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Downtown Winter Haven 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
  • /32

    $674,900

    • 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
  • /14

    $975,000

    • 12 Beds
    • 12 Baths
    • 5,256 Sq Ft

    510 Avenue K NW, Winter Haven, FL 33881

    Turnkey 6-Unit Apartment Complex overlooking Lake Silver. FULLY occupied and exceptionally maintained 6-unit apartment building featuring updated and spacious 2 bed, 2 bath units. This property offers easy access to public transportation and is just minutes from downtown Winter Haven’s shops, restaurants, and entertainment. Winter Haven is the ski capital of the world! Tenants are able to sit on

    Kylie Berry BERRY REALTY & APPRAISAL SERVICES PA

    510 Avenue K NW, Winter Haven, FL 33881
  • /14

    $1,750,000

    • 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
  • /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
  • /49

    $379,900

    • 6 Beds
    • 2 Baths
    • 2,090 Sq Ft

    213 Palmetto Ave NE, Winter Haven, FL 33881

    Prime Investment Opportunity: Fully Occupied Duplex in the Heart of Winter Haven **1031 TAX EXCHANGE Friendly!** **Bring all offers; the seller is open to negotiation!** Discover an exceptional investment opportunity with this fully occupied duplex, ideally located in the vibrant heart of Winter Haven. This prime property boasts two income-producing units, each featuring 3 bedrooms and 1

    Ramsey Lahham YOU FIRST REALTY AND ASSOC LLC

    213 Palmetto Ave NE, Winter Haven, FL 33881
  • /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
  • /37

    $299,000

    • 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
  • /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
  • /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
  • /35

    $483,900 New Construction

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

    306 Avenue P NW, Winter Haven, FL 33881

    Under Construction. 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 materials, this duplex boasts

    Amalia Lucena LA ROSA REALTY PRESTIGE

    306 Avenue P NW, Winter Haven, FL 33881

Why Live in Downtown Winter Haven

Downtown Winter Haven is a vibrant neighborhood known for its eclectic dining, cultural attractions, and lakefront recreation. The area boasts a burgeoning dining scene with notable restaurants like Nutwood, Arabellas, Adler’s, and The Smokin’ Ox, alongside new additions such as Bowen Yard and established eateries like Lucille’s American Café. For nightlife, residents can enjoy Social Cocktail Lounge, Grove Roots Brewing Co., and The Union Taproom. The neighborhood is also a cultural hub, featuring Theatre Winter Haven, the Historic Ritz Theatre, and Gram Parsons Derry Down. Annual events, including Taste of Winter Haven and Craft Beer Crawl, along with the weekly Winter Haven Farmers Market, add to the community's lively atmosphere. The neighborhood is surrounded by several lakes, including Lake Howard, May, Shipp, and Cannon, offering ample opportunities for boating, fishing, and water skiing. Parks like South Lake Howard Nature Park and Martin Luther King Park provide green spaces with walking trails and recreational facilities. Housing options range from traditional ranch-style and midcentury homes to contemporary custom homes in gated communities, with lakefront properties being the most expensive. The area is served by top-rated schools such as Chain of Lakes Collegiate High and Frank E. Brigham Academy. Downtown Winter Haven is safer than the national average and is well-connected via U.S. Highway 17, U.S. Highway 27, and Interstate 4, with Tampa and Orlando approximately 50 miles away. Local amenities include Walmart, Publix, Aldi, and Lowe’s, ensuring convenient access to essentials.

Home Trends in Downtown Winter Haven, FL

Housing Trends

Median Sale Price
$240,000
Median Single Family Sale Price
$255,000
Median Townhouse Sale Price
$343,000
Median 2 Bedroom Sale Price
$128,500
Median 1 Bedroom Sale Price
$100,000
Average Price Per Sq Ft
$165
Number of Homes for Sale
96
Last 12 months Home Sales
213
Months of Supply
5.40
Median List Price
$248,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
2%
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