Downtown Winter Haven Homes

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  /21

  $300,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,517 Sq Ft

  645 Avenue A NE, Winter Haven, FL 33881

  Under contract-accepting backup offers. 645 Ave A NE is a waterfront property situated near the edge of downtown Winter Haven. Built in 1939 The house features 2 bedrooms, 1 bathroom, 1 half bathroom, and is equipped with new or updated appliances, air conditioning, plumbing, and electrical work as of 2022. The roof and most windows were also updated in 2024. Within one mile of downtown, it is

  Franco Poerio Skubna CENTURY 21 MYERS REALTY

  645 Avenue A NE, Winter Haven, FL 33881
• 

  

  

  /11

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 626 Sq Ft
  • House for Rent

  1756 2nd St NE, Winter Haven, FL 33881

  VACANT, MOVE-IN READY & PET FRIENDLY! Lease for just $1,600/month! Located in the lovely and up-and-coming Winter Haven area, this completely remodeled historic 1930s home has been beautifully restored to its former glory. This charming home offers 2 bedrooms and 1 well-appointed full bathroom, perfect for comfortable living. Situated on an oversized, fully fenced corner lot—perfect for pets—the

  Daniel Hut HUT REALTY, LLC

  1756 2nd St NE, Winter Haven, FL 33881
• 

  

  /2

  $190,000 Sold Jun 30, 2025

  • 1,252 Sq Ft
  • $152/SF
  • 26 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  2185 Knights Rd, Winter Haven, FL 33880

  Newly renovated condo

  angie chacko PEOPLE'S CHOICE REALTY SVC LLC

  2185 Knights Rd, Winter Haven, FL 33880
• 

  

  

  /16

  Est $312,836 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  104 Krenson Bay Loop, Winter Haven, FL 33881

  104 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  

  /41

  $275,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  945 7th St NW, Winter Haven, FL 33881

  Under contract-accepting backup offers. Charming 1925 Historic Home Near Lake Howard!Step into timeless character with this beautifully preserved 3-bedroom, 2-bath residence offering just over 1,700 sq. ft. of living space. From the moment you enter, the formal living room with its cozy fireplace sets the tone for the home’s historic charm. Additional highlights include a formal dining

  Dolores Vogel LEGACY REAL ESTATE CENTER INC

  945 7th St NW, Winter Haven, FL 33881
• 

  

  /14

  $1,580 per month

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • House for Rent

  924 Ave T SE, Winter Haven, FL 33880

  Sign a lease today and get HALF OFF your 2nd full month rent for free! Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering,

  924 Ave T SE, Winter Haven, FL 33880
• 

  /2

  $112,500 Sold Jun 30, 2025

  • 1,347 Sq Ft
  • $84/SF
  • 130 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  1776 6th St NW Unit 209, Winter Haven, FL 33881

  Conveniently located condominium in LakeRidge Winter Haven, close to downtown entertainment, hospitals, shopping, gas stations, and restaurants. A 55 year old community with a strategic location. What else could you ask for, when you enjoy peace and security of a gated community but yet close to everything. This unit has 2 spacious bedroom and 2 bath with an open concept style a large living room

  Mary Sorrell MAZELG REALTY

  1776 6th St NW Unit 209, Winter Haven, FL 33881
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  /4

  Not Listed For Sale

  0 Avenue South NW, Winter Haven, FL 33881

  0 Avenue South NW, Winter Haven, FL 33881
• 

  

  /42

  $289,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  1204 Lake Elbert Dr SE, Winter Haven, FL 33880

  Beautiful 3 bedrooms and 2 bathrooms single family home with amazing and wide-open lake view!! Everything new from top to bottom: new roof, Impact windows, high traffic laminated floors; new bathrooms and new kitchen with stainless steel appliances and quartz countertops. Huge fenced backyard and new paved driveway. A must see before it is gone!

  Ana Saya Direct Realty Solutions

  1204 Lake Elbert Dr SE, Winter Haven, FL 33880
• 

  

  /11

  $1,150 per month

  • 2 Beds
  • 1 Bath
  • 468 Sq Ft
  • Apartment for Rent

  514 Avenue C NE Unit 4, Winter Haven, FL 33881

  Fantastic 2 bedroom/1.0 bathroom apartment totally renovated and ready for its new occupants. Unit is in close proximity of schools, including Jewett School of the Arts, Fred G. Garner Elementary School, and Frank E. Brigham Academy. 2 minute walk to Rotary Park. 7 minute walk to Kiwanis Park. 14 minute walk to Winter Haven Tennis Center. Water is included in the rent.

  Angela Chapman CAPITAL REALTY GROUP FLORIDA

  514 Avenue C NE Unit 4, Winter Haven, FL 33881
• 

  /2

  $215,000 Sold Jun 30, 2025

  • 1,240 Sq Ft
  • $173/SF
  • 383 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1915

  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 $2,345.00 and an annual gross income of $28,140.00. 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
• 

  

  /43

  Est $442,553 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,335 Sq Ft

  980 Wedgewood Ave, Winter Haven, FL 33880

  980 Wedgewood Ave, 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
• 

  

  /20

  $1,300 per month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  117 5th St NE Unit 117, Winter Haven, FL 33881

  Property Id: 1302032** AVAILABLE BY AUGUST 7/25 **First level unit, Fully Furnished 2 bed/1 bath. Close to Downtown, Restaurants, Attractions, Hospitals, Schools etc. Monthly Rent includes:Water, Trash, Sewer and Gas Fuel for Water Heater. Complete Kitchen set, Bathroom and Dining room. Communal Laundry coming soon! Requirements:No Evictions, Must have good income

  117 5th St NE Unit 117, Winter Haven, FL 33881
• 

  /2

  $215,000 Sold Jun 27, 2025

  • 1,230 Sq Ft
  • $175/SF
  • 187 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  149 Avenue E SW, Winter Haven, FL 33880

  Price Improvement and Prime Location in Downtown Winter Haven! Discover this rare opportunity to own a property perfectly zoned for commercial and residential use in the heart of Winter Haven’s bustling downtown. This beautifully situated home features a welcoming front porch, a spacious corner lot, and a fenced backyard—ideal for privacy and versatility. Inside, original hardwood floors

  Josh Taylor VILLAGE REALTY OF WINTER HAVEN

  149 Avenue E SW, Winter Haven, FL 33880
• 

  /2

  Est $261,882 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,339 Sq Ft

  820 Avenue R NE, Winter Haven, FL 33881

  820 Avenue R NE, Winter Haven, FL 33881
• 

  

  /28

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft

  539 Avenue A NE, Winter Haven, FL 33881

  Charming Downtown Winter Haven Home This 3-bedroom, 2-bath home offers over 1,376 sq. ft. of living space plus a spacious 13x19 Flexspace that can be tailored to your needs—perfect as a home office, playroom, or guest retreat. Built in 1936, this home blends timeless character with modern updates. Original hardwood floors add warmth and charm, while the upgraded kitchen and bathrooms

  Laurie Nock LPT REALTY, LLC

  539 Avenue A NE, Winter Haven, FL 33881
• 

  

  /10

  $1,395 per month

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Apartment for Rent

  796 Avenue L SW, Winter Haven, FL 33880

  FOR RENT - 2 BEDROOM/2 BATH DUPLEX - NEW CONSTRUCTION - COME SEE THIS GORGEOUS UNIT. IT COMES WITH ALL OF THE APPLIANCES. IT IS CLOSE TO THE POLK PARKWAY TO THE SOUTH AND ALL OF CENTRAL FLORIDA'S ATTRACTIONS TO THE EAST AND IT'S NEAR LEGOLAND! COME SEE IT TODAY!

  Linda Andre COLDWELL BANKER REALTY

  796 Avenue L SW, Winter Haven, FL 33880
• 

  /2

  $200,000 Sold Jun 26, 2025

  • 1,346 Sq Ft
  • $149/SF
  • 247 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1961

  520 Avenue L SE, Winter Haven, FL 33880

  Welcome Home... Check out this beautifully 4 beds and 2 baths renovated home that is practically new. New updates include: new roof, flooring, paint inside and out, plumbing, kitchen, and so much more. Move in ready. This home also boasts a large back yard. Located at the excellent schools, shopping, and a variety of dining options, this home is perfectly positioned for your lifestyle. Don't miss

  Trinh Le SOGO REAL ESTATE SERVICES LLC

  520 Avenue L SE, Winter Haven, FL 33880
• 

  

  /20

  Est $295,181 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  107 Krenson Bay Loop, Winter Haven, FL 33881

  107 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /5

  $510,000

  • 3 Beds
  • 4 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.

  Miraya Lane KELLER WILLIAMS ADVANTAGE III

  724 W Central Ave, Winter Haven, FL 33880
• 

  

  /31

  $1,550 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Condo for Rent

  2160 San Marcos Cir SE Unit 512, Winter Haven, FL 33880

  **No Deposit, Partial Deposit, or Full Deposit Options for renters are available — supported by ObligoExperience modern lakeside living in this beautifully upgraded 2-bedroom, 2-bathroom loft condo located at 2160 San Marcos Cir SE, Unit 512, in Winter Haven, FL. This newly constructed 1,250 sq ft upstairs unit offers a bright, open layout enhanced by fresh interior paint, luxury vinyl

  Avi Sela SAFETYNET REALTY

  2160 San Marcos Cir SE Unit 512, Winter Haven, FL 33880
• 

  /2

  $240,000 Sold Jun 20, 2025

  • 1,403 Sq Ft
  • $171/SF
  • 74 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2020

  2014 S Lake Cannon Dr NW, Winter Haven, FL 33881

  Cute 5 year old home with views of Lake Cannon. This ranch style home has 3 bedrooms and 2 bathrooms. The open floor plan features a kitchen with granite countertops which opens up to the living room with sliding doors to your fenced in back yard and patio. The primary bedroom has ensuite bathroom. Private laundry room and single attached garage. No HOA.

  Anne Halbert LIVE FLORIDA REALTY

  2014 S Lake Cannon Dr NW, Winter Haven, FL 33881
• 

  

  /37

  Est $202,648 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,013 Sq Ft

  203 Avenue South NE, Winter Haven, FL 33881

  203 Avenue South NE, Winter Haven, FL 33881
• 

  

  /39

  $219,999

  • 4 Beds
  • 2.5 Baths
  • 1,564 Sq Ft

  309 Avenue G SE, Winter Haven, FL 33880

  SELLER IS MOTIVATED! Submit highest and best by 11:59pm on Sunday, September 20, 2025. Discover the charm and potential of this vintage 4-bedroom, 2.5-bathroom home in the heart of Winter Haven. Bursting with character, this fully furnished residence offers strong bones, timeless details, and a rare opportunity for anyone seeking a CASH-ONLY, AS-IS property. No-HOA, No-CDD & LOW TAXES! The home

  Shani Carty KELLER WILLIAMS REALTY AT THE PARKS

  309 Avenue G SE, Winter Haven, FL 33880
• 

  

  /35

  $1,860 per month

  • 3 Beds
  • 2 Baths
  • 2,154 Sq Ft
  • Apartment for Rent

  2233 9th St SE, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Waterfront corner unit townhome on Lake Lulu! Chain of lakes living! Check out this 3 bedroom 2 bath 2160 sq ft townhome. This property offers stunning views of Lake Lulu. The home boast an open floor plan. Spacious bedrooms. 2 car garage with workshop. Spacious Laundry room with washer and dryer connections. Large screen room with amazing water

  John-Michael Elliott S & D REAL ESTATE SERVICE LLC

  2233 9th St SE, Winter Haven, FL 33880
• 

  /2

  $210,000 Sold Jun 20, 2025

  • 1,567 Sq Ft
  • $134/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  20 24th St SW, Winter Haven, FL 33880

  MULTIPLE OFFERS RECEIVED…REQUESTING HIGHEST & BEST BY SUNDAY APRIL 13th @ 2PM EST. Excellent opportunity to buy this 3 Bedroom, 2 Bath home located in the heart of Winter Haven just minutes from Lake Howard. Offering tons of potential...featuring tile flooring through-out, updated kitchen with stainless steel appliances, updated bathrooms and a large screened-in lanai, 1 car garage and carport,

  Cheryl Brewer COLDWELL BANKER REALTY

  20 24th St SW, Winter Haven, FL 33880
• 

  

  /12

  Est $112,010 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 648 Sq Ft

  2075 Isle Royale Ct SE Unit 167, Winter Haven, FL 33880

  2075 Isle Royale Ct SE Unit 167, Winter Haven, FL 33880
• 

  

  /44

  $189,900

  • 2 Beds
  • 1 Bath
  • 1,392 Sq Ft

  500 Avenue L NE, Winter Haven, FL 33881

  BRAND NEW ROOF 08/2025! This cozy 2 bedroom, 1 bath home offers comfort, convenience, and character in a quiet, established neighborhood. Situated on a desirable corner lot, the property features a fenced-in courtyard perfect for outdoor relaxation or pets, plus a welcoming front porch to enjoy your mornings. Additional highlights include a screened-in side area ideal for entertaining, a shed

  Christina Loesch AGILE GROUP REALTY

  500 Avenue L NE, Winter Haven, FL 33881
• 

  

  /9

  $1,200 per month

  • 2 Beds
  • 1 Bath
  • 793 Sq Ft
  • Townhouse for Rent

  1736 3rd St NW Unit B, Winter Haven, FL 33881

  Welcome to this cozy and beautifully maintained 2-bedroom, 1-bathroom duplex, perfect for those seeking comfort and convenience. This duplex is ideally situated just minutes from local shopping, dining, and entertainment, making it the perfect spot for those who love being close to all the action. There is also a small backyard for you to relax and play. Schedule your showing with me today!

  Chelsey Collins LA ROSA REALTY PRESTIGE

  1736 3rd St NW Unit B, Winter Haven, FL 33881
• 

  /2

  $175,000 Sold Jun 18, 2025

  • 833 Sq Ft
  • $210/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1961

  1215 6th St NE, Winter Haven, FL 33881

  Beautiful, move in ready home with large backyard.

  Danielle Galloway CFL REALTY PROS LLC

  1215 6th St NE, Winter Haven, FL 33881
• 

  

  /26

  Est $233,474 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,931 Sq Ft

  689 Sears Ave NE, Winter Haven, FL 33881

  689 Sears Ave NE, Winter Haven, FL 33881
• 

  

  /63

  $550,000

  • 3 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 house has now 2 extra bedrooms after renovations 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

  Erika Pinto GARCIA REALTY GROUP

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

  

  /32

  $1,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,722 Sq Ft
  • House for Rent

  434 Avenue C NE, Winter Haven, FL 33881

  Lovely older home with original hardwood flooring located near downtown Winter Haven. Fenced in yard great for kids or animals. Located half way between Tampa and Orlando.

  Steven Baron BARON HOLDINGS REAL ESTATE LLC

  434 Avenue C NE, Winter Haven, FL 33881
• 

  /2

  $248,000 Sold Jun 12, 2025

  • 1,900 Sq Ft
  • $131/SF
  • 13 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1914

  649 Avenue J NW, Winter Haven, FL 33881

  Welcome to a charming, historic, and completely refreshed 2 story home without an HOA. This beautiful home is located in the heart of Winter Haven FL. This charming home has 4 bedrooms along with 2 fully functional bathrooms. You will see as you enter this home you are adorned by beautiful natural light that shines into the living room from large open view windows. The 3 bedrooms on the first

  Nikii Cheng LA ROSA REALTY PRESTIGE

  649 Avenue J NW, Winter Haven, FL 33881
• 

  

  /18

  Est $216,458 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,013 Sq Ft

  1313 8th St SW, Winter Haven, FL 33880

  1313 8th St SW, Winter Haven, FL 33880
• 

  

  /32

  $259,900

  • 4 Beds
  • 3 Baths
  • 2,001 Sq Ft

  1324 3rd St NE, Winter Haven, FL 33881

  Welcome! This 4-bedroom, 3-bathroom home offers a comfortable single-level design with an efficient layout that maximizes functionality, providing a versatile floor plan for everyday life. Recent major upgrades include fresh interior and exterior paint, all new flooring, and a serviced HVAC System. Its cozy covered front porch creates a welcoming entrance and comfortable outdoor space to relax,

  Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  1324 3rd St NE, Winter Haven, FL 33881
• 

  

  /6

  $1,300 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  645 7th St NE Unit 647, Winter Haven, FL 33881

  Beautifully updated 2 bed/1 bath duplex at 647 7th St NE, Winter Haven, FL! Features modern vinyl plank flooring, granite countertops, ceiling fans in bedrooms and living area, and convenient in-unit washer/dryer hookups. Bright and spacious with 900 sq. ft., this home is ideally located near LEGOLAND, Polk State College, Downtown Winter Haven, shopping, and dining. Perfect for comfortable,

  Pedro Cartagena 1513 REALTY LLC

  645 7th St NE Unit 647, Winter Haven, FL 33881
• 

  /2

  $300,000 Sold Jun 12, 2025

  • 1,989 Sq Ft
  • $151/SF
  • 33 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2017

  806 Avenue G NE, Winter Haven, FL 33881

  Priced to move! Welcome to your dream home—perfectly nestled between Lake Elbert and Lake Martha with convenient access to nearby boat ramps. This beautifully updated 4-bedroom, 2-bath residence sits on an oversized lot and offers both space and style just two blocks from Polk State College in Winter Haven. You are just minutes away from Winter Haven Hospital, the walking track at Polk State

  Hannah Armbruster LOCKHART & ASSOCIATES INC

  806 Avenue G NE, Winter Haven, FL 33881
• 

  

  /17

  Est $214,306 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,212 Sq Ft

  124 Avenue H SE, Winter Haven, FL 33880

  124 Avenue H SE, Winter Haven, FL 33880

Showing Results 121 - 160, Page 4 of 18