Downtown Winter Haven Homes

• 

  

  

  /34

  Est $176,109 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft

  125 Avenue A SE, Winter Haven, FL 33880

  125 Avenue A SE, Winter Haven, FL 33880
• 

  

  

  /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
• 

  

  /2

  $220,000 Sold May 02, 2025

  • 1,312 Sq Ft
  • $168/SF
  • 245 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1995

  2310 Isle Royale Ct SE, Winter Haven, FL 33880

  Welcome to this meticulously updated townhome that blends modern comforts with prime convenience. This exquisite 3-bedroom, 2.5-bathroom home is designed to offer a relaxed, stylish lifestyle with thoughtful enhancements throughout. Through the charming screened portico entry, find gleaming hard floors that flow seamlessly through the open-concept living spaces—no carpet in sight. The heart of

  Kayly Malinas JOHN WOOD REALTY, INC.

  2310 Isle Royale Ct SE, Winter Haven, FL 33880
• 

  

  

  /100

  Est $741,440 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,288 Sq Ft

  1700 S Lake Mirror Dr NW, Winter Haven, FL 33881

  1700 S Lake Mirror Dr NW, Winter Haven, FL 33881
• 

  

  

  /32

  $195,000

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft

  679 Avenue Q SE, Winter Haven, FL 33880

  More photos to come soon! Come see what the charming home has to offer, in the heart of beautiful Winter Haven. The home features 3 bedrooms, with 2 full bathrooms. The master bath features a separate shower and tub area. Large front sunroom gives ample space for seating to relax with your morning coffee, with plenty of natural lighting. Extra large master bedroom, with its own back porch area

  Rachel Sowder DOWN HOME REALTY, LLLP

  679 Avenue Q SE, Winter Haven, FL 33880
• 

  /2

  $375,000 Sold May 01, 2025

  • 2,368 Sq Ft
  • $158/SF
  • 174 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1955

  937 Avenue L SE, Winter Haven, FL 33880

  JUST REDUCED!!! IMPROVED PRICE, SELLER IS MOTIVATED!! SALE FELL, BACK ON MARKET & READY FOR YOUR FAMILY!!! SPACIOUS SOUTHEAST WINTER HAVEN POOL HOME WITH 4 BEDROOMS, 5 BATHS & NO HOA, A MID-CENTURY MODERN DESIGN! If you are looking for a large, comfortable pool home for you and your family, close to EVERYTHING, this is it!! 4 bedrooms with the primary bedroom situated in a very private setting.

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  937 Avenue L SE, Winter Haven, FL 33880
• 

  

  /20

  Est $239,362 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,290 Sq Ft

  507 Sears Ave NE, Winter Haven, FL 33881

  507 Sears Ave NE, 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 Spot Mobile Home Spot Inc.

  41 Morningside Rd, Winter Haven, FL 33881
• 

  /2

  $325,000 Sold Apr 30, 2025

  • Land
  • 6.33 Acres
  • $51,343 per Acre

  • 410 Days On Market

  160 2nd St SW, Winter Haven, FL 33880

  Great opportunity to build. Motivated seller. Light industrial zoning with multiple land use. Great location

  Maha Matta PA RE/MAX TOWN & COUNTRY REALTY

  160 2nd St SW, Winter Haven, FL 33880
• 

  

  /33

  Est $259,376 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft

  313 Avenue P NW, Winter Haven, FL 33881

  313 Avenue P 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
• 

  /2

  $136,670 Sold Apr 28, 2025

  • 1,413 Sq Ft
  • $97/SF
  • 9 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  700 Mirror Terrace NW Unit 501, Winter Haven, FL 33881

  **AWESOME LAKE VIEWS FROM THIS DIRECT LAKEFRONT CONDO ON THE CHAIN-OF-LAKES** RARELY AVAILABLE WEST END-UNIT. NEW CENTRAL AIR CONDITIONER INSTALLED 03/2022, NEW WATER HEATER INSTALLED 07/2023, NEW DISHWASHER INSTALLED 2024, SOME NEW DLB. PANE WINDOWS. Spring Lake Towers Condominium is an (age 55+) NON-SMOKING, NO PETS complex located in central Florida in the beautiful city of Winter Haven. Dock

  Chris Goode JUDY B CLEAVES PROPERTIES INC

  700 Mirror Terrace NW Unit 501, Winter Haven, FL 33881
• 

  

  /7

  Est $41,858 Not Listed For Sale

  1627 1st St N, Winter Haven, FL 33881

  1627 1st St N, Winter Haven, FL 33881
• 

  

  /25

  $950,000

  • Land
  • 0.25 Acre
  • $3,800,000 per Acre

  233 W Central Ave, Winter Haven, FL 33880

  SPECTACULAR LOCATION DOWNTOWN WINTER HAVEN— This vacant commercial property is prime real estate on beautiful Central Avenue. Excellent visibility and access to major thoroughfares around the city, this lot stands within the CRA District that offers attractive development incentives. Walking distance to businesses, shops and where nightlife entertainment is offered. Don’t miss this extraordinary

  Erin Floyd COLDWELL BANKER REALTY

  233 W Central Ave, Winter Haven, FL 33880
• 

  /2

  $210,000 Sold Apr 25, 2025

  • 1,125 Sq Ft
  • $187/SF
  • 15 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  1819 4th Ct SE, Winter Haven, FL 33880

  Step into a home where charm and character shine in every corner! This delightful 2-bedroom, 1-bathroom home is filled with warm earthy tones and unique details that make it truly one of a kind. The cozy living room features a built-in entertainment center, while the kitchen showcases a custom refrigerator and microwave cabinet designed to blend seamlessly with the space and slate tile flooring.

  CarLee Marchetti STAR REALTY OF WINTER HAVEN

  1819 4th Ct SE, Winter Haven, FL 33880
• 

  

  /11

  Est $311,243 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft

  232 Krenson Bay Loop, Winter Haven, FL 33881

  232 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /43

  $252,000

  • 2 Beds
  • 2 Baths
  • 1,832 Sq Ft

  961 Piedmont Dr SE, Winter Haven, FL 33880

  BRAND NEW ROOF, architectural character, and unbeatable location. Mid-Century Ranch in an Established Neighborhood – A True Vintage Gem! Step into timeless style and effortless comfort with this mid-century ranch home, ideally situated just off Cypress Gardens Boulevard and near all your favorite shopping and dining spots. Featuring two spacious primary bedrooms, each with its en suite

  Josh Taylor VILLAGE REALTY OF WINTER HAVEN

  961 Piedmont Dr SE, Winter Haven, FL 33880
• 

  /2

  $150,000 Sold Apr 23, 2025

  • 1,347 Sq Ft
  • $111/SF
  • 84 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  1776 6th St NW Unit 407, Winter Haven, FL 33881

  Immaculate 2/2 Condo in the Desirable 55+ Community of Lakeridge CondominiumsWelcome to this beautifully maintained 2-bedroom, 2-bathroom condo, offering 1,347 sq. ft. of comfortable living space in the picturesque "Chain of Lakes" city of Winter Haven, Florida. Nestled in the sought-after Lakeridge Condominiums, this property provides a carefree, maintenance-free lifestyle perfect for those

  Amanda Edgar KELLER WILLIAMS REALTY SMART 1

  1776 6th St NW Unit 407, Winter Haven, FL 33881
• 

  

  /15

  Est $313,661 Not Listed For Sale

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

  236 Krenson Bay Loop, Winter Haven, FL 33881

  236 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /24

  $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. 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

  Team Papin FLORIDA LUXURY REALTY INC

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

  /2

  $192,000 Sold Apr 21, 2025

  • 1,131 Sq Ft
  • $170/SF
  • 13 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  2028 Kings Crossing SW, Winter Haven, FL 33880

  Welcome to the tranquil living within the Stonebridge community! This move-in ready 2 bedroom, 2 full bathroom home is ready for its new owner! Before entering the property, a private courtyard sits in the front of the home, with access from the sliding glass doors in the kitchen. Once inside, you're greeted by a beautiful kitchen with a gas range, stainless steel appliances, and a pantry. The

  Matthew Cogan LOMBARDO TEAM REAL ESTATE LLC

  2028 Kings Crossing SW, Winter Haven, FL 33880
• 

  

  /16

  Est $313,731 Not Listed For Sale

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

  224 Krenson Bay Loop, Winter Haven, FL 33881

  224 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /73

  $389,000

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

  1919 19th St NW, Winter Haven, FL 33881

  It's a beauty. No HOA. Renovated. Desired neighborhood. Help with closing $10,000. Boat ramp in neighborhood. This newly renovated beauty is in a much-desired 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

  Kimberly Saddler LA ROSA REALTY PRESTIGE

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

  /2

  $260,000 Sold Apr 17, 2025

  • 2,045 Sq Ft
  • $127/SF
  • 12 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1985

  26 Casarena Ct, Winter Haven, FL 33881

  CHAIN OF LAKES COMMUNITY...2 Bedroom/2.5 Bathroom Two-story townhouse nestled on the quiet and quaint gated community of Casarena located on the shores of the Lake Cannon. The living room features vaulted ceilings and glass sliding doors allowing plenty of natural light to fill the space. The kitchen features newer stainless-steel appliances and easy to clean tile floors and a breakfast bar

  Cheryl Brewer COLDWELL BANKER REALTY

  26 Casarena Ct, Winter Haven, FL 33881
• 

  

  /15

  Est $315,304 Not Listed For Sale

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

  228 Krenson Bay Loop, Winter Haven, FL 33881

  228 Krenson Bay Loop, 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
• 

  /2

  $298,000 Sold Apr 15, 2025

  • 2,067 Sq Ft
  • $144/SF
  • 217 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1966

  1905 Manor Cir SE, Winter Haven, FL 33880

  Welcome to your dream home, where comfort and elegance await at every turn. Upon entering, you're greeted by a warm fireplace, framed by freshly painted walls in a soothing neutral color scheme. The kitchen features modern An accent backsplash adds a touch of excitement to your culinary adventures, complemented by all stainless steel appliances. and a new HVAC system ensures comfort year-round.

  GREGORY BLACKALL VERANDA REALTY GROUP

  1905 Manor Cir SE, Winter Haven, FL 33880
• 

  

  /51

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,984 Sq Ft

  420 4th St NW, Winter Haven, FL 33881

  420 4th St NW, Winter Haven, FL 33881
• 

  

  /26

  $234,900

  • 3 Beds
  • 2 Baths
  • 1,623 Sq Ft

  780 Oleander Dr SE, Winter Haven, FL 33880

  Steps to shopping and restaurants, 1⁄4 acre yard, fenced in the rear, and overlooked by a spacious screened room. Ideal for outside enjoyment. 3 bedrooms, 2 bathrooms plus a living room, dinette and an office or dining room area, all are nice size rooms, so that you don’t feel crowded. You will be so comfortable with a BRAND NEW A/C unit that was just installed May, 2025! This home is very

  Mike Nolen COLDWELL BANKER REALTY

  780 Oleander Dr SE, Winter Haven, FL 33880
• 

  /2

  $270,000 Sold Apr 11, 2025

  • 1,554 Sq Ft
  • $174/SF
  • 124 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1955

  555 Avenue O SE, Winter Haven, FL 33880

  The Seller has agreed to pay for a BRAND NEW ROOF to give the Buyer peace of mind. This spacious four-bedroom, two-bathroom home is ideally situated in a prime location behind the Walmart Superstore. The property features brand new carpeting, updated bathrooms, and fresh paint throughout. The kitchen is equipped with stainless steel appliances, including a gas oven. Inside, you’ll find ample

  Amy Reynolds LOCKHART & ASSOCIATES INC

  555 Avenue O SE, Winter Haven, FL 33880
• 

  

  /33

  Not Listed For Sale

  • 22 Beds
  • 14 Baths
  • 9,616 Sq Ft

  710 Avenue C SW, Winter Haven, FL 33880

  710 Avenue C SW, Winter Haven, FL 33880
• 

  

  /59

  $34,000

  • 2 Beds
  • 2 Baths
  • 1,085 Sq Ft

  66 Misty Meadow 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 are looking at your new home as soon as you set your eyes on this very appealing 1981 Fleetwood Sand Pointe. Priced at $34,000, and measuring 23x40, plus the 11x15 Florida room, this home will provide approximately 1080 total square feet of interior living space,

  Shawna Spot Mobile Home Spot Inc.

  66 Misty Meadow Rd, Winter Haven, FL 33881
• 

  /2

  $117,000 Sold Apr 11, 2025

  • 1,030 Sq Ft
  • $114/SF
  • 180 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

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

  Amazing lakefront condo now available!! Make your home here in beautiful central Florida! This 2 bedroom, 2 bath condo with in unit laundry and updated kitchen and baths is ready for you. This open floor plan home has an updated kitchen with pass through window to a dining area and open floor plan living room. Enjoy coffee sitting in your Florida room with gorgeous lakefront views. A spacious

  Whitney Roberts LPT REALTY, LLC

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

  

  /46

  Est $174,157 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  947 2nd St SE, Winter Haven, FL 33880

  947 2nd St SE, Winter Haven, FL 33880
• 

  

  /85

  $49,900

  • 2 Beds
  • 2 Baths
  • 1,504 Sq Ft

  72 Misty Meadow Rd, Winter Haven, FL 33881

  ** Exclusive Listing! Contact listing agent below for ALL showings and offers.** This is a manufactured home on leased land. The land/lot is not included with the sale. Here's your very own piece of Florida paradise, this super spacious and exceptionally well maintained 1986 Fuqua. Priced right at $49,900, and measuring 25x52, plus a 12x17 Florida room, this home will provide approximately

  Shawna Spot Mobile Home Spot Inc.

  72 Misty Meadow Rd, Winter Haven, FL 33881
• 

  /2

  $263,000 Sold Apr 10, 2025

  • 1,197 Sq Ft
  • $220/SF
  • 42 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  834 Avenue I NE, Winter Haven, FL 33881

  Welcome to 834 Avenue I NE, Winter Haven, FL – a beautifully maintained 3-bedroom, 2-bathroom home built in 2018 with an open floor plan and modern finishes. Located directly across from Polk State College, this home offers convenience, style and space with no HOA restrictions, located on a 0.21 acre lot!Step inside and fall in love with the spacious open layout, perfect for entertaining or

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  834 Avenue I NE, Winter Haven, FL 33881
• 

  

  /31

  Est $339,242 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,202 Sq Ft

  164 Krenson Bay Loop, Winter Haven, FL 33881

  164 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /20

  $139,900

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

  2173 Castle Point, Winter Haven, FL 33880

  Great Opportunity in Winter Haven! This 2-bedroom, 2-bath home offers a solid layout with great potential for updates and improvements. Enjoy a screened lanai that's perfect for morning coffee, and take advantage of the community pool for relaxing afternoons. This home needs some updating but has good bones and a functional floor plan—ideal for investors, snowbirds, or buyers looking to add their

  Jenny Robles VYLLA HOME

  2173 Castle Point, Winter Haven, FL 33880
• 

  /2

  $210,000 Sold Apr 08, 2025

  • 1,059 Sq Ft
  • $198/SF
  • 13 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1946

  100 Avenue K NE, Winter Haven, FL 33881

  Take a look at this cute 2BR/1BA home with lake view overlooking Lake Silver with one 1 car garage on a conner lot. This house is move in ready and offers a large living room and separate dining room with built-in cabinets, cute kitchen with wood cabinets, appliances. 2 large bedrooms with walk-in closets

  Maria Torres Beltran CENTURY 21 NEXT LEVEL REALTY

  100 Avenue K NE, Winter Haven, FL 33881
• 

  

  /40

  Est $357,288 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,405 Sq Ft

  176 Krenson Bay Loop, Winter Haven, FL 33881

  176 Krenson Bay Loop, Winter Haven, FL 33881

Showing Results 241 - 280, Page 7 of 18