If lake life is your priority, Winter Haven sets the bar. Known as The Chain of Lakes City, Winter Haven offers true boat-to-boat connectivity with dozens of lakes linked by navigable canals. From sunset cruises to weekend waterski shows, the lakes here aren’t just scenery — they’re part of daily life.

Lakefront homes range from historic properties near downtown to newer estates tucked along quieter canals. With public boat ramps, waterfront dining, and LEGOLAND just minutes away, Winter Haven delivers a rare mix of recreation, convenience, and authentic lakefront living.

👋 Let’s Chat About Lakefront Living
Can’t find exactly what you’re looking for? Don’t worry—new homes pop up every week, and the best ones go fast. Let’s connect and make sure you don’t miss the perfect place. Call me at 863-398-6243 or go to www.talkwithvince.com to set up a Zoom call.

 

$470,000
4 Beds 2 Baths Island Lakes SubDv. 33881 Zip Code
CHAIN OF LAKES LAKEFRONT LIVING on Lake Rochelle! Welcome to Island Lakes, where everyday life feels like a vacation. Located on the highly desirable Winter Haven Chain of Lakes, this beautifully updated home offers the ultimate waterfront lifestyle—boating, sunset cruising, and lakefront dining right from your own backyard. This 4-bedroom, 2-bath home is designed for both comfort and entertaining, featuring an open floorplan with stunning lake views from the main living areas. The spacious great room is filled with natural light, showcasing soaring ceilings, plant shelves, and an expansive sliding glass door that seamlessly blends indoor and outdoor living. The updated kitchen is both stylish and functional, complete with new cabinetry, solid surface countertops, stainless steel appliances, a full tile backsplash, breakfast bar, and a cozy eat-in nook—all perfectly positioned to take in the water views. The primary suite has been beautifully renovated, featuring a sliding barn door leading to a spa-like bathroom with a walk-in glass and tile shower, dual vanities with stone countertops, and a large walk-in closet with built-ins and hidden storage. Step outside and experience true Florida living with a huge screened outdoor living space complete with a hot tub, perfect for relaxing evenings or entertaining guests year-round. Beyond that, enjoy your private dock with a covered boat lift and freshwater supply, ready for days on the Chain. A public boat ramp is just minutes away. This home also features $92,000 in solar panels, providing exceptional energy efficiency and long-term savings—keeping utility costs low while supporting a more sustainable lifestyle. Additional features include a fully fenced backyard, beautiful lake views, and a prime location near Hwy 27 and I-4 with easy access to Orlando, Disney, Lakeland, and Tampa. This is more than a home—it’s a true Chain of Lakes lifestyle with comfort, efficiency, and unforgettable views.

4123 Island Lakes Drive, Winter Haven

$684,999
4 Beds 3 Baths Leisure Shores SubDv. 33881 Zip Code
Experience true Florida waterfront living on beautiful Lake Hartridge, one of the larger lakes on Winter Haven's famous Chain of 24 interconnected lakes. With miles of navigable waterways, you'll enjoy waterfront dining & various live music venues which have docks, as well as fishing, water skiing, kayaking, sailing, and endless exploration without ever leaving the chain. Beautifully renovated 4-bedroom, 3-bath lakefront home, offering approximately 90 feet of shoreline with a private dock, which offers the perfect blend of comfort, convenience, and breathtaking scenery. Begin each day with spectacular sunrise views from the spacious screened lanai overlooking the lake, where you'll regularly enjoy sightings of bald eagles, ospreys, herons, otters, and other native Florida wildlife. Entertain lakeside or spend the afternoon on the water. Lake Hartridge Park and the public boat ramp are conveniently located just down the street. Inside, soaring vaulted ceilings and an open, light-filled floor plan create an inviting atmosphere that complements the waterfront setting. The thoughtfully designed split-bedroom layout includes two Master Suites, each featuring a private bath, walk-in closets, and direct access to the screened lanai. There is also direct access to a bathroom from the patio; perfect after boating, swimming, fishing, gardening, or enjoying a day on the lake. Extensive renovations and recent improvements provide exceptional comfort, efficiency, and peace of mind, including: • Brand-new kitchen appliances • New 22-mil luxury vinyl plank flooring throughout • New RHEEM water heater • New lighting and ceiling fans throughout the home • Additional blown-in attic insulation for significantly improved energy efficiency • 2025 Goodman/Daikin 5-ton HVAC system with a transferable 5-year parts and labor warranty, which is transferable to you. • 2023 Generac 22-kW whole-house generator, recently professionally serviced, tested, and ready to provide uninterrupted power whenever needed • Durable 40-year metal roof with approximately 15+ years of expected service life remaining Additional features include public water, sewer, and natural gas service, a wood-burning fireplace with a natural gas starter for effortless fires, a spacious two-car garage with a recently installed automatic garage door opener, and a lake-fed irrigation system that keeps the lawn lush without costly municipal water. Whether you're looking for a year-round residence, a luxurious waterfront retreat, or a home designed for the boating lifestyle, opportunities like this on the Winter Haven Chain of Lakes are becoming increasingly difficult to find. This property combines modern updates, dependable major systems, and one of Central Florida's waterfront locations into a truly exceptional place to call home.

2004 Leisure Drive, Winter Haven

$525,000
4 Beds 4 Baths Hanna Sub SubDv. 33880 Zip Code
Welcome to the Chain Life! Situated on a spacious 0.47-acre lot with no HOA, this beautifully updated lakefront property on Lake Howard offers a rare opportunity to enjoy life on the renowned Winter Haven Chain of Lakes. One of the home's most desirable features is the beautifully remodeled studio-style guest suite with its own private entrance and en-suite bathroom. Complete with a wood-burning fireplace and ample space to add a kitchenette, this versatile space is ideal as a mother-in-law suite, private guest quarters, home office, or game room. This property would make a great short term rental for VRBO or Airbnb! The main residence features 3 bedrooms and 2.5 baths with numerous updates throughout. The renovated kitchen showcases new cabinetry, beautiful granite countertops, a stainless steel range and microwave, breakfast bar seating, and picturesque views of the backyard. Wood flooring flows through the spacious living areas, including formal living and dining rooms, an open kitchen, and a comfortable family room designed for both everyday living and entertaining. The primary suite offers a private en-suite bathroom with a walk-in shower and access to the beautifully remodeled guest bathroom that features a relaxing tub. Fresh interior paint and numerous recent improvements make the home truly move-in ready. Additional features include a well-equipped laundry room with cabinetry, utility sink, and a refrigerator, an oversized 24' x 26' two-car garage with built-in storage closets, rain gutters, a lake-fed irrigation system, a deep driveway with plenty of parking, and two A/C systems installed in 2021 and 2023. Step outside and enjoy the Florida lifestyle. Relax with your morning coffee on the covered front porch overlooking Lake Howard, or entertain family and friends on the expansive concrete patio overlooking the spacious backyard. Across the street, your private dock provides direct access to Lake Howard and the famous Winter Haven Chain of Lakes, connecting you to 20 navigable lakes. Spend your days boating to waterfront restaurants and bars, watching seasonal Legoland fireworks from the water, seeing seaplanes take off from Lake Jessie, or visiting the Moose Lodge for dining and social events, all which area accessible by boat. Conveniently located between Tampa and Orlando, Winter Haven offers easy access to major airports, Gulf and Atlantic beaches, and a vibrant downtown filled with locally owned restaurants, craft cocktail bars, a brewery, boutiques, and a popular weekly farmers market. Don't just live on the water—experience the unmatched lifestyle of the Winter Haven Chain of Lakes. Schedule your private showing today.

1475 S Lake Howard Drive, Winter Haven

$1,195,000
5 Beds 6 Baths Na SubDv. 33881 Zip Code
Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end street. Mature oak trees and lush tropical landscaping create a timeless Old Florida ambiance while blending seamlessly with the home’s fresh, modern updates. A long private driveway welcomes you to the property, leading to an oversized detached two-car garage complete with a private apartment above—ideal for guests, multigenerational living, rental income, or a secluded home office—and a convenient full bathroom below. Inside the main residence, an expansive and thoughtfully designed floor plan features four spacious bedrooms and 4.5 beautifully appointed bathrooms. One bedroom is currently styled as a cozy movie room, creating the perfect entertainment space for relaxing evenings or family gatherings. The luxurious first-floor primary suite serves as a true retreat, offering a spacious sitting area with stunning views overlooking the sparkling screened pool and tranquil lakefront setting. The spa-inspired primary bathroom showcases a soaking tub, oversized walk-in shower, elegant dual vanities, and generous space designed for comfort and relaxation. At the center of the home is the beautifully updated gourmet kitchen, featuring sleek quartz countertops, modern cabinetry, stainless steel appliances, and abundant prep and storage space sure to impress any chef. Elegant porcelain flooring flows throughout the main living areas, while plush carpeting adds warmth and comfort to the bedrooms. Recent upgrades, including a new roof and new AC system, provide peace of mind and enhance the home’s fresh, move-in-ready appeal. Designed to maximize the spectacular lake views, the expansive lanai and private screened-in pool area with an in-ground hot tub create the ultimate outdoor oasis for year-round Florida living. Newly refreshed pool and lanai screening further elevate the experience, seamlessly blending indoor and outdoor entertaining spaces. For boating enthusiasts, the property truly stands out with a private covered dock featuring a metal roof and boat lift, offering direct access to the renowned Winter Haven Chain of Lakes, known for boating, fishing, watersports, and unforgettable sunset cruises. Additional highlights include dedicated RV parking with electrical, water, and sewer hookups, making this property ideal for those seeking adventure without sacrificing luxury and convenience. Located in the heart of Winter Haven, known as the “Chain of Lakes City,” residents enjoy easy access to over 50 interconnected lakes, waterfront dining, boutique shopping, recreational trails, and convenient access to both Tampa and Orlando attractions. This extraordinary lakefront estate perfectly combines modern updates, timeless elegance, and resort-style living—offering a truly rare opportunity to own a one-of-a-kind waterfront retreat.

250 Brigham Road Nw, Winter Haven

$439,900
3 Beds 2 Baths Hartridge Hills SubDv. 33881 Zip Code
PRICE IMPROVEMENT! LAKEFRONT 3 BEDROOM / 2 BATH HOME ~ 2,847 SQ FT ~ WITH PICTURESQUE OPEN WATER VIEWS AND PRIVATE 30 FT DOCK! OWNER FINANCING AVAILABLE. Located directly on Lake Pansy in the gated subdivision of Hartridge Hills, a quaint lakefront community of approximately 60 homes. NEWER ROOF 2022 and NEWER GENERAC GENERATOR 2020. Lot size is 150 X 83 ft directly on Lake Pansy. Additional lot size in records of 2.44 acres includes riparian or water rights into the lake. Beautiful stone working fireplace with vaulted ceiling in the great room. Spacious kitchen with plenty of storage and breakfast area overlooking tranquil water views. With 2,847 sq ft of air-conditioned living space under roof, you have plenty or room for entertaining and extended family. Large windows and sliding glass doors frame panoramic vistas, infusing the space with a sense of tranquility and connection to nature. Attached 2-car garage with large storage room with AC. HOA fees include lawn care, trimming and fertilizer to give you more time to relax. Access to Lake Hartridge and the ‘Chain of Lakes’, a navigable canal system connecting 15 lakes, is obtained from the private community boat ramp and dock. This community is well known and desired by aircraft owners and flying enthusiasts as it is near Gilbert Field-Winter Haven Regional Airport, a city-owned airport that supports over 80,000 flights a year. It is also home to the Jack Brown Seaplane Base renowned as the largest and one of the oldest seaplane training and base operations in the world. Conveniently located between Orlando and Tampa with great attractions, waterfront restaurants, shopping, and some of the best fishing and ski lakes available! Welcome home to endless days of sunshine and relaxation. Please see the interactive 3D virtual tour and floor plan. Virtually staged photos are included.

247 S Lake Pansy Drive, Winter Haven

$425,000
3 Beds 3 Baths East View Pkwy SubDv. 33881 Zip Code
One or more photo(s) has been virtually staged. Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, & unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding and paddleboarding right from your backyard. With nearby slalom courses & open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds & other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms & 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort & privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with its oversized driveway & an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining & entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play & unwind in one of Florida’s most iconic lakefront settings. Book your showing today!

900 Lake Jessie Drive, Winter Haven

$819,000
3 Beds 3 Baths Waters Lake Mariam SubDv. 33884 Zip Code
Rare opportunity to own a direct-waterfront pool home on Lake Mariam, now offered at a reduced price. Set on the shores of Lake Mariam in Winter Haven, this home offers direct lake access, a private dock, and open water views from the backyard. Water views extend through much of the home, including the master bedroom, formal living room, family room, kitchen, and guest bedroom, with beautiful sunsets over the lake each evening. The home features a durable metal roof and owned solar panels, keeping maintenance low and energy costs down year-round. Whether it's coffee by the fireplace, sunset over the lake from the master suite, or an afternoon on the water, the setting delivers the lakefront lifestyle buyers are looking for. The floor plan includes three bedrooms and a spacious bonus room suited for a home office, media room, guest suite, or playroom. The kitchen anchors the home with abundant cabinetry, stainless steel appliances, granite countertops, a center island, breakfast bar seating, glass-front upper cabinets, and recessed lighting, opening into the main living space with water views from the adjoining room. The oversized 2-car garage offers ample storage for vehicles and lake gear. Outside, a private heated pool and spa overlook the water, alongside one of the longest private docks on Lake Mariam, ideal for boating, fishing, water skiing, or kayaking directly from the backyard. Situated on a 0.33-acre lot in Winter Haven's lake corridor, the home is minutes from dining, shopping, and Legoland Florida, with easy I-4 access to Tampa and Orlando. Schedule your private tour today!

1028 S Lake Mariam Drive, Winter Haven

$349,900
3 Beds 2 Baths Crystals Landing SubDv. 33884 Zip Code
Welcome to 802 Marcia Loop, a LAKEFRONT property located in southeast Winter Haven! The property includes an area on Lake Ruby right across the street! The lake is visible from the living room, kitchen, dining room, as well as the primary bedroom! Enjoy the amazing view of Lake Ruby while relaxing on the back patio, which is accessible from the living room and primary bedroom! This home is equipped with a solar panels. BONUS: SOLAR PANELS WILL NOW BE PAID OFF AT CLOSING! This will allow the buyer to benefit from the energy savings from day one! With 3 bedrooms, 2 bathrooms and over 1,500 square feet of living area this home provides ample space. This home sits on just over 1/4 acre, which is the largest lot in the community! Windows and sliding doors were replaced in 2024! Recent kitchen upgrades include: countertops, backsplash and appliances in 2024. The home is also equipped with water filtration, reverse osmosis and an ADT security system. Lake Ruby connects via canal with Lake Bess, providing more area to explore while fishing, boating, etc. Lake Ruby is a 259 acre lake and the access to Lake Bess offers enjoyment of another 146 acres of water. Both lakes have slalom courses and ramps, fitting for the “Water Ski Capital of the World”. Skiing is allowed on Lake Ruby so build a dock and bring a boat in! The laundry room provides a space to complete that chore within the comfort of your home. Winter Haven is centrally located which provides easy access to many parts of the state. The theme parks and airports of Orlando and Tampa are approximately one hour drives in their respective directions. LegoLand, Publix, Wal-Mart and the AdventHealth ER are all within 5 minutes of this home! Buyer and buyer’s agent are responsible for verifying information. Schedule your showing today!

802 Marcia Loop, Winter Haven

$299,950
3 Beds 2 Baths Timber Wood SubDv. 33880 Zip Code
Welcome to this beautifully renovated lakefront home located on Thomas Lake in Winter Haven, Florida! This charming two-story home combines modern upgrades with warm character, breathtaking water views, and lake access. Step inside to tall vaulted ceilings creating an open, spacious layout filled with natural light and prospective memories. The home features all-new flooring throughout and a completely updated kitchen showcasing stainless steel appliances, quartz countertops, brand-new cabinetry, and closet pantry, providing plenty of storage and room to cook or entertain. In the living room, you will find a cozy fireplace with a raised hearth and wood accents, adding a welcoming focal point to the downstairs. This home also features beautifully updated bathrooms and walk-in closets, as well as a brand new electric water heater and newer A/C units as of 2022 for added efficiency and comfort during those Florida summer days. Outside, you’ll find a newer roof as of 2022, a freshly painted exterior, an attached 1-car garage with a driveway, and plenty of space to enjoy the outdoors in the back yard or a day on the lake. Relax or entertain on the large rear patio, or spend a cozy night in the enclosed, two-story back porch, each offering gorgeous lake views. The third bedroom is located within the home’s loft and is equipped with a walk in closet and direct access to the upper back porch. This move-in-ready lakefront home blends those new enhancements, comfort, scenic surroundings, and the charm of living in Winter Haven, FL, making it an opportunity you won’t want to miss!

265 Lake Thomas Drive, Winter Haven

$699,900
3 Beds 3 Baths Lakewood Acres SubDv. 33880 Zip Code
Experience lakeside living in this custom-built home, perfectly situated on the shores of Lake Grassy. As you approach the property, you are greeted by a sprawling 13’x60’ front porch complete with a charming swing and ample space for entertaining. Imagine hosting gatherings here, with tables lined up as you enjoy views of the beautifully landscaped front yard. Step inside through a wide foyer that seamlessly flows into a spacious family room, where soaring ceilings amplify the sense of openness and elegance. The heart of the home is the newly renovated kitchen, featuring hickory wood cabinets with convenient roll-out drawers, modern appliances, and an eat-in area framed by a picture window offering breathtaking lake views. Adjacent to the kitchen, the formal dining room features sliding glass doors that open to a cozy back porch, creating the perfect indoor-outdoor flow for dining and relaxation. The home boasts 180 feet of lake frontage, complete with a private boat dock and concrete retaining wall, inviting endless water activities and lakeside enjoyment. Eco-friendly and cost-efficient, this home is equipped with fully paid solar panels and a private well, ensuring significant savings no utility bills. The expansive laundry room provides additional storage space, enhancing functionality. The main bedroom is a serene sanctuary with its own private lake view and sliding glass door that opens to a private lanai, offering a tranquil space to unwind. The main bedroom has on-suite bathroom, separate water closet, double sinks, jacuzzi tub, separate shower and double sinks. The second bedroom is thoughtfully designed with a dog door leading to secure dog fencing, making pet care effortless. The second and third bedrooms have walk in closets and share a convenient 2nd bathroom. Car enthusiasts or hobbyists will appreciate the oversized 35’x38’ garage, perfect for a workshop or extra storage, and includes a full bathroom. Additionally, a detached building is primed to become an in-law suite or a private home office, adapting to your changing needs. Don’t miss the opportunity to own this lakefront gem. Call for your private viewing today and start living your dream on Lake Grassy!

124 Pangola Drive, Winter Haven

$699,950
4 Beds 3 Baths Magnolia Shores SubDv. 33881 Zip Code
**Seller is MOTIVATED**Major Price Improvement** Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor living, and boating amenities. The main home features three bedrooms and two bathrooms with an open and functional layout. A bonus room with built in entertainment cabinetry and surround sound opens through double sliding doors to the pool deck, creating seamless indoor-outdoor living. The living room showcases beautiful wood beams, a wood burning brick fireplace, and triple sliding glass doors overlooking the pool and lake. Tile flooring runs throughout the main living areas, with wood flooring in the bedrooms. The kitchen is designed for everyday living and entertaining, featuring granite countertops, updated cabinetry with pullouts, a large island, built in desk space, wine refrigerator, stainless steel appliances, and a built-in oven/microwave combination. A separate guest studio apartment adds flexibility, complete with a kitchenette and triple sliding glass doors leading directly to the pool area. This space is ideal for guests, extended household needs, or flexible use. Outdoor features include a screened pool with new heater and an 8-foot depth, a spa that conveys, and a gas fireplace on the patio with underground piping in place (propane tank has been removed, but can easily be replaced by the new homeowner). The pool screen was recently replaced. The property includes a private boat dock and lift, allowing easy access to Lake Hamilton and nearby lakefront restaurants by water. Additional highlights include fruit trees in the front yard, RV parking for up to 31 feet with additional storage space, and a metal roof. Practical upgrades and systems include a new air conditioning system installed July 2024 with annual maintenance, water softener, well for irrigation, public water for the home, an inside laundry room, and a 2-car garage. The hot water heater was installed in 2011. Septic service was last completed June 2023. Solar panels are leased at $381.75 per month, with an average Duke Energy bill of approximately $30 per month. Televisions in the main living areas convey, excluding bedrooms. This lakefront retreat offers privacy, functionality, and a connection to the water, all set along beautiful winding roads in a peaceful Winter Haven setting.

3050 Crump Road, Winter Haven

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