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4-Bedroom Homes for Sale in Downtown Winter Haven

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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
  • /59

    $649,900

    • 4 Beds
    • 3 Baths
    • 2,633 Sq Ft

    333 Lake Otis Dr SE, Winter Haven, FL 33880

    Welcome to this beautifully renovated pool home offering modern luxury, privacy, and ultimate functionality all with no HOA restrictions! Situated on a spacious corner lot, this 3-bedroom, 3-bath residence includes a dedicated office perfect for working from home or a 4th guest room. Inside, you'll find a brand-new designer kitchen with premium cabinetry, solid countertops, and stainless-steel

    Colin Wells SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC

    333 Lake Otis Dr SE, Winter Haven, FL 33880
  • /84

    $535,000

    • 4 Beds
    • 4 Baths
    • 3,221 Sq Ft

    800 W Lake Elbert Dr NE, Winter Haven, FL 33881

    Historic Elegance with Modern Luxury – Built by Cypress Gardens’ Founder Dick Pope! Step into a piece of Winter Haven history with this stunning 4-bedroom, 4-bathroom home, originally built in 1935 by Dick Pope, founder of the famed Cypress Gardens. Overflowing with timeless character and meticulously blended with modern updates, this residence offers a rare opportunity to own a truly iconic

    Team Papin FLORIDA LUXURY REALTY INC

    800 W Lake Elbert Dr NE, Winter Haven, FL 33881
  • /62

    $849,900

    • 4 Beds
    • 3 Baths
    • 3,020 Sq Ft

    1 Brogden Ct SE, Winter Haven, FL 33880

    Custom-Built by Hulbert Homes! Known for their exceptional quality and craftsmanship, Hulbert Homes delivers again with this thoughtfully designed home. From the custom mahogany double doors to the luxury vinyl flooring throughout, every detail has been carefully considered. This 4-bedroom, 3-bath home is filled with natural light and features high ceilings, crown moulding, and a spacious

    Brian Stephens EXP REALTY LLC

    1 Brogden Ct SE, Winter Haven, FL 33880
  • /28

    $849,900

    • 4 Beds
    • 2.5 Baths
    • 2,844 Sq Ft

    1002 Lake Elbert Dr SE, Winter Haven, FL 33880

    LAKE/POOL HOME with 160' of Lake Elbert Frontage! This beautiful brick residence offers resort-style living right at your doorstep with a private sandy beach or if you’re an avid boater, look to build your own boat dock! Other days relax in the back yard within your screened area and enjoy your heated pool with attached spa (new heater and chlorinator in 2024). Inside, this 4-bedroom, 2.5-bath

    Kevin Giguere EPIQUE REALTY, INC.

    1002 Lake Elbert Dr SE, Winter Haven, FL 33880
  • /76

    $499,000

    • 4 Beds
    • 2 Baths
    • 3,198 Sq Ft

    934 Lake Elbert Dr SE, Winter Haven, FL 33880

    Welcome to a one-of-a-kind lakeside retreat in the heart of Winter Haven — a beautifully preserved 1926 residence set on over half an acre of direct lakefront property along the serene shores of Lake Elbert. With more than 3,100 square feet of versatile living space, this property blends historic charm with modern flexibility for multigenerational households, remote work, or

    Chris Renfro KELLER WILLIAMS REALTY SMART

    934 Lake Elbert Dr SE, Winter Haven, FL 33880
  • /37

    $389,000

    • 4 Beds
    • 2 Baths
    • 2,292 Sq Ft

    710 Avenue T SE, Winter Haven, FL 33880

    Welcome to this modernly updated Mid-Century home, perfectly blending timeless charm with contemporary comforts. This spacious residence offers 4 bedrooms and 2 bathrooms across 2,292 square feet of thoughtfully designed living space. Step inside to an open great room plan featuring stunning Terrazzo flooring that flows seamlessly throughout the main areas, creating a bright and inviting

    Dee Norris NEXTHOME NORRIS & COMPANY REALTY

    710 Avenue T SE, Winter Haven, FL 33880
  • /30

    $375,000

    • 4 Beds
    • 2 Baths
    • 2,080 Sq Ft

    145 Waterside Cir, Winter Haven, FL 33880

    GORGEOUS 4 BEDROOM 2 BATH HOME. GRANITE COUNTER TOPS THROUGHOUT THE KITCHEN AND BATHROOMS. STAINLESS STEEL APPLIANCES, WALK IN PANTRY. LARGE ISLAND IN THIS OPEN FLOOR PLAN HOME. CERAMIC TILE IN THE MAIN LIVING AREAS, CARPET IN THE BEDROOMS, IRRIGATION. BACK YARD IS FENCED, INSIDE LAUNDRY ROOM. NEW MICROWAVE AND DISHWASHER REPLACED JUST SIX MONTHS AGO. THIS HOME HAS A HUGE SCREENED LANAI,

    Gengar Nerehood BONJORN REAL ESTATE

    145 Waterside Cir, Winter Haven, FL 33880
  • /47

    $2,600,000

    • 4 Beds
    • 4.5 Baths
    • 5,178 Sq Ft

    950 N Lake Otis Dr SE, Winter Haven, FL 33880

    There was a time when homes were designed to last—and this is one of them. Designed by award-winning architect Gene Leedy, this south-facing lakefront residence embodies a legacy of modernism uniquely attuned to Florida’s landscape and climate. As a founding voice of the Sarasota School of Architecture, Leedy’s vision was ahead of its time, helping to shape a movement that left its mark on

    Ashley Marbet COMPASS FLORIDA LLC

    950 N Lake Otis Dr SE, Winter Haven, FL 33880
  • /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
  • /30

    $250,000

    • 4 Beds
    • 3 Baths
    • 1,733 Sq Ft

    536 Avenue G SE, Winter Haven, FL 33880

    Step into potential with this unique 4-bedroom, 3-bath home nestled in the heart of Winter Haven. Full of character and opportunity, this property is perfect for someone ready to renovate, restore, and reimagine.With a spacious layout, this home offers distinctive architectural details, multiple living areas, and endless flexibility to design the space of your dreams. Whether you’re envisioning

    Karen Corea Cuadra LPT REALTY, LLC

    536 Avenue G SE, Winter Haven, FL 33880
  • /3

    $280,000

    • 4 Beds
    • 2 Baths
    • 1,593 Sq Ft

    229 Avenue B NE, Winter Haven, FL 33881

    Charming 1925 Two-Story Home with Income PotentialDiscover the possibilities with this centrally located 1925 two-story home, offering excellent income-producing potential. Ideally situated near major roads, hospitals, and doctors' offices, this property provides convenience and accessibility.The home features a metal workshop, carport, mature landscaping, and fruit trees, all

    Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

    229 Avenue B NE, Winter Haven, FL 33881
  • /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
  • /61

    $355,000

    • 4 Beds
    • 2 Baths
    • 1,824 Sq Ft

    415 Avenue K NE, Winter Haven, FL 33881

    PRICE IMPROVEMENT! No HOA, no Flodd Zone, no CDD. NEW ROOF was installed in 2022. AC and HEATING are both ENERGY EFFICIENT and were installed on 2022. Kitchen was updated with new tiles. Stainless steel appliances. Solid wood floors throughout the living area, the house sits on an oversized lot (there is lot 8 & 9) set back from the road and plenty of space in the back for entertaining or

    Miulvis Kivelier KIVELIER REALTY GROUP LLC

    415 Avenue K NE, Winter Haven, FL 33881
  • /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

Home Trends in Downtown Winter Haven, FL

Housing Trends

Median Sale Price
$508,900
Median Single Family Sale Price
$489,900
Median Townhouse Sale Price
$508,900
Median 2 Bedroom Sale Price
$360,000
Median 1 Bedroom Sale Price
$259,900
Average Price Per Sq Ft
$272
Number of Homes for Sale
23
Last 12 months Home Sales
125
Months of Supply
2.20
Median List Price
$499,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
34%
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