Winter Haven Homes with Boatable Water Water Frontage

Winter Haven Homes with Boatable Water Water Frontage

Winter Haven, located in Polk County, Florida, is a charming city known for its beautiful lakes and boatable water frontage. Situated in the heart of the state, Winter Haven offers residents a perfect blend of natural beauty and modern amenities.

With its true boatable water frontage, Winter Haven is a paradise for water enthusiasts. The city is home to over 50 lakes, including the famous Chain of Lakes, which connects 16 different lakes through a series of canals. Whether you enjoy fishing, boating, or simply relaxing by the water, Winter Haven provides endless opportunities for outdoor recreation.

In addition to its stunning lakes, Winter Haven boasts a vibrant downtown area filled with shops, restaurants, and entertainment venues. The city is also home to the renowned Legoland Florida Resort, a popular destination for families and Lego enthusiasts alike.

When it comes to real estate, Winter Haven offers a wide range of options. From cozy waterfront cottages to spacious lakefront estates, there is a home to suit every taste and budget. Whether you're looking for a permanent residence or a vacation getaway, Winter Haven's homes with boatable water frontage provide a unique opportunity to enjoy the city's natural beauty.

With its picturesque lakes, thriving downtown, and diverse real estate options, Winter Haven is a city that truly has it all. Whether you're a water lover, nature enthusiast, or simply seeking a peaceful community to call home, Winter Haven is the perfect place to settle down and enjoy the best that Florida has to offer.

Newest Winter Haven Homes with Boatable Water Water Frontage

$349,001
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to Traditions, a premier 55+ maintenance-free gated community, where resort-style living meets everyday comfort and convenience! This wonderful 2-bedroom, 2-bath home with a den offers Eco Smart construction and an exceptional location just steps from the community clubhouse and directly across the street from the boat ramp. A charming screened-in front entry welcomes you into this beautifully appointed home. Step inside to the spacious Great Room, featuring elegant crown molding and porcelain plank flooring. Oversized glass sliding doors provide an abundance of natural light and open seamlessly to the screened-in lanai, creating an effortless flow between indoor and outdoor living. The gourmet kitchen is truly a chef’s delight, showcasing timeless white shaker cabinetry accented with crown molding and brushed-nickel hardware, complemented by a beautiful glass-tile backsplash. The center island features luxurious quartz countertops and pendant lighting, creating both a stylish focal point and functional workspace. A walk-in pantry and stainless-steel appliance package provide additional convenience and storage. The charming breakfast nook offers the perfect spot for casual dining. Designed for entertaining, the open-concept floor plan allows the formal Dining Room to flow naturally into the Great Room. The versatile Den is an inviting retreat with beautiful views overlooking Lake Ruby, making it an ideal home office, reading room, or additional living space. The Primary Bedroom Suite offers a peaceful retreat, featuring a tray ceiling, wall-to-wall carpeting, and a generously sized walk-in closet. The luxurious Primary Bath features a comfort-height vanity with dual sinks, quartz countertops, private water closet, and a handicapped-accessible tiled shower beautifully finished with decorative Listello tile and glass enclosure. Throughout the home, crown molding and graceful arched entryways add architectural detail and timeless elegance. Step outside to the generously sized screened-in lanai, beautifully finished with pavers and offering a peaceful space to relax, entertain, and enjoy the Florida lifestyle. Additional features include a Laundry Room with cabinetry, washer and dryer, keyless smart-lock entry, smart thermostat, double-pane Low-E windows, AO Smith hybrid water heater, screened front entry, exterior carriage lighting, architectural shingle roof, radiant heat barrier, gutters, exterior stone facade, and paved walkway & driveway. The two-car garage features a garage door opener for added convenience. Traditions offers an exceptional active-adult lifestyle with an impressive array of amenities and planned activities. Residents enjoy a lakefront clubhouse, dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting room, library, computer room, craft room, dog park, tennis courts, basketball court, bocce, shuffleboard, fitness center, aerobics studio, and so much more. The monthly HOA fee includes lawn service, cable, internet, and exterior house painting, providing added value and making maintenance-free living truly effortless. With its coveted location near the clubhouse and boat ramp, Lake Ruby views, this property offers the perfect combination of resort-style amenities, beautiful surroundings, and everyday convenience.

4075 Bedford Avenue, Winter Haven
$237,900
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 01 SubDv. ⋅ 33884 Zip Code
One or more photos have been virtually staged Charming 3/2 in Cypress Landings on Lake Dexter! Welcome home to this adorable 3-bedroom, 2-bath property located in the highly desirable Cypress Landings community on beautiful Lake Dexter. Step inside to an inviting open floor plan featuring cathedral ceilings that make the living space feel bright, airy, and perfect for everyday living or entertaining. The large primary bedroom offers plenty of comfort with its walkin closet and a private ensuite bath complete with a convenient step in shower. Living in Cypress Landings means enjoying a lifestyle full of amenities, including: Community boat ramp, Fishing pier, Clubhouse, Heated pool, Tennis courts. All of this, plus a location that keeps you close to shopping, medical offices, dining, and more. This community does not allow short term rentals, ensuring a peaceful, residential atmosphere. A wonderful opportunity to enjoy lake access, great amenities, and a cozy home in a fantastic Winter Haven neighborhood!

4116 Fishermans Landing, Winter Haven
$89,000
Waterford Oaks SubDv. ⋅ 33884 Zip Code
Rare opportunity to own a vacant parcel in the desirable gated community of Waterford Oaks, offering the opportunity to secure sort after land in an established residential setting with HOA community amenities and convenient access to LAKE WINTERSET and the Winter Haven Chain of Lakes. A community boat ramp and dock on Lake Winterset are just a short distance away, providing convenient access for boating, fishing, and enjoying the area's interconnected waterways. This parcel offers an excellent opportunity for those looking to add land in a sought-after community, create additional privacy, or explore future possibilities, subject to HOA guidelines, zoning, land-use requirements, and county approvals. The established community setting and proximity to Lake Winterset add to the property's appeal for those seeking a Central Florida lifestyle with access to recreational amenities. Enjoy the benefits of Waterford Oaks HOA community living, along with convenient proximity to shopping, dining, major roadways, local lakes, LEGOLAND Florida, and other Central Florida attractions. With Lake Winterset access, a nearby community boat ramp and dock, gated community surroundings, and its location immediately beside the neighboring estate, this parcel presents a unique opportunity to secure land in an appealing Winter Haven location.

Waterford Oaks Boulevard, Winter Haven
$750,000
5 Beds ⋅ 4 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to an exceptional 5-bedroom, 3.5 bathroom estate in the highly desirable gated community of Waterford Oaks in Winter Haven, This distinctive home offers a 2023 ROOF; NEW EXTERIOR PAINT; and a ONE YEAR HOME WARRANTY offered by the seller, along with lake access, resort-style outdoor living, flexible living spaces, and exceptional parking. A standout feature is community access to LAKE WINTERSET and the Winter Haven Chain of Lakes. A community boat ramp and dock on Lake Winterset are just a short distance away, offering convenient access for boating, fishing, and water recreation. Situated on a beautifully landscaped corner lot, the property features mature landscaping and elegant architectural details. The property offers exceptional parking with an elegant CIRCULAR DRIVEWAY and a separate SIDE ENTRY DRIVEWAY leading to the three-car garage, providing abundant space for guests, vehicles, and recreational equipment. Inside, the spacious floor plan showcases original hardwood floors, high ceilings, multiple tray ceilings, crown molding, custom built-ins, recessed lighting, and abundant natural light. The living room features custom built-in shelving surrounding an electric fireplace, while the adjoining family room offers a custom entertainment center, built-in shelving, and large windows overlooking the screened outdoor living area. The gourmet kitchen is a true centerpiece of the home, featuring custom wood cabinetry, GRANITE COUNTERTOPS, a substantial CENTER ISLAND with prep sink, built-in appliances, gas range with decorative backsplash and pot-filler faucet, abundant counter space, and generous storage. The kitchen overlooks the pool area and connects easily to the entertaining spaces. A spacious BUTLER'S CHAMBER provides additional cabinetry, workspace, storage, and a convenient laundry area. The luxurious primary suite offers a private retreat with a tray ceiling, accent lighting, large windows, plush carpeting, and a walk-in closet. The en-suite bathroom features dual vanities, tile flooring, a deep soaking tub beneath an arched window, and a spacious walk-in shower. One additional bedroom is currently used as a dedicated pool table/billiards room, offering flexibility as a recreation space or bedroom. Upstairs, an expansive TV room or potential mother-in-law suite provides additional privacy and versatility with a microwave, refrigerator, sink, 1/2 bathroom, and walk-in closet currently used as a small office. The outdoor living space is truly one of the home's major highlights, featuring a screened-in lanai, large pool with a swim-out area, OUTDOOR KITCHEN, barbecue area with NEW BARBECUE GRILL, and spacious brick-paver pool deck. The pool enclosure was rescreened last year, creating an inviting setting for swimming, dining, relaxing, and entertaining. Additional highlights include two tankless water heaters, with one serving the primary bedroom and the other serving the remainder of the home; a private well supplying irrigation for the property and adjacent vacant land which is also available for purchase. Conveniently located near shopping, dining, major roadways, local lakes, LEGOLAND Florida, and other Central Florida attractions, this distinctive estate combines Lake Winterset access, a resort-style saltwater pool, outdoor kitchen, gourmet kitchen, three-car side-entry garage, exceptional parking, multiple entertainment spaces, flexible upstairs living, and significant recent improvements.

9513 Waterford Oaks Boulevard, Winter Haven
$235,000
2 Beds ⋅ 2 Baths ⋅ Winterset 03 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Waterfront Living • Renovated Interior • Private Garage. Imagine ending your day with a beautiful Florida sunset over Lake Winterset. This beautifully renovated 2-bedroom, 2-bath condominium offers something that is hard to find in condo living—a private 1-car garage, expansive waterfront views, and the added character of a second-floor residence with vaulted ceilings and skylights. Located in the gated Winterset community, this home combines a relaxed lakefront lifestyle with a thoughtfully updated interior that is comfortable, stylish, and move-in ready. The kitchen is truly the centerpiece, featuring abundant cabinetry, granite countertops, stainless-steel appliances, a stylish tile backsplash, and an oversized counter with generous breakfast-bar seating. The open design creates a spacious connection between the kitchen and living area. The main living area features rich wood flooring and a striking built-in entertainment center with display shelving and architectural detail. Step through the sliding glass doors and enjoy the true highlight of this home—the enclosed waterfront lanai overlooking Lake Winterset. With room for both dining and comfortable seating, this becomes an extension of the living space and an ideal place to enjoy the beauty of Florida's nature. Imagine starting your morning with coffee overlooking the lake or relaxing at the end of the day as the sun sets across the water. The views aren't simply outside your door—they become part of everyday life. Renovated throughout, this home offers a cohesive blend of comfort and style. Plantation shutters, updated bathrooms, wood flooring, and carefully selected finishes create a polished feel throughout. The primary bedroom offers beautiful lake views, while the second bedroom provides flexibility for guests, an office, or additional living space. A unique feature of this residence is the installed stair chair, providing added convenience between the garage level and the second-floor home. A 1-car garage is an especially desirable feature for condo living, providing secure parking and valuable additional storage. Having your own garage adds a level of convenience that is not commonly found with condominium living. Set within the gated Winterset community, this home offers a welcoming waterfront lifestyle surrounded by beautiful lakes, mature landscaping, and green spaces. Residents can enjoy the waterfront clubhouse, pool and spa, along with an active and social community atmosphere. Winterset provides opportunities for boating, fishing, and enjoying the peaceful waterfront setting, while remaining conveniently close to shopping, dining, entertainment, theme parks, airports, and Florida's east and west coast beaches. Whether you're looking for a full-time residence, seasonal retreat, or an easy-to-maintain Florida getaway, 809 Magnolia Place offers the rare combination of lakefront views, thoughtful renovations, vaulted ceilings, a private garage, and a lifestyle centered around the water.

809 Magnolia Place, Winter Haven
$99,500
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1144 Square ft. 2 bedroom 2 bath 1983 Fleetwood mobile home with a front facing enclosed Florida room with a view of the clubhouse and recreation grounds. The king size master bedroom has a walk-in closet and a private bathroom with step in shower. The guest bedroom also has a walk-in closet. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is partially furnished and ready to move in. The guest bedroom is not furnished. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

66 Joppa Drive, Winter Haven
$79,500
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 989 Square ft. 2 bedroom 2 bath 1984 Homes of Merit with an enclosed front facing Florida. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. The guest bedroom also has a walk-in closet. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

97 Parson Drive, Winter Haven
$184,900
2 Beds ⋅ 2 Baths ⋅ Hartridge Landing SubDv. ⋅ 33881 Zip Code
Great condo in Hartridge Landings. A premier 55+ small 42 unit custom condominium complex Walking out the front door one can find themselves only a few steps from the clubhouse, pool and the famous Chain of Lakes...Lake Hartridge. 17-lake chain of inter-connected lakes. Boating and fishing enthusiasts paradise! Well maintained. This home comes with several skylights to brighten your day. It also has several custom shelves and engineered closet built-ins. Large totally private rear patio area that's great for entertaining outside and room to add a portable spa. Large double car garage with some storage closets. New TPO roof, re-piped plumbing and a/c system in 2022. Vacant and easy to show.

2215 Starboard Drive Unit 29, Winter Haven
$134,990
1 Beds ⋅ 1 Baths ⋅ Fairview Village SubDv. ⋅ 33881 Zip Code
Welcome Home to Easy Florida Living! Come discover this beautifully maintained 2023 Skyline Park Model, installed in August 2022 and thoughtfully designed with comfort, convenience, and relaxation in mind. From the moment you arrive, you’ll appreciate the new concrete driveway, newer roof, central air, spacious storage, and inviting outdoor living opportunities. Inside, the home offers an open and comfortable layout with a large pantry, dining island, electric fireplace, walk-in shower, and a bedroom spacious enough for a king-size bed. The home is being offered with many furnishings and features, including a French-door refrigerator, electric range, microwave, washer/dryer combo, water softener, blinds, generator ready and more. The lifestyle is just as appealing! The 99-year perpetual lease is renewable for only $1, while the current $90 monthly association fee includes water, sewer, trash, seasonal lawn maintenance, heated pool access, clubhouse, and a variety of community activities. Enjoy shuffleboard, horseshoes, billiards, ping pong, and a community dock with direct canal access to Lake Henry, complete with a pier bench and fire pit. Whether you’re looking for a seasonal retreat, a comfortable Florida getaway, or a place to enjoy the relaxed community lifestyle, this one is ready for you to come see and fall in love with it! Financing Available!

7060 Fairview Village Circle, Winter Haven
$139,000
2 Beds ⋅ 2 Baths ⋅ Lake Buckeye Condo SubDv. ⋅ 33881 Zip Code
Beautifully Updated Condo with Water View in the Desirable Lake Buckeye Community! Enjoy the best of Florida living in this move-in-ready condo with a scenic water view in the sought-after Lake Buckeye Condominium community in Winter Haven. Perfect as a full-time residence, seasonal retreat, or investment property, this home offers comfort, convenience, and a relaxed lakefront lifestyle. Recent updates include new flooring in both bedrooms, new blinds throughout, updated light fixtures, a new refrigerator, range, and vent hood, convenient in-unit washer and dryer hookups, and a newly refurbished screened porch—the perfect place to relax and enjoy the peaceful surroundings. The unit also includes a designated parking space. Residents enjoy access to beautiful Lake Buckeye, along with a community pool, clubhouse, private boat ramp, fishing dock, and beautifully maintained grounds. The HOA has made significant community improvements, including new roofs in 2021, an upgraded irrigation system, well maintained building exteriors, resurfaced parking areas, and a renovated community pool. Conveniently located just minutes from downtown Winter Haven, the Chain of Lakes, Polk State College, shopping, dining, golf, medical facilities, and LEGOLAND® Florida Resort, this exceptional condo offers the perfect blend of waterfront living and everyday convenience. Don't miss this opportunity to own an updated condo with a water view in one of Winter Haven's most desirable lakefront communities!

1550 11th Street Ne Unit G6, Winter Haven
$865,000
5 Beds ⋅ 3 Baths ⋅ Eloise Woods West Lake Florence SubDv. ⋅ 33884 Zip Code
Set along the shoreline of Lake Florence, this distinctive 0.83-acre waterfront parcel extends 367 feet in depth and includes 87 feet of lake frontage. Lake Florence is an independent 74-acre lake with a county-owned park but no public boat ramp. The property’s concrete boat-launching pad, dock, boathouse, and lift provide on-site access for boating, water skiing, paddling, and fishing. The parcel contains two detached residences and is coded as Multiple SFR in Polk County property records. Together, the residences encompass 3,482 square feet of combined heated living space and 5,094 total square feet under roof, divided between a two-bedroom, two-bath primary residence with a flexible studio and a detached two-bedroom, one-bath cottage. The 2,311-square-foot primary residence, built in 1985, includes a spacious primary suite and a second bedroom configured as a den with fireplace and Murphy bed. The studio/flex room has its own side entry and an auxiliary appliance station with an 18-inch dishwasher, refrigerator and freezer drawers, ice maker, and microwave, adding flexibility for entertaining, guest accommodations, or additional living space. The recently updated kitchen features quartz countertops, a substantial island with seating for five, induction cooktop, double ovens, coffee bar, and generous pantry. Expansive sliding glass doors and the dining room’s oversized window capture sweeping views of Lake Florence. New luxury vinyl plank flooring extends throughout the main living areas, while fresh interior paint complements the recent updates throughout the primary residence. The HVAC system was replaced in 2020. The primary bath includes a steam shower and refined vanity, while the secondary bath includes an oversized quartz vanity and newly installed Kohler shower. A 30-foot lakefront deck includes a screened area for additional outdoor living space. The detached 1,171-square-foot cottage, originally constructed in 1958, includes two bedrooms, one bath, a comfortable living area, and a spacious full eat-in kitchen , with crown molding throughout. Set apart from the primary home, it provides flexible separate living or workspace while remaining part of the unified property. A spacious 15-by-14-foot screened porch overlooks the surrounding landscaping. Each residence has its own electric meter and septic system; the primary residence’s septic system was replaced in 2020. The homes share a water meter and driveway. Both residences feature concrete-block construction, new roofs, screened outdoor porches, interior laundry areas, and Ecobee thermostats. An additional (3rd) washer and dryer are located in the cottage’s attached garage. Major appliances in both residences convey with the property. The lakefront grounds provide open space for outdoor living and sunrise views across Lake Florence. Parking includes a 2.5-car carport, 1.5-car garage, and additional off-street parking. This uncommon combination of two detached residences, substantial covered area, boating infrastructure, and flexible living space distinguishes the property in Winter Haven.

2510 Cypress Gardens Boulevard, Winter Haven
$54,900
2 Beds ⋅ 1 Baths ⋅ Lakeside Ranch For Mobile Homes SubDv. ⋅ 33881 Zip Code
Welcome to Lakeside Ranch, a desirable 55+ community in Winter Haven. This charming 2-bedroom, 1-bath home offers the added benefit of land ownership with NO lot rent! Features include a newer roof and hurricane shutters for added peace of mind. Enjoy a relaxed Florida lifestyle with lake access and community boat ramps, perfect for boating, fishing, and enjoying the outdoors. A great opportunity for year-round living or a seasonal Florida retreat.

213 Lakeside Ranch Circle, Winter Haven
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