Location: Winter Haven
Keyword(s): Winter Haven Senior
Keyword(s) High School: Winter Haven Senior
Do Not Show Listings
276 MEREDITH BLVD, WINTER HAVEN, FL 33881
$329,99011 Days on yellowkey MLS ID: G5113493
0 Days Off yellowkey (back on 6/8/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2110 Built: 2025Monthly Fee: $7 Tax: $500 (2025)Community: Willowbrook NorthSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$500
Elementary School: Fred G. Garnier Elem
High School: Winter Haven Senior
Tax Year: 2025
Middle School: Denison Middle
Remarks: Poinciana floorplan, located in the highly sought-after community of Willowbrook near a beautiful golf course in Winter Haven, FL. This spacious 4-bedroom, 3-bath home offers 2,110 square feet of living space, and providing excellent curb appeal in it's elevation. Inside, you'll find gorgeous Gray cabinets complemented by sleek quartz counter tops in the kitchen, creating a modern, bright atmosphere. Tile flooring runs throughout the wet and common areas, offering durability and easy maintenance. The open layout is perfect for family gatherings and entertaining guests.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
2954 PLANTATION RD, WINTER HAVEN, FL 33884
$744,90022 Days on yellowkey MLS ID: P4938830
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4190 Built: 1989Monthly Fee: $137 Tax: $7,558 (2025)Community: Cypress PlantationsSpa: YesSingle Family
Taxes:$7,558
Elementary School: Garden Grove Elem
Remarks: Under contract-accepting backup offers. 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 (863-508-3000)
Listing Agent: Justino Zoppe (417-848-1383)
1522 ECKART DR, WINTER HAVEN, FL 33881
$359,99979 Days on yellowkey MLS ID: L4959745
REDUCED by $19,901 (5.2%) on 06/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1524 Built: 1982 Tax: $3,192 (2025)Community: Rochelle GardensSingle Family
Taxes:$3,192
Elementary School: Lake Alfred Elem
Remarks: This updated 3-bedroom, 2-bath home offers comfort, functionality, and plenty of outdoor space to enjoy Florida living. Inside, you’ll love the spacious open floor plan featuring a Great Room, dining area, and family room combination with cathedral ceilings, wood burning fireplace, laminate wood flooring, and abundant recessed lighting. French doors from the dining room lead to an open patio and a large backyard—ideal for entertaining or relaxing outdoors. This home is light and bright and move-in ready just for you! The kitchen features white raised-panel PVC cabinetry, black tile countertops, a closet pantry, and updated appliances including a refrigerator (2026) and stove (2022). Major system upgrades include a new 3.5-ton A/C system with new ductwork and a roof replaced in 2022. The split-bedroom layout offers privacy, with both bathrooms very nicely updated. The spacious primary suite includes a beautiful bath with stone floors, a quartz vanity with integral sink and wall-mounted faucet, and a walk-in shower with new tile, glass doors, and drain pan—part of a $15,000 renovation. Additional highlights include a garage with mini-split A/C, insulated garage door, pull-down ladder for attic access, washer/dryer hookup, and laundry sink. Outside you will have a 10’x12’ shed with electric, and a well house with a Culligan water softener system. A new black aluminum fence surrounds the property, with vinyl PVC privacy fencing along the left side, 12-foot gates on both sides plus a 6-foot front gate—perfect for storing a boat, RV, or extra vehicles. A covered rear carport adds even more flexibility. Conveniently located on a large corner lot near lakes, parks, recreation areas, LEGOLAND, Hwy 27 & I-4, and all that Central Florida has to offer. Welcome home!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Russ Rhoads (863-604-1570)
447 SAN JOSE DR, WINTER HAVEN, FL 33884
$239,900128 Days on yellowkey MLS ID: P4937807
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1600 Built: 1980Monthly Fee: $5 Tax: $1,532 (2025)Community: Orchid Springs Patio HomesSingle Family
Taxes:$1,532
Elementary School: Elbert Elem
Remarks: With expanded living areas and versatile spaces, this home offers a comfortable and practical Florida lifestyle in a well-established Winter Haven community. New flooring and fresh interior paint provide a clean, neutral foundation ready for its next owner. Tucked toward the back of the community and accessed by charming, canopy tree-lined roads, the setting offers a peaceful, neighborhood feel ideal for evening walks or bike rides. The enclosed Florida room adds valuable square footage and serves as a flexible extension of the main living area, perfect for everyday living or casual entertaining. A fully enclosed and roofed former atrium creates a unique bonus space that can be enjoyed year-round, offering additional flexibility for hobbies, relaxation, or storage. The fenced backyard provides a private outdoor retreat and features resident koi fish, adding a tranquil touch. The home is equipped with a whole-house generator, offering dependable peace of mind. Residents also enjoy access to the community clubhouse and amenities. Conveniently located near shopping, dining, medical facilities, and major roadways, this property combines comfort, function, and location within a charming, established neighborhood.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: J. Michael Nolen, Jr (863-294-7541)
2813 WINGFOOT CT, WINTER HAVEN, FL 33884
$215,000108 Days on yellowkey MLS ID: L4959887
1 Days Off yellowkey (back on 6/8/2026)
REDUCED by $15,000 (6.5%) on 04/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1682 Built: 1990Monthly Fee: $295 Tax: $2,981 (2025)Community: Cypresswood Golf VillasSpa: NoVilla
Taxes:$2,981
Remarks: Under contract-accepting backup offers. Welcome to 2813 Wingfoot Court — now one of the best values in Cypresswood Golf & Country Club! Perfectly positioned along the 8th fairway inside this guard-gated golf community, this beautifully maintained 2-bedroom, 2-bath villa offers peaceful views and effortless Florida living—now at an exceptional new price. Being sold fully furnished and truly turnkey, this home is ready for immediate enjoyment—just bring your suitcase. Inside, you’ll find a professionally designed interior with vaulted ceilings that create a bright, open feel throughout the main living spaces. The kitchen includes updated appliances, including a newer stove and microwave, while most windows have been upgraded for improved efficiency and style. A tankless hot water heater adds modern convenience and energy savings. The spacious primary suite features a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and easy access to a second full bath—perfect for hosting family and friends. One of the home’s standout features is the inviting Florida room, ideal for morning coffee or relaxing after a day on the course. Step outside to the stained and stamped patio overlooking the fairway, creating a perfect space for entertaining or unwinding. Major updates include a roof (2019) and A/C (2018), providing added peace of mind. Residents enjoy access to community amenities including a pool, tennis courts, clubhouse, and on-site restaurant—all just minutes from shopping, dining, and major roadways. Now aggressively priced—don’t miss this opportunity to own in Cypresswood at one of the most attractive price points in the community.
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Corinna Weaver (863-258-2901)
1280 W LAKE HAMILTON DR, WINTER HAVEN, FL 33881
$1,259,00016 Days on yellowkey MLS ID: L4961525
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 5416 Built: 1995 Tax: $7,019 (2025)Community: N/ASingle Family
Taxes:$7,019
Remarks: Spanish-inspired architecture, artistic flair, and breathtaking lakefront scenery come together in this truly one-of-a-kind estate on the shores of Lake Hamilton. Situated on more than one acre of fully fenced waterfront property with a wrought-iron gated entrance and no HOA restrictions, this custom residence offers over 5,400 square feet of living area designed for both grand entertaining and everyday enjoyment of Florida's lakefront lifestyle. From the moment you arrive, the home's distinctive architectural design makes a lasting impression. A circular driveway leads to the large covered portico where a tranquil fountain welcomes guests and creates an unforgettable arrival experience. Stepping through the double doors reveals a dramatic foyer with soaring ceilings, abundant natural light, and immediate panoramic lake views. Throughout the home, artistic influence and personality are evident at every turn. One of the owners is an accomplished artist, and their creativity is beautifully reflected in the home's unique design elements, decor, and inviting spaces. The completely remodeled kitchen, updated in 2018, serves as the heart of the home and features extensive custom cabinetry, granite countertops, a striking raised glass breakfast bar, center island with a built-in wine trough, and a bright eat-in dining area overlooking the lake. Nearby, the formal dining room provides the perfect initimate setting for holiday gatherings and special occasions. Designed with flexibility in mind, the home offers multiple living and entertaining spaces including a spacious family room anchored by a fireplace, dedicated office, theater room, enclosed Florida room stretching across the rear of the home, and numerous areas for relaxation or hosting guests. The expansive Florida room is the ideal place to begin each day with coffee while watching spectacular sunrises paint the sky over the water. The first floor features three generously sized guest bedrooms, while the private owner's retreat occupies the upper level. This luxurious sanctuary enjoys elevated wraparound views of Lake Hamilton, creating a peaceful escape unlike anything else in the area. Also located above is a unique artist's perch or widow's walk, offering an elevated vantage point to enjoy panoramic views, morning and evening skies, wildlife watching, and endless inspiration. Outdoor living is equally impressive. The heated salt-filtered pool, completed in 2018, overlooks the lake and creates a resort-style atmosphere. Expansive paver decking and wide-open lawn areas provide ample room for family gatherings, pets, and outdoor recreation. A composite dock extends into Lake Hamilton, making it easy to enjoy boating, fishing, paddleboarding, and sunset cruises. Spanning nearly 1,900 acres, Lake Hamilton is widely known for its excellent fishing, boating opportunities, and scenic beauty. Cruise across the lake to enjoy dining and entertainment at local favorites such as Floridino's and Port 27 before returning home for a peaceful sunset ride across the water. Additional features include a detached two-car garage, large storage shed and the privacy and freedom that comes with having no HOA. Rarely does a property combine architectural character, artistic expression, expansive living space, resort-style amenities, and over an acre of lakefront land in such a remarkable setting. This is more than a home—it is a private waterfront retreat where every sunrise feels like a work of art.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
47 ENCLAVE DR, WINTER HAVEN, FL 33884
$245,000114 Days on yellowkey MLS ID: P4937867
REDUCED by $15,000 (5.8%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1444 Built: 1999Monthly Fee: $433 Tax: $3,221 (2025)Community: Cypresswood Enclave Ph 2Spa: NoVilla
Taxes:$3,221
Remarks: PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the Interior was Freshly Painted. Be sure to take time to enjoy the view from your Screened Porch. There are No Homes behind you, just open pastures, roaming cows, and trees. Very peaceful. The HOA fee also includes the Landscaping, Lawn Maintenance, Exterior Painting, and Roof (replaced in 2023) for your Villa. This Home allows you to relax and enjoy a game of Golf, take a swim in the Olympic Pool, or just enjoy the view from your Screened Porch. The Home is located close to Shopping (New Publix), Restaurants, Downtown, and Highway 27 which leads to Interstate 4 for Tampa and Orlando (Disney World). Come see what this home can offer you!
Listing is courtesy of: XCELLENCE REALTY, INC (866-595-6025)
Listing Agent: David Shippey (863-521-4517)
373 LAKE DAISY CIR, WINTER HAVEN, FL 33884
$215,000196 Days on yellowkey MLS ID: L4957732
1 Days Off yellowkey (back on 6/6/2026)
REDUCED by $10,000 (4.4%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1391 Built: 1990 Tax: $3,356 (2025)Community: Lake Daisy EstatesSpa: NoSingle Family
Taxes:$3,356
Remarks: Under contract-accepting backup offers. MOTIVATED SELLERS...OPPORTUNITY KNOCKS ON THIS SPACIOUS & AFFORDABLE 3 Bedroom/2 Bath Home in the heart of SE Winter Haven located in Lake Daisy Estates is ready for you & your family!!! NO HOA or CDD in this established neighborhood that is within 3 miles of LEGOLAND and close to multiple restaurants, shopping, & parks. The natural light fills each room of the home. Open floor plan with split bedrooms. You'll love the large open backyard that is fully fenced. Newer roof (2023). Schedule a tour today!!!
Listing Agent: Cheryl Brewer (863-224-0045)
108 LAKE REGION BLVD N, WINTER HAVEN, FL 33881
$425,000198 Days on yellowkey MLS ID: L4957549
REDUCED by $14,000 (3.2%) on 04/13/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2495 Built: 1996Monthly Fee: $85 Tax: $3,479 (2025)Community: Gates Of Lake RegionSingle Family
Taxes:$3,479
Remarks: Located within the highly desirable gated community of The Gates of Lake Region, this beautifully maintained neighborhood is known for its picturesque brick-walled entrance, lush mature landscaping, tranquil ponds with fountains, and pride of ownership throughout. Unlike larger developments, The Gates of Lake Region offers a warm, neighborly atmosphere where residents enjoy quiet streets, manicured lawns, quality-built homes, and a true sense of community. This spacious 2,500-square-foot residence was originally constructed as a builder's model home and showcases numerous upgrades and architectural details throughout. Built with high-efficiency Ytong concrete block construction, the home offers superior sound reduction, enhanced structural performance, and meaningful energy savings. The elegant floor plan features 4 spacious bedrooms (one currently utilized as an office), 2 full bathrooms, and 1 half bath. Refined interior finishes include crown molding, oversized custom doors, handcrafted double entry doors, custom cabinetry, ceiling fans, a jetted tub in the primary suite, and a generously sized laundry room. Mature landscaping and a covered front entry create an inviting first impression. Inside, the foyer opens to formal living and dining areas accented by soaring ceilings and detailed trim work, providing an elegant setting for both everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, solid-surface countertops, a closet pantry, and a bright breakfast nook overlooking the screened lanai and private brick-walled backyard. The comfortable family room is centered around a granite-faced gas fireplace that adds warmth and character. A desirable split-bedroom layout provides privacy for the primary suite, which features a spacious walk-in closet, soaking tub, and tiled walk-in shower. The guest wing includes two additional bedrooms with generous closet space and convenient access to the guest bath. Outdoor living is equally inviting with a large screened lanai, mature tropical landscaping, and a private brick-walled backyard designed for relaxation and enjoyment. Additional features include an oversized two-car garage, natural gas water heater, irrigation system, and an efficient interior laundry room with additional storage. Residents of The Gates of Lake Region enjoy a peaceful setting surrounded by scenic ponds, decorative fountains, and beautifully maintained common areas, all while being just minutes from the Winter Haven Chain of Lakes, several golf courses, the Country Club of Winter Haven, medical facilities, shopping, dining, and Downtown Winter Haven. A new Publix is also planned nearby for added convenience. Orlando, Tampa, international airports, and both Florida coasts are all within easy driving distance. If you're searching for a community that combines timeless charm, quality homes, beautiful surroundings, and a genuine neighborhood feel, The Gates of Lake Region is a place you'll be proud to call home.
3742 FIELDSTONE CIR, WINTER HAVEN, FL 33881
$300,00014 Days on yellowkey MLS ID: L4962401
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 2016Monthly Fee: $36 Tax: $4,631 (2025)Community: Country Club EstatesSingle Family
Taxes:$4,631
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,919 square feet of comfortable living space in the well-kept community of Country Club Estates of Winter Haven. Lovingly cared for as a second home, this residence shows pride of ownership throughout and is truly move-in ready. The spacious floor plan provides plenty of room for everyday living and entertaining, while the extended screened rear patio creates the perfect setting to relax, enjoy your morning coffee, or unwind after a long day while taking in the peaceful surroundings. One of the property's most desirable features is its private backyard setting with no rear neighbors. The vacant parcel directly behind the home is designated for drainage and retention and is not slated for future development, providing added privacy and open views (buyer to verify with Polk County). Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this well-kept home offers comfort, privacy, and a fantastic Winter Haven location. Don't miss your opportunity to make it yours today!
Listing Agent: Brandy Duncan (863-585-6849)
381 WINTER RIDGE BLVD, WINTER HAVEN, FL 33881
$143,000163 Days on yellowkey MLS ID: S5140657
REDUCED by $2,500 (1.7%) on 05/31/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1996Monthly Fee: $253 Tax: $2,125 (2025)Community: Winter Ridge CondoCondo
Taxes:$2,125
Middle School: Lake Alfred-Addair Middle
Remarks: One or more photo(s) has been virtually staged. Waterfront view from your porch. Affordability, low-maintenance comfort, & strong rental income potential. Waterfront view from your porch. Discover serene living at this charming 2-bedroom, 2-bathroom condo offering stunning sunset water views from its screened lanai. The home has a functional layout, it includes a combination of living & dining area, a large master suite with a walk-in closet, & a sliding glass door towards your comfortable back porch overlooking the canal water view; the kitchen has sufficient space; & there is a large storage room. Enjoy your Florida lifestyle, this welcoming community with built-in amenities, has direct lakefront access via a community dock for boating, fishing, and water sports on the connected Chain of Lakes. For only $253 a month, HOA covers your home's exterior maintenance. Location is accessible to nearby shopping, hospitals, medical offices, schools, and about an hour drive Tampa or Orlando. To schedule a showing, provide your realtor your pre-approval letter or proof of cash funds. At this price range, this move-in ready condo is your best choice.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Lienyvette Grimaldo (863-399-0226)
2500 21ST ST NW #15, WINTER HAVEN, FL 33881
$182,00077 Days on yellowkey MLS ID: S5147117
REDUCED by $2,000 (1.1%) on 05/30/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1184 Built: 1976 Tax: $2,616 (2025)Community: Casa Del Sol Condo Village Ph 02Condo
Taxes:$2,616
Middle School: Westwood Middle
Remarks: Completely remodeled and move-in ready, this stunning 2-bedroom, 2.5-bathroom condo in Casa Del Sol Village offers modern updates and a comfortable layout in the heart of Winter Haven. Every corner has been renovated, featuring new flooring, paint, lighting, kitchen appliances, doors, and beautifully updated bathrooms. The spacious living room and downstairs guest half-bath make entertaining a breeze, while both upstairs bedrooms boast private en-suite bathrooms for added convenience. Enjoy a low-maintenance lifestyle with an attached one-car garage, access to the community pool, and a location close to shops and restaurants—all amidst the beautiful landscapes and lakes that surround this lovely community.
Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)
Listing Agent: Adriana Sanchez (321-947-4014)
688 AUGUSTA RD, WINTER HAVEN, FL 33884
$337,000114 Days on yellowkey MLS ID: P4937966
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1586 Built: 1980Monthly Fee: $137 Tax: $3,636 (2025)Community: Cypresswood Fairway Patio HomesSingle Family
Taxes:$3,636
Remarks: Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW ROOF! Step inside to find beautiful hardwood and tile flooring throughout, creating a warm yet low-maintenance living environment. The spacious primary suite serves as a private retreat, complete with direct access to the screen-enclosed pool deck — perfect for enjoying your morning coffee or an evening swim under the stars. The heart of the home flows seamlessly into a dedicated dining area, with an exciting bonus room just beyond featuring a fun wet bar — ideal for hosting gatherings, game nights, or creating your own lounge space. Two additional bedrooms are situated on the opposite side of the home, providing comfort and privacy for family or guests. Outdoors, the screened pool deck offers the perfect space for relaxing or entertaining year-round. The garage includes a dedicated workshop area, making it ideal for hobbyists, DIY enthusiasts, or extra storage needs. Beyond the home itself, residents enjoy an exceptional lifestyle within this premier community, featuring a championship 18-hole golf course, community pool, fitness center, clubhouse, on-site restaurant, and pro shop. Exciting new amenities are on the way, including lighted tennis courts, pickleball, and basketball courts — offering something for everyone. Whether you’re raising a family, welcoming visiting guests, or enjoying a seasonal escape, this home offers the space, setting, and lifestyle to fit every chapter. The Cypresswood community is minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options for travel in less than an hour from Disney World and other Orlando attractions, the Orlando and Tampa International Airports, and the gulf-side beaches of Tampa/St. Pete! This is more than just a home — it’s a lifestyle. Schedule your private showing today!
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
2115 KINGS XING SW, WINTER HAVEN, FL 33880
$229,90021 Days on yellowkey MLS ID: L4962289
REDUCED by $5,000 (2.1%) on 06/05/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1396 Built: 1979Monthly Fee: $100 Tax: $152 (2025)Community: StonebridgeSpa: NoSingle Family
Taxes:$152
Elementary School: Lake Shipp Elem
Remarks: *PRICE IMPROVEMENT*~2/2 Winter Haven residence Offered for Sale~ Great opportunity for a first-time home buyer or an investor! This adorable 2/2 property features 1396 square feet of living area, a split plan, two bonus rooms which could be used as bedrooms, vaulted ceilings, primary bedroom with walk-in closet and en-suite bath, wood burning fireplace, large, screened patio and a one car garage. 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 (863-940-3756)
Listing Agent: Andrea Muzzy (863-430-1733)
122 JACE WAY, WINTER HAVEN, FL 33881
$249,90046 Days on yellowkey MLS ID: L4961584
1 Days Off yellowkey (back on 6/5/2026)
REDUCED by $10,000 (3.8%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1405 Built: 2020Monthly Fee: $42 Tax: $4,217 (2025)Community: Jace LandingsSingle Family
Taxes:$4,217
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully updated three-bedroom, two-bathroom home with a two-car garage, offering 1,866 square feet under roof in the desirable community of Winter Haven. From the moment you arrive, you’ll appreciate the freshly painted exterior and updated landscaping that create strong curb appeal, setting the tone for what awaits inside. Step through the front door into a bright and refreshed interior featuring newly painted walls, updated doors, and modern light fixtures. The great room is highlighted by new luxury vinyl plank flooring that continues into all bedrooms, offering both durability and a clean, contemporary feel. The kitchen is designed for both functionality and style, featuring brand-new stainless-steel appliances and a seamless flow into the main living space—perfect for everyday living and entertaining. The split-bedroom layout provides privacy, with a spacious primary suite that includes updated mirrors and finishes in the en suite bathroom. Two additional bedrooms and a second full bath offer flexibility for family, guests, or a home office. Throughout the home, you’ll find new ceiling fans, updated blinds for window treatments, and thoughtful upgrades that make this home truly move-in ready. Additional improvements include a Brand-new roof, new hot water heater, and a freshly painted garage floor, adding both value and peace of mind. Located in a sought-after area of Winter Haven, this home offers convenient access to shopping, dining, and local attractions, while still being tucked into a welcoming community known for its charm and proximity to the area’s beautiful lakes. This is a fantastic opportunity to own a fully updated home in one of Central Florida’s most desirable and growing locations.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Jason Stone (863-838-8972)
343 STERLING DR, WINTER HAVEN, FL 33884
$259,90022 Days on yellowkey MLS ID: L4962251
2 Days Off yellowkey (back on 6/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1372 Built: 1991Monthly Fee: $27 Tax: $1,543 (2025)Community: BerryhillSpa: NoSingle Family
Taxes:$1,543
Remarks: Under contract-accepting backup offers. 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 Agent: Jessica Willaford (863-662-8549)
404 COUNTRY LN NE #404, WINTER HAVEN, FL 33881
$110,00078 Days on yellowkey MLS ID: L4960788
REDUCED by $10,000 (8.3%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1252 Built: 1985Monthly Fee: $325 Tax: $1,415 (2025)Community: Country Lake CondoSpa: NoCondo
Taxes:$1,415
Remarks: Short Sale. Welcome to your new home in this peaceful and well-maintained community! This spacious 2-bedroom, 2-bathroom condo offers comfortable, low-maintenance living with all the amenities you need to relax and enjoy life. Step inside to find a bright and open floor plan with generous living space, a well-equipped kitchen, and private bedrooms on opposite sides for added privacy. The primary suite includes a full en-suite bathroom and ample closet space, while the second bedroom is perfect for guests, a home office, or family. Enjoy your morning coffee on the screened in back patio or take a short stroll to the community clubhouse, where you’ll find a sparkling swimming pool, social spaces, and exclusive access to a private fishing area—perfect for outdoor enthusiasts. Nestled in a quiet neighborhood with beautifully landscaped grounds, this condo is ideal for those seeking comfort, convenience, and a touch of nature. Whether you're downsizing, investing, or buying your first home, this property offers a unique blend of tranquility and community living. Don’t miss this opportunity—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Casandra Vann (863-546-5446)
980 WEDGEWOOD DR SE, WINTER HAVEN, FL 33880
$450,00016 Days on yellowkey MLS ID: P4938917
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2363 Built: 2023 Tax: $6,039 (2025)Community: Wedgewood TerraceSingle Family
Taxes:$6,039
Remarks: Stunning Masterpiece! This custom built 4 bedroom, 3 bathroom home with a den/office offers over 2.300 square feet of beautifully designed living space! From the moment you step inside, you'll be captivated by the open-concept floor plan and elegant wood-look ceramic tile flooring that flows seamlessly throughout the home. The spacious living room serves as the heart of the home, showcasing a striking recessed tray ceiling accented with rich wood detailing and triple-panel sliding glass doors that fill the space with natural light while providing easy access to the rear covered patio and fully fenced backyard. The chef-inspired kitchen is designed to impress, featuring crisp white shaker cabinetry, a contrasting center island, gorgeous stone countertops, a stylish tile backsplash, and a generous walk-in pantry. The thoughtfully designed split-bedroom layout offers privacy and comfort. The luxurious primary suite is a true retreat, complete with two walk-in closets and a spa-like bathroom featuring dual vanities and an oversized walk-in shower. The 2nd bedroom has its own ensuite bathroom with access to the rear patio. Outside, the brick paver driveway and attractive stone accents create exceptional curb appeal and make a memorable first impression. Schedule your appointment today and experience everything this remarkable property has to offer!
Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)
Listing Agent: Chrissi Jasso (863-618-4000)
6502 OAK HAMMOCK LN, WINTER HAVEN, FL 33884
$169,000227 Days on yellowkey MLS ID: P4936840
0 Days Off yellowkey (back on 6/4/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1512 Built: 1998Monthly Fee: $65 Tax: $1,088 (2025)Community: Garden Grove OaksManufactured Home
Taxes:$1,088
Remarks: One or more photo(s) has been virtually staged. Best deal in Garden Grove Oaks! 55 plus manufactured home in Garden Grove Oaks! One of the best values in the community given the size, price and condition. Quietly tucked away in the peaceful 55+ community of Garden Grove Oaks, this home in excellent condition with lots of valuable updating and a spacious interior easy living. This move-in-ready 2-bedroom, 2-bath home offers thoughtful updates designed for easy, low-maintenance living, including double-pane energy-efficient windows, luxury vinyl plank flooring, a brand-new water heater, extra wide driveway, covered carport, screened patio, and a workshop/storage space. Inside, the bright and open layout provides multiple comfortable living areas, including a welcoming family room, a sunny Florida room, and a dedicated dining area—perfect for everyday living or hosting visiting friends and family. The spacious kitchen features ample cabinetry, generous counter space, and all appliances included. The primary suite offers a peaceful retreat with a walk-in closet and private bath with walk-in shower, while the guest bedroom and second full bath are ideal for visitors. At the front of the home, a light-filled Florida room with bay windows creates the perfect space for morning coffee, a home office, or hobbies. Step out to the screened porch and enclosed workshop to enjoy Florida’s mild weather year-round. Residents of Garden Grove Oaks enjoy an active, well-maintained community with a swimming pool, spa, clubhouse, shuffleboard courts, community pond, RV and boat parking, and a full calendar of social activities—making it easy to stay as engaged or as relaxed as you choose. Located in the heart of Winter Haven, you’re surrounded by over 50 lakes, including the renowned Winter Haven Chain of Lakes, along with golf courses, parks, local restaurants, and nearby attractions such as LEGOLAND Florida Resort. Everyday conveniences—Publix, Aldi, Walmart, TJ Maxx, and medical facilities—are all just minutes away. A comfortable home, a friendly 55+ community, and a convenient Central Florida location—all at an exceptional value. Don’t miss this opportunity to enjoy the Florida lifestyle at Garden Grove Oaks.
23 CASARENA CT, WINTER HAVEN, FL 33881
$230,00057 Days on yellowkey MLS ID: S5148554
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2045 Built: 1984Monthly Fee: $310 Tax: $3,909 (2025)Community: Casarena/LksSpa: NoSingle Family
Taxes:$3,909
Elementary School: Inwood Elem
Remarks: One or more photo(s) has been virtually staged. Welcome to 23 Casarena Ct in Winter Haven, located in the gated lakefront community of Casarena on the Lakes on Lake Cannon, part of Winter Haven's Chain of Lakes. This spacious 2BR/2.5BA townhome that offers approximately 2,045 sq ft of living space with vaulted ceilings, abundant natural light, and a functional two-story layout. The main level features an open living area with sliding glass doors leading to a private covered patio, plus a well-appointed kitchen with a breakfast bar and a convenient half bathroom. Upstairs, enjoy a versatile loft/bonus space ideal for a home office or additional living area. Both bedrooms offer ensuite bathrooms, including a primary suite with a private screened balcony. Additional highlights include ceramic tile & hardwood flooring, spacious bedrooms, a two-car garage with freshly painted floor & multiple outdoor spaces including three patios. Recent updates include the ROOF (Aug 2023). Owner is offering a $5,000 credit towards flooring. Residents enjoy resort style amenities: community pool, tennis courts, boat slip & dock with direct access to Lake Cannon and the Chain of Lakes, perfect for boating, fishing, and waterfront living. Prime location near shopping, dining and major roadways. Low-maintenance living in a secure, gated community.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
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