Downtown Winter Haven Homes

• 

  

  

  /21

  $249,500

  • 2 Beds
  • 2.5 Baths
  • 2,085 Sq Ft

  14 Casarena Ct, Winter Haven, FL 33881

  Beautiful Condo featuring 2-Bedroom, 2.5-Bath in Gated Casarena on the Lakes! Located in a small community, this contemporary Mediterranean-style townhome offers a perfect open floor plan is that features tile floors downstairs and true hardwood oak floors upstairs, creating a wonderful flow throughout the home. The kitchen features solid wood maple cabinetry with tumbled marble countertops,

  Brian Stephens EXP REALTY LLC

  14 Casarena Ct, Winter Haven, FL 33881
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  /2

  $270,000 Sold Mar 26, 2025

  • 1,171 Sq Ft
  • $231/SF
  • 231 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  254 24th St SW, Winter Haven, FL 33880

  Looking for an great starter home or the perfect investment opportunity??? Look no further! With nearly 1,200 living sq. ft. this 3 bedroom 2 bathroom home is nestled in the heart of Winter Haven just minutes from downtown. The home was previously rented on a monthly income of $1,950.00. Best of all there is NO HOA, the ROOF was just replaced in 2022 and the AC was replaced in 2021. Additional

  Matt Mesimer KELLER WILLIAMS REALTY SMART 1

  254 24th St SW, Winter Haven, FL 33880
• 

  

  

  /50

  Est $106,736 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 648 Sq Ft

  2075 Isle Royale Ct SE Unit 266, Winter Haven, FL 33880

  2075 Isle Royale Ct SE Unit 266, Winter Haven, FL 33880
• 

  

  

  /24

  $119,900

  • 2 Beds
  • 2 Baths
  • 826 Sq Ft

  2037 San Marcos Dr SE Unit 217, Winter Haven, FL 33880

  Price Improvement & Great opportunity to add your renovation style to this 2 bedroom 2 full bath condo in Park Lake. Located on the 2nd floor close to the elevator with tremendous rental returns. Luxury Vinyl flooring in main living area & primary bedroom. Gas range & Water Heater. Ceiling fans throughout...Roof 2021...Washer/Dryer included with private laundry closet. NEW AC being installed.

  Dora Siler FOLIO REALTY LLC

  2037 San Marcos Dr SE Unit 217, Winter Haven, FL 33880
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  /2

  $95,000 Sold Mar 24, 2025

  • 648 Sq Ft
  • $147/SF
  • 120 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1987

  2065 Isle Royale Ct SE Unit 143, Winter Haven, FL 33880

  Talk about location!!! This charming downstairs 1-bedroom, 1-bathroom condo tucked away in the Park Lake waterfront community offers low-maintenance living just steps away from Chick-fil-A, Panera Bread, and Starbucks, with downtown shopping, restaurants, Walmart, medical offices, and more just minutes away—providing easy access to all your essentials. The open great room combines the living and

  CarLee Marchetti STAR REALTY OF WINTER HAVEN

  2065 Isle Royale Ct SE Unit 143, Winter Haven, FL 33880
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  /16

  Est $166,681 Not Listed For Sale

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

  2050 San Marcos Dr SE Unit 114, Winter Haven, FL 33880

  2050 San Marcos Dr SE Unit 114, Winter Haven, FL 33880
• 

  

  /25

  $539,900

  • 3 Beds
  • 2.5 Baths
  • 2,118 Sq Ft

  1475 S Lake Howard Dr, Winter Haven, FL 33880

  LAKE FRONT PROPERTY FOR SALE ON THE CHAIN OF LAKES ON LAKE HOWARD!!! This chain of lakes has 20 connecting lakes. If you enjoy water sports, fishing or just time on the water this lake front property may be a perfect fit for you. This Home has a detached Mother In-Law Suite, Fire place, New flooring, New split AC unit and a Updated Bathroom. If there is NO NEED for a Mother In-Law Suite it

  Steve Pospichal COLDWELL BANKER REALTY

  1475 S Lake Howard Dr, Winter Haven, FL 33880
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  /2

  $220,000 Sold Mar 21, 2025

  • 1,195 Sq Ft
  • $184/SF
  • 126 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1969

  1623 3rd St NW, Winter Haven, FL 33881

  Presenting a beautifully renovated 4-bedroom, 2-bathroom gem, the most affordable 4/2 in Winter Haven. This remarkable home offers nearly 1,200 square feet of living space on a .21-acre lot, complete with a fenced backyard, making it perfect for families or entertaining guests. Fully updated, it features a new roof, new air conditioning, new plumbing, new electrical systems, fresh interior and

  Devon Bascombe LPT REALTY, LLC

  1623 3rd St NW, Winter Haven, FL 33881
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  /48

  Est $212,751 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,210 Sq Ft

  752 Oleander Dr SE, Winter Haven, FL 33880

  752 Oleander Dr SE, Winter Haven, FL 33880
• 

  

  /50

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  657 Avenue C SW, Winter Haven, FL 33880

  Discover this beautifully 3/2 home with a brand new roof 2022 in serene neighborhood .With no HOA or CDD ,this property offers peace of mind and potential for a primary residence ,rental investment ,or Airbnb .Currently rented for $2,150 per month .The open concept living space is filled with natural light .The kitchen features a glass cooktop range ,ample counter space .Each generously sized

  Hala Saleh Keller Williams Realty of PSL

  657 Avenue C SW, Winter Haven, FL 33880
• 

  /2

  $515,000 Sold Mar 21, 2025

  • 3,708 Sq Ft
  • $139/SF
  • 277 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1920

  1561 N Lake Howard Dr, Winter Haven, FL 33881

  *Seller is motivated- Agents bring your buyers! Welcome to 1561 Lake Howard Dr, a piece of history nestled on an oversized corner lot with large fenced back yard in the heart of Winter Haven. The home sits along the picturesque Northern shores of Lake Howard, part of the "Chain of Lakes", and sought after community of Interlaken. The home offers an impressive 125 feet of LAKE FRONTAGE, ready for

  Suzanna Rudd KELLER WILLIAMS REALTY SMART 1

  1561 N Lake Howard Dr, Winter Haven, FL 33881
• 

  /2

  Est $357,270 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,716 Sq Ft

  804 Avenue L SW, Winter Haven, FL 33880

  804 Avenue L SW, Winter Haven, FL 33880
• 

  

  /22

  $164,500

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  700 Mirror Terrace NW Unit 403, Winter Haven, FL 33881

  Winter Haven's premier condominium located directly overlooking the picturesque Lake Spring that is part of the Chain of Lakes. Be the first to enjoy this 4th floor extensively remodeled and upgraded 2BR/2BA unit including brand-new appliances. Completely furnished. Turn-key ready. Exquisitely maintained building and has passed the newly required Florida Milestone Inspection with flying colors!

  Scott Kline KLINE REAL ESTATE SERVICES

  700 Mirror Terrace NW Unit 403, Winter Haven, FL 33881
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  /2

  $212,000 Sold Mar 17, 2025

  • 2,051 Sq Ft
  • $103/SF
  • 48 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1963

  680 Avenue N SE, Winter Haven, FL 33880

  BACK ON THE MARKET. BUYERS DID NOT QUALIFY FOR LOAN. SELLING ASAP.Charming 3-Bedroom Home with Modern Updates in Prime Winter Haven Location. Recent updates include a brand-new roof and a newer electrical panel installed within the last five years. This home offers a cozy fireplace, a detached 2 car garage, and a flexible layout. This home also has an additional bedroom and bathroom that

  Steven Koleno BEYCOME OF FLORIDA LLC

  680 Avenue N SE, Winter Haven, FL 33880
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  /25

  Est $153,615 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft

  812 Avenue N SW, Winter Haven, FL 33880

  812 Avenue N SW, Winter Haven, FL 33880
• 

  

  /21

  $214,999

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft

  1328 3rd St NE, Winter Haven, FL 33881

  This beautifully renovated home is move-in ready and just minutes from Downtown Winter Haven! Inside, you'll find brand-new flooring, a new water heater, updated light fixtures, and a stunning kitchen featuring granite countertops and stainless steel appliances. The electrical and plumbing systems have been upgraded, and the refreshed bathroom boasts new countertops and stylish

  Henry Linder XPERT REALTY GROUP

  1328 3rd St NE, Winter Haven, FL 33881
• 

  /2

  $330,045 Sold Mar 17, 2025

  • 2,202 Sq Ft
  • $150/SF
  • 373 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  304 Krenson Bay Loop, Winter Haven, FL 33881

  Under Construction. Beautiful Corner Lot Home in a Gated Community!Welcome to this stunning 2,202 sq. ft. home featuring 4 bedrooms, 2.5 baths, and a 2-car garage. This move-in ready gem offers an open floor plan with a dining room, a laundry room on the first floor, and a gorgeous lanai perfect for relaxing Upstairs, you’ll find all four bedrooms, each with walk-in closets, and 2.5

  Cassandre Martin ADAMS HOMES REALTY

  304 Krenson Bay Loop, Winter Haven, FL 33881
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  /36

  Est $176,746 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,252 Sq Ft

  2187 Knights Rd, Winter Haven, FL 33880

  2187 Knights Rd, Winter Haven, FL 33880
• 

  

  /40

  $95,000

  • 2 Beds
  • 1.5 Baths
  • 840 Sq Ft

  1700 6th St NW Unit A36, Winter Haven, FL 33881

  Charming Condo at Winter Haven Harbor. Welcome to this beautifully updated 2-bedroom, 1.5-bath condo located in the desirable Winter Haven Harbor community! Situated on the third floor with elevator access, this unit offers both convenience and style. Step inside to discover a newly renovated kitchen, featuring elegant granite countertops, new cabinetry, and a square stainless steel deep sink

  Annie Wood HARPER REALTY FL, LLC

  1700 6th St NW Unit A36, Winter Haven, FL 33881
• 

  /2

  $343,967 Sold Mar 17, 2025

  • 2,405 Sq Ft
  • $143/SF
  • 379 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  208 Krenson Bay Loop, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Under Construction. Charming 2,405 Sq. Ft. Home with Loft and No Rear Neighbors in a Gated Community!Welcome to this stunning 4-bedroom, 2.5-bathroom home featuring a loft and an oversized lot with no rear neighbors. The open floor plan includes a dining room and a first-floor laundry room, while the second floor offers a LOFT and four spacious

  Cassandre Martin ADAMS HOMES REALTY

  208 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /14

  Est $204,184 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  106 Mayfair Place SW, Winter Haven, FL 33880

  106 Mayfair Place SW, Winter Haven, FL 33880
• 

  

  /65

  $22,000

  • 2 Beds
  • 2 Baths
  • 920 Sq Ft

  49 Morningside Rd, Winter Haven, FL 33881

  ** Exclusive Listing! Age 55+ Land Lease Community. Contact listing agent below for ALL showings and offers.** You will have an easy time making yourself right at home inside this very appealing 1978 Fleetwood Barrington. Priced right at $22,000, and measuring 23x40, plus the 12x16 screen room, this home will provide approximately 1110 square feet of enjoyable living space, with two bedrooms

  Shawna Spot Mobile Home Spot Inc.

  49 Morningside Rd, Winter Haven, FL 33881
• 

  

  /18

  $150,000 Sold Mar 14, 2025

  • 1,432 Sq Ft
  • $105/SF
  • 27 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1967

  611 Avenue South NE, Winter Haven, FL 33881

  PRIME INVESTMENT PROPERTY- DUPLEX FOR SALE. THIS ONE WILL BE PERFECT TO ADD TO YOUR PORTFOLIO. NEEDS REHAB. ONE UNIT (3 BEDROOM ONE BATHROOM) IS TENANT OCCUPIED AND ONE UNIT (TWO BEDROOM ONE BATHROOM) IS VACANT. LOCATED JUST OFF OF BEAUTIFUL LAKE MAUDE (TWO PUBLIC FISHING PIERS) WITH LAKE MAUDE NATURE PARK, RECREATION PARK, A WALKING TRAIL AND WINTER HAVEN CULTURAL CENTER CLOSE BY. ALSO IN

  Twanna Dewdney LA ROSA REALTY PRESTIGE

  611 Avenue South NE, Winter Haven, FL 33881
• 

  

  /4

  Est $777,232 Not Listed For Sale

  100 3rd St SW, Winter Haven, FL 33880

  100 3rd St SW, Winter Haven, FL 33880
• 

  

  /50

  $99,995

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft

  333 Lake Howard Dr NW Unit 314D, Winter Haven, FL 33880

  Picture yourself in this top-floor, 3-bedroom, 2-bathroom condo with a Sun/Florida room, nestled in the desirable Imperial Harbor community of Winter Haven. With easy access via an elevator, this is the peaceful 55+ retreat you’ve been searching for!Imagine waking up and enjoying a morning stroll to the private community dock on Lake Howard, where you can cast a fishing line or set off on a boat

  Justin Cans IMPACT REALTY TAMPA BAY

  333 Lake Howard Dr NW Unit 314D, Winter Haven, FL 33880
• 

  /2

  $105,000 Sold Mar 14, 2025

  • 992 Sq Ft
  • $106/SF
  • 132 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1980

  1864 Avenue Q SW Unit C13, Winter Haven, FL 33880

  Excellent investment opportunity or for first time buyer, priced to sell quickly! This property features 2 spacious bedrooms with 1.5 baths and good location to Auburndale or Winter Haven! Close to Winter Haven's beautiful Chain of Lakes and Lake Shipp park.

  Jose Quintana PREMIER ESTATE AGENCY LLC

  1864 Avenue Q SW Unit C13, Winter Haven, FL 33880
• 

  

  /13

  Est $122,333 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  639 Avenue F NW Unit 8, Winter Haven, FL 33881

  639 Avenue F NW Unit 8, Winter Haven, FL 33881
• 

  

  /47

  $224,900

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

  2348 Isle Royale Ct SE, Winter Haven, FL 33880

  Recently Fully Renovated Townhouse – Move-In Ready! Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and worry-free living. All 3 bathrooms fully renovated with fresh, modern finishes, Brand-new kitchen featuring new

  Fatma Higdon HIGDON HOMES REALTY LLC

  2348 Isle Royale Ct SE, Winter Haven, FL 33880
• 

  

  /16

  $175,000 Sold Mar 11, 2025

  • 750 Sq Ft
  • $233/SF
  • 5 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1959

  229 Avenue J NE, Winter Haven, FL 33881

  This cozy cottage with a lakeview is waiting for you to call it "home sweet home." The renovated one bedroom, one bath is perfectly located for an owner who works at the Winter Haven Hospital, Bond or Gessler Clinics, or an employee or student of Polk State College. Throughout the home is a dark gray slate tile that contrasts nicely with the freshly painted white walls. Large windows look out

  Anita Todd ADDISON & COMPANY

  229 Avenue J NE, Winter Haven, FL 33881
• 

  

  /31

  Est $341,198 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,800 Sq Ft

  205 Palmetto Ave NW, Winter Haven, FL 33881

  205 Palmetto Ave NW, Winter Haven, FL 33881
• 

  

  /19

  $215,000

  • 2 Beds
  • 2.5 Baths
  • 1,309 Sq Ft

  436 Avenue G SE, Winter Haven, FL 33880

  Welcome to this solid concrete block home with a new roof (2022) and screened in front porch. Step right into your home which features an open floorplan. The bedrooms are spacious with walk in closets. Each bedroom has a bathroom and there is even a guest half bath. At the back of the house there is a quaint sitting area with windows all around. Single car garage with garage door opener. The

  Cathy Marino CATHY S. MARINO REALTY, INC.

  436 Avenue G SE, Winter Haven, FL 33880
• 

  

  /50

  $270,000 Sold Mar 10, 2025

  • 1,830 Sq Ft
  • $148/SF
  • 27 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1956

  703 Avenue L SE, Winter Haven, FL 33880

  Welcome to your perfect home in Winter Haven, Florida, NO HOA and situated on a large 0.25 acre lot!Nestled in a serene neighborhood, this charming 4-bedroom, 2-bathroom home is perfect for homebuyers seeking comfort, convenience, and style. From the moment you step inside, you'll appreciate the seamless flow of ceramic tile flooring throughout, combining durability with aesthetic appeal. The

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  703 Avenue L SE, Winter Haven, FL 33880
• 

  

  /88

  Est $883,718 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 4,856 Sq Ft

  1320 S Lake Mirror Dr NW, Winter Haven, FL 33881

  1320 S Lake Mirror Dr NW, Winter Haven, FL 33881
• 

  

  /36

  $75,000

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  1700 6th St NW Unit C27, Winter Haven, FL 33881

  Welcome to your one bedroom one bath 55+ condo located on the second floor. There is Ceramic tile in the kitchen and bathrooms. The kitchen features an abundance of cabinetry. Vertical blinds are the finishing touches to all of the windows. Front porch area is entirely screened. The community features a massive heated pool, clubhouse, shuffleboard, and a grilling area with a nice area to

  Annie Wood HARPER REALTY FL, LLC

  1700 6th St NW Unit C27, Winter Haven, FL 33881
• 

  

  /18

  $309,909 Sold Mar 10, 2025

  • 1,846 Sq Ft
  • $168/SF
  • 122 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2021

  296 Krenson Bay Loop, Winter Haven, FL 33881

  Welcome to Krenson Bay, a charming gated community! This move-in ready home offers 4 bedrooms, 2 bathrooms, and a 2-car garage within 1,820 square feet. Enjoy the vaulted ceilings, tile flooring throughout (except in the bedrooms), a formal dining room, a cozy breakfast nook, and a covered lanai. The main bedroom features a walk-in closet, a garden tub, a separate shower, and double sinks.

  Cassandre Martin ADAMS HOMES REALTY

  296 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /46

  Est $134,904 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,347 Sq Ft

  1776 6th St NW Unit 708, Winter Haven, FL 33881

  1776 6th St NW Unit 708, Winter Haven, FL 33881
• 

  

  /16

  $185,000

  • 3 Beds
  • 1.5 Baths
  • 986 Sq Ft

  412 2nd St SW, Winter Haven, FL 33880

  New Roof!!! on this AFFORDABLE Downtown Winter Haven Move-in-Ready 3 bedroom, 1.5 bathroom home. This home received an extensive facelift in 2021. Updates include interior and exterior paint, LED can lighting, luxury vinyl plank flooring, kitchen cabinets, granite countertops, bathroom vanities, a fenced yard and more. Don't miss your opportunity to live in Downtown Winter Haven walkable to all

  David Craig 1513 REALTY LLC

  412 2nd St SW, Winter Haven, FL 33880
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  /28

  $270,000 Sold Mar 07, 2025

  • 1,418 Sq Ft
  • $190/SF
  • 81 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1951

  1905 16th St NW, Winter Haven, FL 33881

  Pride of Ownership! This wonderfully renovated 3 bed/2 bath, solid concrete block home, on a nice size lot, stands out with attention to detail. Fenced back yard comes complete with a brand-new, covered, outdoor kitchen providing wonderful family entertainment. Fresh paint inside and out, the roof, water heater, HVAC and ducts, windows, baseboards, kitchen appliances, cabinets backsplash,

  Carmen Padilla LOCKHART & ASSOCIATES INC

  1905 16th St NW, Winter Haven, FL 33881
• 

  

  /16

  Est $140,699 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,347 Sq Ft

  1776 6th St NW Unit 108, Winter Haven, FL 33881

  1776 6th St NW Unit 108, 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

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