Displaying: For Rent
Location: Winter Haven
Property Type(s): Single Family
Living Area Square Feet: 1500 to 1999
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Winter Haven - 56 properties found
2102 CHRIS DR, WINTER HAVEN, FL 33884
$2,10021 Days on yellowkey MLS ID: O6413284
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1824 Built: 2026Community: Peace Creek Reserve 50'SSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: South Pointe Elementary
High School: Lake Region High
Tax Year:
Middle School: Westwood Middle
Remarks: Discover comfort and convenience in this beautiful 4-bedroom, 2-bathroom home located in the sought-after Peace Creek Reserve community of Winter Haven. This spacious residence features an open-concept floor plan with a modern kitchen overlooking the dining and living areas, creating the perfect space for everyday living and entertaining. The private primary suite offers a relaxing retreat with an en-suite bathroom and generous closet space. Three additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the covered lanai and backyard space, ideal for relaxing outdoors. Conveniently located near shopping, dining, schools, major highways, and Winter Haven's Chain of Lakes. Lawn care may be included depending on lease terms. Schedule your private showing today and make this beautiful home your next residence.
Listing is courtesy of: NOSSA REALTY LLC (321-558-0990)
Listing Agent: Daniel Serpa (321-558-0990)
1172 TYLER LOOP, WINTER HAVEN, FL 33884
$2,20025 Days on yellowkey MLS ID: O6411165
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1509 Built: 2024Community: Peace Creek Reserve 50SSpa: NoSingle Family
Remarks: One or more photo(s) has been virtually staged. Spacious one-story home for rent featuring 3 bedrooms, 2 full bathrooms, and an office. The home includes quartz countertops, newer appliances, upgraded lighting, ceiling fans, and a fenced backyard with a covered patio. The property also features an In-Law Suite with its own private, separate entrance, which is rented separately. Located in Peace Creek Reserve with access to a community pool, playground, and nearby schools, shopping, and dining.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Rhansel Acevedo Rodriguez (407-668-0143)
942 CATTLEMAN ST, WINTER HAVEN, FL 33881
$2,200154 Days on yellowkey MLS ID: S5142251
0 Days Off yellowkey (back on 5/30/2026)
REDUCED by $100 (4.3%) on 05/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1560 Built: 2023Single Family
Elementary School: None
High School: None
Middle School: None
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)
3711 JULIUS ESTATES BLVD, WINTER HAVEN, FL 33881
$2,10026 Days on yellowkey MLS ID: S5150873
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1842 Built: 2014Community: Lake Smart EstatesSpa: NoSingle Family
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Middle School: Stambaugh Middle
Remarks: Welcome home to this beautifully maintained 4-bedroom, 2-bath rental located in the desirable Lake Smart Estates community of Winter Haven! This spacious home features an open and functional floor plan with high ceilings, a large living and dining area, and a bright kitchen complete with breakfast bar and ample cabinet space. Enjoy laminate flooring throughout, generously sized bedrooms, and a private primary suite designed for comfort and relaxation. Step outside to the screened lanai, perfect for enjoying Florida evenings. Community amenities include a pool and lakefront dock with access to Lake Julius and the Winter Haven Chain of Lakes.
Listing is courtesy of: CENTURY 21 WOLF'S CROSSING REALTY (407-449-0000)
Listing Agent: Stephanie Florez (407-810-5874)
2429 TWIN LAKE VIEW RD, WINTER HAVEN, FL 33881
$2,35028 Days on yellowkey MLS ID: P4938778
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1858 Built: 2018Community: Eagle CrestSpa: NoSingle Family
Remarks: Welcome home to this beautifully maintained 4-bedroom, 2-bath single-family residence in Winter Haven offering 1,860 square feet of thoughtfully designed living space. Featuring rich real wood flooring, this home combines warmth, character, and timeless appeal with the comfort and functionality today’s tenants are looking for. The spacious layout offers generous living areas perfect for both everyday living and entertaining, while the well-designed floorplan provides flexibility for families needing extra bedrooms, a home office, or guest space. Natural light enhances the inviting interior, creating a bright and welcoming atmosphere throughout. Ideally suited for those seeking space, comfort, and a polished residential setting, this home offers the feel of upscale living at an exceptional value. Conveniently located near shopping, dining, schools, and major roadways, residents will enjoy both everyday convenience and the comfort of a well-established Winter Haven location. A rare rental opportunity offering space, style, and classic charm. Schedule your private showing today.
Listing is courtesy of: AMERICAN HOMES REALTY GROUP (800-913-8384)
Listing Agent: Reva Martin (863-206-8478)
2154 CHRIS DR, WINTER HAVEN, FL 33884
$2,19029 Days on yellowkey MLS ID: O6410980
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1880 Built: 2025Community: Peace Creek Reserve 40'SSingle Family
Elementary School: Wahneta Elem
Remarks: FOR RENT! Beautiful and move-in ready home located in the heart of Winter Haven! This charming property offers a bright and spacious floor plan with comfortable living areas, generously sized bedrooms, and a welcoming atmosphere perfect for everyday living. Enjoy a functional kitchen, plenty of natural light, and a peaceful neighborhood setting. Conveniently located near shopping, restaurants, schools, medical facilities, and major highways for easy commuting. This home is clean, well-maintained, and ready for immediate occupancy. Don’t miss this incredible rental opportunity — homes like this lease quickly!
1993 SARAH ST, WINTER HAVEN, FL 33884
$1,99832 Days on yellowkey MLS ID: O6410479
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1838 Built: 2025Community: Peace Crk ReserveSingle Family
Remarks: Welcome to this spacious, modern 4-bedroom, 2-bathroom one-story home in the sought-after Peace Creek Reserve community! Perfectly positioned near Hwy 27, this prime location offers quick access to Legoland, Downtown Winter Haven & Lake Wales, shopping, dining, and the stunning Chain of Lakes—ideal for boating, fishing, and outdoor adventures. Step inside and spoil yourself with the upscale Bloom floor plan, designed for effortless living and entertaining. The open-concept layout features a gorgeous kitchen with a center island, solid surface countertops, and brand-new stainless steel appliances, seamlessly flowing into a cozy café space and a bright, airy family room. Host gatherings with ease or unwind in your private owner’s suite, complete with a serene bedroom, a spa-like bathroom, and a roomy walk-in closet. Three additional bedrooms and a sleek second bathroom provide ample space for family or guests. Everything is included – from the oversized tile flooring in wet areas to the low-maintenance finishes that blend style and practicality. Step outside to your huge backyard, a blank canvas for gardening, play, or future upgrades. Peace Creek Reserve has a tranquil, nature-inspired lifestyle with amenities like a resort-style pool, playground, and scenic walking trails along a peaceful creek. Enjoy the charm of a safe, tight-knit community with the convenience of city living. Winter Haven’s bike paths, lakeside parks, and vibrant downtown ensure there’s always something to explore. This home combines modern luxury with small-town warmth. Don’t miss your chance to live in one of Winter Haven’s most desirable neighborhoods.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Anna Shi (407-216-1215)
2066 KATIE CT, WINTER HAVEN, FL 33884
$2,05571 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)
2587 SAGE VALLEY WAY, WINTER HAVEN, FL 33884
$2,30035 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 Agent: Mardonia Gina (863-513-3056)
3904 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$1,950148 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
$2,30036 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)
279 SUNFISH DRIVE DR, WINTER HAVEN, FL 33881
$2,20044 Days on yellowkey MLS ID: S5149630
REDUCED by $200 (8.3%) on 05/16/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1943 Built: 2021Single Family
Remarks: 4 bedrooms 2 baths for rent in lovely Winter Haven, spacious home with open concept family room, dining and fully equiped kitchen. Home has a laundry room with washer and Dryer. Spacious yard for entertaining family and friends. No neighbors in the back. New tile floors. Bedrooms are carpeted, Community pool.
Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)
Listing Agent: Maria C Diaz (360-627-0493)
728 LAKE NED RD, WINTER HAVEN, FL 33884
$2,00063 Days on yellowkey MLS ID: L4961335
REDUCED by $100 (4.8%) on 05/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1664 Built: 1973Community: Fla Highlands Co SubSingle Family
Remarks: This move-in ready home is located in the Garden Grove area. Minutes away from Lake Ned boat ramp, Legoland, Publix, Walmart, Starbucks, banks, restaurants, and shopping. Home includes stainless steel kitchen appliances, washer and dryer. The home offers neutral colors and tile flooring throughout, a split floor plan, ample storage, interior laundry room, formal living room/bonus room, primary suite with walk-in closet, and the kitchen overlooks the combo family and dining room. Nice sized bedrooms and closets. The home also has a screened-in back porch and a large two-car garage. There is also extra driveway parking. Utilities and lawn maintenance are tenant responsibility. Applications: background check, credit report, $50/adult fee. No pets allowed. Apply online: https://apply.link/d_mhu-4
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Caitlin Meadows (863-845-6562)
330 ROYAL PALM WAY, WINTER HAVEN, FL 33881
$2,40052 Days on yellowkey MLS ID: O6404469
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1790 Built: 2022Community: York HavenSingle Family
Remarks: Newly Built Home! FENCED YARD! Modern Finishes - Energy Efficient. Newly Built Home! FENCED YARD! Modern Finishes - Energy Efficient 330 Royal Palm Way Winter Haven, FL 33881 Be one of the first to move into these recently built, energy-efficient homes, LOADED with the best finishes. If you have pets, not only do we allow them, but we have homes available that include a fenced-in yard! Landscape is included! All appliances are included! The interior finishes include wood look tile throughout, modern kitchens with quartz appliances and stainless steel appliances, 100% LED lighting throughout, and OWNER'S OFFICE connected by a hall on its own side of the house (or use as a fourth bedroom!), ceiling fans in every room, 2" blinds, energy efficient doors and windows, LED lit trays, covered porches, 2 car garage, and a completely JAW DROPPING entryway. YOU WILL NOT FIND A BETTER FEELING HOME FOR YOU AND YOUR FAMILY TO MOVE TO. WE ARE PET FRIENDLY! HURRY UP & APPLY TODAY!
Listing is courtesy of: MY NEW RENTAL (901-550-8381)
Listing Agent: Fernanda Cri Da Silva (407-625-7244)
3022 HICKORY ST NW, WINTER HAVEN, FL 33881
$1,90091 Days on yellowkey MLS ID: A4687467
REDUCED by $100 (5.0%) on 04/26/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1602 Built: 1955Community: Biltmore ShoresSingle Family
Remarks: Welcome to this incredible Winter Haven pool home offering the perfect blend of comfort, upgrades, and true Florida lifestyle living. This move-in ready 3-bedroom home sits on a large oversized lot and is ideal for first-time homebuyers, families, or investors looking for a prime Central Florida opportunity. Step inside to find generous living space, a functional layout, and fresh upgrades that make this property stand out in today’s market. Major Upgrades Include: Brand-new roof – big-ticket item already done, New HVAC system + thermostat – energy-efficient comfort year-round, New water heater, New pool pump & chlorinator – easy, low-maintenance swimming, New laundry units included, New front exterior doors, Expansive driveway with ample parking The private in-ground pool creates your own backyard oasis, while the oversized lot gives you room to expand, build an outdoor kitchen, add a firepit, store boats or recreational toys, or design the ultimate entertaining space. With no mention of restrictive HOA, this property offers flexibility buyers are searching for. Located in the heart of Winter Haven, you’re minutes from everything that makes this area one of Central Florida’s hidden gems. Boat lovers and anglers will love being near Gene’s Lakeside Marina with access to the famous Chain of Lakes — featuring over 50 interconnected lakes perfect for boating, fishing, and waterfront dining. Spend weekends exploring local farmers markets, golfing at one of nine nearby courses, or making family memories at LEGOLAND Florida Resort. Winter Haven is known as the Water Ski Capital of the World and offers a thriving, growing community atmosphere with exciting development underway — including a new hospital opening December 2025, further strengthening property values and long-term investment potential. If you’ve been searching for: • Florida pool home • Move-in ready home in Winter Haven • Large lot property • Investment opportunity in Central Florida • No-fuss upgrades already completed • Close to lakes & boating This is the one. Schedule your private showing today — homes with this many upgrades, a pool, and this location do not last.
Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)
Listing Agent: Ashlee Morrell (941-740-9134)
319 22ND ST SW, WINTER HAVEN, FL 33880
$1,80068 Days on yellowkey MLS ID: O6400245
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1700 Built: 1955Community: West Winter HavenSingle Family
Remarks: This three-bedroom and two-bath home is nearly 1,700 SF. The home is a split floor plan for added privacy of the master suite. The master suite is 15 x 20 and has its own brand-new private bathroom. The living room provides an open concept to entertain guests. The kitchen is bright and airy with a dining area located in the kitchen. The property comes equipped with full sized stackable washer and dryers. The backyard is massive and has plenty of room to store boats, trailers or an RV. The rear yard is also fully fenced for pets. Don't wait and miss out on this opportunity to make this your next home!!
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Robert Kirkwood, Iv (321-297-6489)
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