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1712 Boys Club Road, Winter Haven
$575,000
4 Beds ⋅ 3 Baths ⋅ 296854 MLS
Back-on-the-market after numerous upgrades to the 4-season porch and master bedroom. Move-in ready. Completely remodeled and given many upgrades to enhance the comfortable open lakeside living lifestyle. You can be the first to enjoy the modern open floor plan in the main living area plus lots of private spaces and storage too. Sitting on the westside of Lake Cannon on Winter Haven Chain of Lakes you're able to enjoy the the sunrises each morning from the newly opened up glassed-in (with a/c) back porch area. 2 En suite bedrooms. Easily configurable to accommodate a mother-in-law suite if needed. No HOA. City zoning allows for a detached garage. Brand new dock. Located 5 minutes from downtown Winter Haven & a county park with a boat ramp, play ground & pavilions is 2-blocks away.

1712 Boys Club Road, Winter Haven

302 Ruby Lake Lane, Winter Haven
$388,000
3 Beds ⋅ 2 Baths ⋅ 315821 MLS
PRICE REDUCTION - Welcome to this spacious and thoughtfully designed 3-bedroom, 2-bath home located in the beautifully manicured gated community of Ruby Lake in Winter Haven, close to Lego Land, Publix and Walmart.. Featuring over 2000 square feet of living space, this residence offers both comfort and functionality with generously sized rooms and high-end finishes throughout. Step inside to find soaring 11 foot, 4 inch high ceilings and elegant crown moldings enhancing the formal living room and expansive family room. The cozy fireplace in the family room adds a warm touch, while an oversized bonus/media room provides the ideal space for entertainment. Kraftmaid kitchen cabinets and Courian Countertops with upscale lighting gives a "gourmet" feeling to the kitchen. The master Suite includes a jetted tub, walk-in shower and space to unwind. Garage has an added flex room with AC, great for storage, workshop or office. Private white fenced back yard filled with flowers and mature plants. Energy efficiency comes standard with a New AC System installed in 2024, Whole House Water Filtration System outside with additional Filter under the Kitchen Sink as well as a modern Solar System with low assumable monthly payments. Tranquil, private neighborhood yet close to everything you need. Don't miss your chance to tour this well-appointed home that balances comfort, efficiency, and character in one carefully maintained setting.

302 Ruby Lake Lane, Winter Haven

4569 Mandolin Boulevard, Winter Haven
$339,000
4 Beds ⋅ 2 Baths ⋅ 316807 MLS
Stylish and move-in ready, this 4-bed, 2-bath home sits on a beautiful .32-acre corner lot in the gated Mandolin community. With 1,665 sq ft of living space, vaulted ceilings, and luxury vinyl plank flooring, it offers comfort and style at every turn. A brand-new roof is scheduled for September 2025 for added peace of mind. The open layout connects the living, dining, and kitchen areas, perfect for entertaining. The kitchen features stainless steel appliances, a wraparound breakfast bar, decorative backsplash, and generous storage. The split bedroom plan includes a spacious primary suite with walk-in closet and updated bath, plus three additional bedrooms and a refreshed second bath. Relax in the screened lanai overlooking a massive, fully fenced backyard with double-gate access—ideal for pets, play, or a future pool. Updated fixtures, a water filtration system, laundry room with LG washer/dryer, and a two-car garage complete the package. Minutes from shopping, dining, Legoland, and major routes, with easy access to both Tampa and Orlando, this home offers privacy, convenience, and charm in one. Schedule your showing today!

4569 Mandolin Boulevard, Winter Haven

216 Shelley Drive, Winter Haven
$306,900
3 Beds ⋅ 2 Baths ⋅ 308270 MLS
216 Shelley Drive is located in the sought-after community of Garden Grove. NO HOA. This 2,200+ square foot pool home is located on a corner lot. This home has lots to offer--it is a 3/2 with the formal living room currently being used as a 4th bedroom. Could easily be converted back to a living room, game room--whatever you like! The eat-in kitchen overlooks the family room. The tiled family room has a beautiful beamed cathedral ceiling. The primary bedroom is spacious with an ensuite bath with walk-in shower. The other three bedrooms share a bathroom in the hall. There is a screened-in porch off the family room that is equipped with a brick grill for all your barbeques and entertaining. The bonus room looks out at the porch also and the open, inground pool in the back yard. The bonus room could serve multiple purposes and it has a wood-burning fireplace and beamed ceilings. All rooms are nicely sized. The back yard is fenced and makes the pool very private. There is also a shed that will remain with the home. Roof and a/c were done in 2017 and pool was remarcited in 2019. Close to shopping, Legoland, I-4 and both East and West coast beaches.

216 Shelley Drive, Winter Haven

2168 Bretton Ridge Loop, Winter Haven
$281,400
4 Beds ⋅ 2 Baths ⋅ 305951 MLS
COME CHECK THIS BEAUTIFUL HOME OUT TODAY! Welcome to this well maintained property on a corner lot in the wonderful community of BRETTON RIDGE!! With low HOA, 1,560 SF, 4 beds, 2 baths, and 2 car garage, this single story HOME is all that you could ask for! The open concept living areas of the home create that special blend of relaxing and socializing with friends and family. As you enter the home, you are welcomed into the heart of the spacious living room with beautiful cathedral ceilings. The well-equipped kitchen is packed with stainless steel appliances, granite countertops, all wood cabinetry with plenty of storage, and a breakfast bar. Extending from the kitchen is the dining room which is ideal for cozying up to with your morning cup of coffee. The master suite is a welcome retreat with a walk-in closet and ensuite that inspires relaxation with the convenience of a walk in shower. Completing the home is a full-size bathroom and three additional large sized secondary bedrooms with spacious closets. The fully fenced backyard is the perfect setting for family and friend gatherings and outdoor games. The dry retention pond in the back allows for great yard drainage during the stormy seasons. Winter Haven is filled with natural beauty and fun, surrounded by recreational activities to include water sports, fishing, boating, hiking, biking and golfing. The seller is ready to negotiate, so make your offer today!

2168 Bretton Ridge Loop, Winter Haven

740 Overlook Drive, Winter Haven
$232,500
315615 MLS
Versatile Multi-Use Commercial Property in Prime Orchid Springs Location! Located on desirable Overlook Drive in the sought-after Orchid Springs area of Winter Haven, this two-story mixed-use commercial building offers exceptional opportunity and flexibility for both investors and business owners. Positioned with excellent road frontage, this property ensures high visibility and easy access. The first floor features a spacious retail or professional space, highlighted by a charming pebble stone lanai entrance—ideal for client gatherings, product displays, or outdoor seating. Inside, a welcoming reception area flooded with natural light leads to additional rooms that can be tailored to your specific business needs, whether it be office suites, treatment rooms, or studio space. Upstairs, a well-appointed apartment unit provides steady rental income, currently occupied on a 12-month lease. The residence features high ceilings (recently upgraded), modern lighting, and updated kitchen and bathroom fixtures including faucets, toilet, and appliances. Relax and unwind on the private screened lanai, a tranquil retreat overlooking the lush surroundings. Additional improvements include a new roof and added insulation (2022) for increased energy efficiency and comfort. This property combines functionality, location, and income potential—perfect for an owner-occupant or investor looking to capitalize on Winter Haven's growing commercial market.

740 Overlook Drive, Winter Haven

4622 Cypress Gardens Road, Winter Haven
$247,500
3 Beds ⋅ 2 Baths ⋅ 326194 MLS
Move-In Ready with Major Updates! Welcome home to this beautifully refreshed 3-bedroom, 2-bath, 2-car garage residence offering over 1,700 square feet of comfortable living space in the heart of Winter Haven. Featuring a NEW ROOF, a NEW HVAC SYSTEM, and stylish interior finishes throughout, this home is ready for its next owner to move right in! Inside, you'll find a spacious open living and dining area that's perfect for entertaining family and friends or simply relaxing at home. The bright and inviting sunroom provides the perfect flex space for a home office, reading nook, playroom, or additional living area while overlooking the backyard. Step outside to enjoy the screened-in back porch—an ideal spot for morning coffee or evening relaxation. The backyard also includes a storage shed, providing plenty of room for tools, lawn equipment, or hobbies. Conveniently located near shopping, dining, schools, medical facilities, and Winter Haven's renowned Chain of Lakes, this home offers an excellent opportunity for first-time buyers, seasonal residents, or investors alike.

4622 Cypress Gardens Road, Winter Haven

332 Sand Pine Trail, Winter Haven
$238,000
3 Beds ⋅ 2 Baths ⋅ 315409 MLS
*one or more photos have been digitally staged* Location, Location, Location!!! This beautiful cozy home is just a few minutes away from restaurants, shopping, hospitals, Theme Parks and more. This 3 bedrooms, 2 bathrooms home features tile floor throughout the house, and granite countertops on kitchen and bathrooms, new windows (2021) throughout the house and a upgraded primary bathroom. Its oversized lot, plus its backyard enclosed lanai, offers you, your guests or your tenants the perfect space for a Sunday BBQ. The community has NO HOA and offers a boat ramp, for those who loves the life in the water. This home will be your dream home or your perfect short/long term rental investment property. A must see property.

332 Sand Pine Trail, Winter Haven

390 16th Street, Winter Haven
$238,000
4 Beds ⋅ 3 Baths ⋅ 322485 MLS
The seller is OFFERING UP TO $14,000 toward a NEW ROOF or may apply this contribution toward the BUYER'S CLOSING COSTS, providing added flexibility and value. This spacious 4-bedroom, 3-bath ranch-style home offers an impressive amount of living space (2,178 sqft) filled with natural light and designed for comfort and flexibility. The many windows throughout the home create a bright, welcoming atmosphere, while multiple living areas provide room to spread out and enjoy. The remodeled kitchen features a refrigerator, dishwasher, and range, along with a convenient breakfast bar and adjacent dining area—perfect for everyday living and entertaining. A formal living room greets you at the front entry, and the oversized family room offers exceptional gathering space, complete with a built-in desk and direct access to the screened lanai. The generous primary suite includes a walk-in closet, garden tub, separate shower, and an additional wall A/C unit for added comfort. A desirable mini–master suite with its own private bath provides ideal space for guests, extended family, or a private home office. Built-in cabinetry throughout the home adds both character and abundant storage. Situated on a large corner lot, the expansive yard offers endless possibilities for outdoor living, recreation, or future enhancements. The chain-link fenced backyard provides security and functionality while maintaining an open feel. With no HOA restrictions, you’ll enjoy the freedom to personalize the property to suit your needs. Combining space, natural light, a sizable yard, and the advantage of no HOA, this property delivers comfort, flexibility, and room to grow.

390 16th Street, Winter Haven

413 Winter Ridge Boulevard, Winter Haven
$145,752
2 Beds ⋅ 2 Baths ⋅ 319080 MLS
Welcome to Winter Ridge Condominiums — Lakeside Living on the Winter Haven Chain of Lakes. Discover the charm of Winter Ridge, a desirable waterfront condominium community offering direct access to Lake Smart, part of the renowned Winter Haven Chain of Lakes. This inviting 2-bedroom, 2-bath home features an open floor plan with ceramic tile throughout, a galley-style kitchen equipped with a refrigerator, range, microwave, and dishwasher, plus a walk-in pantry/utility room with in-unit laundry hookups. Relax and unwind on the oversized screened lanai while taking in peaceful views of Lake Conine, perfect for morning coffee or evening unwinding. The home also includes two assigned parking spaces directly in front of the unit, with additional guest parking conveniently located near the clubhouse. Community amenities include a heated swimming pool, clubhouse, shuffleboard courts, and a fishing and boat dock—perfect for enjoying the waterfront lifestyle. The HOA takes care of exterior maintenance, roof upkeep, lawn care, common area landscaping, road maintenance, and pool and dock care, offering truly low-maintenance living. Outdoor enthusiasts will appreciate the public boat ramp across the street providing access to Lake Conine, and the nearby Lake Conine Nature Park (just 0.5 miles away), featuring walking trails, picnic areas, and scenic lake views. Centrally located near shopping, dining, and medical facilities, this property is also just minutes from Legoland and Highway 27, with easy access to Tampa and Orlando. Enjoy comfort, convenience, and lakeside living in one of Winter Haven’s most sought-after condo communities—Winter Ridge.

413 Winter Ridge Boulevard, Winter Haven

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