Refine Search
Sort by
5661 Struthers Court, Winter Haven
$349,990
4 Beds ⋅ 2 Baths ⋅ Lake Fox Shores SubDv. ⋅ 33884 Zip Code
RARE DUPLEX OPPORTUNITY – PERFECT FOR INVESTORS OR HOUSE HACKING! Excellent opportunity to own a CBS duplex featuring two 2-bedroom, 1-bath units situated on approximately 0.22 acres, ideal for a buy-and-hold investor or an owner-occupant looking to offset their monthly mortgage with rental income. One unit is currently rented while the other is vacant, providing flexibility for immediate occupancy or the opportunity to place your own tenant. The property is in good working and living condition and features attractive curb appeal, open kitchens, spacious living areas, and generously sized bedrooms. Major improvements include a NEW ROOF installed in 2025 and A/C systems from 2025 and 2017, helping reduce concerns over major capital improvements. With one unit already producing income and the second available for occupancy or rental, this property offers multiple possibilities for both investors and owner-occupants. Live in one side and rent the other to help offset your mortgage or operate both units as a long-term rental investment. Duplex inventory at this price point is extremely limited. Don’t miss the opportunity to secure a versatile income-producing property with major updates already completed.

5661 Struthers Court, Winter Haven

3304 Costello Circle, Winter Haven
$299,900
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 4 SubDv. ⋅ 33884 Zip Code
Better than New and Move in ready! A screened porch for morning coffee, a fully fenced backyard, and a kitchen finished with white cabinetry and quartz countertops—3304 Costello Circle brings together the features that make a house comfortable to come home to. Set in Winter Haven’s Villamar community, this single-story block home was built in 2023 and offers three bedrooms, two full bathrooms, 1,553 square feet of living space, and an attached two-car garage. Inside, luxury vinyl plank flooring extends throughout the home, with no carpet to maintain. The open-concept living and dining areas keep the main gathering space connected to the kitchen, making it easy to prepare a meal while spending time with guests. White cabinets, quartz countertops, and ample workspace give the kitchen a clean, coordinated finish. The split-bedroom floor plan places the primary suite apart from the secondary bedrooms. The primary bedroom includes a generous walk-in closet and its own en suite bathroom. Two additional bedrooms share a hallway bathroom and provide space for guests, hobbies, or a home office. The second bedroom also includes a walk-in closet, adding storage beyond the primary suite. Indoor laundry keeps everyday tasks conveniently inside. Continue to the screened porch, where there is a welcoming spot to sip morning coffee or settle in for a quiet evening. The fully fenced backyard extends the outdoor living space with room to enjoy the sunshine, garden, or spend time with pets. Beyond your own backyard, Villamar offers a community swimming pool, cabana, shaded poolside seating, and playground in a lakeside setting along Crystal Lake. Shopping, dining, LEGOLAND Florida, and connections to US-27, US-17, and Highway 60 add to the location’s convenience. Come explore the layout, finishes, and outdoor spaces that make this Winter Haven home stand out.

3304 Costello Circle, Winter Haven

1321 Oakmont Drive, Winter Haven
$434,700
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
** CDD Debt Balance PAID IN FULL, saving you thousands! **A new four-season Sunroom was completed in April 2026. It is glass-enclosed with a separate HVAC mini-split and has beautiful new flooring. This home offers amazing curb appeal, with new landscaping on every side of the house, including lush privacy plantings in the back. The St. Marks floor plan has 3 Bedrooms and 2 Baths, plus a Den, spacious Laundry Room and a Double-car Garage with designated Golf Cart Entry. With 2,069 sq.ft. living area in the original house PLUS an additional 243 sq.ft. living area in the Sunroom, this OPEN and SPACIOUS home is ideal for entertaining friends and family. The tile plank flooring that appears "wood like" flows thru the LR, Formal Dining, Foyer, Kitchen, Dinette, Den, Sunroom and Laundry Rooms -- adding a touch of class to this truly charming home! The voluminous ceilings are enhanced with the 8ft. door openings in the home. The kitchen is enhanced with Granite countertops, soft close drawers and cabinets with newer hardware, stainless steel appliances, tiled backsplash, step-up breakfast bar with pendant lights, and abundant countertop space for food prep and display. The Dinette area, which is adjacent to the kitchen, is accessible from the Sunroom and the Den. The spacious Owners Suite occupies the left wing of the home and is a private retreat featuring His/Her walk-in closets and its very own En-Suite bath area. The Primary Bath offers His/Her comfort height vanities with Granite countertop and Newer Cabinet Hardware, a Walk-in shower w/glass door enclosure and Large soaking tub. The triple glass block allows an abundance of natural light into the space. A "Barn-Like" door on a smooth track system separates the Primary Suite from the Primary Bath. It's stylish and practical. On the right side of this Split Floor Plan home are Bedrooms 2 and 3 and the Guest Bath. The Guest Bath has a comfort height vanity, Shower/tub combo and Newer Hardware on the Cabs. It's perfectly positioned between the Guest Bedrooms. The laundry room is well designed and is the passage from the garage into the home. The laundry room has additional shelving for your storage needs. Hosting a Game Night or Want to Cozy Up with a Good Book? The brand-new SUNROOM would be the ideal place! It's accessible thru the TRIPLE SLIDERS in the LR & DOUBLE SLIDERS in the Dinette. ADDITIONAL UPGRADES: Whole House Gutter System, Automatic Screen (Skeeter Beeter) on the Garage Door, Storm Door on the front door, Pull Down Attic Ladder, new window dressings throughout the home, Six-Filter Reverse Osmosis Water System added to the Kitchen sink, Updated Painting in Several Rooms and Cabinet Handles in the Kitchen and Bathrooms. Lake Ashton has (2) clubhouses, (2) Golf Courses, Planned Activities and Resort Style Amenities. Residents enjoy 2 Swimming Pools (one Indoor & one Outdoor), Movie Theater, Bowling Lanes, Card, Craft and Billiard Rooms, Fitness Rooms, Media Rooms, Indoor Racquetball, Indoor 1/2 Court Basketball, Pickle Ball Courts, Tennis Courts, Shuffleboard Courts, Eagles Nest (an Eatery), a Pro Shop and MORE! Lake Ashton is a beautiful 55 Plus Community in Florida closely located to Shopping, Restaurants, Entertainment and Medical Facilities. MAKE AN APPOINTMENT TODAY TOUR THIS BEAUTIFUL HOME.

1321 Oakmont Drive, Winter Haven

2900 Crump Road, Winter Haven
$425,000
4 Beds ⋅ 3 Baths ⋅ Magnolia Shores SubDv. ⋅ 33881 Zip Code
RARE LAKEFRONT OPPORTUNITY on beautiful Lake Hamilton, part of the northern CHAIN OF LAKES! Situated on an expansive .73-ACRE LOT with approximately 100 FEET OF DIRECT LAKE FRONTAGE, this well-built 4-bedroom, 2.5-bath POOL HOME offers an incredible waterfront setting, NO HOA, plenty of space and endless potential to create your own Florida retreat. A LARGE DRIVEWAY and OVERSIZED PARKING AREA provide plenty of room for multiple vehicles, guests, a boat or other recreational toys, while the DETACHED GARAGE offers even more parking, storage or workshop possibilities. Inside, the spacious living room features VAULTED CEILINGS accented by charming WOOD BEAMS, adding warmth and character to the home. The kitchen offers CORIAN COUNTERTOPS, plenty of cabinetry and stainless-steel appliances, including the STOVE, MICROWAVE and DISHWASHER. Throughout the home, you'll appreciate the abundance of STORAGE and ADDITIONAL CLOSET SPACE. The primary bathroom features an UPDATED, FULLY TILED, EASY-ACCESS SHOWER, and the WASHER AND DRYER located inside the laundry room will also remain with the home. Step outside and discover what makes this property truly special. Enjoy peaceful lake views, mature surroundings, a PRIVATE POOL and generous outdoor living space, all with plenty of room to create your own private waterfront oasis. With approximately 100 feet of direct frontage on Lake Hamilton, there is incredible potential to take full advantage of the Florida lakefront lifestyle. The home is in need of repairs and updating, presenting an excellent opportunity for buyers with vision to renovate, customize and add value while taking advantage of a hard-to-find affordable waterfront property. Important updates include a ROOF (2018), A/C (09/2024) and WATER HEATER (2025). Lake Hamilton is part of the Northern Chain of Lakes, offering access to interconnected waterways for BOATING, FISHING, WATERSPORTS and scenic cruising. Enjoy the tranquility of lakefront living while remaining conveniently located near Hwy 27 and located very close to Winter Haven, LEGOLAND Florida Resort and Port 27. Whether you're searching for a full-time residence, vacation home or renovation project, this property offers a RARE COMBINATION of ACREAGE, DIRECT LAKE FRONTAGE, A PRIVATE POOL, DETACHED GARAGE, OVERSIZED PARKING, NO HOA and tremendous potential in a beautiful Central Florida waterfront setting.

2900 Crump Road, Winter Haven

3059 Captain Jax Way, Winter Haven
$236,990
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This upscale new Summit two-story townhome provides ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3059 Captain Jax Way, Winter Haven

3039 Captain Jax Way, Winter Haven
$236,990
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This upscale new Summit two-story townhome provides ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3039 Captain Jax Way, Winter Haven

521 Adriel Avenue, Winter Haven
$350,000
4 Beds ⋅ 2 Baths ⋅ Ridge Acres Ph 02 SubDv. ⋅ 33880 Zip Code
Space, privacy and thoughtful updates come together in this spacious 4-bedroom, 2-bath home offering approximately 2,280 sq ft of living space on over half an acre! Step inside to an inviting open floor plan featuring a split-bedroom layout that provides added privacy and flexibility. Wood-look flooring flows through the main living areas. The kitchen was completely remodeled in 2022 and offers plenty of workspace while opening directly to the family room-perfect for staying connected while cooking, entertaining or enjoying everyday life. The generously sized primary suite provides a comfortable retreat, while additional bedrooms offer plenty of space for family, guests, a home office or hobbies. Outside, enjoy the extra room that comes with a large lot and no rear neighbors. Major improvements include a new roof in 2025, adding even more peace of mind. Conveniently located near major roadways with easy access to shopping, dining and entertainment. A 13-month home warranty is also included. Come see all the space and possibilities this home has to offer.

521 Adriel Avenue, Winter Haven

37 Lake Eloise Lane, Winter Haven
$515,000
3 Beds ⋅ 2 Baths ⋅ Harbour Estates SubDv. ⋅ 33884 Zip Code
Located in the desirable, tree-lined community of Harbour Estates, this custom-built 3-bedroom, 2-bath pool home offers expansive living spaces, and an exceptional outdoor lifestyle. Situated on an impressive .57-acre corner lot at the end of a quiet cul-de-sac, this property provides privacy, space and convenience in a highly sought-after location. Upon arrival, a grand courtyard welcomes you to sit and enjoy the beautifully landscaped grounds. A lovely leaded-glass front door with transom window opens into the inviting foyer, creating an elegant first impression. The generously sized Living Room features a striking stone fireplace, tray ceiling and strategically placed floor outlets that allow for flexible furniture placement. Three sets of glass sliding doors overlook the patio and pool area, bringing the outdoors in and creating a seamless connection between the interior and exterior living spaces. The eat-in Kitchen showcases a timeless black-and-white design, featuring crisp white cabinetry accented with crown molding and designer brushed-nickel hardware. Sleek black granite countertops beautifully complement the tile backsplash, while the kitchen sink is strategically positioned beneath a picture-frame window offering wonderful views of the pool. The upgraded stainless-steel appliance package includes a convection range, while recessed lighting illuminates the space. A cabinet pantry provides additional storage and a convenient coffee bar with a USB outlet adds both functionality and convenience to the kitchen. The charming breakfast nook provides the perfect spot for casual dining. The formal Dining Room features classic chair-rail molding and flows effortlessly into the kitchen, making it ideal for entertaining. The spacious 16' x 23' Primary Bedroom Suite features a beautiful coved ceiling and plenty of room for a comfortable sitting area. Additional features include wall-to-wall carpeting, a safe, and 2 closets, one of which is a walk-in closet. The luxurious Primary Bath offers dual comfort-height vanities with granite countertops, linen closet and walk-in shower with glass enclosure. A bidet and comfort-height toilet are located within the private water closet. A convenient access door leads directly to the patio. Two spacious Guest Bedrooms share a lavishly appointed Guest Bathroom featuring an oversized vanity, luxurious soaking tub accented by a decorative tile surround and a separate walk-in shower with glass enclosure. Outdoor living is truly exceptional in the fully fenced and meticulously landscaped backyard. A sparkling saltwater pool, surrounded by an expansive patio, provides the perfect setting for relaxing or entertaining family and friends. Distant views of Little Lake Eloise add to the tranquil setting. Additional features include a Laundry Room w/ cabinetry, washer & dryer, double-pane Pella fiberglass windows, glass storm door, water softener system, 2024 water heater, security system, stone-accent facade, 2023 architectural shingle roof, well for irrigation, freshly painted exterior, gutters, exterior lights, & 220-volt wiring in the oversized 3 car garage. The garage also features a garage door opener & provides abundant space for vehicles, storage or recreational equipment. Ideally situated in the picturesque community of Harbour Estates, this exceptional home offers the perfect blend of space, comfort, privacy, and convenience, just minutes from shopping, restaurants and LEGOLAND Resort.

37 Lake Eloise Lane, Winter Haven

1215 Fairlane Court Nw, Winter Haven
$335,000
3 Beds ⋅ 2 Baths ⋅ 33881 Zip Code
Come take a look at this beautifully maintained 3-bedroom, 2-bath home near the heart of Winter Haven, ready for its new owners! This property offers an optional HOA with no deed restrictions, giving you added flexibility. Step inside to a spacious, open dining and kitchen area featuring updated appliances and plenty of room for entertaining. Toward the rear of the home, you'll find a HUGE living space that offers plenty of room for the whole family to relax and gather. Situated on a DOUBLE LOT totaling nearly half an acre, this property provides an abundance of outdoor space, with plenty of room to add a pool in the future. The fully fenced yard offers privacy and a safe space for pets, while the large storage shed provides plenty of room for tools, equipment, and all your extras. The home is situated on a dead end road for added privacy and no through traffic. Major updates include a roof replaced in 2018 and a completely replaced AC system in 2023. Located in a quiet neighborhood, this home offers a peaceful setting while still being conveniently close to shopping, medical facilities, dining, and entertainment. Come see all this lovely home has to provide and make it yours today!

1215 Fairlane Court Nw, Winter Haven

100 El Camino Drive Unit 301, Winter Haven
$149,900
3 Beds ⋅ 3 Baths ⋅ Orchid Spgs Vill 100 Condo SubDv. ⋅ 33884 Zip Code
Welcome to 100 El Camino Drive, Unit 301, a spacious corner-unit condominium located in the established Orchid Springs community of Winter Haven. As one of the larger residences in the building, this home offers an appealing combination of generous living space, privacy, convenience, and low-maintenance Florida living. The thoughtfully designed floor plan provides each bedroom with its own private full bathroom, making the home especially well suited for guests, multi-generational living, or owners who simply appreciate added privacy. As a corner unit, the residence benefits from an enhanced sense of separation and space, while additional storage provides room for seasonal items and everyday necessities. Major improvements include a 2023 Heating system and the home has been replumbed throughout, offering valuable updates for the next owner. Additional conveniences private storage, elevator access, and a designated parking space. Orchid Springs offers a peaceful residential setting highlighted by beautifully maintained grounds and scenic water features, along with access to a private community pool and clubhouse. The monthly association fee provides exceptional convenience by including water, gas, cable, internet, and trash service, helping simplify monthly expenses. Community amenities also include pool and clubhouse access, with association services supporting an easy, low-maintenance lifestyle. The location places you in the heart of everything Winter Haven has to offer. Enjoy convenient access to shopping, dining, medical services, downtown Winter Haven, LEGOLAND® Florida Resort, and the famous Winter Haven Chain of Lakes. Known as the “Chain of Lakes City,” Winter Haven offers abundant opportunities for boating, fishing, kayaking, waterfront dining, and other outdoor recreation while remaining conveniently positioned within Central Florida. Spacious, updated, and packed with included amenities, Unit 301 offers an excellent opportunity to enjoy comfortable condominium living in one of Winter Haven’s most distinctive established communities.

100 El Camino Drive Unit 301, Winter Haven

Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ Magnolia Preserve Ph 4 SubDv. ⋅ 33880 Zip Code
Welcome to 5135 Magnolia Preserve Blvd, Winter Haven. This beautifully maintained 3-bedroom, 2-bathroom, home offers the perfect combination of comfort, space, and convenience. Designed with an inviting open-concept floor plan, split bedrooms and vaulted ceilings. This residence provides ample room for both everyday living and entertaining. The kitchen includes a seated bar that overlooks the great room. The private master bedroom suite boasts a large walk-in closet. Property also includes a whole-house water filtration system and an 8' x 12' backyard shed. This home was built in 2019 by Southern Homes and sits on a nice size lot featuring an attached 2 car garage. Easy access to freeways, restaurants, shopping, boating, fishing charters, and LEGOLAND. The neighborhood is walking distance from Eagle Lake complete with boat ramps, rolling hills and beautiful sunsets. This property presents an excellent opportunity to enjoy the best of Central Florida living.

Winter Haven

6059 Navona Way, Winter Haven
$309,990
4 Beds ⋅ 3 Baths ⋅ Villamar Phase 7 SubDv. ⋅ 33884 Zip Code
Under Construction. Introducing the Crestview floorplan, a unique two-story all block construction home available in Villamar, one of our communities in Winter Haven, Florida. Inside this 4 bedrooms, 3-bathroom home you will find 1,866 square feet of desirable living. As you step through the foyer you are greeted with a well-appointed kitchen that features an island with bar seating, cabinets for storage, quartz countertops and stainless-steel appliances. The kitchen overlooks the dining room, living room and outdoor patio making entertaining guests or enjoying time with family easy. The first floor also features a powder room. Perfect for keeping your privacy during guest visits. The second floor is complete with the primary bedroom, three additional bedrooms, a loft, and the laundry room. The primary bedroom includes its own bathroom with a dual vanity sink, separate shower and spacious walk-in closet. Like all homes in Villamar, the Crestview includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

6059 Navona Way, Winter Haven

6055 Navona Way, Winter Haven
$336,990
5 Beds ⋅ 3 Baths ⋅ Villamar Phase 7 SubDv. ⋅ 33884 Zip Code
Under Construction. The Robie is a two-story floorplan featured in Villamar in Winter Haven, Florida. With 2 exteriors to choose from, the Robie is sure to turn heads. Inside this inviting 5-bedroom, 3-bathroom home, you’ll find 2,447 square feet of comfortable living. This impressive all concrete block construction, two-story plan features a versatile floorplan to fit your needs. A spacious open-concept first floor which includes a well-appointed kitchen with sleek stainless-steel appliances overlooking the living and dining area. Just off the living room you will find the singular downstairs bedroom and full bathroom. As you move upstairs you are greeted with a spacious living and foyer space to utilize for work or play. The primary bedroom one is located just off the loft space and features a spacious walk-in closet as well as ensuite bathroom with double vanity and all the space you need to get ready in the morning. Three additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well as extra storage closets. Like all homes in Villamar, the Robie includes smart home technology, which allows you to control your home anytime with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

6055 Navona Way, Winter Haven

215 S Lake Howard Drive, Winter Haven
$419,000
3 Beds ⋅ 2 Baths ⋅ Linger & Nichols Sub/Winter H SubDv. ⋅ 33880 Zip Code
LAKEFRONT OPPORTUNITY ON LAKE HOWARD! Enjoy the Winter Haven waterfront lifestyle at 215 S Lake Howard Drive. This 3-bedroom (with bonus room off bedroom- possibly and office overlooking the lake), 2-bath home includes lakefront property directly across Lake Howard Drive from the residence, providing access to beautiful Lake Howard along with a private dock and covered boat area. The home has recently been refreshed and is ready for its next chapter, featuring fresh interior paint, new carpet and padding, professional cleaning, and professionally steam-cleaned tile. The floor plan offers comfortable living spaces, a single-car garage, and a large screened rear patio overlooking the spacious, fenced backyard. Across the street, your lakefront area provides the opportunity to enjoy boating, fishing, and everything that makes living on Lake Howard so special. Keep your boat conveniently at the dock and head out on the water to enjoy the Central Florida lake lifestyle. The home offers a great foundation for a buyer looking for waterfront access while still having the opportunity to make additional improvements and personalize the property. With some added love and updating, this could become a wonderful full-time residence, seasonal Florida home, or lake retreat. Conveniently located near downtown Winter Haven, shopping, dining, medical facilities, and area attractions, this property combines an established location with one of Winter Haven's most desirable amenities—access to Lake Howard right across the street. Bring your vision, your boat, and your love of the water and discover the possibilities at 215 S Lake Howard Drive!

215 S Lake Howard Drive, Winter Haven

4230 Roberta Drive, Winter Haven
$360,000
5 Beds ⋅ 3 Baths ⋅ Buckeye Rdg SubDv. ⋅ 33881 Zip Code
Welcome to 4230 Roberta Drive in Winter Haven! This spacious single-family home offers 5 bedrooms, 3 bathrooms, and approximately 2,616 sq ft of heated living area, providing plenty of space for comfortable everyday living. The home features a functional layout with the primary bedroom located upstairs, central A/C and heating, and a 2-car attached garage. With generous living spaces and a practical floor plan, this home offers plenty of possibilities to make it your own. Seller is offering up to $10,000 toward buyer’s closing costs, subject to agreed-upon terms. Enjoy the benefit of a remarkably low association fee of only $275 per year. Conveniently located in Winter Haven with access to shopping, dining, services, and everyday conveniences. A great opportunity to make this property your next home. All information is deemed reliable but should be independently verified by buyer and buyer’s agent.

4230 Roberta Drive, Winter Haven

815 Lake Jessie Drive, Winter Haven
$595,000
4 Beds ⋅ 4 Baths ⋅ East View Pkwy SubDv. ⋅ 33881 Zip Code
Virtually Staged. Mediterranean-Style Estate with Private Casita, Pool, Covered 2-Car Garage, Spacious Workshop & NO HOA in Winter Haven. Welcome to a truly unique Mediterranean-style estate offering over 4,100 square feet of living space, exceptional versatility, and the freedom of no HOA. This spacious property features a main residence plus a private casita, creating an ideal setup for multi-generational living, extended family, guests, a private home office, or flexible additional living space. Inside, you'll find generous living areas, beautiful architectural details, and plenty of room for both everyday living and entertaining. Recent improvements include a NEW ROOF and NEW AC, offering added peace of mind for the next owner. Enjoy your own private outdoor oasis featuring a beautiful saltwater pool with a new heating and cooling system, complemented by a poolside cabana, perfect for relaxing and entertaining year-round. The property also features a covered 2-car garage and an ample workshop, providing excellent space for vehicles, hobbies, projects, tools, storage, or recreational equipment. Need even more room for your toys? With no HOA and ample parking for boats, RVs, and recreational vehicles, this property offers the space, flexibility, and freedom that can be difficult to find. Conveniently located near Winter Haven's famous Chain of Lakes, you'll be close to boating, fishing, recreation, shopping, dining, and everything the area has to offer. Whether you're searching for a family estate, multi-generational home, private guest accommodations, a home with income potential, or simply a distinctive property with plenty of space and privacy, this home offers endless possibilities. Can't tour in person? Virtual tours are also available! Contact us today to schedule your private showing or virtual tour and experience everything this exceptional Winter Haven property has to offer.

815 Lake Jessie Drive, Winter Haven

124 Edgewater Drive, Winter Haven
$239,999
3 Beds ⋅ 1 Baths ⋅ Carefree Cove SubDv. ⋅ 33881 Zip Code
MOTIVATED SELLER Welcome to this charming home tucked into the desirable Carefree Cove neighborhood of Winter Haven. This 3 bedroom, 1 bath home is as cute as a button and features a beautiful living space that has been thoughtfully remodeled throughout, offering move-in-ready comfort with none of the guesswork. The front exterior has custom woodwork making a modern statement as soon as you pull up. A long driveway can accommodate multiple vehicles or storage for a boat or RV. Upon stepping inside you'll find brand-new laminate flooring flowing throughout every room, making clean ups and pet care easy peasy as there is NO carpet anywhere in the home. An upfront drop-zone is perfect for slipping on your shoes or storing purses & backpacks. Love to entertain??? Then the large family room will check these boxes! With a beautiful fireplace as a focal point, you'll also have a cafe section perfect for popcorn & snacks with a beverage fridge tucked in the corner. Tons of windows throughout make this a bright and airy home. The kitchen has been upgraded to butcher block countertops that are stunning on the eyes. A large pantry can easily accommodate all the big cases of water, rolls of paper towel & much much more! Just off of the kitchen is a nicely sized dining room. This can hold a large formal table and still have room for a serving buffet or credenza for extra storage. All 3 bedrooms feature new closet sliding doors. Major system upgrades give buyers extra peace of mind, including a brand-new roof and a 4-year-old air conditioning system. The big-ticket items are already taken care of. This home sits on a generous 7,279 sq ft lot with a fully fenced rear yard and a bonus screened patio, perfect for enjoying Florida evenings. Fire up the grill and enjoy BBQing while cozying up to a fire-pit in your rear backyard oasis. Solid block construction and a slab foundation add to the home's durability. Ideally located just off Carefree Cove Drive near the water, this home offers a quiet, established neighborhood feel while remaining close to Winter Haven's shopping, dining, and the area's famous chain of lakes. Whether you're a first-time buyer, downsizer, or investor, this fully updated home is ready for its next chapter. Schedule your showing today!

124 Edgewater Drive, Winter Haven

930 Cattleman Street, Winter Haven
$345,000
5 Beds ⋅ 3 Baths ⋅ Inman Grvs Ph 2 SubDv. ⋅ 33881 Zip Code
Discover the perfect family lifestyle at 930 Cattleman St, located in the Inman Groves community of Winter Haven, Florida. This Lennar Boston model features a modern and spacious layout with 5 bedrooms and 2.5 bathrooms, ideal for those looking for comfort and plenty of room to grow. The first floor features an open-concept kitchen that seamlessly connects to the living area, creating the perfect setting for family gatherings and entertaining. It also includes a versatile flex space that can be used as a formal dining room, home office, or playroom. Upstairs, you’ll find all five bedrooms, including a spacious primary suite with a private bathroom and walk-in closet. The home also offers the added convenience of a two-car garage. With a generous backyard and convenient access to shopping, schools, and major roadways, this home offers an excellent combination of peaceful living and connectivity. Don’t miss the opportunity to live or invest in one of Winter Haven’s growing areas!

930 Cattleman Street, Winter Haven

2668 Rutledge Court, Winter Haven
$232,000
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Beautifully Upgraded 1-Story Townhome|Low-Maintenance Florida Living! 2 BR PLUS BONUS ROOM-can be used as 3rd Br/2 Full BA home featuring GORGEOUS wood-plank Italian tile floors with authentic real-wood look, designer selected paint-pallets for a neutral interior to make your own. Upgraded carpet in bedrooms, HUGE Walk-in closet in Master BR, custom light fixtures with dimmer in Dining Room for softer lighting when desired. Stainless steel appliances in kitchen with range above oven and disposal. Separate laundry room with storage closet near kitchen. Enjoy soaring high ceiling with sky light and open floor plan with kitchen/dining room/living room adjacent for an open and airy feel. Upgraded ceiling fan/light combos for cool interior, as well as custom outdoor fan to stay cool on your screened in back porch, overlooking beautiful lined oak trees. The garage is designed for convenience with custom ceiling storage racks to provide organization for tools, recreation equipment, and all your Florida lifestyle essentials, while still being able to park in the garage and your private driveway. The Verandahs amenities include gated community pool & private dock on Lake Reeves. Winter Haven is renowned for its famous Chain of Lakes, making this charming town an ideal location for boating, fishing, and outdoor enthusiasts. Conveniently located within easy reach of the attractions and entertainment of Orlando and Tampa, as well as major international airports, this home offers an appealing combination of tranquillity and accessibility. A wonderful opportunity to enjoy comfort, style, recreation and the best of Central Florida!

2668 Rutledge Court, Winter Haven

5281 Pebble Beach Boulevard, Winter Haven
$279,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Begin the next exciting chapter of your life in Lake Ashton, Central Florida’s premier 55+ active-adult community, where this beautifully maintained and tastefully updated 2-bedroom, 2-bath home with den offers the perfect combination of comfort, convenience, and Florida lifestyle living. Ideally situated on a desirable corner lot with a generously sized yard, this inviting home welcomes you with its attractive curb appeal and continues to impress with thoughtful updates and quality features throughout. The kitchen offers 42-inch upper cabinets and solid-surface countertops, while beautiful wood flooring flows through the living room and den, creating a warm and inviting setting for relaxing or entertaining. The bedrooms feature newer carpeting for added comfort, and important major improvements provide exceptional peace of mind, including a new air-conditioning system and electric water heater in 2018, a new roof in 2023, and exterior painting completed last year for a fresh, crisp appearance and added weather durability. The washer & dryer are newer. Best of all, this exceptional home is being sold turnkey, including the furniture, electronics, furnishings, golf cart, and charger, making it possible to move in and immediately begin enjoying the Florida lifestyle without the hassle of furnishing a new home. Adding even more value, the seller is offering a $4,500 credit at closing toward new kitchen appliances. Beyond your front door, Lake Ashton delivers an extraordinary resort-style lifestyle with two 18-hole championship golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, indoor and outdoor swimming pools, pickleball courts, a bowling alley, and an impressive calendar of clubs, activities, social events, and opportunities to make new friends. With its desirable corner-lot setting, spacious yard, numerous updates, turnkey convenience, golf cart, and access to one of Central Florida’s most sought-after active-adult lifestyles, this is a home that deserves to be experienced in person. Schedule your private showing today and discover how enjoyable your next chapter could be at Lake Ashton.

5281 Pebble Beach Boulevard, Winter Haven

1540 S Lake Shipp Drive, Winter Haven
$215,000
2 Beds ⋅ 1 Baths ⋅ Lake Shipp Heights SubDv. ⋅ 33880 Zip Code
Welcome home! If you’ve been looking for a home with a little more room to enjoy both inside and out, this 2-bedroom, 1-bath Winter Haven home may be just what you’ve been waiting for. As you step inside, you’re welcomed by a spacious living area with beautiful wood flooring and a brick fireplace that gives the room plenty of character. The kitchen features white cabinets, stainless steel appliances, plenty of counter space, and tile flooring. There’s also an additional enclosed space that gives you options—make it your home office, sitting area, playroom, or whatever works best for you. And wait until you see the outdoor space! Sitting on approximately 0.29 acres, the property is fully fenced with plenty of front yard and backyard space. Whether you enjoy entertaining, gardening, spending time outside with your pets, or simply want a little more room between you and your neighbors, there’s plenty of space to make it your own. You’ll also have a detached storage building for those extra items, an attached one-car garage, and a roof that is approximately 6 years old. And one more thing buyers will appreciate—NO HOA! Conveniently located in Winter Haven near shopping, dining, and everyday needs, this home gives you space, flexibility, and the freedom to make it your own. Come take a look and imagine yourself calling this one home. Schedule your private showing today!

1540 S Lake Shipp Drive, Winter Haven

117 Homewood Drive, Winter Haven
$350,000
3 Beds ⋅ 2 Baths ⋅ Homewood Sub SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to 117 Homewood Drive in Winter Haven! Situated on a spacious .36-ACRE LOT, this 3-bedroom, 2-bath home offers 1,762 square feet of heated and cooled living space, a versatile BONUS ROOM, screened-in POOL, FENCED backyard, and plenty of space for indoor and outdoor living. Inside, the family room features a wood-burning FIREPLACE, while the kitchen is equipped with new stainless-steel appliances. The bonus room provides additional flexibility for a home office, hobby room, playroom, or additional living space. Step outside to enjoy the screened-in pool, outdoor kitchen area, and recently RESURFACED back patio—an inviting setup for entertaining or enjoying Florida's year-round outdoor lifestyle. The fenced backyard also features a 5-year-old STORAGE SHED with a roll-up door and electrical access, providing convenient space for storage, equipment, or projects. Numerous recent improvements add to the home's appeal, including a NEW ROOF in 2023, A/C replaced in 2024, NEW WATER HEATER, NEW POOL PUMP & MOTOR, new stainless steel kitchen appliances, a resurfaced back patio in 2026, and an updated garage with TESLA charger that conveys. With .36 acres, a screened pool, bonus room, outdoor entertaining space, fenced yard, and substantial storage, this home offers plenty of versatility. Conveniently located with easy access to the Polk Parkway, shopping, dining, and other Winter Haven amenities. Schedule your private showing and experience all that 117 Homewood Drive has to offer!

117 Homewood Drive, Winter Haven

5369 San Pietro Drive, Winter Haven
$344,390
4 Beds ⋅ 3 Baths ⋅ Villa Mar SubDv. ⋅ 33884 Zip Code
Under Construction. Azure BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Welcome to The Azure, where modern design meets practical living in a home that has it all. With 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home is crafted for comfort and style. The extraordinary elevation and professionally designed landscaping create a captivating first impression. Step through the front door to discover luxurious vinyl plank flooring that extends throughout the open-concept layout. The kitchen shines with quartz countertops and all-new stainless-steel appliances, overlooking the dining area and patio. A convenient half bath is located downstairs for guests with a spacious laundry room upstairs. Upstairs, you’ll find all four bedrooms, including the expansive owner's suite with a walk-in shower, double vanities, and a spacious walk-in closet. A flexible recreation space upstairs provides an ideal spot for family gatherings. With a smart thermostat ensuring energy efficiency and comfort, the Azure seamlessly blends functionality and modern luxury. Close to it all, Villa Mar places you near the natural beauty of the Winter Haven Chain of Lakes, the charm of downtown Winter Haven, and family fun at LEGOLAND® Florida Resort. Back at home, residents enjoy community amenities including a pool, dog park, playground, and walking trails.  Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

5369 San Pietro Drive, Winter Haven

7808 Waterview Way, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Garden Villas Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Investor Special!! Welcome to resort-style living in the highly sought-after gated waterfront community of Winterset, where convenience meets comfort in this charming 2-bedroom, 2-bathroom 2-story condo. Step inside to discover a spacious living and dining room combo that creates an inviting atmosphere for relaxation and entertaining. The well appointed kitchen features appliances and a convenient breakfast bar, perfect for causal dining or morning coffee. The master bedroom suite features a generous walk-in closet, providing ample storage space. For your convenience, a stackable washer and dryer are included. This professionally managed community boasts a plethora of amenities, including a clubhouse, fishing pier, heated pool, hot tub, and tennis courts—all overlooking the serene Lake Winterset, part of the renowned "Chain of Lakes." Enjoy peace of mind with state-of-the-art security in this well-maintained environment. You’re just minutes away from Lego Land and conveniently located near Disney and other Florida amusement parks, shopping, dining, and more. Alternatively, relish the numerous community offerings, including a fitness center, shuffleboard, and expansive green spaces perfect for walking your family pet. Experience the perfect blend of leisure and lifestyle at Winterset!

7808 Waterview Way, Winter Haven

7002 Summit Circle, Winter Haven
$340,000
3 Beds ⋅ 2 Baths ⋅ Summit East Ph 02 SubDv. ⋅ 33884 Zip Code
Beautifully maintained 3-bedroom, 2-bath pool home in a quiet Winter Haven community with a low HOA of $260/year. This home offers extensive upgrades, modern finishes, and a bright, open layout designed for comfortable living. Major improvements include a new roof (2020), new AC (2020), tankless water heater (2021), updated windows (2018), Culligan water system (2016), and a new pool pump and filter (2025). The kitchen features granite countertops, stainless steel appliances, a breakfast bar, and excellent natural light. The bathrooms also include granite counters, updated fixtures, and a large tub in the primary suite. Paradise Walk in tub (2020) in second bathroom. Enjoy Florida living with a saltwater fiberglass pool, screened enclosure, covered patio, fenced yard and irrigation system. Interior highlights include multiple flex spaces, neutral paint, updated ceiling fans, clean flooring, and move-in ready condition. Located close to shopping, dining, medical facilities, Legoland, and major highways, this home offers strong value with thoughtful upgrades and excellent maintenance. Schedule your private showing today.

7002 Summit Circle, Winter Haven