Location: Winter Haven
Do Not Show Listings
257 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881
$284,500173 Days on yellowkey MLS ID: P4937588
REDUCED by $3,450 (1.2%) on 06/30/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2020Monthly Fee: $17 Tax: $6,306 (2025)Community: Lucerne Park ReserveSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,306
Elementary School: Lake Alfred Elem
High School: Haines City Senior High
Tax Year: 2025
Middle School: Daniel Jenkins Academy of Technology Middle
Remarks: PRICE IMPROVEMENT! Motivated seller! Welcome to this super spacious 3-bedroom, 2-bath home located in Lucerne Park Reserve in Winter Haven. Built in 2020, this home offers a modern split floorplan, perfect for everyday living. The open layout creates a bright and airy feel throughout, with generous room sizes and excellent flow. Furniture is negotiable, making this a flexible move-in-ready opportunity for buyers. Enjoy outdoor living with an added screened-in patio/lanai overlooking a fully fenced backyard—ideal for pets, play, or relaxing in privacy. Situated in a well-maintained community featuring a pool, playground, and clubhouse, this home offers both comfort and convenience. Enjoy the benefits of newer construction paired with desirable neighborhood amenities, all just minutes from shopping, dining, and major roadways. A great opportunity to own a better than new home in a fantastic Winter Haven location.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Katherine Montana - De Jesus (863-508-3000)
1004 AVENUE G NE, WINTER HAVEN, FL 33881
$310,000736 Days on yellowkey MLS ID: P4931111
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1398 Built: 1954 Tax: $3,355 (2023)Community: Jarvis HeightsSingle Family
Taxes:$3,355
Elementary School: None
High School: None
Tax Year: 2023
Middle School: None
Remarks: Welcome to your dream home! This stunning three-bedroom, two-bathroom residence boasts beautiful ceramic tile flooring and luxurious vinyl throughout. The modern kitchen is a chef's delight, equipped with stainless steel appliances including a refrigerator, dishwasher, microwave, and range. Enjoy the spacious living room, perfect for entertaining, and an additional bonus room that offers versatile space to suit your needs. Cozy up by the fireplace on cooler evenings and create lasting memories. Located just seconds away from Polk State College, this home is ideal for investors or families alike. Plus, you're only an hour away from the magic of Disney and more attractions, and a mere 10 minutes from the fun at Legoland. For boating enthusiasts, there's a convenient boat ramp less than a quarter of a mile from the home. Don’t miss the opportunity to make this exceptional property yours!
Listing is courtesy of: STACEY TOWNS REALTY LLC (863-422-1585)
Listing Agent: Austin Towns (863-221-2586)
5352 NICKLAUS DR, WINTER HAVEN, FL 33884
$319,900104 Days on yellowkey MLS ID: L4960750
1 Days Off yellowkey (back on 6/1/2026)
REDUCED by $10,000 (3.0%) on 05/21/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2354 Built: 2007Monthly Fee: $5 Tax: $5,617 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$5,617
Remarks: RESORT-STYLE FLORIDA LIVING IN HIGHLY DESIRED LAKE ASHTON! Welcome to your own slice of paradise, where comfort meets connection in one of Central Florida’s most sought-after 55+ communities. This beautifully maintained home offers an easygoing, laid-back lifestyle with soaring ceilings that create an open, breezy feel the moment you walk in—perfect for relaxing or entertaining. At the heart of the home is a fully enclosed and expanded Florida Room, complete with dedicated AC vents, giving you year-round comfort whether you’re enjoying a quiet morning coffee or hosting friends after a day on the course. Thoughtful design continues throughout, including extra-tall closets that provide impressive storage space—keeping everything organized without sacrificing style. BIG-TICKET UPDATE: Enjoy peace of mind with a brand new roof installed on 4/6/2026—a major upgrade already taken care of, with the rest of the home in excellent condition. LIVE THE RESORT LIFE EVERY DAY: Step outside and experience everything that makes Lake Ashton so special: • Health & Wellness: State-of-the-art fitness center, indoor walking track, sauna, plus multiple heated indoor & outdoor pools and spas. • Endless Recreation: Private movie theater, bowling alley, billiards room, and a grand ballroom with live entertainment. • Championship Sports: Two 18-hole golf courses, along with pickleball, tennis, and bocce ball courts. • Dining & Social Scene: Golf cart to the Eagles Nest restaurant, explore 100+ social clubs, or enjoy direct access to Lake Ashton via the community boat ramp. • Peace of Mind: 24-hour manned security and a golf-cart-friendly community. Whether you’re looking for a full-time residence or the perfect seasonal escape, this home delivers the best of Florida living—relaxed, social, and full of opportunity. Homes in this highly desired community don’t last long. Contact your realtor today to schedule your private showing!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Wes Fleming (863-666-4136)
5850 CYPRESS GARDENS BLVD #302, WINTER HAVEN, FL 33884
$134,990109 Days on yellowkey MLS ID: P4938197
1 Days Off yellowkey (back on 6/30/2026)
REDUCED by $10 (0.0%) on 06/12/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1332 Built: 1975 Tax: $1,683 (2025)Community: Royal Crescent CondoCondo
Taxes:$1,683
Remarks: Welcome to this charming and updated, move-in ready 2-bedroom, 1.5-bath condo nestled right on Cypress Gardens Blvd in Winter Haven — just minutes from world-class shopping, dining, and the famous LEGOLAND Florida Resort! This well-maintained two-story unit has been tastefully updated throughout. Rich dark luxury vinyl plank flooring flows through the spacious living areas, giving the home a modern, cohesive feel. The kitchen is fully equipped with rich wood cabinetry, stainless steel appliances including a dishwasher, range, and refrigerator, and tile flooring — with a sliding glass door that brings in great natural light. A convenient half bath on the main level is fully updated with a new vanity and brushed nickel fixtures. Upstairs you'll find two generously sized bedrooms. The dedicated laundry closet plumbed and ready for your washer and dryer is on the first floor. The classic brick exterior and covered front porch add great curb appeal and a welcoming first impression. Whether you're a first-time buyer, downsizer, or investor looking for a rental in a high-demand location, this one checks all the boxes. Schedule your showing today — this one won't last!
Listing is courtesy of: HAVEN REALTY & INVESTMENTS (863-333-5053)
Listing Agent: Vincent Reina (863-398-6243)
1688 TEAGAN LN, WINTER HAVEN, FL 33884
$275,00049 Days on yellowkey MLS ID: TB8509963
REDUCED by $10,000 (3.5%) on 06/30/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1432 Built: 2024Monthly Fee: $17 Tax: $6,703 (2025)Community: Peace Creek ReserveSingle Family
Taxes:$6,703
Elementary School: South Pointe Elementary
High School: Mclaughlin Academy Of Excellence
Middle School: McLaughlin Academy Of Excellence
Remarks: Welcome to easy Florida living in the sought-after community of Peace Creek Reserve in Winter Haven! Built in 2024, this beautifully designed 3-bedroom home offers a modern split-bedroom layout, stylish finishes, and comfortable open living spaces perfect for both relaxing and entertaining. Step inside to discover bright and airy living areas with durable tile flooring flowing throughout the main spaces. The stunning kitchen is the heart of the home, featuring sleek stainless steel appliances, a large center island with seating space, abundant cabinetry, and an open design that overlooks both the dining area and spacious living room—making it easy to stay connected while hosting family and friends. Tucked away at the back of the home for added privacy, the primary suite offers a peaceful retreat with a generously sized bedroom, private ensuite bath with dual sink vanity, and a custom walk-in closet designed for organization and convenience. The split floor plan places the additional bedrooms and secondary bath on the opposite side of the home, creating flexibility for guests, family members, or a home office setup. Thoughtfully designed with newer construction benefits in mind, this home offers modern efficiency, low-maintenance living, and the peace of mind that comes with a recently built home. Peace Creek Reserve offers a convenient Winter Haven location close to shopping, dining, parks, lakes, and everyday essentials, while also providing easy access for commuting throughout Central Florida. Enjoy nearby outdoor recreation, local attractions, and all the charm that Winter Haven living has to offer. Whether you are looking for your first home, downsizing, or simply ready for a newer home with modern style and functionality, this one is ready to welcome you home. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Tony Baroni (866-863-9005)
120 4TH WAHNETA ST E, WINTER HAVEN, FL 33880
$150,000119 Days on yellowkey MLS ID: B4902213
0 Days Off yellowkey (back on 3/25/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 864 Built: 1956 Tax: $809 (2025)Community: Wahneta FarmsSingle Family
Taxes:$809
Remarks: Under contract-accepting backup offers. Step inside through the large enclosed foyer—perfect as a welcoming entryway, mudroom, or additional sitting space. The home features a comfortable living room and a well-appointed kitchen with a separate dining area, ideal for everyday living and entertaining. A bonus back room provides flexibility and can easily be used as a home office, hobby room, or additional living space. Enjoy outdoor living on the covered back porch overlooking a fully fenced yard—perfect for pets, gatherings, or simply relaxing in your own private oasis. The property is a true gem for those who love fresh fruit, featuring numerous mature trees including mango, avocado, peach, lemon, and other citrus varieties. Additional highlights include two large storage sheds with electricity already in place, offering excellent space for a workshop, storage, or creative projects. There is also a full RV hookup with electric, water, and septic—perfect for travelers or accommodating guests. This property offers a rare combination of comfort, utility, and outdoor enjoyment. Don’t miss this opportunity to own a home with so much to offer!
Listing is courtesy of: LAND SOUTH REALTY, LLC (863-937-8867)
Listing Agent: Ron Denney (863-660-3919)
610 AVENUE A NE, WINTER HAVEN, FL 33881
$215,000160 Days on yellowkey MLS ID: O6379847
0 Days Off yellowkey (back on 5/29/2026)
REDUCED by $4,900 (2.2%) on 05/07/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1512 Built: 1910 Tax: $3,038 (2025)Community: Revised Map Of Fernwood AddSingle Family
Taxes:$3,038
Remarks: Under contract-accepting backup offers. Price Reduced. Excellent Investment Opportunity. Zoning MX district. Seller Motivated. Recived $10,000 toward buyers closing cost. Charming Colonial Home — Elegantly Renovated in Central Winter Haven. Welcome to timeless charm blended with modern comfort in this beautifully Colonial residence, perfectly situated in the heart of Winter Haven, Florida. Meticulously updated while honoring its historic character, this home offers the ideal blend of classic architectural details and contemporary living. As you approach, you’re greeted by a stately façade showcasing symmetrical Colonial proportions, a welcoming front porch, and original period craftsmanship that has stood the test of time. Current zoning classification is MX (Mixed-Use), which allows a wide range of commercial and residential uses. Typical permitted uses examples are: Professional and medical offices, Assisted living facilities, ALF) / senior care, Group homes and supportive housing, Multifamily residential buildings, Live/work units and mixed commercial-residential developments.
Listing is courtesy of: CENTRAL REALTY GROUP AND PROPERTIES (407-582-9011)
Listing Agent: Raul Briceno (407-715-2550)
1646 TRESSEL CT, WINTER HAVEN, FL 33881
$280,00089 Days on yellowkey MLS ID: P4938246
REDUCED by $10,000 (3.4%) on 06/30/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1846 Built: 2020Monthly Fee: $50 Tax: $4,864 (2025)Community: Buckeye TraceSingle Family
Taxes:$4,864
Remarks: PRICE DROP!! Nestled within a secure, gated community with impressively low HOA fees, this beautiful 4-bedroom, 2-bathroom home offers true peace of mind. The highly versatile layout easily adapts to your lifestyle, whether you need extra space for a growing family, a dedicated home office, or a welcoming guest suite. Beyond the front door, you're just minutes from top-rated schools, medical services, and daily conveniences like Publix. Spend your weekends exploring the vibrant dining and nightlife of Downtown Winter Haven or making memories at nearby Legoland. More than just a house, this property is an extraordinary opportunity to secure a lifestyle of comfort and convenience. Schedule your tour today before it slips away!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Twanna Dewdney (863-207-1634)
2642 RUTLEDGE CT, WINTER HAVEN, FL 33884
$179,900106 Days on yellowkey MLS ID: A4688023
2 Days Off yellowkey (back on 6/30/2026)
REDUCED by $10,000 (5.3%) on 06/01/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1419 Built: 2006 Tax: $1,794 (2024)Community: Traditions Ph 01Townhouse
Taxes:$1,794
Elementary School: Chain O Lakes Elem
Tax Year: 2024
Remarks: Light and bright 2/2/1 in The Verandah's at Lake Reeves. The Verandahs offers a community pool and fishing dock on Lake Reeves. The low HOA fee includes ground maintenance, basic cable and internet, exterior painting and more. Easy access to shopping, Legoland, chain of lakes. Light and bright, move in ready. Dual master bedroom set up. Den/office off of main living area. Vaulted ceilings, large kitchen, open living plan.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
2786 ADELINE AVE, WINTER HAVEN, FL 33881
$289,900118 Days on yellowkey MLS ID: O6391683
REDUCED by $4,000 (1.4%) on 06/10/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1498 Built: 2026Monthly Fee: $8 Tax: $3,456 (2025)Community: Willowbrook SouthSingle Family
Taxes:$3,456
Elementary School: Elbert Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: Under Construction. Located in the heart of Winter Haven, Willowbrook South puts you close to the area's Chain of Lakes, beautiful parks, and an array of dining and shopping. With top attractions and everyday conveniences just minutes away, your new home here keeps you connected to everything you love. Your new home at Willowbrook South places you right where you want to be. Now let me Introduce you to the Freeport II this 1498 sqft, 4 Bedroom 2 Bath home is just to die for. This home provides Luxury Vinyl tile in all the wet areas and Great room and Quartz Counter tops in the Kitchen and both Bathrooms. The Kitchen includes a Stove, Microwave, Dishwasher and Refrigerator, all Stainless Steel by Whirlpool and the laundry room also includes a Washer and Dryer. With 2 Spare Bedrooms in the Front one in the Middle and an Owners Suite in the Back. The Owners Suite can easily fit a King size bed and has a large Walk-in closet. It also includes a Home Smart System. Come by today! *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Paul King (407-519-3940)
1797 HUMMINGBIRD RD, WINTER HAVEN, FL 33884
$476,99034 Days on yellowkey MLS ID: O6415738
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2787 Built: 2026Monthly Fee: $30 Tax: $2,606 (2025)Community: Harmony On Lake Eloise Phase 4Single Family
Taxes:$2,606
Elementary School: John Snively Elem
High School: Lake Region High
Remarks: Under Construction. Harmony at Lake Eloise presents The Camden, available to build in Winter Haven, FL. This all-concrete block constructed, one-story multi-gen layout offers two homes under one roof. As you enter the foyer you are greeted with two guest bedrooms that share an en suite bathroom with a double vanity. Making your way down the hall you will find a large dining room perfect for the whole family. The well-appointed kitchen overlooks the great room and features an island with bar seating, beautiful granite countertops and stainless steel appliances. Enjoy views of the oversized covered lanai from the café area just off the kitchen. Bedroom one, located at the back of the house for privacy, has an en suite bathroom with a double vanity and two spacious walk-in closets providing ample space for storage. This floorplan offers more than just a spare guest room. It’s two homes — the main home area with a separate suite including living space, bedroom, kitchenette and private entrances with the convenience and safety of a connecting door. Like all homes in Harmony at Lake Eloise, the Camden includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of the exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability, and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
2216 STARBOARD, WINTER HAVEN, FL 33881
$215,00015 Days on yellowkey MLS ID: TB8524293
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1549 Built: 1974Monthly Fee: $140 Tax: $2,780 (2025)Community: Hartridge LandingSpa: NoSingle Family
Taxes:$2,780
Elementary School: Walter Caldwell Elem
High School: Auburndale High School
Middle School: Westwood Middle
Remarks: Check out this wonderful opportunity to own a spacious 3-bedroom, 2.5-bath home in the desirable 55+ community of Hartridge Landings! This well-maintained community offers a low HOA fee that includes access to the community pool and a private boat ramp on Lake Hartridge, providing access to Winter Haven's renowned Chain of Lakes. Step inside to an open and versatile floor plan featuring two expansive living areas that have endless possibilities for entertaining, relaxing, or creating a dedicated den, formal living room, or family room. The spacious first-floor primary suite serves as a private retreat, complete with an en-suite bathroom featuring dual sinks and a walk-in shower. The galley-style kitchen is conveniently located just off the dining area and offers the perfect space for a cozy breakfast nook. Also on the first floor are a half bath, a generously sized laundry room with built-in shelving, and a flexible office/bonus room with a built-in desk. Both the kitchen and office provide direct access to the private courtyard, creating a great space for outdoor relaxation or entertaining. Upstairs, you'll find two generously sized guest bedrooms and a full bathroom, providing plenty of space for family and visitors. Conveniently located near shopping, dining, medical facilities, and everyday conveniences, this home offers the perfect combination of comfort, functionality, and low-maintenance living. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)
Listing Agent: Bree Allison (863-207-8595)
113 AVENUE C SE, WINTER HAVEN, FL 33880
$329,90015 Days on yellowkey MLS ID: O6420854
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1392 Built: 1950 Tax: $2,262 (2025)Community: Haven TerraceApartment
Taxes:$2,262
Remarks: INVESTOR OPPORTUNITY, HOUSE HACK DREAM, OR MULTI-GENERATIONAL LIVING! Welcome to 113 Avenue C SE, Winter Haven, FL, a beautifully maintained and FULLY FURNISHED income-producing property offering exceptional flexibility and value! Situated on a single parcel, this unique property features a charming 3 BEDROOM, 1 BATH main home currently operating as a successful AIRBNB, along with a DETACHED 1 BEDROOM, 1 BATH IN-LAW SUITE with its own private entrance, separate address (258 1st St S, Winter Haven, FL 33880), and alley access, currently rented for $1,100 /MONTH. Both units have been UPDATED, with ROOFS AND A/C SYSTEMS REPLACED WITHIN THE LAST 3 YEARS, allowing peace of mind for years to come. The front home showcases beautiful ORIGINAL HARDWOOD FLOORS, while the rear apartment features attractive WOOD-LOOK TILE flooring. Built in 1950, this property has been exceptionally cared for and is in GREAT CONDITION while maintaining its timeless character. Whether you're looking to HOUSE HACK, generate immediate RENTAL INCOME, accommodate extended family, or expand your investment portfolio, this property checks every box. Located just a SHORT WALK TO DOWNTOWN WINTER HAVEN, you'll enjoy local restaurants, breweries, coffee shops, farmers markets, and year-round community events. Winter Haven continues to experience tremendous growth with ongoing DOWNTOWN REDEVELOPMENT, major investments in public amenities and infrastructure, expanding logistics and employment opportunities through the Central Florida Integrated Logistics Park, and continued economic development expected over the coming years. Conveniently located approximately 10 minutes from LEGOLAND Florida Resort, 45-60 minutes to Walt Disney World, 50-60 minutes to Orlando International Airport, and about 1 hour to Tampa International Airport, this location offers easy access to Central Florida's world-famous attractions while benefiting from Winter Haven's rapidly expanding job market, vibrant downtown, and outstanding quality of life. Whether you're an investor seeking multiple income streams or a homeowner looking for a property that helps pay for itself, this is a RARE opportunity you won't want to miss!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nomar Rosa (646-673-3900)
1642 TEAGAN LN, WINTER HAVEN, FL 33884
$329,90015 Days on yellowkey MLS ID: O6420842
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1896 Built: 2024Monthly Fee: $78 Tax: $4,325 (2025)Community: Peace Crk ReserveSingle Family
Taxes:$4,325
Elementary School: Wahneta Elem
Remarks: Welcome to 1642 Teagan Lane, a charming 2 Story house located in Winterhaven, FL 33884. This newly constructed property presents a wonderful opportunity to enjoy comfortable living in a well-situated location. The house boasts a classic design with a welcoming exterior and a spacious layout that caters to a variety of needs. As you approach, you'll notice the well-maintained facade that adds to its curb appeal. Inside, the house provides ample space for living, dining, and entertaining. The property's layout is designed to maximize functionality while providing a cozy and inviting atmosphere. Large windows allow natural light to fill the rooms, creating a bright and airy ambiance throughout. Whether you're looking to relax or host guests, this house provides a versatile setting for any occasion. The outdoor area provides additional space for leisure and recreation, making it a superb complement to the indoor living areas. With its convenient location and appealing features, 1642 Teagan Lane is a wonderful place to call home.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
501 AVENUE G SE, WINTER HAVEN, FL 33880
$319,90015 Days on yellowkey MLS ID: O6420791
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1816 Built: 1955 Tax: $3,610 (2025)Community: Fanning SubApartment
Taxes:$3,610
Remarks: Welcome to an exceptional HOUSE HACKING and INVESTMENT OPPORTUNITY in the heart of Winter Haven! Legally classified as a SINGLE-FAMILY HOME, this unique property is GRANDFATHERED FOR MULTI-FAMILY USE and is currently configured as two separate living units, making it ideal for INVESTORS, OWNER-OCCUPANTS, or MULTI-GENERATIONAL LIVING. The front unit features 3 BEDROOMS, 1 BATHROOM, its own PRIVATE CARPORT, LAUNDRY ROOM, separate entrance, and private backyard, while the rear unit offers 1 BEDROOM, 1 BATHROOM, a private entrance, private backyard, and is currently rented for OVER $1,200 /MONTH. For added comfort, energy efficiency, and long-term value, the rear unit has been upgraded with a NEW MINI-SPLIT A/C SYSTEM, providing efficient climate control for tenants. The front unit has an estimated rental value of $1,650-$1,750 /MONTH, creating a projected combined rental income of approximately $2,850-$3,000+ /MONTH. Looking for additional upside? One of the bedrooms in the front unit has its OWN EXTERIOR ENTRANCE leading to the patio and offers exciting VALUE-ADD POTENTIAL for a future studio or efficiency conversion by adding a bathroom and kitchenette (buyer to verify all permitting, zoning, and city requirements). Recent 2023 UPDATES include updated kitchen countertops, fresh exterior paint, new flooring and interior paint in the rear unit, along with the installation of the NEW MINI-SPLIT A/C, making this property truly move-in and rent-ready. The home is serviced by ONE WATER METER and TWO SEPARATE ELECTRICAL METERS, allowing each unit to maintain its own electrical service. Perfectly situated just minutes from DOWNTOWN WINTER HAVEN, the famous Chain of Lakes, shopping, dining, healthcare, and schools, you'll also enjoy convenient access to US-27, I-4, Orlando International Airport, Downtown Orlando, and Walt Disney World, along with many of Central Florida's top attractions. As Winter Haven continues to experience significant residential, commercial, and economic growth, this property presents an outstanding opportunity to capitalize on both IMMEDIATE CASH FLOW and LONG-TERM APPRECIATION, whether you're looking to LIVE IN ONE UNIT WHILE RENTING THE OTHER, expand your investment portfolio, or own a versatile income-producing property with exceptional future potential. For added flexibility, the front 3-bedroom unit is also being offered FOR RENT, creating additional options for investors or future owner-occupants. Front Unit was Virtually Staged.
1100 MARTINIQUE DR #208, WINTER HAVEN, FL 33884
$94,75039 Days on yellowkey MLS ID: L4962463
0 Days Off yellowkey (back on 6/24/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1024 Built: 1974Monthly Fee: $313 Tax: $1,085 (2025)Community: Orchid Spgs Vill 300 BarcelonaCondo
Taxes:$1,085
Remarks: Under contract-accepting backup offers. Spacious 2-bedroom, 2-bath upper corner condo in the Barcelona Building of Orchid Springs, an all-ages community. This desirable end unit offers natural light and views from three sides, plus added privacy with minimal foot traffic. Recent updates include luxury vinyl plank flooring throughout, smooth ceilings, and neutral zero-VOC paint. Routine annual A/C maintenance completed in May 2026. The updated kitchen features 17 cabinets, 10 drawers, and a pantry, while the spacious primary suite offers a walk-in closet and en-suite bath. Assigned parking is located just below the unit. The monthly HOA fee of $312.69 covers exterior maintenance, grounds care, water, sewer, trash, gas service, pest control, common laundry facilities, and capital reserves. Conveniently located near LEGOLAND Florida and between Orlando and Tampa, with easy access to Winter Haven's renowned Chain of Lakes.
Listing Agent: Melissa Witter (863-206-8744)
1061 SAWGRASS DR, WINTER HAVEN, FL 33884
$449,90017 Days on yellowkey MLS ID: L4963110
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2069 Built: 2018Monthly Fee: $5 Tax: $4,851 (2025)Community: Lake Ashton West Ph 2 SouthSingle Family
Taxes:$4,851
Remarks: WELCOME to the lifestyle you've been dreaming of in the premier 55+ community of Lake Ashton! This Stunning Designer residence offers the perfect blend of elegance, comfort, and resort-style living with 3 spacious bedrooms, 2 beautifully appointed baths, plus a private den/office in a desirable split-bedroom floor plan. The heart of the home is the spectacular open-concept kitchen, featuring upgraded all-wood raised-panel cabinetry, gleaming granite countertops, stainless steel appliances, abundant storage, and a large breakfast bar overlooking the expansive living and dining areas. Gorgeous tile flooring flows throughout the main living spaces, while plush carpeting adds warmth and comfort to the bedrooms. Natural light fills every room through an abundance of windows, creating a bright and inviting atmosphere. Step through the sliding glass doors onto the screened veranda, where you can relax with your morning coffee or evening cocktail while enjoying peaceful pond views and Florida's beautiful sunsets. The luxurious owner's suite is a private retreat featuring an incredible spa-inspired bath with dual granite vanities, upgraded wood cabinetry, and a spectacular walk-through fully tiled shower designed for both beauty and convenience. Enjoy the pocket doors throughout the house. This house has so many Designer Upgrades, its difficult to list all of them. Life at Lake Ashton is second to none, offering two private golf courses, three pristine natural lakes, two magnificent clubhouses, indoor and outdoor resort-style swimming pools (including a relaxing hot tub), two state-of-the-art fitness centers, racquetball, basketball, tennis, pickleball, scenic walking trails winding throughout the golf course, and the convenience of a golf cart-friendly community. Enjoy dining at the restaurant overlooking the golf course, meet friends for endless social activities and entertainment, and experience the vibrant, active lifestyle you've always imagined. This home has solar panels that will save on your electric bills for years to come. Don't miss this exceptional opportunity to own one of Lake Ashton's most BEAUTIFUL DESIGNER HOMES. Schedule your private showing today and be the first to call this extraordinary residence HOME!
Listing is courtesy of: ROOST REALTY GROUP LLC (863-398-0267)
Listing Agent: Barb Wiechmann (863-255-9130)
800 WARE AVE NE, WINTER HAVEN, FL 33881
$242,49989 Days on yellowkey MLS ID: O6399008
REDUCED by $500 (0.2%) on 06/29/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1000 Built: 2023 Tax: $1,293 (2025)Community: Swan Lake EstatesSingle Family
Taxes:$1,293
Remarks: EXCELLENT INVESTMENT OPPORTUNITY! Welcome to 800 Ware Ave NE, Winter Haven, where immediate rental income meets exceptional long-term potential! TENANT OCCUPIED with a reliable, long-term tenant already in place through January 2027, this EXCELLENT INVESTMENT offers the perfect addition to your portfolio while giving you the flexibility to make it your future home. This newer 3-bedroom, 2-bathroom residence welcomes you with a bright, open-concept floor plan designed for both everyday comfort and effortless entertaining. Durable laminate flooring flows throughout the home, creating a modern, low-maintenance living space, while the spacious kitchen overlooks the living and dining areas so everyone stays connected, whether you're hosting family and friends or enjoying a quiet evening at home. Natural light fills the interior, creating a warm and inviting atmosphere you'll love coming home to. Step outside to the fully fenced backyard, where you can envision children and pets playing freely, weekend barbecues with friends, gardening, or simply relaxing with your morning coffee or evening drink in your own private outdoor retreat. Situated on a spacious corner lot, the home offers additional yard space, enhanced privacy, and wonderful curb appeal. Beyond the home itself, you'll enjoy everything that makes Winter Haven one of Central Florida's fastest-growing communities. Located just minutes from Downtown Winter Haven and the beautiful Chain of Lakes, you'll have endless opportunities for boating, fishing, waterfront dining, parks, festivals, and year-round outdoor recreation. Everyday conveniences are all within easy reach, including Publix, Polk State College, Winter Haven Hospital, local medical offices, banks, fitness centers, and a wide variety of popular restaurants, coffee shops, and shopping destinations. Catch the latest blockbuster at the nearby movie theater, spend the day at LEGOLAND Florida Resort, or enjoy convenient access to Lakeland, Davenport, and Orlando for even more entertainment and employment opportunities. The home is approximately 15 minutes from LEGOLAND Florida Resort, 25 minutes to Lakeland, 30 minutes to Posner Park in Davenport, 45 minutes to Walt Disney World, and about one hour to both Orlando and Tampa, making commuting and weekend adventures incredibly convenient. With continued residential and commercial growth throughout Winter Haven, demand for housing continues to remain strong, making this an outstanding opportunity for investors and future homeowners alike. Whether you're looking for immediate cash flow, long-term appreciation, or a place to call home in the future, this EXCELLENT INVESTMENT OPPORTUNITY offers the ideal combination of location, lifestyle, and lasting value. Schedule your private showing today and discover everything 800 Ware Ave NE has to offer!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Veronica Figueroa (407-519-3980)
441 SAN JOSE DR, WINTER HAVEN, FL 33884
$275,000431 Days on yellowkey MLS ID: P4934776
REDUCED by $10,000 (3.5%) on 04/14/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1843 Built: 1984Monthly Fee: $5 Tax: $1,000 (2024)Community: Orchid Springs Patio HomesSpa: NoSingle Family
Taxes:$1,000
Remarks: NEW ROOF 6/2026. Welcome to this exceptional 2-bedroom, 2-bathroom patio home nestled within the highly sought after Orchid Springs community. Positioned on an expansive double lot, this residence offers a serene & secluded wooded vista visible from the open kitchen and the generously proportioned screened patio. Noteworthy exterior features; Paved drive and walkways, attractive canopies and covered front porch invites you inside to discover a charming home. The kitchen boasts custom pantry space, ample counter area & is thoughtfully designed for hosting guests without compromising meal preparation. Beyond the kitchen, the spacious living room, flex apace is adjacent to a second private patio. The large family room offers expansive sliding doors and windows making the perfect space for relaxation. Leading to a beautiful lanai ideal for sharing a glass of wine or enjoying a barbeque, with its scenic outlook. The dining room is designed for casual or formal entertainment. The master bedroom features an ensuite bath and picturesque views while additional bedrooms and guest bathroom complete the layout. Flooring; Tiled foyer, kitchen and bathrooms with plush carpet in the master bedroom as well as the second bedroom, living and dining rooms. Designed with single level living in mind this Orchid Springs Patio Home offers ease of mobility and low maintenance. Stop outside to the spacious outdoor area enveloped by lush trees providing privacy and a natural ambiance. Additional amenities include a spacious 2 car garage with natural gas water heater & washer & dryer. Roof will be replaced before closing. Conveniently located in SE Winter Haven, this central Florida home provides easy access to downtown, Chain of Lakes boat launches, LegoLand, and major highways. The neighborhood also features a community clubhouse and pool, enhancing the overall Florida lifestyle experience.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
1026 MEDINAH DR, WINTER HAVEN, FL 33884
$177,50039 Days on yellowkey MLS ID: L4962495
REDUCED by $7,500 (4.1%) on 06/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1398 Built: 1980Monthly Fee: $334 Tax: $2,740 (2025)Community: Cypresswood Villas/GreenVilla
Taxes:$2,740
Remarks: Enjoy the Florida Country Club Lifestyle in this affordable and updated 2 bedroom 2 bath villa. Recent updates include new luxury vinyl flooring, new dishwasher and new microwave. MOVE IN CONDITION. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steven Smith, Pa (863-224-2297)
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