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4171 Rolling Oaks Drive, Winter Haven
$190,000
3 Beds ⋅ 3 Baths ⋅ P4940221 MLS
Welcome to this beautifully maintained 3-bedroom, 3-bath home located in the desirable Oakwood Estates, a gated 55+ community in Winter Haven, Florida! This spacious home offers an inviting open floor plan with comfortable living and dining areas, perfect for everyday living and entertaining. The kitchen features ample cabinetry, generous countertop space, and a functional layout. Each of the three bedrooms offers its own bathroom and walk-in closet, providing comfort, privacy, and convenience for family and guests. Enjoy the enclosed patio, ideal for relaxing or entertaining year-round. Additional features include a covered carport, a spacious workshop, and a dedicated laundry area. This home has numerous upgrades throughout and has been lovingly maintained! BEST OF ALL, YOU OWN THE LAND — NO LOT RENT! Enjoy the benefits of ownership with only a low monthly community fee. CO-OP COMMUNITY Oakwood Estates offers an active lifestyle with exceptional amenities, including a clubhouse, two swimming pools, fitness center, shuffleboard, tennis courts, and a full calendar of social activities. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers the perfect combination of comfort, convenience, and community living. Don’t miss this wonderful opportunity to enjoy Florida living at its finest! Schedule your private showing today! Watch the short video and explore the 360° Interactive Aerial Virtual Tour for an even closer look at this home and its surroundings. Enjoy the freedom to zoom in and out, explore the property from every angle, and see as far as the eye can see!

4171 Rolling Oaks Drive, Winter Haven

Listing courtesy of STACEY TOWNS REALTY LLC. 863-422-1585

1085 Brenton Manor Drive, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ S5159890 MLS
Virtually Staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom single-story home in a highly desirable Winter Haven community with low HOA fees! Built in 2015, this property features complete ceramic tile flooring throughout, a new roof installed in 2024, Paid Off Solar Panels and a fully fenced backyard for added privacy. The open living area highlights a custom 3D feature wall with a fireplace, creating a cozy and stylish focal point. Complete with a 2-car garage and all appliances included, this home offers modern comfort and key upgrades. Located in the vibrant Chain of Lakes region near boating and outdoor recreation, plus just 20 minutes from LEGOLAND Florida Resort and 30 miles from Walt Disney World. Schedule your showing today!

1085 Brenton Manor Drive, Winter Haven

Listing courtesy of KELLER WILLIAMS REALTY AT THE LAKES. 407-566-1800

5203 ORCHID TREE LANE, Winter Haven
$39,990
2 Beds ⋅ 2 Baths ⋅ 12034941 MLS
A view of the community tea house will provide a distinctive backdrop to this two-bedroom, two-bathroom manufactured home at 5203 Orchid Tree Lane in Winter Haven. Offered as an estate sale, this new listing is ideal for buyers prepared to give the residence a little attention while enjoying its wonderful floor plan. The seller is seeking a quick closing. An air-conditioning system installed in 2025 provides a significant recent improvement, and the stove was added in February 2025. Most furnishings will remain with the home, helping make the transition easier. Certain items are excluded, so buyers should request the complete list from the listing agent before submitting an offer. Independent inspections are encouraged to assess the property's present condition and any desired repairs or updates. Winter Haven Oaks is a 55+ community offering two clubhouses, two heated swimming pools, pickleball courts, an on-site exercise facility, planned activities, and neighborhood events. Monthly lot rent is currently $568 and will remain at the seller's existing rate through the end of the year. After that, lot rent will adjust to the community's market rate. The pet policy allows up to two pets, each weighing 40 pounds or less. Prospective residents should verify park approval procedures, regulations, and current fees. Located on Winter Haven's southwest side, the community provides convenient access to Polk Parkway and Highway 60. Publix Super Market at Spirit Lake Crossing, a boat launch, public transportation, and the Winter Haven train station are also nearby. Arrange your private showing today. Visit the listing agent's website to explore the virtual tour, then schedule a private, in-person showing! Out of town? No worries! Virtual showings are available, and paperwork with our company can be completed remotely. Feel free to call, text, or email me. I look forward to helping you call your new house a home! All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Our company does not and cannot guarantee or warrant the accuracy of this information or the condition of this property. Measurements are approximate. Some photographs may have been digitally enhanced and may not reflect the property's current appearance. The buyer assumes full responsibility for obtaining current lot rent, fees, and pass-through costs, as well as all rules, regulations, and pet policies associated with the community, park, or home, directly from the community or park manager. Our company is not responsible for quoting these fees or policies. Pricing excludes administrative fees, tags, state and county taxes, and title fees. Financing is available through third-party lenders. Please contact the sales agent for additional information.

5203 ORCHID TREE LANE, Winter Haven

Listing courtesy of Chrissy Walter with Sunset Home Sales

3947 Cypress Landing W, Winter Haven
$304,000
3 Beds ⋅ 2 Baths ⋅ TB8559476 MLS
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

Listing courtesy of LING REALTY, LLC. 813-731-5415

718 Eagle Landing Boulevard, Winter Haven
$339,998
4 Beds ⋅ 3 Baths ⋅ O6451407 MLS
Welcome to 718 Eagle Landing Boulevard, a stunning, nearly new 4-bedroom, 2.5-bathroom home that perfectly blends modern style, comfort, and peaceful surroundings! Built just three years ago and barely lived in, this beautiful home has recently undergone fantastic upgrades, including brand-new luxury vinyl flooring throughout all bedrooms and the staircase, with absolutely NO CARPET anywhere in the home! Situated on one of the most desirable lots in the community, this home enjoys a beautiful, wide-open wooded backdrop with NO REAR NEIGHBORS, offering a rare sense of privacy and tranquility. Tucked away toward the quiet rear of the neighborhood, its peaceful setting makes it feel like your own private retreat. Step inside and immediately appreciate the sleek, modern interior, inviting living spaces, and abundance of natural light that fills the home. The thoughtfully designed layout offers four generously sized bedrooms, 2.5 bathrooms, and a spacious garage, providing plenty of room for comfortable everyday living. The oversized primary suite is a true highlight, featuring an exceptionally spacious bedroom, a generous walk-in closet, and an additional storage or closet area for even more convenience. Located in beautiful Winter Haven, famously known as the Chain of Lakes City, this home places you in one of Central Florida's most charming destinations, celebrated for its picturesque lakes, outdoor recreation, and relaxed Florida lifestyle. Enjoy convenient access to Chain of Lakes Park, a recreational destination near Lake Lulu offering sports facilities, open green spaces, and opportunities to enjoy the outdoors. Just a short drive away, discover the excitement of LEGOLAND Florida Resort and the new SEA LIFE Florida Aquarium, along with a wonderful variety of shopping, dining, and entertainment options. Whether you're drawn to lakeside adventures, outdoor activities, or local attractions, Winter Haven offers something for everyone! With its fresh upgrades, contemporary finishes, exceptional lot, and barely lived-in condition, this home offers the look and feel of new construction without the wait! Whether you're enjoying the bright, welcoming interior or the peaceful wooded views out back, every detail makes this property a wonderful place to call home. Homes with this combination of privacy, location, condition, and modern upgrades are hard to find! Don't miss your opportunity to make this exceptional home yours. Schedule your private showing today!

718 Eagle Landing Boulevard, Winter Haven

Listing courtesy of M2M REALTY. 407-401-2275

1638 Seth Drive, Winter Haven
$408,888
5 Beds ⋅ 3 Baths ⋅ S5159911 MLS
Room to spread out in Pinnacle Point! Built in 2022, this two-story Winter Haven home offers 5 bedrooms, 3 full bathrooms, and approximately 2,892 square feet of heated living space on a 0.17-acre corner lot. The living room and kitchen are located on the first floor, while the primary bedroom is upstairs. A two-car attached garage provides parking and storage space. With five bedrooms, there’s flexibility for guests, a home office, or hobbies. Enjoy no CDD fees and an HOA fee of $214 per quarter. Located in Central Florida between Tampa and Orlando, Pinnacle Point offers convenient access to shopping, dining, schools, parks, and medical facilities. Nearby LEGOLAND Florida Resort adds another option for recreation, while access to major highways connects you to destinations throughout the region.

1638 Seth Drive, Winter Haven

Listing courtesy of REAL BROKER, LLC. 855-450-0442

593 Terranova Circle, Winter Haven
$359,000
3 Beds ⋅ 2 Baths ⋅ O6450720 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bath home in the desirable gated community of Terranova! Featuring an open floor plan, vaulted ceilings, and a private screened and heated pool, this home offers comfortable Florida living. Enjoy attractive landscaping with Naval orange and Clementine trees, a screened front porch, energy-efficient Pella windows, and a spacious living room with built-in shelving. The kitchen features ample counter space, appliances, and a breakfast bar overlooking the living area. A separate breakfast nook offers flexible space for dining or a home office. The split-bedroom floor plan provides privacy, with two guest bedrooms and a full bath on one side and a spacious primary suite on the other. The primary suite features dual vanities, a garden tub, a separate shower, and a walk-in closet with custom shelving. The fully fenced backyard features an enclosed lanai, heated screened pool, spacious pool deck, and storage shed. Recent updates include a 2017 roof, upgraded A/C (2014), replaced flooring, upgraded front door, French doors, new garage door opener, and brand-new pool screens. Additional features include a 2-car garage, washer and dryer, and select furnishings, including Sleep Number beds, recliners, and outdoor furniture. Meticulously maintained and ready to enjoy, this Terranova home is a must-see!

593 Terranova Circle, Winter Haven

Listing courtesy of LA ROSA REALTY PREMIER LLC. 407-401-9076

1096 Carefree Cove Drive, Winter Haven
$199,000
4 Beds ⋅ 2 Baths ⋅ A4710224 MLS
**PRICED TO SELL! 4 BEDROOMS, 2 BATHROOMS, NO HOA, AND MAJOR UPDATES ALREADY COMPLETED! ** Don't miss this fantastic opportunity to own an affordable home in Winter Haven! This spacious 4-bedroom, 2-bathroom home offers plenty of potential with several major improvements already taken care of, including a **NEW ROOF IN 2022, COMPLETE REPIPE IN 2023, AND NEW WINDOWS IN 2023!** While the home could benefit from some cosmetic updating and personal touches, the big-ticket improvements have already been completed, giving the next owner a great head start. Enjoy the freedom of **NO HOA** and a convenient location near shopping, dining, schools, and major roadways. Whether you're a first-time homebuyer looking to build equity, a buyer wanting to make a home their own, or an investor searching for their next opportunity, this property checks all the boxes! **PRICED EXTREMELY COMPETITIVELY TO REFLECT THE COSMETIC UPDATES NEEDED AND SELL QUICKLY!** Opportunities like this don't come around often at this price point. Schedule your showing today and see the potential for yourself!

1096 Carefree Cove Drive, Winter Haven

Listing courtesy of FLATFEE.COM. 954-965-3990

221 Mandolin Drive, Winter Haven
$330,000
4 Beds ⋅ 2 Baths ⋅ L4965776 MLS
LIKE NEW!!! Don't miss this 4 bedroom, 2 bath home centrally located in Winter Haven, FL in the GATED COMMUNITY OF MANDOLIN. So many NOTABLE UPDATES in 2026 including: NEW ROOF (TAMKO TITAN SHINGLES), NEW LEVEL 3 GRANITE IN KITCHEN AND BOTH BATHROOMS, NEW SINKS, NEW KOHLER TOILETS, NEW FIXTURES, NEW INTERIOR PAINT, NEW FANS, NEWLY FINISHED GARAGE FLOOR, AND NEWLY LANDSCAPED LAWN! This OPEN CONCEPT, SPLIT PLAN is light and bright and very inviting. The OVERSIZED LOT gives you plenty of room with a length of (125 ft deep and 92 feet in width). This neighborhood is COMPLETELY BUILT OUT and VERY ESTABLISHED. The kitchen features STAINLESS APPLIANCES and is perfect for entertaining guests with it's central location. The back area is COMPLETELY PRIVATE with vinyl fencing for all your friends/family gatherings. Shopping, medical, restaurants, and LEGOLAND, FL are within minutes of this centrally located home with so many updates!!!

221 Mandolin Drive, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 863-294-7541

2303 Jagger Lane, Winter Haven
$355,000
4 Beds ⋅ 2 Baths ⋅ G5118766 MLS
Virtually Staged. Move-in ready and built in 2024! This beautifully maintained 4-bedroom, 2-bath home offers nearly 1,900 sq. ft. of thoughtfully designed living space with an open-concept layout and desirable upgrades throughout. The spacious kitchen features quartz countertops, stainless-steel appliances, a large center island, and pantry, opening seamlessly to the living and dining areas. Tile flooring enhances the main living spaces, with carpet in the bedrooms. Additional features include an epoxy-finished garage floor, rain gutters, security cameras that convey, and solar panels. Enjoy Florida living on the enclosed screened lanai, complete with roll-down shades and patio furniture that convey, overlooking a fully fenced backyard. Located just minutes from Lake McLeod and a public boat dock, with convenient access to shopping, dining, schools, and major roadways. No CDD, low HOA fees that include high-speed internet, and a seller-provided one-year home warranty! A wonderful opportunity to own a move-in-ready home with valuable upgrades already in place. Schedule your private showing today!

2303 Jagger Lane, Winter Haven

Listing courtesy of HOMESMART. 407-476-0461

283 Putter Circle, #283 Unit #283, Winter Haven
$64,900
2 Beds ⋅ 2 Baths ⋅ 12033622 MLS
2 Bed | 2 Bath | 1536 square foot | $64,900 (Swiss Golf and Tennis- Lot 283) Enjoy golf course and pond views and easy living in this beautifully maintained, fully furnished home in a highly desirable 55+ community! Inviting curb appeal and lovely landscaping welcome you to a turnkey retreat with two separate living areas, offering plenty of space to relax and entertain. Roof replaced in 2023. The open kitchen features a large pantry, while a wet bar makes hosting a breeze. Retreat to the expansive primary suite with an ensuite bath featuring a walk-in shower and garden tub. The spacious lanai overlooks the golf course-the perfect setting for morning coffee or unwinding at the end of the day. A large storage shed with AC, oversized driveway, and generous carport provide ample storage and parking, while an entry ramp adds everyday convenience. Fully furnished and ready to enjoy, this home makes settling into your next chapter easy. This home gives you access to a relaxed, resort-style lifestyle. Enjoy the beautifully maintained 18-hole golf course. One-year FREE golf membership with your purchase! Unwind at the heated pool and spa overlooking beautiful Lake Henry. The community also features an on-site restaurant, and pub. Residents also enjoy a variety of recreational activities including tennis, pickleball, and shuffleboard. Call today to schedule a tour!

283 Putter Circle, #283 Unit #283, Winter Haven

Listing courtesy of Brandi Sappington with CRF Communities

915 Hart Lake Court, Winter Haven
$520,000
4 Beds ⋅ 3 Baths ⋅ L4965885 MLS
Virtually Staged. Discover this beautifully upgraded 4-bedroom, 3-bath home at 915 Hart Lake Court in Winter Haven. Located in a private gated community across the street from Chain of Lakes Elementary School, the home is also just minutes from LEGOLAND® Florida Resort and approximately 10 minutes from U.S. Highway 27. The open-concept layout features elegant snow-color cabinetry and granite countertops throughout. The private primary suite is situated at the opposite end of the home and includes a spacious walk-in closet, a large walk-in shower, and a customized makeup vanity. A generous laundry room includes a built-in home office and is conveniently located between the kitchen and pantry. The lanai features an additional bonus room with double French doors while retaining space for outdoor living. The adjoining area offers potential to be enclosed and configured as an in-law suite, subject to buyer verification and any required approvals. Additional highlights include a three-car garage, ample parking, and finished attic space providing extra storage. **Pride of ownership is evident throughout this meticulously maintained home, with the owner’s thoughtful care and attention to detail reflected in every space. The owner is an active real estate agent.** Photo's coming soon.

915 Hart Lake Court, Winter Haven

Listing courtesy of DALTON WADE INC. 888-668-8283

260 Greenfield Road, Winter Haven
$349,900
3 Beds ⋅ 2 Baths ⋅ P4940214 MLS
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

Listing courtesy of JOHN WOOD REALTY, INC.. 863-324-9663

937 Cattleman Street, Winter Haven
$340,000
4 Beds ⋅ 2 Baths ⋅ 12028865 MLS
Welcome to this beautifully maintained, nearly new 4-BEDROOM, 2-BATHROOM home in the desirable INMAN GROVES community! Built in 2023 by D.R. Horton, this popular CALI FLOOR PLAN offers 1,828 square feet of thoughtfully designed living space with an open-concept layout perfect for both everyday living and entertaining. The spacious kitchen features SOLID SURFACE COUNTERTOPS, STAINLESS STEEL APPLIANCES, abundant cabinetry, a large island with seating, and overlooks the dining and living areas, creating a bright and inviting gathering space. The private owner's suite includes a generous walk-in closet and an en-suite bath, while three additional bedrooms provide flexibility for family, guests, or a home office. Additional highlights include ceramic tile flooring in the main living areas, an inside laundry room, energy-efficient construction, smart home features, a two-car attached garage, and an irrigation system. Step outside to enjoy the backyard with plenty of space to relax, entertain, or create your own outdoor oasis. Conveniently located near shopping, restaurants, schools, medical facilities, and major highways, this home also offers easy access to Downtown Winter Haven, LEGOLAND Florida Resort, and ORLANDO or TAMPA via nearby US-27 and I-4. Don't miss this opportunity to own a move-in-ready home in one of Winter Haven's growing communities!

937 Cattleman Street, Winter Haven

Listing courtesy of Isabelle Maye with Florida Properties Group

6125 Pebble Beach Boulevard, Winter Haven
$425,000
3 Beds ⋅ 2 Baths ⋅ P4940136 MLS
Welcome to the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this impeccably maintained 3-bedroom, 2-bath home combines exceptional quality, thoughtful design, and beautiful pond views to create an inviting place to call home. From the attractive quoin corners that enhance the front elevation and the fresh exterior paint, including the soffits and gutters, to the full-width paver driveway, the home makes an outstanding first impression. River stone accents in the flower beds add a crisp, polished appearance, while the impressive 32’ x 15’ bronze-screened veranda provides the perfect setting to relax, entertain, and enjoy tranquil views of the expansive pond. Step inside and discover a clean, bright, and welcoming interior designed for comfortable everyday living and gracious entertaining. Tasteful 18” x 18” tile flooring flows throughout the main living areas, complemented by comfortable carpeting in the bedrooms, and ceiling fans throughout the home add to its appeal. The beautifully appointed kitchen features attractive Chiffon-colored maple cabinetry with abundant storage, including a bank of drawers, rollout trays, distinctive cabinet bump-ups and bump-outs, a dedicated refrigerator cabinet, and decorative cove lighting. Granite countertops are beautifully complemented by pendant lighting above the island, while fingerprint-resistant stainless-steel appliances provide a stylish, modern touch. There is ample room at the kitchen counters for entertaining guests. A spacious walk-in pantry offers additional storage and convenience. The same quality maple cabinetry and granite countertops continue into both bathrooms and the laundry room, creating a cohesive, upscale look throughout the home. Five pocket doors enhance the flow between rooms while making excellent use of available space. The primary bedroom features black-out shades for a restful night’s sleep. The primary bathroom is a welcoming retreat, featuring dual vanities and a spacious, tiled walk-in shower with custom fixtures. Throughout the living room, kitchen, and expanded screened veranda, peaceful pond views provide a beautiful backdrop for everyday living. The two-car garage is complemented by a separate golf cart garage, making it easy to enjoy all that Lake Ashton has to offer. As an added benefit, this Green Home incorporates energy-efficient features designed to enhance comfort and help reduce energy costs. With more than $51,000 in custom builder upgrades, this exceptional property offers quality, convenience, and value that truly deserve an in-person visit. Beyond your front door, the remarkable Lake Ashton lifestyle awaits, with two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, pickleball courts, bowling alley, and an abundance of activities and amenities designed to make every day more enjoyable. Combining a beautifully maintained home, serene pond views, thoughtful upgrades, and an outstanding active-adult lifestyle, this is a wonderful opportunity to enjoy the very best of Florida living. Schedule your private showing today and discover everything this special Lake Ashton home has to offer!

6125 Pebble Beach Boulevard, Winter Haven

Listing courtesy of GLOBAL LIFESTYLE LLC. 727-537-6242

825 Sunningdale Ct., Winter Haven
$95,000
2 Beds ⋅ 2 Baths ⋅ 12033495 MLS
2 Bed | 2 Bath | 1560 sq. ft.| Lot 13 | $95,000 Step into this beautiful one-of-a-kind home at Four Lakes Golf Club. This home has a large driveway with ample space between the home and the storage shed for outside entertaining. As you enter the home you are greeted with a kitchen-dining room combination with newer kitchen cabinets and granite countertops. The dining room flows into the living room and then onto a family room which has golf course and pond views. The master bathroom has a beautiful custom built shower and vanity. The spare bedroom has a murphy bed and is at the other end of the home. The air condition was just installed. At this price this home will not last long. This home comes with one year free golf and a golf cart.

825 Sunningdale Ct., Winter Haven

Listing courtesy of Cheryl Dobbs with CRF Communities

5385 Hogan Lane, Winter Haven
$369,000
3 Beds ⋅ 2 Baths ⋅ P4940148 MLS
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

Listing courtesy of LAKE ASHTON REALTY INC.. 863-409-6899

11 Lake Link Drive Se, Winter Haven
$750,000
6 Beds ⋅ 3 Baths ⋅ L4965546 MLS
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

Listing courtesy of THE STONES REAL ESTATE FIRM. 863-412-2080

128 Lagoon Road, Winter Haven
$340,000
4 Beds ⋅ 2 Baths ⋅ TB8557043 MLS
* NO HOA * * NEW ROOF 2024 * * NEW PLUMBING * * REMODELED PRIMARY BATHROOM * * QUARTZ COUNTERTOPS * * FULLY FENCED BACKYARD * Beautifully updated and move-in ready, this 4-bedroom, 2-bath home with a 2-car garage is tucked away in a quiet neighborhood just minutes from Lake Ned. Designed for comfortable everyday living and effortless entertaining, this well-maintained home features numerous upgrades throughout. The heart of the home is the renovated kitchen, showcasing elegant quartz countertops, an oversized copper farmhouse sink, abundant cabinetry, and generous workspace for cooking, gathering, and hosting family and friends. New light fixtures throughout the home provide a fresh, modern feel, while durable tile and laminate flooring throughout means no carpet and easy maintenance. The spacious primary suite offers a peaceful retreat with direct access to the screened porch, creating the perfect indoor-outdoor living experience. The remodeled en-suite bathroom features stylish finishes and thoughtful updates designed for both comfort and functionality. Step outside to the fully fenced backyard, offering ample space for pets, play, gardening, outdoor entertaining, or even the addition of a future storage shed. Whether you're enjoying morning coffee on the porch or hosting weekend gatherings, this outdoor space is ready to fit your lifestyle. Major improvements provide peace of mind for years to come, including a new roof installed in 2024 and new plumbing in 2026. Conveniently located near Lake Ned, local parks, shopping, restaurants, and everyday conveniences, this exceptional home also offers easy access to major roadways and area attractions. Measurements are approximate. Information is believed to be accurate but not guaranteed. Schedule your private showing today before this wonderful home is gone!

128 Lagoon Road, Winter Haven

Listing courtesy of COLDWELL BANKER REALTY. 813-977-3500

922 Martin Luther King Boulevard Ne, Winter Haven
$220,000
3 Beds ⋅ 2 Baths ⋅ O6450701 MLS
This property presents an excellent opportunity for those looking to combine location, space, and a beautiful view of Lake Idyl. Its open and inviting setting adds a special touch, offering great potential to enjoy and personalize the outdoor areas—whether creating a cozy courtyard, relaxing entertainment space, or fire pit area. The residence features 3 bedrooms, 1 full bathroom, and 1 half bathroom, along with the valuable advantage of NO HOA, providing greater flexibility to make the property your own, enhance the outdoor living areas, or explore future expansion possibilities. Conveniently located along a main road in Winter Haven, the property offers easy access to schools, shopping, services, and other local amenities. Whether you are looking for a place to call home or an investment property with potential, this home offers an attractive combination of location, flexibility, and lifestyle.

922 Martin Luther King Boulevard Ne, Winter Haven

Listing courtesy of AROD PARTNERS REALTY. 407-627-7621

3789 Giorgio Drive, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ P4940205 MLS
Welcome to 3789 Giorgio Dr, a beautifully maintained 2024-built home in the desirable Villamar community of Winter Haven. This 3-bedroom, 2-bath residence offers an open and functional floor plan with a spacious great room, dedicated dining area, and modern kitchen designed for easy everyday living and entertaining. A versatile flex room provides the perfect space for a home office, hobby room, or additional living area. The private primary suite offers a comfortable retreat, while the attached 2-car garage provides convenient parking and storage. Enjoy the benefits of Villamar living with resort-style amenities including a community pool, playgrounds, and parks. Conveniently located near Winter Haven's renowned chain of lakes, shopping, dining, and area attractions including LEGOLAND Florida. With its newer construction, energy-efficient features, modern layout, and community amenities, this home offers an excellent opportunity for buyers seeking a move-in-ready property in Central Florida.

3789 Giorgio Drive, Winter Haven

Listing courtesy of DALTON WADE INC. 888-668-8283

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