florida living in the peaceful 55+ community of Imperial Harbours. From the bright Florida Room to the lakeside atmosphere and community amenities, this condominium offers the relaxed lifestyle many buyers move to Florida to find. Conveniently located less than 25 feet from the elevator, this furnished 2nd story condominium features a spacious great room, open dining area, and a pass-through window connecting the kitchen to the main living space. Natural light fills the home, highlighting the laminate and tile flooring throughout. The primary bedroom easily accommodates a king-sized bed with room for additional furniture and offers views of the community pool and cabana area. The en-suite bathroom includes a walk-in closet and walk-in shower. The second bedroom is across the hall from the main bathroom and primary bedroom. The Florida Room gives you pool and cabana views with sliding glass door separating it from the Great Room. Imperial Harbours amenities include a community pool and cabana, shuffleboard courts, fishing pier on Lake Howard, extra storage space, and a reserved covered parking spot. Lake Howard is part of Winter Haven’s famous Chain of Lakes, and downtown Winter Haven is located just across the lake for convenient access to shopping, dining, entertainment, and local events. Enjoy low-maintenance living, scenic surroundings, and the comfort of a well-established owner-occupied community with no leasing allowed.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Ryan Odenweller, Llc (863-271-7882)

Remarks: Under contract-accepting backup offers. Hidden gem with upgrades you won’t expect! First-floor condo for easy access and numerous updates throughout. The kitchen features a new backsplash, new sink and faucet, freshly painted cabinets, and newer appliances, including the refrigerator and dishwasher. A new water heater adds additional peace of mind. Both bathrooms have been updated with new vanities, faucets, and tile backsplashes. Custom wood shelving has been installed throughout the home—no wire shelving—along with custom closet organizers in both bedrooms. The spacious primary bedroom features beautiful plantation shutters. Stylish barn doors enclose the laundry area with a washer and dryer, and the hall closet. Covered parking included. Situated on scenic Lake Howard, part of the famous Winter Haven Chain of Lakes, this community offers boat dock access. Residents also enjoy a sparkling pool, gazebo with grilling area, shuffleboard courts, and a quiet, secure atmosphere. Even better, the HOA covers cable, internet, water, sewer, trash, exterior maintenance, and lawn care—you only pay for electricity. Truly affordable, maintenance-free Florida living.

Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)

Listing Agent: Nancy Cini (727-612-0375)

Remarks: This is a beautiful condo located in the heart of Downtown Winter Haven, FL. The sunsets over Lake Howard are unbelievably gorgeous and can be enjoyed sitting on either patio overlooking the waterfront. This is an end unit that comes with 2 covered parking spaces located directly underneath the space. A must see.

Listing is courtesy of: COLLANY PROPERTIES (863-295-9886)

Listing Agent: Christopher Collany (863-412-2170)

Remarks: Under contract-accepting backup offers. Welcome to 333 Lake Howard Dr NW, Unit 313A — a beautifully updated 2-bedroom, 2-bath condo located on the top (3rd) floor of a well-maintained 55+ community. The building offers elevator access and is wheelchair accessible, providing both comfort and convenience. This move-in ready unit features large windows in the living room overlooking the community pool, filling the space with natural light and offering peaceful views. Recent updates include all new kitchen cabinets and countertops, a new lanai cabinet, upgraded bathrooms, a new walk-in shower, new carpet throughout, fresh interior paint, new light fixtures, and new vent covers. The roof has also been replaced, adding additional value and peace of mind. Residents enjoy a variety of amenities including a community pool, fitness center, and direct lake access to Lake Howard. The private dock and boat parking make it easy to enjoy fishing, relaxing by the water, or docking your boat — all included in the HOA dues. Additional features include assigned covered carport parking and a 4x4x4 extra storage space located on the 2nd floor. Enjoy low-maintenance living with resort-style amenities in a prime location.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Brian Cox (863-559-3627)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 1361SF 2BR/2BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon/pond views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedrooms enjoy extra windows with peaceful courtyard views. The primary bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. Both bathrooms are well-appointed, with one offering a custom vanity and a tub/shower combo. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Sharon Gastelbondo (863-800-4655)

Remarks: Top-floor condo with INCREDIBLE lake views in the desirable 55+ community of Imperial Harbours on Lake Howard! This three-bedroom, two-bath condo offers tons of potential and is ready for your personal touches and a little TLC. The kitchen features a convenient pass-through window overlooking the dining and living areas, creating an open and functional layout. The spacious primary suite includes an en suite bathroom and walk-in closet, while bedrooms two and three share a second full bath. A small bonus room overlooks the lake and would make a great office, sitting room, or hobby space. This beautifully maintained waterfront community offers maintenance-free living with access to a private dock and fishing pier on the famous Chain of Lakes. Amenities include a community pool and cabana, shuffleboard courts, extra storage, covered parking, and elevator access. Association dues cover cable, internet, water, sewer, trash, exterior maintenance, and grounds care. Conveniently located near downtown Winter Haven, shopping, dining, and medical facilities. Call today to schedule your private showing!

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Cute as a Button! Charming 1-Bedroom, 1-Bath Condo in the desirable Park Lake community. This bright and inviting home features easy-care laminate flooring throughout, a cozy wood-burning fireplace, and a functional dinette area with a breakfast bar that flows into the dining space. Enjoy lots of Hot Water with the Natural Gas Tankless Hot Water Heater. The convenient stackable washer and dryer are included, making move-in a breeze. Step outside to enjoy your private screened-in porch — perfect for relaxing with your morning coffee or unwinding in the evening. Ideally suited for first-time homebuyers, investors, or anyone seeking low-maintenance living in a prime location, this condo is situated right in the heart of Winter Haven. The Park Lake community offers an abundance of amenities, including a sparkling community pool, direct lake access, clubhouse, fishing pier, exercise room, and more. Located on the shores of beautiful Lake Lulu, Park Lake is conveniently positioned next to the new AdventHealth Field House. You’re also just minutes from LEGOLAND, with quick access to the Disney and Universal entertainment areas. Excellent medical facilities and shopping are nearby as well. All measurements are approximate. Buyers and Buyers’ Agents to verify all listing information. Call today to schedule your private showing!

Listing is courtesy of: LAMOND REALTY INC. (863-875-8910)

Listing Agent: Robert Lamond (863-604-5400)

Remarks: Discover this charming first-floor corner unit condo in the highly sought after Orchid Springs community in SE WInter Haven. This 2 bedroom 2 bathroom condo features a desirable split floor plan with an oversized living area perfect for entertaining or relaxing. Both bedrooms boast generous walk-in closets , and offers abundant storage throughout. Enjoy the convenience of a first floor corner location with a covered parking spot. The nice open layout makes every day maintenance free living easy and comfortable. Residents of Orchid Springs love the prime location minutes from shopping,dining, medical facilities, and Legoland, while being centrally situated between Tampa and Orlando for easy access to everything Central Florida has to provide. The HOA takes care of the details including grounds maintenance, water , sewer and gas giving you more time to enjoy the Florida Lifestyle. Whether you are looking for a primary residence or a winter retreat , this first floor corner unit is a fantastic opportunity in a desirable community. Schedule your showing today and make this condo your new home!

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Rosalia Abreu (954-854-3694)

Remarks: A Cozy Condo nestled in the back corner of the popular community of Winterset. Forgot your key, no problem, you have a coded keyless entry. Your tour begins entering through your covered screened front porch into a Ground level 2 bed/2bath home with an open floor plan. Beautiful Laminate wood flooring accentuates the space. The conveniently centered kitchen boasts a neutral decor with tile backsplash and a newer Stainless side by side fridge. A Nice size Patio is accessed from Livingroom for Barbecuing or just relaxing, enjoying the Florida weather. The split bedroom design offers added privacy to The Master Bedrm with en suite, spacious Walkin closet, Stackable washer/dryer and private screened in patio area which continues to enhance this space. The master bath has separate tub/shower access. The Nest thermostat allows you to monitor and change settings via a phone app. When you Plan your day trips.... You're Only minutes from Lego Land and convenient to Disney & other Florida amusement parks, Beaches, Shopping, Restaurants & More. Or, stay at home, relax and enjoy amenities of the community with Heated Pool, Spa, Tennis, Shuffleboard, Fishing Pier and Clubhouse! Walk the family pet across the street in the expansive green space. All Furniture negotiable!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Catrina Marshall (813-377-7380)

Remarks: Under contract-accepting backup offers. This charming 2-bedroom, 2-bath condo offers the perfect blend of comfort and convenience with a layout designed for effortless living. Enjoy a spacious living area, light-filled interiors, and a private outdoor space perfect for morning coffee or evening wind-downs. Located just minutes from Winter Haven’s famous Chain of Lakes, local dining, shopping, and everyday essentials, this is the ideal spot for year-round living, a seasonal retreat, or a smart investment. Low maintenance. Prime location. Relaxed lifestyle. *This home can be purchased with NO INCOME VERIFICATION*

Listing is courtesy of: ENGEL & VOELKERS LAKELAND (863-412-6633)

Listing Agent: Donna Fiore (904-228-0198)

Remarks: Beautiful lakefront living awaits in the gated community of Winterset! This beautifully maintained 2-bedroom, 2-bathroom condo with an attached one-car garage offers stunning lake views, abundant natural light, and unique architectural details throughout. Inside, you’ll find beautiful cork flooring, specialty tray ceilings, and a cozy library area complete with custom built-in shelving. The spacious enclosed Florida room is a true showstopper, featuring floor-to-ceiling windows overlooking the lake, creating the perfect space to relax and enjoy breathtaking water views year-round. The oversized primary suite offers a spacious layout with dual sinks, a walk-in closet, and a peaceful retreat-like feel. The large custom kitchen is a chef’s dream, complete with a gas stove, ample cabinetry, generous counter space, and plenty of storage for all your culinary needs. Enjoy the beautiful community amenities that include a pool, tennis courts, and the security and privacy of this sought-after gated neighborhood. Conveniently located near Legoland, shopping, dining, and everyday conveniences. This lakefront condo perfectly blends comfort, elegance, and Florida lifestyle living.

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Jill Lingenfelter (863-242-0900)

Remarks: LAKEFRONT LIVING AT IT'S BEST! REFRESHED FIRST FLOOR 2BR-2BA CONDO WITH COVERED PARKING AND BEAUTIFUL VIEWS OF LAKE BUCKEYE. THE FEATURES INCLUDE FRESH INTERIOR PAINT, LUXURY VINYL PLANK FLOORING THROUGHOUT WITH CERAMIC TILE IN THE BATHROOMS, KITCHEN AND FLORIDA ROOM, STAINLESS REFRIGERATOR AND MICROWAVE IN THIS CONVENIENT KITCHEN WITH PANTRY AND PASS THRU EATING COUNTER. THIS OPEN GREAT ROOM DESIGN HAS LIVING AND DINING COMBO. RELAX IN YOUR FLORIDA ROOM OVERLOOKING THE LAKE AND ENJOYING THE SUNRISE WITH YOUR MORNING COFFEE. COMMUNITY OFFERS POOL AND TENNIS COURTS. CONVENIENT LOCATION , WALK TO POLK STATE COLLEGE OR ENJOY THE WALKING TRAIL AROUND LAKE ELBERT ONLY MINUTES AWAY WITH NEARBY DOWNTOWN SHOPPING AND RESTAURANTS.

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)

Remarks: Welcome to this charming and updated, move-in ready 2-bedroom, 1.5-bath condo nestled right on Cypress Gardens Blvd in Winter Haven — just minutes from world-class shopping, dining, and the famous LEGOLAND Florida Resort! This well-maintained two-story unit has been tastefully updated throughout. Rich dark luxury vinyl plank flooring flows through the spacious living areas, giving the home a modern, cohesive feel. The kitchen is fully equipped with rich wood cabinetry, stainless steel appliances including a dishwasher, range, and refrigerator, and tile flooring — with a sliding glass door that brings in great natural light. A convenient half bath on the main level is fully updated with a new vanity and brushed nickel fixtures. Upstairs you'll find two generously sized bedrooms. The dedicated laundry closet plumbed and ready for your washer and dryer is on the first floor. The classic brick exterior and covered front porch add great curb appeal and a welcoming first impression. Whether you're a first-time buyer, downsizer, or investor looking for a rental in a high-demand location, this one checks all the boxes. Schedule your showing today — this one won't last!

Listing is courtesy of: HAVEN REALTY & INVESTMENTS (863-333-5053)

Listing Agent: Vincent Reina (863-398-6243)