Winter Haven Condos For Sale - 55 condos

Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Casandra Vann (863-546-5446)

Remarks: Under contract-accepting backup offers. PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings. Inside, you'll love the bright, open layout with 10' ceilings, rich wood cabinetry, and a breakfast-bar kitchen—ideal for casual meals, morning coffee, or entertaining. Both bedrooms feature spacious walk-in closets, plus you'll appreciate the extra outdoor storage for bikes, golf gear, and more. Enjoy the benefits of a low HOA that covers exterior maintenance, landscaping, pest control, and trash, along with access to the community pool and tennis courts. Cypresswood residents also enjoy resort-style amenities, including an 18-hole Ron Garl-designed golf course, clubhouse, restaurant, and junior Olympic pool. Ideal for first-time buyers, families, professionals, golf enthusiasts, seasonal residents, or investors seeking a turnkey rental in a premier gated community. Prime location: Minutes to I-4 and Hwy 27 for easy commuting. Close to LEGOLAND, Bok Tower Gardens, shopping, dining, medical facilities, and entertainment. Centrally located between Tampa and Orlando—the best of Central Florida at your doorstep. Don't miss this opportunity! Pond-view units in Cypresswood are highly desirable and move quickly. Schedule your private showing today and see why Cypresswood is such a wonderful place to call home.

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

Listing Agent: Mabel Vassallo (863-604-0499)

Remarks: This move-in-ready home features fresh interior paint, updated countertops, brand-new cabinets, and renovated bathrooms, offering a clean, modern feel throughout. The open-concept floor plan creates a bright and inviting living space, perfect for entertaining or relaxing. Upstairs, a versatile loft provides the ideal spot for a home office, guest area, or flex space to fit your lifestyle. Enjoy low-maintenance living with fantastic community amenities, including a sparkling pool and lake access — perfect for soaking up the Florida sunshine. Ideal for first-time homebuyers, investors or anyone looking for comfort, convenience, and location all in one, this condo offers the perfect blend of style and lifestyle in the heart of Winter Haven. Some photos have been virtually staged to illustrate the property’s potential. Furnishings, décor, and enhancements shown in staged images are for marketing purposes only.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Marquita Smith (863-289-3343)

Remarks: 55+ PLUS COMMUNITY! Corner unit! Features granite countertops, marble kitchen flooring, and wood laminate floors throughout the living room, dining area, and hallway. Interior utility area includes washer and dryer for extra convenience. The primary bedroom opens to a screened-in balcony. This amenity-rich community offers a large heated pool, pickleball and shuffleboard courts, a grilling area, and a clubhouse with a fitness center, perfect for staying active or socializing with neighbors. Additional conveniences include a common laundry room, a secure storage area, reserved covered parking, and elevator access. Ideally located in central Winter Haven, this condo is just minutes from downtown, shopping, dining, hospitals, and medical facilities, with easy access to I-4, placing you perfectly between Orlando and Tampa. Enjoy a vibrant lifestyle in a prime location.

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

Listing Agent: Rosa Suarez (954-682-2633)

Remarks: Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy and a peaceful feel while enjoying the security and convenience of community living. Inside you will find updated luxury vinyl flooring, windows, stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer and AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath condominium. It's located in the highly sought-after 55+ Imperial Harbor community of Winter Haven. Convenient elevator access makes daily living effortless in this serene lakefront retreat. Start your mornings with a walk to the private community dock on Lake Howard, where fishing and boating await. Enjoy an array of resort-style amenities, including a heated pool, fitness center, shuffleboard, and billiards, all designed to support an active and relaxed lifestyle. Ideally situated just 45 minutes from both Tampa and Orlando, this central location offers the perfect balance of tranquility and accessibility. Inside, the open and airy floor plan feels inviting and relaxing. Refinished cabinets, fresh paint throughout and new double pane insulated windows make this home move-in ready! The primary suite is bright and spacious and two additional bedrooms provide flexibility for guests, hobbies, or a home office. An in-unit laundry closet with washer and dryer adds everyday convenience. HOA fees also include water, basic cable, and internet—making this an exceptional opportunity for low-maintenance, carefree living. Schedule a private tour today !

Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)

Listing Agent: William Kilpatrick (863-669-8090)

Remarks: Enjoy effortless living in this beautifully updated condo perched on the 8th floor, offering breathtaking views of Spring Lake. This spacious residence features 2 bedrooms and 2 bathrooms, including a master suite with a walk-in closet and private bath. The custom kitchen is a standout with granite countertops, wainscoting ceiling, and a convenient bar, complemented by updated appliances and a new LG washer/dryer tower. Flooring includes ceramic tile, laminate, and cozy carpet in the bedrooms, while new windows with motion solar shades bring in natural light and comfort. Located in a desirable 55+ gated community, residents enjoy resort-style amenities including a heated pool, tennis courts, shuffleboard, and a welcoming social room with kitchen. Additional conveniences include 2 elevators, a covered parking space, and monthly fees that cover water, cable, internet, and community amenities.

Listing is courtesy of: NEXTHOME NORRIS & COMPANY REAL (863-875-5583)

Listing Agent: Michael Norris (863-287-3105)

Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.

Listing is courtesy of: WF REALTY CORP. (407-994-2900)

Listing Agent: Adriana Sanchez (321-947-4014)

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: 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: Welcome to this 2-bedroom, 1.5-bath condo in the desirable 55+ community of Winter Haven Harbour Apartments! This beautifully updated unit is modern, stylish, and completely move-in ready. Inside, the condo has been freshly painted and features luxury vinyl plank flooring in living areas and tile in kitchen and baths. Both bathrooms have been fully redone with modern finishes. The main bath features granite countertops and a stand-up shower with a built-in seat for added comfort and accessibility. The updated kitchen offers ample cabinetry and storage, Granite counter tops, plus the added bonus of a washer and dryer all-in-one unit — a huge perk for condo living. Important updates include a 2021 water heater and all new storm windows installed last year. An additional bonus is the private storage closet located next to the elevator; approximately 4x6 feet with floor-to-ceiling space. This active 55+ community offers a welcoming community center complete with a fitness center, library, and pool table. Outside near the heated pool, you’ll find a beautiful friendship garden with seating and a fire pit — the perfect spot to relax or gather with neighbors. Residents also enjoy pickleball courts, shuffleboard, and a grilling area ideal for social events and sunny Florida afternoons. Conveniently located near shopping, dining, medical facilities, and positioned between Tampa and Orlando. If you’re looking for updated, modern living in a vibrant and friendly 55+ community, this top-floor gem checks all the boxes. Schedule your private showing today!

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

Listing Agent: David Small (407-601-8351)

Remarks: Cozy 2 bedroom 2 bath home with great view of Lake Howard off the master bedroom and patio. Turn around and look out of the front door with a beautiful view of the pool and patio areas. Rood is new this year with all damage from last year's storm repaired. This home is in move-in condition.

Listing is courtesy of: CHOICE PROPERTIES OF CENT FL (863-299-6710)

Listing Agent: Jane Tyl (863-224-1779)

Remarks: One or more photo(s) has been virtually staged. Pictures of plants are staged. LISTED BELOW APPRAISED VALUE!!! Welcome to 626 Pavare Ct, a charming completely remodeled 2-bedroom, 2-bath end unit condo located in the desirable Orchid Springs community. Step inside this 823 sqft second-level residence, where an open floor plan welcomes you with luxury vinyl flooring and soothing neutral paint tones. The living room effortlessly flows into the dining area and kitchen, creating an ideal setting for daily living. The kitchen is well-equipped with a like new range, brand new refrigerator, and like new stackable washer/dryer, elegant tile backsplash, deep sink with island all and bar stools. The primary suite offers a walk-in closet and an ensuite bath with a brand new walk-in shower, while the secondary full guest bath features a brand new tub/shower combo both with sliding glass doors. Condo is elegantly equipped beautiful gold finished faucets, large head showers, and heated/lighted mirrors in both bathrooms. Step out onto the private balcony and enjoy relaxing views of the landscaped grounds. Residents have access to a sparkling community pool, perfect for hot summer days. An assigned parking spot is conveniently located near the condo, and a guest parking spot is also included. Orchid Springs offers a convenient location with easy access to nearby shopping, dining, entertainment, medical facilities, and major transportation routes to Tampa and Orlando. The monthly condo fees of $284 covers ground, exterior building maintenance, and community amenities. The community welcomes a pet and residents over the age of 14, with annual rentals allowed. Whether you're looking for a starter home, a retirement retreat, a secondary residence, or an investment property, this condo has it all. Don't miss out on this opportunity! There is a clubhouse that is available for rent for special events! Call today to schedule a private tour and make this condo your new home.

Listing is courtesy of: TRUE FLORIDA REALTY LLC (863-337-9667)

Listing Agent: Misty Mcteer (863-557-0641)

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: Under contract-accepting backup offers. Buyer defaulted, check out this great value. The property you are inquiring about is located in Winter Haven, FL, in the Orchid Springs area of East Polk County. This is a 2nd-floor unit in Orchid Springs that is ready to move into NOW! The home has fresh paint throughout and brand new carpet. This is a one-bedroom, open floor plan with most of all utilities bundled in the HOA fees - to include - community pool, gas, exterior maintenance, maintenance grounds, water, sewer, trash. It has an approximate of 1,078 square feet of living, a dedicated parking space, and a common laundry area. Great with overlooking the preserve of nature's own form and the extremely quiet area of the Orchid Springs compound. Text, call, or email for 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: 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: Welcome Home to Orchid Springs Village! Step into comfort with this inviting 1-bedroom, 1.5-bath condo located on the second floor of the peaceful Orchid Springs 55+ community. Surrounded by mature landscaping, this residence offers a quiet and comfortable setting, ideal for those looking to enjoy a relaxed Florida lifestyle. You’ll appreciate being conveniently close to shopping, dining, medical facilities, Winter Haven Hospital, US Hwy 27, and I-4. The monthly HOA fee covers water, sewer, trash, natural gas, lawn maintenance, grounds upkeep, and use of the community room, allowing for easy, maintenance-free living. An assigned parking space is included, and one pet is welcome with HOA approval (size and breed restrictions apply). Buyer approval is also required by the HOA. Whether you’re searching for a year-round home or a seasonal retreat, this well-maintained condo at Orchid Springs Village offers comfort, convenience, and a welcoming community atmosphere.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Scott Cohara (407-398-9554)

Remarks: CORNER UNIT WITH VAULTED CEILINGS AND PRIVATE BALCONY- Welcome to your new retreat in the highly sought-after chain of lakes community of Park Lake — where comfort, style, and location come together beautifully. Step inside this charming one-bedroom, one-bath home and you’ll immediately notice the open feel created by vaulted ceilings and luxury vinyl flooring throughout the main living areas. The kitchen is a true highlight, featuring quartz countertops, sleek cabinets, stylish backsplash a modern tile floor, and all-new stainless steel appliances — including a five-burner stove, low-profile microwave, and refrigerator with exterior ice-maker. Thoughtful upgrades like new sinks, faucets, a garbage disposal, and modern lighting add both function and sophistication. The bathroom feels spa-like with a sleek tile shower, coordinating tile floor, quartz countertop, new sink, fixtures, and an elegant multi-illuminating with anti fog mirror that provides perfect lighting for any time of day. Two sliding glass doors — one from the living room and another from the bedroom — open to your private screened balcony, filling the home with natural light and offering peaceful outdoor views. The spacious bedroom includes a large closet, providing plenty of storage. This home also features a 2026 hot water heater, 2021 roof, and 2017 AC- offering peace of mind for years to come. Updated blinds, modern ceiling fans, and an inside utility with a washer/dryer combo add even more comfort and convenience. Just five minutes from vibrant downtown Winter Haven and next door to the state-of-the-art Advent Health Field House — complete with basketball courts and an Olympic-size swimming pool — this home’s location can’t be beat. Park Lake sits on the shores of beautiful Lake Lulu, where residents can fish from the pier or enjoy skiing right on the water. Perfectly centered near shopping, dining, and grocery stores, this prime location truly offers it all — comfort, convenience, and the best of the Florida lifestyle. Listing agent is owner.

Listing is courtesy of: LIONHEART BROKERS (321-214-4640)

Listing Agent: Claudia Centesimo (407-383-8882)

Remarks: NEW PRICE, JUST REDUCED!!! IMMACULATE GROUND FLOOR EAGLE POND CONDO located in desirable Cypresswood Golf & Country Club!!! Don’t miss your chance to own this charming 2-bedroom, 2-bathroom ground-floor condo in the highly sought-after, gated Cypresswood Golf & Country Club community. Perfectly maintained, this move-in-ready home features an open-concept living area, walk-in closets, interior laundry, and serene pond views. The spacious master bedroom includes an en-suite bathroom, while both bedrooms boast generous walk-in closets. Enjoy added storage with linen closets in both the master and hallway, plus an extra storage closet outside. The well-equipped kitchen boasts abundant cabinetry, ample counter space, a breakfast bar, pantry, and an inviting eat-in dining area. Relax on your private patio!! Ideal for seasonal living, rental income, or year-round comfort. Cypresswood's amenities include 24-hour gated/guarded security, an 18-hole championship golf course, junior Olympic-sized pool, walking trails, clubhouse, tennis courts, and restaurant. Just minutes from Highway 27, I-4, LEGOLAND, and a variety of dining, shopping, and entertainment options. Hurry and schedule a showing today!

Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)

Listing Agent: Cathy Kluytenaar (863-604-6220)

Remarks: Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)