Location: Winter Haven
Do Not Show Listings
252 SANTA ROSA DR, WINTER HAVEN, FL 33884
$2,495140 Days on yellowkey MLS ID: TB8470100
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2116 Built: 1988Community: Overlook EstatesSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Great location. Perfect place to call home. 3 bedroom 2 bath spa/pool home with garage. Located in gated community-overlook estates. Minutes from lego-land. Home offers a kitchen, dining room and a formal dining room. 3rd bedroom has a Murphy bed and built in desk/office area. Master features french doors leading to the pool &spa. Offers walk in closets throughout home. Mature landscaping. Lots of space. Give us a call today , you wont be disappointed. Available may 1st 2026
Listing is courtesy of: PRESTIGE LIFESTYLES REALTY (866-863-1166)
Listing Agent: Jennifer Geiger (407-506-5387)
213 LAKE LUCERNE WAY, WINTER HAVEN, FL 33881
$1,90096 Days on yellowkey MLS ID: O6390973
REDUCED by $100 (5.0%) on 06/06/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1717 Built: 2018Single Family
Remarks: Welcome to your next home! This well-maintained 4-bedroom, 2-bathroom home offers 1,701 sq. ft. of comfortable living space with an open-concept layout that creates a bright and inviting atmosphere—perfect for relaxing or entertaining family and friends. Located in a friendly and welcoming community, residents enjoy access to the community pool and playground, providing great options for outdoor enjoyment. The home is ideally situated just minutes from Highway 27, offering convenient access to everyday essentials, shopping, and dining. Posner Park is a short drive away and features a variety of retail stores, restaurants, and entertainment options. Grocery stores such as Publix and Walmart are nearby, along with popular local restaurants including Manny’s Chophouse and other dining options along Highway 27. With its spacious layout and prime Central Florida location, this home offers the perfect blend of comfort, convenience, and community living. Available for move-in June 1st.
Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)
Listing Agent: Yashira Arroyo Colon (407-864-4904)
504 TWIN BOWFISH WAY, WINTER HAVEN, FL 33881
$2,15033 Days on yellowkey MLS ID: O6408732
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1989 Built: 2022Community: Lake Lucerne Ph 5Single Family
Remarks: Welcome to your next home! This beautifully maintained 4-bedroom, 2-bathroom home offers an impressive 1,989 sq. ft. of comfortable living space designed for both everyday living and entertaining. Featuring a spacious open-concept layout, this home provides a bright and inviting atmosphere with plenty of room to enjoy with family and friends. Step outside and enjoy the added privacy of a fully fenced backyard and a screened enclosure, perfect for relaxing outdoors, entertaining guests, or enjoying Florida living year-round. Ideally located in a growing and desirable area, this home is just minutes from Highway 27, providing easy access to shopping, dining, and everyday conveniences. Plus, it is conveniently close to the new Super Target expected to open by December 2026, adding even more convenience and value to the location. Nearby, you’ll also find grocery stores, restaurants, and shopping destinations, including Posner Park, Publix, Walmart, and popular dining options along Highway 27. Offering the perfect blend of space, comfort, convenience, and outdoor enjoyment, this Central Florida home is one you won’t want to miss! available August 1st!
2371 BRASSIE CT, WINTER HAVEN, FL 33884
$2,350101 Days on yellowkey MLS ID: O6389720
INCREASED by $100 (4.4%) on 06/05/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2522 Built: 2022Community: Villamar Ph 3Single Family
Remarks: Ready to move in 5-bedroom, 3-bathroom home offers the perfect blend of modern comfort, energy efficiency, and scenic beauty. GREAT NEWS the house have solar panels and you will only need to pay a low electricity bill. Located in the desirable VillaMar community, this spacious home features an open-concept layout ideal for family living and entertaining. Enjoy peaceful mornings with breathtaking pond views right in your backyard — your private retreat for relaxation and tranquility. The home also includes solar panels, helping you save on energy bills while living sustainably. With elegant finishes, a large kitchen, and plenty of natural light throughout, this home is move-in ready and waiting for its new owners. Features resort-style community amenities including a zero-entry swimming pool with a lap lane, a playground, a dog park and sidewalks.Conveniently located near shopping, restaurants, and top-rated schools — this is the lifestyle you’ve been looking for in Winter Haven!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Karina Turcios (407-346-7606)
693 REGGIE RD, WINTER HAVEN, FL 33884
$2,30040 Days on yellowkey MLS ID: S5149706
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1933 Built: 2024Community: Peace Crk ReserveSingle Family
Elementary School: Wahneta Elem
High School: Lake Region High
Middle School: Westwood Middle
Remarks: READY TO MOVE !!!! This almost 1900 sq ft beautiful two-story home features four bedrooms, two and a half baths, and a two-car garage. The perfect plan with the perfect color scheme makes this home stand out compare to others that are similar. It provides an open floor plan with great room, dining room, and kitchen with large island. The kitchen features ample counter space, and generous pantry. The casual dining area allows outdoor access to a large backyard via sliding glass doors. The second floor includes an owner's retreat featuring an owner's bath with large walk-in shower, dual vanity, and spacious walk-in closet. Three additional bedrooms, a bathroom, a spacious loft, and laundry room finish off this beautiful home. This home comes fully equipped with Everything Included Features like new appliances, solid surface countertops throughout and oversized tile flooring in the wet areas. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to live.
Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)
Listing Agent: Adriana Sanchez (321-947-4014)
1228 HAINES DR, WINTER HAVEN, FL 33881
$1,85053 Days on yellowkey MLS ID: S5148202
REDUCED by $145 (7.3%) on 06/04/2026
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)
1343 BENEVENTO DR, WINTER HAVEN, FL 33884
$2,00017 Days on yellowkey MLS ID: O6413294
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1849 Built: 2020Community: Villamar Ph 2Single Family
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bathroom home in the highly sought-after Villamar community of Winter Haven. Built by Meritage Homes, this move-in-ready residence features a thoughtfully designed open-concept floor plan, perfect for both everyday living and entertaining. The spacious kitchen overlooks the great room and showcases granite countertops, stainless steel appliances, ample cabinetry, and a large walk-in pantry. The desirable triple-split bedroom layout provides privacy and flexibility, with two secondary bedrooms and a guest bath near the front of the home, a separate fourth bedroom ideal for guests or a home office, and a private primary suite tucked away at the rear of the property. The primary retreat boasts dual vanities, a beautifully tiled walk-in shower, and a generous walk-in closet. Ceramic tile flooring flows throughout the main living areas, while the bedrooms provide the comfort of carpeting. Residents of Villamar enjoy outstanding community amenities, including a resort-style pool overlooking Crystal Lake, a playground, and convenient community mailboxes. Ideally located near shopping, dining, medical facilities, and LEGOLAND Florida Resort, with easy access to US Highway 27 for commuting to Orlando and surrounding Central Florida destinations. Don't miss this opportunity to own a beautiful home in one of Winter Haven's fastest-growing communities.
Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)
Listing Agent: Jose Rojo (786-502-6162)
2102 CHRIS DR, WINTER HAVEN, FL 33884
$2,10017 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
Elementary School: South Pointe Elementary
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)
2414 AVENUE A TER NW, WINTER HAVEN, FL 33880
$1,900275 Days on yellowkey MLS ID: L4955978
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1955Community: Haven HomesSingle Family
Remarks: ~Charming 3/2 Winter Haven Residence Offered for Lease~ Just steps away from Lake Deer, this home features a neutral color scheme throughout, bonus room that could be used as a 4th bedroom/office/media room, beautiful galley style kitchen with granite counters, stainless steel appliances and wood cabinetry, generous sized rooms, inside utility/laundry room, sizeable fenced yard, shed and a one-car carport. Convenient to all that Winter Haven has to offer!
Listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM (863-940-3756)
Listing Agent: Andrea Muzzy (863-430-1733)
6433 DOMIZIO DR, WINTER HAVEN, FL 33884
$2,30018 Days on yellowkey MLS ID: O6412555
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2112 Built: 2026Community: Villa Mar 40'SSingle Family
Elementary School: Pinewood Elem
Middle School: Denison Middle
Remarks: Spacious New 5-Bedroom Residence Available for Lease in Winter Haven Experience the comfort of a never-before-occupied home in one of Winter Haven’s growing residential communities. This newly completed two-story property offers an impressive combination of space, modern design, and everyday convenience, featuring five bedrooms, two full bathrooms, and a guest powder room. The thoughtfully designed layout provides generous living spaces that flow seamlessly from one room to another, creating an inviting environment for both entertaining and daily family life. Abundant natural light fills the interior through oversized windows, enhancing the home's bright and airy feel. At the heart of the home, the contemporary kitchen showcases quality craftsmanship with rich wood cabinetry, sleek stone surfaces, and a full package of stainless-steel appliances. Whether preparing weeknight meals or gathering with friends and family, this space is designed to accommodate both functionality and style. The primary bedroom serves as a relaxing retreat, offering ample space, a large walk-in wardrobe, and a well-planned layout for privacy and comfort. Secondary bedrooms are generously proportioned and feature built-in closet storage, providing flexibility for family members, guests, or home office needs. Additional features include an attached two-car garage, modern fixtures and finishes throughout, and the advantages of energy-efficient construction designed to help reduce utility costs while enhancing year-round comfort. Ideally positioned near shopping centers, restaurants, schools, and major transportation routes, residents will enjoy convenient access to everyday necessities while benefiting from the peaceful atmosphere of a residential neighborhood. This exceptional rental presents a rare opportunity to enjoy the benefits of a brand-new home with abundant living space, contemporary finishes, and a convenient Winter Haven location.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Alexandre Zapparoli (321-444-8701)
1200 6TH ST NE, WINTER HAVEN, FL 33881
$1,58519 Days on yellowkey MLS ID: TB8514467
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1944Community: Shepard & Acree AddSingle Family
Remarks: Ask about our move in special ! Charming 3 bedroom home in Winter Haven featuring a large yard perfect for outdoor living, play, or weekend gatherings. Call today to view
Listing is courtesy of: PALM LEAF PROPERTY MANAGEMENT (813-616-6000)
Listing Agent: Jordan Clark (813-616-6000)
1172 TYLER LOOP, WINTER HAVEN, FL 33884
$2,20021 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
$2,200150 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
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
$2,10022 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
$2,35024 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)
1313 DIEGO TER #In-Law Suite, WINTER HAVEN, FL 33884
$1,300115 Days on yellowkey MLS ID: O6385566
REDUCED by $100 (7.1%) on 05/27/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 2093 Built: 2024Community: Peace Crk ReserveSpa: NoSingle Family
Elementary School: Chain O Lakes Elem
High School: Bartow High
Middle School: Bartow Middle
Remarks: One or more photo(s) has been virtually staged. For Lease: Private In-Law Suite in Winter Haven, FL – $1,300/Month Looking for a clean, private rental in Winter Haven? This 450 sq. ft. in-law suite offers comfortable living in a quiet, well-located neighborhood. Important: This is a separate in-law suite attached to the main home. The main house is owner-occupied. This listing is not for the full home. Property Features: Rent: $1,400 /month Size: Approx. 450 sq. ft. Lease Term: Minimum 12 months Security Deposit: $1,300.00 Move-In Costs: First month’s rent + security deposit Application Fee: $50 (non-refundable) Max Occupancy: 2 Parking: Street parking only Amenities: Access to community pool Access to playground area Additional Details: Pets: No pets allowed Utilities: Included (Electric, Water, Internet) Private entrance for added privacy This rental is ideal for a single tenant or couple looking for an affordable, low-maintenance home near shopping, dining, and major roads in Winter Haven. Great location with easy access to local amenities and highways.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Andrea Jastemski (813-516-0865)
2154 CHRIS DR, WINTER HAVEN, FL 33884
$2,19025 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
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!
1705 3RD ST NW #A, WINTER HAVEN, FL 33881
$1,65037 Days on yellowkey MLS ID: L4961475
REDUCED by $50 (2.9%) on 05/26/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1472 Built: 2023Community: Inmans AllotmentSingle Family
Remarks: 1/2 DUPLEX - UNIT A Be the next to enjoy this newer construction (2023) 3-bedroom, 2-bathroom duplex unit offering 1,472 sq ft of modern living! Unit A features a bright open-concept floor plan with tile flooring throughout the entire unit, a spacious living room and dining room area, and a well-appointed kitchen with stainless steel appliances, granite countertops, and ample cabinetry. The home includes a beautifully tiled shower, generously sized bedrooms with large closet space, and a dedicated indoor laundry room for added convenience. Neutral finishes throughout create a clean, modern feel. You will find this unit to be conveniently located near downtown Winter Haven where there is plenty of shopping, dining, and near major roadways. Note: This is Unit A. See separate listing for Unit B.
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Chelsey Collins (863-873-3989)
326 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881
$2,600106 Days on yellowkey MLS ID: S5144995
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2696 Built: 2021Community: Lucerne Park ReserveSingle Family
Remarks: One or more photo(s) has been virtually staged. Welcome to this stunning two-story rental home located in the heart of Winter Haven! Built in 2021, this spacious 4-bedroom, 2.5-bath residence offers 2,696 sq. ft. of thoughtfully designed living space, combining modern comfort with everyday functionality. The open floor plan features a bright and inviting living area, perfect for relaxing or entertaining guests. The kitchen offers ample cabinetry and generous counter space — ideal for meal prep, hosting, and daily living. Upstairs, you’ll find generously sized bedrooms that provide comfort and privacy for the entire household. Enjoy added peace of mind with a recently repaired roof and the benefit of newer construction. Perfectly situated with convenient access to the best of Winter Haven, including shopping, dining, schools, and major roadways. Now available for lease — don’t miss the opportunity to make this beautiful property your next home. Schedule your private showing today.
Listing is courtesy of: NORKIS & CO REALTY (407-506-7070)
Listing Agent: David Gonzalez Martell, Pa (407-760-0792)
1993 SARAH ST, WINTER HAVEN, FL 33884
$1,99828 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 Agent: Anna Shi (407-216-1215)
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