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3991 Island Lakes Drive, Winter Haven
$540,000
4 Beds ⋅ 3 Baths ⋅ Island Lakes SubDv. ⋅ 33881 Zip Code
Welcome to your own private retreat in the desirable Island Lakes community of Winter Haven! This spacious 4-bedroom, 2.5-bathroom home blends comfort, style, and Florida living at its best. Step inside to a thoughtfully designed floor plan that offers plenty of room for both everyday life and entertaining. The heart of the home features a living area and a modern kitchen perfect for family gatherings and weekend get-away. Enjoy year-round relaxation in your screened-in pool and spa, ideal for unwinding after a long day or hosting summer pool parties. Beyond the pool, a private dock gives you direct access to the Winter Haven Chain of Lakes—perfect for boating, fishing, or soaking in the sunsets right from your backyard. Property has been recently appraised don’t miss out.

3991 Island Lakes Drive, Winter Haven

4225 Shadow Wood Court, Winter Haven
$540,000
5 Beds ⋅ 3 Baths ⋅ Shadow Wood SubDv. ⋅ 33880 Zip Code
No HOA or CDD fees! This expansive 3,600 sq. ft. residence is perfectly designed for a multi generational family with a mother in-law suite! With 5 bedrooms and 3 bathrooms, this home offers ample space for everyone, including a huge family room looking out on the back deck and pool area! There is also a large bedroom with it’s own full bath that would make a great mother in-law suite! Key Features: Dive into the refreshing pool! Ideal for those hot summer days or evening swims under the stars. A huge family room serves as the heart of the home, perfect for gatherings, movie nights, or just relaxing. The formal living and dining rooms provide an upscale setting for entertaining guests or enjoying family dinners. Conveniently located off the kitchen, the dinette is perfect for casual meals and morning coffee. Equipped with a gas stove, this kitchen is a chef's delight, ready for preparing culinary masterpieces. Benefit from a tankless gas water heater, ensuring endless hot water and energy efficiency. The master suite features a spacious walk-in closet and an en-suite bath, offering a private sanctuary. A second large bedroom also includes an en-suite bath, providing comfort and privacy for guests or family members. This remarkable home combines functionality and lots of space, making it the perfect place for creating lasting memories. Don't miss the opportunity to own this entertainer's dream home! Schedule a tour today and experience the beauty and comfort for yourself. Irrigation system is a private well, so no high water bills to have a lush yard! Shed out back for extra storage and a fully fenced back yard!

4225 Shadow Wood Court, Winter Haven

472 Archaic Drive, Winter Haven
$538,000
4 Beds ⋅ 3 Baths ⋅ Village Spirit Lake Ph 01 SubDv. ⋅ 33880 Zip Code
Lake-access living meets modern comfort in this beautifully updated corner-lot home. Welcome to 472 Archaic Drive, originally custom built, this updated 4-bedroom, 3-bath home is situated on a corner lot in one of Winter Haven's most desirable gated communities. With a heated pool, fully fenced yard, oversized garage with tool shed/workshop, and access to outstanding neighborhood amenities, this almost 2,800 sqaure foot home offers the perfect combination of comfort, style, and functionality. You'll appreciate the spacious layout, soaring ceilings, abundant natural light, and thoughtful upgrades throughout. The stunning chef-inspired kitchen serves as the heart of the home, showcasing abundant 42" custom cabinetry, luxury stone countertops, a large center island with additional sink, stainless steel appliances, and a stylish subway tile backsplash, a walk-in pantry, and breakfast nook. Thoughtfully updated with modern finishes and timeless design, this kitchen is perfectly suited for everyday living and entertaining alike. The thoughtfully designed split-bedroom floor plan provides privacy for everyone. The spacious primary suite serves as a true retreat, featuring a luxurious ensuite bath complete with dual vanities, a relaxing soaking tub, a separate walk-in shower, and a private water closet. Generous closet space and a serene atmosphere make this the perfect place to unwind at the end of the day. Two additional bedrooms are well-sized with built in storage window seats, and separated by a unique jack-and-jill bathroom with dual vanities, creating an ideal layout for families and guests. The fourth bedroom with closet makes a great added space to the home. A third full bathroom conveniently provides supplemental access to the backyard oasis where a heated self-cleaning swimming pool, covered lanai, and fully fenced yard create the ultimate setting for year-round entertainment. Residents of this sought-after gated community enjoy access to outstanding amenities including a clubhouse, community pool, playground, private boat ramp, and dock, providing endless opportunities for recreation and enjoyment. Easy access to get to Bartow and the Polk Parkway With a new roof in 2021, this beautifully updated, meticulously maintained, and ideally located home offers the perfect combination of luxury, comfort, and Florida living.

472 Archaic Drive, Winter Haven

1394 Oakmont Drive, Winter Haven
$535,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 2 SubDv. ⋅ 33884 Zip Code
Experience resort-style living in the highly sought-after gated 55+ golf community of Lake Ashton, offering 24-hour security and an incredible amenity-rich lifestyle. Residents enjoy access to championship golf courses, multiple clubhouses, indoor and outdoor pools, fitness centers, tennis and pickleball courts, bowling, movie theater, restaurant and lounge areas, walking and biking paths, lake access, and a vibrant social atmosphere that makes Lake Ashton one of Central Florida’s premier active adult communities. This beautifully upgraded Ashton floor plan offers approximately 2,606 square feet of living space with 3 bedrooms, 2 full bathrooms, a den, flex room, and a spacious 2-car plus golf cart garage with room for up to 2 golf carts. Inside, you’ll find soaring cathedral ceilings, tray ceiling accents, crown molding, recessed lighting, updated fixtures, and a seamless blend of laminate flooring and ceramic tile throughout. The gourmet kitchen features granite countertops, solid wood 42-inch cabinetry with crown molding, stainless steel appliances including a Bosch dishwasher and double convection ovens, along with abundant prep and storage space. Designed for both comfort and efficiency, the home includes a FULLY PAID OFF SOLAR PANEL SYSTEM with transferable warranty, whole-house generator, enhanced landscaping, updated irrigation system, abundant storage, and negotiable furnishings for a potential move-in-ready opportunity. The spacious primary suite offers custom closets, soaking tub, oversized walk-in shower, and private sauna. Enjoy Florida living year-round from the oversized screened lanai complete with remote-control privacy shades, outdoor kitchen with stainless steel grill, kegerator, wine fridge, barbecue area, and an impressive Veranda 10-person hybrid swim spa. The SELLER IS ALSO INCLUDING THE GOLF CART WITH THE SALE, making it even easier to enjoy everything the Lake Ashton lifestyle has to offer.

1394 Oakmont Drive, Winter Haven

6710 Winterset Gardens Road, Winter Haven
$530,000
4 Beds ⋅ 3 Baths ⋅ Winterset Gardens SubDv. ⋅ 33884 Zip Code
CUSTOM BUILT POOL HOME IN WINTERSET GARDENS WITH CHAIN OF LAKES ACCESS. Welcome to this beautifully maintained, one-owner custom home located in desirable, lake front Winterset Gardens. This spacious 4-bedroom, 3-bath residence is directly across the street from little Lake Winterset and features 10 foot ceilings, 8 foot custom doors and two true master suites (One with attached pool bathroom), each with walk-in closets, offering flexible living for multi-generational families or guests. Built with quality and efficiency in mind, the home includes a 45-year architectural shingle roof, foam-filled concrete exterior walls, and extra attic insulation. Inside, you’ll find wood plank tile flooring throughout, Level 3 granite surfaces, and semi-custom solid wood cabinetry with dovetail soft-close drawers in the kitchen, bathrooms, and spacious indoor laundry room. The kitchen is equipped with matching LG appliances, under-cabinet lighting, and a Delta touch faucet. Custom craftsmanship is showcased throughout with professionally trimmed 8ft. doors and windows, shiplap accent walls in the dining area, kitchen, and island, plus a stunning custom electric fireplace with mantel, hearth, and barn door cabinetry in the living room. The primary suite also features a matching custom shiplap electric fireplace for added comfort and style. Step outside to your fully fenced private backyard retreat featuring a saltwater pool with a variable speed pump, paver deck and pre-installed footers for a future pool enclosure. The covered lanai is designed for entertaining with an outdoor kitchen including grill, refrigerator, storage, and matching Level 3 granite. Enjoy the motorized screen, tongue and groove wood ceilings, and ambient lighting for the perfect indoor-outdoor experience. Additional highlights include Permanent app-controlled exterior lighting, Sprinkler system on well, leased water filtration and softener, Triple sliding glass doors that retract to fully open to the patio to the living area, Pre-wired surround sound system in living room, primary bedroom, and patio, Upgraded DC motor ceiling fans throughout, Tiled showers to the ceiling with rain shower in primary bath, Framed bathroom mirrors and comfort-height elongated toilets, Custom garage cabinetry, sealed floors, and hot/cold water hookup. Winterset Gardens is a highly respected, quaint neighborhood on the shore of Little lake Winterset and offers an optional $100 HOA with a community boat ramp and no deed restrictions allowing direct access to The world renowned Winter Haven Chain of Lakes. 24 canal connected lakes offering great fishing, skiing and leisure boating. Hop on your boat from your neighborhood and go get a bite to eat at several float up bars and restaurants. This home combines thoughtful and impressive upgrades, energy efficiency, and custom design in a highly sought-after location. Truly move-in ready and built to impress.

6710 Winterset Gardens Road, Winter Haven

21 Lake Avenue, Winter Haven
$525,000
3 Beds ⋅ 3 Baths ⋅ Aqualane Heights SubDv. ⋅ 33880 Zip Code
SELLER IS MOTIVATED AND SAYS BRING OFFERS! Wake up to the kind of sunrise most people only see on vacation. This fully renovated 3-bedroom, 3-bath lakefront home sits on an expansive lot along the pristine shores of Eagle Lake, offering the perfect mix of comfort, privacy, and natural beauty. Inside, the open, sun-filled floor plan was designed to capture panoramic water views from nearly every angle. Natural light pours in, highlighting the modern finishes and thoughtful updates throughout. This home is completely move-in ready! The primary suite is a true retreat. Imagine waking up to unobstructed lake views, then stepping into a spa-inspired en-suite bath featuring a freestanding soaking tub, custom tile shower, and high-end finishes that feel straight out of a luxury resort. It’s a space designed to help you unwind. Two additional bedrooms and bathrooms offer plenty of room for family and guests. The expansive family room creates an ideal gathering space for holidays, game nights, or relaxed weekends by the water. Step outside and the lifestyle really begins. The oversized lot provides space to spread out, whether you envision lakeside games, a garden, a pool or simply quiet evenings under the sky. A large open patio overlooks the peaceful shoreline, perfect for morning coffee at sunrise or dinner as the light reflects off the water. With your private, brand new dock you can swim, boat, fish, or kayak straight from your backyard. Eagle Lake becomes part of your everyday life. Located in a quiet neighborhood with no HOA and no thru streets, you’ll enjoy rare lakefront privacy and peace. This is lakeside living at its best. Updated, turnkey, and ready for new owners

21 Lake Avenue, Winter Haven

1301 Hidden Creek Court, Winter Haven
$525,000
3 Beds ⋅ 2 Baths ⋅ Grey Fox Hollow Ph 02 SubDv. ⋅ 33880 Zip Code
Welcome to 1301 Hidden Creek Ct in Winter Haven, FL—a charming retreat that perfectly blends modern amenities with serene country living, all without the constraints of an HOA. This home offers the tranquility of rural life while maintaining easy access to modern conveniences. At the heart of this single-story home is an open-concept layout that seamlessly connects the living room, dining area, and kitchen—perfect for both entertaining and daily life. The kitchen is equipped with modern appliances, ample cabinetry, and stylish countertops, complemented by durable vinyl plank flooring that extends throughout the home. This residence includes three well-appointed bedrooms, including a master suite that ensures comfort with its ensuite bathroom featuring a walk-in shower and ample closet space. The two additional bedrooms provide comfortable accommodations for family or guests, supported by a full secondary bathroom. Significant updates have been made to enhance comfort and functionality, including a freshly painted exterior, new landscaping, and an updated irrigation system. Practical additions such as a new pool pump, pool screen, hot water heater, and custom window treatments, including shades and shutters, make this home a standout choice. The expansive front porch and oversized screened lanai offering delightful outdoor living spaces that overlook the large fenced-in backyard with views of a vast cow pasture, offering a glimpse into pastoral tranquility. A detached garage, which can also serve as a workshop or gym, adds to the home’s appeal, alongside a side-load two-car garage with plenty of driveway space for additional parking and storage. This property is thoughtfully prepared to provide its new owners with a peaceful yet refined lifestyle, ideal for hosting gatherings or enjoying a quiet evening in a picturesque country setting.

1301 Hidden Creek Court, Winter Haven

1872 Eloise Cove Drive, Winter Haven
$525,000
4 Beds ⋅ 4 Baths ⋅ Eloise Cove SubDv. ⋅ 33884 Zip Code
Prepare to be impressed with this stunning home in the amazing Eloise Cove Community! Discover your dream home in the highly sought-after, gated lakefront community. This spacious 4-bedroom, 3.5-bathroom, 3-car garage offers 3,716 square feet of beautifully designed living space, perfect for both relaxation and entertaining. As you arrive, the mature, well-manicured landscaping and expansive brick paver driveway set the tone for this elegant home. Step inside to be greeted by soaring ceilings, the dining space, beautiful trim work, and an open-concept floor plan. You will LOVE the luxurious downstairs primary bedroom with a tray ceiling and room for a sitting area, and an oversized walk-in closet. The primary bathroom is a spa-like retreat with dual vanities, a walk-in shower, and a soaking tub. Perfect for the chef in the family, the kitchen offers 42-inch glazed maple cabinets, granite countertops, a spacious island, stainless steel appliances (including a double oven), and a breakfast nook. Also located downstairs is an office at the entrance that doubles as an optional fifth bedroom. The great room flows seamlessly to a screened back porch, which opens to the incredible fenced backyard with pavered patio shaded by lovely oak trees, providing the ultimate space to unwind. Upstairs you will find a generous bonus room perfect for a media space or playroom, three large bedrooms, a full bath, and a Jack-and-Jill bathroom. Eloise Cove is a tranquil community offering residents access to a private dock on Lake Eloise, part of the Winter Haven Chain of Lakes. The location provides the perfect blend of serene lakeside living and modern convenience, with shopping, schools, medical facilities, and Legoland just minutes away. This home offers the ultimate Florida lifestyle. Don’t miss the opportunity to own this exceptional home in this impressive community. The seller is offering the fitness equipment inside the home and the outdoor items for sale under separate agreement. A complete list can be provided to anyone who is interested in these items. Ages of roof (7 years), HVAC (4 years), and Hot Water Heater (1 year).

1872 Eloise Cove Drive, Winter Haven

2409 Berkshire Drive, Winter Haven
$520,000
4 Beds ⋅ 3 Baths ⋅ Eloise Pointe Estates Pb 72 Pgs 4&5 SubDv. ⋅ 33884 Zip Code
One or more photo(s) has been virtually staged. Don't miss out on this opportunity to own this beautiful home that in 1990 was an AWARD winner in the Polk County Builders Association Parade of Homes and built by local custom home builder Gordon Collins. Upon walking up the home your greeted with a very welcoming courtyard. This home has had some updates. The appliances in the kitchen are all updated Frigidaire Gallery Series. The roof was replaced in 2024. The pool/spa was resurfaced in 2023 and also comes with a 10 year warranty. The home features a split bedroom plan and a large open concept great room area, perfect for entertaining. Around the property is beautiful foliage providing privacy. Having a side load 3-car garage with high ceilings is also a bonus. Gorgeous views from inside of the home can be had from several vantage points. Beautiful natural lighting are also assets of the home. Perfect set-up for adding an an ourtdoor kitchen on the covered lanai/ pool area. Some of the furnishings will be included with this property. There is also a central vacuum system throughout. This beautiful home in this desirable sought after neighborhood will not last long at this price.

2409 Berkshire Drive, Winter Haven

651 Hart Lake Drive, Winter Haven
$515,000
4 Beds ⋅ 3 Baths ⋅ Hart Lake Hills Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully maintained 4-bedroom, 3-bath pool home located in the highly sought-after gated community of Hart Lake Hills. Offering the perfect blend of comfort, efficiency, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining.Step inside to an open and inviting floor plan featuring a spacious kitchen with stainless steel appliances, a gas range, abundant cabinetry, and plenty of counter space overlooking the main living areas. The generous primary suite provides a relaxing retreat with a well-appointed ensuite bath, while the split-bedroom layout offers added privacy for family and guests. Outside, enjoy the screen-enclosed saltwater pool and expansive lanai overlooking the large, fully fenced backyard. The outdoor space has also been thoughtfully updated with pavers installed on the back deck in 2019, the pool remarcited in 2019, and a new pool pump and salt cells added in 2024. Additional updates and features include a roof installed in 2017, A/C installed in 2019, fresh interior paint in 2020, a whole-home Generac generator, gas hot water heater, and solar panels for added energy efficiency and peace of mind. Perfectly situated near schools, shopping, dining, LEGOLAND Florida Resort, and Highway 27, this home offers convenient access to everything Central Florida has to give while tucked away in one of the area's desirable gated communities. Schedule your private showing today! Solar panel loan must be assumed by buyer.

651 Hart Lake Drive, Winter Haven

2664 Country Club Road N, Winter Haven
$515,000
4 Beds ⋅ 3 Baths ⋅ Poinsettia Park SubDv. ⋅ 33881 Zip Code
One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4 bedroom, 3 bathroom pool home featuring a 3-car garage and situated on over half an acre. This expansive property offers a massive driveway, providing exceptional space for a boat, RV, or simply added privacy between neighbors—an increasingly rare find. Step inside to an inviting layout enhanced by luxury vinyl plank flooring and tile throughout. The home features a spacious front sitting room and an open-concept design that seamlessly connects the main living areas. At the heart of the home is the upgraded kitchen, complete with granite countertops, stainless-steel appliances, ample cabinetry, generous counter space, and a large island overlooking the bright and open living room—ideal for gatherings and everyday living. The primary suite offers a peaceful retreat with an ensuite bathroom featuring dual vanities, a garden tub, walk-in shower, and a walk-in closet. French doors from the primary bedroom lead directly to the screened-in patio, creating a private connection to the outdoor oasis. The additional bedrooms are located on the opposite side of the home, equal in size and conveniently positioned near two full guest bathrooms. Step outside to enjoy true Florida living on your large screened-in pavered patio overlooking the inground pool, perfect for entertaining family and friends. The property also includes a storage shed for added convenience. Recent upgrades include interior and exterior paint (2026), a new metal roof (2025), and new pool screens, offering peace of mind and move-in readiness. Located near a variety of restaurants, retailers, and everyday conveniences, this home combines space, privacy, and modern comfort in a highly desirable setting.

2664 Country Club Road N, Winter Haven

952 N Heron Circle, Winter Haven
$515,000
4 Beds ⋅ 3 Baths ⋅ Garden Grove South Add SubDv. ⋅ 33884 Zip Code
Welcome to your own slice of lakefront paradise on the serene shores of Ned Lake in Winter Haven, Florida. From the moment you step inside, you’re greeted by sweeping water views that set the tone for a relaxed yet refined lifestyle. Designed for both comfort and entertaining, this spacious home offers open living areas that flow seamlessly toward the sparkling pool and outdoor deck overlooking the lake. Enjoy morning coffee as the sun rises or gather with friends for sunset views that never get old. The kitchen features ample counter space, stainless steel appliances, and a functional layout ideal for daily living or hosting. Vaulted ceilings add architectural charm throughout, while the wood-burning brick fireplace creates a cozy focal point for cooler evenings. A screened room extends your living space outdoors, and the split floor plan ensures privacy for every bedroom, all generous in size and filled with natural light. Step outside to your private boat dock, where fishing, kayaking, or a peaceful boat ride await. Ned Lake is surrounded by residential homes and the scenic Street Nature Center to the east, with a small public park and boat ramp on the northwest side—perfect for guests or weekend outings. Conveniently located near Legoland, shopping, dining, and medical facilities, this home offers the perfect balance of tranquility and accessibility. With its beautiful setting, outdoor amenities, and endless views, this is truly a place where lake living dreams come to life.

952 N Heron Circle, Winter Haven

3205 La Salle Street, Winter Haven
$510,000
5 Beds ⋅ 4 Baths ⋅ Orleans SubDv. ⋅ 33884 Zip Code
Welcome to 3205 La Salle Street, where resort-style outdoor living, an exceptional floor plan, and modern elegance come together in the highly sought-after Orleans community. Built in 2023 by Ryan Homes, this beautifully upgraded Lynn Haven model offers 5 bedrooms, 4 full bathrooms, and 3,021 square feet of thoughtfully designed living space that perfectly balances everyday comfort with effortless entertaining. Situated on a beautifully landscaped corner lot featuring a paver driveway, lush tropical landscaping, and extra green space beyond the backyard, this property offers a setting rarely found in newer construction. The fully privacy-fenced backyard is your own private retreat, complete with a newly added saltwater pool, expansive covered lanai, and additional green space beyond the pool that enhances both privacy and the feeling of having an even larger backyard—perfect for entertaining, pets, or simply enjoying peaceful Florida evenings. Nestled between Lake Eloise and Lake Winterset within the intimate Orleans community of just 42 homesites, residents enjoy low HOA dues, no CDD fees, and select community canal access to Lake Eloise while being less than two miles from Publix, Starbucks, LEGOLAND, shopping, dining, and everyday conveniences. Inside, abundant natural light, soaring ceilings, and an open-concept design create a welcoming atmosphere from the moment you enter. A spacious flex room off the foyer offers endless possibilities as a formal dining room, home office, playroom, or additional living space. The expansive great room seamlessly connects to the chef-inspired kitchen, complete with quartz countertops, stainless steel appliances, a large center island, abundant cabinetry, and a walk-in pantry, creating the ideal gathering space for family and friends. One of this home's standout features is its exceptionally functional floor plan. The first-floor bedroom and adjacent full bathroom provide the perfect private space for guests or multigenerational living. Upstairs, the luxurious primary suite serves as a true retreat with two walk-in closets and a spa-inspired ensuite featuring dual vanities, a walk-in shower with a Roman-style seat, and a private water closet. A secondary upstairs bedroom enjoys the privacy of its own ensuite bathroom, while two additional generously sized bedrooms share a well-appointed guest bath. Completing the second level is an oversized loft, offering endless flexibility as a media room, game room, second family room, or homework space, along with a conveniently located upstairs laundry room. Better than new, this home has already been enhanced with thousands of dollars in premium upgrades, including a saltwater pool, irrigation well, generator-ready wiring, EV charging system wiring, an Ecobee smart thermostat, WiFi-enabled garage door opener, and energy-efficient construction throughout. The roof, HVAC system, water heater, and major kitchen appliances are all approximately two to three years old, providing added peace of mind for years to come. Offering an exceptional combination of luxury, functionality, outdoor living, and one of Winter Haven's most convenient locations, 3205 La Salle Street is truly better than new and ready to welcome its next owners.

3205 La Salle Street, Winter Haven

700 Avenue B  Sw, Winter Haven
$510,000
Linger & Nichols Sub SubDv. ⋅ 33880 Zip Code
Prime mixed-use commercial property just minutes from the vibrant and growing Downtown Winter Haven. Move-in ready and zoned RP (Residential-Professional), this property offers exceptional flexibility for professional offices, medical or wellness practices, studios, or light retail. Features include two private offices, three large open work areas, a break room with full kitchen, three restrooms, and ample storage. Accessibility features throughout. On-site parking for at least 14 vehicles and existing signage for excellent visibility. Located just minutes from Downtown Winter Haven, major hospitals, dining, and major roadways. Property falls inside the Winter Haven CRA district boundaries. Don’t miss this chance to own in one of Central Florida’s fastest-growing markets!

700 Avenue B Sw, Winter Haven

1016 Biltmore Drive Nw, Winter Haven
$510,000
4 Beds ⋅ 2 Baths ⋅ Biltmore Shores SubDv. ⋅ 33881 Zip Code
NEW POOL PUMP, NEW H20 HEATER - TWO 30AMP. RV HOOKUPS - HOME WARRANTY AVAILABLE! Perfectly Positioned for Lakeside Potential Priced to reflect opportunity, this expansive lakeside home offers the ideal canvas to create your dream waterfront retreat. With soaring wood-beam ceilings, walls of glass, and panoramic lake views, the space delivers unmatched volume, light, and indoor-outdoor flow. A flexible floor plan easily accommodates a stunning family living area, game room, and entertainment spaces—perfect for hosting or relaxed lake life. Enjoy direct access to the water, poolside living, and endless potential to personalize finishes and style to your taste. Homes with this setting, scale, and view are rare—this is your chance to unlock value and design equity in a premier lakeside location. Lake Jessie connects to 22 navigable lakes on the Winter Haven Chain, giving you endless days of boating, fishing, watersports, and dock-and-dine options across town. Aviation and adventure lovers will especially appreciate being on the same lake as Jack Brown’s Seaplane Base & School, a beloved Winter Haven landmark—watch the splash-and-goes from your backyard or take a lesson and see the Chain from the sky. If you’ve been waiting for a true lakefront lifestyle with huge potential on the Chain, 1016 Biltmore delivers the view, the water access, and the room to make it your own. Schedule your showing and come see the possibilities.

1016 Biltmore Drive Nw, Winter Haven

20 Brevard Drive Se, Winter Haven
$506,000
4 Beds ⋅ 4 Baths ⋅ Eloise Woods Lake Mariam Unit SubDv. ⋅ 33884 Zip Code
Private tri-level pool home on a quiet dead-end street—just minutes from the Winter Haven Chain of Lakes and LEGOLAND® Florida Resort. This 4-bedroom, 3.5-bath home is designed for flexibility, privacy, and real Florida living. Situated at the end of a street with no drive-by traffic, this property offers a peaceful setting that’s hard to come by—perfect for those who value space and quiet. One of the biggest advantages here is the tri-level layout, featuring a separate downstairs bedroom and full bathroom—ideal for guests, multi-generational living, or even a private office setup with its own space away from the main living areas. Out back, you’ll find a screen-enclosed pool and expansive patio, built for year-round enjoyment and entertaining. The large, fully fenced yard adds another layer of privacy and gives you room to spread out without feeling boxed in. And here’s where this one separates itself—there’s plenty of room for RV or boat parking with coverage, making it a rare find for buyers needing space for larger vehicles or recreational toys. Inside, the home offers a comfortable flow with multiple living areas, a spacious primary suite, and well-sized secondary bedrooms—giving everyone their own space while still feeling connected. Highlights: 4 Bedrooms | 3.5 Bathrooms Tri-level layout with private downstairs bedroom & full bath Dead-end street – no through traffic Screen-enclosed pool with large outdoor living area Fully fenced yard with strong privacy Covered parking for RV, boat, or extra vehicles Close to Chain of Lakes, boat ramps, and LEGOLAND® If you’re looking for a home that offers privacy, flexibility, and outdoor living—while still being close to everything—this one delivers. Call for your very own private showing today!

20 Brevard Drive Se, Winter Haven

406 Terranova Street, Winter Haven
$500,000
4 Beds ⋅ 3 Baths ⋅ Terranova Phase Iii SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully updated Cassidy-built 4-bedroom, 3-bath pool home in the highly desirable Terranova community of Winter Haven. Pride of ownership is evident throughout this move-in ready residence, where nearly every major component has been updated since 2022. The stunning kitchen was completely renovated with new cabinetry, tile backsplash, Cambria countertops, new sinks, updated fixtures, and all new appliances. Matching Cambria Quartz Kitchen & Master bathroom countertops, guest bathrooms and laundry room, complemented by updated faucets, sinks, and lighting throughout the home. Additional improvements include a new roof (11/2022), new A/C system (2023), new water heater (2024), new bedroom carpeting (2022), new blinds throughout (2022), complete interior and exterior painting (2022), plywood attic flooring for added storage (2023), new garage cabinets, laundry room cabinets, and additional cabinetry in the primary and pool bathrooms. Outdoor living is equally impressive with a screened and heated saltwater pool that underwent extensive remodeling in 2022, including an exposed aggregate finish, new ANSI-certified main drain covers, updated fittings and lighting, a new pool pump (2022), a new pool heater (2023), and a new screen enclosure (2022). Porcelain tile flooring enhances the main living areas, while the open floor plan, high ceilings, and spacious layout make this home perfect for everyday living and entertaining. One of the home's standout features is the private fourth bedroom and third bathroom, which are separated by a sliding door, creating an ideal in-law suite, guest retreat, or private space for multi-generational living. Private gated entrance to Chain of Lakes Elementary for neighborhood access only. Conveniently located near shopping, restaurants, medical facilities, LEGOLAND, and Winter Haven's Chain of Lakes, this exceptional property offers the peace of mind that comes from knowing the expensive updates have already been completed. Don't miss the opportunity to own one of Terranova's finest homes.

406 Terranova Street, Winter Haven

3023 Saint Paul Drive, Winter Haven
$500,000
8 Beds ⋅ 4 Baths ⋅ Winter Lake Manor SubDv. ⋅ 33880 Zip Code
BUYER FINANCING FELL THROUGH!! Don’t miss your chance to own this fully rented quadplex offering immediate cash flow. All four units are currently occupied with month-to-month tenancies paying $1000-1200 per month, giving a new owner flexibility to increase rents to market value or renovate units for added equity and higher returns. Each unit features: 2 Bedrooms / 1 Bathroom, spacious living and dining room combination, dedicated laundry room with washer/dryer hookups, gas stoves and hot water heaters. The roof is only 5 years old. Whether you’re looking to expand your portfolio or secure a strong income-producing property, this quadplex checks all the boxes with built-in upside potential.

3023 Saint Paul Drive, Winter Haven

1930 Austin Terrace, Winter Haven
$499,900
4 Beds ⋅ 3 Baths ⋅ Woodpointe Ph 1 SubDv. ⋅ 33884 Zip Code
Welcome to 1930 Austin Terrace, located in the highly desirable gated community of Woodpointe in SE Winter Haven. Perfectly situated near Hwy 27 and just minutes from LEGOLAND Florida Resort, this home offers both convenience and a peaceful cul-de-sac setting on a spacious fully fenced 0.32-acre lot.This beautifully designed 4-bedroom, 3-bathroom POOL home welcomes you with an elegant entry foyer, soaring specialty ceilings, and wood flooring throughout, complemented by ceramic tile in the foyer, kitchen, breakfast nook, and bathrooms. The thoughtfully designed layout includes a formal dining room and an open, inviting living space ideal for both everyday living and entertaining. The kitchen features granite countertops, a new refrigerator (04/2026), a breakfast bar, and a walk-in pantry, with a cozy breakfast nook overlooking the saltwater pool for relaxed mornings. Step outside to enjoy true Florida living with a screen-enclosed pool, covered lanai, and a beautifully paved pool patio, perfect for hosting or unwinding in your private, fully fenced backyard. The pool system has been well maintained with a new pool pump (09/2025) and recently updated salt cell and WiFi-enabled motherboard (03/2026), offering modern convenience and efficiency. The spacious primary suite serves as a private retreat, complete with an additional office space, fireplace, walk-in closet, and an ensuite bathroom featuring a split sink vanity, garden tub, and separate shower. Additional highlights include a newer AC system (approximately 4 years old), a brick-paved driveway and walkways, and a charming covered front porch accented by columns, adding to the home’s curb appeal. A brand new roof will be put on before closing! This exceptional property offers the perfect combination of space, style, and location in one of SE Winter Haven’s most sought-after gated communities.

1930 Austin Terrace, Winter Haven

503 Hamilton Shores Court Ne, Winter Haven
$495,000
3 Beds ⋅ 3 Baths ⋅ Hamilton Pointe SubDv. ⋅ 33881 Zip Code
WELCOME TO THIS AMAZING POOL HOME SITUATED ON AN OVERSIZED (.43) ACRE LOT LOCATED IN HAMILTON POINTE, AN ESTALISHED LAKEFRONT COMMUNITY IN WINTER HAVEN, FL! As you enter, you will immediately notice the NATURAL LIGHT, HIGH CEILINGS, OPEN CONCEPT FLOORPLAN and BEAUTIFUL POOL VIEW. The spacious eat-in kitchen features lots of built-in cabinetry, granite countertops, stone backsplash, double ovens, island with cooktop, large double sink and another great view of the pool area! The primary en-suite has an oversized soaking tub for relaxing, double sinks, large walk-in-shower with built-in-seating, 2 huge walk-in closets with custom shelving, and plantation shutters. The 2 additional bedrooms are very spacious and feature built-in closet shelving. The second full bath has been tastefully updated with granite countertops, canned lighting and large walk-in shower with corner seating. The oversized and fully screened pool and patio area is perfect for all your entertaining! Thanks to the solar/electric heated pool, you will be able to enjoy swimming year-round. The 1/2 bath is conveniently located just in from the screened lanai, making it convenient for guests. Don't forget about the spacious 3 car (25 x 35) garage and circle drive for visitor parking. The inside laundry room has cabinetry for extra storage and also features a utility sink. Save $$ on your water bill with your very own irrigation well. A newer hot water heater installed (2024) will also add to the home's efficiency. Don't miss out on this meticulously maintained property centrally located between Tampa International and Orlando International Airport! The Country Club of Winter Haven, shopping, medical and LEGOLAND, FL are just minutes from this wonderful property that has been lovingly cared for.

503 Hamilton Shores Court Ne, Winter Haven

1988 Crossroads Boulevard, Winter Haven
$495,000
4 Beds ⋅ 3 Baths ⋅ Crossroads/Lk Region SubDv. ⋅ 33881 Zip Code
This Beautiful 4-bedroom,3-bath home with additional office offers the perfect blend of style and comfort. Featuring hardwood floors and tile throughout the main living areas, cozy carpeted bedrooms, and an open floor plan with high ceilings that fill the home with natural light. The kitchen boasts elegant granite countertops, while the renovated master bathroom showcase a huge glass shower, double vanity sinks and solid surface countertops. Step outside to your backyard oasis with a gorgeous Pool and Jacuzzi, complete with stone Pebble Tec finish - perfect for relaxing or entertaining. Outside also includes a well for lawn watering & landscape lighting. Enjoy the added bonus of a community pool and clubhouse. Conveniently located near downtown Winter Haven with easy access to Tampa and Orlando, this home truly has it all. Call today for your private showing!!!

1988 Crossroads Boulevard, Winter Haven

2405 Melrose Street, Winter Haven
$495,000
4 Beds ⋅ 2 Baths ⋅ Crossroads At Lake Region SubDv. ⋅ 33881 Zip Code
Welcome to this stunning 4-bedroom, 2-bath pool home that blends elegance, comfort, and functionality. From the moment you enter through the double doors, you’re greeted with an open floor plan and wood plank laminate flooring throughout, creating a warm and inviting atmosphere. The home features multiple living and dining spaces, including a formal living room, formal dining room (or office/den), a bright nook, and a spacious family room, offering plenty of room for entertaining and everyday living. The chef-inspired kitchen is a true showstopper, featuring state-of-the-art appliances, granite countertops, a large island with farmhouse sink, stovetop cooking area with vent, and a walk-in pantry. You’ll also love the coffee bar and abundance of counter and cabinet space—perfect for gatherings. The luxurious master suite boasts cathedral ceilings, crown molding, and a walk-in closet with custom built-in cabinetry. The spa-like master bath offers dual sinks, a garden tub, walk-in shower, linen closet, and private water area. The split floor plan places the additional bedrooms on the opposite side, each with high ceilings, crown molding, and spacious closets. A beautifully upgraded second bath with tiled walk-in shower serves bedrooms two and three, while the fourth bedroom—located just off the pool area—offers a peaceful view of the backyard. Step outside through the sliding glass doors to your own private paradise. The screen-enclosed chlorine pool with a covered lanai is perfect for relaxing, entertaining, or grilling out. The vinyl-fenced yard ensures privacy, and you’ll love the variety of fruit trees including banana, cherry, peach, lemon, and fig. Additional highlights include: upgraded light fixtures throughout, a spacious laundry room, and thoughtful details that make this home move-in ready. This home truly has it all—style, space, and a backyard oasis. Don’t miss your chance to own it!

2405 Melrose Street, Winter Haven

413 Horseshoe Lane Ne, Winter Haven
$495,000
4 Beds ⋅ 2 Baths ⋅ Hamilton Pointe SubDv. ⋅ 33881 Zip Code
Welcome to this beautifully crafted 4-bedroom, 2-bathroom custom home, ideally situated on an oversized lot in the sought-after Hamilton Pointe community of Winter Haven. From the moment you arrive, the long, wide driveway and side-entry garage set the tone for the space and elegance that await inside. Step through the front door into a bright and open floor plan, perfect for modern living. The spacious living room features a cozy fireplace and large sliding glass doors that seamlessly extend your living space into the backyard—ideal for both relaxing and entertaining. The kitchen is a chef’s delight with ample light cabinetry, stainless steel appliances, a breakfast bar, and a charming kitchen nook. The open-concept design creates a natural flow between kitchen, dining, and living areas—perfect for gatherings. Retreat to the expansive owner’s suite, complete with private glass doors to the backyard, a spa-like bathroom featuring a garden tub, separate shower, dual vanities, and generous storage space. The additional bedrooms and guest bathroom are thoughtfully located on the opposite side of the home, offering privacy for family or guests. There is also a flex room that can be used as a home office, cozy den, or even a 4th bedroom to suit your needs. Outside, the oversized backyard is a true oasis, perfect for gardening and already home to a variety of imported tropical fruit trees that include mango, guanabana (soursop), guava and Rose Apple trees. A beautifully designed, functional shed enhances the property’s versatility, complemented by a finished 2-car garage with durable epoxy flooring and ample storage. This property with over 2.300 square feet of living space has almost $300,000 in renovations and enhancements with energy efficacy in mind and completed in the past couple of years such as whole-home generator, Hurricane-rated doors, New electrical panels, Wood flooring throughout, Custom PVC shutters, deep well, attic insulation, freshly painted inside and outside and so much more! Enjoy a prime location at Hamilton Pointe—just minutes from downtown Winter Haven and Highway 27, and only a short 15-minute drive to Legoland. Don't miss the opportunity to own this well-maintained, one-owner home near Lake Hamilton. Schedule your private showing today and make this exceptional property yours!

413 Horseshoe Lane Ne, Winter Haven

673 Hart Lake Drive, Winter Haven
$494,000
4 Beds ⋅ 3 Baths ⋅ Hart Lake Hills Ph 2 SubDv. ⋅ 33884 Zip Code
Stunning 4-Bedroom pool home on an oversized, fully-fenced lot in the highly sought-after gated SE Winter Haven community of Hart Lake Hills. Welcome to your dream home! This lovingly maintained 4-bedroom, 2.5-bath residence sits on a spacious near 1/3-acre fully fenced lot offering privacy, room to roam, and the perfect blend of comfort and style. Step inside through the covered front porch or pull into the over-sized garage with custom epoxy floor and be wowed by the soaring high ceilings, elegant 8-foot interior doors, and an open-concept floor plan designed for both everyday living and entertaining. Gorgeous arched windows create a dramatic curb appeal and flood the home with natural light. The heart of the home features a spacious living area that flows effortlessly into the dining nook and kitchen—complete with French doors that open to your own backyard oasis. Enjoy indoor-outdoor living with a screened-in pool area and new upgraded salt-water cell system (both updated in 2024), a covered patio, and lush green grass—ideal for entertaining, relaxing, or play. The huge master suite is a true retreat, offering a large walk-in closet, dual vanities, a soaking tub, private water closet, and plenty of space to unwind. For added peace of mind, a 24kW whole-home generator was added in 2023, with discerning new owners also being able to enjoy a newer roof and tankless natural gas water heater (2021). Residents of Hart Lake Hills also enjoy private access to Lake Hart, an exclusive area in the community to launch your kayak or paddle board, have a picnic with family, or just enjoy the beautiful scenery. Even better, this property could not be any more commutable-- minutes from Highway 27 AND Hwy 60 that will take you to 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 and Tampa International Airports, 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. This is more than a house—it’s truly a place you will love to call home.

673 Hart Lake Drive, Winter Haven

6265 Pinehurst Loop, Winter Haven
$490,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii North SubDv. ⋅ 33884 Zip Code
Built in 2021, this single-story home is located in the 55+ community of Lake Ashton and offers scenic golf course views. The open floor plan connects the living, kitchen, and family areas, ideal for everyday living and entertaining. The kitchen features two-tone cabinetry, stainless steel appliances, and an oversized wrap-around island with bar seating. High ceilings, luxury vinyl plank flooring, and natural light enhance the space. Enjoy outdoor living from the screened lanai overlooking the golf course. Additional features include an oversized laundry/utility room, energy-efficient windows, wired in generator hookup, golf-cart-friendly garage, and paver driveway. Lake Ashton offers golf, pool, fitness center, and resort-style amenities with convenient access to shopping, dining, and major roadways.

6265 Pinehurst Loop, Winter Haven

2501 Avenue G  Nw, Winter Haven
$490,000
Inwood SubDv. ⋅ 33880 Zip Code
Drive thru beverage depot for sale! This owner operated, turn-key business comes with a 1500 sq ft building plus a 40 ft storage container. It's situated on a .37 acre corner lot at the intersection of 25th Street NW & Avenue G NW (also known as CR 542), which has a high traffic flow! This established business is an excellent yet affordable investment opportunity that you won't want to miss out on. The property is designed for drive-thru service, making it a quick and convenient stop for customers. It includes multiple security cameras, ample storage, and plenty of space for all the refrigeration and shelving. All store inventory, from popular sodas and snacks to beer, wine, and more, will be included in the sale at the time of closing, allowing the new owner to immediately continue business as usual. There is an another external circular drive beside the building that could be modified into an exterior drive-thru for night time & there are apprx. 4 parking spaces & additional land for potential expansion, such as creating more parking or modifying the setup to fit another business concept. Though it’s best suited to remain a beverage depot, the corner-lot location and flexible layout mean a motivated buyer could adapt it for other uses. Secure your spot on this high-traffic corner and take advantage of an established business with room to grow.

2501 Avenue G Nw, Winter Haven

1936 Crossroads Boulevard, Winter Haven
$489,000
4 Beds ⋅ 3 Baths ⋅ Crossroads At Lake Region SubDv. ⋅ 33881 Zip Code
One or more photo(s) has been virtually staged. Welcome to 1936 Crossroads Blvd in the highly sought-after gated community of Crossroads at Lake Region. This exquisite entertainer’s paradise comes partially furnished, features a private screened pool and spa, upgraded finishes throughout, and a fully fenced backyard designed for relaxation and entertaining. This meticulously upgraded Rockingham II floor plan, built in 2018, offers nearly 2,500 square feet of thoughtfully designed living space with one of the most functional and desirable layouts in the community. The open-concept design provides a natural flow from the kitchen to the main living area with sweeping views of the covered lanai and pool enclosure, making the home ideal for both everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, pendant lighting, abundant cabinetry, and a large breakfast bar overlooking the main living area. Wood-look tile flooring throughout the main living areas adds durability while giving the home a clean, modern feel. The primary suite features an upgraded tray ceiling, abundant natural light, and a spacious walk-in closet with a custom California Closet system for added organization. The ensuite bath offers dual vanities, a soaking tub, and a separate glass-enclosed shower. Step outside to the true highlight of the home. The screened pool and spa area features an upgraded epoxy-coated deck that gives the outdoor space a clean, finished appearance while also being durable and easy to maintain. The fully fenced backyard provides privacy and security, while the covered lanai and extended deck space offer plenty of room for outdoor seating, grilling, and entertaining year-round. The property also features a dedicated irrigation well to help maintain the landscaping efficiently, thereby reducing water costs. The home is also equipped with a programmable permanent exterior lighting system, allowing for customizable accent lighting year-round. This incredible property is conveniently located near Highway 27 and the Polk Parkway, offering quick access to I-4, major metro areas, local theme parks and attractions, shopping, dining, and Florida’s beautiful beaches. Do not miss this incredible opportunity. Schedule your private showing today.

1936 Crossroads Boulevard, Winter Haven

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