Refine Search
Map
Sort by
$875,000
5 Beds ⋅ 5 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Lakefront pool home on the Winter Haven Chain of Lakes with a detached apartment, 4 car garage, abundant open parking, RV parking pad, pool, dock and more! Perfectly positioned on Lake Roy, one of the Chain’s quietest and clearest lakes, this property delivers sunset views, calm waters, and direct boat access to 20 canal-connected lakes for endless fishing, skiing, cruising, lakefront dining, live music, and seasonal LEGOLAND fireworks. The main residence features over 3,800 sqft of living space with 4 bedrooms, 2 full baths, and 2 half baths, plus a detached 550 sqft apartment with its own living room, bedroom, and bath—ideal for guests and extended family. Inside the main home, formal living and dining spaces lead to a well-equipped kitchen with center island, breakfast bar, abundant cabinetry, and a lakeview dinette designed to capture nightly sunsets. The inviting family room—with its brick natural-gas fireplace—adds warmth and comfort for everyday living. The primary suite offers dual walk-in closets, split vanities, a jetted tub, and walk-in shower, while secondary bedrooms provide generous space and excellent storage. Outdoor living is where this property excels. Enjoy a natural gas–heated pool and spa, expansive covered and open decking, cabana bath, panoramic lake views, and a private boathouse with lift—creating the ultimate lakefront playground. A public boat ramp just one home away adds exceptional convenience. Major updates ensure peace of mind, including: new roofs on both structures (2018), complete replumbing (2019), new flooring throughout (2020), remodeled bathrooms (2020), new irrigation pump (2023), upgraded landscape lighting (2025), natural-gas pool/spa heater (2019), and a brand-new 2-ton A/C in the apartment (2025). Located between Tampa and Orlando, this property offers the perfect blend of small-town charm, recreation, and waterfront living. 157 Lake Roy Drive is more than a home—it’s a fully updated lakefront compound offering space, versatility, and true Winter Haven Chain of Lakes lifestyle.

157 Lake Roy Drive, Winter Haven
$565,000
3 Beds ⋅ 3 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Welcome to 125 Lake Roy Drive—an extraordinary, move-in-ready lakefront estate delivering the true Florida lifestyle with zero compromises and no HOA. Set on a beautifully landscaped lot with ample parking for vehicles, boats, RVs, and lake toys, this home offers unmatched flexibility and convenience for waterfront living. Perfectly positioned on the prestigious South Chain of Lakes, this single-level pool home features panoramic water views, a private boat dock with lift, a brand-new jet ski dock, and nightly front-row seats to the LEGOLAND fireworks. With effortless access to more than a dozen interconnected lakes, this is a rare opportunity to own a true waterfront retreat designed for everyday luxury and unforgettable moments. The home has undergone extensive upgrades, featuring a custom-designed kitchen with solid wood cabinetry, granite countertops, stainless steel appliances, a modern sink, and a new disposal. Both ensuite bathrooms were meticulously renovated, offering comfort and style in every detail. A brand-new HVAC system and ductwork have been installed, along with complete PEX re-piping, a new 1,000-gallon septic tank, and a five-chamber drain field, as well as a French drain across the entire driveway. Additional improvements include new flooring, fresh interior paint, upgraded trim, a new boat lift motor and cradle built for a pontoon, and a refreshed pool system for low-maintenance enjoyment. Inside, the layout offers elegance and flexibility. The primary suite is tucked away for privacy and relaxation, while the second guest suite features an en suite bathroom that opens directly to the pool—perfect for extended family, guests, or a future in-law suite setup. A wood-burning fireplace anchors the spacious living area and opens to the lanai through six sets of glass doors, creating a seamless connection to the outdoors. A light-filled sunroom offers peaceful views of the pool and lake year-round, while a private, palm-lined courtyard provides a tranquil space for morning coffee or evening reflection. The property also features two garages with space for three vehicles, as well as a dedicated carport. Conveniently located near major retail, dining, and downtown Winter Haven, this home offers a unique blend of privacy, convenience, and a true waterfront lifestyle. This property is also located near the Polk Parkway and Highway 27, giving you quick access to I-4, major metro areas, world-class theme parks, and local beaches in every direction. Evening showings are highly recommended to fully experience the brilliance of the sunset over Lake Roy, best enjoyed from the tranquil comfort of this poolside sanctuary.

125 Lake Roy Drive, Winter Haven
$395,000
4 Beds ⋅ 3 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Located in one of Southeast Winter Haven's most desirable neighborhoods, just minutes from the Chain of Lakes and Lake Summit boat ramp, this beautifully updated 4-bedroom, 3-bath pool home offers nearly 2,500 square feet of living space with **no HOA**. Designed with flexibility in mind, the home features two spacious primary suites, multiple living areas, and a beautifully remodeled kitchen with quartz countertops, soft-close cabinetry, stainless steel appliances, and a workstation sink. Step outside to the screened lanai overlooking the private pool and enjoy the fully fenced backyard - perfect for entertaining, pets, and everyday living. Major updates include a NEW ROOF (2019), HVAC (2019), HOT WATER HEATER (2019), primary bathroom remodel (2019), kitchen remodel (2021), pool heater (2022), pool pump (2024), front and backyard irrigation system (2024), and guest bathroom remodel (2025). Offering quality updates, generous living space, and an exceptional location! Schedule your private showing today!

144 Beverly Dr, Winter Haven
$358,000
4 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Perfect 4 Bed / 2 Bath Pool Home for entertaining! Don’t miss this beautifully maintained 4-bedroom, 2-bath split-plan home featuring the sought-after John Wood floor plan. Enjoy Florida living with a large screened-in pool and an oversized lanai, perfect for entertaining or relaxing outdoors. Recent updates include * remodeled kitchen and baths with Granite Counter-tops * a 7-year-old roof * 2016 A/C system, offering peace of mind and energy efficiency. The home is in excellent condition, ready for you to move in and enjoy. Ideally located in Southeast Winter Haven, just minutes from downtown, the Chain of Lakes, and the Lake Roy boat ramp – perfect for boating, fishing, and all your water adventures. Call today to schedule your showing and make this amazing pool home yours!

111 Beverly Drive, Winter Haven
$294,000
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath home offering the perfect blend of comfort, functionality, and outdoor living. *Seller will contribute $5,000 towards buyer's closing cost or interest rate buy down with an acceptable offer.* Step inside to a spacious living and dining room combination, highlighted by a wood-burning fireplace, creating a warm and inviting focal point for the home. The updated kitchen features stainless steel appliances, stylish cabinetry, and a convenient breakfast bar perfect for casual dining or entertaining. The private primary suite offers a relaxing retreat with a walk-in closet and en-suite bathroom complete with a walk-in shower. Two additional guest bedrooms and a well-appointed hall bath with tub/shower combo provide ample space for family or visitors. Outdoor living truly shines with a screened lanai featuring a hot tub, overlooking the expansive fenced backyard designed for entertaining. Enjoy the above-ground pool with a wooden stairway deck, cozy fire pit area, and additional storage shed. All creating the ideal setting for gatherings or peaceful evenings at home. Additional highlights include a spacious two-car side-entry garage with laundry area, plus bonus office/workshop/storage space, as well as a one-car carport perfect for boat or camper parking. SOLAR power helps keep utility costs low, adding efficiency to this exceptional property! Solar will be paid in full at the time of closing! Conveniently located just steps from Lake Summit Public Boat Ramp and minutes from Cypress Gardens Boulevard, this home offers easy access to recreation, shopping, dining, and more. A rare opportunity to enjoy space, convenience, and lifestyle all in one remarkable property.

430 Hillcrest Drive Se, Winter Haven
$220,000
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Virtually Staged. Fully renovated home nearing completion! This beautiful property has undergone a complete renovation and is almost finished—just a few minor touches remain. Featuring modern updates throughout, this home offers a fresh, stylish feel and is perfect for buyers looking for move-in ready with final details underway. Don’t miss the opportunity to own a beautifully updated home in Winter Haven!

132 Miller Drive, Winter Haven
$170,000
3 Beds ⋅ 2 Baths ⋅ Eloise Woods Lake Roy Unit SubDv. ⋅ 33884 Zip Code
Discover the charm and potential of this 3-bedroom, 2-bathroom single-family home, originally built as the orchard home for the former orange grove that once filled this neighborhood. Situated on a spacious 0.30-acre lot, this 1,445 sq. ft. property offers a rare opportunity for investors or homeowners looking to add value with finishing touches. The home is located in an X Flood Zone (no flood insurance required) and comes with NO HOA and NO CDD, giving you the freedom to enjoy your property your way. From the front yard, take in a partial view of Lake Summit, part of the beautiful Chain of Lakes. A public boat ramp just down the street makes lake access quick and convenient - bring your boat, jet skis, or other water toys; there’s plenty of room for parking right out front. Several important updates have already been completed, including a new HVAC system in 2017 and a partial roof replacement in 2017. The kitchen features 2012 appliances, and the sellers are leaving a brand-new range hood (still in box) for the new owner to install. The primary bathroom also includes a brand-new shower head (still in box) ready to be added. With renovations started but not yet completed, this property is perfect for anyone looking to customize a home with character or expand an investment portfolio. Don’t miss this chance to own a piece of local history with fantastic location perks and endless potential.

412 W Lake Summit Drive, Winter Haven