Displaying: For Rent
Location: Winter Haven
Property Type(s): Single Family
Price: $1,500 to $1,999
Do Not Show Listings
Winter Haven - 38 properties found
603 TERRANOVA DR, WINTER HAVEN, FL 33884
$1,9858 Days on yellowkey MLS ID: B4902246
0 Days Off yellowkey (back on 5/1/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1699 Built: 2004Community: Terranova Ph 01ASingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Tax Year:
Middle School: Denison Middle
Remarks: Move In Ready 4 bedroom 2 bathroom home in the gated community of Terranova. This home has been well maintained and boasts fresh interior paint Ceramic Tile throughout the home. Located close to shopping, restaurants, and Lego Land. The tenants will benefit from the solar panels with the average electric costs for the previous tenants have been less than $100.00 month. Home offers vinyl fenced rear yard, screen room, and open floor plan. This home will not disappoint.
Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)
Listing Agent: Craig Burke (863-899-5010)
4819 SUMMERFIELD CIR, WINTER HAVEN, FL 33881
$1,800138 Days on yellowkey MLS ID: O6366521
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1688 Built: 2016Community: Country Club EstatesSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: Super Cute Home features 4 bedroom, 2 bath, 2 car garage home, located in Country Club Estates. Freshly painted a neutral color, tile in living areas and brand new LVP in bedroom. Living room kitchen combo, great for family time. Call today for a showing!
Listing is courtesy of: ORLANDO REO PROF I INC (407-704-6924)
Listing Agent: Ronald Gentile (407-247-0849)
2007 9TH ST NE, WINTER HAVEN, FL 33881
$1,8004 Days on yellowkey MLS ID: S5148784
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1242 Built: 1967Community: Lake Idyll EstatesSingle Family
Remarks: Welcome to this well-maintained home located at 2007 9th St NE, offering comfort, convenience, and a prime location. This inviting property features a spacious layout with plenty of natural light, creating a warm and welcoming atmosphere throughout. The home offers a functional kitchen with ample cabinet space, perfect for everyday living and entertaining. Enjoy comfortable bedrooms, well-sized living areas, and a layout designed for both relaxation and practicality. Step outside to a generous yard—ideal for outdoor enjoyment, gatherings, or simply unwinding after a long day. Conveniently located near shopping, dining, schools, and major roadways, this home provides easy access to everything in Winter Haven, including nearby lakes and recreational areas. Key Features: * Spacious living areas * Ample natural light * Functional kitchen with storage * Private yard space * Convenient location near amenities Don’t miss this opportunity to make this charming property your next home—schedule your showing today!
Listing is courtesy of: RODRIGUEZ PROPERTY MANAGEMENT (407-936-4061)
Listing Agent: Francisco Medina (407-931-6738)
1744 TEAGAN LN, WINTER HAVEN, FL 33884
$1,8004 Days on yellowkey MLS ID: S5148933
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1444 Built: 2024Community: Peace Crk ReserveSingle Family
Elementary School: South Pointe Elementary
Middle School: Westwood Middle
Remarks: Beautiful Property | 3 Bedrooms | 2 Bathrooms | Peace Creek Reserve. This beautiful single-family home featuring 3 bedrooms and 2 bathrooms, located in the desirable Peace Creek Reserve community. This move-in ready home offers a modern open floor plan, ideal for comfortable living and entertaining. The upgraded kitchen includes quartz countertops, solid cabinets, and stainless-steel appliances (refrigerator, dishwasher, microwave, and range). The home features tile flooring throughout the main living areas, with cozy bedrooms and elegant bathrooms with quartz finishes. Enjoy added value with a conservation lot with no rear neighbors, providing privacy and peaceful views, plus window blinds already installed. Conveniently located near shopping centers, supermarkets, restaurants, and major highways, with easy access to outdoor attractions like parks, lakes, Bok Tower Gardens, and Lake Kissimmee State Park.
Listing is courtesy of: A & V FLORIDA REALTY GROUP LLC (786-641-7923)
Listing Agent: Edgar Brito (786-641-7923)
2893 WHISPERING TRAILS DR, WINTER HAVEN, FL 33884
$1,75040 Days on yellowkey MLS ID: S5146531
REDUCED by $150 (7.9%) on 04/30/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1268 Built: 2017Community: Whispering Trails Ph 02Single Family
Elementary School: Elbert Elem
High School: Winter Haven Senior
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)
1228 HAINES DR, WINTER HAVEN, FL 33881
$1,9956 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 is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Hector Figueroa (939-241-0047)
3992 WARBLER DR, WINTER HAVEN, FL 33880
$1,8005 Days on yellowkey MLS ID: S5148815
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1632 Built: 2004Community: Queens Cove Ph 04Single Family
Remarks: Lovely home at a convenient location in 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. The home offers a comfortable floor plan with a magnificent living room, fabulous master suite w/ walk-in closet & ensuite bathroom, & the formal dining area overlooking the lanai & backyard. The home is meticulously well-maintained. Rent With Confidence: lease terms can be flexible to applicants who are planning to purchase a home in the future or expecting a job relocation. Applicants are required to complete the application form for pre-screening, once the landlord review the application and ready to proceed there will be an application fee of $50 for a background screening for all applicants 18 years old and above. Applicants must submit proof of verifiable income, proof of employment, valid proof of identification, & must honestly disclose the number of occupants residing in the home. Applicants to submit paystubs, recent W2, or any proof of documentation meeting the landlord income requirements. Showing schedules are by appointment only.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Lienyvette Grimaldo (863-399-0226)
1776 CARNOSTIE RD, WINTER HAVEN, FL 33884
$1,8007 Days on yellowkey MLS ID: O6402709
0 Days Off yellowkey (back on 4/29/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 2022Single Family
Remarks: AVAILABLE MAY 1ST!!! Welcome to this wonderful house at the Villa Mar in Winter Haven! With plenty of natural light, this home features 3 comfortable bedrooms, 2 bathrooms, a spacious open concept floor with a living room, a kitchen with an island, breakfast bar, elegant cabinets, all stainless-steel appliances and granite countertops. The Villa Mar Community features amenities such as a playground, swimming pool and Clubhouse. Very well located, it’s just minutes from restaurants, shopping malls, and world-famous theme parks! Don't miss this opportunity and schedule your visit today!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Alessandra Barreto (732-762-8180)
WINTER HAVEN, FL 33880
$1,81920 Days on yellowkey MLS ID: TB8497765
REDUCED by $30 (1.6%) on 04/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1300 Built: 2010Community: Central PointeSingle Family
Remarks: Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, 2 bathrooms, 2 car garage and approximately 1,300 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated. Applications are First Come First Serve basis. Variable Rent Option – go to “Apply” on website and select Term for monthly rental options. This home is professionally managed and maintained by Owner. You deserve single family rental living at its best!
Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)
Listing Agent: Cathy Behe (689-244-9559)
WINTER HAVEN, FL 33884
$1,97920 Days on yellowkey MLS ID: TB8497756
REDUCED by $20 (1.0%) on 04/29/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2150 Built: 2006Community: Whispering Trls Ph 01Single Family
Remarks: Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, _3 bathrooms, 2 car garage and approximately 2,150 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated. Applications are First Come First Serve basis. Variable Rent Option – go to “Apply” on website and select Term for monthly rental options. This home is professionally managed and maintained by Owner. You deserve single family rental living at its best!
$1,7496 Days on yellowkey MLS ID: TB8502889
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1540 Built: 2023Community: Peace Crk ReserveSingle Family
Remarks: Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage and approximately 1,555 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated. Applications are First Come First Serve basis. Variable Rent Option – go to “Apply” on website and select Term for monthly rental options. This home is professionally managed and maintained by Owner. You deserve single family rental living at its best!
165 OSPREY HEIGHTS DR, WINTER HAVEN, FL 33880
$1,67548 Days on yellowkey MLS ID: P4938155
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1393 Built: 2003Community: Osprey Landings Ph 02Single Family
Remarks: Welcome home to 165 Osprey Heights Drive! This well-maintained 3-bedroom, 2-bath home offers a desirable split floor plan, providing both privacy and functionality. The home features brand-new vinyl flooring in the main living areas and fresh interior paint, giving it a clean, updated feel throughout. The bedrooms are comfortably carpeted, creating a warm and cozy retreat. The kitchen is both cute and functional with plenty of space to cook and gather. Additional highlights include a two-car attached garage for convenient parking and storage, plus a small shed in the backyard for extra space to keep tools, lawn equipment, or outdoor items organized. This home is move-in ready and waiting for its next Tenant. Schedule your showing today!
Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)
Listing Agent: William Beasley (863-299-1256)
4981 KAIA AVE, WINTER HAVEN, FL 33884
$1,9006 Days on yellowkey MLS ID: O6400860
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 2025Community: Villamar Ph 6 & 6DSingle Family
Remarks: Welcome to this beautiful brand new property in winter I am pleased to introduce a wonderful opportunity located at , Winter Haven. This 3-bedroom, 2-bathroom property was recently built in 2025 and offers a modern living space in a prime location. The home is ideally situated close to Highway 27, providing easy access to major commuting routes while remaining conveniently located near a variety of local stores and amenities. Come see this beauty for yourself.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Jorge Barcelo (407-267-8415)
400 RED HAWK LOOP, WINTER HAVEN, FL 33880
$1,6007 Days on yellowkey MLS ID: L4961436
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1056 Built: 1995Community: Spirit Lake Village Ph 01Single Family
Remarks: 3BR/2BA home available now in Winter Haven. Home features all ceramic tile flooring, single car garage, and spacious yard on a corner lot.
Listing is courtesy of: SUPERIOR PROPERTY MGMT & SALES (863-853-2770)
Listing Agent: Tracey Crews (863-698-1783)
1341 AVENUE S NW, WINTER HAVEN, FL 33881
$1,79540 Days on yellowkey MLS ID: L4960493
REDUCED by $100 (5.3%) on 04/27/2026
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.
235 HAYLEY ST, WINTER HAVEN, FL 33884
$1,80045 Days on yellowkey MLS ID: S5146226
0 Days Off yellowkey (back on 4/27/2026)
REDUCED by $100 (5.3%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1432 Built: 2024Community: Peace Crk ReserveSpa: NoSingle Family
High School: Bartow High
Middle School: Bartow Middle
Remarks: Beautiful 3-bedroom, 2-bathroom home located at 235 Hayley St, Winter Haven, FL 33884. This well-maintained property offers a comfortable and functional layout, perfect for families or anyone seeking a peaceful living environment. Enjoy a bright and inviting interior, with spacious living areas and a practical floor plan designed for everyday living. The home provides a great balance of comfort and convenience. Pet-friendly (with breed and size restrictions), making it a great option for tenants with pets. Ideally situated in a desirable area of Winter Haven, this home offers easy access to shopping centers, restaurants, schools, and major roadways. The community is known for its quiet atmosphere, family-friendly environment, and proximity to beautiful lakes and outdoor recreational areas. Don’t miss the opportunity to live in a well-located home that combines comfort, convenience, and lifestyle.
Listing Agent: Djanira Puyosa (407-717-5231)
227 VOLUSIA DR, WINTER HAVEN, FL 33884
$1,90027 Days on yellowkey MLS ID: P4938372
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1250 Built: 1974Community: Eloise Woods Lake Mariam UnitSingle Family
Remarks: Located in an established neighborhood this home offers 2 bedrooms and 2 bathrooms. Galley kitchen overlooking large fenced backyard with mature landscaping and plenty of shade. Inside laundry room and 2 car garage with room for storage. New interior paint throughout. Laminate flooring throughout. Located close to schools, shopping and medical facilities. Central location in between Orlando and Tampa. Minutes to Legoland. Available and ready for immediate occupancy.
Listing is courtesy of: THE HOME COMPANY (863-268-8157)
Listing Agent: Sue Ann Williamon (863-258-3115)
3022 HICKORY ST NW, WINTER HAVEN, FL 33881
$1,90040 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)
3063 LAUREL OAK LN, WINTER HAVEN, FL 33884
$1,69575 Days on yellowkey MLS ID: O6369521
REDUCED by $100 (5.6%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1269 Built: 2023Community: VillamarSpa: NoSingle Family
Remarks: 2ND MONTH RENT FREE: Move-In Ready, Pet-Friendly, 2-Car Garage! Available for immediate occupancy! Step into this stunning 2023 Meritage Home in the heart of Winter Haven, Florida—a highly upgraded 3-bedroom, 2-bath single-story home designed to impress. This move-in ready home features neutral tones throughout, a chef-inspired kitchen with stainless steel appliances, quartz countertops, and a large island perfect for entertaining. The master suite boasts a walk-in closet, dual sinks, and a spacious shower, while additional bedrooms are generously sized. Enjoy the convenience of an indoor laundry room with washer and dryer, an energy-efficient design, and a 2-car garage. Pet-friendly and thoughtfully designed for comfort, the home also includes a paver driveway and patio slab. Residents of VillaMar enjoy resort-style amenities, including a sparkling pool overlooking a gorgeous lake, umbrellas, loungers, a playground, and community mailboxes. Don’t wait—schedule your showing today! Sorry No Cats.
Listing is courtesy of: RENT A FLORIDA HOME (863-232-6262)
Listing Agent: Katrina Anarumo (863-232-6262)
729 CRESTWOOD DR, WINTER HAVEN, FL 33881
$1,55012 Days on yellowkey MLS ID: R4911103
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1156 Built: 1960Community: CrestwoodSingle Family
Elementary School: Inwood Elem
Remarks: This 3-bedroom, 1-bathroom home at 729 Crestwood Dr in Winter Haven offers a comfortable and practical living space in a quiet, cozy community. Featuring hardwood floors throughout, the home provides a clean, classic feel that’s easy to maintain. A dedicated laundry room includes washer and dryer hookups for added convenience. Step outside to a spacious backyard complete with a storage shed—perfect for keeping tools, equipment, or seasonal items organized. Conveniently located near local amenities, this home offers both comfort and accessibility. Section 8 vouchers are welcome.
Listing is courtesy of: CORA PROPERTIES LLC (863-651-2139)
Listing Agent: Jaquis Mccullough (863-651-2139)
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