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VILLAMAR PH 3 - P4938873 - 2108 CARTGATE LN, WINTER HAVEN, FL 33884 Just Added on 05/29/2026 7:50PM
$310,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable Winter Haven area! This move-in ready property offers a perfect blend of comfort, style, and modern updates throughout. From the moment you step inside, you’ll notice the upgraded accent wall paneling featured in the foyer, dining room, and spacious primary bedroom, adding warmth and custom character to the home. The dining room and foyer have also been enhanced with updated light fixtures that provide a fresh, elegant touch. Pride of ownership is evident throughout, as this home has been exceptionally well maintained and cared for. With inviting living spaces, a functional layout, and tasteful upgrades, this home is ideal for both relaxing and entertaining. Conveniently located near shopping, dining, schools, and major roadways, this property combines comfort and convenience in one attractive package. Don’t miss your opportunity to own this charming Winter Haven home — schedule your private showing today!
Listing is courtesy of: DALTON WADE INC
COUNTRY WALK/WINTER WINTER HAV - S5150893 - 3268 COUNTRY WALK CLUB CIR, WINTER HAVEN, FL 33881 Just Added on 05/29/2026 6:53PM
$300,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Experience elevated living in this beautifully maintained 3 bedroom, 2 bathroom residence located in the highly desirable Country Walk community in Winter Haven. Designed with style and comfort in mind, this home showcases custom luxury finishes throughout the living room and bedrooms, creating an elegant and inviting atmosphere. The open concept layout offers the perfect blend of functionality and sophistication, while the modern kitchen serves as the centerpiece of the home with sleek cabinetry, quartz countertops, and ample space for cooking and entertaining. The spacious primary suite provides a private retreat with a walk in closet and a beautifully appointed bathroom. Step outside and enjoy the extended paver patio, an ideal space for relaxing or hosting family and friends, all enclosed by a white PVC privacy fence that enhances both comfort and privacy. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this home is also just minutes from LEGOLAND Florida Resort and many of Central Florida’s most popular attractions. Combining stylish interior design, exceptional outdoor living, and a prime location, this residence offers an outstanding opportunity to enjoy the best of the Florida lifestyle.
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY
PINNACLE POINT - TB8512920 - 1396 AXEL CIR, WINTER HAVEN, FL 33880 Just Added on 05/29/2026 6:09PM
$400,000 | Single Family Home | 5 beds | 3.0 baths | 2 gar
One or more photo(s) has been virtually staged. Welcome to this beautifully updated, 5-bedroom, 3-bath home built in 2022, located in the sought-after Pinnacle Point community of Winter Haven. This home offers a spacious open floor plan filled with natural light and designed for comfortable everyday living. The kitchen features sleek finishes, modern appliances, and a large island that opens seamlessly to the main living and dining areas, making it ideal for both daily life and entertaining. The downstairs includes a bonus room, a full guest bathroom, and a guest bedroom, adding excellent flexibility for visitors or multi-generational living. Upstairs, a versatile loft provides additional living space perfect for a media room, office, or play area. The primary suite offers a private retreat with a large walk-in closet and a well-appointed bathroom, while the additional bedrooms provide plenty of space and versatility. The home features durable vinyl flooring throughout with no carpet,Welcome to this beautifully updated 5-bedroom, 3-bath home in the sought-after Pinnacle Point community of Winter Haven. This home offers a spacious open floor plan filled with natural light and designed for comfortable everyday living. The kitchen features sleek countertops, modern appliances, and a large island that opens seamlessly to the main living and dining areas, making it ideal for both daily life and entertaining. Upstairs, a versatile loft provides additional living space for a media room, office, or play area. The primary suite offers a private retreat with a large walk-in closet and well-appointed bath, while the additional bedrooms provide plenty of space and flexibility. The home features durable vinyl flooring throughout with no carpet, adding to its clean and low-maintenance feel. Step outside to a generously sized backyard, perfect for outdoor gatherings, pets, or relaxing evenings under the Florida sky, with a soon-to-be fully fenced setup adding even more privacy and usability. Located close to LEGOLAND Florida Resort, shopping, dining, and medical facilities, and conveniently positioned between Tampa and Orlando, this home offers both comfort and convenience in a growing Central Florida location.
Listing is courtesy of: ROBERT SLACK LLC
STONEBRIDGE - L4962289 - 2115 KINGS XING SW, WINTER HAVEN, FL 33880 Just Added on 05/29/2026 4:59PM
$234,900 | Single Family Home | 2 beds | 2.0 baths | 1 gar
~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. 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.
Listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM
LAKE ASHTON WEST PH 01 - O6411968 - 5312 NICKLAUS DR, WINTER HAVEN, FL 33884 Just Added on 05/29/2026 4:03PM
$334,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE
CHESTNUT CRK - O6412012 - 1061 SANDPIPER LOOP, WINTER HAVEN, FL 33881 Just Added on 05/29/2026 2:48PM
$485,000 | Single Family Home | 5 beds | 3.0 baths | 3 gar
Fall in love with this stunning 5-bedroom, 3-bath home with a 3-car garage, perfectly situated on one of the largest lots in the neighborhood. Combining luxury, comfort, and functionality, this spacious home offers an open-concept layout with split bedrooms for added privacy, creating the perfect balance of space and efficiency. The heart of the home is a bright, wide-open living area flowing into a stunning gourmet kitchen featuring a massive island, 42-inch upper cabinets, a large pantry, and top-of-the-line stainless steel appliances. Whether you’re relaxing, entertaining, or cooking, this home offers endless space to move and gather. High-end finishes are showcased throughout, including quartz countertops in the kitchen, luxury tile flooring in the main living areas, premium carpeting in the bedrooms, crown molding, and elegant window shutters. This is more than just a home, it’s an investment, with over $60,000 in upgrades available for review. For added comfort and convenience, the home includes a water softener system and reverse osmosis filtration. Step outside to your private outdoor retreat featuring an oversized screened-in lanai, summer kitchen, and a fully fenced backyard on an expansive lot, perfect for enjoying the Florida lifestyle year-round. Located in a quiet, peaceful Polk County community near Highway 27, you are just a short drive to Disney, Orlando International Airport, shopping, dining, and more. Best of all, there are NO CDD fees and a low HOA. This home is being sold AS IS and is truly move-in ready. Schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC
STONEBRIDGE PH 02 - O6410748 - 2026 KINGS XING SW, WINTER HAVEN, FL 33880 Just Added on 05/29/2026 2:17PM
$235,000 | Single Family Home | 2 beds | 2.0 baths | 1 gar
WELCOME HOME TO STONEBRIDGE! WHERE COMFORT, STYLE, AND CONVENIENCE COME TOGETHER! Step through the custom gated courtyard and discover this beautifully updated residence that is truly move-in ready. From the moment you enter, you'll be impressed by the gorgeous porcelain tile flooring that flows throughout the main living areas, creating an elegant and welcoming atmosphere. The spacious Great Room serves as the heart of the home, featuring a stunning wood-paneled fireplace that creates a warm focal point for relaxing or entertaining. Newer(2022) Sliding Doors lead to a private covered and screened patio, offering the perfect place to enjoy your morning coffee, unwind after a long day or entertain guests in a peaceful outdoor setting. Adjacent to the Great Room is a dedicated dining area with a convenient pass thru to the kitchen. The beautifully updated kitchen showcases rich cabinetry, granite countertops, stainless steel appliances, and a breakfast nook, perfect for preparing meals and gathering with family and friends. Enjoy the convenience of the sliding doors out to the private courtyard. Retreat to the spacious primary suite, complete with a walk-in closet and an updated ensuite bath featuring a walk-in shower and modern finishes. The guest bedroom offers generous closet space and flexibility for visitors, a home office, or craft room. The beautifully renovated guest bathroom features a striking designer tile accent wall, creating a stylish, sophisticated space for family and guests. Additional highlights include a NEW ROOF (2024), NEW GUTTERS/DOWNSPOUTS ( 2026), NEW ELECTRIC PANEL (2024), NEWER WINDOWS AND SLIDERS (2022), updated bathrooms, washer and dryer, one-car garage, neutral décor throughout, and move-in-ready condition. Outside, enjoy both the private courtyard and the covered screened patio, offering multiple outdoor living spaces rarely found at this price point. Residents of Stonebridge enjoy access to a community pool and a convenient location close to shopping, restaurants, churches, medical facilities, and everyday conveniences. Located in the heart of Winter Haven, known as Florida's Chain of Lakes City, residents enjoy boating, fishing, waterfront dining, golf courses, beautiful parks, and year-round recreation. Winter Haven is also home to LEGOLAND Florida Resort and offers convenient access to both Orlando and Tampa, making it an ideal location for full-time residents, seasonal homeowners, or anyone seeking the Florida lifestyle. Hurry, schedule an appointment today to view this fabulous patio home.
Listing is courtesy of: COLDWELL BANKER REALTY
VILLAMAR PH 6 & PH 6D - P4938826 - 4519 RAPALLO AVE, WINTER HAVEN, FL 33884 Just Added on 05/29/2026 1:42PM
$339,900 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Welcome home to this beautifully designed 4-bedroom, 2.5-bath residence nestled on a desirable corner lot in the heart of Central Florida! From the moment you step inside, you’ll love the bright and open feel, complemented by stylish luxury vinyl plank flooring throughout the main living areas. The spacious kitchen is truly the heart of the home, featuring a large center island perfect for entertaining, meal prep, or gathering with family and friends, along with an oversized walk-in pantry offering an incredible amount of storage. The open-concept layout flows seamlessly into the living and dining spaces, creating an inviting atmosphere for both everyday living and hosting guests. Designed with functionality in mind, this home features a convenient guest half bath, while the secondary bedrooms are connected by a thoughtfully designed Jack-and-Jill bathroom layout. Step outside to enjoy the covered lanai and partially fenced backyard, creating a private space to relax and enjoy Florida living. The corner lot adds extra curb appeal and a welcoming presence within the community. Located in a sought-after community with a resort-style pool and fantastic amenities, this home combines comfort, style, and convenience all in one. With easy access to shopping, dining, attractions, and everything Central Florida has to offer, this one checks all the boxes!
PINNACLE POINT - TB8513583 - 1452 AXEL CIR, WINTER HAVEN, FL 33880 Just Added on 05/29/2026 12:47PM
$296,500 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Come check out this like-new 4-bedroom, 2-bathroom home with unbeatable value, priced to sell under $300k! If that's not enough, this newer community has absolutely NO CDD fees and a very low HOA, making this a great starter or investment home. Get instant equity on day one! Watch gorgeous sunsets over the water right from your private, covered lanai, and fully Fenced back yard with a high-quality, durable metal fence. Inside, this meticulously maintained home features the highly sought-after open-concept Valeria floor plan, complete with a spacious 2-car garage, contemporary kitchen finishes, sleek solid-surface quartz countertops, and included appliances. The large primary suite is tucked away for ultimate quiet, featuring an oversized walk-in closet and a dual-vanity bath. Located in a pristine, quiet community just minutes from Legoland, top schools, and major roadways. Turn-key, and priced for an immediate sale—schedule your private tour today.
Listing is courtesy of: MARK SPAIN REAL ESTATE
HIGH POINT - O6411867 - 2107 HIGH POINT AVE SW, WINTER HAVEN, FL 33880 Just Added on 05/29/2026 12:45PM
$180,000 | Single Family Home | 3 beds | 1.0 baths | 4 car
POOL HOME ON AN OVERSIZED CORNER LOT WITH A SCREENED LANAI, DETACHED SHE SHED/MAN CAVE, TWO CARPORTS, AND A FULLY FENCED BACKYARD! Tucked beneath mature shade trees in Winter Haven's established High Point community, this well-maintained home offers the space, flexibility, and outdoor living opportunities that many buyers have been searching for. From the inviting covered front porch to the multiple outdoor gathering areas, every part of this property is designed to be enjoyed. Step inside to a bright and welcoming interior where natural light fills the living spaces and creates a comfortable atmosphere throughout. The living room serves as the heart of the home and flows effortlessly into the dining area and kitchen, creating a layout that feels connected and functional for both everyday living and entertaining. The kitchen features ample cabinetry, generous countertop space, stainless steel appliances, breakfast bar seating, and easy access to the home's outdoor living areas. The home offers three comfortable bedrooms, each providing flexibility for family, guests, hobbies, or a home office. The centrally located bathroom features a dual-sink vanity with ample storage and countertop space. An indoor laundry room adds everyday convenience, and an additional flexible room currently used for storage offers opportunities for future use based on your needs. One of the home's standout features is the expansive screened lanai stretching across the rear of the property. This impressive outdoor living space creates the perfect setting for morning coffee, outdoor dining, game days, or relaxing evenings while enjoying Florida's beautiful weather. Beyond the lanai, the fully fenced backyard offers multiple areas to gather, entertain, and unwind. The above-ground pool creates a refreshing backyard retreat surrounded by mature landscaping and outdoor living spaces. A detached 12x20 she shed/man cave provides exceptional flexibility and can easily be utilized as a hobby room, creative studio, fitness space, game room, workshop, or private retreat. The property also features two separate carports, providing covered parking and additional space for vehicles, equipment, projects, and everyday convenience. The oversized corner lot offers additional outdoor space and versatility rarely found in many homes of this size. Whether you're hosting family gatherings, working on hobbies, gardening, relaxing by the pool, or simply enjoying the shade of the mature trees, this property provides room to live, work, and play. Conveniently located near shopping, dining, parks, schools, medical facilities, Winter Haven's renowned Chain of Lakes, Legoland Florida Resort, downtown Winter Haven, and major roadways connecting throughout Central Florida, this home offers convenient access to everyday essentials and local recreation. If you've been searching for a property that offers more than just a house—a place with room to gather, relax, create, and enjoy the Florida lifestyle—this home is ready to welcome its next owner.
Listing is courtesy of: KELLER WILLIAMS CLASSIC
VILLAMAR PH 6 & PH 6D - O6411460 - 3408 COSTELLO CIR, WINTER HAVEN, FL 33884 Just Added on 05/29/2026 11:29AM
$324,900 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Move-in ready 4-bedroom, 2-bathroom home, you'll find 1,760 square fee of comfortable living. A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting quartz countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms are flexible for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper 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. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Priced to Sell !!
Listing is courtesy of: BEACH REALTORS
CYPRESS PLANTATIONS - P4938830 - 2954 PLANTATION RD, WINTER HAVEN, FL 33884 1 Day on yellowkey
$744,900 | Single Family Home | 5 beds | 4.5 baths | 3 gar
PRICED BELOW RECENT APPRAISED VALUE OF $795,000 — APPRAISAL AVAILABLE FOR REVIEW! (Real Matterport Tour & Videos in Virtual Tour Links) Rare opportunity to own one of the most desirable waterfront golf course homes in Cypresswood Golf & Country Club. Positioned on a private corner lot overlooking the pond, 4th green, and 5th tee, this extensively updated 5-bedroom, 4.5-bath estate offers nearly 4,200 SQ FT of luxury living with breathtaking views, incredible sunsets, and no rear neighbors. Inside, soaring ceilings, engineered hardwood floors, custom finishes, a gas fireplace, expansive entertaining spaces, and a completely secret hidden room create a one-of-a-kind luxury experience unlike anything else on the market. The chef’s kitchen features stainless LG appliances, propane gas range, custom cabinetry, oversized island, and seamless flow into the family room and entertainer’s wet bar — all designed around the stunning golf and water views. The downstairs owner’s suite offers a private retreat with spa-style bath, oversized closet, and direct pool views, while upstairs features spacious guest suites and a dedicated movie room/loft ideal for entertaining, working from home, or multigenerational living. The screened outdoor living area feels like a private resort with a sparkling pool, newer gas heater, outdoor summer kitchen with gas grill, and peaceful panoramic golf course and waterfront scenery. Major upgrades include new downstairs HVAC (2025), updated engineered hardwood flooring, newer pool equipment and pump, tankless gas water heaters, roof updates and annual inspections, fresh interior paint, and more. Located inside the 24-hour guard-gated Cypresswood Golf & Country Club community featuring championship golf, tennis, pickleball, clubhouse dining, fitness center, and resort-style amenities. Conveniently located near Legoland, Disney, Orlando attractions, top restaurants, shopping, malls, medical facilities, and major highways with easy access to both Tampa and Orlando. Luxury golf properties with this combination of views, privacy, updates, lot positioning, and value rarely become available.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1
BERRYHILL - L4962251 - 343 STERLING DR, WINTER HAVEN, FL 33884 1 Day on yellowkey
$259,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome to 343 Sterling Drive in the well-established and well-loved Berryhill community of Winter Haven. This 3 bedroom, 2 bathroom home features a functional split floorplan and a wonderful opportunity for buyers looking to add their own cosmetic style and personal touches while enjoying several important updates already completed. Major improvements include replumbing throughout the home completed in 2016, new windows 2018, new roof in 2020, and a brand-new water heater in 2026 — providing peace of mind for many of the home’s major components. Step outside to enjoy the covered patio and private fenced backyard setting, offering a peaceful space for relaxing, entertaining, or enjoying quiet evenings at home. Berryhill is known for its established charm and convenient location with a very low annual HOA. Ideally situated near shopping, dining, medical facilities, and local attractions including LEGOLAND Florida Resort. This home combines comfort, value, and potential in one of Winter Haven’s convenient locations. Additional features include an interior laundry room and spacious two-car garage, adding everyday functionality and convenience.
Listing is courtesy of: THE STONES REAL ESTATE FIRM
BEYMER STONER SUB - TB8513310 - 2207 AVENUE F NW, WINTER HAVEN, FL 33880 1 Day on yellowkey
$255,000 | Single Family Home | 3 beds | 2.0 baths
Charming and well-maintained home in Winter Haven featuring gorgeous wood flooring throughout the main living areas and porcelain ceramic tile in the kitchen. The beautifully updated kitchen features stainless steel appliances, a gas stove, soft-close cabinets, and ceramic tile flooring, offering both style and functionality. The front enclosed sunroom is filled with beautiful natural morning light through surrounding windows, creating the perfect space to relax, enjoy your coffee, or unwind throughout the day. Conveniently located near several beautiful lakes; including Lake Howard, this property offers the best of Florida living while being situated in a FEMA-designated dry zone outside of the flood area for added peace of mind. Enjoy major energy savings with the fully paid-off solar panel system already in place, helping keep electric bills low for the new owner. Additional updates include a newer roof and AC system, along with a full-house gas generator capable of powering the entire home during storms or outages with the flip of a switch. The spacious backyard workshop provides ample room for tools, hobbies, storage, or workspace needs. Conveniently located near shopping, dining, parks, and recreational opportunities, this property is ideal for buyers seeking comfort, efficiency, preparedness, and functionality all in one. Schedule your private showing today!
Listing is courtesy of: SOUTHERN PINE REALTY GROUP, LLC
HAVEN HOMES SUB - O6411347 - 2234 AVENUE B NW, WINTER HAVEN, FL 33880 1 Day on yellowkey
$219,000 | Single Family Home | 3 beds | 2.0 baths | 1 car
One or more photo(s) has been virtually staged. Meet 2234 Avenue B NW, a residence recently enhanced by fresh interior paint and a partial flooring replacement. A functional fireplace enhances the living area, and an exterior storage shed provides practical utility. The property also includes a well-defined fenced in backyard. Thoughtful updates and practical features make this a must-see.. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC
HARTRIDGE MANOR - S5150017 - 820 AVENUE Z NW, WINTER HAVEN, FL 33881 1 Day on yellowkey SHORT SALE
$197,500 | Single Family Home | 3 beds | 2.0 baths
Short Sale. Discover a wonderful opportunity in the desirable Winter Haven area. This inviting residence offers comfortable living with a practical and welcoming layout. Bright natural light enhances the interior, creating a warm and airy feel throughout. The living areas flow seamlessly, making everyday living and entertaining effortless. A functional kitchen provides plenty of space for cooking and gathering. Spacious bedrooms showcase relaxing retreats for rest and privacy. The home sits on a generous lot with room to enjoy outdoor living. The backyard is perfect for relaxing evenings, gardening, or weekend gatherings. With no HOA, you’ll enjoy added flexibility and freedom. Ample parking adds convenience for residents and guests alike. The location provides easy access to shopping, dining, and daily essentials. Nearby parks and lakes fit outdoor recreation opportunities year-round. Major roadways are just a short drive away for easy commuting. This property is a great fit for homeowners or investors seeking value and potential. Come explore the possibilities this home has to show for.
FLA HIGHLANDS CO SUB - O6409847 - 215 KILMER LN, WINTER HAVEN, FL 33884 1 Day on yellowkey
$379,998 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Fully Occupied Income Property | 3 Units | $4,300/mo Gross Rent | No Vacancy | Winter Haven Rare turnkey income property generating $4,300/month in gross rent — fully occupied with zero vacancy. This versatile multi-income single-family property features two interior apartments plus a separate rear cabin, each independently rented with established tenants in place. Landlord expenses are minimal: owner covers water (~$25/mo) and basic WiFi ($50/mo). Tenants handle electricity, lawn maintenance, and all other utilities — maximizing net cash flow from day one. 4 bedrooms | 2 bathrooms | 1,680 sq ft | Built 1965 | Polk County | Minutes from US-27, downtown Winter Haven, and Legoland Florida. Ideal for the buy-and-hold investor seeking immediate cash flow with low management overhead. Current leases transfer at closing. All financing welcome: Conventional | DSCR Loan | Cash.
Listing is courtesy of: CAISSA REALTY INVESTMENT INC
HARBOR AT LAKE HENRY - L4962260 - 517 ITUNA CIR, WINTER HAVEN, FL 33881 1 Day on yellowkey
$313,710 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Under Construction. New construction home with 1715 square feet on one-story including 4 bedrooms, 2 baths, and an open living area. Enjoy an open kitchen with Quartz countertops, Samsung stainless steel appliances, a walk-in pantry, and a spacious island, fully open to the dining café and gathering room. The living area, laundry room, and baths include luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. Your owner's suite is complete with a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. Plus, enjoy a covered lanai, 2-car garage, custom-fit window blinds, architectural shingles, energy-efficient insulation and windows, and a full builder warranty ***Please note - Virtual Tour/Photos showcases the home layout; colors and design options in actual home for sale may differ. Furnishings and décor do not convey!
Listing is courtesy of: CAMBRIDGE REALTY OF CENTRAL FL
CYPRESSWOOD PATIO HOMES - L4962087 - 460 PINEHURST CT, WINTER HAVEN, FL 33884 1 Day on yellowkey
$249,000 | Single Family Home | 2 beds | 2.0 baths | 2 gar
Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida — an updated and spacious 2 bedroom, 2 bath patio home tucked away on a quiet cul-de-sac street with no through traffic. A private walled walkway leads to a charming front porch with sitting area, creating a warm and welcoming approach. Step inside the foyer to discover a clean, updated interior offering more than 1,600 square feet of comfortable living space, highlighted by beautiful new flooring, a freshly painted interior, and a long list of thoughtful improvements. All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive, and easy-to-maintain property. The roof was replaced in 2020 for added peace of mind, and gutters have also been installed for convenience and functionality. The great room design creates a spacious and open feel, accentuated by built-in shelving and large glass sliders that bring in natural light while offering the perfect space to showcase personal décor and seasonal accents. Sliding glass doors open to the enclosed, air-conditioned Florida room, seamlessly expanding the living area and creating an easy indoor-outdoor lifestyle that can be enjoyed year-round. The great room also offers space for formal dining in addition to the casual eat-in area found within the kitchen. The generously sized kitchen features abundant real wood cabinetry, a large breakfast bar, closet pantry, and an inviting dining area ideal for casual meals and everyday living. The primary suite offers comfortable dimensions, a walk-in closet, and an en-suite bath complete with a tiled walk-in shower. The guest bedroom is also nicely sized and features its own walk-in closet along with convenient access to the full guest bathroom with tub and shower. Storage is abundant throughout the home with multiple interior closets, garage storage closets, and a spacious 2-car garage with laundry connections, helping keep everything neatly organized and out of sight. Additional features include an irrigation system and low-maintenance exterior living. Beyond the home, Cypresswood delivers one of Winter Haven’s most enjoyable golf community lifestyles. Residents enjoy access to the 18-hole championship golf course, originally opened in 1969 and designed by award-winning architect Ron Garl. Known for its rolling fairways and mature landscaping, the course also features a pro shop, driving range, putting green, and dedicated short-game practice areas. Just a short stroll from the home, residents can enjoy the recently refurbished junior Olympic-sized swimming pool, tennis courts, pickleball courts, and Wellness Center. The Cypresswood Pub & Restaurant serves as the social heart of the community, offering planned events, a full bar, great food, and live weekend music in a relaxed setting overlooking the golf course. Whether you are searching for a full-time residence, winter retreat, or low-maintenance golf community home, 460 Pinehurst Ct offers an exceptional opportunity to enjoy the Florida lifestyle in one of Winter Haven’s most established gated golf communities.
SOUTH ROY SHORES - O6411362 - 2540 14TH ST SE, WINTER HAVEN, FL 33884 2 Days on yellowkey
$369,900 | Single Family Home | 4 beds | 2.0 baths
Turnkey Airbnb opportunity in the heart of Winter Haven! This fully furnished 4-bedroom, 2-bath pool home is perfect for short-term rental income, multi-generational living, or your next investment property. Featuring a flexible multi-generational layout and a suite with its own entrance, the home includes a private in-law suite, creating the ideal setup for guests or extended family. Recent updates include a new roof installed in 2023 for added peace of mind. Inside, you'll find bright and spacious living areas, a functional kitchen with ample cabinet and counter space, and comfortable bedrooms designed for relaxing stays. Outside, enjoy a fully fenced backyard with a private in-ground pool, plenty of room to entertain, and space to unwind. The large driveway and oversized 2-car carport provide ample parking for guests, boats, or multiple vehicles. With no HOA and the property being sold fully furnished, this move-in-ready home offers incredible flexibility as a primary residence, vacation getaway, or income-producing Airbnb. Conveniently located near shopping, dining, schools, and area attractions.
ELOISE POINTE ESTATES - P4938801 - 2553 PARTRIDGE DR, WINTER HAVEN, FL 33884 2 Days on yellowkey
$399,900 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Don't miss out on this very rare opportunity to secure a home in the prestigious Eloise Pointe Estates, as homes in this gated subdivision rarely come on the market. This split-bedroom, open-plan POOL home is on an oversized lot and features 4 bedrooms, a den, and 2 baths. Upon arrival, the twin large oak trees that dominate the front yard serve to bracket the home. The mature landscaping is irrigated by an automatic system fed by a well, a real money saver. The side-load double garage is at the end of a wide driveway with a parking pad. The covered front entry leads to a front door with a leaded-glass insert. Once inside, the welcoming foyer receives additional natural light from the leaded-glass sidelights and the over-the-transom window. The dining room access from the foyer is defined by beautiful architectural arches and pass-through openings. The dining room gets great ambient light from the large arched double window at the front of the home. On the opposite side of the foyer, near the front door, is the home office/den. The den's double doors are a welcome feature when privacy is desired. The den also has a double arched window, adding symmetry to the front of the home, and a ceiling fan. The foyer opens into the great room via an arch. The great room has a quadriple slider that opens to the covered lanai and pool area, a ceiling fan, and crown molding. Adjacent to the great room is the chef's delight kitchen with its stainless steel appliances, ample cabinetry and counter space, handy snack bar, and walk-in pantry. The dining room is easily accessed from the kitchen through another archway. Next to the kitchen is the dinette. The architectural glass in the dinette gives great visibility to the pool and backyard. Just off the kitchen is the west wing and the short hallway that leads to the primary bedroom suite. The huge primary bedroom has a raised tray ceiling, a ceiling fan with light, and is at the rear of the home. The primary suite has a large walk-in closet and a primary bath with a linen closet, dual vanities, a private toilet area, a stall shower with a glass door, and a corner jetted tub. Also behind the kitchen is the indoor laundry room, which doubles as the mudroom for the attached two-car garage. The washer and dryer stay with the new owners. The entire east wing holds the 3 other bedrooms. Bedrooms 2 and 3 have ceiling fans and walk-in closets. Bedroom 4 is at the front of the home and has a ceiling fan and a reach-in closet. The hall connecting all 3 bedrooms houses the guest bath with a combined tub and shower. There are many architectural touches throughout that increase the "coolness" of this home. Special woodwork, a creche, crown molding, and built-in features abound. The covered lanai area has 2 ceiling fans. The 16x32 pool sits inside a large birdcage area and has a safety fence and attachments for pool volleyball. The pool has a "V"- shaped bottom and easy-access steps and railings at both ends. The backyard has a vinyl fence, perfect for the family's furry member. The home also has 35 solar panels, which greatly impacts the electric bill. Of special importance is that the roof was replaced in 2020, the water heater in 2022, and the AC in 2024. Don't miss out on the chance to move into the highly desirable Eloise Pointe Estate.
Listing is courtesy of: A+ REALTY LLC
BERRYHILL - S5150673 - 307 STERLING DR, WINTER HAVEN, FL 33884 2 Days on yellowkey SHORT SALE
$260,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Short Sale. Short Sale. Looking for a nice home with amazing potential and opportunity to gain equity? This one may be IT for you! Welcome to this 3-bedroom, 2-bath move-in ready home located in the peaceful and sought-after SE Winter Haven area! Situated on an OVERSIZED corner lot, this home features a fully fenced backyard, high ceilings, and ceramic tile flooring throughout the main living spaces. You’ll love the screened-in lanai and Private Pool—perfect for relaxing or entertaining year-round. The kitchen boasts custom cabinetry, a cozy dinette with wraparound windows, and direct access to an oversized garage. The spacious master bedroom features a walk-in closet, while the additional bedrooms are ideal for family or guests. This home has AMAZING POTENTIAL and nestled in a quiet, well-kept neighborhood, just minutes from Legoland and all of Central Florida’s top attractions. Call today to schedule your private showing—this home is priced to sell and won’t last long!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III
WEST CANNON HEIGHTS - A4694880 - 1220 33RD ST NW, WINTER HAVEN, FL 33881 3 Days on yellowkey
$139,987 | Single Family Home | 3 beds | 1.0 baths | 1 car
Charming 3-bedroom, 1-bath home with no HOA, offering a great opportunity for investors or first-time buyers alike. Conveniently located in Winter Haven with easy access to shopping, dining, schools, major roadways, and everyday amenities. This property offers plenty of potential and is ideal for those looking to expand their portfolio or create a place to call home.
Listing is courtesy of: JOSEPH WALTER REALTY LLC
QUEENS COVE PH 02 - TB8511669 - 3311 QUEENS COVE LOOP, WINTER HAVEN, FL 33880 3 Days on yellowkey
$249,999 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Don't miss this move-in ready, recently updated 3 bedroom, 2 bathroom block home with a 2-car garage, situated on a spacious 7,370 sq ft lot in Winter Haven. This 1994 built home features a recently remodeled kitchen with quartz countertops, shaker cabinets, stainless steel appliances, luxury vinyl plank flooring, updated bathrooms, and fresh paint throughout! Major components like the roof and A/C have both been updated in recent years, with plenty of life remaining for added peace of mind. The open living room features a shiplapped fire place. Out back, enjoy the newly installed paver patio, perfect for grilling, relaxing, or entertaining in the spacious yard. This is a great value for a well-updated home with both indoor and outdoor space at an affordable price point with a low HOA! FHA and VA friendly! *Some photos have been virtually staged*
Listing is courtesy of: IMPACT REALTY TAMPA BAY
BUCKEYE HEIGHTS - P4938800 - 1406 MEADOW DR NE, WINTER HAVEN, FL 33881 3 Days on yellowkey
$265,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Spacious Single-Story Block Home with Endless Potential! Nestled in a quiet, established neighborhood close to Polk State College with no HOA, this solid single-story block home immediately catches the eye with its charming blend of stucco and natural multi-colored stone accents. Boasting 1,678 square feet of comfortable living space (2,527 square feet total), the interior features a generously sized layout including three spacious bedrooms and two bathrooms. The primary suite is a true retreat, complete with a walk-in closet for ample storage. At the heart of the home, a large kitchen and dining area provides the perfect setup for family gatherings and entertaining. Step outside onto the oversized 0.26-acre lot, where the backyard offers a private oasis featuring mature, producing fruit trees, a handy detached storage shed, and a solid privacy fence running across the rear property line. Perfectly situated in a desirable community zoned for great local schools, this property has incredible bones and just needs some updating and TLC to truly shine. The seller is highly motivated and ready to see your offers—bring your design ideas and schedule your private showing today to unlock this home's immense potential!
Listing is courtesy of: LA ROSA REALTY PRESTIGE
PEACE CREEK RESERVE - TB8509963 - 1688 TEAGAN LN, WINTER HAVEN, FL 33884 3 Days on yellowkey
$285,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome to easy Florida living in the sought-after community of Peace Creek Reserve in Winter Haven! Built in 2024, this beautifully designed 3-bedroom home offers a modern split-bedroom layout, stylish finishes, and comfortable open living spaces perfect for both relaxing and entertaining. Step inside to discover bright and airy living areas with durable tile flooring flowing throughout the main spaces. The stunning kitchen is the heart of the home, featuring sleek stainless steel appliances, a large center island with seating space, abundant cabinetry, and an open design that overlooks both the dining area and spacious living room—making it easy to stay connected while hosting family and friends. Tucked away at the back of the home for added privacy, the primary suite offers a peaceful retreat with a generously sized bedroom, private ensuite bath with dual sink vanity, and a custom walk-in closet designed for organization and convenience. The split floor plan places the additional bedrooms and secondary bath on the opposite side of the home, creating flexibility for guests, family members, or a home office setup. Thoughtfully designed with newer construction benefits in mind, this home offers modern efficiency, low-maintenance living, and the peace of mind that comes with a recently built home. Peace Creek Reserve offers a convenient Winter Haven location close to shopping, dining, parks, lakes, and everyday essentials, while also providing easy access for commuting throughout Central Florida. Enjoy nearby outdoor recreation, local attractions, and all the charm that Winter Haven living has to offer. Whether you are looking for your first home, downsizing, or simply ready for a newer home with modern style and functionality, this one is ready to welcome you home. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA
WILLOWBROOK NORTH - O6410787 - 811 ANDREW ST, WINTER HAVEN, FL 33881 3 Days on yellowkey
$322,490 Increased | Single Family Home | 3 beds | 2.0 baths | 2 gar
Under Construction. The Atwood floor plan features 3 bedrooms, 2 full baths, approximately 1,600 sq. ft., an open-concept design, spacious kitchen island, private primary suite, and thoughtfully designed living spaces that combine comfort, style, and everyday functionality in a growing Central Florida location. Willowbrook North offers modern single-family homes in a boutique Winter Haven community near Lake Fannie and Willowbrook Golf Club, with convenient access to shopping, dining, Downtown Winter Haven, US-27, and I-4.
Listing is courtesy of: DRB GROUP REALTY, LLC
WILLOWBROOK NORTH - O6410465 - 333 MEREDITH BLVD, WINTER HAVEN, FL 33881 3 Days on yellowkey
$356,940 Increased | Single Family Home | 5 beds | 3.0 baths | 2 gar
Under Construction. The Ponte Vedra floor plan at Willowbrook North offers spacious two-story living with 5 bedrooms, 3 full baths, and approximately 2,371 square feet of thoughtfully designed space. This open-concept home features a modern kitchen overlooking the great room and dining area, a spacious primary suite, flexible living areas, and available options. Located near Lake Fannie and adjacent to Willowbrook Golf Club, Willowbrook North offers scenic surroundings with convenient access to shopping, dining, parks, downtown Winter Haven, and major commuter routes to Orlando and Tampa. Buyers will also enjoy energy-efficient features and modern interior finishes.
GARDEN GROVE SOUTH ADD - O6410695 - 912 E HERON CIR, WINTER HAVEN, FL 33884 4 Days on yellowkey
$325,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome to this FULLY renovated, beautiful and large 3Bed 2bath home in Winter Haven!! Property has been fully renovated to 2026 standards in and out. Fresh pain in and out. Brand new 6" baseboards throughout the home. Crown molding throughout the main living space. Brand new water resistant LVP tile. Pool has been repainted. Walls have been refreshed and smoothened out. Popcorn ceiling through the main home has been sanded down and smoothened. Garage has been given a fresh coating of pain and the floors smoothened. Both Florida rooms have been renovated as well. Roof (2020) A/C (2020) New Water-heater installed (2026) Stainless Steel Samsung Dishwasher (2026) Stainless Steel Samsung Fridge (2026) Stainless Steel Whirlpool Electric Range (2026) Stainless Steel Broan-NuTone Range Hood (2026). Solar Panels are fully owned. Full 3D property walk-through video available upon request. PLEASE NOTE - I AM NOT AVAILABLE ON THE SABBATH/SATURDAYS
Listing is courtesy of: CARDINAL REALTY GROUP, LLC.