Winter Haven Homes with Lake Front Water Frontage

Winter Haven Homes with Lake Front Water Frontage

Welcome to Winter Haven, Florida – a picturesque city nestled in the heart of Polk County, renowned for its stunning chain of lakes and vibrant community spirit. With a perfect blend of natural beauty and modern amenities, Winter Haven offers an idyllic lifestyle for families, retirees, and everyone in between.

One of the standout features of Winter Haven is its breathtaking lakefront properties. Imagine waking up to the soothing sounds of water lapping against your dock, with the sun rising over the shimmering surface of one of the many pristine lakes. Homes with lakefront frontage in Winter Haven provide not just a residence but a lifestyle filled with outdoor adventures and tranquil moments. Whether you enjoy fishing, boating, or simply soaking in the sun, these properties offer direct access to endless recreational opportunities.

In addition to its stunning homes, Winter Haven boasts a vibrant downtown area filled with charming shops, delightful restaurants, and cultural attractions. The city is also home to the famous LEGOLAND Florida Resort, making it a family-friendly destination year-round. With its warm climate, rich history, and welcoming community, Winter Haven is a place where you can truly feel at home.

If you're seeking a serene lakeside retreat, look no further than Winter Haven. Explore our selection of exquisite lakefront homes and discover the perfect property that allows you to embrace the beauty of Florida living. Your dream home awaits!

Newest Winter Haven Homes with Lake Front Water Frontage

no property photo
$309,000
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 01 SubDv. ⋅ 33884 Zip Code
BEAUTIFUL 3-BEDROOM, 2-BATH HOME IN CYPRESS LANDING ON LAKE DEXTER! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home with a 2-car garage, located in the desirable Cypress Landing community on Lake Dexter in Winter Haven! Featuring extensive recent updates, spacious living areas, and fantastic community amenities, this home offers the perfect blend of comfort, convenience, and Florida living. Extensive Recent Updates! Major improvements include a new roof and updated in 2022, along with numerous renovations completed this year. Updates include a renovated kitchen with new countertops, new bathroom vanities, updated flooring, new lighting and fans, plumbing fixtures, fresh paint and texture, new interior doors, updated trim, new electrical improvements and pluming, and new appliances, including a range, microwave, and dishwasher. A new DECA drainage system was also recently installed in the rear of the home. Upon entering, you are welcomed by an extended foyer that opens into a spacious living area. The generously sized primary suite offers sliding glass doors leading to the lanai, along with an attached primary bathroom featuring a walk-in shower and walk-in closet. Additional highlights include an impressive 26' x 11' sunroom overlooking the backyard—an ideal space for relaxing, entertaining, or enjoying your morning coffee. Enjoy the Cypress Landing Lifestyle! Community amenities include pickleball and tennis courts, a heated swimming pool, a clubhouse, a private boat ramp with water access, and a variety of social clubs and activities for residents to enjoy. Conveniently situated in the heart of Winter Haven, this home offers easy access to shopping, restaurants, entertainment, and local social events, with convenient commutes to Lakeland, Orlando, and Kissimmee. With its extensive updates, spacious floor plan, inviting living spaces, and desirable lake community amenities, this home is a wonderful opportunity to enjoy the best of Winter Haven living!

3947 Cypress Landing W, Winter Haven

260 Greenfield Road, Winter Haven
$349,900
3 Beds ⋅ 2 Baths ⋅ Cypresswood Greenfield Village SubDv. ⋅ 33884 Zip Code
Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed private POOL deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle.Tucked away on the golf course with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed split-bedroom floorplan ideal for both everyday living and hosting guests. The heart of the home features solid wood cabinetry and rich granite surfaces in the kitchen and baths, combining timeless style with durability. The primary suite is a true retreat, complete with an en suite bathroom and a spacious walk-in closet. Guests will appreciate the dedicated pool/guest bathroom, perfectly positioned for indoor-outdoor living. Step outside to the screen-enclosed pool deck and take in tranquil views of the golf course and pond—your own private oasis framed by mature landscaping. Whether enjoying a quiet morning coffee or entertaining at sunset, this outdoor space delivers year-round enjoyment. Located within a gated community with 24-hour guard service, residents enjoy access to an impressive array of amenities, including a community pool, tennis, pickleball and basketball courts, a clubhouse with restaurant, pro shop, and a fully equipped fitness center. This is more than a home—it’s a lifestyle. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is 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 for travel in less than an hour from Disney World and other Orlando attractions, the Orlando International Airport, and the gulf-side beaches of Tampa/St. Pete! Schedule your private showing today, and don't miss the opportunity to make this incredible home yours.

260 Greenfield Road, Winter Haven

5385 Hogan Lane, Winter Haven
$369,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph I SubDv. ⋅ 33884 Zip Code
Welcome to this stunning Biscayne-model home located at 5385 Hogan Lane, Winter Haven, Florida 33884, within the highly desirable Lake Ashton, a Premier Florida Retirement community in Central Florida. This beautifully maintained property offers premium upgrades, functional spaces, picturesque lake views and gorgeous Florida sunsets. Premium Interior Features include: Gourmet Kitchen with 42" cherry cabinetry with modern crown molding and large metal handles, granite countertops, a breakfast bar, an elegant tile backsplash, and window above the sink. The kitchen cabinet layout includes several banks of drawers, a stainless steel sink and an enlarged open area that flows seamlessly into the breakfast nook. The dedicated den is a highly functional space complete with a built-in Murphy bed and custom desk complex, perfect for a home office or guest room. The wall unit also has a desk that folds out easily. The Primary Suite Bath features comfort height cabinetry, granite countertops, upgraded mirrors and lighting fixtures, a garden tub, and a glass shower door enclosure. The guest bathroom is similarly appointed with a comfort height cabinet, granite counter, upgraded mirrors, and a shower/tub combo. You'll find Upgraded Flooring in the main living, dining, and dinette areas with bamboo flooring, while the kitchen, bathrooms, laundry room and den have tile flooring; plush carpeting is in the bedrooms. This home has a desirable outdoor living area. Relax on the large, screened lanai with tile floor while enjoying beautiful water views and sunsets. A professionally laid paver walkway connects the garage directly to the lanai. This home has double-paned windows, solar tubes for abundant natural light throughout the kitchen, bathrooms, laundry room, and den, and ceiling fans in every room. The Expanded Garage Space is a bonus. The generous double car garage has built-in cabinetry, an extra-long dedicated golf cart garage (8'5x29'11), a utility sink, an exterior window, and a pull-down ladder for attic storage. Additional Home Highlights: Roof Replaced 2025, A/C (2017), Separate Irrigation Meter, Extended Birdcage with Tile Flooring. Located in Lake Ashton, a Florida Retirement community offering Resort style amenities and planned activities. Lake Ashton, a 55 community in Florida, has (2) 18- Hole Golf Courses, Pro Shop, Main Clubhouse with Movie Theater, Bowling Lanes, Grand Ballroom, Card, Craft and Billiards, Outdoor Pool, Bocce, Shuffleboard, Tennis and Fitness Center. The Health and Fitness Center has an Indoor Pool, Card, Craft and Billiards, Multi-Purpose Room, Media Center, Indoor 1/2 Court Basketball, Indoor Full Court Racquetball, Pickle Ball courts and MORE! One Year Home Warranty Included. Call today to tour this home.

5385 Hogan Lane, Winter Haven

11 Lake Link Drive Se, Winter Haven
$750,000
6 Beds ⋅ 3 Baths ⋅ Lake Link Estates SubDv. ⋅ 33884 Zip Code
TIMELESS LAKEFRONT LIVING IN BEAUTIFUL LAKE LINK ESTATES: Some homes have a way of making you feel welcome from the moment you step inside. With its classic traditional architecture, rich natural wood flooring, detailed millwork and inviting living spaces, 11 Lake Link is one of those special places. Beautifully situated along the shores of Lake Link, this 6-bedroom, 3-bath lakefront pool home offers a wonderful balance of timeless character, everyday comfort and the relaxed elegance of waterfront living. A welcoming foyer introduces gracious formal living and dining rooms, beautiful settings for intimate dinner parties, holiday celebrations and special occasions. Thoughtful architectural details, warm wood finishes and generously proportioned rooms create an atmosphere both refined and comfortable. At the heart of the home, a spacious family room is anchored by a wood-burning fireplace, beautiful parquet flooring and picturesque lake views. It's easy to imagine quiet evenings beside the fire and conversations that linger long after dinner. The adjoining kitchen features rich hardwood cabinetry, granite countertops and a convenient closet pantry, while the adjacent dinette provides a comfortable setting for morning coffee and casual meals, all complemented by beautiful waterfront views. The thoughtfully arranged bedrooms offer privacy and flexibility. Overlooking the lake, the primary suite features a walk-in closet and private bath with granite countertops and a soaking tub with shower. Five guest bedrooms bring the home's total to six, offering a rare combination of space, comfort and versatility. As inviting as the interiors are, the lakefront setting is where this property truly comes into its own. A beautiful pool and a lushly landscaped, fenced backyard create a private retreat framed by mature greenery and graceful Florida cypress trees. Here, the pace of life naturally slows. Mornings begin with birdsong and reflections dancing across the water, afternoons are spent relaxing beside the pool, and evenings bring colorful Florida sunsets that transform the lake into a constantly changing landscape. A private composite dock offers an open sunning deck, a covered lounging area with TV connection, and the warm glow of market lighting that creates an inviting atmosphere for relaxing, entertaining or simply enjoying the peaceful lake views. With room to tie up a boat, the dock also provides convenient access for bass fishing, paddleboarding and leisurely sunset cruises. Significant improvements include a metal roof (2020), Pella replacement windows (2017–2019, excluding front bay window), replumbing (2015), two updated HVAC systems (2020/2024), water heater (2020), extensive attic insulation (2025), gutters (2021), new dock (2021), seawall reinforcement (2023) and refreshed backyard pavers. Ideally located near Winter Haven's medical campuses and thriving downtown, the home offers exceptional convenience for physicians, professionals and anyone seeking a peaceful waterfront retreat. Downtown Winter Haven features locally owned restaurants, boutiques, entertainment and community events, while its central location between Tampa and Orlando provides access to both metropolitan areas. A home filled with character, surrounded by natural beauty and designed for making memories. A wonderful place to experience lakefront living and an even more special place to call home.

11 Lake Link Drive Se, Winter Haven

4043 Bedford Avenue, Winter Haven
$359,900
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
UPGRADED HOME IN THE GATED RESORT-STYLE COMMUNITY OF TRADITIONS: Meticulously maintained and thoughtfully upgraded 2 bedroom, 2 bath home with a versatile den that can easily serve as a 3rd bedroom, located in the desirable Traditions at Lake Ruby community. Enjoy comfortable living and an active lifestyle in this gated 55+ community in Winter Haven. This beautifully maintained home features extensive improvements, generous outdoor living space and transferable home warranty until April of 2030. The open floor plan brings the great room and kitchen together for easy everyday living and entertaining. New laminate flooring adds warmth, while the kitchen features quartz countertops, an island with seating and pendant lighting, stainless steel appliances including a double oven with air-frying and microwave capabilities and a closet pantry. An adjoining dinette provides a casual dining spot, while the formal dining room offers an inviting setting for intimate dinners and holiday gatherings. The spacious primary suite features a tray ceiling, a walk-in closet with custom built-ins and an ensuite bath with a quartz countertop, dual sinks, a handicap accessible walk-in shower and a private water closet. The comfortably sized secondary bedroom is conveniently situated near the guest bathroom, which features a new walk-in shower. An interior laundry room with storage cabinets adds everyday convenience. Three sets of sliding doors create a natural connection to the expansive covered and screened lanai. Finished with paver flooring, this generous outdoor space offers room for relaxing, dining and hosting larger gatherings. A separate paver patio just outside the enclosure provides a convenient grilling area, while refreshed tropical landscaping enhances the setting. Enjoy added peace of mind in Florida with a new roof installed in 2024 and a 2024 Generac 24kW whole-house generator with a transferable warranty and powered by a 500-gallon buried propane tank capable of providing up to three weeks of backup power eliminating much of the stress and uncertainty associated with unexpected power outages, whether short-term or extended. Additional significant improvements made in 2023/2024 include new interior and exterior paint, new laminate flooring and a Puragain water purification system with reverse osmosis in the kitchen. The two-car garage features screen doors, epoxy flooring, a 240-volt connection for electric vehicle charging and attic stairs. Additional features include surround sound, an ADT security system, an irrigation system with a separate irrigation meter, rain gutters, a paver driveway and walkway and more. The monthly maintenance fee of $485 includes lawn care, bush and hedge trimming, exterior home painting, cable TV, internet, trash removal and access to the clubhouse and community amenities. Just a short walk from the home, the lakefront clubhouse offers a heated pool and spa, fitness center, ballroom, library, dance studio, arts and crafts studio and a computer room. Outdoor amenities include shuffleboard, basketball, tennis and bocce ball, along with a community boat ramp, dock and dog park. A new Publix located just outside the community gate makes everyday errands especially convenient, with dining and medical facilities only minutes away. Centrally located between Tampa and Orlando, this thoughtfully improved home offers an inviting opportunity to enjoy the maintenance-free lifestyle of Traditions at Lake Ruby.

4043 Bedford Avenue, Winter Haven

1921 Manor Circle Se, Winter Haven
$1,295,000
3 Beds ⋅ 3 Baths ⋅ Laha-Wa Manor SubDv. ⋅ 33880 Zip Code
Imagine waking each day to breath-taking lake views, swaying palms, spectacular sunsets, and the tranquil beauty of Lake Lulu. Quietly positioned on one of the most desirable lakes within Winter Haven's renowned Chain of Lakes, this beautifully maintained and thoughtfully updated single-story residence enjoys a private setting on 0.45-acre lot, surrounded by mature landscaping and established tropical gardens. Designed for both comfortable everyday living and exceptional entertaining, the home offers spacious, versatile accommodation with stunning lake views from the moment you enter through the front door. The flowing floor plan seamlessly connects the formal living and dining areas, with 50-inch SAMSUNG TV & rich wood flooring to the family room, kitchen, breakfast nook, and outdoor living spaces, creating an inviting atmosphere throughout. At the heart of the home is a well-appointed gourmet kitchen featuring a large center island, breakfast bar, premium stainless-steel appliances, updated Kitchen-aid double ovens with air fryer, microwave, French-door refrigerator, and dishwasher. Custom cabinetry includes soft-close drawers, pull-out shelving, glass display cabinets, wine storage, pantry space, and appliance garage. Beautiful non-slip tile flooring extends throughout the main living areas. Adjacent to the kitchen, the breakfast nook offers direct access to the pool area through sliding glass doors, while the spacious family room features a stunning Travertine fireplace, built-in SAMSUNG 50-inch television, neutral finishes, and expansive 12-foot sliding glass doors that open directly to the screened resort-style swimming pool & paved Lanai (1485sq,ft ) The laundry room is equipped with custom cabinetry, generous storage, a large linen closet, and includes a front load washer and dryer. A conveniently located half bath provides direct access to the pool and outdoor entertainment area. The fourth bedroom is currently configured as a home office. NEW (AUGUST 2026) ARCHITECTURAL SHINGLE ROOF on home, boathouse and storage shed. Owned security system. Phone, internet, and Wi-Fi connectivity throughout the home. Extensive custom cabinetry and storage solutions. Walk-in closet system in the primary suite. Landscaped with irrigation and lighting. Circular paved driveway with courtyard entrance and carriage lighting. Attached 2 car garage has staircase to large, walk-up attic for extra storage. 106ft frontage on Lake Lulu with a private dock, boathouse with lift. Direct access to Winter Haven's Chain of Lakes for boating, fishing, and water recreation. Convenient location with easy access to downtown Winter Haven, shopping, dining, LEGOLAND, Highway 27, Interstate 4. Tampa and Orlando Airports.

1921 Manor Circle Se, Winter Haven

138 Grove Branch Road, Winter Haven
$289,000
4 Beds ⋅ 2 Baths ⋅ Squires Grove SubDv. ⋅ 33880 Zip Code
PEACEFUL WATERFRONT LIVING IN SQUIRES GROVE | WINTER HAVEN, FLORIDA: Enjoy peaceful waterfront living, picturesque fountain views and the charm of small-town Florida at 138 Grove Branch Road in the Squires Grove community between Winter Haven and Eagle Lake. Situated on an oversized waterfront lot, this beautifully maintained, move-in-ready 4 bedroom, 2 bathroom home offers a wonderful combination of comfortable living spaces, thoughtful upgrades and a relaxing setting overlooking the neighborhood pond. Known for its welcoming atmosphere and traditional Americana charm, the area offers a refreshing escape from the congestion of larger cities while remaining conveniently located near shopping, dining, schools and the everyday conveniences of nearby Winter Haven and Lakeland. A screened front entry welcomes you into a spacious, thoughtfully designed interior featuring high ceilings, neutral finishes and attractive tile and laminate flooring throughout. The open great room provides a comfortable setting for everyday living and entertaining, with generous space to arrange furnishings and direct views of the waterfront setting. The adjoining kitchen offers abundant cabinetry, ample counter space, included appliances and a walk-in pantry for additional storage. Conveniently positioned just off the kitchen, the dining area enjoys beautiful views of the pond and its gently flowing fountain, creating an inviting backdrop for morning coffee, family meals and evening gatherings. The home's desirable triple-split bedroom floor plan provides excellent separation and privacy between the primary suite and guest bedrooms. Generously proportioned, the primary suite features a private en-suite bathroom with dual sinks, a walk-in shower, a spacious walk-in closet and a separate linen closet. The additional bedrooms are comfortably sized and offer flexibility for family, guests or a home office. An interior laundry room with included washer and dryer adds everyday convenience. One of the home's most appealing features is its peaceful outdoor setting. The screened rear lanai overlooks the spacious backyard and waterfront, where the gentle sounds of the fountain and visits from native birds create a relaxing atmosphere. Whether enjoying a quiet morning outdoors or unwinding at the end of the day, this inviting space captures the simple pleasures of Florida living. Vinyl privacy and picket fencing adds privacy and functionality while preserving the enjoyment of the waterfront surroundings. Numerous amenities and improvements further enhance the home's comfort, efficiency and functionality, including an upgraded indoor air quality system, water softener, whole-home surge protection, insulated garage door with automatic opener, screened front entry and rear lanai, and attractive laminate and tile flooring throughout. Additional storage improvements include an attic access ladder, attic flooring and installed shelving throughout the home and two-car garage. With its oversized waterfront lot, inviting interior, extensive improvements and convenient location, 138 Grove Branch Road offers an appealing opportunity to enjoy comfortable, move-in-ready living in one of Central Florida's charming small-town communities.

138 Grove Branch Road, Winter Haven

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