Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Price: $300,000 to $399,000
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Winter Haven - 251 properties found
112 PAINE DR, WINTER HAVEN, FL 33884
$315,000148 Days on yellowkey MLS ID: L4957763
REDUCED by $35,000 (10.0%) on 04/21/2026
Bed: 5 Bath: 2.0 Liv Area Sq Ft: 2078 Built: 1965 Tax: $3,343 (2024)Community: Fla Highlands Co SubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,343
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Denison Middle
Remarks: Seller motivated. Welcome to your home in Winter Haven—just minutes from Legoland, shopping, medical facilities, and Highway 27 for easy commuting! Originally a 3-bedroom, 2-bath layout, this home has been converted into a spacious 5-bedroom, 2-bath residence, offering incredible versatility for growing families, multigenerational living, or those needing extra space for a home office or hobby rooms. It will need some TLC due to tenant being in property. With five true bedrooms, everyone in the family can have their own retreat while still enjoying generous shared living spaces. Outside, you’ll find a property ideally situated for convenience—whether you’re heading to Legoland for weekend fun, accessing everyday amenities just minutes away, or commuting via Highway 27. This home offers the perfect blend of location, and space in one of Winter Haven’s most desirable areas.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Brandy Duncan (863-585-6849)
689 VITTORIO DR, WINTER HAVEN, FL 33884
$315,000189 Days on yellowkey MLS ID: O6353926
2 Days Off yellowkey (back on 1/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2053 Built: 2021Monthly Fee: $19 Tax: $5,951 (2025)Community: Villamar Ph 2Single Family
Taxes:$5,951
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Tax Year: 2025
Middle School: Mclaughlin Academy Of Excellence
Remarks: Under contract-accepting backup offers. Welcome to the Serendipity floor plan — where comfort meets style! This stunning three-bedroom, den, two-bathroom home offers the perfect blend of modern design and everyday convenience. Step inside to find a bright, open-concept layout featuring high vaulted ceilings, a spacious great room, a beautifully appointed kitchen with a large island and walk-in pantry, and a cozy dining area ideal for gatherings. The owner’s suite provides a peaceful retreat with dual walk-in closets and a luxurious en-suite bath. The flexible den is perfect for a home office, guest space, or hobby room, offering versatility to fit your lifestyle. Enjoy year-round outdoor living in the beautiful enclosed lanai overlooking the fully fenced backyard—perfect for relaxing or entertaining in privacy. Located in a highly desirable area, this home offers convenient access to top-rated schools, shopping, dining, parks, and houses of worship. Designed for both elegance and functionality, the Serendipity truly lives up to its name—a happy discovery of the place you’ll love to call home.
Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)
Listing Agent: Kelly Martinez (407-864-8965)
5171 KINSLEY DR, WINTER HAVEN, FL 33884
$339,999252 Days on yellowkey MLS ID: S5133352
INCREASED by $3,100 (0.9%) on 04/21/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2050 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Elementary School: None
High School: None
Middle School: None
Remarks: An inviting covered entry welcomes guests to this inspired Tarragon home. Pass two bedrooms, a shared bath, a flex room and a laundry on your way to a spacious great room with an adjacent covered patio. The well-appointed kitchen boasts a center island, a walk-in pantry and a dining nook. Showcasing a generous walk-in closet and an attached bath with double sinks. An additional bedroom and bathroom round out this inspired plan. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
5135 KINSLEY DR, WINTER HAVEN, FL 33884
$314,999342 Days on yellowkey MLS ID: S5127745
REDUCED by $951 (0.3%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: Discover this must-see Ruby home. Included features: an inviting covered entry; a well-appointed kitchen offering 42" white cabinets, a walk-in pantry and a center island; an elegant dining room; a spacious great room; a lavish primary suite showcasing a generous walk-in closet and a private bath; a laundry and a covered patio. This could be your dream home! *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
3820 TRADITIONS BLVD N, WINTER HAVEN, FL 33884
$380,00035 Days on yellowkey MLS ID: P4938275
0 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2400 Built: 2006Monthly Fee: $485 Tax: $2,300 (2025)Community: Traditions Ph 01Spa: NoSingle Family
Taxes:$2,300
Remarks: This stunning property is situated on a premium lot, offering picturesque views of the pond. Featuring a highly desirable split-bedroom floor plan, this partially furnished home includes three bedrooms and two baths. As you step inside, you're welcomed by a charming screened-in front porch with a leaded glass door and transom window. The kitchen boasts 42" upper maple wood cabinetry, accented with braided trim, crown molding, and convenient pull-out drawers. Recent updates include a new refrigerator and microwave, along with a closet pantry. Enjoy casual meals at the breakfast bar or in the cozy breakfast nook. The open-concept design seamlessly connects the formal dining room and living room, both of which showcase stunning pond views. The spacious great room is bright and inviting, featuring high ceilings and vinyl plank flooring. Architectural details like arched entryways, crown molding, and decorative niches enhance the home's elegant atmosphere. The four-seasons room, lined with large windows, allows you to enjoy the scenic views year-round. The generously sized primary bedroom suite serves as a private retreat, complete with plantation shutters and a cozy sitting area. Dual walk-in closets with overhead luggage shelves offer ample storage. The primary bathroom features a comfort-height vanity with double sinks, a linen closet, a seated walk-in shower, a water closet, and a luxurious garden tub. For outdoor enjoyment, the expansive screened-in lanai provides a peaceful space to relax. Additional features include a laundry room with a washer, dryer, utility sink, and extra cabinetry, solid surface flooring throughout, a water heater (installed in 2024), an upgraded HVAC system with an Aprilaire electronic filtration system, custom window treatments, an invisible dog fence, and a five-zone irrigation system with an irrigation meter. The home also boasts an architectural shingle roof (installed in 2019), professionally landscaped corner lot, pull-down attic stairs, alarm system, gutters, exterior lighting, paved walkway and driveway, and a two-car garage with shelving and a garage door opener. Residents of Traditions enjoy a wealth of amenities, including a lakefront clubhouse with a dock and boat ramp, heated swimming pool and spa, ballroom, billiards, meeting rooms, library, computer room, craft room, dog park, and courts for tennis, pickleball, basketball, bocce ball, and shuffleboard. The community also offers a fitness center, aerobics studio, and more. Conveniently located near shopping, dining, major routes, and Legoland, this home offers an exceptional lifestyle. The monthly HOA fee covers exterior house painting, cable, internet, lawn service, and clubhouse amenities, ensuring a maintenance-free living experience.
Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)
Listing Agent: Eileen Belanger (863-221-0229)
4612 REYNOSA DR SW, WINTER HAVEN, FL 33880
$320,000270 Days on yellowkey MLS ID: V4944212
1 Days Off yellowkey (back on 4/21/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1716 Built: 1984 Tax: $4,573 (2024)Community: Plaza SubSingle Family
Taxes:$4,573
Elementary School: Lake Shipp Elem
Middle School: Westwood Middle
Remarks: Under contract-accepting backup offers. Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Trent Shackelford (941-518-7875)
1658 TEAGAN LN, WINTER HAVEN, FL 33884
$315,99026 Days on yellowkey MLS ID: S5146407
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1933 Built: 2024Monthly Fee: $16 Tax: $4,170 (2025)Community: Peace Creek ReserveSingle Family
Taxes:$4,170
Elementary School: Wahneta Elem
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful home in peace creek reserve! this thoughtfully designed single-story residence offers 4 bedrooms and 2.5 bathrooms, combining comfort and functionality. The open-concept floor plan seamlessly connects the family room, dining area, and kitchen—complete with a central island—creating the perfect space for everyday living and entertaining. Located in the desirable peace creek reserve community, residents enjoy a serene setting surrounded by nature, including a picturesque creek. situated in winter haven—known as the chain of lakes city with over 26 connected lakes—this area offers a variety of shopping, dining, and outdoor activities such as biking and water recreation. Peace creek reserve provides the perfect balance of a peaceful, small-town atmosphere with everyday convenience—an ideal place to call home.
Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)
Listing Agent: Barbara Cunha De Freitas (617-458-0838)
3863 BEDFORD AVE, WINTER HAVEN, FL 33884
$345,00027 Days on yellowkey MLS ID: O6396509
REDUCED by $10,000 (2.8%) on 04/16/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1797 Built: 2017Monthly Fee: $485 Tax: $4,293 (2025)Community: Traditions Ph 02Single Family
Taxes:$4,293
Remarks: As you walk into this beautiful home, you are welcomed by a den/office on the right with double doors, which can easily be used as a third bedroom if desired. Continuing through the home, you’ll find a spacious formal dining room separate from the main living area. As you exit the dining room, the home opens up into a bright open-concept space featuring the living room, kitchen, and a cozy coffee/breakfast area, perfect for everyday living and entertaining. The gourmet kitchen features upgraded Kraft Maid cabinetry, Cambria quartz countertops, newer KitchenAid appliances, and a gas convection range, all overlooking the spacious living room with large windows and sliding glass doors that bring in plenty of natural light. The home offers three sliding glass doors that lead out to a large screened-in lanai, perfect for relaxing and enjoying the Florida lifestyle. The lanai also features an extended screened area with artificial turf. The spacious primary bedroom includes a walk-in California closet system and an en-suite bathroom with dual sinks, comfort-height vanity, separate toilet room, and a walk-in tiled shower. Throughout the home you will find crown molding, imported Italian tile flooring, engineered wood flooring, plantation shutters, and Hunter Douglas remote-control shades. Additional features include a laundry room with washer and dryer, double-pane low-E windows, an AO Smith hybrid water heater, Pelican salt-free water filtration system, gutters, and a stone exterior façade with a brick paver driveway and extended front walkway. The two-car garage features an insulated garage door, garage door opener, overhead storage racks, and a workbench area with pegboard and additional workspace. Located in the desirable Traditions 55+ gated community, residents enjoy resort-style amenities including a clubhouse, heated pool and hot tub, ballroom, craft room, meeting rooms, library, computer room, fitness center, tennis and pickleball courts, dog park, and more. Monthly HOA fees include lawn service, cable TV, internet, and exterior house painting.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Stephanie Class Cordero (321-208-0378)
2775 SAN MARCO WAY, WINTER HAVEN, FL 33884
$332,99014 Days on yellowkey MLS ID: O6400845
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1564 Built: 2026Monthly Fee: $193 Tax: $3,035 (2025)Community: Villamar Ph 5Single Family
Taxes:$3,035
Remarks: Pre-Construction. To be built. Discover a home where modern comfort meets effortless style in the beautiful VillaMar community of Winter Haven. Surrounded by scenic lake views and resort-style amenities, this is more than a place to live—it’s a place to truly enjoy life. The Ventura floor plan offers up to 1,562 square feet of thoughtfully designed living space with 4 bedrooms and 2 bathrooms. At the heart of the home, the open-concept layout creates a bright and welcoming atmosphere. The beautifully designed kitchen features a large island with quartz countertops—perfect for gathering, entertaining, or enjoying everyday meals. It flows seamlessly into the spacious great room, where natural light pours in through upgraded windows, creating a warm and airy feel throughout. Your private primary suite, located at the rear of the home, offers a peaceful retreat. Enjoy a spacious walk-in closet, dual sinks, and a walk-in shower designed for both relaxation and ease. There are three other bedrooms and a full bath are tucked away at the front of the home, creating a private and functional space. Built with today’s lifestyle in mind, The Ventura includes smart home features such as a Ring Video Doorbell, Smart Thermostat, Keyless Entry Door Lock, and customizable DEAKO light switches—giving you control and peace of mind at your fingertips. Enjoy the amenities offered in the community with a resort style pool, playground and dog park. Experience the perfect blend of style, convenience, and community living at VillaMar. Your future home is waiting—make The Ventura your own and start creating lasting memories.
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Vilmari Caraballo (407-583-9870)
528 CODY CALEB DR, WINTER HAVEN, FL 33884
$304,50014 Days on yellowkey MLS ID: L4961233
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2250 Built: 2005Monthly Fee: $23 Tax: $4,538 (2025)Community: Savannah EstatesSingle Family
Taxes:$4,538
Remarks: Very clean and well-maintained 4 bedroom, 2.5 bathroom two-story home located in desirable SE Winter Haven! Roof is only 2 years old!! This spacious property offers a functional layout perfect for both everyday living and entertaining. The large kitchen opens seamlessly to the family room, creating a welcoming central gathering space, and features ample oak cabinetry for plenty of storage. Ceramic tile flooring is featured in all wet areas for easy maintenance. Step outside to enjoy the fully fenced backyard—ideal for pets, play, or relaxing in your own private outdoor space. Conveniently located with quick access to Hwy 27 and a straight drive to I-4, making commuting a breeze. Just minutes from shopping, dining, and entertainment, including Eagle Ridge Mall, the Cypress Gardens area, and Legoland. Don’t miss this opportunity to own a spacious home with room to grow in a great location!
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Tony Acosta (863-224-5956)
123 ELOISE OAKS DR, WINTER HAVEN, FL 33884
$390,00033 Days on yellowkey MLS ID: L4960769
1 Days Off yellowkey (back on 4/20/2026)
REDUCED by $5,000 (1.3%) on 04/16/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2029 Built: 2018Monthly Fee: $56Community: Eloise OaksSpa: NoSingle Family
Elementary School: Pinewood Elem
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2018, offering the perfect blend of modern comfort and Florida lifestyle living. From the moment you step inside, you’ll appreciate the open-concept layout, ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, featuring contemporary finishes, ample cabinetry, and plenty of natural light throughout. The living area is enhanced by a stylish built-in electric fireplace, creating a warm and inviting focal point. This thoughtfully designed single-story home features a spacious primary suite with a private bath and walk-in closet, along with three additional bedrooms that offer flexibility for family, guests, or a home office. Step outside and enjoy your private backyard space—perfect for relaxing evenings or weekend gatherings. The garage is equipped with a mini-split air conditioning system, adding comfort and versatility for a workspace, gym, or additional storage. Located in a desirable community with private access to Lake Eloise, part of the renowned Winter Haven Chain of Lakes, you’ll have endless opportunities for boating, fishing, and enjoying the water just minutes from your doorstep. Plus, you’re just 10 minutes from LEGOLAND Florida Resort, making this location perfect for both everyday convenience and fun-filled weekends. Conveniently situated near shopping, dining, and major roadways, this move-in-ready home offers the ideal combination of location, lifestyle, and value. Schedule your private showing today and experience everything this home has to offer!
Listing is courtesy of: CLARK REALTY LLC (863-345-2155)
Listing Agent: Ty Dennis (863-651-8328)
1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880
$344,90017 Days on yellowkey MLS ID: L4961188
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2009Monthly Fee: $50 Tax: $4,839 (2025)Community: Normandy HeightsSingle Family
Taxes:$4,839
Remarks: Welcome to this stunning 4-bedroom, 3-bath split floor plan home with tile flooring throughout. The open kitchen features a breakfast bar, brand-new stainless steel appliances, and plenty of storage. You’ll love the formal living room and a dedicated laundry room. Sliders from both the master suite and living room lead to a peaceful lanai. The master bath boasts dual sinks, a garden tub, and a separate shower. Plus, one of the bathrooms conveniently opens to the lanai. The lanai floor and garage floor was recently painted for that added style. The home is located in Winter Haven in between Orlando and Tampa close to all of the amenities you would need. Don’t miss this gem!
Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)
Listing Agent: Annie Wood (321-229-1913)
5445 CHANDLER DR, WINTER HAVEN, FL 33884
$319,50048 Days on yellowkey MLS ID: S5146003
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3010 Built: 2006Monthly Fee: $48 Tax: $5,827 (2025)Community: Bentley PlaceSingle Family
Taxes:$5,827
Remarks: Welcome to 5445 Chandler in Winter Haven—a great opportunity for buyers looking to add their own personal touch! This home offers generous square footage and plenty of living space, giving you room to spread out, entertain, or reimagine the layout to fit your needs. The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you’ll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential. While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own. Conveniently located near shopping, dining, and Winter Haven’s beautiful lakes, this property offers both space and opportunity. If you’re looking for a home with room to grow and the ability to add value, this is one you won’t want to miss!
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)
Listing Agent: Jacob Hara (407-933-5478)
3890 BEDFORD AVE, WINTER HAVEN, FL 33884
$395,00016 Days on yellowkey MLS ID: L4961088
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2322 Built: 2019Monthly Fee: $485 Tax: $5,156 (2025)Community: Traditions Ph 02Spa: NoSingle Family
Taxes:$5,156
Remarks: Welcome to TRADITIONS, an active 55+ gated community located in the heart of the state on Lake Ruby. From swimming laps in the olympic size pool, casting a line at the lake, swinging a pickleball racquet or utilizing the fitness room and scheduled classes, there is plenty to do to stay in shape. If you prefer a more relaxed day, the clubhouse provides plenty of social spaces for card games, crafting, puzzles and reading a book. The community has planned monthly activities, they even plan a yearly community cruise if that's your vibe. You don't need to leave the community to find something to do, however; Disney and Universal Studios are nearby and you can reach either coast in less than two hours. The community is close to shopping (Publix coming soon), medical facilities, Legoland and the quaint downtown area of Winter Haven with boutique shops and local restaurants. This community is truly the ultimate 55+ lifestyle. The monthly dues include: community amenities, Spectrum cable and internet, lawn maintenance, common area maintenance, and exterior paining every 8 years. Now for the house: This is a Kennedy model floorplan, one of the most sought after in this community. It is a SHOW STOPPER from top to bottom and these Sellers have executed great care during their ownership. You will appreciate some of the additions they have made such as the extended rear screened lanai with Coolaroo shades and a motorized hurricane shutter. They also extended a paver BBQ area for those who like to grill. They added overhead storage racks in the garage and if you are an angler you will appreciate the storage system for the fishing poles! They have also added a motorized screen door for the days that you want to tinker in the garage and keep the bugs out. The exterior was just painted in 2025. The lawn is manicured with professional landscape edged flower beds and best of all the grass is maintained by the HOA. Step inside the front door to be instantly impressed with the high ceilings. The space is open enough for great entertaining but also offers space to spread out when needed. Ceramic tile in all the wet areas and living spaces with 5 inch baseboards and crown molding give the feeling of luxury. Recessed lighting, pendant lights as well as good window placement bring good lighting into the space. The kitchen is spectacular. 42 inch upper cabinets, quartz counters, walk in pantry and preparation island make the space functional for the chef and easy to entertain in. There are three dining space choices: formal dining area, breakfast nook and a breakfast bar providing with plenty of seating. The living room flows perfectly from the triple sliding door onto the lanai. The wall mounted TV's convey. The floorplan also offers a triple split bedroom plan. The primary bedroom offers an ensuite and the walk in closet has custom built in shelving. The ensuite has dual sinks, private commode room, linen closet and soaking tub. The walk in shower has no step and has nice glass doors. The 2nd and 3rd bedrooms share a guest bath with dual sinks and the 4th bedroom has a private ensuite. You truly have to see this home to appreciate its flow, style, tidiness and all the features that make this place a HOME! If 55+ living in Florida is what you have been dreaming of, you just found it! Come make some new Traditions!
Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)
Listing Agent: Christie Weeks (863-450-7973)
6337 BOTTICELLA BLVD, WINTER HAVEN, FL 33884
$332,71016 Days on yellowkey MLS ID: W7884986
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2370 Built: 2026Monthly Fee: $19Community: Villa MarSingle Family
Remarks: Quick Move-in! Introducing Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. The Windermere single-family home is where you want to be. Step in from the 2-car garage and enjoy the good life. Find it in the large family room, where smiling faces greet you and delicious smells fill the gourmet kitchen. Share stories around the island or outside on the lanai. The 1st floor also features a study. Upstairs, 3 bedrooms and a full bath provide privacy while a loft adds extra entertaining space. Your deluxe owner’s suite includes double vanities, a seated shower and a walk-in closet, making The Windermere can’t-miss. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat. **Closing cost assistance is available with use of Builder’s affiliated lender**. DISCLAIMER: Prices, financing, promotion, and offers subject to change without notice. Offer valid on new sales only. See Community Sales and Marketing Representative for details. Promotions cannot be combined with any other offer. All uploaded photos are stock photos of this floor plan. Actual home may differ from photos.
Listing is courtesy of: MALTBIE REALTY GROUP (813-819-5255)
Listing Agent: Bill Maltbie (813-819-5255)
292 MEREDITH BLVD, WINTER HAVEN, FL 33881
$329,990111 Days on yellowkey MLS ID: G5106667
0 Days Off yellowkey (back on 4/19/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2110 Built: 2025Monthly Fee: $75 Tax: $500 (2025)Community: Willowbrook NorthSingle Family
Taxes:$500
Elementary School: Fred G. Garnier Elem
Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning 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 2110 sq feet of living space and provides excellent curb appeal in its elevation. Inside, you will find gorgeous White cabinets complemented by sleek quartz countertops 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: Cindy Sapp (352-516-2843)
4669 OSPREY WAY, WINTER HAVEN, FL 33881
$319,50016 Days on yellowkey MLS ID: R4911042
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1992 Built: 2019Monthly Fee: $35 Tax: $5,100 (2025)Community: St James XingSingle Family
Taxes:$5,100
Elementary School: Walter Caldwell Elem
High School: Auburndale High School
Remarks: This 4/2 home has a renovated interior showcasing modern upgrades throughout. The home features stunning new 36" x 24" porcelain tile flooring, offering a sleek, contemporary look with durability and easy maintenance. Move-in ready and designed for comfortable, stylish living. Dual access bedroom and bath provides the bedroom with private ensuite access while allowing the bathroom to serve as a main or guest bathroom from the hall, featuring two doors to maximize access and functionality. Large kitchen with island and lots of cabinet space and large pantry. Sliding doors leading to covered screened in porch with additional concreted tiled patio area that leads to a large backyard.
Listing is courtesy of: EASY REALTY (321-895-4636)
Listing Agent: Greg Owen
441 MCKENNA DR, WINTER HAVEN, FL 33881
$363,00024 Days on yellowkey MLS ID: O6398240
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2360 Built: 2021Monthly Fee: $17 Tax: $6,548 (2025)Community: Lucerne Park ReserveSingle Family
Taxes:$6,548
Remarks: One or more photo(s) has been virtually staged. Welcome to 441 McKenna Dr, a well-maintained 4-bedroom, 2.5-bath home in the Lucerne Park Reserve community, where modern design, energy efficiency, and everyday functionality come together in a comfortable Winter Haven setting. From the moment you enter, the home feels bright and open, featuring a clean, neutral palette and durable tile flooring throughout the main living areas. The open-concept layout seamlessly connects the kitchen, dining, and living spaces, creating an ideal environment for both daily living and entertaining. Here is a clean, MLS-appropriate disclaimer you can use: --- All information provided is deemed reliable but is not guaranteed and should be independently verified by buyers and their agents. Room dimensions are approximate and should be measured for accuracy. HOA fees, rules, and restrictions are subject to change and must be confirmed directly with the association. Information regarding the solar system, roof, utilities, and other property features is based on seller representations and has not been independently verified. Listing broker and seller make no warranties, expressed or implied, as to the accuracy of the information provided. The kitchen serves as the heart of the home, showcasing white cabinetry, stainless steel appliances, quartz countertops, ample prep space, and a central island that naturally brings everyone together. The living area is enhanced by a decorative feature wall with a fireplace focal point, adding character and visual interest beyond standard finishes. Large sliding glass doors invite in natural light and provide direct access to the fenced backyard, offering a versatile outdoor space for relaxing, entertaining, or pets. The primary suite features a spacious bathroom with dual sinks, quartz countertops, a glass-enclosed shower, and built-in shelving for added storage and convenience. Additional bedrooms offer flexibility for guests, a home office, or hobbies, while the half bath provides added convenience for visitors. A dedicated laundry room further enhances the home's functionality. This home also includes smart outlet features compatible with Alexa, allowing for convenient voice-controlled functionality and adding a modern smart-home element that enhances everyday living. One of the standout features is the seller-reported solar panel system, designed to produce 100% of the home’s energy consumption. According to the seller, the electric bill is typically around $40 or less per month, reflecting primarily the grid connection charge. The seller will also pay for the solar transfer, adding significant long-term value. Additionally, the seller reports a new roof installed in 2024. Located in Lucerne Park Reserve, residents enjoy access to community amenities including a pool, playground/tot lot, and scenic lakes. The Winter Haven location offers convenient access to shopping, dining, healthcare, schools, and local attractions including LEGOLAND Florida Resort. This property offers a compelling combination of modern features, energy efficiency, and community living—making it an excellent opportunity for buyers seeking both comfort and long-term value. One or more photo(s) has been virtually staged.
Listing is courtesy of: NEXTHOME MY WAY (407-544-4545)
Listing Agent: Angel Pabon (407-544-4545)
2352 TWIN LAKE VIEW RD, WINTER HAVEN, FL 33881
$314,90057 Days on yellowkey MLS ID: L4960041
REDUCED by $2,500 (0.8%) on 04/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1994 Built: 2020Monthly Fee: $23 Tax: $4,127 (2025)Community: Eagle CrestSingle Family
Taxes:$4,127
Elementary School: Elbert Elem
Remarks: Welcome to this beautiful 3-bedroom, 2-bathroom home in the heart of Winter Haven! Featuring a desirable open floor plan, this home offers comfortable living with plenty of space to relax and entertain. The modern kitchen is highlighted by granite countertops, ample cabinetry, large island, and a seamless flow into the main living area, making it perfect for gatherings. Just off the entrance, you’ll find a versatile flex space that can easily serve as a home office, dining room, or playroom to suit your needs. The spacious primary suite is a true retreat, complete with a large bedroom and dual master closets, offering plenty of storage. Two additional bedrooms and a second full bathroom provide comfortable accommodations for family or guests. Step outside from the large sliding doors to enjoy the fenced-in backyard, ideal for pets, outdoor activities, or relaxing evenings. Located in a great neighborhood in the heart of Winter Haven, this home is conveniently close to shopping, restaurants, and local schools, offering both comfort and convenience. Don’t miss the opportunity to make this wonderful home yours!
Listing Agent: Bethany Jack (606-584-0518)
239 GOLF AIRE BLVD, WINTER HAVEN, FL 33884
$399,000179 Days on yellowkey MLS ID: P4936940
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2263 Built: 1998Monthly Fee: $500 Tax: $2,634 (2024)Community: Lake Bess Country CcSingle Family
Taxes:$2,634
Elementary School: Frank E. Brigham Academy
Remarks: SIGNIFICANT PRICE IMPROVEMENT | LOWERED 26,000.00 BEAUTIFUL GATED GOLF COURSE COMMUNITY An exceptional opportunity to own a beautiful 3brm/2.5 bath home nestled on the 4th hole of the highly sought-after Lake Bess Country Club and Golf Course in Winter Haven. As you step inside, you are welcomed by a charming foyer featuring 10-ft ceilings that create an open and airy ambiance throughout the home. The living room, enhanced by a cozy gas fireplace, provides a perfect setting for those cool winter evenings in Florida. This space effortlessly connects to a spacious breakfast nook, both of which open onto a large lanai that offers tranquil views of the golf course, framed by majestic oak trees draped in moss-ideal for an evening glass of wine. Through French doors off the living room, you will find a stunning study\office equipped with built -in wood shelving with additional storage, perfect for work or leisure. The layout thoughtfully includes two generous sized bedrooms and a full bath on this side of the home. At the heart of the house, the well-appointed kitchen is a dream for any cook. It boasts ample space, views of the golf course, and a breakfast nook for casual dining. A bar area allows friends and family to gather and socialize while meals are being prepared. For more formal occasions, the designated dining room offers an elegant setting. The primary suite is an impressive retreat, featuring a tray ceiling, his and hers walk-in closets, and a spacious bathroom equipped with a large shower and vanity. A private water closet and a hidden washer and dryer behind closet doors add to the convenience of this remarkable space. The home also includes an oversized 2-car garage, perfect for tools and a work table. As part of this vibrant community, you'll enjoy access to the clubhouse, community pool and golf course. This hidden gem offers easy access to Legoland, Highway 27, and I-4, making it a prime location for both relaxation and adventure. The purchase price also includes 1 of 49 shares to the golf club which includes 2 free memberships and unlimited Golfing, enhancing the value of this exceptional property. I invite you to discover this property and envision the lifestyle that awaits you at Lake Bess Country Club. Please let me know if you would like to schedule a viewing or if you have any questions.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Christina Ashley (941-780-0291)
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