Location: Winter Haven
Keyword(s): Westwood Middle
Keyword(s) Middle School: Westwood Middle
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2500 21ST ST NW #88, WINTER HAVEN, FL 33881
$198,00046 Days on yellowkey MLS ID: P4937851
3 Days Off yellowkey (back on 3/31/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1585 Built: 1976Monthly Fee: $467 Tax: $2,419 (2024)Community: Casa Del Sol Condo Village Ph 01Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,419
Elementary School: Fred G. Garnier Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Westwood Middle
Remarks: Under contract-accepting backup offers. Price Improvement Chain of Lakes Frontage on Lake Hartridge Enjoy true waterfront living in this beautifully updated 3-bedroom, 2.5-bath townhome-style condo located directly on Lake Hartridge, part of the renowned Winter Haven Chain of Lakes. Situated in the desirable Casa Del Sol community, this spacious two-story home offers direct lake access and stunning panoramic views. The interior features wood laminate and tile flooring, a formal dining room, updated kitchen with stainless steel appliances and solid surface countertops, and a large living room overlooking the water. Relax in the Florida room or enjoy sunrise and sunset views from your screened lakefront lanai. Upstairs, the generous primary suite includes a walk-in closet, ensuite bath with granite counters, and a private enclosed balcony with breathtaking lake views. Two additional bedrooms, full bath, and upstairs laundry complete the layout. An attached 2-car garage adds convenience. Community amenities include a lakefront recreation area, pool, clubhouse, tennis courts, and private dock. HOA covers water, lawn care, and full access to amenities.Experience maintenance-free living with true Chain of Lakes frontage and endless boating, fishing, and waterfront enjoyment.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Irene Bryan (863-289-6789)
3952 WARBLER DR, WINTER HAVEN, FL 33880
$284,995Listed 03/31/2026 12:43PM MLS ID: S5146840
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2101 Built: 2005Monthly Fee: $12 Tax: $4,019 (2025)Community: Queens Cove Ph 04Single Family
Taxes:$4,019
Elementary School: Eagle Lake Elem
High School: Lake Region High
Tax Year: 2025
Remarks: Welcome Home to Queens Cove! This stunning 4 bedroom, 2 bathroom home is located in the highly desirable community of Queens Cove in Winter Haven. NO CDD and low HOA. Minutes from Legoland, hospitals, shopping centers and mayor highways. Don't miss your opportunity to own an affordable home in the heart of Winter Haven. Schedule your showing today!
Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)
Listing Agent: Harrison Perez Collazo (787-365-8967)
349 HONEY BELL RD, WINTER HAVEN, FL 33880
$260,00012 Days on yellowkey MLS ID: TB8458757
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1535 Built: 2019Monthly Fee: $56 Tax: $2,732 (2024)Community: Squires GroveSingle Family
Taxes:$2,732
Elementary School: Pinewood Elem
Remarks: Welcome to this charming and well-maintained home in the heart of Winter Haven! Situated on a spacious lot, this property offers a perfect blend of comfort and functionality with an open-concept layout, abundant natural light, and inviting living spaces. The kitchen features ample cabinetry and flows seamlessly into the main living area, making it ideal for both everyday living and entertaining. Enjoy a generously sized backyard with plenty of room for outdoor activities, gardening, or relaxing in your own private space. Conveniently located near shopping, dining, schools, and major roadways, this home provides both tranquility and accessibility. A fantastic opportunity for homeowners or investors alike—schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Bridd Bone (727-798-1918)
1731 AVENUE C NE, WINTER HAVEN, FL 33881
$380,000131 Days on yellowkey MLS ID: S5138718
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1619 Built: 1952 Tax: $2,668 (2025)Community: Elbert AcresSingle Family
Taxes:$2,668
Elementary School: Elbert Elem
High School: Chain of Lakes Collegiate High
Remarks: Exclusive property in Winter Haven featuring a 4-bedroom main home, private pool, independent studio, and parking for up to 6 cars. Located in a peaceful and welcoming city known for its beautiful lakes and excellent quality of life, this property offers comfort, space, and great potential. The main house includes 4 spacious bedrooms, 2 beautifully updated bathrooms, a fully renovated kitchen with an island and pool views, open-concept living and dining areas, and bright, inviting spaces throughout. Enjoy your own private pool, perfect for relaxation and entertainment. The independent studio is ideal for rental income, guests, or family use, and offers an integrated living/sleeping area, a full kitchen with stove, microwave, and dishwasher, a private bathroom, and its own laundry space. Conveniently located between Orlando and Tampa, Winter Haven provides access to numerous lakes for recreation and water sports, a quiet and safe community, and proximity to schools, shopping, dining, and essential services. Don’t miss this unique opportunity—schedule your visit today!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Paola Millan (407-452-7034)
530 SANCTUARY BLVD, WINTER HAVEN, FL 33881
$639,90039 Days on yellowkey MLS ID: S5144344
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3619 Built: 2023Monthly Fee: $83 Tax: $7,594 (2025)Community: Sanctuary By The Lake Ph OneSingle Family
Taxes:$7,594
Elementary School: Lake Alfred Elem
High School: Auburndale High School
Remarks: Welcome to this exceptional custom-built 2023 luxury residence located within the gated community of Sanctuary by the Lake, where modern elegance, thoughtful design, and everyday comfort come together seamlessly. Perfectly positioned on a spacious corner lot directly across from the lake, this stunning home immediately impresses with its commanding presence and refined architectural detail. Step through the beautiful double front doors and experience an immediate sense of openness, highlighted by soaring ceilings, abundant natural light, and expansive living spaces designed to feel both grand and inviting. With over 3,600 square feet of living space, the thoughtfully designed open layout effortlessly connects formal and casual living areas, creating an ideal setting for both entertaining and relaxed daily living. At the heart of the home lies a beautifully appointed chef’s kitchen, featuring granite countertops, upgraded stainless steel appliances, a breakfast bar, walk-in pantry, and generous prep space, perfect for hosting gatherings or enjoying quiet mornings at home. The kitchen flows naturally into the impressive great room and dining areas, enhancing the home’s seamless indoor living experience. One of the standout features is the oversized covered and enclosed Florida room, custom added by the owners to extend the living space year-round. Whether hosting celebrations, entertaining guests, or simply unwinding while enjoying peaceful surroundings, this space truly elevates the lifestyle this home offers. Designed with privacy in mind, the desirable triple split floor plan includes 4 spacious bedrooms, 3 full bathrooms, and a dedicated private office, ideal for remote work or flexible living needs. The luxurious primary suite serves as a private retreat, complete with dual vanities, a garden tub, separate walk-in shower, makeup vanity, and a very generous walk-in closet. Beautiful luxury vinyl plank flooring flows throughout the main living areas, complemented by tasteful finishes and quality craftsmanship that reflect the home’s custom construction. A well-equipped laundry room with cabinetry, countertop workspace, and sink adds everyday convenience. A 50 amp generator port was added for peace of mind. Beyond the home itself, the location offers the best of Central Florida living. Just minutes from downtown Winter Haven, residents enjoy award-winning restaurants, local boutiques, parks, and year-round entertainment, while nearby access to Lakeland and I-4 provides an easy commute to both Tampa and Orlando. Florida’s Atlantic and Gulf beaches are approximately 90 minutes away, making weekend coastal escapes effortlessly accessible. This is more than a home, it is a refined living experience combining space, luxury, and lifestyle within one of Winter Haven’s most desirable gated communities.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
900 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$469,9004 Days on yellowkey MLS ID: S5146723
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1828 Built: 1948 Tax: $4,023 (2025)Community: East View PkwySingle Family
Taxes:$4,023
Elementary School: Auburndale Central Elem
Remarks: Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, and unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding, and paddleboarding right from your backyard. With nearby slalom courses and open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds and other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms and 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort and privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with it's oversized driveway and an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining, and entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play, and unwind in one of Florida’s most iconic lakefront settings. Book your showing today!
28 CASARENA CT, WINTER HAVEN, FL 33881
$195,0009 Days on yellowkey MLS ID: S5146381
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 2045 Built: 1989Monthly Fee: $26 Tax: $3,928 (2025)Community: Casarena On LakesTownhouse
Taxes:$3,928
Remarks: Welcome to this charming two-story townhome located in the Casarena gated community in Winter Haven, offering 2 bedrooms and 2.1 bathrooms designed for comfort and flexibility. The inviting main living area features a cozy fireplace, perfect for relaxing or entertaining, while the functional layout flows seamlessly into the dining and kitchen spaces. Upstairs, enjoy your own private second-floor balcony—an ideal spot for morning coffee or unwinding in the evening. Enjoy family gatherings in the large screened in patio that is ready to be converted into your ideal outdoors living space. Additional highlights include a convenient laundry closet in the garage and ample storage throughout. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this home checks all the boxes—schedule your private showing today and make it yours! This home is being sold in As Is condition. All buyers must view the home before submitting an offer.
Listing is courtesy of: REALTYCITY INC (863-438-6605)
Listing Agent: Jesse Carriedo (863-438-6605)
2154 CHRIS DR, WINTER HAVEN, FL 33884
$285,49037 Days on yellowkey MLS ID: O6384811
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1880 Built: 2025Monthly Fee: $16 Tax: $32 (2024)Community: Peace Creek Reserve 40'SSingle Family
Taxes:$32
Elementary School: Wahneta Elem
Remarks: One or more photo(s) has been virtually staged. Under Construction. Beautiful Corner Lot!! This expansive two-story Columbus has a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient two-car garage. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.
Listing is courtesy of: LENNAR REALTY (800-229-0611)
Listing Agent: Ben Goldstein (407-310-7677)
920 SUMMER GLEN DR, WINTER HAVEN, FL 33880
$294,00029 Days on yellowkey MLS ID: L4959598
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1846 Built: 2020Monthly Fee: $25 Tax: $2,839 (2025)Community: Coventry Cove Ph IiSingle Family
Taxes:$2,839
Elementary School: Lake Shipp Elem
Remarks: This home delivers the perfect blend of comfort and style with an open concept design and thoughtfully defined spaces. The heart of the home is the kitchen featuring plenty of cabinetry and counter space that connects seamlessly to the dining and living areas. Large windows fill the home with natural light creating an airy feel throughout. The primary suite offers a spacious layout and ensuite bath. Additional bedrooms provide flexibility for guests, a home office, or growing needs. Enjoy outdoor living in the backyard with room to personalize and make it your own.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Roderick Small (863-712-0657)
961 DREXEL AVE NE, WINTER HAVEN, FL 33881
$320,00037 Days on yellowkey MLS ID: L4959592
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1856 Built: 1948 Tax: $3,409 (2025)Community: Anna MarSingle Family
Taxes:$3,409
Elementary School: Inwood Elem
Remarks: ***HUGE PRICE DECREASE***This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Lisa Ford (863-510-3890)
2145 RIVER HAWK LOOP, WINTER HAVEN, FL 33880
$349,90035 Days on yellowkey MLS ID: S5143804
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1905 Built: 2026Monthly Fee: $98 Tax: $228 (2025)Community: Residences At Winter HavenSingle Family
Taxes:$228
Remarks: Located in the new Residences at Winter Haven community, this home features the Everglades model floor plan, designed with an open-concept layout that maximizes natural light and functionality. The home backs directly to the community pond, offering water views and added privacy. Built with double-pane insulated windows and constructed in compliance with the current Florida Building Energy Efficiency Code, the home offers modern efficiency standards. Residences at Winter Haven is a newly developed single-family home community conveniently located near shopping, dining, major roadways, and everyday conveniences. There is a natural ease to this home, from the open layout to the thoughtful finishes. The 8-foot doors and premium flooring flow throughout the main living areas, creating a clean and consistent feel. In the kitchen, the focus is on quality and gathering, highlighted by a large waterfall island and 42” cabinetry with crown molding. It’s a home designed for both quiet mornings and hosting friends, with an open living area that leads out to a covered lanai. It’s a clean, modern space that’s ready for you to make it your own. A model home is available for on-site visits within the community.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)
207 24TH CT SW, WINTER HAVEN, FL 33880
$285,00075 Days on yellowkey MLS ID: L4958315
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1976 Tax: $4,614 (2025)Community: West Of Lake HowardSingle Family
Taxes:$4,614
Remarks: Welcome home to this charming 3-bedroom, 2-bath residence nestled on a spacious lot in the heart of Winter Haven. Offering nearly 1,300 square feet of comfortable living space, this well-maintained home features a functional layout with a kitchen and family room combination, ceiling fans throughout, and plenty of natural light. Step outside to your private backyard oasis complete with an in-ground pool—perfect for relaxing, entertaining, or enjoying Florida’s sunshine year-round. A one-car garage adds convenience, while the absence of HOA fees provides flexibility and freedom. Ideally located near schools, shopping, dining, and major roadways, this home is a wonderful opportunity for homeowners or investors alike. NEW ROOF 2020, NEW AC 2022. Don’t miss your chance to make this inviting Winter Haven property your own!
Listing Agent: Melissa Mottern (863-860-1808)
520 35TH ST NW, WINTER HAVEN, FL 33880
$199,900146 Days on yellowkey MLS ID: K4903131
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1008 Built: 1962 Tax: $650 (2024)Community: Deer Lake Terrace SubSingle Family
Taxes:$650
High School: None
Remarks: Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets & oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting, irrigation well, pole barn for RV parking 28x20’ and outside carport laundry room. This home offers updated plumbing and abundant parking. Pride of Ownership. A must see!
Listing is courtesy of: WATSON & WATSON INC REALTORS (863-294-4149)
Listing Agent: Wendy Gibbs (863-557-5249)
3661 QUEENS COVE BLVD, WINTER HAVEN, FL 33880
$259,9909 Days on yellowkey MLS ID: S5146164
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1632 Built: 2005Monthly Fee: $12 Tax: $3,706 (2025)Community: Queens CoveSingle Family
Taxes:$3,706
Remarks: Welcome to this well-maintained residence located in the established Queens Cove community of Winter Haven. This inviting home offers a comfortable and functional layout with approximately 1,500+ square feet of living space, featuring a spacious living area, a well-designed kitchen, and generously sized bedrooms that provide both comfort and flexibility for everyday living. As you enter, you’ll appreciate the natural flow of the home, creating a warm and welcoming environment that feels both practical and easy to enjoy. The layout allows for a seamless transition between living spaces, making it ideal for relaxing or hosting gatherings. Each area of the home has been designed to maximize usability and comfort. The property offers a great balance between space and simplicity, making it a solid option for buyers seeking a home that is both functional and full of potential. Whether you are looking for your next primary residence or simply a well-located property, this home presents a great opportunity. Situated within a well-established neighborhood, the home provides convenient access to main roads and is just a short drive to Lakeland, LEGOLAND Florida Resort, and within reach of the greater Orlando area, offering a great balance between quiet residential living and access to Central Florida attractions. This is a great opportunity to own a home in a steadily growing area. Schedule your private showing today.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Julio Portillo Castro (407-879-1772)
3339 QUEENS COVE LOOP, WINTER HAVEN, FL 33880
$254,90028 Days on yellowkey MLS ID: O6386232
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1158 Built: 1994Monthly Fee: $12 Tax: $3,511 (2025)Community: Queens Cove Ph 02Single Family
Taxes:$3,511
Remarks: This traditional 3-bedroom, 2-bathroom home is located in the established Queens Cove Ph 02 neighborhood. Designed with a functional and classic layout, this residence offers a comfortable living environment perfectly suited for a variety of lifestyles. The heart of the home features a traditional floor plan that provides a clear and smart separation of living spaces. The kitchen is beautifully updated with sleek quartz countertops and Stainless steel appliances, creating a modern and stylish space for meal preparation and entertaining. Situated in a prime location, this home is just minutes away from local essentials, including shopping, dining, and parks. Whether you are searching for a forever home or a smart investment opportunity, this property offers both convenience and potential. Schedule your private showing today!
Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)
Listing Agent: Robert Salmons (888-216-6364)
4656 MAGNOLIA PRESERVE LOOP, WINTER HAVEN, FL 33880
$334,9006 Days on yellowkey MLS ID: L4960603
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2038 Built: 2007Monthly Fee: $32 Tax: $4,387 (2025)Community: Magnolia PreserveSingle Family
Taxes:$4,387
Remarks: Completely renovated and move in-ready Large 4 bedroom, 2 bathroom house awaits your family! On a desirable corner lot, in a quiet neighborhood. New Roof, New Paint, New Flooring all through the house, New Stainless Steel Appliances, New Kitchen Faucet, Like a New Home!! Master Bath has a walk in closet and Garden Tub and Seperate Shower with a Seat. This home offeres a Separate Dining area and a Office or Playroom. Close to the new Polk Parkway extension, so travel to schools, shopping, restaurants and entertainment is super convenient. Great school district and priced to sell quickly. Call today for a showing!
Listing is courtesy of: AVERY PROPERTIES INC. (863-682-1902)
Listing Agent: Anne Greenhow (863-698-4562)
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