Location: Winter Haven
Do Not Show Listings
301 SE AVENUE B #2, WINTER HAVEN, FL 33880
$1,00043 Days on yellowkey MLS ID: O6400322
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 1052 Built: 1941Community: East College AddApartment
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: Cozy 1 bed / 1 bath + den with built-in closet, perfect for a home office or guest space, located on the ground floor for easy access. Freshly painted and offering a functional layout with great natural light. Enjoy a shared backyard and on-site coin laundry for added convenience. Includes 1 assigned parking space. Situated in a quiet, well-kept neighborhood near a local school, just 5 minutes from downtown and 10–15 minutes from Legoland, with easy access to shopping and dining. No pets allowed. Available now with a minimum 1-year lease.
Listing is courtesy of: MASIS ROYALTY REAL ESTATE (760-620-2065)
Listing Agent: Liljana Masis (760-620-2065)
1111 CYPRESS GARDENS BLVD SE #12, WINTER HAVEN, FL 33880
$80051 Days on yellowkey MLS ID: L4960990
Bed: 0 Bath: 1.0 Liv Area Sq Ft: 500 Built: 1970Community: Royonne Place ResubApartment
Elementary School: Elbert Elem
Remarks: A studio apartment with 1 bath for rent off of Lake Roy. Included in the rent is Water, and Lawn service. This property does not have a washer or dryer hook-up. Call soon before this property is gone! Application Fee runs $50 per adult with a onetime $50 Lease Fee. For this home we are asking for First Month's Rent ($800), and Security Deposit ($1000) making total move in cost assuming one adult to be $1900 if you move in on the first of the month.
Listing is courtesy of: AT YOUR SERVICE REALTY, LLC (863-665-5663)
Listing Agent: Daniel Gonzalez (863-226-9614)
3511 COSTELLO CIR, WINTER HAVEN, FL 33884
$2,10074 Days on yellowkey MLS ID: O6391046
REDUCED by $100 (4.5%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2234 Built: 2025Community: Villamar Ph 6 & Ph 6DSingle Family
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Middle School: Mclaughlin Academy Of Excellence
Remarks: Like brand new 4-bedroom, 2-bath home located in the desirable Villa Mar community in Winter Haven for rent. This property offers 1,665 sq ft of living space with an open-concept floor plan that connects the kitchen, dining, and living areas, creating a functional layout for everyday living and entertaining. The kitchen features modern finishes, ample cabinet space, and a center island. The primary suite includes a walk-in closet and private bathroom. Three additional bedrooms provide flexibility for guests, office space, or family needs. The home also includes a 2-car garage, driveway parking, and a landscaped yard. Villa Mar residents enjoy community amenities including a swimming pool, playground, dog park, and walking trails. Conveniently located near major roads, shopping, dining, entertainment and more.
Listing is courtesy of: PROPERTY PARTNERS REALTY INC (407-803-1393)
Listing Agent: Patricia Padron (407-803-1393)
140 AVENUE W NW #2, WINTER HAVEN, FL 33881
$1,100117 Days on yellowkey MLS ID: L4958973
REDUCED by $200 (15.4%) on 04/20/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 800 Built: 1974Community: Florence Citrus Growers Assn SubApartment
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything Winter Haven has to offer. Ideal for tenants seeking affordability, convenience, and central location. Available for immediate occupancy!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
7903 WATERVIEW WAY #7903, WINTER HAVEN, FL 33884
$1,600159 Days on yellowkey MLS ID: P4936543
REDUCED by $50 (3.0%) on 04/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 930 Built: 1989Community: Garden Villas Condo Ph 01Spa: NoCondo
Remarks: 2BR/2BA Ground Floor Condo in the Gated neighborhood of Winterset. Wood laminate flooring (no carpet) throughout. New granite countertops and appliances in kitchen. Updated bathrooms. Primary bedroom has a very large walk in closet. Full size washer and dryer included. Community features a clubhouse with swimming pool overlooking Lake Winterset, tennis courts, boat ramp, and dock for fishing. Great SE location near medical, shopping, restaurants, and Legoland! Sorry NO PETS!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Amy Reynolds (863-412-2279)
233 KENSINGTON VIEW BLVD, WINTER HAVEN, FL 33880
$1,97558 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
$1,80043 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)
100 EL CAMINO DR #111, WINTER HAVEN, FL 33884
$1,50043 Days on yellowkey MLS ID: S5148060
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 931 Built: 1971Community: Orchid Spgs Vill 100 CondoSpa: NoCondo
Remarks: Available May 1st — Bright and well-kept 1/1 first-floor condo offering 931 sq ft of comfortable living space and a relaxing pond view from the rear of the unit. Enjoy easy access with no stairs and a peaceful setting. Condo board approval is required for all occupants and pets. One pet under 20 lbs is permitted with association approval. Ideal for anyone seeking a quiet, well-managed community.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Sharon Gastelbondo (863-800-4655)
2014 8TH TER SE, WINTER HAVEN, FL 33880
$3,45043 Days on yellowkey MLS ID: L4961092
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2722 Built: 1959Community: Laha Wa ManorSingle Family
Remarks: A RARE RENT-TO-OWN OPPORTUNITY in the heart of Winter Haven, offering the chance to enjoy lake-view living now while working toward ownership. This beautifully updated 4-bedroom, 3.5-bath home sits just minutes from downtown and the Chain of Lakes, combining location, flexibility, and long-term potential. Inside, the home features a well-designed layout with two primary suites, making it ideal for multi-generational living or those who want additional privacy and space. The main living areas are filled with natural light, highlighted by a warm family room with views of Lake Lulu and French doors that open to a wrap-around screened porch—perfect for relaxing mornings or evening sunsets. The kitchen is equipped with granite countertops, custom maple cabinetry, and stainless steel appliances, while the formal living and dining areas feature original hardwood floors, adding character and charm. Outside, a large paver driveway provides ample parking, and the fenced backyard offers space for entertaining, pets, or family activities. With no HOA, added storage through a two-car garage, and a location close to dining, shopping, and waterfront recreation, this home offers both convenience and lifestyle. This rent-to-own program is ideal for buyers who want to secure a home now while taking the next steps toward mortgage readiness. Homes with lake views, flexible layouts, and ownership pathways like this are rarely available. Serious inquiries only — opportunities like this don’t last.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Chad Lindsey (863-660-7837)
620 REFLECTIONS LOOP, WINTER HAVEN, FL 33884
$1,750241 Days on yellowkey MLS ID: O6348886
0 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1489 Built: 1998Community: Reflections East Ph 01Spa: NoSingle Family
Remarks: Welcome to this spacious 3/2 near Legoland! Nestled in the heart of Winter Haven, FL, this home boasts three generously sized bedrooms and two full bathrooms. The split bedroom floor plan ensures privacy, while the eat-in kitchen nook provides a cozy space for meals. The master suite is a true retreat, complete with a luxurious garden tub. The entire home is outfitted with ceramic tiled flooring, adding a touch of elegance and ease of maintenance. The property also features a large yard, perfect for outdoor activities, and a two-car garage for your vehicles or extra storage. Plus, lawn service and interior pest control are included, providing you with a worry-free living experience. This home offers the perfect blend of comfort, convenience, and style. Don't miss out on this gem in Winter Haven! *Tenant must provide their own washer and dryer. **RESIDENTS BENEFIT PACKAGE Residents are enrolled in the Resident Benefits Package (RBP). There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. RBP includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application. If approved for this home, new tenants must pay a $200.00 lease coordination fee due at the same time as the security deposit payment. **RENTERS INSURANCE REQUIRED $100K min liability coverage. Personal property coverage is not required.
Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)
Listing Agent: Francisco Nieves-Taranto (321-248-4149)
2025 SAN MARCOS DR SE #27, WINTER HAVEN, FL 33880
$1,30079 Days on yellowkey MLS ID: P4938089
REDUCED by $100 (7.1%) on 04/17/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 792 Built: 1984Community: Park LakeApartment
Remarks: Beautiful first-floor apartment, conveniently located near restaurants, shopping, and the hospital. This one-bedroom, one-bathroom home features a granite vanity, a laundry room, and a kitchen with granite countertops. Currently available and a must-see!
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Marisol Padilla (863-604-7252)
6518 CRESCENT LOOP, WINTER HAVEN, FL 33884
$2,25046 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)
3889 GIORGIO DR, WINTER HAVEN, FL 33884
$2,00047 Days on yellowkey MLS ID: V4948423
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1483 Built: 2025Single Family
Remarks: Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven! Offering 3 bedrooms, 2 full bathrooms, this modern residence combines style, functionality, and comfort in one beautifully designed floor plan. Step inside to an open-concept layout filled with natural light, creating the perfect space for both everyday living and entertaining. The primary suite provides a private retreat with a well-appointed en-suite bath, while two additional bedrooms giving flexibility for family, guests, or a home office. Built in 2025, this home offers the peace of mind and energy efficiency of new construction. Home is ideal for growing families or anyone seeking a move-in-ready property in a thriving community. Villa Mar is known for its welcoming, family-friendly atmosphere, featuring sidewalks, green spaces, and convenient access to schools, shopping, dining, and major roadways.
Listing is courtesy of: CENTURY 21 MCBRIDE REALTY GROUP (386-866-1007)
Listing Agent: Paola Martinez (386-866-1007)
4973 KAIA AVE, WINTER HAVEN, FL 33884
$2,00047 Days on yellowkey MLS ID: V4948422
WINTER HAVEN, FL 33881
$1,000430 Days on yellowkey MLS ID: O6293725
Bed: 1 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 400 Built: 2021Single Family
Remarks: Furnished Mini Master Bedroom Suite for rent in beautiful private home. Rent includes all utilities and Wi-Fi. Private fridge available for tenant's use. Owner looking for single professional or travel nurse.
Listing is courtesy of: MAHOGANY REAL ESTATE GROUP (305-971-6161)
Listing Agent: Patricia Townsend (954-732-6322)
1787 LAKEHILL DR, WINTER HAVEN, FL 33884
$4,50053 Days on yellowkey MLS ID: P4938374
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2944 Built: 2024Community: Woodpointe Phase ThreeSingle Family
Remarks: Beautiful 4-bedroom/3.5-bathroom home with additional bonus room ideal for an office, den, gym, or play room in the prestigious Woodpointe community of SE Winter Haven! Elegant custom and designer finishes throughout, screened lanai, walk-in closets, open-concept and split-bedroom floor plan, and so much more. Applications evaluated on creditworthiness and income equal to at least 3x monthly rent and income.
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
1707 EAGLE POND DR #1707, WINTER HAVEN, FL 33884
$1,45052 Days on yellowkey MLS ID: P4938394
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1017 Built: 2009Community: Eagle Pond CondoCondo
Remarks: MOVE-IN READY upstairs Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium includes interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite bathroom while both bedrooms offer walk-in closets. Additional linen storage exists in the main bedroom and hallway, plus an additional outside storage closet offers plenty of room to store all of your extras. The Cypresswood community features an 18-hole championship golf course designed by Ron Garl, junior Olympic-sized community pool, lighted tennis courts, clubhouse, event space, and so much more. The pool and tennis amenities are INCLUDED with your lease! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options, this one will surely not last long. Monthly rent includes maintenance and repairs, pest control, and trash collection. Up to three pets allowed with prior approval; applications approved based on creditworthiness and income equal to at least 3x monthly rent, otherwise additional security deposit may be required.
2772 SAN MARCO WAY, WINTER HAVEN, FL 33884
$2,20052 Days on yellowkey MLS ID: O6397232
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1988 Built: 2024Community: VillamarSpa: NoSingle Family
Remarks: Welcome to the desirable Villamar community in Winter Haven, where comfort, convenience, and modern living come together in one of the area’s fastest-growing neighborhoods. This FULLY FENCED like-new 4-bedroom, 3-bathroom home offers a thoughtfully designed layout that perfectly balances functionality and style, making it ideal for families, entertaining, or simply enjoying everyday life. Designed with both comfort and connection in mind, the open-concept floor plan flows effortlessly through the main living areas. The spacious great room opens to the dining area and kitchen, creating a bright and inviting atmosphere filled with natural light. The kitchen overlooks the living space, allowing you to stay connected with family and guests while preparing meals, making it the true heart of the home. Location truly sets this home apart. Villamar offers a variety of community amenities including a pool, playground, dog park, and scenic walking paths, creating a lifestyle that’s both active and relaxing. Just minutes away, you’ll find everyday conveniences like Publix and Walmart, along with quick access to US-27 for an easy commute. Enjoy weekends full of fun just 5 minutes from LEGOLAND Florida Resort, or take a short 10-minute drive to explore dining, shopping, and entertainment in downtown Winter Haven. Zoned near local elementary and middle schools just minutes away, this home offers convenience for families at every stage. This is more than just a home, it’s a lifestyle opportunity in one of Central Florida’s most convenient and growing communities. Don’t miss your chance to own this beautiful, move-in ready home in Villamar. Schedule your private tour today!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Fanny Stollmeyer (704-905-0698)
1550 11TH ST NE #B6, WINTER HAVEN, FL 33881
$1,425109 Days on yellowkey MLS ID: L4959252
0 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1148 Built: 1974Community: Lake Buckeye CondoCondo
Remarks: Enjoy this modern, remodeled 2/2 condo. This condo features granite countertops and has a washer/dryer inside the unit. Enjoy the most peaceful views of the lake and pool from the back porch. Renters insurance is required.
Listing is courtesy of: TRIBUTE REALTY LLC (863-450-2910)
Listing Agent: Mindy Emerson-Hunley (863-669-0528)
2214 Ave B SW SW 2214 AVE B SW, WINTER HAVEN, FL 33880
$1,77558 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)
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