117

Downtown Winter Haven Homes for Sale

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  • /23

    $139,900

    • 3 Beds
    • 2 Baths
    • 1,114 Sq Ft

    333 Lake Howard Dr NW Unit 201, Winter Haven, FL 33880

    SCENIC VIEWS OF LAKE HOWARD! Enjoy lakefront living in the 55+ Imperial harbours community - Welcome to this 3 bedroom 2 bathroom home located in Winter Haven, Florida. Minutes from shopping, dining and entertainment. Nestled along side the chain of lakes! Sip your morning coffee overlooking scenic lakefront views of Lake Howard from the sunroom, spend weekends by the community pool, or launch

    Sarah Garner COLDWELL BANKER REALTY

    333 Lake Howard Dr NW Unit 201, Winter Haven, FL 33880
  • /34

    $199,000

    • 3 Beds
    • 1 Bath
    • 744 Sq Ft

    345 Avenue P NE Unit FVS, Winter Haven, FL 33881

    Priced to Sell! Newly remodeled 3 bedroom 1 bath home, brand new flooring throughout, new kitchen and bathroom! Close to Lake Maude, Lake Maude Nature Park and Winter Haven Hospital

    Leona Ujkic COLDWELL BANKER REALTY

    345 Avenue P NE Unit FVS, Winter Haven, FL 33881
  • /29

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    880 Oleander Dr SE, Winter Haven, FL 33880

    Welcome to this inviting 3 bedroom, 2 bath home with 1,860 sqft of living space in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious family room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a fireplace with built-in bookshelves, creating a warm and

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 591-6496

    880 Oleander Dr SE, Winter Haven, FL 33880
  • /28

    $110,000

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    333 Lake Howard Dr NW Unit 213D, Winter Haven, FL 33880

    A 55+ Active community well maintained surrounded by gorgeous landscaping, dock access to the Winter Haven's Chain of Lakes (LAKE HOWARD). This second floor unit offers a range of amenities that includes a recreational room, heated community pool, shuffleboard, and grills to BBQ by the beautiful gazebo, community boat ramp nearby fishing allowed. Check out this 2 bedroom, 2 bath condo with an

    Lisa Simpson KELLER WILLIAMS REALTY SMART 1

    333 Lake Howard Dr NW Unit 213D, Winter Haven, FL 33880
  • /7

    $49,999

    • Land
    • 0.21 Acre
    • $238,090 per Acre

    335 Avenue O NW, Winter Haven, FL 33881

    This as-is vacant lot in beautiful Winter Haven won't last long! Utilities on site, previous house burnt down. Surrounded by development and located just minutes from lakes, shopping, and schools, and a new Rec Center. Act fast—deals like this don't stick around!

    Steven Koleno BEYCOME OF FLORIDA LLC

    335 Avenue O NW, Winter Haven, FL 33881
  • /25

    $462,000 New Construction

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

    306 Avenue P NW, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Brand-New 2025 Duplex – An exceptional investment opportunity in the thriving heart of Winter Haven, just minutes from world-renowned theme parks. Each unit showcases a spacious, modern design with 2 bedrooms and 2 bathrooms, offering the perfect balance of style, comfort, and functionality for long-term tenants or short-term guests. Built with

    Amalia Lucena LPT REALTY, LLC

    306 Avenue P NW, Winter Haven, FL 33881
  • /20

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft

    1109 5th St SW, Winter Haven, FL 33880

    Step inside this versatile 3-bedroom, 2-bathroom Winter Haven home and discover endless possibilities without HOA! Featuring a spacious living area, updated kitchen with ample cabinet space, and a primary suite, this home is designed for comfort and functionality. Situated on a generous fenced-in lot perfect for outdoor entertaining, or future projects, it also offers easy access to major

    Agent Photo

    Carlos DeJesus

    EXIT REALTY 4CORNERS

    (863) 267-9625

    1109 5th St SW, Winter Haven, FL 33880
  • /29

    $449,000

    • 5 Beds
    • 6 Baths
    • 3,015 Sq Ft

    724 W Central Ave, Winter Haven, FL 33880

    Don’t miss this prime investment opportunity! Perfect for adding to or starting your rental portfolio. With a central location and strong tenant demand, this property is ready to generate passive income today. NO seller/creative financing!

    Miraya Lane KELLER WILLIAMS ADVANTAGE III

    724 W Central Ave, Winter Haven, FL 33880
  • /59

    $349,500

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    319 Avenue A NE, Winter Haven, FL 33881

    New Construction in Winter Haven! Built in 2024, this 3-bedroom, 2-bath home offers 1,560 sq. ft. of living space with a 2-car garage. Located on a large lot with an approved permit to build a mother-in-law suite. Features include tile floors throughout, spacious open layout, and kitchen with granite countertops. Conveniently close to hospitals, doctor offices, schools, Legoland, shopping

    Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

    319 Avenue A NE, Winter Haven, FL 33881
  • /63

    $550,000

    • 5 Beds
    • 2 Baths
    • 2,006 Sq Ft

    1818 6th St SE, Winter Haven, FL 33880

    ***FULLY RENOVATED***Discover the perfect blend of modern upgrades and timeless charm in this beautifully updated 3-bedroom, 2-bathroom home.This beautiful property fully renovated with the total 5 bedrooms, new kitchen, new living room, new floor, new bathrooms and the best new backyard in the city. Nestled between Orlando and Tampa with no HOA or CDD, this property offers unmatched freedom and

    Erika Pinto GARCIA REALTY GROUP

    1818 6th St SE, Winter Haven, FL 33880
  • /20

    $310,000

    • 3 Beds
    • 2 Baths
    • 1,543 Sq Ft

    111 Krenson Bay Loop, Winter Haven, FL 33881

    Don’t miss this nearly new 3 bedroom, 2 bath home located in a desirable community in Winter Haven! Built just 2 years ago, this move-in ready property offers modern finishes, and energy-efficient features throughout. The spacious kitchen includes stainless steel appliances, a large island, and ample cabinet space, perfect for entertaining. The split bedroom plan provides privacy, with a generous

    Neisha Crespo CROWN LEGACY REALTY LLC

    111 Krenson Bay Loop, Winter Haven, FL 33881
  • /6

    $129,999

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    888 23rd St NW, Winter Haven, FL 33881

    Welcome to 888 23rd St NW — a charming 1949 block home brimming with potential and ready for a full rehab. Boasting 2 bedrooms, 1 bathroom, and 768 square feet, it’s an ideal canvas for investors or DIY enthusiasts to create a stunning transformation. This 2-bedroom, 1-bathroom property offers 768 square feet of living space, featuring durable laminate and ceramic tile flooring throughout.Set

    Dee Norris NEXTHOME NORRIS & COMPANY REAL

    888 23rd St NW, Winter Haven, FL 33881
  • /20

    $174,500

    • 2 Beds
    • 2 Baths
    • 1,078 Sq Ft

    2050 San Marcos Dr SE Unit 113, Winter Haven, FL 33880

    Welcome to this charming first-floor condominium in the heart of Winter Haven! Offering several upgrades such as hardwood floors, granite countertops and crown molding. Conveniently located on the renowned Chain of Lakes, this spacious 2-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience. Step inside to enjoy an open and inviting floorplan with plenty of natural light

    Agent Photo

    Tony Insua Jr.

    CRAIG BURKE REAL ESTATE GROUP, LLC

    (863) 310-1224

    2050 San Marcos Dr SE Unit 113, Winter Haven, FL 33880
  • /24

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    1865 4th St SE, Winter Haven, FL 33880

    Welcome to 1865 4th St. SE, Winter Haven, FL! Step into charm and possibility with this delightful 3-bedroom, 2-bathroom home nestled in a serene neighborhood. From the moment you enter, you'll be greeted by a spacious living room bathed in natural light—perfect for cozy evenings or lively family gatherings.The kitchen offers generous cabinet space and a welcoming eat-in area, ideal for

    Nette Nelson EXP REALTY LLC

    1865 4th St SE, Winter Haven, FL 33880
  • /14

    $33,500

    • 2 Beds
    • 1.5 Baths
    • 800 Sq Ft

    71 Charlote Dr, Winter Haven, FL 33880

    Welcome to your beautifully updated and renovated mobile home located in a vibrant 55+ community! This charming residence features modern upgrades throughout, ensuring a comfortable and stylish living experience. Step inside to discover an open-concept floor plan that maximizes space and natural light. The updated kitchen boasts new appliances, sleek countertops, and ample cabinetry, making

    Michael Hutcheson Coast to Coast Mobile Home Sales LLC

    71 Charlote Dr, Winter Haven, FL 33880
  • /73

    $260,000

    • 2 Beds
    • 2.5 Baths
    • 2,045 Sq Ft

    11 Casarena Ct, Winter Haven, FL 33881

    Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarean on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and

    Tim Weisheyer DREAM BUILDERS REALTY

    11 Casarena Ct, Winter Haven, FL 33881
  • /39

    $125,000

    • 2 Beds
    • 2 Baths
    • 826 Sq Ft

    2037 San Marcos Dr SE Unit 335, Winter Haven, FL 33880

    Enjoy lakeside living with city convenience in this 2-bedroom, 2-bath Winter Haven Chain of Lakes condo. Featuring luxury vinyl flooring, stainless steel appliances, granite counters, and a breakfast bar, this home blends style with comfort. Relax on the private dock, fish, or swim in the community pool. Just minutes from top shopping, dining, and entertainment—perfect as a weekend getaway,

    Logan Bennett KELLER WILLIAMS REALTY SMART

    2037 San Marcos Dr SE Unit 335, Winter Haven, FL 33880
  • /28

    $225,000

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

    1904 3rd St NE, Winter Haven, FL 33881

    Welcome home to this beautifully updated 4 bed, 2 bath in the heart of Winter Haven! Inside you’ll find stylish upgrades like vinyl flooring, granite countertops, and stainless steel appliances. A brand new roof offers peace of mind, and the inviting side yard is perfect for gatherings, gardening, or simply relaxing in the Florida sun. With ~1,400 sq ft, this move-in ready home is ideal for

    Henry Linder XPERT REALTY GROUP

    1904 3rd St NE, Winter Haven, FL 33881
  • /69

    $775,000

    • 4 Beds
    • 2.5 Baths
    • 2,710 Sq Ft

    1360 Mirror Terrace NW, Winter Haven, FL 33881

    AN AMAZING 4 BEDROOM 2.5 BATHROOM HOME SITUATED ON AN OVERSIZED (.71) AC LOT ON WINTER HAVEN'S FAMOUS CHAIN OF LAKES!!! This home on Spring Lake has amazing water views from the inside of nearly all rooms and especially from the 850 Sq Ft. covered screened patio with oversized pool. Enjoy the shade in both the front and back yards provided by the beautiful oaks while you appreciate the lake

    Bryan Dicks COLDWELL BANKER REALTY

    1360 Mirror Terrace NW, Winter Haven, FL 33881
  • /18

    $275,000

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

    311 Avenue P NW, Winter Haven, FL 33881

    Motivated Seller – Offering $3,000 in Seller Credit! Welcome to your future home in the heart of Winter Haven! -This charming and modern 3-bedroom, 2-bathroom home offers 1,440 sq ft of comfortable living space and was built in 2021 — making it practically new and move-in ready. Nestled on Avenue P NW, this property is perfect for families, first-time buyers, or investors looking for a

    Viviana Arias EXP REALTY LLC

    311 Avenue P NW, Winter Haven, FL 33881
  • /32

    $349,900 Open House 11/21

    • 3 Beds
    • 2 Baths
    • 1,847 Sq Ft

    144 Waterside Cir, Winter Haven, FL 33880

    Welcome home! This beautifully maintained 3-bedroom, 2-bathroom, 2 car garage home offers a perfect blend of comfort and style. Waterside Village is a boutique (48 homes) community located in the heart of Winter Haven. Step inside to discover an open-concept floor plan filled with natural light, high ceilings, and spacious living and dining areas ideal for both relaxing and entertaining. The

    Anita Lowe LOCKHART & ASSOCIATES INC

    144 Waterside Cir, Winter Haven, FL 33880
  • /19

    $215,000

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

    411 Avenue A SE, Winter Haven, FL 33880

    This beautifully updated Winter Haven gem combines style, comfort, and smart upgrades in a location that puts everything you need right at your fingertips. With NO HOA, a durable newer roof, newer A/C, and recent improvements, this home is truly move-in-ready—and packed with charm! A generous lot in a friendly neighborhood combining comfort and convenience. This property offers the perfect

    Penny Miller NUWAVE REALTY

    411 Avenue A SE, Winter Haven, FL 33880
  • /34

    $231,000

    • 3 Beds
    • 1 Bath
    • 1,190 Sq Ft

    104 Avenue K NE, Winter Haven, FL 33881

    Owner Very MOTIVATED!!!! Welcome to 104 Avenue K NE in Winter Haven—a charming, move-in ready 3-bedroom, 1-bath concrete block home offering 1,191+- square feet of tastefully updated living space, including a sunny bonus Florida room and a private, fully fenced backyard. With thoughtful renovations completed in recent years, this home is ideal for first-time buyers, investors, or anyone looking

    April Spaulding LPT REALTY, LLC

    104 Avenue K NE, Winter Haven, FL 33881
  • /27

    $210,000

    • 2 Beds
    • 2.5 Baths
    • 1,281 Sq Ft

    2352 Isle Royale Ct SE, Winter Haven, FL 33880

    Welcome Home to this charming 2 bedroom, 2.5 bathroom townhouse in Park Lake, one of Winter Haven's desirable communities located close to shopping, restaurants, schools, lakes, Legoland and the beautiful downtown Winter Haven area. This move in ready home offers a bright and spacious living area located on the first floor with new luxury vinyl flooring, fresh paint and a convenient half bath for

    Wendy Watson KELLER WILLIAMS REALTY SMART 1

    2352 Isle Royale Ct SE, Winter Haven, FL 33880
  • /40

    $220,000

    • 3 Beds
    • 3 Baths
    • 1,426 Sq Ft

    1858 4th St SE, Winter Haven, FL 33880

    NEW ROOF already installed september 2025, however non functional electrical panel, non functional AC so only CASH and Private HARD MONEY is available for this home. New Roof & Great Structure. With some upgrades and TLC the possibilities are endless as the enclosed carport can be expanded for additional 2 bedrooms to bring to a total 5 bedroom home Rental or for a Large Family to Enjoy. View of

    Jean Cidel SUNSTATE REALTY OF CENTRAL FL

    1858 4th St SE, Winter Haven, FL 33880
  • /21

    $89,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    1700 6th St NW Unit A38, Winter Haven, FL 33881

    Here we go, back to market, Buyer default! The property you are inquiring about is located in Winter Haven, FL, in the Winter Haven Harbour area of Polk County. Now conveniently located is this corner unit with beautiful window views from the third floor, and with recent updates. Two bedrooms, 1 bath, with every square inch utilized for practical purposes. The community is a 55+ and is

    Renee Butler BROKERS REALTY OF CENTRAL FLOR

    1700 6th St NW Unit A38, Winter Haven, FL 33881
  • /32

    $200,000

    • Land
    • 1.09 Acres
    • $183,486 per Acre

    1514 2nd St NW, Winter Haven, FL 33881

    Two contiguous commercial parcels totaling approximately 1.10 acres, both zoned C-3 (Commercial Highway) within the City of Winter Haven. The sites are vacant, level, and free of wetlands or flood zone, making them development-ready. The C3 zoning allows for a wide range of uses including retail, office, restaurant, assisted living, and personal services. Located within the Florence Villa CRA,

    Richie Timmons ESHENBAUGH LAND COMPANY

    1514 2nd St NW, Winter Haven, FL 33881
  • /14

    $1,495,000

    • 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 apartments

    Beau Beery BRG REALTY VENTURES

    669 Avenue B NW, Winter Haven, FL 33881
  • /59

    $609,900

    • 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
  • /65

    $118,900

    • 2 Beds
    • 2 Baths
    • 1,029 Sq Ft

    700 Mirror Terrace NW Unit 702, Winter Haven, FL 33881

    LAKEFRONT! MUST SEE! Charming 55+ LAKEFRONT 2BR 2BA condo in Winter Haven, FL! Located on the top floor of the complex, providing one of the best views in the building. The Spring Lake Towers community offers many amenities and social events. The association fee covers cable, internet, building and grounds maintenance, common facilities including a gym, library, community kitchen, laundry area,

    Agent Photo

    Daniel Hut

    HUT REALTY, LLC

    (863) 356-1216

    700 Mirror Terrace NW Unit 702, Winter Haven, FL 33881
  • /19

    $192,500

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    208 Lake Howard Dr NW Unit 104, Winter Haven, FL 33880

    LOCATED IN THE HEART OF WINTER HAVEN SITS THIS BEAUTIFUL END-UNIT CONDO WITH SPECTACULAR VIEWS OF LAKE HOWARD!!! These units are hard to come by, and with it being an end unit, it has 3 sets of sliding doors along the south side of the unit which allows a massive amount of natural light to flow into the kitchen, dining room and the living room. The great room as well as the Master bedroom share a

    Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    208 Lake Howard Dr NW Unit 104, Winter Haven, FL 33880
  • /95

    $950,000

    • 3 Beds
    • 3 Baths
    • 3,885 Sq Ft

    1540 N Lake Mirror Dr NW, Winter Haven, FL 33881

    One-of-a-Kind Architectural Treasure by Gene Leedy on the Winter Haven Chain of Lakes: Gene Leedy and the Winter Haven Chain of Lakes—an extraordinarily combination and opportunity to own a true architectural statement on one of the most unique water-systems in all of Florida. Known as The Guest House, this Mid-Century Modern masterpiece was designed and built by world-renowned architect Gene

    Michael Stone THE STONES REAL ESTATE FIRM

    1540 N Lake Mirror Dr NW, Winter Haven, FL 33881
  • /78

    $45,000

    • 2 Beds
    • 2 Baths
    • 1,177 Sq Ft

    41 Morningside Rd, Winter Haven, FL 33881

    ** Exclusive Listing! Age 55+ Land Lease Community. Contact listing agent below for ALL showings and offers.** You'll know you're looking at your new home as soon as you step inside this comfortably spacious and uniquely appointed 1980 Fuqua Prestige. Priced right at $45,000, and measuring 23x44, plus the 11x15 Florida room, the home will provide an approximate total of 1170 square feet of

    Shawna Kemp Mobile Home Spot Inc.

    41 Morningside Rd, Winter Haven, FL 33881
  • /8

    $349,000

    • 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
  • /26

    $535,000

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

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

    One or more photo(s) has been virtually staged. A RARE HISTORIC MASTERPIECE ESTATE ARCHITECTURALLY DESIGNED, BUILT, AND RESIDED BY CYPRESS GARDENS FOUNDER DICK POPE. 800 West Lake Elbert Drive offers a rare opportunity to own a truly iconic piece of Central Florida’s heritage. Overflowing with timeless character while for today’s living comfort it has been meticulously blended with modern

    Team Papin FLORIDA LUXURY REALTY INC

    800 W Lake Elbert Dr NE, Winter Haven, FL 33881
  • /73

    $379,000

    • 3 Beds
    • 2 Baths
    • 1,752 Sq Ft

    1919 19th St NW, Winter Haven, FL 33881

    It's a renovated 4-bedroom block home beauty in upscale neighborhood. No HOA. Boat ramp in neighborhood. New Roof, new windows, new doors, new hot water heater, new insulation, new electric and new air conditioner 2024. The kitchen has gold handles, refrigerator/ coffee maker combo, and a farmhouse sink. Wood floors are refinished 2025. Kitchen and bathrooms are totally renovated 2024. If you

    Kimberly Saddler LA ROSA REALTY PRESTIGE

    1919 19th St NW, Winter Haven, FL 33881
  • /2

    $235,000

    • 3 Beds
    • 3 Baths
    • 2,363 Sq Ft

    1987 8th St SE, Winter Haven, FL 33880

    Short Sale. "SHORT SALE!! Seller accepting CASH ONLY!! APPROVED SHORT SALE PRICE BY LIEN HOLDER AND CAN CLOSE QUICKLY. Needs TLC. This midcentury POOL home has much potential. It features 3 bedrooms and 3 baths. It has a formal living room area, an office area and a large dining/family room for family gatherings. The fireplace has been converted to gas. Pool enclosure can be developed to be an

    Kelly Hansell COLDWELL BANKER REALTY

    1987 8th St SE, Winter Haven, FL 33880
  • /20

    $119,900

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    333 Lake Howard Dr NW Unit 103C, Winter Haven, FL 33880

    Welcome to 333 Lake Howard Drive – a bright and spacious 2 bedroom, 2-bath unit condo in the desirable Imperial Harbours 55+ lakefront community in Winter Haven. This unit has ample natural light, This well-maintained condo offers an open living and dining area, charming kitchen, primary suite offers a walk-in closet, in-unit laundry, Imperial Harbours offers more than just a home – it’s a

    Kevin Tison LPT REALTY, LLC

    333 Lake Howard Dr NW Unit 103C, Winter Haven, FL 33880

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