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$199,000
2 Beds ⋅ 2 Baths ⋅ Oakview SubDv. ⋅ 33880 Zip Code
Turn-key elegance in one of Winter Haven’s 55+ community! Welcome home to Oakview, an immaculate, highly sought-after hidden jewel. This smokefree, move-in ready 2BR/2BA residence delivers the perfect balance of relaxation and functionality. You will love the attached neighbors. The heart of the home features a bright, open-concept living/dining area flowing into a kitchen with abundant cabinetry and appliances. Guests appreciate the split-bedroom layout, while the owner enjoys a serene suite with a large walk-in shower. Bonus space includes a flexible rear den—ideal for a library/hobby room. Truly low-maintenance living: the low $165/mo. One year whole house warranty. HOA covers your roof replacement, exterior painting, and lawn care! Spend your days exploring local dining, shopping, and Legoland, or travel easily via nearby Orlando and Tampa airports. Schedule a showing today! Move right in and enjoy! Room sizes are approximate. Buyer's agent to check HOA requirements. Attached to MLS. 5 unit building.

1525 Oakview Circle Se, Winter Haven
$355,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to 5337 Hogan Lane, Winter Haven, Florida 33884. This home for sale in Lake Ashton is located behind the secure gates of Lake Ashton, a Premier, Florida 55 Plus Community. This Biscayne Floor Plan home offers 1,833 sq. ft. living area, a covered and screened lanai, concrete pad in the back of the home and a paver driveway and paver walkway from the driveway to the side garage door. 5337 Hogan Lane is ideally situated on a premium lot with peaceful water view and no rear neighbors. From the moment you arrive, the home’s curb appeal stands out with well maintained and mature landscape. The poured curbing and stone in the landscaped areas will catch your attention. Inside, the bright open floor plan is spacious and inviting, with triple sliding glass doors in the Living Room and Double Sliding Glass doors in the Dinette Area. The sliders provide access to the screened/covered lanai—perfect for relaxing and enjoying the tranquil water views year-round. The sought-after floor plan features a beautifully designed kitchen with 42” cabinetry with Moulding, Corian countertops, Under-cabinet lighting, Tiled backsplash, Breakfast bar seating, Wine Rack holder, and a window over the sink. There is also a window in the dinette area that allows natural light to fill the space. The primary suite offers serene pond views and includes an En-Suite bath with His and Her Vanities, 2 walk in closets, a soaking tub, and a separate room that includes a walk in shower with glass door enclosure, toilet and linen closet. A pocket door provides privacy between the Vanity and Shower areas. The guest bedroom and bath are located on the front of the home. A pocket door provides privacy for your overnight guests. The Flex Room has double doors that provide separation from the Living Room. The Flex Room is currently being used as a bedroom with twin beds and desk. It could easily be used as a Craft Room, too. Tile flooring runs throughout the main living areas for easy maintenance, while the bedrooms have comfortable carpeting. The laundry room is conveniently located off the kitchen and includes a solar tube and storage cabinetry. The garage offers a wash sink, Epoxy coating on the garage floor, the garage door has glass inserts, and a side door. Updates in this home include: A/C (2022), Water Heater (2019). Lake Ashton offers resort-style living with two 24-hour manned gatehouses, two clubhouses, heated indoor and outdoor pools, an indoor lap pool, fitness center, two championship 18-hole golf courses, pro shop, movie theater, bowling alley, billiards room, card rooms, arts and crafts studio, ballroom, three dog parks, and RV and boat storage. Schedule your private tour today.

5337 Hogan Lane, Winter Haven
$261,000
3 Beds ⋅ 2 Baths ⋅ Town Acres 25 SubDv. ⋅ 33881 Zip Code
Updated 3/2 home with new flooring, driveway, windows and siding.

2121 Greenway Drive, Winter Haven
$320,000
3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
Perfectly situated on a premium pond-front homesite in the sought-after 55+ gated community of Traditions at Lake Ruby, this beautifully maintained residence offers the ideal blend of comfort, space, and carefree Florida living. With 3 bedrooms, 2 bathrooms, and 2,109 square feet of thoughtfully designed living space, the open split-bedroom floor plan is perfect for both everyday living and entertaining. From the moment you arrive, the paver driveway, carriage-style lighting, manicured landscaping, and covered entry create impressive curb appeal. Inside, soaring ceilings and solid-surface flooring enhance the bright, open feel of the home. The spacious kitchen overlooks the family room and features 42-inch maple cabinetry with decorative rain-glass accents, Corian countertops, a breakfast bar, closet pantry, and a charming dining nook. Designed for gathering, the expansive family room is framed by triple sliding glass doors that showcase tranquil pond views and seamlessly connect to the oversized Florida room. Whether you're hosting friends or enjoying a quiet morning coffee, this inviting space provides the perfect backdrop, complete with views of the soothing waterfront fountain. The generously sized primary suite is a true retreat, offering its own waterfront sitting area, direct access to the Florida room, dual walk-in closets, and a spacious en-suite bath featuring a comfort-height double vanity, garden tub, seated walk-in shower, linen closet, and private water closet. Two additional bedrooms provide flexibility for guests, hobbies, or a home office, while the interior utility room includes a washer, dryer, and utility sink for added convenience. Additional highlights include a 2021 roof, 2024 HVAC system, 2018 water heater, gutters, security system, and a two-car garage with an additional refrigerator. Life at Traditions at Lake Ruby feels like a year-round vacation. Residents enjoy an impressive collection of resort-style amenities, including a lakefront clubhouse, heated pool and spa, fitness center, ballroom, library, billiards room, craft and meeting rooms, tennis courts, pickleball courts, bocce ball, basketball, shuffleboard, dog park, private dock, boat ramp, and a full calendar of social activities. The HOA provides exceptional value with lawn maintenance, exterior house painting, cable, internet, and full access to community amenities included. Conveniently located near shopping, dining, medical facilities, major highways, and LEGOLAND, this waterfront gem offers the perfect opportunity to enjoy an active, low-maintenance lifestyle in one of Central Florida’s most desirable 55+ communities.

3614 Plymouth Drive, Winter Haven
$140,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
You won't want to miss this opportunity. This 1344 sf home located in Oakwood Estates, a 55+ community. From the carport walk into the lanai, perfect for entertaining. From there step through the French doors into the open and inviting home with an open and updated kitchen with newer appliances including a cooktop, built in double ovens, built in microwave, and nice sized refrigerator. Past the kitchen you will see the comfortable dining area with built in cabinetry. Then follow through to the spacious living room with more built in cabinets. Returning back through the kitchen you will find the family room area which is open to the kitchen, just perfect for those family and friends get togethers. The main bathroom has been updated with a beautiful shower and updated stool. The guest bedroom is attached to this bath. At the back of the home you will find the primary bedroom complete with two built in closets and a nice sized bathroom attached. The shingled room was installed in 2025 and the air conditioner and water heater were installed in 2021. Oakwood Estates offers many amenities as well as activities. You can join in on the activities or just sit back and watch the world go by.

4146 Sprucewood Street, Winter Haven
$750,000
4 Beds ⋅ 3 Baths ⋅ Cypresswood Golf & Country Club SubDv. ⋅ 33884 Zip Code
*Special financing incentives may be available through the seller's preferred lender* Over 1 Acre with Golf Course Views in Cypresswood Golf & Country Club. Discover a rare opportunity to own one of the LARGEST residential lots in Cypresswood Golf & Country Club, one of Winter Haven's premier gated golf communities. Built in 2023 and situated on 1.17 acres, this exceptional 4-bedroom, 3-bathroom residence offers luxury, privacy, and modern living with expansive views of the 2nd green and 9th tee of the Ron Garl-designed championship golf course. A long private driveway lined with Florida-friendly landscaping leads to an expansive paver parking courtyard and oversized three-car garage featuring a professionally finished epoxy floor. Ebony-finished tongue-and-groove ceilings on both the front entry and rear screened lanai create an impressive first impression, while the Therma-Tru insulated front door with decorative glass insert welcomes you inside. The thoughtfully designed OPEN-CONCEPT FLOOR PLAN features luxury vinyl plank flooring throughout, soaring ceilings with decorative beam details, custom millwork, recessed lighting, and large windows that fill the home with natural light. The spacious great room is anchored by a custom shiplap feature wall with an electric fireplace and opens seamlessly to the covered lanai through oversized sliding glass doors. A premium Denon surround sound system serves both the great room and lanai, making entertaining effortless. The gourmet kitchen combines style and functionality with quartz countertops, a large center island, solid wood cabinetry, under-cabinet lighting, a walk-in pantry with custom shelving, Frigidaire Professional Series stainless steel appliances, and a natural gas cooktop. The spacious primary suite offers a tray ceiling with decorative beams, an oversized walk-in closet, and a luxurious ensuite bath featuring dual vanities, a garden tub, walk-in shower, and private water closet. The split-bedroom floor plan provides privacy for family and guests, and every bedroom includes a walk-in closet. Step outside and enjoy the freedom of owning more than an acre with panoramic golf course views and plenty of room to create your dream outdoor living space. Residents of Cypresswood Golf & Country Club enjoy an 18-hole championship golf course, clubhouse, restaurant, junior Olympic-sized pool, tennis and pickleball courts, and scenic roads perfect for walking, running, and biking. Conveniently located near US-27, I-4, the Polk Parkway, downtown Winter Haven, and LEGOLAND Florida Resort, this home offers an exceptional combination of luxury, space, and location.

440 Palma Ceia Road, Winter Haven
$235,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Villas/Green Bldg SubDv. ⋅ 33884 Zip Code
Situated in the desirable golfing community of Cypresswood Golf & Country Club, this lovely 2-bedroom, 2-bath townhome offers comfort, style, and beautiful golf course views. Upon arrival, you'll be welcomed by a charming courtyard adorned with pavers, creating a warm and inviting entrance. A glass storm door and smart lock entry provide both convenience and security. Inside, luxury vinyl plank flooring flows throughout the main living areas, enhancing the home's modern appeal and ease of maintenance. The open-concept floor plan features an updated kitchen with maple wood cabinetry embellished with brushed nickel hardware and soft-close hinges. Corian countertops beautifully complement the tile backsplash, while the custom center island serves as the heart of the home. Additional features include a stainless steel appliance package, recessed lighting, and a closet pantry for ample storage. The adjacent dining area is filled with natural light from an overhead solar tube skylight, creating a bright and cheerful space for meals and gatherings. The spacious living room features a convenient dry bar and oversized sliding glass doors that showcase peaceful views of the golf course. The primary bedroom suite serves as a relaxing retreat, offering dual closets and sliding glass doors leading to the Florida Room. The remodeled en-suite bathroom features a comfort-height vanity with Corian countertops, bronze fixtures, and a walk-in shower with a frameless glass enclosure and safety grab bars. The guest bedroom includes luxury vinyl plank flooring, a custom closet organizer system, and views of the private courtyard. The spacious Florida Room provides the perfect place to relax and unwind while enjoying tranquil golf course views through two oversized sliding glass doors. Additional Features: Laundry room with washer and dryer, Comfort-height toilets, Exterior lighting, Metal roof, Gutters with gutter guards. This home is being offered turnkey and fully furnished, making it truly move-in ready. Conveniently located within walking distance of the community clubhouse, restaurant, pub, swimming pool, and tennis courts, this property offers exceptional accessibility to Cypresswood's amenities. The monthly HOA fee of $320 includes: Exterior painting Roof maintenance Lawn care Additional memberships are available for golf and fitness center access. The picturesque Cypresswood Golf & Country Club features beautifully maintained grounds, a 24-hour manned gated entrance, and a welcoming lifestyle centered around golf, recreation, and community living.

664 Clubhouse Road, Winter Haven
$469,000
2 Beds ⋅ 3 Baths ⋅ Hendersons Ext Kenilworth Park SubDv. ⋅ 33881 Zip Code
New Lake Life listing, two houses one price. Must see property with no HOA. Chain of lakes property on Lake Mirror with generator and whole house water system. Main house has beautiful kitchen, big living/dining combo. Kitchen has extra-large refrigerator, island, wall tile, and entry to garage. Large living room has fireplace, storage, and muti doors to sunroom. Primary bedroom has walk in closet, ensuite bathroom, and doors to sunroom. Sunroom faces lake has storage and hurricane windows. Laundry room has washer, dryer, and storage. Covered back porch overlooks pineapple garden. Separate cottage comes fully furnished and has full bath, kitchen, pantry and closet. Cottage overlooks banana and avocado trees. Covered dock overlooks lake with a swing for relaxation. Each house has one bedroom. main house has space to build a second bedroom. 23 chain lakes are connected by canals. All information is deemed reliable but not guaranteed. Buyer must verify all information and measurements. No seller financing.

1620 17th Street Nw, Winter Haven
$345,000
3 Beds ⋅ 2 Baths ⋅ Sand Hill Lane SubDv. ⋅ 33884 Zip Code
Virtually Staged. Welcome to one of the premier homesites in Cypresswood Golf & Country Club. Perfectly positioned on a rare cul-de-sac lot, this beautifully maintained residence enjoys exceptional water frontage wrapping around two sides of the property, creating panoramic water views, enhanced privacy, and a serene setting rarely found within the community. Offering approximately 2,045 square feet of living space, this 3-bedroom, 2-bath home features a spacious, light-filled floor plan designed to maximize its spectacular waterfront location. Large windows throughout invite abundant natural light while framing picturesque lake views from multiple living areas and bedrooms. The home has been meticulously maintained and offers outstanding peace of mind with several major recent improvements, including a new roof (2021), new HVAC system (2019), and a completely renovated irrigation system (2025). These significant updates allow the next owner to focus on making the home their own rather than replacing major mechanical components. Inside, the home is clean, well cared for, and move-in ready, offering an excellent opportunity for buyers who prefer to personalize finishes to match their own style. Thoughtfully priced to reflect an original interior, it provides the flexibility to update the kitchen, flooring, and décor according to your vision instead of paying a premium for renovations chosen by someone else—all while enjoying one of Cypresswood's finest waterfront locations and the benefit of substantial recent capital improvements. Whether you're sipping your morning coffee while overlooking the lake, entertaining family and friends, or taking advantage of the golf, clubhouse, and other community amenities, this home offers an exceptional Florida lifestyle in a setting that is increasingly difficult to find. Rarely does a property combine such an outstanding waterfront location, expansive lake views, quiet cul-de-sac setting, and the opportunity to create your own dream home. Don't miss your chance to own one of Cypresswood Golf & Country Club's most desirable lakefront properties.

1819 Sandhill Lane, Winter Haven
$190,000
2 Beds ⋅ 2 Baths ⋅ Tanamora SubDv. ⋅ 33880 Zip Code
Very motivated seller! Welcome to your private slice of Old Florida! Nestled on a fully fenced half-acre lot, this well-maintained 2-bedroom, 2-bath home offers the perfect combination of space, privacy, and freedom with NO HOA restrictions. Inside, you'll find an inviting open floor plan featuring updated waterproof laminate flooring, a spacious kitchen with breakfast bar, and a comfortable living area ideal for everyday living and entertaining. The split-bedroom layout provides added privacy, while the screened rear porch creates the perfect place to enjoy morning coffee and peaceful wooded views. Outdoor enthusiasts, hobbyists, and business owners will appreciate the impressive 24' x 24' insulated metal garage/workshop with power, offering ample space for vehicles, boats, RV storage, projects, or a home-based business. Additional covered parking, storage buildings, and a large fenced yard provide even more versatility. Recent updates include a durable metal roof, updated HVAC system, updated plumbing, newer water heater, and fresh interior and exterior paint, allowing for worry-free ownership. The property backs up to expansive wooded acreage, creating a tranquil setting with no rear neighbors. Conveniently located with easy access to the Polk Parkway, I-4, Lakeland, Orlando, and Tampa, this property offers country-style privacy while remaining close to shopping, dining, and everyday amenities. Whether you're looking for a primary residence, winter retreat, or a property with room for all your toys, this unique opportunity delivers space, flexibility, and value.

312 Donald Lane, Winter Haven
$169,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Villas On The Green SubDv. ⋅ 33884 Zip Code
FLORIDA LIVING AT IT'S BEST!!! Don't miss out on this end unit, spacious 2 bedroom 2 bath townhome in a gated community. This unit is conveniently located right across the street from the clubhouse, pool, tennis courts and golf course!! Great for just starting out or ready to retire. Great Florida Room for relaxing when the weather is nice. Close to shopping and LegoLand!!

645 Broadmoor Circle Unit 645, Winter Haven
$175,000
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates SubDv. ⋅ 33881 Zip Code
Charming 2-Bedroom, 2-Bath Home on a Corner Lot Near Lake Henry. Welcome to this beautifully maintained 2-bedroom, 2-bathroom home, where pristine evidence is noticed from the moment you arrive. From the unique guitar-themed driveway artwork to the immaculate interior, this inviting residence is ready for you to move in and enjoy. Situated on a desirable corner lot, the home is located on a street that leads directly to the community boat dock overlooking scenic Lake Henry. Residents enjoy an active lifestyle with a variety of community amenities and social events offered throughout the month. Inside, the thoughtfully designed floor plan features a bright kitchen with white cabinetry, white appliances, and a convenient center island with seating—perfect for casual dining. Just off the kitchen, the indoor laundry area includes upper cabinets for additional storage and organization. The formal dining room offers a built-in china cabinet, creating an elegant space for entertaining family and friends. The adjacent family room flows seamlessly into the dining area and features sliding glass doors that open to an oversized lanai spanning nearly the entire width of the home, providing abundant space for relaxing and enjoying Florida living. Both bedrooms offer the convenience and privacy of en-suite bathroom access, making overnight guests feel right at home. Ideally located near shopping, medical facilities, restaurants, and live entertainment, this home also provides easy access to the many recreational and social activities available within the community.

6733 Kensington Drive Ne, Winter Haven
$379,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Atlee Add SubDv. ⋅ 33884 Zip Code
5553 Hogan Lane, Winter Haven, Fl. 33884 is located in Lake Ashton, a Gated and Guarded Premier 55+ community with Resort Style Amenities, Planned Activities, (2)-18 Hole Golf Courses, Pro Shop and Boat Slip Rentals. This St. Croix floor plan home with tile flooring throughout has a view of Lake Hart and has no backyard neighbors. You'll love the unobstructed view of the lake and the tranquil living this home offers. Upon entering you will love the Open and Spacious living area with cathedral ceilings, giving the home an expansive and airy feel. The focal point from the entrance of this home is the water view in the back of the home. Double French Doors open to the covered lanai and extended birdcage. This 2 Bedroom/2 Bath home with Flex Room offers over 1,858 sq. ft. living area. The expanded kitchen with additional cabinetry provides an abundance of storage and counter top space. Kitchen highlights include: granite countertops, tiled backsplash, maple cabinets, gas stove, breakfast bar and pendant lights. Initial Construction upgrades in this home include: pocket doors, 250 gallon propane tank buried to service stove & gas grill hook up, whole house water softener system, fans in all rooms, a whole house (except A/C) generator, the lanai is wired for hurricane shutters. The garage floors have epoxy finish, skeeter beater, wire shelving, attic above garage has flooring with pull down stairs for additional storage. Improvements since 2023 include: A/C Heat Pump and Air Handler have been replaced, Closets added to the Entry way, Guest Room and Flex Room, New Interior Paint, New Bosch Dishwasher, New Hardware on Cabinetry, Recessed Lighting in the Kitchen, New Chandelier, New Door Handles with Locks, New Toilets, Towel Fixtures, New Landscaping with Poured Curbing, New Plants and Rock. Residents in Lake Ashton enjoy a Main Clubhouse with Movie Theater, Bowling Lanes, Card, Craft and Billiard Rooms, Fitness Center and Outdoor Pool. There is also a Health and Fitness Center with Indoor Pool, Card, Craft and Billiard Rooms, Fitness Center with Sauna, Indoor 1/2 Court Basketball, Indoor Racquetball. Bocce Courts, Pickle Ball, and Tennis Courts are Enjoyed by Residents, Too. There is a great variety of clubs & activities available for residents. You can be as active as you like, or stay put & enjoy the serenity of your new home. Make an appointment to tour this home today!

5553 Hogan Lane, Winter Haven
$323,250
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 5 SubDv. ⋅ 33884 Zip Code
Spacious 3-Bedroom Home with Investment Potential Welcome to this beautifully maintained home featuring three generously sized bedrooms, including a primary suite with a walk-in closet, offering ample storage and comfort. The two additional bedrooms each feature built-in closets, perfect for family, guests, or tenants. Enjoy the convenience of two full bathrooms, a bright and open floor plan, and expansive living and dining areas that create the perfect space for entertaining or relaxing. The modern kitchen is both stylish and functional, ready for daily cooking or hosting gatherings. Additional highlights include a 2-car attached garage for secure parking and storage, and ceiling fans in all bedrooms and the living room, ensuring comfort and energy efficiency year-round. The home is also equipped with seamless gutters around the entire house, offering long-term durability and low maintenance. Whether you're looking for a primary residence or a smart investment property, this home checks all the boxes. With its spacious layout, attractive features, and low-maintenance upgrades, it’s a fantastic opportunity for investors seeking long-term value and strong rental appeal. Don't miss out—schedule your showing today and discover the potential this property offers!

2748 San Marco Way, Winter Haven
$237,500
3 Beds ⋅ 2 Baths ⋅ Orchid Springs Patio Homes SubDv. ⋅ 33884 Zip Code
Welcome to this wonderful 3 bedroom, 2 bathroom home located on a spacious corner lot with NO rear neighbors in the desirable Orchid Springs community in SE Winter Haven. NEW METAL ROOF PUT ON IN 2021 AND AC REPLACED IN 2023! Offering a versatile split-bedroom floor plan, this home features a living room, dining room and family room, providing plenty of space for both everyday living and entertaining. The bright and open living room showcases vaulted ceilings & glass doors that lead to a private courtyard, creating a seamless connection between indoor & outdoor living. The kitchen is centrally located and offers a spacious breakfast bar, closet pantry & ample cabinet & counter space, making it ideal for meal preparation & gathering with family & friends. The primary suite provides a relaxing retreat with a walk-in closet, garden tub, separate shower & also has access directly to the screened patio. Ceramic tile flooring throughout the home offers both durability & easy maintenance. Additional features include a 2-car garage with built-in storage, utility sink, and washer/dryer hookups. The fenced backyard offers privacy & room for pets, gardening, or outdoor enjoyment. Residents of Orchid Springs enjoy access to community amenities including a clubhouse & swimming pool, all while being conveniently located near shopping, dining, churches, medical facilities, golf courses & major roadways. Don't miss this opportunity to own a spacious home in one of Winter Haven's most established communities.

381 San Jose Drive, Winter Haven
$230,000
3 Beds ⋅ 2 Baths ⋅ Lake Dexter Woods Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to this charming home in the desirable Lake Dexter Woods community of Southeast Winter Haven. This well-maintained residence offers comfortable living with an open and inviting layout, spacious living areas, and abundant natural light throughout. The kitchen provides ample cabinet and counter space, while the primary suite features a private bath and generous closet storage. Enjoy Florida living year-round from the enclosed Florida room, perfect for relaxing or entertaining. The property also features a fenced backyard with mature landscaping and low-maintenance outdoor spaces. Residents of Lake Dexter Woods enjoy access to community amenities including a pool, boat ramp, and dock with access to Lake Dexter. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers both comfort and convenience in a sought-after location. This home has lots of updates! lighting, electrical panel and outlets, plumbing, 2021 Water heater, 2024 Roof, 2025 HVAC.

542 Lake Dexter Boulevard, Winter Haven
$589,500
5 Beds ⋅ 5 Baths ⋅ Elbert Hills SubDv. ⋅ 33880 Zip Code
Come and See this Amazing Lake Front Home Located in the Water Skiing Capital of the World, on Lake Elbert in Winter Haven, FL. As you enter the front door of this beautiful Home the hardwood floors will delight your eyes as you look down the long foyer to the right that leads pass the kid's 2 Bedrooms area for them to enjoy, to a large Family room with Lake Views that will be one of your favorite places to relax. Going back down the foyer you will end up seeing the 1st floor Master King Ensuite with Lake views and a private bathroom on the left, and the Stunning Gourmet Kitchen on the right flowing into a light-filled Dining Sunroom with Lake Views, perfect for entertaining. This Home is the ideal home to Live in full time, or Enjoy it here during your favorite time of the year, or use it for a short term rental or longer term while you're at your other home. This Home easily sleeps 10 with it's 5 Bedroom, 4.5 Bathrooms, a kid's area that will sleep 4, while the Adults can appreciate 3 King Master Ensuites with their own Bathrooms. The kid's 2 bedrooms area with a bathroom circles back with a door into the Kitchen, the HUB of the home. You can go out the rear door to the nice patio and the 2 car Garage / Game Room that also has the Laundry Room and a Full Bathroom with a walk in Shower. Back inside, going up to the 2nd floor you have a door going out to the balcony in the front of the home over the 1st floor patio that allows for the peaceful Lake views. The other 2 Master King Ensuites with Walk in Closets and Private Full Bathrooms. Sitting on almost 1/2 acre on a hill up from the Lake, this AMAZING HOME with so much to love and could be Yours's to ENJOY all year or create a Great Cash Flow for your Retirement. It is only about a 10 minutes drive to LEGOLAND, and aproxamently 30 minutes or so to DISNEY WORLD, UNIVERSAL STUDIOS, SEA WORLD, and OTHER PARKS, and only about 1.5 hours to the BEAUTIFUL FLORIDA BEACHES OR EITHER SIDE OF THE STATE. Come and See this Amazing Home the is Priced to SELL.

1302 Lake Elbert Dr Se, Winter Haven
$177,500
2 Beds ⋅ 2 Baths ⋅ Cypresswood Villas/Green SubDv. ⋅ 33884 Zip Code
Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa. Recent updates include new luxury vinyl flooring, new dishwasher and new microwave. MOVE IN CONDITION. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

1026 Medinah Drive, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Buckeye Haven SubDv. ⋅ 33881 Zip Code
Welcome to 1716 Terry Circle NE, Winter Haven, FL 33881, a beautifully maintained and fully furnished home offering the perfect blend of comfort, convenience, and investment potential. This move-in-ready property features ceramic tile flooring throughout, updated bathrooms, and a bright, open floor plan with spacious living and dining areas that flow seamlessly into a large kitchen with breakfast bar seating and all stainless steel appliances included. The thoughtfully designed layout provides privacy for the primary bedroom, separating it from the additional bedrooms to create a peaceful retreat. Tasteful furnishings and décor are included, making this a truly turnkey opportunity for homeowners, seasonal residents, or investors alike. The neutral color palette, abundant natural light, and functional layout create a warm and inviting atmosphere ideal for everyday living or entertaining guests. Adding to the home's value and peace of mind is a roof that is only five years old. One of the property's most attractive features is the absence of HOA fees and restrictions, offering greater flexibility and freedom for the new owner. Conveniently located in the heart of Winter Haven, the property is just minutes from LEGOLAND Florida Resort and Peppa Pig Theme Park Florida, making it an excellent choice for vacation home buyers and visitors. Residents will also enjoy easy access to the Winter Haven Chain of Lakes, offering endless opportunities for boating, fishing, and outdoor recreation. Nearby shopping, dining, schools, medical facilities, and the vibrant downtown district provide everything needed for comfortable Florida living. With convenient access to major highways connecting Orlando and Tampa, this fully furnished home presents a rare opportunity to own a turnkey property in one of Central Florida’s fastest-growing and most desirable locations. Showings will begin next week, so don't miss your chance to explore all that this exceptional home has to offer and schedule your private tour today.

1716 Terry Circle Ne, Winter Haven
$309,500
2 Beds ⋅ 2 Baths ⋅ Eloise Woods East Lake Mariam Unit SubDv. ⋅ 33884 Zip Code
This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearly non-existent electric bills thanks to a fully paid-off SolarEdge solar system, complemented by a whole-house 22 kW Generac generator with a 250-gallon propane tank, hurricane-rated windows, a 5-year-old architectural shingle roof, and a Rinnai tankless water heater. The spacious interior boasts a large galley kitchen with stainless steel appliances and a gas stove, a convenient indoor laundry room with extra storage, a 2-car garage, and a versatile 16x12 climate-controlled Florida room. This property has been an Airbnb and can be purchased fully furnished, making it a turnkey investment or a move-in-ready retreat!

132 Duval Road, Winter Haven
$439,900
5 Beds ⋅ 3 Baths ⋅ Buckeye Pointe SubDv. ⋅ 33881 Zip Code
Welcome to 3097 Buckeye Pointe Drive, a fully updated pool home in Winter Haven, Florida, offering the space, flexibility, and upgrades today's buyers are searching for in Polk County. If you've been looking for a move-in ready home with a private pool, screened spa, modern finishes, and no rental restrictions, this property deserves a spot at the top of your list.Located in the established Buckeye Pointe community, this spacious two-story home features 5 bedrooms, 2.5 bathrooms, and more than 2,500 square feet of living space. The versatile floor plan includes a first-floor bedroom, making it ideal for multigenerational living, visiting guests, a private home office, or a fitness room.From the moment you step inside, you'll notice the extensive updates throughout. The entire first floor showcases oversized 24x36 porcelain tile, creating a clean, modern look that is both stylish and easy to maintain. The renovated kitchen serves as the heart of the home with updated cabinetry, a large center island, upgraded lighting, and newer appliances including the refrigerator and dishwasher. Every bathroom has been remodeled, while fresh interior and exterior paint give the home a bright, updated feel throughout.Step outside and enjoy the Florida lifestyle year-round. The screened and heated pool and spa create the perfect setting for relaxing after work, entertaining family and friends, or enjoying weekend gatherings. The vinyl fenced backyard offers privacy, while mature fruit trees provide character and charm that are increasingly difficult to find. Major improvements include a newer 2023 roof and a 2020 water heater, giving buyers added confidence and helping reduce future maintenance concerns. One of the most attractive features of this property is the absence of rental restrictions. Buyers searching for an Airbnb-friendly home in Winter Haven, a Florida vacation home, a second home near Orlando attractions, or an income-producing investment property will appreciate the flexibility this community offers. Conveniently located near shopping, restaurants, medical facilities, schools, and major transportation routes, this home provides easy access to everything Central Florida has to offer. Whether you're commuting to Orlando, exploring nearby lakes, visiting world-famous attractions, or simply enjoying the growing Winter Haven lifestyle, this location puts you close to it all. Buyers frequently searching for "homes with pools in Winter Haven," "5-bedroom homes in Polk County," "updated homes near Orlando," "Airbnb investment properties in Central Florida," "homes with no rental restrictions," or "move-in ready Florida homes with a pool" will find everything they're looking for at 3097 Buckeye Pointe Drive. This is more than just a house. It's a move-in ready Florida lifestyle with room to grow, space to entertain, and the flexibility to fit your future plans. With a recent price improvement, this home offers exceptional value in today's market. Schedule your private showing and see everything this property has to offer.

3097 Buckeye Pointe Drive, Winter Haven
$342,990
3 Beds ⋅ 2 Baths ⋅ Cypresswood Mdws SubDv. ⋅ 33884 Zip Code
Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, but by far the most impressive one is this gem and it shows. As you pull up to the extended driveway, low maintenance landscape ushers you into a well appointed home. Once in the front door, sparkling floor tiles guide you through this beautiful 3 bedroom 2 bath split floor plan home. Quartz counters and wall to wall cabinet space give anyone that loves to cook the space they need to store items and create meals while hosting family or company. Right off of the kitchen there is a climate controlled Florida room, with an additional screened-in patio to the rear. When you are ready to retire for the evening, your primary bedroom has plenty of space to stretch out in and keep your belongings in the large walk-in closet. Move right in and leave your worries behind. Not only has the kitchen and flooring been recently upgraded, all your major components have been replaced within the last 5 years - brand new electric panel w/surge protection installed (May 2026), roof (2022) , water heater (2021), A/C (2021). Schedule your private tour and make this home yours for years to come.

419 Greenfield Road, Winter Haven
$215,000
2 Beds ⋅ 2 Baths ⋅ Stonebridge SubDv. ⋅ 33880 Zip Code
*PRICE IMPROVEMENT*~2/2 Winter Haven residence Offered for Sale~ Great opportunity for a first-time home buyer or an investor! This adorable 2/2 property features 1396 square feet of living area, a split plan, two bonus rooms which could be used as bedrooms, vaulted ceilings, primary bedroom with walk-in closet and en-suite bath, wood burning fireplace, large, screened patio and a one car garage. Property is wheelchair accessible. Roof and A/C are less than 5 years old and water heater is newer. Convenient to fishing, dining, shopping, and medical/educational facilities. Monthly HOA fee covers grounds maintenance, streetlights and community pool care.

2115 Kings Crossing Sw, Winter Haven
$334,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to resort-style living in the highly sought-after Lake Ashton Golf Club Community! This impeccably maintained home is nestled on a quiet and secluded street, offering the perfect combination of privacy, comfort, and an active Florida lifestyle. From the moment you arrive, you will appreciate the pride of ownership and pristine condition of this beautiful residence. Designed for both everyday living and entertaining, the home offers spacious living areas, abundant natural light, and a floor plan that flows effortlessly throughout. One of the most valuable features of this property is that the CDD bond has been fully paid off, providing significant long-term savings and added value for the new owner. Lake Ashton is one of Central Florida's premier gated 55+ communities, offering an unmatched array of amenities and activities. Residents enjoy access to two private 18-hole championship golf courses, including one of the most challenging and highly regarded courses in the region, making it a favorite among golf enthusiasts. The community also features two expansive clubhouses, a state-of-the-art health and fitness center, resort-style pools, tennis and pickleball courts, bowling lanes, movie theater, ballroom, restaurant and lounge, arts and crafts facilities, numerous social clubs, and a private marina with access to beautiful Lake Ashton. Whether you are looking for an active retirement, a seasonal retreat, or your forever home, this exceptional property offers the perfect opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and discover why so many residents proudly call Lake Ashton home.

5312 Nicklaus Drive, Winter Haven
$1,195,000
5 Beds ⋅ 6 Baths ⋅ Na SubDv. ⋅ 33881 Zip Code
Prepare to be captivated by this beautifully updated lakefront estate on Lake Hartridge, perfectly positioned along the highly sought-after Winter Haven Chain of Lakes. Situated on approximately 1.3 acres with an impressive 115 feet of waterfront, this exceptional property offers a rare combination of luxury, privacy, and breathtaking panoramic water views, all tucked away on a peaceful dead-end street. Mature oak trees and lush tropical landscaping create a timeless Old Florida ambiance while blending seamlessly with the home’s fresh, modern updates. A long private driveway welcomes you to the property, leading to an oversized detached two-car garage complete with a private apartment above—ideal for guests, multigenerational living, rental income, or a secluded home office—and a convenient full bathroom below. Inside the main residence, an expansive and thoughtfully designed floor plan features four spacious bedrooms and 4.5 beautifully appointed bathrooms. One bedroom is currently styled as a cozy movie room, creating the perfect entertainment space for relaxing evenings or family gatherings. The luxurious first-floor primary suite serves as a true retreat, offering a spacious sitting area with stunning views overlooking the sparkling screened pool and tranquil lakefront setting. The spa-inspired primary bathroom showcases a soaking tub, oversized walk-in shower, elegant dual vanities, and generous space designed for comfort and relaxation. At the center of the home is the beautifully updated gourmet kitchen, featuring sleek quartz countertops, modern cabinetry, stainless steel appliances, and abundant prep and storage space sure to impress any chef. Elegant porcelain flooring flows throughout the main living areas, while plush carpeting adds warmth and comfort to the bedrooms. Recent upgrades, including a new roof and new AC system, provide peace of mind and enhance the home’s fresh, move-in-ready appeal. Designed to maximize the spectacular lake views, the expansive lanai and private screened-in pool area with an in-ground hot tub create the ultimate outdoor oasis for year-round Florida living. Newly refreshed pool and lanai screening further elevate the experience, seamlessly blending indoor and outdoor entertaining spaces. For boating enthusiasts, the property truly stands out with a private covered dock featuring a metal roof and boat lift, offering direct access to the renowned Winter Haven Chain of Lakes, known for boating, fishing, watersports, and unforgettable sunset cruises. Additional highlights include dedicated RV parking with electrical, water, and sewer hookups, making this property ideal for those seeking adventure without sacrificing luxury and convenience. Located in the heart of Winter Haven, known as the “Chain of Lakes City,” residents enjoy easy access to over 50 interconnected lakes, waterfront dining, boutique shopping, recreational trails, and convenient access to both Tampa and Orlando attractions. This extraordinary lakefront estate perfectly combines modern updates, timeless elegance, and resort-style living—offering a truly rare opportunity to own a one-of-a-kind waterfront retreat.

250 Brigham Road Nw, Winter Haven
$342,900
3 Beds ⋅ 2 Baths ⋅ Residences At Winter Haven SubDv. ⋅ 33880 Zip Code
Under Construction. Under Construction. Discover the Key West by LAREF Homes, a thoughtfully designed 3-bedroom, 2-bath home that blends modern style with everyday functionality. Located in Residences at Winter Haven, an exclusive 63-lot semi-custom community, this home offers exceptional craftsmanship in a prime central Winter Haven location. The open-concept floor plan is complemented by a dedicated formal dining room, making it perfect for both everyday living and entertaining. At the heart of the home, the designer kitchen features a stunning waterfall island, 42-inch soft-close cabinetry with crown molding, a spacious walk-in pantry, premium stainless-steel appliances, and abundant storage. Additional highlights include luxury vinyl flooring throughout the main living areas, floor-to-ceiling porcelain tile in the shower, smart home technology, a dedicated laundry room with a utility sink, blinds throughout, four ceiling fans, and a 2-10 Home Buyers Warranty. Residents enjoy low HOA fees of just $225 quarterly, no CDD fees, and the opportunity to personalize future homes by selecting their lot, floor plan, exterior finishes, interior design package, and upgrade options. Estimated completion is at the end of June.

2121 River Hawk Loop, Winter Haven
$495,000
2 Beds ⋅ 3 Baths ⋅ Raingarden SubDv. ⋅ 33880 Zip Code
Discover your dream residence at RainGarden Condominiums in Downtown Winter Haven! Designed by renowned architect Max Strang, this stunning townhouse embodies a modern design within a tropical landscape that provides an atmosphere of serenity in the heart of a lively downtown. Prepare to be wowed by the blend of contemporary aesthetics and organic elements, transforming this two-bedroom, two-and-a-half-bathroom residence into a unique piece of architecture! This interior unit is one of nine townhomes that make up the RainGarden Condominium. Upon entering the secured gate into your private courtyard, you’ll immediately notice the lush landscaping and shady tree canopies that provide a peaceful place to relax or entertain guests. Step inside and enjoy a spacious and airy layout that effortlessly connects the living, dining, and kitchen areas. The large custom windows bathe the space in natural light, while the randomized, vertical fins on the front facade provide generous shading and privacy to the outside. The living room dazzles with 9'9" ceilings, elegant concrete floors, dining area, and expansive floor-to-ceiling windows. The gourmet kitchen features a breakfast bar, high-end GE appliances, granite countertops, and ample cabinet space, blending functionality with style. Access your second story via an integrated wooden stairway situated in a clerestory expanse that opens to a skylighted landing. Upstairs, the lofted master bedroom beckons with floor-to-ceiling windows, refined wood floors, an en-suite bathroom, and abundant closet space. The master bath features a double vanity, a large walk-in shower with elegant finishes, and a spacious walk-in closet. The second bedroom boasts a similar en-suite bathroom with a walk-in closet and plenty of storage. Enjoy the convenience of a second-floor washer and dryer as well as an ample storage closet. Located in the heart of Downtown Winter Haven, this home offers an urban lifestyle where you can “live, work, and play” all within a few blocks. You can leave your vehicles in the attached two-car garage and enjoy the vibrant neighborhood with new restaurants, coffee shops, retailers, and other entertainment just steps away. There are also additional visitor parking spots in the rear and ample street parking available on Ave A. This location cannot be beaten! Centrally located between Tampa & Orlando and within 1 1/2 hours of both east-coast and west-coast beaches. Or take your family out on the coveted Chain of Lakes where you can boat or swim between 22 different lakes! Don’t miss out on the opportunity to purchase this architectural gem! HOA provides for trash pickup, sewer, common electric and water expenses, exterior maintenance and landscaping.

154 2nd Street Sw Unit Unit 7, Winter Haven
$295,000
3 Beds ⋅ 2 Baths ⋅ Cypress Landing Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome Home To This Spacious 3-Bedroom, 2-Bathroom Residence Featuring An Open-Concept Floor Plan Built For Florida Living. Recently Refurbished With Fresh Interior And Exterior Paint And Luxury Vinyl Flooring Throughout, Modern Custom Kitchen Cabinets With Granite Counter Tops. This Home Is Move-In Ready From Day One. The Expansive Living/Dining Room Combo Flows Into A Well-Appointed Kitchen, Anchored By A Dramatic Full Brick Fireplace Wall That Adds Warmth And Character You Rarely Find At This Price Point. A Utility Room Is Conveniently Located Between The Kitchen And Garage, Perfect For Daily Function. The Primary Suite Is A True Retreat, Positioned With Direct Access To A Dedicated Office/Nursery Flex Space And A True Interior Florida Room Filled With Windows And Natural Light, Creating A Connected Rear Wing That Adapts To However You Live. Two Additional Bedrooms Share A Full Secondary Bath, And The Attached 2-Car Garage With Concrete Side Patio Rounds Out A Home Built For Real Life. The Home; Situated Just Steps From The Amenities Of Cypress Landing On Lake Dexter — A Peaceful Lakeside Community Offering Pickleball And Tennis Courts, Boat Storage, A Private Boat Ramp, Dock, Community Pool, And Clubhouse. Located Just 1.8 Mile From Legoland Florida, Nestled Between Orlando And Tampa With Easy Access To Theme Parks And Beaches, And Just Minutes From 5 Star Rated Dining And Shopping In Downtown Winter Haven And Other Nearby Cities.

4114 Fishermans Landing, Winter Haven
$405,000
2 Beds ⋅ 2 Baths ⋅ Winterset 04 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Beautiful lakefront living awaits in the gated community of Winterset! This beautifully maintained 2-bedroom, 2-bathroom condo with an attached one-car garage offers stunning lake views, abundant natural light, and unique architectural details throughout. Inside, you’ll find beautiful cork flooring, specialty tray ceilings, and a cozy library area complete with custom built-in shelving. The spacious enclosed Florida room is a true showstopper, featuring floor-to-ceiling windows overlooking the lake, creating the perfect space to relax and enjoy breathtaking water views year-round. The oversized primary suite offers a spacious layout with dual sinks, a walk-in closet, and a peaceful retreat-like feel. The large custom kitchen is a chef’s dream, complete with a gas stove, ample cabinetry, generous counter space, and plenty of storage for all your culinary needs. Enjoy the beautiful community amenities that include a pool, tennis courts, and the security and privacy of this sought-after gated neighborhood. Conveniently located near Legoland, shopping, dining, and everyday conveniences. This lakefront condo perfectly blends comfort, elegance, and Florida lifestyle living.

75 Sunset View Drive Unit 75, Winter Haven
$590,000
4 Beds ⋅ 4 Baths ⋅ East View Pkwy SubDv. ⋅ 33881 Zip Code
Step into timeless elegance with this stunning Mediterranean-style estate in the heart of Winter Haven. Offering over 4,100 square feet of living space, this one-of-a-kind property features a private casita, private pool, and endless possibilities for multi-generational living, guest accommodations, or a home office. Recent updates include a new roof and new AC, giving buyers peace of mind while preserving the home's unique character and charm. Enjoy spacious living areas, beautiful architectural details, and plenty of room for entertaining both indoors and outdoors. With no HOA, ample parking for boats, RVs, and recreational vehicles, and a prime location near Winter Haven's famous Chain of Lakes, this property combines flexibility, privacy, and convenience. Whether you're looking for a family retreat, a home with income potential, or a distinctive property that stands out from the ordinary, this exceptional residence is a must-see. Schedule your private tour today and discover everything this remarkable home has to offer!

815 Lake Jessie Drive, Winter Haven