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Winter Haven, FL Multifamily Homes & Duplexes for Sale

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  • /62

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,416 Sq Ft

    577 6th St SE, Winter Haven, FL 33880

    TWO Income-Producing Properties, One Amazing Opportunity! This unique corner-lot package includes two CB 2-bedroom, 1-bath homes being sold together – ideal for investors, multi-generational living, or those looking to live in one and rent the other! Situated on a spacious 140x105 lot, Unit 577, boasts a brand-new roof, new HVAC system, and an all-new screened-in L-shaped lanai, that expands your

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 264-4920

    577 6th St SE, Winter Haven, FL 33880
  • /27

    $340,000

    • 7 Beds
    • 3 Baths
    • 2,056 Sq Ft

    806 Avenue O SW, Winter Haven, FL 33880

    "Bundled service pricing available for buyers. Connect with the listing agent for details." Investor's Dream! This income-generating triplex meets the investor 1% rent rule and offers instant cash flow with two units already rented! The front historic 1925 wood-frame home features 3 bedrooms, 1 bathroom, a spacious floor plan, a fully equipped kitchen, and inside laundry. Enjoy the large screened

    Nancy Grabowski REDFIN CORPORATION

    806 Avenue O SW, Winter Haven, FL 33880
  • /22

    $795,000

    • 5 Beds
    • 4 Baths
    • 2,800 Sq Ft

    Unlisted Address

    * Unique Investment or Multi-Generational Living Opportunity on the Winter Haven Chain of Lakes! *Set up as a Kosher Kitchen or can separate lower floor into 2 units.Looking for income potential, a spacious family retreat, or both? This versatile property offers two fully updated units on the main floor plus a private fully updated upstairs suite—perfect for a mother-in-law setup,

    Leslie Wichman EXP REALTY LLC

    Unlisted Address
  • /15

    $315,000

    • 4 Beds
    • 2 Baths
    • 1,488 Sq Ft

    3356 Avenue Q NW, Winter Haven, FL 33881

    Turnkey duplex generating immediate income from day one! Located at 3356 Avenue Q NW, this well-maintained property features two spacious 2-bed/1-bath units, both currently leased to reliable tenants. No vacancies, no renovations needed—just steady rental income.Situated in a quiet, established neighborhood, the property is surrounded by public schools within a 2-mile radius, making it

    Enrique Ojeda BANERSY REAL ESTATE, LLC

    3356 Avenue Q NW, Winter Haven, FL 33881
  • /18

    $425,000

    • 8 Beds
    • 5 Baths
    • 3,588 Sq Ft

    731 Avenue A SW, Winter Haven, FL 33880

    PLEASE SEE ATTACHED PROPERTY BROCHURE FOR MORE DETAILS. Beautiful historic home with two income producing units in the main home, and a third unit in the converted garage. Near picturesque Lake Howard, Winter Haven, this is an easy to manage money maker. 3,588 SF total, with 2,888 SF in the main home and 800 SF in the garage space. All tenants are on leases, with two of the three currently

    Craig Morby SAUNDERS REAL ESTATE, LLC

    731 Avenue A SW, Winter Haven, FL 33880
  • /39

    $280,000

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft

    2817 Wingfoot Ct, Winter Haven, FL 33884

    Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open

    Dee Norris NEXTHOME NORRIS & COMPANY REALTY

    2817 Wingfoot Ct, Winter Haven, FL 33884
  • /31

    $279,900

    • 2 Beds
    • 2 Baths
    • 1,368 Sq Ft

    14 Enclave Dr, Winter Haven, FL 33884

    Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven.The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    14 Enclave Dr, Winter Haven, FL 33884
  • /14

    $535,000

    • 8 Beds
    • 8 Baths
    • 3,456 Sq Ft

    231 Palmetto Ave NW, Winter Haven, FL 33881

    Full Occupancy, $57,000 Annual Gross Income, Long Term Leases in place. Turnkey QUADRUPLEX located close to downtown Winter Haven. Great opportunity to add to your portfolio or buy your first investment property. Each unit features 2 bedrooms, 1 full bathroom and 1 half bathroom, eat in kitchen, living room, a mix of tile and vinyl plank flooring, and laundry room equipped with washer and dryer

    David Craig 1513 REALTY LLC

    231 Palmetto Ave NW, Winter Haven, FL 33881
  • /32

    $659,900

    • 6 Baths
    • 2,400 Sq Ft

    351 Avenue North NE, Winter Haven, FL 33881

    **100 PERCENT OCCUPIED**Turnkey 6-unit studio apartment building on a corner lot in Winter Haven – 100% occupied and fully remodeled! All units have been upgraded with NEW INTERIOR PAINT, NEW APPLIANCES, NEW CABINETS, NEW COUNTERTOPS, NEW TRIM, NEW FLOORING, NEWER VINYL WINDOWS, NEW CEILING FANS, and MODERN LIGHT FIXTURES. Each unit features its own FRONT PORCH, IN-UNIT LAUNDRY WITH FRONT-LOADING

    Betsy Tinervin REAL BROKER, LLC

    351 Avenue North NE, Winter Haven, FL 33881
  • /38

    $240,000

    • 2 Beds
    • 2 Baths
    • 1,369 Sq Ft

    1218 Vienna Square Dr, Winter Haven, FL 33884

    **This property qualifies for a closing cost credit up to $3,600 through the Seller’s preferred lender plus an additional $1,000 credit for carpet from the Seller.** Welcome to a peaceful and sought-after 55+ community of Vienna Square, this beautifully maintained 2-bedroom, 2-bathroom villa with a 2-car garage offers low-maintenance living with touches of elegance throughout. As you approach,

    Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    1218 Vienna Square Dr, Winter Haven, FL 33884
  • /34

    $205,000

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft

    2282 Firestone Place, Winter Haven, FL 33884

    Welcome to Cypresswood Golf & Country Club Living!Discover this charming 2-bed, 2-bath, single-story Golf Villa at 2282 Firestone Pl in the exclusive gated community of Cypresswood in Winter Haven, FL. Boasting 1,164 sq ft of thoughtfully designed living space, this villa offers the perfect blend of comfort, style, and sweeping golf course views.Key Features & Upgrades:Two inviting

    Juan Yglesias KELLER WILLIAMS REALTY SMART 1

    2282 Firestone Place, Winter Haven, FL 33884
  • /46

    $234,900

    • 2 Beds
    • 2 Baths
    • 1,563 Sq Ft

    1077 Medinah Way, Winter Haven, FL 33884

    HARD TO FIND ...YET EASY TO OWN.!!! ENJOY COMING HOME TO THIS WONDERFUL COMMUNITY IN A TENNIS VILLA. IT IS A SPACIOUS END UNIT IN THE BEAUTIFUL CYPRESSWOOD GOLF AND TENNIS COMMUNITY WITH LOTS OF AMENITIES INCLUDING GATE SECURITY. CALL TO PREVIEW THIS WELL-MAINTAINED 2 BED 2 BATH CB VILLA, WITH FORMAL LIVING AND DINING AREA, SPACIOUS FLORIDA ROOM OVERLOOKING THE TENNIS COURTS AND POOL AREA, NICE

    Heidi Gravel WESTLAKE REAL ESTATE CO., INC.

    1077 Medinah Way, Winter Haven, FL 33884
  • /14

    $1,698,000

    • 20 Beds
    • 16 Baths
    • 10,620 Sq Ft

    669 Avenue B NW, Winter Haven, FL 33881

    Lucia Apartments is a unique historic 100 year old 16 unit apartment project with Lake Howard (624 acre lake) views near downtown Winter Haven, which is just east of Lakeland. The 16 units are across 3 parcels all next to each other plus an additional vacant parcel for extra parking. The 8 unit building was the original Winter Haven Hospital in 1925 and has since become studio/1bedroom

    Beau Beery BRG REALTY VENTURES

    669 Avenue B NW, Winter Haven, FL 33881
  • /46

    $264,900

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft

    13 Enclave Dr, Winter Haven, FL 33884

    Welcome to this maintained 3 bedroom, 2 bath one-story villa/townhouse located in Enclave, a quiet and desirable neighborhood within the gated golf community of Cypresswood Golf & Country Club. This spacious end-unit features a functional split-bedroom floor plan, generous living and dining areas, and an inviting Florida room that adds to the overall living space. The kitchen offers ample cabinet

    Suzanna Rudd KELLER WILLIAMS REALTY SMART 1

    13 Enclave Dr, Winter Haven, FL 33884
  • /8

    $360,000

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft

    2097 Avenue H NW, Winter Haven, FL 33881

    This duplex is perfect for Investors. Income is currently $2600 a month. The property is situated on a corner lot with two bedroom one bath in each duplex spanning 1,758 ft.2. The roof was replaced in 2022. This duplex is ready for some new ownership. The duplex is AS/IS The tenants have been there for over 3 years and are month-to-month right now at $1,3000 each unit.

    Marcy Smiley Theobald IRON VALLEY REAL ESTATE OSCEOL

    2097 Avenue H NW, Winter Haven, FL 33881
  • /20

    $269,000

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft

    2202 Garden Lake Dr, Winter Haven, FL 33884

    Welcome to beautiful southeast Winter Haven, home to the Chain of Lakes and Legoland! This spacious 3-bedroom, 2-bath home is in move-in ready condition, featuring a new water heater , a 4-year old a/c unit, and granite countertops in both the kitchen and bathrooms. Located in a desirable subdivision that boasts a community pool, clubhouse and 24 hour gated security, this home offers comfort,

    Stephen Hachey FLAT FEE MLS REALTY

    2202 Garden Lake Dr, Winter Haven, FL 33884
  • /23

    $899,000

    • 2 Beds
    • 2 Baths
    • 1,208 Sq Ft

    802 Avenue L SW, Winter Haven, FL 33880

    Rare lakefront development opportunity located in the Winter Haven Downtown CRA District. This 2.46-acre property offers beautiful views of Lake May and access to the Winter Haven Chain of Lakes. Current DOR use code (0852) permits duplexes, triplexes, and quadplexes — up to 9 units — in Polk City, Auburndale, Lake Alfred, and Winter Haven.The property includes a 1,208 sq ft concrete

    Veronica Bard LA ROSA REALTY PRESTIGE

    802 Avenue L SW, Winter Haven, FL 33880
  • /43

    $289,900

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    2220 Avenue F NW, Winter Haven, FL 33880

    Come see this duplex in the heart of Winter Haven. It’s minutes away from Winter Haven Hospital and LegoLand. This property offers a fantastic opportunity for savvy investors. Each unit features 2 bedrooms, 1 bathroom, and with enough space to make a 3rd bedroom. Both units have tile flooring throughout. Tenants are already in place so it would start cash flowing immediately. The backyard

    Rick Sein REALSOURCE PROPERTY MANGNT LLC

    2220 Avenue F NW, Winter Haven, FL 33880
  • /26

    $498,999

    • 4 Beds
    • 3 Baths
    • 1,985 Sq Ft

    1075 8th St NW, Winter Haven, FL 33881

    Income-Generating Property with Two In-Law Suites!! Maximize your rental income potential with this 4-bedroom, 3-bathroom property, featuring a 2-bedroom, 1-bathroom main house and two separate in-law suites, each with private entrances—perfect for long-term tenants, short-term rentals, or multi-generational living. The main house offers two spacious bedrooms, a full bathroom, and an inviting

    Karen Corea Cuadra LPT REALTY, LLC

    1075 8th St NW, Winter Haven, FL 33881
  • /44

    $227,000

    • 2 Beds
    • 2 Baths
    • 1,231 Sq Ft

    1561 Vienna Square Dr, Winter Haven, FL 33884

    R E D U C E D ... YOU'LL LOVE THIS MAINTENANCE FREE LIFESTYLE IN DESIREABLE VIENNA SQUARE , LOCATED IN WINTER HAVEN. THIS VILLA IS MOVE IN READY. THIS 2BR-2BA VILLA OFFERS AN OPEN GREAT ROOM DESIGN WITH SPLIT BEDROOMS. THE MASTER ENSUITE HAS WALK IN CLOSET WITH STEP IN SHOWER FOR CONVENIENCE. THE 2ND BEDROOM OFF FRONT ENTRANCE OF HOME HAS AN ADJOINING BATH WITH TUB AND SHOWER. DON'T WAIT,

    Glenda Pruitt FLORIDA HOME CHOICE REALTY

    1561 Vienna Square Dr, Winter Haven, FL 33884
  • /38

    $1,650,000

    • 8 Beds
    • 7 Baths
    • 5,194 Sq Ft

    1957 Rifle Range Rd, Winter Haven, FL 33880

    One or more photo(s) has been virtually staged. Nestled on 14 acres of serene land, this expansive property offers a rare combination of space, privacy, and convenience, with easy access to downtown Winter Haven and Legoland. The main residence features a spacious split floor plan with 3 bedrooms and 2 bathrooms. Vaulted ceilings and an open layout create an airy, inviting atmosphere, while the

    David Small KELLER WILLIAMS REALTY SMART 1

    1957 Rifle Range Rd, Winter Haven, FL 33880
  • /44

    $224,900

    • 2 Beds
    • 2 Baths
    • 1,278 Sq Ft

    1039 Medinah Dr, Winter Haven, FL 33884

    1 OWNER HOME!! Don't miss out on this 2 bed 2 bath tennis villa in the highly desired neighborhood of Cypresswood. The HOA takes care of the roof, lawn, paint, and exterior maintenance. Enjoy the security of living in a community with a 24 hour guard at the gate. There is plenty to do all within the community. There is a golf course, restaurant, community pool and tennis courts. The home has all

    Robert webb JOHN WEBB INC

    1039 Medinah Dr, Winter Haven, FL 33884
  • /89

    $695,000

    • 9 Beds
    • 4 Baths
    • 3,446 Sq Ft

    121 Bates Ave SE, Winter Haven, FL 33880

    This rare offering consists of three parcels with a mix of C-3 commercial and R-3 residential zoning, presenting an exceptional investment opportunity on 1st Street South in the heart of Winter Haven. Located on a bustling four-lane road with 30,000 cars passing daily, these properties provide unparalleled exposure for businesses. The first two parcels, located at 212 1st St S and 210 1st St S,

    Hank Petty KELLER WILLIAMS REALTY SMART 1

    121 Bates Ave SE, Winter Haven, FL 33880
  • /51

    $205,000 New Construction

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    2885 Attwater Loop, Winter Haven, FL 33884

    PRICED TO SELL – NOW THE LOWEST-PRICED HOME IN THE COMMUNITY!Motivated sellers have just reduced the price, making this beautiful villa in Traditions 55+ the best value in the neighborhood! This 2-bedroom, 2-bathroom home with a flex room (ideal for a home office, den, or dining space) offers both comfort and modern convenience.The smart home features a well-appointed kitchen with

    Michelle Urena REALTY OF AMERICA

    2885 Attwater Loop, Winter Haven, FL 33884

Why Live in Winter Haven

Winter Haven is the midpoint between Tampa and Orlando in rapidly growing Polk County. Known for having dozens of lakes, this outdoor paradise has experienced significant growth in recent years, reaching 60,000 in 2024. For years the city was a ...

Home Trends in Winter Haven, FL

Housing Trends

Median Sale Price
$285,949
Median Single Family Sale Price
$299,999
Median Townhouse Sale Price
$259,900
Median 2 Bedroom Sale Price
$139,400
Median 1 Bedroom Sale Price
$100,000
Average Price Per Sq Ft
$172
Number of Homes for Sale
868
Last 12 months Home Sales
1,889
Months of Supply
5.50
Median List Price
$309,990
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-4%
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