Location: Winter Haven , 33884
Do Not Show Listings
3912 GIORGIO DR, WINTER HAVEN, FL 33884
$1,90021 Days on yellowkey MLS ID: TB8510050
0 Days Off yellowkey (back on 6/9/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1483 Built: 2026Community: Villamar Phase 6 And Phase 6DSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Pinewood Elem
High School: Lake Region High
Tax Year:
Middle School: Denison Middle
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)
1498 AUSTIN ST, WINTER HAVEN, FL 33884
$2,00076 Days on yellowkey MLS ID: P4938243
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1935 Built: 2023Community: Peace Crk ReserveSingle Family
Elementary School: South Pointe Elementary
Middle School: Westwood Middle
Remarks: One or more photo(s) has been virtually staged. Step into this inviting 4 bedroom, 2 bathroom home in the Peace Creek Reserve community, where comfort meets modern style. The split floor plan gives everyone their own space, while the open living, dining, and kitchen area keeps the heart of the home bright, connected, and perfect for everyday life. You’ll love the modern appliances, clean finishes, and ceiling fans in every bedroom for year-round comfort. A dedicated laundry room with hookups makes chores easier, and the 2-car garage offers plenty of room for parking and storage. Peace Creek Reserve also features a refreshing community pool — the perfect spot to unwind, cool off, or enjoy a quiet weekend afternoon. Ready to see it in person? Contact us today to schedule your tour and explore everything this home has to offer!
Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)
Listing Agent: Christin Davis (863-259-4600)
5202 WATERVIEW WAY #5202, WINTER HAVEN, FL 33884
$1,750102 Days on yellowkey MLS ID: P4937984
REDUCED by $50 (2.8%) on 05/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 930 Built: 1992Community: Garden Villas 02 Ph 01Condo
Elementary School: Chain O Lakes Elem
Remarks: A comfortable first-floor 2 bed, 2 bath condo in the gated Winterset community, this home offers an easy, open layout with plenty of natural light and convenient ground-level access. Each bedroom has its own full bathroom, giving you a setup that works well for roommates, guests, or anyone who wants a little extra privacy. The condo can be leased furnished for a turnkey move-in or unfurnished if you prefer to bring your own style. Winterset adds to the appeal with lakefront views, a community pool, tennis courts, and beautifully maintained grounds that make everyday living feel calm and inviting. Don't miss your opportunity to live in this luxurious community! Schedule a tour today! ($1,750 with furniture, $1,650 without)
116 HOLMES PL, WINTER HAVEN, FL 33884
$2,80056 Days on yellowkey MLS ID: P4938445
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1875 Built: 1967Community: Fla Highlands Co SubSpa: NoSingle Family
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Remarks: One or more photo(s) has been virtually staged. Experience refined Florida living in this elegant 4 bedroom, 3 bathroom residence, where thoughtful design and upscale comfort come together seamlessly. The home welcomes you with spacious living areas, a well-appointed kitchen, and a layout that offers both openness and privacy. The primary suite provides a serene retreat, while the additional bedrooms and baths offer flexibility for guests, family, or a dedicated workspace. A 2-car garage adds convenience and secure storage. Step outside to your private backyard sanctuary, fully fenced for peace of mind and designed for effortless outdoor enjoyment. The highlight of the home is the stunning in-ground pool, enclosed within an expansive, fully screened structure that creates a resort-style environment perfect for lounging, entertaining, and year-round relaxation. With pool maintenance included in the rent, you can indulge in the luxury without lifting a finger. This home blends sophistication, comfort, and an elevated outdoor lifestyle into one exceptional living experience. Schedule your tour today!
1103 CYPRESS GARDENS BLVD #17, WINTER HAVEN, FL 33884
$1,20021 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)
3408 COSTELLO CIR, WINTER HAVEN, FL 33884
$1,8004 Days on yellowkey MLS ID: O6414344
REDUCED by $100 (5.3%) on 06/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1713 Built: 2025Community: Villamar Ph 6 & Ph 6DSpa: NoSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: RECENTLY REDUCED !! 4-bedroom 2-bathrooms home for RENT ! A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting quartz countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. Located seven minutes from Legoland, five minutes from Publix, and third-teen minutes away from Lake Wales Shopping Mall. Water softener and Landscaping is included with the rent. Let’s schedule a showing today !
Listing is courtesy of: BEACH REALTORS (407-201-6300)
Listing Agent: Rachel Reyes (407-201-6300)
6518 CRESCENT LOOP, WINTER HAVEN, FL 33884
$2,25056 Days on yellowkey MLS ID: O6399226
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1894 Built: 2016Community: Crescent ViewSingle Family
Remarks: This is a very spacious, beautiful, freshly painted and professionally cleaned 3-bedroom/2-bath/ 2-car garage single family home in the quiet and well-kept Crescent View Community. Property features an open floor plan, beautiful ceramic and laminate flooring, a very spacious kitchen with lots of cabinet space, granite countertops and stainless steel appliances. The primary bedroom is very spacious and features a large walk-in closet. The secondary bedrooms are very spacious with large closets. The backyard is fenced so you have lots of privacy. The patio and backyard are perfect for entertaining family and friends. Close to shopping, dining, schools, and major roadways. Also listed for sale, whichever comes first. This one is just waiting for you to come home to!
Listing is courtesy of: EATON REALTY SERVICES (800-630-1990)
Listing Agent: Arlene Cowan (800-630-1990)
1103 CYPRESS GARDENS BLVD #30, WINTER HAVEN, FL 33884
$1,10043 Days on yellowkey MLS ID: P4938564
REDUCED by $100 (8.3%) on 05/28/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 475 Built: 1980Community: Lamplighter VillageCondo
Elementary School: Elbert Elem
Remarks: This charming first-floor 1 bed, 1 bath condo sits just off Cypress Gardens Blvd, tucked in a spot where the lake becomes part of your everyday view. As you pull into the parking lot, the water is the first thing you see — calm, open, and only a short walk from your front door. The unit itself offers easy living with a simple, comfortable layout and an in-unit washer and dryer for added convenience. Being on the ground floor means quick access in and out, and the lakeside path just steps away gives you a peaceful place to unwind, sip your morning coffee, or enjoy the quiet at the end of the day. Reach out to schedule a tour and see the tranquility for yourself.
1050 MICHELANGELO LN, WINTER HAVEN, FL 33884
$2,1008 Days on yellowkey MLS ID: P4938891
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1659 Built: 2022Community: Estates/Lk FlorenceSingle Family
Remarks: Check out this LIKE NEW 2022-built home located in the desirable Estates of Lake Florence community in Winter Haven, just off Overlook Drive. This beautifully maintained 3-bedroom, 2-bathroom split floorplan home offers the perfect blend of style, space, and convenience. Inside, you'll find ceramic tile flooring throughout the main living areas and plush carpet in the bedrooms for added comfort. The sleek, modern kitchen features gray cabinetry, quartz countertops, a spacious integrated island, and a walk-in pantry—perfect for both everyday living and entertaining. The owner’s suite is tucked away at the back of the home, just off the kitchen and living room, and boasts a large walk-in closet and a beautifully appointed en suite bathroom. Custom noise-resistant windows in the master bedroom ensure peaceful rest and privacy. Smart home features elevate the living experience, including smart light switches compatible with Alexa and Google, a smart garage door opener with an exterior keypad for easy access, and a keyless smart lock on the front door. Ceiling fans are installed throughout the home for added comfort and energy efficiency. Situated on a massive .32-acre wedge lot, this property offers one of the largest yards in the community—a rare find in an HOA neighborhood. Landscaping service is included, making maintenance a breeze. Don’t miss your chance to live in a like-new home with premium finishes, cutting-edge smart features, and an expansive outdoor space. Available now—schedule your tour today!
2122 CHRIS DR, WINTER HAVEN, FL 33884
$2,030124 Days on yellowkey MLS ID: O6380142
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1824 Built: 2025Community: Peace Creek Reserve 50'SSingle Family
Elementary School: Wahneta Elem
Remarks: Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and everyday enjoyment. The kitchen is fully equipped with appliances, wood cabinets, and a breakfast bar for quick meals. The primary suite includes generous closet space, offering comfort and convenience. The home is located in a planned community with newly built single-family homes and offers excellent amenities such as a community pool, playground, sidewalks, and a beautiful natural creek, providing a peaceful and family-friendly environment. Excellent location, close to: Schools and supermarkets Restaurants and local shopping Quick access to US-27 and main roads Just minutes from LEGOLAND® Florida Resort Easy access to downtown Winter Haven and nearby cities Don’t miss this opportunity to rent a brand-new home with comfort, amenities, and a prime location. Schedule your showing today!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jessyka Dos Santos (407-364-0170)
521 REGGIE RD, WINTER HAVEN, FL 33884
$2,45077 Days on yellowkey MLS ID: L4960535
REDUCED by $150 (5.8%) on 06/09/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2024Community: Peace Crk ReserveSingle Family
Middle School: McLaughlin Academy Of Excellence
Remarks: Rent a home and have an extra area for your friends or family to live while visiting . This near new !! 4 bedroom 3 bathroom Lennar Next Gen home available for lease in Peace Creek Reserve in Winter Haven. This layout features a private mother in law suite with its own entrance, living area, kitchenette, bedroom, and full bath, ideal for multigenerational living or added privacy. Main home offers an open concept floor plan with a large living area, modern kitchen with island, and separate dining space. Primary suite includes a walk in closet and private bath with dual sinks and walk in shower. Secondary bedrooms are well sized with a shared full bath. Interior features includes tile in main living areas, carpet in bedrooms, and tile in all wet areas. Laundry room included. Attached 2 car garage. Move in ready. Schedule your showing today.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
5657 STRUTHERS CT, WINTER HAVEN, FL 33884
$1,475Listed 06/08/2026 11:01PM MLS ID: O6415136
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 780 Built: 1984Community: Lake Fox ShoresHalf Duplex
Remarks: Beautiful 2 bedroom, 1 bathroom duplex located in a quiet and desirable area off Cypress Gardens Boulevard. This move-in ready home features a brand-new roof, renovated interior, block construction, and a spacious oversized lot with 2 parking spaces. The property includes a bright and comfortable living area, new stove, washer and dryer, and a large deep freezer for additional food storage. Enjoy the relaxing screened-in lanai/balcony, perfect for outdoor seating and extra living space. Conveniently located just minutes from shopping centers, restaurants, schools, and major highways while still offering the privacy and comfort of a peaceful community. Property Features: • 2 Bedrooms • 1 Bathroom • Newly Renovated • Brand New Roof • Screened-In Lanai / Porch • Washer & Dryer Included • New Stove Included • Large Deep Freezer Included • 2 Parking Spaces • Oversized Lot • Quiet Community • Excellent Location
Listing is courtesy of: D & D PROPERTY MANAGEMENT SOLUTIONS LLC (407-434-1693)
Listing Agent: Teresa Dishington (407-346-5001)
3927 PALAZZO PL, WINTER HAVEN, FL 33884
$1,90026 Days on yellowkey MLS ID: O6408068
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1597 Built: 2023Community: Villamar Ph 4Single Family
Remarks: MOVE-IN READY and available now! Rare opportunity to lease the FINAL Amarylis model in the community—a beautifully maintained 2023-built home offering modern comfort, style, and convenience. Featuring 3 bedrooms, 2 bathrooms, soaring ceilings, a bright open-concept layout, luxury vinyl flooring throughout the main living areas, and an inviting walk-in foyer. The spacious primary suite includes a walk-in closet and en-suite bath with dedicated vanity seating. Enjoy added perks including a full security camera system for tenant use, playground set, charming front porch, and private backyard space perfect for relaxing or entertaining. Residents also enjoy access to resort-style community amenities including a pool, cabana seating, and recreational areas. Conveniently located near shopping, dining, and everyday essentials. Skip the wait—this home is ready for immediate occupancy! THIS HOME IS ALSO AVAILABLE FOR PURCHASE UNDER MLS #O6383833.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Iliana Perez (407-990-7293)
1042 MICHELANGELO LN, WINTER HAVEN, FL 33884
$2,47533 Days on yellowkey MLS ID: S5149443
REDUCED by $125 (4.8%) on 06/08/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2386 Built: 2022Community: Estates/Lk FlorenceSingle Family
Remarks: Like New Home in Haines City offers, two-story layout with four bedrooms and 2.5 bathrooms. The open, spacious floor plan includes a loft and a bonus room that can adapt to your needs, while the kitchen features granite countertops, a central island, and stainless steel appliances open to family room. All bedrooms are on 2nd floor for added privacy. A large fenced-in yard provides outdoor privacy and usable space. Well-suited for modern living, this recently built home combines practical design and contemporary finishes in Winter Haven, FL.
Listing is courtesy of: ACKLEY FLORIDA PROPERTY MANAGEMENT INC (407-846-8846)
Listing Agent: Kristen Chowdhury (407-721-3829)
36 ENCLAVE DR, WINTER HAVEN, FL 33884
$1,990153 Days on yellowkey MLS ID: P4937445
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1532 Built: 1997Community: Cypresswood Enclave Ph 2Townhouse
Remarks: One or more photo(s) has been virtually staged. Corner - unfurnished unit @ The Enclave, located within the manned, gated Cypresswood Golf & Country Club in Winter Haven, Florida. This premier community features an 18-hole championship golf course designed by award-winning architect Ron Garl. The course is open 365 days a year, from sunrise to sunset. Residents enjoy access to outstanding amenities including a pro shop, wellness center, lounge, dining rooms, swimming pool, and tennis courts. Practice facilities include a driving range, putting green, and chipping green. The clubhouse is ideal for events and celebrations, accommodating up to 175 guests. The Enclave at Cypresswood Golf Course is conveniently located just off Dundee Road, near Dollar General, and only minutes from Win-Dixie on Highway 27. It’s a short drive to downtown Winter Haven and LEGOLAND®. Shopping and entertainment options abound: • Dollar General is just across the guardhouse. Winn-dixie just 1/4 mile from the guardhouse. • Approximately 5 miles to Eagle Ridge Mall, featuring Dillard’s, Regal Cinemas, a bowling alley, arcade, and food court. • About 15 miles to Posner Commons (Posner Park) in Davenport near I-4, offering major retailers such as Target, Best Buy, BJ’s Wholesale, popular restaurants like Chipotle and Five Guys, and Cinépolis IMAX, with ongoing mixed-use development. Property Features • Exterior and lawn maintenance included • Unfurnished corner unit • Open floor plan • Backs up to vacant land for added privacy • All appliances included Navigate a 3D Interactive Virtual Tour, 360 degree interactive aerial virtual tour with zoom in & out capabilities showcasing the property backing up to vacant land and view as far as the eyes can see. Walk through videos also available.
Listing is courtesy of: 3D TEAM REALTY LLC (863-604-3662)
Listing Agent: Jimmy Aguilar (863-604-3662)
3110 GOWAN DR #B1, WINTER HAVEN, FL 33884
$1,725363 Days on yellowkey MLS ID: O6317387
REDUCED by $1 (0.1%) on 06/06/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1180 Built: 2024Apartment
Remarks: Currently offering 1 months free upfront and a 99.00 app/ admin fee which is credited to rental account. Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. Discover Prose Cypress Pointe and make every day feel like a getaway. Nestled in the heart of Winter Haven and just a short drive from Lakeland, our pet-friendly luxury apartment community offers spacious floor plans, upscale finishes, and resort-style amenities—all thoughtfully crafted with you in mind. Here, you’ll find more than a home, you’ll discover a curated lifestyle. Lounge by the resort style pool and entertainment cabana, stay energized in the 24-hour fitness center, join invigorating on-site fitness classes, or grab complimentary breakfast on your way to work. It’s boutique living designed to elevate your everyday. With convenient access to Tampa, Orlando, and beyond, Prose Cypress Pointe let’s you live chic, live central and completely you.
Listing is courtesy of: THE APARTMENT BROTHERS LLC (704-502-7778)
Listing Agent: Aj Rebhan (704-502-7778)
3110 GOWAN DR #A1, WINTER HAVEN, FL 33884
$1,426363 Days on yellowkey MLS ID: O6317379
INCREASED by $1 (0.1%) on 06/06/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 835 Built: 2024Apartment
1015 LAKE FOREST BLVD #A2, WINTER HAVEN, FL 33884
$1,50532 Days on yellowkey MLS ID: O6406160
REDUCED by $25 (1.6%) on 06/06/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 2024Apartment
Remarks: Currently offering 3 months free on a 19-24 months lease and 2 months on a 13-18 month lease! Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. Experience stylish, comfortable living at The Waverly at Winter Haven. Located in the sought-after Cypress Gardens area, our pet-friendly community offers a peaceful lifestyle with convenient access to everything Central Florida has to offer. At The Waverly at Winter Haven, you'll enjoy a host of resort-inspired amenities designed to enhance your lifestyle, from a sparkling pool and sundeck to a cyber lounge and car wash station. Our spacious one, two, and three-bedroom floor plans offer modern features like stainless steel appliances, in-home laundry, and walk-in closets, ensuring comfort and convenience. With easy access to local attractions and major employers, living here is both practical and enjoyable. Schedule a tour today and discover why The Waverly is the perfect place to call home.
1015 LAKE FOREST BLVD #B3, WINTER HAVEN, FL 33884
$1,80032 Days on yellowkey MLS ID: O6406163
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 987 Built: 2024Apartment
Remarks: Currently offering 3 months free on a 19-24 months lease and 2 months on a 13-18 month lease! Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. Experience stylish, comfortable living at The Waverly at Winter Haven. Located in the sought-after Cypress Gardens area, our pet-friendly community offers a peaceful lifestyle with convenient access to everything Central Florida has to offer. At The Waverly at Winter Haven, you'll enjoy a host of resort-inspired amenities designed to enhance your lifestyle, from a sparkling pool and sundeck to a cyber lounge and car wash station. Our spacious one, two, and three bedroom floor plans offer modern features like stainless steel appliances, in-home laundry, and walk-in closets, ensuring comfort and convenience. With easy access to local attractions and major employers, living here is both practical and enjoyable. Schedule a tour today and discover why The Waverly is the perfect place to call home.
1015 LAKE FOREST BLVD #C1, WINTER HAVEN, FL 33884
$2,17532 Days on yellowkey MLS ID: O6406167
INCREASED by $50 (2.4%) on 06/06/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1229 Built: 2024Apartment
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