Winter Haven Condos For Sale - 65 condos

Remarks: Under contract-accepting backup offers. Virtually Staged. Introducing a beautifully renovated 2-bedroom, 2-bath condo located on the lakefront of Lake Howard in Winter Haven. This top-floor unit is truly turnkey, offering updated flooring, fresh paint, new drywall, new interior doors, updated kitchen cabinets, and modern appliances. Recent upgrades include energy-efficient double-hung windows, a newer A/C system, and a stackable washer and dryer. The top-floor location provides added privacy with no neighbors above, while elevator access makes daily living easy and convenient. Enjoy relaxing lake breezes and beautiful Lake Howard views within this community in addition to the peaceful pool view from the unit. Community amenities include a pool, shuffleboard, and organized activities. Covered parking and onsite storage lockers are also included. This mint-condition condo offers comfort, convenience, and lakefront living with a low condo association fee in a 55 and older setting. A rare opportunity in a desirable Winter Haven location.

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

Listing Agent: Joshua Taylor (863-651-5471)

Remarks: Beautiful lake-view condo in Winterset! This ground-floor 2-bedroom, 2-bath residence offers amazing views of Lake Winterset, part of the renowned Winter Haven Chain of Lakes. The spacious great room features tile flooring, sliding glass doors to the screened porch, and stunning lakefront vistas. Just off the kitchen is a comfortable dining area, creating an inviting space for everyday living and entertaining. The kitchen is beautifully appointed with custom Kraft Maid wood cabinetry, granite countertops, a breakfast bar, and a complete appliance package. The primary bedroom enjoys peaceful lake views and includes plush carpeting with a gel pad, a large 11' X 7' walk-in closet, a ceiling fan, sliding doors to the patio, and an en-suite bath featuring dual sinks, quartz countertops, and an oversized walk-in shower with a seamless glass door. The guest bedroom is generously sized at 13' x 10', offering ample closet space and convenient access to the guest bathroom, which features quartz countertops and tile flooring. The screened porch is the perfect place to relax and enjoy breathtaking lakefront views and spectacular sunsets. Residents enjoy true resort-style living with access to a community clubhouse, pool, spa, shuffleboard courts, tennis & Pickleball courts. The highly desirable location offers close proximity to shopping, dining, schools, medical facilities, and LEGOLAND Florida Resort. Additional features include a private storage room off the patio, inside laundry, a tile roof, air conditioning, 24-hour security, meticulously maintained grounds, assigned parking, and ample guest parking. This is Florida lakefront living at its finest.

Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)

Listing Agent: Chip Fortenberry, Iii (863-673-9368)

Remarks: Easy Florida living starts here in Winter Haven Harbour, a centrally located 55+ condominium community close to shopping, dining, medical facilities, public transportation, and downtown Winter Haven. This 2-bedroom, 1.5-bath end-unit condo offers 840 square feet of functional living space and a smart opportunity for a buyer looking to downsize, simplify, or create a comfortable seasonal Florida retreat. The end-unit placement provides added privacy, while the half bath gives the floor plan extra everyday convenience compared to many smaller or single-bath options. Enjoy the low-maintenance lifestyle Winter Haven Harbour is known for, with community amenities that include a heated pool, clubhouse, shuffleboard, grilling area, fitness/community space, car wash area, elevator access, assigned/covered parking, and storage/laundry conveniences. Whether you are a full-time resident or a snowbird looking for a manageable Florida home base, this condo puts convenience, community, and value in one package. Buyer approval required. Buyer and buyer’s agent to verify association rules, fees, leasing restrictions, measurements, and all community information. **Some photos are AI enhanced**

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

Listing Agent: Don Jerue (863-259-9550)

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: AROD PARTNERS REALTY (407-627-7621)

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

Remarks: Enjoy a relaxed, maintenance-free lifestyle in this well-loved 55+ condo overlooking the beautifully maintained grounds of Imperial Harbours and the shores of Lake Howard. From both the bedroom and enclosed Florida room, take in peaceful views of the community pool and landscaped courtyard—an ideal backdrop for quiet mornings or unwinding at the end of the day. Located in Building Two, this second-floor unit offers convenient access via elevator or stairs and provides a comfortable, easygoing layout designed for everyday living. The bright and open great room flows seamlessly into the dining area, creating a welcoming space for both relaxing and entertaining. The primary suite is spacious and features a walk-in closet along with a private en suite bath complete with a step-in shower. The guest bedroom offers flexibility for visitors or additional use, while the kitchen provides ample cabinetry, stainless steel appliances, stone countertops with workspace for everyday needs. Interior features include tile flooring throughout and the convenience of an in-unit stackable washer and dryer. Condo is being sold fully furnished. Residents enjoy a variety of amenities, including a lakeside fishing pier, community pool, fitness area, meeting room, assigned covered parking, and extra storage. The condo fee simplifies daily living by covering cable, internet, water, sewer, trash, exterior maintenance, and grounds care. Ideally situated just minutes from shopping, dining, and the charm of downtown Winter Haven, this property offers an easy, enjoyable Florida lifestyle with lake access right at your doorstep.

Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)

Listing Agent: Deborah Grogan (863-812-5944)

Remarks: Rare opportunity in the desirable Lamplighter Condominium community on Lake Roy! This well-maintained 1-bedroom, 1-bath downstairs unit offers affordable ownership with a low HOA fee. Recent updates include energy-efficient windows and a gas hot water heater, both only 2 years old. Lamplighter is a waterfront community conveniently located in the heart of Winter Haven tucked behind the Lamplighter Plaza, with easy access to shopping, dining, medical facilities, and the Chain of Lakes. Ideal for owner-occupants, seasonal residents, or investors seeking a low-maintenance property in a prime location.

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

Listing Agent: Katherine Montana - De Jesus (863-508-3000)

Remarks: Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend of comfort and convenience in this beautiful Winter Haven property. Nestled in a peaceful neighborhood, this property offers spacious living areas and a welcoming atmosphere. Enjoy bright living, a well-appointed kitchen, and generously sized bedrooms. Don't miss out- schedule a showing today!

Listing is courtesy of: RIVERA & ASSOCIATES REALTY (813-443-5031)

Listing Agent: Maria Rivera (813-842-7399)

Remarks: 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: Under contract-accepting backup offers. Virtually Staged. Welcome to easy Florida living in the sought-after Orchid Springs 55+ community! This beautifully maintained 2-bedroom, 2-bath condominium is located in the desirable San Miguel Building and offers a peaceful second-floor setting with lovely views of the lush, landscaped grounds below. Step inside to find a spacious and comfortable floor plan designed for both everyday living and entertaining. The bright Florida room provides the perfect spot to enjoy your morning coffee, read a book, or simply relax while taking in the serene garden views. The primary suite offers a private retreat featuring an oversized walk-in closet and an updated bathroom with modern finishes, creating a comfortable and inviting space to start and end each day. One of the biggest advantages of this home is the exceptional value offered through the monthly HOA fee, which includes gas, water, sewer, trash, community pool, clubhouse, amenities, exterior maintenance, and grounds maintenance—allowing you to spend more time enjoying life and less time worrying about upkeep. Ideally located at 400 El Camino Drive, Unit 202, you’ll enjoy convenient access to shopping, dining, medical facilities, downtown Winter Haven, and the area’s many lakes and recreational opportunities. Whether you’re looking for a year-round residence, a winter getaway, or a low-maintenance lifestyle, this inviting condo offers the perfect combination of comfort, convenience, and affordability in one of Winter Haven’s most established 55+ communities. Come discover why so many residents love calling Orchid Springs home!

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Jessica Willaford (863-662-8549)

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 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)

Remarks: Under contract-accepting backup offers. Spacious 2-bedroom, 2-bath upper corner condo in the Barcelona Building of Orchid Springs, an all-ages community. This desirable end unit offers natural light and views from three sides, plus added privacy with minimal foot traffic. Recent updates include luxury vinyl plank flooring throughout, smooth ceilings, and neutral zero-VOC paint. Routine annual A/C maintenance completed in May 2026. The updated kitchen features 17 cabinets, 10 drawers, and a pantry, while the spacious primary suite offers a walk-in closet and en-suite bath. Assigned parking is located just below the unit. The monthly HOA fee of $312.69 covers exterior maintenance, grounds care, water, sewer, trash, gas service, pest control, common laundry facilities, and capital reserves. Conveniently located near LEGOLAND Florida and between Orlando and Tampa, with easy access to Winter Haven's renowned Chain of Lakes.

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

Listing Agent: Melissa Witter (863-206-8744)

Remarks: Under contract-accepting backup offers. PRICE REDUCED on this wonderful opportunity! Welcome to Winter Ridge Condominiums — Lakeside Living on the Winter Haven Chain of Lakes. Discover the charm of Winter Ridge, a desirable waterfront condominium community offering direct access to Lake Smart, part of the renowned Winter Haven Chain of Lakes. This inviting 2-bedroom, 2-bath home features an open floor plan with ceramic tile throughout, a galley-style kitchen equipped with a refrigerator, range, microwave, and dishwasher, plus a walk-in pantry/utility room with in-unit laundry hookups. Relax and unwind on the oversized screened lanai while taking in peaceful views of Lake Conine, perfect for morning coffee or evening unwinding. The home also includes two assigned parking spaces directly in front of the unit, with additional guest parking conveniently located near the clubhouse. Community amenities include a heated swimming pool, clubhouse, shuffleboard courts, and a fishing and boat dock—perfect for enjoying the waterfront lifestyle. The HOA takes care of exterior maintenance, roof upkeep, lawn care, common area landscaping, road maintenance, and pool and dock care, offering truly low-maintenance living. Outdoor enthusiasts will appreciate the public boat ramp across the street providing access to Lake Conine, and the nearby Lake Conine Nature Park (just 0.5 miles away), featuring walking trails, picnic areas, and scenic lake views. Centrally located near shopping, dining, and medical facilities, this property is also just minutes from Legoland and Highway 27, with easy access to Tampa and Orlando. Enjoy comfort, convenience, and lakeside living in one of Winter Haven’s most sought-after condo communities—Winter Ridge.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Michelle Heath (863-528-3123)

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: Welcome to easy Florida living at this beautifully updated 2-bedroom, 2.5-bath townhome with a rare 2 CAR GARAGE in the desirable Casa Del Sol community of Winter Haven. Offering direct views of the community pool and multiple outdoor living spaces, this home combines comfort, convenience, and a low-maintenance lifestyle in one attractive package. As you enter, you'll find a versatile flex space that can easily serve as a dining room, home office, reading nook, or additional sitting area. This inviting space features access to a private front patio, creating the perfect setting to enjoy your morning coffee. The updated galley-style kitchen showcases modern white cabinetry, granite countertops, stainless steel appliances, and ample storage, providing both style and functionality. The spacious living room features attractive laminate flooring and sliding glass doors that lead to the screened rear patio, creating a seamless indoor-outdoor flow ideal for entertaining or everyday living. A convenient half bath and a full laundry room add functionality and convenience to the first floor. Upstairs, both bedrooms provide privacy and comfort. The spacious primary suite serves as a relaxing retreat, complete with a large walk-in closet, a private bathroom with a tub, and access to a PRIVATE BALCONY overlooking the sparkling community pool. Enjoy peaceful mornings or unwind in the evenings while taking in the tranquil pool views from your own bedroom. The second bedroom offers flexibility for guests, family members, or additional workspace. The screened rear patio provides another wonderful outdoor living area and is perfectly positioned just steps from the community pool. Whether you're entertaining guests or simply enjoying Florida's beautiful weather, this space offers the ideal place to relax. Additional peace of mind comes from the 2020 air conditioning system. Residents enjoy access to community amenities including a swimming pool, shuffleboard courts, exterior maintenance services, sewer, trash service, and beautifully maintained grounds. Conveniently located in the heart of Winter Haven, this home is just minutes from downtown Winter Haven, the Chain of Lakes, shopping, dining, medical facilities, and LEGOLAND Florida Resort. Whether you're looking for a primary residence, seasonal getaway, or investment opportunity, this move-in-ready townhome offers an exceptional combination of location, lifestyle, and value.

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

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

Remarks: Under contract-accepting backup offers. Virtually Staged. Waterfront view from your porch. Affordability, low-maintenance comfort, & strong rental income potential. Waterfront view from your porch. Discover serene living at this charming 2-bedroom, 2-bathroom condo offering stunning sunset water views from its screened lanai. The home has a functional layout, it includes a combination of living & dining area, a large master suite with a walk-in closet, & a sliding glass door towards your comfortable back porch overlooking the canal water view; the kitchen has sufficient space; & there is a large storage room. Enjoy your Florida lifestyle, this welcoming community with built-in amenities, has direct lakefront access via a community dock for boating, fishing, and water sports on the connected Chain of Lakes. For only $253 a month, HOA covers your home's exterior maintenance. Location is accessible to nearby shopping, hospitals, medical offices, schools, and about an hour drive Tampa or Orlando. To schedule a showing, provide your realtor your pre-approval letter or proof of cash funds. At this price range, this move-in ready condo is your best choice.

Listing is courtesy of: MAZELG REALTY (863-399-0226)

Listing Agent: Lienyvette Grimaldo (863-399-0226)

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: Under contract-accepting backup offers. Welcome to this beautifully updated 3-bedroom, 2-bath condominium in the desirable Winter Ridge community of Winter Haven. Offering the perfect blend of comfort, style, and convenience, this move-in-ready home features a renovated kitchen with stunning granite countertops, updated cabinetry, and modern hardware. The spacious living areas and 2 bedrooms feature comfortable carpeting, while the kitchen and bathrooms are finished with durable tile flooring. The third bedroom has beautiful wood flooring. Both bathrooms have been tastefully remodeled with custom tile showers, granite countertops, and updated fixtures. Additional upgrades include updated lighting fixtures and ceiling fans throughout the home, providing a fresh, modern feel. Relax and enjoy Florida living from the screened lanai, that has an A/C unit. Residents of Winter Ridge enjoy access to a community pool and clubhouse, along with the convenience of an assigned covered parking space. Conveniently located this low-maintenance condominium offers an exceptional opportunity to enjoy the Florida lifestyle in a well-established community. Schedule your private showing today!

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

Listing Agent: Melissa Wren (863-557-0118)

Remarks: Under contract-accepting backup offers. 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: Florida Living at Its Best! Welcome home to this beautifully updated 2-bedroom, 2-bath residence offering the perfect combination of comfort, style, and convenience. From the moment you walk through the door, you'll be impressed by the bright, open floor plan, modern finishes, wood-look flooring, and inviting living spaces designed for everyday living and entertaining. The spacious primary suite serves as a private retreat and features sliding glass doors leading to a screened and covered lanai. A portion of the lanai has been enclosed to create a flexible bonus room—ideal for a home office, reading nook, fitness area, or hobby room. Step outside to your private tiled patio, the perfect place to enjoy your morning coffee, unwind after a long day, or host family and friends. This sought-after community offers amenities rarely found at this price point, including assigned covered parking, a sparkling community pool, and direct access to beautiful Lake Smart with a private boat ramp. Whether you enjoy boating, fishing, kayaking, or simply watching the sunset over the water, you'll love the lifestyle this community provides. Located just minutes from shopping, restaurants, medical facilities, and major roadways, this move-in-ready home offers the convenience buyers are looking for and the Florida lifestyle they dream about. Opportunities like this don't come along often. Schedule your private tour today and discover why this could be the perfect place to call home.

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

Listing Agent: Diana Acosta (914-562-3386)