Displaying: For Rent
Location: Winter Haven
Property Type(s): Single Family
Price: $1,500 to $1,999
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Winter Haven - 47 properties found
3904 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$1,950149 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
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)
810 TERRANOVA RD, WINTER HAVEN, FL 33884
$1,90050 Days on yellowkey MLS ID: S5149408
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2056 Built: 2006Community: Terranova Ph VSingle Family
Remarks: FOR RENT: Spacious 4 bedrooms and 2 bathrooms all tile home ready to move in. Large open kitchen combo family room. Seperate laundry room.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Mark Peters (407-552-1499)
3022 HICKORY ST NW, WINTER HAVEN, FL 33881
$1,90092 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)
233 KENSINGTON VIEW BLVD, WINTER HAVEN, FL 33880
$1,97584 Days on yellowkey MLS ID: O6395911
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1491 Built: 2021Community: Kensington ViewSingle Family
Remarks: Discover modern living in this stunning newly built 3-bedroom, 2-bath home, where style meets comfort. Bright, spacious bedrooms provides the perfect retreat, while sleek, thoughtfully designed bathrooms add a touch of luxury. The open-concept layout flows effortlessly from the kitchen to the living and dining areas, ideal for entertaining or relaxing. A generous walk-in closet keeps everything organized in style. Step outside to your private, pet-friendly backyard, perfect for play, lounging, or weekend barbecues. With high-end finishes, abundant natural light, and a warm, welcoming vibe, this move-in-ready home is everything you’ve been looking for. Don’t miss the home you've been looking for! Excuse the front facing photo of property. Yard has been maintained and cleaned.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Christopher Gallon, Pa (407-967-9363)
319 22ND ST SW, WINTER HAVEN, FL 33880
$1,80069 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)
2214 Ave B SW SW 2214 AVE B SW, WINTER HAVEN, FL 33880
$1,77584 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
High School: Winter Haven Senior
Middle School: Denison Middle
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)
1756 2ND ST NE, WINTER HAVEN, FL 33881
$1,600329 Days on yellowkey MLS ID: P4935670
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 626 Built: 1938Community: Maud MeadowsSingle Family
Elementary School: Frank E. Brigham Academy
Remarks: VACANT, MOVE-IN READY & PET FRIENDLY! Lease for just $1,600/month! Located in the lovely and up-and-coming Winter Haven area, this completely remodeled historic 1930s home has been beautifully restored to its former glory. This charming home offers 2 bedrooms and 1 well-appointed full bathroom, perfect for comfortable living. Situated on an oversized, fully fenced corner lot—perfect for pets—the backyard provides peace of mind and privacy. A wooden picnic bench and table add convenience for enjoying your morning coffee or relaxing outdoors. Inside, enjoy a cozy open floor plan filled with natural light. Recent updates include: new appliances, tankless water heater, roof with decking, plumbing, electrical, wood cabinets, and quartz countertops. All major systems have been updated—this is a true turnkey home! Utilities to be covered by the tenant. Do NOT wait, it will NOT last long! Contact us today to schedule a showing!
Listing is courtesy of: HUT TEAM REALTY (407-559-2929)
Listing Agent: Daniel Hut (863-400-6090)
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