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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
  • /57

    $219,500

    • 2 Beds
    • 2 Baths
    • 1,575 Sq Ft

    1531 Oakview Cir SE, Winter Haven, FL 33880

    Welcome to the well-maintained 55+ owner occupant community of Oakview located in beautiful Winter Haven, Florida. This is a two bedroom two bath tastefully furnished home. The split bedroom plan gives lots of privacy to guests or residents. The living/dining room combination is spacious and located right off the kitchen for ease of entertaining family and friends. There is a den at the rear

    Agent Photo

    Brenda J. Quinn

    QUINN & COMPANY REALTORS, LLC

    (863) 270-7869

    1531 Oakview Cir SE, Winter Haven, FL 33880
  • /53

    $240,000

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

    1573 Vienna Square Dr, Winter Haven, FL 33884

    VIOLA! It's the lovely Vienna Square Villa you've been waiting for. CLEAN, one owner home offers 2 bedrooms, 2 bathrooms, and an open floor plan. You'll feel the serenity of the neutral colors, and easy care tile floors throughout the entire home. The lovely kitchen sports stainless steel appliances, and natural wood cabinets with multiple drawers for all your cookware. There are 2 pantry closets

    Marti Sutton CENTURY 21 WATSON & MYERS REALTY

    1573 Vienna Square Dr, Winter Haven, FL 33884
  • /47

    $239,000

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft

    2244 Lucerne Park Rd, Winter Haven, FL 33881

    INCREDIBLE OPPORTUNITY to own a TURN-KEY, COMPLETELY RENOVATED DUPLEX in the heart of WINTER HAVEN, FLORIDA! This INCOME-PRODUCING PROPERTY features TWO 1-BEDROOM, 1-BATHROOM UNITS, each thoughtfully updated for MODERN COMFORT and LONG-TERM DURABILITY. Each unit includes its own PRIVATE DRIVEWAY, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES (2024), BRAND-NEW VINYL PLANK FLOORING, UPDATED

    Betsy Tinervin REAL BROKER, LLC

    2244 Lucerne Park Rd, Winter Haven, FL 33881
  • /23

    $899,000

    • 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

    $299,999

    • 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
  • /25

    $550,000

    • 6 Beds
    • 5 Baths
    • 3,569 Sq Ft

    631 Avenue H NW, Winter Haven, FL 33881

    Lake Howard Apartments is a a 5-unit multifamily property located in Winter Haven, Polk County, Florida. Built in 1920, this well-maintained property spans 3,569 square feet across 0.29 acres, offering residents an attractive living environment near Lake Howard.The property consists of four one-bedroom, one-bathroom units and one two-bedroom, one-bathroom unit. Constructed with wood frame

    Tito Urbano FLORIDA REALTY INVESTMENTS

    631 Avenue H NW, Winter Haven, FL 33881
  • /23

    $750,000

    • 11 Beds
    • 7 Baths
    • 4,518 Sq Ft

    662 24th St NW, Winter Haven, FL 33880

    Investor Special! Rare opportunity to acquire a 7-unit, duplex-style community offering excellent potential and cash-flow possibilities. The property features two duplex buildings, each consisting of two 2-bedroom, 1-bathroom units, plus one triplex building with three 1-bedroom, 1-bathroom units. All units require updating, providing an outstanding value-add opportunity to significantly increase

    Chris Renfro KELLER WILLIAMS REALTY SMART

    662 24th St NW, Winter Haven, FL 33880
  • /9

    $825,000

    • 10 Beds
    • 5 Baths
    • 3,667 Sq Ft

    1801 3rd Ct SE, Winter Haven, FL 33880

    FULLY RENOVATED 5-UNIT APARTMENT BUILDING JUST OFF CYPRESS GARDENS BLVD. IN SOUTHEAST WINTER HAVEN!!! NEW ROOF IN 2022, BUILDING FEATURES A COURTYARD PATIO & LAUNDRY FACILITY, INTERIOR FEATURES INCLUDE STAINLESS APPLIANCES, GRANITE COUNTER TOPS, LUXURY VINYL PLANK FLOORING (NO CARPET), FULLY EQUIPPED KITCHENS - IN ALL UNITS! WATER USAGE HAS A MONITORING SERVICE FOR BACK BILLING, POWER IS ON

    Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    1801 3rd Ct SE, Winter Haven, FL 33880
  • /63

    $340,000

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

    806 Avenue O SW, Winter Haven, FL 33880

    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 front porch and charm of this well-maintained property, currently rented for $1,550/month.

    Nancy Grabowski REDFIN CORPORATION

    806 Avenue O SW, Winter Haven, FL 33880
  • /12

    $325,000

    • 2 Beds
    • 1 Bath
    • 1,621 Sq Ft

    602 Avenue F NE, Winter Haven, FL 33881

    LAKEFRONT DUPLEX on gorgeous LAKE MARTHA. Prime Investment or Multi-Generational Living! Very Rare opportunity to own a lakefront duplex in the heart of Winter Haven, nestled on the shores of Lake Martha! This income-producing property features two identical 2BR/1BA units (except left side has a big garage), offering breathtaking water views, private entrances, and endless possibilities for

    Jack Keller JACK KELLER INC

    602 Avenue F NE, Winter Haven, FL 33881
  • /26

    $229,900 Open Sun 11AM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,430 Sq Ft

    2254 Firestone Place, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Welcome home to this spacious 2-bedroom/2-bathroom Golf Villa located in the highly-sought-after Cypresswood community of Winter Haven and enjoy nearly maintenance-free living. Renovations completed in recent years include newer luxury vinyl flooring, kitchen appliances, and a freshly painted interior. This single-story villa offers TWO outdoor

    Kayly Malinas JOHN WOOD REALTY, INC.

    2254 Firestone Place, Winter Haven, FL 33884
  • /37

    $310,000

    • 4 Beds
    • 3 Baths
    • 1,440 Sq Ft

    726 Avenue L SW, Winter Haven, FL 33880

    BACK ON MARKET: Buyer fell through, no fault of Seller or Property! Great duplex in Winter Haven! Bottom unit currently rented at $1475 (net) / month is a 2 bed 2 bath (both full) unit with laundry hookups and ramp accessibility from front of unit. Top unit is unoccupied, and is a 2 bed 1 bath (3/4) with staircase access from rear of home. Priced to perform, this is ready for its next investor!

    Ryan Sanders SELLSTATE CENTRIC REALTY

    726 Avenue L SW, Winter Haven, FL 33880
  • /12

    $219,000

    • 2 Beds
    • 2 Baths
    • 1,139 Sq Ft

    Unlisted Address

    Tenant in place.Tenant may stay or he can be asked to leave prior to closing.2 bedroom 2 bath villa in close proximity to the clubhouse, pool and tennis courts.Enjoy the Country club lifestyle in this affordable villa with an enclosed Florida room.

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    Unlisted Address
  • /76

    $495,000

    • 8 Beds
    • 4 Baths
    • 2,862 Sq Ft

    2435 Edwin St NE, Winter Haven, FL 33881

    Cash cow, very little maintenance.Every unit has own electric meter and central air and heat.Water bill is paid by owner $120 - 180 month.Roof replaced on 2018.One unit is completly renewed, other 3 units are partially renewed.Must see!

    Pedro Fernandez Salvador CONTEMPORARY REALTY GROUP

    2435 Edwin St NE, Winter Haven, FL 33881
  • /33

    $243,000

    • 2 Beds
    • 2 Baths
    • 1,521 Sq Ft

    2824 Attwater Loop, Winter Haven, FL 33884

    SELLER IS PAYING YOUR FIRST 6 MONTHS OF HOA FEES!!! Stunning Corner Villa with Den! Move-In Ready & Model Perfect! Welcome to this immaculate 2-bedroom, 2-bathroom corner villa with a versatile den/office, designed for modern living. Located in the sought after maintenance free living community of Traditions! Built in 2019, this home showcases quartz countertops, designer paint, and a combination

    Jackie Mazurowski KELLER WILLIAMS REALTY SMART 1

    2824 Attwater Loop, Winter Haven, FL 33884
  • /26

    $545,000

    • 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
  • /16

    $535,000

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

    231 Palmetto Ave NW, Winter Haven, FL 33881

    PRICE REDUCTION!!! Full Occupancy, $57,000 Annualized 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

    David Craig 1513 REALTY LLC

    231 Palmetto Ave NW, Winter Haven, FL 33881
  • /40

    $229,000

    • 2 Beds
    • 2 Baths
    • 1,521 Sq Ft

    3020 Caneel St, Winter Haven, FL 33884

    GREAT OPPORTUNITY!!! PRICE IMPROVEMENT!!! Totally TURNKEY with all NEW FURNISHINGS!!! Welcome to carefree living in this bright and airy super clean villa. 1521 sq. ft. with 2 bedrooms, 2 bathrooms and a flex room for den, guests or office. The modern kitchen boasts tall cabinets with crown molding, quartz countertops and smudge proof stainless appliances and a pantry. Ceilings are high

    Vicky Holloway LEGACY REAL ESTATE CENTER INC

    3020 Caneel St, Winter Haven, FL 33884
  • /44

    $232,000

    • 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

    • 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

    $234,900

    • 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
  • /15

    $229,900

    • 2 Beds
    • 2 Baths
    • 1,240 Sq Ft

    625 Avenue B SW, Winter Haven, FL 33880

    Looking for an investment opportunity look no further! This duplex is nestled in the heart of Winter Haven just minutes from downtown. Both units are fully occupied. Each unit is 1 bedroom and 1 bathroom and are both nearly 700 living sq. ft. With monthly rents totaling $1,950.00 and an annual gross income of $23,400.00. So call today to get in on the action before this amazing opportunity slips

    Matt Mesimer KELLER WILLIAMS REALTY SMART 1

    625 Avenue B SW, Winter Haven, FL 33880
  • /51

    $230,000 New Construction

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

    2885 Attwater Loop, Winter Haven, FL 33884

    Prime LOCATION in Traditions – A Premier 55+ CommunityDiscover the perfect blend of comfort and convenience in this charming 2-bedroom, 2-bathroom villa with a versatile Flex Room, ideal for a home office, quiet retreat, or formal dining space. This smart home is designed for modern living, featuring a work-efficient kitchen with elegant white cabinets, crown molding, brushed nickel hardware,

    Michelle Urena EXP REALTY LLC

    2885 Attwater Loop, Winter Haven, FL 33884
  • /11

    $484,900 New Construction

    • 4 Beds
    • 4 Baths
    • 2,804 Sq Ft

    306 Avenue P NW, Winter Haven, FL 33881

    Under Construction. More updated pictures coming soon! This newly constructed **2025 duplex** presents an incredible **investment opportunity** in the heart of **Winter Haven**, just minutes from world-famous theme parks. Each unit features a **spacious, modern layout** with **2 bedrooms and 2 bathrooms**, offering comfort, style, and functionality for tenants or guests. Built with high-quality

    Amalia Lucena LA ROSA REALTY PRESTIGE

    306 Avenue P NW, Winter Haven, FL 33881

About 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 popular destination for snowbirds seeking a second home and empty-nesters relocating from up north, but a younger demographic is driving the current growth. Fitting for a city that offers year-round outdoor adventures, is home to Legoland theme park and has a buzzy downtown with a burgeoning contemporary ...

Home Trends in Winter Haven, FL

Home Trends

Median Price (12 Mo)
$289,990
Median Single Family Price
$296,987
Median Townhouse Price
$271,750
Median 2 Bedroom Price
$158,000
Median 1 Bedroom Price
$105,000
Average Price Per Sq Ft
$174
Number of Homes for Sale
893
Last 12 months Home Sales
1,914
Months of Supply
5.60
Median List Price
$305,000
Median Discount From 1st List Price
4%
Median Home Sale Price YoY Change
-3%
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