Location: Winter Haven
Do Not Show Listings
2085 ISLE ROYALE CT SE #189, WINTER HAVEN, FL 33880
$1,20013 Days on yellowkey MLS ID: L4960815
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 648 Built: 2004Community: Park LakeCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: John Snively Elem
High School: Winter Haven Senior
Tax Year:
Middle School: Denison Middle
Remarks: FOR RENT - 1 Bedroom/1 Bathroom Executive Condo in beautiful Park Lake. This ground floor unit has access to Lake Lulu, a community pool, a dock, and a clubhouse/recreational facility. The association fees are included in the rent. If you like skiing, Winter Haven is the Ski Capital of World! Downtown Winter Haven has about a dozen restaurants plus activities for the family every month. These activities include arts and crafts/farmer's markets, music, games, and more. The Winter Haven Public Library offers not only books but movies, family activities and a "kiddie corner". Winter Haven has 26 buildings registered with the US National Register of Historic Places. DISNEYWORLD and the Orlando attractions are only 45 minutes away. You just can't beat it...an active community, with parks, lakes, theatres, and restaurants. Just come to Winter Haven...it's the home of LEGOLAND!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Linda Andre (863-852-5747)
1174 HAINES DR, WINTER HAVEN, FL 33881
$2,10014 Days on yellowkey MLS ID: S5145960
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1682 Built: 2018Community: Lakes At Lucerne Park Ph 02Single Family
Elementary School: None
High School: None
Middle School: None
Remarks: Beautiful 4 bed / 2 bath home with modern upgrades throughout! This energy-efficient property features solar panels included at no extra cost—helping you save on electricity from day one. Enjoy tile flooring throughout the entire home, a remodeled kitchen and bathrooms, fresh interior paint, and brand-new appliances. Washer and dryer are also included for your convenience. The home offers a double garage and sits on a premium lot with gated access to both the backyard and side yard—ideal for extra space and privacy. The backyard is fully fenced, perfect for outdoor enjoyment. Additional features include a water softener, security cameras, and a covered patio. Pest control is also included at no extra cost—adding even more value. Prime location! Just 3.6 miles from US-27, 8.2 miles Dundee Rd, 14 miles from i-4, making commuting to Lakeland or Orlando easy. Conveniently close to shopping, dining, and entertainment, including Publix, Walmart, Manny’s Chophouse, Port 27, LEGOLAND® , Lake Eva Park, and Posner Park. No smoking permitted. All occupants 18+ must complete application and screening. Rent: $2,100/month. Security deposit: $2,100. Last month’s rent due at signing (waiver may be considered for exceptionally qualified applicants with strong credit and verified landlord references)
Listing is courtesy of: ONE TEAM REALTY (407-530-5006)
Listing Agent: Maria Cruz Vazquez (863-602-6968)
4004 CYPRESS LNDG S, WINTER HAVEN, FL 33884
$1,70013 Days on yellowkey MLS ID: P4938327
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1572 Built: 1986Community: Cypress Landing Ph 02Single Family
Elementary School: Garden Grove Elem
Remarks: Discover this beautiful 2-bedroom, 2-bath home with an additional flex room, perfect for a home office, den, or guest space, enclosed with a stylish barn door. Located in the desirable lakefront community of Cypress Landing, this home offers a welcoming and open layout with vaulted ceilings and abundant natural light. The kitchen is designed for both function and style, featuring ample cabinetry, generous counter space, and a breakfast bar that flows seamlessly into the dining area. A sliding glass door leads to a cozy 7x15 screened lanai—ideal for relaxing with your morning coffee. The primary suite is a private retreat, complete with an en-suite bathroom including a walk-in shower and 5x5 walk-in closet. The primary bedroom also has elegant French doors giving access to the flex room. Additional highlights include an inside utility room, updated laminate flooring throughout most of the home, and a fenced backyard for added privacy. Residents of Cypress Landing enjoy fantastic community amenities, including a clubhouse with social events, a heated pool, tennis courts, and a private boat ramp with lake access for fishing, boating, and watersports on Lake Dexter. Conveniently located just minutes from Legoland, shopping, and dining, this move-in-ready home offers the perfect balance of comfort and convenience.
Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)
Listing Agent: Carlee Marchetti (863-258-3338)
2893 WHISPERING TRAILS DR, WINTER HAVEN, FL 33884
$1,90022 Days on yellowkey MLS ID: S5146531
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1268 Built: 2017Community: Whispering Trails Ph 02Single Family
Elementary School: Elbert Elem
Remarks: This cozy and well-maintained home offers a warm and inviting layout, ideal for comfortable and easy living. The property features a functional floor plan with a modern kitchen, bright and spacious bedrooms, and low-maintenance living areas designed for convenience. Centrally located with quick access to US-27, US-17, SR-540, and I-4, this home provides easy commutes to Orlando and Tampa, as well as proximity to major attractions such as Disney and Legoland. Enjoy being just minutes away from lakes, parks, shopping centers, and a variety of dining options. A perfect rental opportunity for those seeking comfort, convenience, and a well-connected location in the growing Winter Haven area.
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Jenny Caso (407-694-9682)
2214 Ave B SW SW 2214 AVE B SW, WINTER HAVEN, FL 33880
$1,77514 Days on yellowkey MLS ID: S5146974
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1336 Built: 1957Community: Lathers Grove Sub Pb 37 Pg 17Single Family
Elementary School: Wahneta Elem
Remarks: Available for immediate move-in! Experience the perfect blend of historic charm and modern updates in this beautifully remodeled 1957 home, ideally located in the heart of Winter Haven. Just off First Street and minutes from shopping, public transportation, and major roadways, this home offers both convenience and character. Inside, you'll find a contemporary interior with brand-new flooring and crisp paint that highlights the home's timeless features. With three generously sized bedrooms, a giant Florida room, and easy access to everything Winter Haven has to offer, this home is as practical as it is charming.
Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)
Listing Agent: Sylvain Sara (727-623-5327)
1116 TYLER LOOP, WINTER HAVEN, FL 33884
$2,20014 Days on yellowkey MLS ID: O6395894
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2174 Built: 2026Community: Peace Crk ReserveSingle Family
Remarks: Discover modern comfort and thoughtful design in this newly built home at 1116 Tyler Loop in Winter Haven, FL, crafted by Lennar Homes. This residence showcases high-quality construction paired with stylish finishes, including an open-concept layout perfect for both everyday living and entertaining. The home features energy-efficient systems, smart home technology, and a contemporary kitchen equipped with sleek cabinetry, stainless steel appliances, and ample counter space. Spacious bedrooms and well-appointed bathrooms provide a relaxing retreat, while the private outdoor space offers room to unwind or host gatherings. Residents also enjoy access to desirable community amenities, which include a resort-style pool, clubhouse, playground, and beautifully maintained common areas that enhance the neighborhood’s appeal. With Lennar’s signature attention to detail and included upgrades, this home delivers exceptional value, convenience, and a move-in-ready experience.
Listing is courtesy of: JOHN SILVA REALTY & ASSOCIATES (407-420-7908)
Listing Agent: Julien Silva (352-348-9219)
616 CRYSTALS BLVD, WINTER HAVEN, FL 33884
$1,90014 Days on yellowkey MLS ID: O6395877
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1575 Built: 1993Community: Crystals LandingSingle Family
Remarks: Spacious and beautifully laid out home now available for rent! This open floor plan features 2 bedrooms, 2 bathrooms, plus a versatile flex space that can easily function as a third bedroom, office, or additional living area. Inside, you’ll find laminate flooring throughout with tile in the bathrooms, along with fresh interior paint and updated finishes that enhance the home’s overall appeal. The kitchen is designed for both functionality and style, offering a counter-height breakfast bar, movable island, oak cabinetry, two pantries, and ample counter space. The generously sized bedrooms provide comfort and flexibility, while additional features include upgraded ceiling fans, pull-down attic access, a lawn irrigation system, and a fully fenced backyard for added privacy. Conveniently located near Legoland, shopping, dining, and major roadways, this home offers both comfort and accessibility. Don’t miss this opportunity. Schedule your showing today!
Listing is courtesy of: FHG REALTY, LLC (407-505-7600)
Listing Agent: Jeff Inman (407-505-7600)
361 WINTER RIDGE BLVD #361, WINTER HAVEN, FL 33881
$1,60039 Days on yellowkey MLS ID: O6388844
REDUCED by $50 (3.0%) on 04/02/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 2000Community: Winter Ridge CondoCondo
Remarks: AVAILABLE UNFURNISHED CONDO FOR RENT AT THE CHAIN OF LAKES Community of Winter Ridge Condominiums between Lake Smart and Lake Conine! This corner unit property offers stunning views across Lake Smart and the canal to Lake Conine. The master ensuite offers access to the porch with view to enjoy the panorama of the canal and Lake Smart. This spacious bedroom provides a large walk-in closet with loads of organized cabinetry, its bathroom has a tiled walk-in shower. This desirable community has a heated pool, clubhouse, chain of lake access with boat dock, boat slips, and more! Rent includes maintenance of grounds along with trash. It’s a convenient location near Polk state college, Bay Care Hospital, Advent Health, restaurants, and much more. HOA BACKGROUND AND CREDIT APPLICATION Required.
Listing is courtesy of: TWIN HOMES REALTY (407-839-9731)
Listing Agent: Alvaro Molina (407-839-9731)
1341 AVENUE S NW, WINTER HAVEN, FL 33881
$1,89522 Days on yellowkey MLS ID: L4960493
REDUCED by $55 (2.8%) on 04/02/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1566 Built: 1959Community: Stately OaksSingle Family
Remarks: 4/2 home in Winter Haven available now! Features ceramic tile and laminate flooring, inside laundry room, nice yard, and 2 car carport. Approval subject to credit, income, and rental verification.
Listing is courtesy of: SUPERIOR PROPERTY MGMT & SALES (863-853-2770)
Listing Agent: Tracey Crews (863-698-1783)
530 SHORT LN, WINTER HAVEN, FL 33881
$2,20015 Days on yellowkey MLS ID: O6395480
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2254 Built: 2022Community: Inman Grvs Ph 1Single Family
Remarks: LOCATION! LOCATION! LOCATION! This two-story home features a contemporary open space layout in the dining room, kitchen and family room with easy accessibility to the lanai for outdoor relaxing. Upstairs are five bedrooms and a loft as an extra common area. SOLAR SYSTEM IS INCLUDED! SAVE half of your Electricity Bill! The community is close all the major highway, supermarket and restaurant, Legoland is only 10 minutes away, call to schedule a showing.
Listing is courtesy of: U KEY REALTY (407-937-8888)
Listing Agent: Yukey Hoo (407-937-8888)
1458 AUSTIN ST, WINTER HAVEN, FL 33884
$2,10034 Days on yellowkey MLS ID: TB8486395
REDUCED by $50 (2.3%) on 04/01/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1933 Built: 2024Community: Peace Crk ReserveSingle Family
Remarks: Welcome to Peace Creek Reserve! This like-new Atlanta Plan home offers exceptional space and modern living with 4 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The open-concept layout features a spacious great room, dining area, and a beautifully designed kitchen with a large quartz island, stainless steel appliances, ample counter space, and a generous pantry—perfect for everyday living and entertaining. Sliding glass doors lead to a private backyard with serene views, ideal for relaxing and enjoying the peaceful surroundings. Tile flooring runs throughout the main living and wet areas for easy maintenance. Upstairs, you’ll find a versatile loft, a convenient laundry room, and a spacious owner’s retreat with dual vanities, a large walk-in shower, and a walk-in closet. Three additional bedrooms provide plenty of space for family, guests, or a home office. Situated on a peaceful lot with no rear neighbors overlooking a dry pond, this home offers added privacy and tranquil views—a rare find in the community. Located in the master-planned community of Peace Creek Reserve in Winter Haven, known as the Chain of Lakes City with 26 connected lakes, you’ll enjoy nearby shopping, dining, and scenic bike paths while still experiencing a charming small-town atmosphere. Move-in ready! Don’t miss this opportunity to rent a beautiful home in a highly desirable community.
Listing is courtesy of: STAR BAY REALTY CORP. (813-533-6467)
Listing Agent: Shira Bhagavatula (813-533-6467)
258 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881
$2,15041 Days on yellowkey MLS ID: S5145223
REDUCED by $140 (6.1%) on 04/01/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1462 Built: 2020Community: Lucerne Park ReserveSingle Family
Remarks: Beautiful 4-bedroom, 2-bathroom home located in the heart of Winter Haven. This home features ceramic tile flooring throughout the main living areas and a spacious great room with a modern built-in TV wall and electric fireplace. Enjoy peaceful views of the reserve from this premium lot. The master suite offers a spacious walk-in closet and an upgraded shower with a glass door. All bedrooms feature carpet flooring. The open-concept layout includes a large kitchen island, perfect for entertaining and everyday living.
Listing is courtesy of: LA ROSA REALTY INTERNACIONAL L (407-600-7542)
Listing Agent: Ruth Romero (954-687-7155)
2500 21ST ST NW #31, WINTER HAVEN, FL 33881
$1,70042 Days on yellowkey MLS ID: P4938059
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1184 Built: 1975Community: Casa Del Sol Condo Village Ph 01Townhouse
Remarks: Modern 2-Bed, 2.5-Bath Townhome in Desirable Casa del Sol... Step into comfort and convenience in this beautifully designed two-story end unit townhome, perfect for professionals seeking a stylish, low-maintenance lifestyle. Downstairs Living: Formal living room ideal for relaxing or entertaining, Convenient guest half bath, Bright kitchen featuring refrigerator, range, microwave, dishwasher, and breakfast bar, Spacious family/dining room combination that opens to a private screened back porch overlooking the community pool. Upstairs Retreat: Primary bedroom with ensuite bath (tub/shower combo), double built-in closets, and a peaceful screened balcony, Second bedroom with its own private ensuite bath (tub/shower combo), Laundry closet with stackable washer and dryer for added convenience, Additional Features: One-car garage with automatic opener, Private gated front patio entry. Rent includes water and trash collection. Community Amenities for Casa del Sol offers a welcoming community atmosphere with great amenities, including: Clubhouse and pool overlooking scenic Lake Idylwild, Additional centrally located community pool. Conveniently located between Winter Haven and Auburndale and just minutes from Winter Haven Regional Airport, this townhome offers both comfort and accessibility. Schedule your showing today and make Casa del Sol your next home.
Listing is courtesy of: FL REALTY (863-967-0096)
Listing Agent: Dorothea Bogert (863-967-0096)
1101 EAGLE POND DR #1101, WINTER HAVEN, FL 33884
$1,40017 Days on yellowkey MLS ID: S5146256
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1017 Built: 2003Community: Eagle Pond CondoCondo
Remarks: Affordability meets Comfort. First Floor unit for easy access in a highly desirable gated community of Cypresswood Golf & Country Club. This rental will include access to community pool, 24-hour security, exterior maintenance, common area taxes, trash service, pest control, and private road upkeep. Residents can also enjoy an 18-hole golf course, on-site restaurant, tennis courts, and a fitness center. Conveniently accessible to Hwy 27, I-4, medical facilities, Legoland, shopping, & dining. Applicants must complete the application form for pre-screening, once the landlord review the application & ready to proceed there will be an application fee of $50 for a background screening. All applicants 18 years old and above must complete a background screening. Applicants must provide proof of Verifiable Income & must meet landlord minimum income requirements, Proof of Employment, Valid Proof of Identification, & must honestly disclose the number of occupants residing in the home. Showing schedules are by appointment only.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Lienyvette Grimaldo (863-399-0226)
942 CATTLEMAN ST, WINTER HAVEN, FL 33881
$2,30085 Days on yellowkey MLS ID: S5142251
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1560 Built: 2023Single Family
Remarks: Gorgeous 3BR/2BA Home - AVAILABLE FOR APRIL Looking for a hassle-free rental? This beautifully furnished 3-bedroom, 2-bathroom home in Winter Haven is move-in ready! Just unpack and start living. Features You\'ll Love: -Modern Kitchen - Stainless steel appliances & tons of counter space. -Washer & Dryer In-Unit - Laundry made easy. -Attached Garage - Convenient parking & extra storage. -Fantastic Location - Close to Legoland, shopping & dining! $2,300/month | 12-month lease | Utilities separate Pets? Ask for details This won\'t last long! Message now to schedule a tour!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Manuel Paredes (407-840-2272)
2000 15TH CT NW #15, WINTER HAVEN, FL 33881
$1,395163 Days on yellowkey MLS ID: S5137939
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 750 Built: 1973Community: Blount & Whitledge SubApartment
Remarks: One or more photo(s) has been virtually staged. NOW LEASING - AQUA APARTMENT HOMES! MOVE-IN READY! THIS SECOND (2ND) FLOOR UNIT COMES 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. ALL OF OUR LEASES ARE FOR TWELVE (12) MONTHS. APPLICANTS MUST HAVE AN AVERAGE HOUSEHOLD MONTHLY INCOME OF AT LEAST THREE (3) TIMES THE AMOUNT OF RENT. ALL APPLICANTS 18 AND OVER MUST EACH SUBMIT AN APPLICATION, AND UPLOAD COPIES OF IDENTIFICATION, SOCIAL SECURITY, AND PROOF OF INCOME (CURRENT LAST THREE MONTHS OF PAYSTUBS) TO PROCESS YOUR APPLICATION.
2000 15TH CT NW #11, WINTER HAVEN, FL 33881
$1,395163 Days on yellowkey MLS ID: S5137935
Remarks: Now Leasing - Aqua Apartment Homes! Move-in Ready! This 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. 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. All of our leases are for twelve (12) months. All applicants 18 and over must each submit an application, upload copies of Identification, Social Security, and Proof of Income (current last three months of paystubs) to process your application.
3993 WARBLER DR, WINTER HAVEN, FL 33880
$1,85084 Days on yellowkey MLS ID: S5141363
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1750 Built: 2005Community: Queens Cove Ph 04Single Family
Remarks: Lovely 4 bedroom home, conveniently located at the heart of Winter Haven, minutes from all the stores and restaurants, quick access to Polk Parkway & I-4, & takes less than an hour drive to Orlando or Tampa. This gorgeous home features an elegant ceramic tile flooring, a great open floor plan with 2 spacious living areas, dining room, its' kitchen has plenty of cabinets & counter space, a nice screen lanai room, & a spacious backyard. Applicants must complete the application form for pre-screening, once the landlord review the application and ready to proceed there will be an application fee of $55 for a background screening. All applicants 18 years old and above must complete a background screening, submit proof of Verifiable Income, Proof of Employment, & no history of prior eviction. To schedule a showing, prospective applicants must submit a Valid ID, disclose total household monthly income, move-in date, & disclose the number of occupants. Showing schedules are by appointment only.
1192 NORMANDY HEIGHTS CIR, WINTER HAVEN, FL 33880
$2,15071 Days on yellowkey MLS ID: O6379632
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2093 Built: 2009Community: Normandy HeightsSingle Family
Remarks: Welcome to this beautifully renovated 4-bedroom, 3-bath single-family home located at 1192 Normandy Heights Cir, Winter Haven, FL 33880, just minutes from Lake Shipp. This spacious residence features fresh interior paint, brand-new tile flooring, and thoughtful updates throughout. The open kitchen flows seamlessly into a formal dining area, making it ideal for entertaining. Enjoy ample space with both a large living room and a separate family room—perfect for gatherings, relaxing, or hosting guests. Step outside to the expansive screened back porch, ideal for outdoor dining and BBQs. The primary suite offers private access to the patio, creating a peaceful retreat. Tenant is responsible for landscaping. This home combines comfort, space, and a prime location—schedule your showing today! Pets Not Allowed Tenant Liability Insurance **Required**
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Carissa Lawhun (407-207-2220)
748 REGGIE, WINTER HAVEN, FL 33884
$2,60018 Days on yellowkey MLS ID: TB8491693
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1933 Built: 2023Townhouse
Remarks: Welcome to this beautiful tranquil home. Prime Location, Beautiful Community many amenities. Highly sought Peace Creek Reserve Community in Winter Haven. Modern Living in today's busy world. High end kitchen, Many architectural features sets this home off from others. Upgraded bathrooms. Very large space for family gatherings. Large bedrooms. Plenty of storage. Two car garage. Credit Score Required 620. Easy to Show
Listing is courtesy of: GOLDEN SANDS S. FLORIDA REALTY (954-588-1207)
Listing Agent: Donna Galloway (954-588-1207)
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