Winter Haven Condos For Sale - 68 condos

Remarks: Spacious condo with 1 bedroom, laundry inside, bonus patio area and on 1st level. Easy to maintain so you have the flexibility to travel and relax. The kitchen is white and bright and living room/dining combo offers an open floor plan. This home feels comfortable and cozy. This condo comes with an assigned parking spot. Close to restaurants, shopping lakes and a variety of activities. Newer A/C installed in 2022. Note: stove, microwave & dishwasher convey. **HOA is $208.62 + $29.47 = $238.09 until December 31, 2026 due to gas line repay reserve assessment 6/1 - 12/31.**

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Tina Mcdonald (989-385-5757)

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: 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: Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condominium offering effortless Florida living in a highly desirable Winter Haven location. Situated within a well-maintained community featuring a community pool and extensive HOA-covered amenities, this residence is ideal for full-time homeowners, seasonal residents, downsizers, or investors seeking comfort, convenience, and low-maintenance living. Step inside to discover a bright and inviting open-concept living and dining area enhanced by durable tile flooring and abundant natural light. A standout feature of this home is the presence of two separate sliding glass doors within the main living and dining space—one opening to a private outdoor balcony and the other leading to a spacious screened and enclosed patio, creating a seamless connection between indoor and outdoor living. This versatile enclosed space serves as a natural extension of the home and is ideal for a home office, hobby room, reading retreat, fitness area, or additional entertaining space. Large windows showcase tranquil views of the mature landscaping and beautiful blooming crepe myrtles, creating a peaceful atmosphere year-round. The thoughtfully designed galley kitchen features classic white cabinetry, a stylish subway tile backsplash, a dual-basin stainless steel sink, full-size appliances, and the added convenience of an INCLUDED WASHER AND DRYER. The primary suite serves as a relaxing retreat, complete with a walk-in closet and a private ensuite bath featuring a walk-in shower. A generously sized second bedroom and full guest bathroom provide comfortable accommodations for family and guests while offering flexibility for additional workspace if desired. This home has been thoughtfully maintained and updated, including an UPDATED HVAC SYSTEM approximately five years old. The building ROOF WAS REPLACED IN 2021 and is maintained by the HOA, while the owner-installed PATIO ROOF WAS UPDATED IN 2022, providing added value and peace of mind for the next owner. Residents enjoy a truly carefree lifestyle with HOA services that include exterior building maintenance, roof maintenance, trash service, driveway maintenance, routine pressure washing, professional landscaping, and community pool maintenance. These comprehensive services allow homeowners to spend less time on upkeep and more time enjoying the Florida sunshine and community amenities. Ideally LOCATED NEAR PICTURESQUE LAKE BUCKEYE, this home offers convenient access to fishing, boating, and scenic outdoor recreation while remaining close to shopping, dining, medical facilities, and everyday conveniences. The property is also just MINUTES FROM DOWNTOWN WINTER HAVEN, THE RENOWNED CHAIN OF LAKES, and LEGOLAND Florida Resort. Major roadways nearby provide easy access to Lakeland, Orlando, and Tampa, making commuting and travel exceptionally convenient. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this move-in-ready condo offers the perfect combination of comfort, convenience, and value in the heart of Winter Haven.

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. 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: 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: 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)

Remarks: Under contract-accepting backup offers. Offers should be submitted on the most recent/updated FAR-BAR As-Is contract & be accompanied by signed addenda (available via MLS attachment), as well as pre-qualification/approval letter or Proof of Funds. Customers are NEVER allowed on the property without their agent present. This includes showings, inspections, appraisals, etc. Lockbox and/or gate codes should NEVER be provided to customers. See attachments in MLS for information on the HOA/COA.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Oscar Allende Melendez (787-409-2175)

Remarks: Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The large primary bedroom has a walk-in closet leading to a sunroom, creating a versatile space for relaxation or hobbies. Newer oversized windows throughout the unit bathe the living area in natural light, further enhancing the spectacular lake views... Live an active lifestyle with sparkling swimming pool directly on the lake well-equipped fitness center, shuffleboard court, recreation room and library. Indoor and Outdoor storage comes with the unit. On-site laundry facilities are available for residents. This condo is perfect for full-time residents seeking a tranquil lakeside retreat or snowbirds desiring an affordable winter getaway. Those seeking a low-maintenance lifestyle with condo fees covering water, sewer, trash, cable, internet, and all exterior maintenance. Additional highlights include a single covered parking spot, a dock for fishing or viewing the water, boat slips available on a first-come, first-served basis. Enjoy planned social events and activities for residents. No pets or smoking allowed. Winter Haven's central location provides easy access to theme parks like Orlando and Tampa Downtown area Grocery stores, shopping, movie theaters, restaurants and medical facilities, making this a prime location. Don't miss this extraordinary opportunity to own a piece of paradise. Escape to the tranquility, luxury, and with expansive water views where every day feels like a vacation.

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: Victoria Bollea (813-230-4529)

Remarks: Welcome 55+ or investors! This well-maintained one-bedroom, one-bathroom condo with an additional bonus room is the perfect place to retire and take it easy, or a fantastic addition to your investment portfolio. Located in the heart of Winter Haven, this home is just a mile from Legoland, shopping, and dining. The community also features a sparkling pool for you to relax and enjoy year-round. Don't miss out on this prime opportunity!

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

Listing Agent: Angela Perkins (863-280-5396)

Remarks: Under contract-accepting backup offers. 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: 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: 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: 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: 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. 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. The A/C is newly installed (Dec 2025). 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: FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit, spacious 2 bedroom 2 bath townhome in a gated community. This unit is conveniently located right across the street from the clubhouse, pool, tennis courts and golf course!! Great for just starting out or ready to retire. Great Florida Room for relaxing when the weather is nice. Close to shopping and LegoLand!!

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

Listing Agent: Rhonda Chastain (863-698-9801)