Winter Haven Condos For Sale - 63 condos

Remarks: Nestled on beautiful Lake Hartridge, is this completely remodeled and move-in ready, stunning 2-bedroom, 2.5-bath condo in Casa Del Sol Village. This unit offers modern updates and a comfortable layout in the heart of Winter Haven. Every inch has been refreshed — featuring luxury vinyl flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living area and guest half bath downstairs make entertaining easy, while both upstairs bedrooms feature private ensuite baths for added convenience. Enjoy low-maintenance living with a 2-car attached garage, access to the community pools, and a location that’s close to shopping, dining, and the Chain of Lakes. Perfect as a primary home, seasonal retreat, or investment property — this move-in-ready condo combines style, comfort, and convenience in one incredible package.

Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)

Listing Agent: Nikki James (863-581-3499)

Remarks: Under contract-accepting backup offers. Located in desirable southeast Winter Haven, this second-floor, east-facing one bedroom, one bath condo, with NO age restrictions, offers a functional layout with great potential for customization. The unit features a combined kitchen, dining, and living/office space that opens to a rear enclosed patio/sunroom with sliding glass doors- perfect for enjoying morning light. While the condo is need of updating, it presents an excellent opportunity for investors or buyers looking to personalize a space to their taste. Conveniently situated near local schools, shopping, and hospitals, and just minutes from LEGOLAND Florida Resort, the location also provides easy access to both Tampa International Airport and Orlando International Airport, along with the wide array of attractions located within each city. The seller is motivated.

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

Listing Agent: Dawn Van Meter (863-287-7013)

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: 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: 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: Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are newer dual pane windows, tile throughout the living area, and vinyl plank floors in the bedrooms! The air conditioner is only two years old and has a warranty that expires in 2033 and the washer/dryer is only one year old. The interior walls were just painted and this unit is ready for a new owner or tenant! This is one of the nicest units in the complex! Call today to schedule a showing!

Listing is courtesy of: CLARK REALTY LLC (863-345-2155)

Listing Agent: Steven Perkins (863-797-7276)

Remarks: Under contract-accepting backup offers. Short Sale. 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 & a peaceful feel while enjoying the security & 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 & 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: Under contract-accepting backup offers. UPDATED condo. NEW Bathroom Vanity & fresh Paint throughout. Price Improvement & Great opportunity to add your personal style to this 2 bedroom 2 full bath condo in Park Lake. Located on the 2nd floor close to the elevator with tremendous rental returns. Luxury Vinyl flooring in main living area & primary bedroom. Gas range & Water Heater. Ceiling fans throughout...Roof 2021...Washer/Dryer included with private laundry closet. NEW Dishwasher & Gas Stove just installed. NEW 5T 14 Seer AC just installed. Wet Bar...Terrific view from the back of the newly renovated baseball complex. Walking distance to restaurants & NEWLY RENOVATED BASEBALL COMPLEX. View of Lake Lulu with lake access for fishing off the dock. Primary bedroom offers a walk-in closet & natural light. This building offers an elevator & stairs as well as 1 dedicated parking space. Priced to sell & Perfect for Snowbird or Investor!

Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)

Listing Agent: Dora Siler (407-493-4959)

Remarks: Welcome home to this charming 1 bedroom condo. Enjoy a lifestyle that blends comfort and convience, with everything you need cloSse by-shopping, parks, dining and commuting routes. Inside, you'll find a bright and functional layout with a spacious living area and cozy bedroom. Whether you're a first time homebuyer, downsizing or investor. Schedule your showing today.

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

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

Remarks: 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: MUST SEE! Discover this beautifully remodeled first-floor condo with NO STAIRS to climb, offering the convenience and comfort of true single-level living. Perfect for year-round residents, seasonal owners, or anyone seeking easy accessibility, this move-in-ready home combines modern updates with an exceptional lifestyle in one of Winter Haven's most desirable lakefront communities. Located just steps from the community clubhouse, pool, fitness room, mailboxes, and parking, you'll enjoy maintenance-free living with outstanding amenities right outside your door. Park Lake residents also enjoy access to a private dock, gazebo, and beautiful waterfront views of Lake Lulu, part of the world-famous Winter Haven Chain of Lakes, providing opportunities for boating, fishing, and enjoying Florida's natural beauty. The nearby Chain of Lakes Complex and baseball fields add to the recreational appeal. Inside, soaring vaulted ceilings in the living room, dining area, and primary bedroom create a bright and spacious atmosphere. The screened lanai offers dual entry points and the perfect place to enjoy your morning coffee or evening breeze. Major renovations completed in December 2022 include stylish kitchen cabinetry, granite countertops, under-counter refrigerator, induction cooktop, and ceramic tile flooring throughout. Additional upgrades include impact-resistant windows, a new A/C system with UV light, Nest security system, and a new washer and dryer. The location is hard to beat, with restaurants, shopping, banking, medical facilities, downtown Winter Haven, and LEGOLAND Florida all just minutes away, making this home ideal for both full-time living and seasonal enjoyment. Whether you're looking for a primary residence, winter retreat, or investment opportunity, this beautifully updated condo offers affordability, convenience, lakefront amenities, and a truly carefree Florida lifestyle. Seller financing and Private Financing Available! Do not wait, it will not last long!

Listing is courtesy of: HUT REALTY, LLC (407-559-2929)

Listing Agent: Daniel Hut (863-400-6090)

Remarks: Under contract-accepting backup offers. Improved Price!! All new window in the building...Price improvement...Seller ready to sell! Beautifully maintained 55+ condominium located in Lake Ridge Winter Haven. This is a gated community offering a tranquil living space. Conveniently located near hospitals, restaurants, shopping, entertainment and so much more. This home offers everything you need to live a true Floridian lifestyle. Amenities include heated pool ALL year around, tennis court, shuffleboard, pickle ball, car washing area, outdoor grills, community room, and covered guest parking for your family to enjoy when they visit. The community offers community events so boredom is not an option. So much opportunity to socialize and create amazing memories. This specific unit offers a relaxing airy and bright Florida room to sit back and enjoy your coffee. Association will be putting in new windows and fresh exterior paint this summer. The assessment is PAID in FULL so you can affordable live in style. Monthly association covers water, sewer, trash, fiber optics cable, internet, prime HD package, condo reserves, and maintenance. This is truly a hidden gem waiting for its new owner! Whether you are looking for a winter retreat or a forever home, this condominium offers you your own piece of paradise. Check it out before its gone! Schedule your showing TODAY!

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

Listing Agent: Brenda Brooks (863-370-9667)

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.

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

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

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: Condo located in Winter Haven FL, the Water Ski Capital of the World and only 6 minutes from Legoland! Ground-floor, furnished condo in Sandy Cove, a lakefront community on the beautiful Winter Haven Chain of Lakes. This furnished 2-bedroom, 1-bath unit offers low-maintenance living that’s ideal for full-time residents, seasonal owners, retirees, or anyone seeking a convenient Florida lifestyle. The layout offers comfortable living with a spacious great room featuring laminate flooring, a ceiling fan, and sliding doors leading to the enclosed Florida room. The adjacent dining space is cozy and ideal for entertaining or quiet nights in. The kitchen is complete with quartz countertops, included appliances, and a stackable washer and dryer. The unit also features double-pane windows for improved energy efficiency, comfort, and noise reduction. The primary bedroom is generously sized and features a ceiling fan, walk-in closet, and direct access to the bathroom. The guest bedroom is also comfortably sized with a built-in closet, ceiling fan, and en-suite-style bathroom access. The bathroom has been updated with an upgraded vanity, solid-surface countertop, and walk-in shower. Enjoy outdoor living from the enclosed Florida room with screens and vinyl windows, perfect for relaxing or entertaining year-round. This ground-floor unit is ideally positioned just steps from the community clubhouse, grill area, and heated pool maintained at approximately 85 degrees for year-round enjoyment. Sandy Cove also offers a community dock on Lake Lulu, one of twenty+ lakes on the Winter Haven Chain, providing a peaceful setting to unwind, enjoy waterfront views, and take in beautiful Florida sunsets. Residents enjoy the relaxed lifestyle that makes Winter Haven so desirable, including boating, fishing, lakeside dining, golf courses, walking paths, and year-round community events. Conveniently located near everyday essentials and recreation, the condo is just minutes from Publix Super Markets, CVS Pharmacy, restaurants, banks, medical offices, and Walmart shopping. Nearby public boat access on Lake Summit makes it easy to enjoy the Chain of Lakes lifestyle, while several local golf courses are only a short drive away. The location also provides convenient access to both Orlando and ,making this an excellent choice for easy, low-maintenance Central Florida living.

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

Listing Agent: Michael Stone (863-412-9733)

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, neutral zero-VOC paint, and 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: One or more photo(s) has been 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: 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. 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: Welcome to 207 Winter Ridge Blvd – A Serene Lakeside Retreat! This charming end-unit condo is a peaceful lakeview haven. Features; 2 spacious bedrooms, 2 bathrooms, and an open-concept living and dining area that flows effortlessly into an enclosed Florida room—ideal for soaking in breathtaking sunsets over Lake Conine. The kitchen features a built-in desk and a convenient closet pantry, while the master suite boasts a generous walk-in closet. Additional highlights include: Two dedicated parking spaces (one covered), brick paved front patio for outdoor enjoyment, high-end windows and doors, Hurricane shutters for peace of mind, new roof installed in 2024. Located within city limits, this quiet and well-maintained community offers resort-style amenities including a clubhouse, sparkling pool, shuffleboard courts, and access to a community dock and boat slip on Lake Smart. Whether you're fishing off the pier or strolling to nearby shops and restaurants in downtown Winter Haven, you'll love the blend of convenience & charm.

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

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