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$109,900
2 Beds ⋅ 2 Baths ⋅ L4958845 MLS ⋅ C BLDG.
Welcome to Winter Haven Harbor condos a 55+ community. This two bedroom one bath condo is an end unit and it is on the first floor, very close to your parking spot. The home has Nice laminate flooring throughout. The Dining room is next to kitchen, a little open concept area. The master bedroom has a nice size walk in closet. The home also boasts new energy efficient windows. The community features a massive heated pool, clubhouse with exercise room, kitchen, pool table, shuffleboard, and a grilling area with a nice area to entertain friends and family. This community also features a car washing area. Public bus transportation-Citrus connection available right out front. Buyer approval required. You are walking distance from shopping, Hospital and other medical centers. Centrally located between Tampa and Orlando. Schedule your appointment to view this home and make it yours today.

1700 6th Street Nw Unit C1, Winter Haven

Courtesy of HARPER REALTY FL, LLC

$275,000
3 Beds ⋅ 2 Baths ⋅ W7882124 MLS
Short Sale. APPROVED SHORT SALE AT PRICE! CHAPTER 7 BANKRUPTCY - Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional Kitchen Overlooking The Main Living Space. Fenced Yard. Ideal For Everyday Living And Entertaining. Built In 2019, Conveniently Located Near Shopping, Dining, Schools, And Major Roadways With Easy Access Throughout Winter Haven. Brand New Publix store just open around the corner of Country Club Cir. Bankruptcy Short Sale — Third-Party Approval Required. Property Sold As-Is. Great Opportunity For Owner-Occupants Or Investors Seeking Value In A Growing Area. Call Today For Details Or To Schedule A Private Showing.

3180 Country Club Circle, Winter Haven

Courtesy of DALTON WADE INC

$279,975
3 Beds ⋅ 2 Baths ⋅ P4937588 MLS
JUST REDUCED TO $279,975 – Better Than New and Ready for Immediate Move-In! Why wait months for new construction when you can move into a home that's already complete, beautifully maintained, and packed with value? This immaculate 4-bedroom, 2-bath home has been meticulously cared for and offers the peace of mind and convenience today's buyers are looking for. Unlike many new construction homes, there's no waiting on builders, no surprise upgrade costs, and no unfinished landscaping—just unpack and start enjoying your new home from day one. Inside, you'll find a bright, open floor plan with spacious living areas, a desirable split-bedroom layout, updated finishes, and a fresh, move-in-ready interior. Every detail has been thoughtfully maintained, making this home feel practically new without the premium price tag. Outside, you'll enjoy an established neighborhood with mature surroundings and a yard that's ready to enjoy—not one that still needs time and money to complete. Now offered at just $279,975, this home represents an incredible value in today's market. If you're looking for a home that offers the benefits of new construction without the added expense or wait, this is one you don't want to miss. Schedule your private showing today and see why this home stands out from the competition.

257 Meadowbrook Boulevard, Winter Haven

Courtesy of KELLER WILLIAMS REALTY SMART 1

$451,000
4 Beds ⋅ 3 Baths ⋅ L4958667 MLS
SELLER VERY MOTIVATED! Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy atmosphere created by large windows that allow natural light to flood the home. The home features stunning luxury vinyl plank flooring and a beautiful brick fireplace, adding warmth and character to the space. The kitchen is of good size and boasting sleek countertops, new modern appliances, and ample cabinet space. Enjoy casual meals in the eat-in kitchen or step outside to the screened-in porch, an ideal spot for dining al fresco or simply relaxing while overlooking the expansive backyard and pool. Come add your personal touches and make this house your beautiful home!

148 Lake Otis Road, Winter Haven

Courtesy of LOCKHART & ASSOCIATES INC

$232,000
3 Beds ⋅ 2 Baths ⋅ O6374521 MLS
Short Sale. Back on the market -Short Sale opportunity on a 2023-built 3BR/2BA home offering modern design, open living space, indoor laundry, and a 2-car garage. A rare chance to own newer construction at an affordable price point. Ideal for first-time buyers or investors seeking strong long-term potential. Conveniently located near shopping, dining, and major roadways. Lender approval required.

4913 Jackson Street, Winter Haven

Courtesy of NONA LEGACY POWERED BY LA ROSA

$250,000
2 Beds ⋅ 2 Baths ⋅ S5141917 MLS
Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.

940 Oleander Drive Se, Winter Haven

Courtesy of JASON MITCHELL REAL ESTATE FLO

$290,000
4 Beds ⋅ 2 Baths ⋅ TB8464311 MLS
Welcome home to 525 Squires Grove Dr! This well-maintained property offers a great blend of comfort, space, and convenience. Enjoy an open layout with natural light, spacious living areas, and a functional floor plan ideal for everyday living and entertaining. The kitchen features ample cabinet and counter space with a layout that flows into the main living area. The primary suite is generously sized, with additional bedrooms that can be used for guests, an office, or flex space. Step outside to a patio—perfect for morning coffee or relaxing in the evening. Conveniently located near shopping, dining, major roadways, and everyday essentials including Publix. Schedule your private showing today!

525 Squires Grove Drive, Winter Haven

Courtesy of ALIGN RIGHT REALTY LLC

$452,000
3 Beds ⋅ 2 Baths ⋅ A4678252 MLS
Welcome to this beautifully upgraded 3-bedroom, 2-bath home offering 2,045 square feet of refined living space in the highly desirable Lake Ashton 55+ golf community—where luxury meets an active, resort-style lifestyle. This thoughtfully designed home features top-notch upgrades throughout, including an additional sliding glass door leading to the back patio, flooding the living space with natural light and creating a seamless indoor-outdoor living experience. The spacious kitchen is a standout, boasting abundant cabinet storage with extended cabinetry along the back wall, perfect for entertaining, organization, and everyday convenience. Smart hybrid water heater and water softener system as well The open and inviting floor plan provides generous living and dining areas, while the private primary suite offers comfort and tranquility. Two additional bedrooms are ideal for guests, hobbies, or a home office. Both bathrooms are well-appointed, and the home’s layout is designed for easy living. Located within Lake Ashton, residents enjoy world-class amenities including championship golf courses, clubhouses, fitness centers, pools, tennis and pickleball courts, planned activities, and a vibrant social calendar. Experience the best of Florida living in this exceptional home—schedule your private showing today and discover everything Lake Ashton has to offer.

6308 Pinehurst Loop, Winter Haven

Courtesy of FLATFEE.COM

$1,799,900
4 Beds ⋅ 4 Baths ⋅ L4958559 MLS
Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist. The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends luxury with everyday livability. Designed for both entertaining and comfortable living, the open-concept layout showcases luxury vinyl plank flooring throughout, expansive living areas, and a beautifully upgraded chef’s kitchen that serves as the heart of the home. With 4 bedrooms and 4 full bathrooms, the residence provides generous space for family and guests alike. Outdoors, a private pool invites relaxation while remaining surrounded by peaceful, natural views. Adding exceptional value and versatility, the property includes a 1,300 sq ft detached guest house featuring 2 bedrooms and 2 bathrooms, along with an upgraded kitchen and bath—ideal for extended family, long-term guests, or a private work-from-home or creative space. The land itself is what truly sets this property apart. The nearly 11-acre setting offers a thoughtful balance of open usable acreage, mature landscaping, and a scenic private pond, creating a sense of separation and tranquility that enhances both privacy and lifestyle. Multiple outbuildings, including a barn/garage and lean-to structure, provide ample room for storage, hobbies, equipment, or future expansion. In a market where acreage is disappearing and privacy is priceless, properties offering this scale of land, level of renovation, and proximity to town are exceptionally rare. This is not just a home—it’s a private retreat, a long-term asset, and an opportunity to own something truly irreplaceable.

13 Bogey Drive, Winter Haven

Courtesy of THE MARKET REALTY COMPANY

$309,999
3 Beds ⋅ 2 Baths ⋅ S5141435 MLS
Some homes are built. Others are crafted. Tucked away in a quiet Winter Haven neighborhood, 4599 Reynosa Drive is a rare, cedar-constructed residence that blends artisan craftsmanship with modern efficiency. From the moment you arrive, the home sets itself apart fully fenced with new vinyl fencing, enhanced exterior lighting, and a brand-new Trex front porch designed for relaxed mornings and long evenings. Inside, the warmth is immediate. Cedar wood wraps the interior, creating a natural, timeless atmosphere rarely found in Florida homes. The craftsmanship was completed by a skilled wood artisan, and the attention to detail is felt throughout custom wood features, soaring character, and a layout that feels both grounded and inviting. Tile flooring spans the entire downstairs, while all bathrooms are finished floor-to-ceiling in tile, offering durability and a clean, elevated aesthetic. The home has been thoughtfully upgraded for comfort and longevity, including brand-new hurricane-impact, double-pane windows with architectural tint reflecting up to 90% of heat, a new AC unit, new attic fan, insect-repellent insulation, and a fully sealed roof coated with heat-reflective, hurricane-rated paint. Even in peak summer, electric bills remain impressively low under $150 with no solar required. The kitchen and bathrooms feature newer plumbing, modern appliances (all just a few years old), and a standout stone-wrapped Jacuzzi tub, creating a spa-like retreat within the home. Side sliders bring in natural light and connect indoor living with outdoor space, while the garage includes sensor lighting, Hardie backer walls, full electrical, and AC, making it ideal for a workshop, studio, or flex space. The property is being offered fully furnished, including custom handcrafted wood furnishings (excluding beds and sofas), making it a true turnkey opportunity for a buyer who values character, quality, and immediate livability. Regular termite and pest control servicing adds peace of mind to this cedar-built, naturally insect-resistant home. Centrally located between Orlando and Tampa, with convenient access to major highways, shopping, and daily essentials, this home delivers both lifestyle and location. This is not a cookie-cutter property. This is a home with a story built to last, designed to feel different, and ready for its next chapter.

4599 Reynosa Drive Sw, Winter Haven

Courtesy of LPT REALTY, LLC

$399,900
3 Beds ⋅ 2 Baths ⋅ L4958336 MLS
Located in the desirable Gardens of Interlochen, this beautifully renovated and impeccably maintained 3-bedroom, 2-bath residence at 106 Jardin Lane offers thoughtful upgrades, timeless finishes, and a functional open layout designed for both everyday comfort and effortless entertaining. At the heart of the home is a stunning renovated kitchen featuring granite countertops, LG black stainless steel appliances including an induction range, a composite sink highlighted by a striking gold-tone faucet, an eat-in dinette, and a spacious closet pantry. Wood flooring flows throughout the main living areas and bedrooms, complemented by elegant crown molding, plantation shutters, and designer light fixtures that elevate each space. The well-designed floor plan includes a welcoming great room, a dedicated dining room, a split-bedroom layout for added privacy, a built-in bar ideal for entertaining, a laundry closet, screened lanai, and a meticulously maintained side-entry two-car garage. French doors open from the great room to the screened lanai, creating a seamless indoor-outdoor connection and an inviting space to enjoy morning coffee or relax with a good book. The primary suite serves as a true retreat, featuring a tray ceiling, an oversized walk-in closet with custom shelving and drawers, a large linen closet, and a beautifully renovated en-suite bath. The spa-inspired bathroom offers a generous walk-in shower with a bench, handrails, and handheld shower wand, dual vanities with granite countertops and a dedicated makeup area, along with new mirrors, faucets, lighting, and toilet. Both guest bedrooms feature wood flooring, ceiling fans, and closets with overhead storage. The updated guest bath includes a glass enclosed tub, linen storage, a granite topped vanity and pocket-door access to the third bedroom, making it an ideal secondary primary suite or private guest space. The interior laundry closet is equipped with a newer full size Speed Queen washer and dryer, as well as new cabinetry and a hanging rack. The side-entry two-car garage mirrors the care found throughout the home, featuring carpeted flooring, custom built-in cabinetry with countertop workspace, and convenient pull-down attic stairs—perfect for organized storage or hobbies. Set on a generous 0.25-acre lot, the property features an irrigation system with a timer and is shaded by beautiful, mature oak trees that create a peaceful and inviting setting. Lawn care, cable, internet and exterior house painting (every 10 years), are all included in the quarterly HOA fee, providing a low-maintenance lifestyle while the 2019 roof provides added peace of mind. Ideally located just minutes from shopping, dining, and medical facilities, and centrally positioned between Tampa and Orlando, this move-in-ready home offers style, comfort, abundant storage, and an exceptional location in the heart of Winter Haven.

106 Jardin Lane, Winter Haven

Courtesy of THE STONES REAL ESTATE FIRM

$105,000
2 Beds ⋅ 2 Baths ⋅ O6371915 MLS ⋅ 1700 BLDG.
55+ COMMUNITY IN WINTER HAVEN! CORNER UNIT WITH GREAT AMENITIES! Looking for easy, low-maintenance living in a 55+ community in Winter Haven? This spacious corner-unit condo offers comfort, convenience, and plenty of amenities. Inside, you’ll find a kitchen with granite countertops and marble flooring, plus wood laminate floors throughout the living room, dining area, and hallway. The convenient interior laundry area includes a washer and dryer, making everyday living a little easier. The primary bedroom opens to a screened-in balcony, creating a nice spot to enjoy your morning coffee or relax at the end of the day. The community offers plenty to keep you active and connected, including a large heated swimming pool, pickleball courts, shuffleboard, grilling area, and clubhouse with a fitness center. Additional features include elevator access, reserved covered parking, secure storage, and a common laundry area. Located in central Winter Haven, you’ll be close to downtown, shopping, restaurants, hospitals, and medical facilities. With convenient access to I-4, you’re also within easy reach of both Orlando and Tampa. If you’re looking for a 55+ condo in Winter Haven with resort-style amenities and a convenient location, this corner unit is worth a look!

1700 6th Street Nw Unit B24, Winter Haven

Courtesy of LPT REALTY, LLC

$293,990
3 Beds ⋅ 2 Baths ⋅ O6372244 MLS
Under Construction. The Allex is one of our one-story floorplans featured in our Harmony at Lake Eloise in Winter Haven, Florida. With 2 exteriors to choose from, the Allex is sure to turn heads. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,504 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. Relax on the covered lanai looking out to your backyard. The kitchen features granite countertops, stainless-steel appliances and a walk-in pantry which are sure to both turn heads and make meal prep easy. You’ll never be too far from the action with the living and dining area right there. In every bedroom you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom located in the rear of the home has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity. Like all homes in Harmony at Lake Eloise, the Allex includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Contact us today and find your home at Harmony at Lake Eloise. *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.*

3105 Firebrush Lane, Winter Haven

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$310,990
3 Beds ⋅ 2 Baths ⋅ O6372105 MLS
Under Construction. The Astor is one of our one-story floorplans featured in Harmony at Lake Eloise in Winter Haven, Florida. With 3 exteriors to choose from, the Astor is sure to turn heads. Inside this 3 bedroom, 2 bathroom home, you’ll find 1,565 square feet of comfortable living. This home offers a two-car garage and covered porch in the rear of the home. As you enter, you're greeted with a spacious living area, coat and linen storage closets and dedicated laundry room. The kitchen located in the center of the home features quartz countertops, an island, stainless steel appliances and a pantry. You’ll never be too far from the action with the living and dining area to the immediate left and right. The primary bedroom has an attached bathroom that features a walk-in closet, double sink vanity and all the space you need to get ready in the morning. Every bedroom features carpeted floors and a closet. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. Like all homes in Harmony at Lake Eloise, the Astor includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Contact us today and find your home at Harmony at Lake Eloise. *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.*

1726 Hummingbird Road, Winter Haven

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$250,000
3 Beds ⋅ 2 Baths ⋅ O6371966 MLS
Stop looking now!This well kept home is waiting just for you. A nice 3/2 with tile and laminate thorough. This home offers a beautiful back yard with a deck for a peaceful retreat for enjoyment of the lake.Price just reduced for quik sale. Schedule your showing now.

3723 Imperial Drive, Winter Haven

Courtesy of PROPERTY WAREHOUSES OF AMERICA

$325,000
5 Beds ⋅ 3 Baths ⋅ L4958266 MLS
Short Sale. This charming home is a diamond in the rough, waiting for the right owner to unlock its full potential. Located in a sought-after neighborhood of picturesque red brick homes, this property offers a unique opportunity for those with vision and ambition. This home is being sold as a short sale, making it an ideal project for those looking to invest in a renovation loan and transform it into one of the best investments on the street. Surrounded by beautiful homes with strong property values, this two-level home boasts 5 bedrooms (with potential for a 6th), three bathrooms, and 2579 square feet of living space. Inside, you'll find real hardwood floors, double-paned windows, a cozy wood-burning fireplace, and a double car garage, all situated on a spacious 0.32-acre lot. With a little TLC and creativity, this property has the potential to become a stunning showcase home that stands out in the neighborhood. Don't miss this opportunity to own a piece of Winter Haven's red brick charm and create the home of your dreams. Schedule a showing today and start envisioning the possibilities that await.

129 Lake Otis Road Se, Winter Haven

Courtesy of COLDWELL BANKER REALTY

$65,000
1 Beds ⋅ 1 Baths ⋅ S5141094 MLS ⋅ Granada BLDG.
Owner motivated and ready to negotiate — WOW! This BEAUTIFUL 931 SF 1BR/1BA FIRST-FLOOR condo in Orchid Springs offers stunning lagoon views! Located in the 55+ Granada Building, where at least one occupant must be 55+. IMMEDIATELY AVAILABLE and MOVE-IN READY! Step into an open, airy floor plan with tile throughout, creating a bright and spacious feel. The dining area, living room, and bonus room flow seamlessly together, all overlooking the tranquil lagoon. As an end unit, the living room and bedroom enjoy extra windows with peaceful courtyard views. The bedroom features a walk-in closet plus an additional hallway closet, providing excellent storage. The bathroom includes a custom vanity and a tub/shower combo. A washer and dryer are included, offering added convenience. Additional highlights include assigned parking directly in front of the unit. Perfect for year-round living or a seasonal retreat in a serene, well-maintained community.

100 El Camino Drive Unit 111, Winter Haven

Courtesy of LPT REALTY, LLC

$334,800
3 Beds ⋅ 2 Baths ⋅ P4937386 MLS
Virtually Staged. Welcome Home!!! Recent Price Reduction! 4577 Back Nine Dr. Winter Haven, Fl. features 3 bedrooms and 2 full baths and is located in Lake Ashton, an Exclusive Florida Retirement 55+ community. This home has BRAND NEW EXTERIOR PAINT! The widened, paver driveway offers extra room for parking and the screened entry at the front door is an added bonus. The glass leaded front door with large eye brow window above leads you into a home that is warm, inviting and spacious. The open-concept kitchen showcases granite countertops, stainless steel appliances, Maple cabinets and a Pantry Cabinet with convenient pull-out shelving. You can seamlessly blend indoor and outdoor living by sliding open the living room and dinette area sliding glass doors to the screened, covered lanai with 8" aluminum border base. It's the perfect place for entertaining. The primary bedroom with En-Suite bath has been extended 4 ft. to provide additional living space. It's the perfect getaway and you'll enjoy the EXTRA SPACE in the primary suite. The primary bathroom has ample closet space with His/Her Walk In Closets with Organization System, a large walk in shower with double shower heads, a separate water closet and separate His and Her Vanities. Her vanity has an additional make up area. Guests will appreciate the separate bedrooms and bath behind a pocket door. Additional features include: an automatic screen on the garage door, a separate irrigation meter, 18" diagonal tile in home (Bed 2 and Bed 3 are excluded), crown moulding, New A/C modulator, cabinetry in laundry room, Plantation Shutters in the Bedrooms, Upgraded entry light fixture, surround sound in the living room, additional insulation in the attic, new interior paint in Bedroom 1 and Guest Bathroom, new interior paint in the formal dining and dinette areas. Lake Ashton, a Florida Retirement community, has a Clubhouse with large grand ballroom, Outdoor Community Heated Pool, Tennis Courts, Bocce Ball, Shuffleboard, Fitness Center, Movie Theater, Bowling Lanes, Restaurant (Charm City)and More! The Health and Fitness center has indoor basketball, indoor racquetball, indoor heated pool, pickle ball and tennis courts, media center, card, craft and billiard rooms. There are two golf courses located in Lake Ashton. Memberships are optional and not a requirement to reside in Lake Ashton. Residents enjoy the resort style amenities and activities offered in Lake Ashton, a premier Florida Retirement Community. Don't miss this opportunity to own your piece of paradise. Check out the photo gallery and make your appointment to tour this home.

4577 Back Nine Drive, Winter Haven

Courtesy of LAKE ASHTON REALTY INC.

$298,000
3 Beds ⋅ 2 Baths ⋅ L4957933 MLS
Welcome to your dream home, a charming 2-bedroom, 2-bath retreat with a versatile bonus room that can be used as a 3rd bedroom or a separate home office featuring its own private exterior entrance! This inviting home has been thoughtfully refreshed and is move-in ready, offering fresh interior paint, a new smart thermostat, recent tree removal, and a brand-new shingle roof (03/24) for peace of mind! Inside, you’ll find a spacious kitchen with a breakfast bar that opens to a bright living room, ideal for everyday living and entertaining. The large dining room or secondary family room is conveniently located next to the kitchen and provides plenty of space for gatherings. Relax in the cozy Florida room, featuring warm wood walls and ceilings and an abundance of windows where you can enjoy views of Lake Elbert! Outside you will find your large paver patio, perfect for entertaining or unwinding, and enjoy the privacy of a newly built fully fenced backyard. Additional updates include a new AC (2022), blown attic insulation (2022), water heater (2019), all kitchen appliances (2021), and Exterior Front Porch paint along with a new front door (2025). Conveniently located just minutes from Downtown Winter Haven, Polk State College, HWY 27, and medical facilities, this home blends comfort, flexibility, and an excellent location. Schedule your showing today!

1301 Evalyn Drive Se, Winter Haven

Courtesy of LIVE FLORIDA REALTY

$304,016
3 Beds ⋅ 2 Baths ⋅ R4910460 MLS
Crescent Pointe is a brand new community located in Winter Haven, FL, conveniently situated off State Rd 653 and boasting easy access to a range of nearby attractions. For residents who enjoy outdoor activities, the Winter Haven Chain of Lakes is nearby. It offers opportunities for boating, fishing, and other recreational activities. The community is also close to the bustling downtown area, where residents can explore local shops, dining venues, and family events. With NO CDD and low HOA, Crescent Pointe is an ideal place to call home in Winter Haven.

951 Lunar Lane, Winter Haven

Courtesy of VANTAGE PROPERTY MANAGEMENT LLC

$249,000
3 Beds ⋅ 2 Baths ⋅ P4937345 MLS
Under contract-accepting backup offers. Experience resort-style living in the prestigious gated community of Winterset, just minutes from Legoland. This captivating 3-bedroom, 2-bath villa, featuring Mediterranean-inspired architecture, offers the perfect blend of elegance, comfort, and tranquility. Upon arrival, you’re welcomed by a charming covered screened porch accented with a leaded glass entry door, setting the tone for the inviting interior. The thoughtfully designed split-bedroom floor plan includes a spacious great room highlighted by a wood-burning fireplace, a decorative built-in media center, and glass sliders that open to the Florida room—seamlessly blending indoor and outdoor living. Easy-to-maintain solid surface flooring flows throughout the home. The well-appointed kitchen showcases white cabinetry with crown molding, an upgraded stainless steel appliance package including a gas range and beverage cooler. Granite countertops that adorn the expansive breakfast bar and a double-bowl sink with a gooseneck faucet adds both style and functionality. The open-concept layout is ideal for entertaining, with the formal dining room flowing effortlessly into the living area. The primary bedroom suite serves as a luxurious retreat, featuring laminate flooring, a spacious walk-in closet, and a glass slider providing private access to the Florida room. The primary bathroom offers a granite-topped vanity, upgraded brushed nickel fixtures, a comfort-height toilet, and a tub/shower combination with a decorative tile surround. Both guest bedrooms are generously sized and include walk-in closets, providing ample storage. Outdoor living is elevated with an extended Florida room offering peaceful pond views—an ideal space to relax and unwind. Additional Features: Laundry room with washer and dryer, New ceiling fans throughout with remote controls, new water heater, Updated AC system (2021), Epoxy-finished flooring in the Florida room and garage, Exterior carriage lighting, Gutters, Tile roof, One-car garage with garage door opener. The Winterset community offers an exceptional array of amenities, including a lakefront clubhouse, tennis courts, shuffleboard, a heated pool, hot tub, and access to Lake Winterset, part of the renowned Winter Haven Chain of Lakes. HOA fees include exterior maintenance, grounds maintenance, security, and access to community amenities, ensuring truly carefree living. Conveniently located near shopping, dining, medical facilities, and entertainment, this villa provides a lifestyle defined by luxury, comfort, and convenience.

2202 Garden Lake Drive, Winter Haven

Courtesy of CENTURY 21 MYERS REALTY LAKE WALES

$439,000
4 Beds ⋅ 3 Baths ⋅ L4958092 MLS
Under contract-accepting backup offers. Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.

240 Santa Rosa Drive, Winter Haven

Courtesy of LIVE FLORIDA REALTY

$275,900
3 Beds ⋅ 2 Baths ⋅ O6369098 MLS
Under Construction. The Archer II is one of our one-story floorplans features in our Willowbrook South community in Winter Haven, Florida. Take your pick between two sleek exterior options when choosing this floorplan. Inside this 3 bedroom, 2 bathroom home you’ll find 1,328 square feet of comfortable living. The open concept layout allows for seamless movement between spaces making entertaining guests a breeze. It also provides homeowners versatile design options. The kitchen features shaker-style cabinets, quartz countertops, and stainless steel appliances, which are sure to both turn heads and make meal prep easy. You’ll bever be too far from the action with the living and dining area right there. In every bedroom, besides the primary bedroom, you’ll have carpeted floors and a closet in each room. Whether these rooms become bedrooms, office spaces, or other bonus rooms, there is sure to be comfort. The primary bedroom features luxury vinyl plank flooring that will be sure to stand out. It also has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Sharing a sink isn’t a worry with the double vanity, and you also get additional privacy with a separate door for the toilet and shower. Contact us today and find your home at Willowbrook South. *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.*

2799 Adeline Avenue, Winter Haven

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$284,500
3 Beds ⋅ 2 Baths ⋅ P4937324 MLS
Discover the perfect blend of comfort, elegance, and low-maintenance living in this beautifully maintained 3-bedroom, 2-bath home, ideally situated in the highly sought-after 55+ gated community of Traditions at Lake Ruby. Thoughtfully designed with both style and functionality in mind, this residence offers the ideal setting for a relaxed Florida lifestyle. A spacious covered front entry welcomes you inside through a beautiful leaded glass front door with a transom window, creating a warm and inviting first impression. The bright eat-in kitchen is appointed with 42-inch maple wood cabinetry, Corian countertops, a closet pantry, breakfast bar, and a sunny breakfast nook—perfect for casual dining or entertaining family and friends. The expansive great room features triple sliding glass doors that open to an oversized screened lanai, creating a seamless transition between indoor and outdoor living. The open floor plan also includes formal living and dining rooms enhanced by soaring ceilings and decorative architectural niches that add character and sophistication. The spacious primary suite is a private retreat, complete with a cozy sitting area offering direct lanai access and two generous walk-in closets with convenient overhead luggage shelving. The luxurious en-suite bath features a comfort-height dual-sink vanity, linen closet, seated walk-in shower, private water closet, and a relaxing garden tub. Step outside to the oversized screened lanai, where you'll find the perfect place to enjoy your morning coffee, entertain guests, or simply relax while taking in Florida's beautiful weather. Additional highlights include an interior laundry room with washer, dryer, and utility sink; Honeywell thermostat and humidistat; architectural shingle roof (2020); transferable termite bond; paver driveway and walkway; gutters; floodlights and carriage lighting; and a spacious two-car garage with automatic door opener. Living in Traditions at Lake Ruby means enjoying an exceptional resort-style lifestyle. Residents have access to a stunning lakefront clubhouse, private dock and boat ramp, heated swimming pool and spa, ballroom, billiards room, library, computer room, craft room, fitness center, aerobics studio, tennis and pickleball courts, basketball, bocce ball, shuffleboard, dog park, and an active calendar of social events and activities. Conveniently located near shopping, restaurants, major highways, and LEGOLAND®, this exceptional home offers both tranquility and accessibility. Best of all, the monthly HOA fee includes exterior house painting, lawn maintenance, cable, internet, and full access to the community's outstanding amenities, allowing you to enjoy truly carefree living.

2925 Dayton Drive, Winter Haven

Courtesy of CENTURY 21 MYERS REALTY LAKE WALES

$112,000
2 Beds ⋅ 2 Baths ⋅ L4957905 MLS ⋅ 8 BLDG.
Whether you are looking for your first home or first rental property, this condominium is a must see! Ideally located off of Overlook Drive in Winter Haven, minutes form Legoland, downtown Winter Haven, and the Chain of Lakes. This unit features an updated kitchen with an upgraded stainless steel gas stove, stainless steel dish washer, and a one-year-old refrigerator. Additionally, there are newer dual pane windows, tile throughout the living area, and vinyl plank floors in the bedrooms! The air conditioner is only two years old and has a warranty that expires in 2033 and the washer/dryer is only one year old. The interior walls were just painted and this unit is ready for a new owner or tenant! This is one of the nicest units in the complex! Call today to schedule a showing!

831 Orchid Springs Drive Unit #831, Winter Haven

Courtesy of CLARK REALTY LLC

$288,900
4 Beds ⋅ 2 Baths ⋅ O6366024 MLS
This BEATIFUL HARPER Model home is located in the quaint town of Winter Haven. Ski capital & home of LEGOLAND. The NEWLY UPDATED HARPER has 4 bedrooms, 2baths & a 2-car garage - 1665 SqFt. This new model has an open floor plan with a spacious GREAT room off the kitchen to entertain & enjoy the company of your guests. You will love the split floor plan with beautiful & spacious master suite with walk in closet & en suite bathroom away from the other 3 bedrooms. Home comes with WHIRLPOOL Stainless Appliances- range, hood microwave, refrigerator & dishwasher. Home also comes with faux wood blinds throughout & has Smart Home Technology which allows you to set the scene & connect to your home with your voice, from your smart phone. *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.*

4160 Giorgio Drive, Winter Haven

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$301,900
5 Beds ⋅ 2 Baths ⋅ O6367889 MLS
Under Construction. Welcome to the Dundee, one of our one-story floorplans available in the beautiful community of Willowbrook South in Winter Haven, Florida. Choose between three thoughtfully designed exterior styles. This spacious 5-bedroom, 2-bathroom home offers 1,708 square feet of modern, comfortable living. Step inside to an inviting open-concept layout where the kitchen, living, and dining areas flow seamlessly together perfect for both everyday living and entertaining guests. The gourmet kitchen is the heart of the home, featuring sleek stainless-steel appliances, quartz countertops, and contemporary cabinetry that combine style with functionality. Overlooking the dining and living room, the kitchen ensures you’re always connected to the action. Luxury finishes are found throughout, with luxury vinyl plank flooring in the main living areas, primary suite, bathrooms, laundry room, and foyer. Bedrooms 2–5 include soft carpet and roomy closets, offering comfort and flexibility to use as bedrooms, office space, or creative bonus rooms. The private primary suite is designed for relaxation, with a walk-in closet and an en-suite bathroom that includes a toilet and shower for added privacy. This move-in ready home in Willowbrook South, Florida offers the perfect balance of style, comfort, and convenience. *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.*

2795 Adeline Avenue, Winter Haven

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$335,000
2 Beds ⋅ 2 Baths ⋅ P4937220 MLS
Don't miss out on this opportunity to reside in a home located on the WEST golf course in Lake Ashton. FURNITURE AVAILABLE! GOLF CART INCLUDED! WASHER/DRYER INCLUDED! This Callaway Floor plan with NEW A/C (December 2025) is a "Green" home with 2 Bedrooms, 2 Baths, Plus a FLEX ROOM. This home has over 1,660 sq. ft. of living space. Located on the 17th Fairway of the West Golf Course in Lake Ashton, a guard-gated Florida 55+ community, this home offers a Split Plan. The kitchen package features a spacious dinette area, granite counter tops, stainless steel appliances, 42" cabinets and breakfast bar. The foyer with high ceiling is welcoming and is a passage to the laundry room and 2nd bedroom. The laundry room is directly to your left and to your right is a hallway with 2 linen closets that leads to the 2nd bedroom and Guest Bath. The laundry room is accessible from the foyer and the garage. The living room, kitchen and dinette are centrally located in this home- OPEN & SPACIOUS. The Den/Office is directly off the living room and is currently being used as a bedroom. There are triple sliders in the living room that separate the screened and covered lanai with tile floor. The primary suite with large walk in closet includes a master bath with dual sinks and a comfort height vanity, walk in shower and separate water closet with window. Other upgrades in this home include tile flooring in the Living Areas (Bedrooms are carpeted), water softener, ceiling fans, screened entryway, automatic screen on the garage door. Lake Ashton offers a Main Clubhouse with a theater, bowling lanes, card, craft and billiard rooms, fitness center, restaurant (Charm City), and outdoor heated pool. Residents also enjoy tennis courts, shuffleboard courts, Bocce and planned activities in the community. There is a Health and Fitness Center with an indoor heated lap pool, 1/2 basketball, indoor racquetball, pickle ball courts and MORE... Make an appointment to tour this home and Lake Ashton TODAY!

5197 Pebble Beach Boulevard, Winter Haven

Courtesy of LAKE ASHTON REALTY INC.

$269,000
3 Beds ⋅ 2 Baths ⋅ G5105497 MLS
Short Sale. Built in 2020, this well-designed 3-bedroom, 2-bathroom home offers 1,688 square feet of living space, an attached 2-car garage, and a desirable corner lot with a private vinyl-fenced side and backyard. Step inside to an inviting floor plan featuring hard-surface flooring throughout most of the home and a spacious living area ideal for everyday living and entertaining. The kitchen features granite countertops, rich brown cabinetry, ample counter and storage space, and an eat-in dining area, creating a comfortable central gathering space. The primary suite offers privacy, a walk-in closet and its own full bathroom, while two additional bedrooms provide flexibility for guests, an office or additional living space. A dedicated laundry room adds everyday convenience. Sliding glass doors lead to the covered rear lanai and fenced backyard, providing additional outdoor living space for relaxing, grilling or entertaining. The corner homesite offers additional separation from neighboring properties, while mature landscaping, an irrigation system and sidewalks enhance the exterior. Kensington View offers sidewalks, street lighting, open green spaces and a community playground, and its location provides convenient access to US Highway 17 and the Polk Parkway, making travel throughout Polk County and toward Lakeland, Orlando and Tampa convenient. Enjoy being approximately 20 minutes from LEGOLAND® Florida Resort, home to the LEGOLAND theme park, Water Park, SEA LIFE Florida Aquarium and additional attractions. Winter Haven is also known for its Chain of Lakes, boating and recreation, while nearby Cypress Gardens Boulevard offers numerous restaurants, shopping and everyday services. For commuters and travelers, the Lakeland area is approximately 15 miles away, and Lakeland Linder International Airport is approximately 14 miles from Kensington View. The home's Central Florida location provides access to the employment, dining and entertainment options of Lakeland while keeping Winter Haven's shopping, recreation and attractions close to home. With newer construction, a fenced corner lot, covered outdoor living space and a convenient location between Winter Haven and Lakeland, 440 Kensington View Drive offers an excellent combination of comfort, location and accessibility. I would use this version over the old MLS remarks because it does a much better job of selling the location, especially the 20-minute LEGOLAND proximity, Lakeland access, US-17/Polk Parkway connectivity, and Winter Haven recreation.

440 Kensington View Drive, Winter Haven

Courtesy of PREFERRED RE BROKERS III

$265,000
3 Beds ⋅ 1 Baths ⋅ A4674941 MLS
This move-in ready 3-bedroom Winter Haven pool home offers a fantastic combination of comfort, upgrades, and true Florida living on an oversized lot with no HOA. The home features a brand-new roof, new HVAC system and thermostat, new water heater, new pool pump and chlorinator, new laundry units, new exterior front doors, and an expanded driveway with ample parking. Inside, you’ll find a functional layout with generous living space and fresh improvements throughout. The private in-ground pool creates a relaxing backyard setting, while the large lot provides room for outdoor entertaining, storage, or future additions. Located minutes from the Winter Haven Chain of Lakes, Gene’s Lakeside Marina, LEGOLAND Florida Resort, golf courses, shopping, dining, and local parks, this property sits in one of Central Florida’s most desirable and fast-growing areas. With major updates already completed and convenient access to boating, recreation, and upcoming community development, this home is an excellent opportunity for first-time buyers, families, or investors.

3022 Hickory Street Nw, Winter Haven

Courtesy of THE URBAN GROUP, INC.

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