Winter Haven Condos For Sale - 65 condos

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

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

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

Remarks: 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: 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: The property you are inquiring about is located in Winter Haven, FL, in the Orchid Springs area of Polk County. This is a second-floor unit with 2 bedrooms, 2 bathrooms, and is ready to move into. This is a 55+ community and has a nice square footage for this lifestyle. Many amenities are included in the HOA fee structure - lawn, water, sewer, natural gas, grounds, clubroom. The dishwasher is in as-is condition. This is a secluded area with no noise behind you (maybe a squirrel), but more peace and tranquility. Text, call, email, and see it today! Agents, please see MLS (Realtor) remarks.

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

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

Remarks: One or more photo(s) has been virtually staged. Downtown Winter Haven condo located in one of Winter Haven’s most iconic hotels, The Haven. This residence has been transformed into boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. With its blend of vintage charm, modern updates, and low-maintenance living, this 1-bedroom, 1-bath unit is ideal for first-time buyers, investors, seasonal residents, or anyone seeking an affordable condo with great rental potential. Located on the 3rd floor, the residence features tall ceilings, large windows, and bright natural light with elevated views of downtown. The updated kitchen offers granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets—perfect for maximizing storage in a condo setting. The spacious primary bedroom boasts oversized historic windows, a walk-in closet, and room for a king-sized bed. The bathroom has been refreshed with granite counters, a tiled tub surround, and a traditional tub/shower combo. The Haven provides sought-after condo amenities, including secure key-fob access, elevators, a community pool, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby. Residents also enjoy a private pool courtyard surrounded by lush landscaping, creeping fig walls, palm trees, and peaceful lounging areas—ideal for relaxation or working remotely outdoors. This walkable location offers the best of downtown Winter Haven living. Enjoy immediate access to dining, shopping, entertainment, and lakefront walking paths. With 50 lakes—including the world-famous Winter Haven Chain of Lakes—you’re minutes from boating, fishing, skiing, and sunset views. Everyday conveniences like Publix, Walmart, Aldi, TJ Maxx, medical facilities, and LEGOLAND Florida Resort are all close by. If you’re looking for an affordable, updated, low-maintenance condo with historic character and the convenience of downtown living, this stylish unit at The Haven checks every box.

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

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

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. One or more photo(s) has been virtually staged. Enjoy peaceful lakefront living in this beautifully updated 2-bedroom, 2-bath condo in the gated Winterset community. With an open floor plan, granite countertops, stainless-steel appliances, upgraded cabinets, and a cozy breakfast nook, this home blends style and comfort. The enclosed balcony offers stunning Garden Lake views, perfect for relaxing mornings or golden evenings. Recent updates include new plumbing, electrical, lighting, bathroom vanities, and updated flooring throughout. Winterset features resort-style amenities—pool, spa, clubhouse, tennis and pickleball courts, plus a private pier for fishing or kayaking. Located just 5 minutes from LEGOLAND and under an hour to Disney, this move-in-ready home delivers Florida living at its best. Sale subject to lender approval. SHORT SALE APPROVED at $170,000 (Appraised Value). Great opportunity for investors, first-time buyers, or a winter retreat.

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

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

Remarks: One or more photo(s) has been virtually staged. Waterfront Serenity Meets Effortless Living in the Heart of Winter Haven. Step into a lifestyle where your biggest daily decision is whether to enjoy coffee overlooking the lagoon or take a refreshing dip in the heated community pool. Nestled on the second floor of the meticulously maintained 55+ Granada Building, Unit 202 is more than just a home; it’s your private sanctuary in the sought-after Orchid Springs community. A Layout Designed for Connection and calm. Experience an open-concept living and dining area bathed in Florida’s natural light. The expansive Florida Roomacts as your front-row seat to nature, offering tranquil water views and lush landscapes that make every sunset feel like a private event. The Primary Retreat: A generously sized suite featuring a massive walk-in closet for ultimate organization. Modern Flexibility: Enjoy the convenience of an elevator and on-site laundry, with the rare added potential to install your own in-unit washer/dryer hookup. Seamless Comfort: A brand-new AC system ensures year-round peace of mind. The Gold Standard of HOA Value. Rarely does an HOA work this hard for you. This "all-inclusive" lifestyle eliminates the stress of multiple bills, saving you hundreds monthly. High-Tech Package: Includes Premium Cable and High-Speed Internet (a $250/month value). Total Utility Coverage: Gas, water, sewer, and trash removal are all covered. Maintenance-Free: Pest control, exterior upkeep, and grounds care are included, so you can spend your weekends at the private park or the clubhouse instead of mowing the lawn. The Best of Winter Haven at Your Doorstep. Beyond the gates of Orchid Springs, you are minutes from the vibrant energy of downtown Winter Haven. Indulge in local favorites like Nutwood or LoveBird, explore the world-famous Chain of Lakes, or enjoy the convenience of being just a stone's throw from LEGOLAND® Florida. Claim Your Piece of Paradise. With a recently adjusted price of $64,900, this move-in-ready residence offers a rare combination of waterfront beauty and unbeatable financial value. Schedule your private tour today and discover why life is better at Orchid Springs.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Carlos Diez Cordova (813-694-6208)

Remarks: Where Every Day Feels Like Vacation—Lakefront Condo! Desirable Upstairs condominium with unobstructed Lake Views. Welcome to your dream home! This stunning upstairs unit offers 2 Bedroom, 2 full bathrooms and a convenient 1-car garage! Enjoy breathtaking views of Winterset Lake from your home. The open floor plan is enhanced by skylights, providing ample natural light throughout. This home is perfect for both relaxation and entertaining. The spacious primary bedroom with ensuite bath. Wake to a beautiful view of Winterset Lake. 2nd bedroom is a great guest space or office. Enjoy your screened in Lanai with spectacular sunsets! Located in a resort-style community, you will have access to top-notch amenities including a Clubhouse, pool, spa, tennis courts, boat dock and fishing pier and direct lake access. Safety and peace of mind are ensured with a state-of-the-art security system controlling access to the community. Winterset is professionally managed and maintained. Experience the perfect blend of comfort and community in a highly desirable setting. A forever home or just a place to come to get out of the cold weather you will enjoy the tranquility and all the nature that Central Florida provides. Don't miss this opportunity. All measurements are approximate.

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

Listing Agent: Laurie Nock (937-218-0031)

Remarks: WELCOME HOME TO THIS MOVE IN READY LAKEFRONT CONDO. 2BEDROOM - 2 BATH WITH 1252 SQ FT OF LIVING AREA , PLUS A FLORIDA ROOM OVERLOOKING LAKE BUCKEYE. THIS CONDO UNIT HAS STORAGE THROUGHOUT, GREAT STORAGE CLOSET OFF THE FLORIDA ROOM, ALSO INSIDE UTILITY WITH WASHER/DRYER HOOKUPS AND THE PRIMARY BEDROOM HAS A WALK IN CLOSET. YOU HAVE THE PRIVACY OF THIS UPSTAIRS UNIT WITH A BEAUTIFUL VIEW, NEW CARPET & INTERIOR PAINT,. IT ALSO FEATURES CONVENIENT COVERED PARKING AND COMMUNITY POOL & TENNIS. LOCATED NEAR POLK STATE COLLEGE , YOU CAN ENJOY A WALK AROUND NEARBY LAKE ELBERT OR DRIVE JUST MINUTES TO DOWNTOWN WINTER HAVEN FOR SHOPPING, RESTAURANTS AND COMMUNITY EVENTS. DON'T MISS OUT ON THIS LAKEFRONT VIEW OF LAKE BUCKEYE .

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

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

Remarks: Welcome to maintenance-free living nestled in the thriving community of Cypresswood Golf and Country Club that offers an unparalleled lifestyle and peace of mind with a 24-hour guard at the gated entrance, perfect for year-round living or a worry-free seasonal getaway. This second-floor condo boasts a world of comfort and convenience with the A/C having been replaced entirely in 2024, giving you one less worry, tons of storage in generously-sized walk-in closets that both bedrooms offer as well as additional linen storage in the hallway and primary bedroom that will keep your space organized and clutter-free effortlessly. Dive into relaxation and fun at the community pool or host gatherings, socialize with neighbors, or simply unwind in the inviting communal spaces of the clubhouse. The on-site restaurant offers convenient and flavorful dining options, perfect after a tennis or pickleball match on the community's courts or day of golf on Cypresswood's 18-hole championship course. The low monthly HOA fee includes all exterior maintenance, landscaping, pest control, trash collection, and the pool and tennis amenities. Residents also enjoy a discount on daily golf and annual memberships! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options. Schedule your private showing today, and make this lovely condominium yours.

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: Under contract-accepting backup offers. Welcome to this serene 52-unit condominium community, beautifully nestled within a lush, wooded setting. Enjoy peaceful surroundings complete with a tranquil lagoon teeming with birds, otters, and natural wildlife, along with a sparkling community pool that invites relaxation. This well-maintained 2-bedroom, 2-bath residence offers a desirable split-bedroom floor plan and an open-concept living and dining area—perfect for both everyday living and entertaining. A light-filled sunroom provides the ideal space to unwind while taking in calming lagoon views. The kitchen is thoughtfully designed with ample cabinetry and storage, making meal prep both functional and enjoyable. The building features the convenience of an elevator for easy access, along with laundry facilities located on each floor. This unit also includes an assigned carport just steps from the elevator for added ease and comfort. If you’ve been considering low-maintenance living in a peaceful, nature-filled setting—this is condo living at its best!

Listing is courtesy of: LEGACY REAL ESTATE CENTER INC (863-676-0200)

Listing Agent: Dolores Vogel (863-632-5573)

Remarks: One or more photo(s) has been virtually staged. Waterfront condo on the Winter Haven Chain of Lakes! Spend every day surrounded by breathtaking sunrises and sunsets in this beautifully maintained ground-floor condo located within the highly desirable, gated waterfront community of Winterset on Lake Winterset. Perfectly positioned along the shores of the Winter Haven Chain of Lakes, this residence offers a rare opportunity to enjoy true Florida lakefront living at an attainable price. This 2-bedroom, 2-bath condo includes a private one-car garage and is ideal for retirees, seasonal residents, first-time buyers, or anyone seeking a low-maintenance waterfront lifestyle. The bright, open floor plan features newer LVP flooring, neutral finishes, and abundant natural light throughout. Sliding glass doors frame peaceful water views and open to a screened patio—an inviting spot to enjoy morning sunrises over the lake or unwind as the sky glows at sunset. The kitchen is both functional and welcoming, offering a breakfast bar, dinette area, walk-in pantry, and all major appliances, including a gas range. The spacious primary suite enjoys tranquil lake views and includes a walk-in closet, ceiling fan, and en-suite bath with dual sinks, linen storage, and a walk-in shower. A comfortable guest bedroom and full bath provide privacy for visitors or flexible living space. Residents of Winterset enjoy a true resort-style lifestyle, with access to a lakeside clubhouse, heated pool and spa, tennis and pickleball courts, shuffleboard, and a private boat ramp offering access to more than 20 interconnected lakes—perfect for boating, fishing, skiing, and waterfront dining. The gated setting, manicured grounds, and walking paths enhance the peaceful, well-maintained atmosphere. Ideally located just minutes from Publix, Walmart, medical facilities, Legoland, dining, and downtown Winter Haven, with easy access to both Tampa and Orlando, this home offers the best of convenience and waterfront living. A rare opportunity to own a ground-level, lakefront condo with a private garage—where sunrise mornings and sunset evenings become part of everyday life.

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

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

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

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

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

Remarks: A delightful ground-floor 1-bedroom, 1-bath condo that embodies comfortable, low-maintenance Florida living. Step inside to a well-sized living room that invites relaxed gatherings and everyday comfort. The kitchen features a gas stove, ideal for home-cooked meals, and both the A/C and water heater are newer, giving you added peace of mind. This home’s HOA covers exterior maintenance, so you can enjoy more time living and less time on chores. As a resident, you’ll also love the community pool, perfect for refreshing dips on warm Florida afternoons. And to make this condo truly move-in ready, the seller is offering a flooring credit — a great opportunity to personalize the space to your taste. Location highlights: Winter Haven is known for its welcoming community and vibrant lifestyle. Enjoy scenic outdoor living with access to the Chain of Lakes lifestyle, where boating, paddleboarding, fishing, and unforgettable sunsets are part of everyday life. The nearby Chain of Lakes Trail offers miles of paved paths perfect for walking, biking, or jogging. Legoland is just up the road!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Andrew Fearn (863-812-1755)

Remarks: Welcome to easy, low-maintenance Florida living in this fully furnished 1 bedroom, 1 bathroom ground-floor condo located in the well-established Winter Haven Harbour community! Ideally positioned with direct views of the pool and shuffleboard courts, this unit offers both convenience and a relaxed lifestyle. Step inside to find a move-in ready space complete with living room furniture, bedroom furnishings, dining set, and a fully equipped kitchen. Many furnishings are brand new and have never been used. This is perfect for seasonal living, downsizing, or a full-time residence. The ground-floor location provides easy access with close proximity to elevators, laundry facilities, mailboxes, and the community bulletin board. Enjoy everything this quiet and well-maintained community has, including a resort-style pool, shuffleboard courts, clubhouse, fitness area, and multiple outdoor seating and gathering spaces. Each unit includes assigned covered parking and a dedicated storage area, along with additional guest parking available. The monthly association fee covers water, sewer, trash, grounds maintenance, and upkeep of all community amenities—making for truly stress-free living. Whether you’re a snowbird, retiree, or simply looking to simplify your lifestyle, this condo offers the perfect opportunity to enjoy Florida living at its best. Move right in as-is or you have the opportunity to update to your personal taste!

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

Listing Agent: Aubrie Flint (863-618-6347)

Remarks: This beautifully maintained **DELUXE UNIT** is move-in ready and offers everything you’ve been searching for—located in a desirable **55+ community**, perfect for comfortable and peaceful living! What sets this unit apart is its **private in-unit laundry room**, a rare and valuable upgrade compared to other units in the community—adding both convenience and functionality. Enjoy improved energy efficiency with newly installed solar window tint on all windows, along with recently added vertical blinds. The plumbing has been upgraded, providing added peace of mind. Inside, you’ll find a stunning built-in bookcase and shelving system, perfect for organization and style. Relax and take in the views from both the screened front and back porches—ideal for morning coffee or evening unwinding. All appliances are included for your convenience: washer, dryer, refrigerator, dishwasher, stove/range, and microwave. The bathroom has been tastefully updated with a new toilet and vanity. Additional features include one assigned covered parking space under the carport and a private 4x8 storage unit located on the same floor. The condo association fee covers water and garbage, adding even more value to this exceptional home.

Listing is courtesy of: CENTRIC REALTY SERVICES LLC (407-421-9391)

Listing Agent: Jean Julme (321-280-0658)

Remarks: 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: Beautiful condo located in the Garden Villas section of the Winterset community. This property is perfect for the person looking for a maintenance free lifestyle and resort style of living. Winterset offers a full time secured gated entryway, community pool, clubhouse, tennis courts, and more. The community overlooks beautiful Lake Winterset. You will enjoy not having to worry about lawn maintenance or other outside care in the Garden Villas condos. This property features a nice sized master bedroom on the first floor, and a spiral staircase leading to the second bedroom/loft area on the second floor. There is a large balcony located off of the living room, perfect for sipping coffee in the morning and relaxing in the afternoon. All appliances are included. The Winterset community is located off of Cypress Gardens Blvd, so you're minutes away from restaurants, entertainment, and shopping. Come see everything this condo has to offer!

Listing is courtesy of: THE SOMERDAY GROUP PL (813-520-9123)

Listing Agent: Alexander Matos (813-842-4292)