Location: Winter Haven
Do Not Show Listings
295 LAKE SMART CIR, WINTER HAVEN, FL 33881
$2,10010 Days on yellowkey MLS ID: L4962064
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2021Community: Lake Smart PointeSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: 295 Lake Smart Circle in Winter Haven offers comfortable Florida living with scenic water views in a peaceful lakeside setting. This well-maintained 3-bedroom, 2-bath home features a spacious open floor plan with plenty of natural light, creating a warm and inviting atmosphere throughout. The kitchen offers ample cabinet and counter space and opens to the main living and dining areas, making it ideal for both everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Enjoy relaxing lake views from the front of the property and take advantage of the home’s convenient location near shopping, dining, schools, parks, and major roadways. Combining comfort, convenience, and beautiful surroundings, this home is a great opportunity to enjoy the best of Central Florida living.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Marquita Smith (863-289-3343)
1539 ROSELAWN ST SW, WINTER HAVEN, FL 33880
$1,80010 Days on yellowkey MLS ID: S5149633
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1147 Built: 1957Community: Tranquility Park 02 RepSingle Family
Remarks: Beautifully fully remodeled 3-bedroom, 2-bathroom home located at 1539 Roselawn, offering modern comfort and stylish living throughout. This residence features premium waterproof luxury vinyl flooring, a spacious and upgraded kitchen with elegant granite countertops, and stainless steel appliances. The home has been thoughtfully updated to provide both functionality and design, along with a reliable AC system updated in 2018 for added comfort and efficiency. Located in a desirable area with no HOA restrictions, this property offers flexibility and convenience. Ideal for tenants seeking a move-in ready home with quality finishes and modern upgrades. A true rental opportunity combining comfort, style, and value.
Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Ines Morales (863-738-8794)
310 FARNOL ST SW #3, WINTER HAVEN, FL 33880
$900140 Days on yellowkey MLS ID: P4937509
REDUCED by $50 (5.3%) on 05/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 456 Built: 1965Community: Hoffmans & Lake View Add RepApartment
Elementary School: Lake Shipp Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Discover easy downtown living in this bright and inviting studio apartment located in the heart of Winter Haven. The spacious combined living and bedroom area offers plenty of room to relax and make the space your own. A large sliding glass door fills the apartment with natural light and opens to a large, quiet yard. This studio blends comfort, convenience, and simplicity, all within steps of the energy and amenities of downtown Winter Haven.
Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)
Listing Agent: Christin Davis (863-259-4600)
680 GROVE ST, WINTER HAVEN, FL 33881
$2,10010 Days on yellowkey MLS ID: S5150395
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2080 Built: 2023Community: Inman Grvs Ph 2Single Family
Remarks: Welcome to this beautiful newer construction home located in the desirable community of Inman Groves in Winter Haven. Built in 2023, this spacious 3-bedroom, 2-bath residence offers over 2,000 square feet of comfortable living space with a modern open-concept design perfect for everyday living and entertaining. The home features a bright and inviting layout with stylish finishes throughout, a spacious kitchen with modern appliances, built-in features, and a large living area filled with natural light. In addition to the bedrooms, the home also includes a versatile flex space perfect for a home office, playroom, formal dining area, gym, or additional sitting room. The primary suite offers plenty of space and privacy, while the additional bedrooms provide comfort and flexibility for family or guests. Enjoy the convenience of a 2-car garage, indoor laundry room with washer and dryer included, and a pet-friendly policy for small dogs and cats. Conveniently located near shopping, dining, schools, and major roadways with easy access throughout Central Florida. Available June 1st. Schedule your private showing today before it’s gone!
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Vicky Torres Rodriguez (863-258-9439)
245 WINTER RIDGE BLVD, WINTER HAVEN, FL 33881
$1,55011 Days on yellowkey MLS ID: S5150403
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1992Community: Winter Ridge CondoHalf Duplex
Elementary School: Fred G. Garnier Elem
Remarks: One or more photo(s) has been virtually staged. Nestled in the peaceful Winter Ridge community, this beautifully renovated 2-bedroom, 2-bath END-UNIT condo villa offers comfort, convenience, and low-maintenance Florida living. Recent upgrades include a NEW ROOF (2024), TILE FLOORING THROUGHOUT. Tucked away toward the back of the community, this home provides added privacy and a serene setting. Inside, you’ll find a bright and open floor plan with spacious living and dining areas filled with natural light. The kitchen features ample cabinetry, generous counter space, and a breakfast bar perfect for casual dining. The primary suite includes a walk-in closet and private en-suite bathroom, while the second bedroom is ideal for guests, a home office, or flex space. Enjoy relaxing mornings and evenings on the private enclosed rear lanai overlooking mature landscaping. Washer and dryer are included for added convenience. Residents of Winter Ridge enjoy access to a community pool, scenic walking paths, and a private dock on Lake Smart, perfect for fishing and boating enthusiasts. Conveniently located near shopping, dining, golf courses, and downtown Winter Haven. Don’t miss this opportunity to enjoy the Florida lifestyle in a quiet lakeside community!
Listing is courtesy of: R&J REALTY AND PROPERTY MANAGEMENT LLC (407-729-3280)
Listing Agent: Jose Marrero Cruz (407-729-3280)
1228 HAINES DR, WINTER HAVEN, FL 33881
$1,99534 Days on yellowkey MLS ID: S5148202
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1431 Built: 2019Single Family
Remarks: This house have an open, spacious floor plan with a standout kitchen featuring stainless steel appliances and large pantry, flowing into an inviting "Great Room". The home is equipped with solar panels to assist with energy efficiency. Proximity to medical facilities, shopping, restaurants, and grocery stores, with easy access to US 27 and I-4. The community is noted for having a low HOA fee and no CDD.
Listing Agent: Hector Figueroa (939-241-0047)
955 6TH ST SE #5, WINTER HAVEN, FL 33880
$1,19040 Days on yellowkey MLS ID: S5148308
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 550 Built: 1954Community: Hackles AddApartment
Remarks: The renovated first-floor apartment features laminate floors throughout, beautiful kitchen cabinets, appliances include a stove, microwave, and refrigerator and Washer & Dryer It also features an A/C unit Hight efficiency, modern lighting lamps and blinds. Security cameras on property exteriors. Great location offering walking distance to the bus line, Winter Haven High School, municipal offices, restaurants, shopping areas, Hospitals, and a short drive distance to Sunny Beaches.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Manuel Paredes (407-840-2272)
2000 15TH CT NW #23, WINTER HAVEN, FL 33881
$1,39542 Days on yellowkey MLS ID: S5148225
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 750 Built: 1973Community: Blount & Whitledge SubApartment
Remarks: Apartment For Rent - Move In Ready! MOVE IN SPECIALS: Free 1/2 Month Rent, waived Processing Fee and $250 Security Deposit based on approval. This second (2nd) floor unit comes with all stainless steel kitchen appliances, in unit washer/dryer, new tile backsplash, new countertops and tile flooring throughout. This unit is freshly painted and all fixtures have been replaced. Unit offers a view to the inground community pool. Laundry facilities located on site. Other amenities are currently being installed and will be available for tenant use such as Dog Park and picnic area. Property is located a short distance to your local Publix Super Market as well as to the Winter Haven Hospital, Short drive to Downtown Winter Haven and many more shopping centers and restaurants for your convenience.
2066 KATIE CT, WINTER HAVEN, FL 33884
$2,05548 Days on yellowkey MLS ID: P4938449
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1802 Built: 1983Community: Winterset North Ph 03Single Family
Remarks: 3/2 in Southeast Winter Haven near Legoland. Big porch, oversized garage. New Roof! Call owner Bob Jessee for showing info.
Listing is courtesy of: TOWN & COUNTRY REAL ESTATE (863-293-1141)
Listing Agent: Frank Vaughn (863-207-5746)
1734 CARNOSTIE RD, WINTER HAVEN, FL 33884
$2,05049 Days on yellowkey MLS ID: TB8497301
REDUCED by $50 (2.4%) on 05/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1418 Built: 2023Community: Villamar Ph 3Single Family
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: McLaughlin Academy Of Excellence
Remarks: Beautiful Comfortable home awaits your tenant and their family. This 3/2/2 has an open floor concept. The great room plan opens up to vaulted ceiling . The kitchen has is a comfy breakfast nook. The home also features a Gourmet Kitchen The beautiful master bedroom is a split plan. All bedrooms are comfortable sized. Carpet in all bedrooms and tiles in the wet area. This is a must see. Wont last long.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Hillorie Dias (813-417-9549)
2587 SAGE VALLEY WAY, WINTER HAVEN, FL 33884
$2,30012 Days on yellowkey MLS ID: O6409720
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1535 Built: 2024Community: Harmony/Lk Eloise Ph 2Spa: NoSingle Family
Remarks: Welcome to your dream home! This beautiful property offers 3 spacious bedrooms, 2 modern bathrooms, and is move-in ready with top-of-the-line finishes. Located in the desirable Winter Haven area, this home features appliances and smart home technology, offering you the convenience of a fully integrated, intelligent home system. Key Features: 3 Bedrooms – Generously sized for comfort. 2 Modern Bathrooms – Tastefully designed with contemporary finishes. Appliances included – energy-efficient models. Smart Home Technology. Don't miss the opportunity to rent this exceptional home! Perfect for those who appreciate modern living with smart features. Contact us today for a private viewing.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Mardonia Gina (863-513-3056)
2371 BRASSIE CT, WINTER HAVEN, FL 33884
$2,25082 Days on yellowkey MLS ID: O6389720
REDUCED by $250 (10.0%) on 05/20/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2522 Built: 2022Community: Villamar Ph 3Single Family
Remarks: This stunning 5-bedroom, 3-bathroom home offers the perfect blend of modern comfort, energy efficiency, and scenic beauty. Located in the desirable VillaMar community, this spacious home features an open-concept layout ideal for family living and entertaining. Enjoy peaceful mornings with breathtaking pond views right in your backyard — your private retreat for relaxation and tranquility. The home also includes solar panels, helping you save on energy bills while living sustainably. With elegant finishes, a large kitchen, and plenty of natural light throughout, this home is move-in ready and waiting for its new owners. Features resort-style community amenities including a zero-entry swimming pool with a lap lane, a playground, a dog park and sidewalks.Conveniently located near shopping, restaurants, and top-rated schools — this is the lifestyle you’ve been looking for in Winter Haven!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Karina Turcios (407-346-7606)
1662 TEAGAN LN, WINTER HAVEN, FL 33884
$2,40012 Days on yellowkey MLS ID: O6409324
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1432 Built: 2024Community: Peace Crk ReserveSingle Family
Remarks: Beautiful 3-bedroom, 2-bath home located in the desirable community of Winter Haven. This property features a spacious and bright floor plan with an open living and dining area, perfect for entertaining. The kitchen offers ample cabinet space and modern appliances. The primary suite includes a private bathroom and generous closet space. Enjoy a large backyard ideal for relaxing or outdoor gatherings. Conveniently located near shopping, restaurants, schools, and major highways. A wonderful opportunity to own or rent a charming home in a great location!
Listing is courtesy of: OPTIMAR INTERNATIONAL REALTY (305-944-0477)
Listing Agent: Cristina Lopez (786-346-3157)
5667 STRUTHERS CT, WINTER HAVEN, FL 33884
$1,35018 Days on yellowkey MLS ID: P4938716
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 775 Built: 1983Community: Lake Fox ShoresHalf Duplex
Elementary School: Garden Grove Elem
Remarks: Clean and cozy 2-bedroom, 1-bathroom duplex in southeast Winter Haven. Featuring wood laminate flooring in living areas and bedrooms, with ceramic tile flooring in the kitchen and bathroom. Kitchen equipped with newerKitchen cabinets and comes with range/oven, refrigerator, and washer/dryer hookups in utility closet. Both bedrooms of ample size with ceiling fans. Recently remodeled bathroom with tile tub/shower. Conveniently located near shopping, Walmart, Publix, Legoland, and quick access to HWY 27 for Orlando/Tampa.
Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)
Listing Agent: Carlee Marchetti (863-258-3338)
3904 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$1,950125 Days on yellowkey MLS ID: P4937653
REDUCED by $200 (9.3%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1709 Built: 2023Community: Osprey PointeSpa: NoSingle Family
Remarks: Modern design with comfort in mind! MOVE IN READY! SUMMER MOVE IN SPECIAL: $1,950.00/month! Spacious 3-Bedroom, 2-Bath Home in a Charming Winter Haven Neighborhood Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,700 square feet of living space in a quaint and friendly community. Conveniently located near downtown Winter Haven, with easy access to theme parks, shopping, and dining, this home perfectly blends comfort and convenience. Enjoy peace of mind with a 2-car garage for secure parking, and relax on the rear patio while taking in the beautiful Florida weather. The community features a private boat dock, swimming pool, and clubhouse available for resident events and gatherings. Inside, you’ll find an inviting open floor plan with elegant finishes throughout, including granite countertops, luxury vinyl plank flooring in the main living areas, and plush carpet in the bedrooms. The primary suite offers a spacious walk-in closet, tray ceiling, and a private en suite bath. Additional features include a mudroom/laundry room, vaulted ceilings in the living room, and a dining nook with space for counter seating at the kitchen bar. The kitchen comes fully equipped with stainless steel appliances, including a refrigerator with water and ice dispenser, electric oven with glass cooktop, dishwasher, and built-in microwave. A full-size washer and dryer are also included in the laundry room. This home combines modern comfort with community charm — a true must-see! AMENITIES INCLUDED: Lawn Mowing provided by HOA (Tenant responsible for irrigation and keeping lawn and plants "green") Community Pool & Clubhouse Full size washer and dryer Central AC/Heat PRICING: RENT: $2150.00/month + utilities SUMMER MOVE IN SPECIAL: $1,950.00/month! SECURITY DEPOSIT: Starts at $21,950.00 AREA: 1700 SF LEASE TERMS: 1 Year ADDRESS: 3904 Osprey Pointe Cir, Winter Haven, FL 33884
Listing is courtesy of: CARREROU ENTERPRISES, LLC (863-294-2384)
Listing Agent: Ozzie Carrerou (863-294-2384)
219 CLOVERDALE RD, WINTER HAVEN, FL 33884
$2,30013 Days on yellowkey MLS ID: L4962004
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1858 Built: 2007Community: Savanna PointeSingle Family
Remarks: ~Fully Furnished 4/2 Winter Haven Residence Offered for Lease - Just bring your wardrobe and toothbrush!~ This resort-style home boasts a fully furnished Florida-themed beautiful interior, ceramic tiling throughout, spacious kitchen with breakfast bar and plenty of cabinetry/counter space, sizeable primary bedroom with large walk-in closet and en-suite bath featuring dual vanities and a garden jacuzzi tub. Additional features include sliding door access to a serene, screened in Mediterranean-style patio, inside utility with washer/dryer, and a two car garage. Well positioned, this property is convenient to LegoLand, dining, shopping, educational and medical facilities.
Listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM (863-940-3756)
Listing Agent: Andrea Muzzy (863-430-1733)
332 AVENUE D SE, WINTER HAVEN, FL 33880
$2,00013 Days on yellowkey MLS ID: S5150205
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1090 Built: 1977Community: Twin Oaks AddApartment
Remarks: This 2 bedroom 2 bathroom end unit is fully furnished with a modern flair. Renovated with new roof, energy efficient tankless water heater, paint, appliances & more. Featuring luxury vinyl floors throughout, granite countertops in the kitchen, both bathrooms feature renovated showers & tub, vanities & fixtures. This home is turnkey including all linens, electronics and kitchenware. The living room is spacious while offering a 75" smart TV and sectional couch. Master bedroom features a king size bed, large walk-in closet, 55" smart TV, en suite bathroom with shower/tub combo. The guest bedroom offers a queen size bed and 43" smart TV. The guest bathroom has a walk-in shower. This unit is equipped with a washer & dryer in the laundry closet. There is a private parking area onsite. Located close to hospitals, schools, shopping, restaurants and more.
Listing is courtesy of: THE PROPERTY FIRM (407-530-5444)
Listing Agent: Kathryn Shevlin (407-414-7009)
1103 CYPRESS GARDENS BLVD #17, WINTER HAVEN, FL 33884
$1,20013 Days on yellowkey MLS ID: L4961998
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 575 Built: 1980Community: Lamplighter VillageSpa: NoCondo
Remarks: One or more photo(s) has been virtually staged. Chain of Lakes WATERFRONT living with stunning views of Lake Roy! This beautifully updated 1-bedroom condo offers the perfect blend of peaceful lakeside charm and everyday convenience, located just minutes from shopping, dining, and entertainment. Step inside to find wood-look tile flooring throughout, fresh calming oasis-blue paint, and abundant natural light pouring in through updated windows showcasing picturesque lake views. The spacious living area flows into a versatile window-lined nook, ideal for a home office, reading corner, or expanded seating area. The updated kitchen features modern appliances and an efficient layout designed to maximize space and functionality. The bedroom offers two closets for ample storage along with a convenient stackable washer and dryer nook. The bathroom has been tastefully renovated with a modern subway-tiled tub surround. Just outside your front door, enjoy a large HOA-maintained green space with picnic seating overlooking the water. Beyond that, you’ll have direct access to Lake Roy, perfect for kayaking, paddle boarding, or simply soaking in the serene setting. The community dock provides additional space for fishing, relaxing, and enjoying breathtaking lakefront sunsets. Don’t miss this rare opportunity to lease a charming lakeside retreat on the Chain of Lakes!
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Jake Bellamy (863-838-7804)
612 HEATHER GLEN LOOP, WINTER HAVEN, FL 33884
$2,00013 Days on yellowkey MLS ID: P4938759
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1709 Built: 2002Community: Heather Glen Ph 02Spa: NoSingle Family
Remarks: This is the ONLY rental in Winter Haven that has a pool!! This cute 3 bedroom 2 bath home 2 garage screened pool home has a fully PVC fenced in back yard, perfect for kids to play or aminals to run free. Located in a quiet neighborhood. Clean freshly painted interior and ready for a tenant!
Listing is courtesy of: SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC (863-289-3586)
Listing Agent: Amy Riggleman (863-287-0754)
3912 GIORGIO DR, WINTER HAVEN, FL 33884
$1,90013 Days on yellowkey MLS ID: TB8510050
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1483 Built: 2026Community: Villamar Phase 6 And Phase 6DSingle Family
Elementary School: Pinewood Elem
Remarks: Brand new, energy-efficient home available NOW for rent! Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet. This is a split floor plan allowing everyone their privacy. The square footage is the perfect size so you don't feel crowded, but you won't spend an eternity trying to keep it clean. Enjoy the easy clean up in your spacious kitchen with the easy to clean granite countertops. Residents have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park.
Listing is courtesy of: KEY PREMIER REALTY (813-943-3501)
Listing Agent: Rick Scott (813-751-7030)
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