Downtown Winter Haven Homes

• 

  

  

  /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
• 

  

  

  /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
• 

  

  /2

  $245,000 Sold Apr 08, 2025

  • 1,452 Sq Ft
  • $169/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1961

  753 Avenue O SE, Winter Haven, FL 33880

  Welcome to this delightful home in the heart of Winter Haven, FL 33880. Nestled in a peaceful neighborhood, this home offers the perfect blend of comfort and convenience. With a bright and airy floor plan, a spacious living area, and a well-appointed kitchen, it’s ideal for both relaxing and entertaining. The primary suite features a private bath, while the second bedroom is perfect for guests, a

  Eddie Collazo RE/MAX REALTY UNLIMITED

  753 Avenue O SE, Winter Haven, FL 33880
• 

  

  

  /32

  Est $357,658 Not Listed For Sale

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

  168 Krenson Bay Loop, Winter Haven, FL 33881

  168 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  

  /44

  $119,900

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

  700 Mirror Terrace NW Unit 303, Winter Haven, FL 33881

  Welcome to SPRING LAKE TOWERS, a premier 55+ community in Winter Haven, Florida offering a relaxed lakefront lifestyle with this well-maintained 2-bedroom, 2-bath condo featuring an open floor plan with stunning lake views, a 12' x 22' great room connected to the kitchen via convenient pass-through, spacious 12' x 18' Primary suite with private bathroom and walk-in closet, 10' x 13' second

  Kevin Tison LPT REALTY, LLC

  700 Mirror Terrace NW Unit 303, Winter Haven, FL 33881
• 

  /2

  $183,000 Sold Apr 08, 2025

  • 1,162 Sq Ft
  • $157/SF
  • 69 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1982

  235 6th St NW Unit 504, Winter Haven, FL 33881

  Welcome to The Haven! Don't miss out on a chance to own a piece of history. Winter Haven gained fame as a water ski community through the release of the 1953 film "Easy to Love" starring Ester Williams. This location was very special part of that filming. The lobby still boasts orginal art and movie posters. This once famous hotel has been converted for living and enjoying the convienences that

  Kami Rickert HOMETRUST REAL ESTATE & PTY MGT

  235 6th St NW Unit 504, Winter Haven, FL 33881
• 

  

  /41

  Est $367,506 Not Listed For Sale

  • 6 Beds
  • 2 Baths
  • 1,944 Sq Ft

  1830 2nd St NW Unit A & B, Winter Haven, FL 33881

  1830 2nd St NW Unit A & B, Winter Haven, FL 33881
• 

  

  /31

  $116,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  1700 6th St NW Unit C26, Winter Haven, FL 33881

  This fully remodeled condo offers comfortable and stylish living with two bedrooms and one bathroom. Enjoy brand-new vinyl flooring throughout, making maintenance a breeze. The kitchen features new appliances and solid surface countertops, while the updated bathroom adds a modern touch.Assigned covered parking is included with the unit. The active 55+ community boasts a newly remodeled,

  Ave Bar CENTURY 21 WATSON & MYERS REALTY

  1700 6th St NW Unit C26, Winter Haven, FL 33881
• 

  /2

  $124,900 Sold Apr 04, 2025

  • 1,072 Sq Ft
  • $117/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1976

  689 Lake Howard Dr NW Unit 214, Winter Haven, FL 33880

  WELCOME TO WELLINGTON! THE WELLINGTON IS A MAINTENANCE-FREE 55 PLUS COMMUNITY SITUATED JUST MINUTES TO DOWNTOWN WINTER HAVEN!! THE CONDO BUILDING IS LOCATED DIRECTLY ACROSS THE STREET FROM LAKE HOWARD & THE FAMOUS "CHAIN OF LAKES"! This property boasts a large living/dining room combination with sliding doors that lead onto a beautiful lanai. The split bedroom floor plan allows for privacy &

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  689 Lake Howard Dr NW Unit 214, Winter Haven, FL 33880
• 

  

  /13

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 648 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /25

  $189,000

  • 2 Beds
  • 2 Baths
  • 1,306 Sq Ft

  2180 San Marcos Cir SE Unit 401, Winter Haven, FL 33880

  Discover the perfect blend of lakeside relaxation and city convenience in this beautifully situated condo on Winter Haven’s famous Chain of Lakes. Whether you're a nature lover or simply enjoy a serene view with your morning coffee, this home delivers.Tucked within a well-maintained community, this condo offers exclusive access to a private dock—perfect for relaxing by the water or

  Jonathan Turner LAND SOURCE REALTY, LLC

  2180 San Marcos Cir SE Unit 401, Winter Haven, FL 33880
• 

  /2

  $287,000 Sold Apr 04, 2025

  • 1,391 Sq Ft
  • $206/SF
  • 37 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  2227 Howard Ave W, Winter Haven, FL 33880

  ***BACK ON THE MARKET***Beautiful home that is everything you’ve been looking for with NO HOA, this charming 3-bedroom, 2-bathroom home, nestled on a serene dead-end street, offering privacy and tranquility is it. With a thoughtful split bedroom layout and vaulted ceilings, the home exudes an inviting and spacious atmosphere. The vinyl plank flooring adds a modern touch throughout the entire

  Kathy Agner REMAX EXPERTS

  2227 Howard Ave W, Winter Haven, FL 33880
• 

  

  /17

  Est $305,053 Not Listed For Sale

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

  259 Krenson Bay Loop, Winter Haven, FL 33881

  259 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /3

  $260,000

  • 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
• 

  /2

  $305,000 Sold Apr 02, 2025

  • 1,962 Sq Ft
  • $155/SF
  • 97 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2024

  221 Avenue P NW, Winter Haven, FL 33881

  Welcome to this beautifully crafted 2024 spec home built by custom home builder Raysin Construction, where quality craftsmanship and thoughtful design come together effortlessly. Offering the perfect blend of country charm and city convenience, this 4-bedroom, 2-bath home delivers comfort, style, and functionality—all with no HOA or CDD restrictions. Whether you're looking for a peaceful retreat

  Lisa Siner LPT REALTY, LLC

  221 Avenue P NW, Winter Haven, FL 33881
• 

  

  /16

  Est $321,786 Not Listed For Sale

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

  280 Krenson Bay Loop, Winter Haven, FL 33881

  280 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /11

  $945,000

  • Land
  • 1 Acre
  • $945,000 per Acre

  0 Olympian Way, Winter Haven, FL 33881

  1 AC Retail Outparcel For Sale or Lease in Winter Haven, Florida! This prime location along Martin Luther King Blvd boasts 30,000+ AADT and over 215 feet of frontage. Positioned in Winter Haven’s commercial corridor, this outparcel is located next to many national retailers, including a Home Depot-anchored shopping center. Zoned C-3, or Commercial Highway, this site allows for a wide range of

  Zack Strang POLK REALTY ADVISORS LLC

  0 Olympian Way, Winter Haven, FL 33881
• 

  /2

  $280,500 Sold Apr 02, 2025

  • 1,131 Sq Ft
  • $248/SF
  • 147 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1955

  405 Avenue M NE, Winter Haven, FL 33881

  **100 PERCENT OCCUPIED****FREE HOME WARRANTY-CLEAN 4 POINT AND WIND MIT PLUS SURVEY ATTACHED TO MLS- BLOCK DUPLEX REMODELED- Discover this beautifully renovated duplex, nestled in a quiet neighborhood of Winter Haven, featuring two spacious 1-bedroom, 1-bathroom units. BOTH UNITS RENTED at $1200 dollar per month tenants paying electric with a 1 year lease. Each unit boasts its own PRIVATE PORCH,

  Betsy Tinervin REAL BROKER, LLC

  405 Avenue M NE, Winter Haven, FL 33881
• 

  

  /17

  Est $301,586 Not Listed For Sale

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

  132 Krenson Bay Loop, Winter Haven, FL 33881

  132 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /28

  $799,900

  • 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
• 

  /2

  $105,000 Sold Apr 02, 2025

  • 666 Sq Ft
  • $158/SF
  • 216 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1985

  2040 San Marcos Dr SE Unit 205, Winter Haven, FL 33880

  Affordable and cozy One-Bedroom Condo in Park Lake Subdivision in Winter Haven.Discover the perfect starter home with this charming one-bedroom, one-bath condo in the desirable Park Lake Subdivision. The inviting laminate flooring extends through both the living room and bedroom, creating a warm and cohesive atmosphere. Step out onto the balcony through sliding glass doors to enjoy a

  Maria Santillo REMAX EXPERTS

  2040 San Marcos Dr SE Unit 205, Winter Haven, FL 33880
• 

  

  /19

  Est $287,979 Not Listed For Sale

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

  116 Krenson Bay Loop, Winter Haven, FL 33881

  116 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /31

  $185,700

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

  2218 Abbey Rd, Winter Haven, FL 33880

  ?? Fresh, Fun & Fully Ready—Turnkey Villa in Stonebridge, Winter Haven! ??Step into your stress-free Florida life with this modern 2-bed, 2-bath villa that brings the chill and skips the upkeep. Located in the sought-after Stonebridge community, this move-in-ready home is the definition of “no work, all play.”? What makes it a must-see:Airy + Bright Vibes: Vaulted

  Larry King VIVA ORLANDO REALTY INC.

  2218 Abbey Rd, Winter Haven, FL 33880
• 

  /2

  $120,000 Sold Mar 31, 2025

  • 955 Sq Ft
  • $126/SF
  • 4 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  504 Sears Ave NE, Winter Haven, FL 33881

  Great 2 bedroom 1 bath Lakefront house that sits on Lake Maude. Needs work but great lot.

  Matt Helmling BAY VISION REALTY INC

  504 Sears Ave NE, Winter Haven, FL 33881
• 

  

  /34

  Est $300,951 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,698 Sq Ft

  124 Krenson Bay Loop, Winter Haven, FL 33881

  124 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /23

  $899,000

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  802 Avenue L SW, Winter Haven, FL 33880

  Rare lakefront development opportunity located in the Winter Haven Downtown CRA District. This 2.46-acre property offers beautiful views of Lake May and access to the Winter Haven Chain of Lakes. Current DOR use code (0852) permits duplexes, triplexes, and quadplexes — up to 9 units — in Polk City, Auburndale, Lake Alfred, and Winter Haven.The property includes a 1,208 sq ft concrete

  Veronica Bard LA ROSA REALTY PRESTIGE

  802 Avenue L SW, Winter Haven, FL 33880
• 

  /2

  $555,000 Sold Mar 28, 2025

  • 3,060 Sq Ft
  • $181/SF
  • 47 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1921

  306 Avenue C NE, Winter Haven, FL 33881

  Mixed used zoned residential/commercial. Live here, work here! This property has had extensive and complete renovations to include total updating sparing no expense while keeping the historical charm of this 1930 historic home while incorporating an excellent business location. This home can be utilized for your personal residence or your business location or both! Currently this home was

  Barry Macchione REMAX EXPERTS

  306 Avenue C NE, Winter Haven, FL 33881
• 

  

  /4

  Not Listed For Sale

  0 1st St N Unit O6013920, Winter Haven, FL 33881

  0 1st St N Unit O6013920, Winter Haven, FL 33881
• 

  

  /43

  $285,000

  • 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
• 

  /2

  $284,850 Sold Mar 28, 2025

  • 1,900 Sq Ft
  • $150/SF
  • 335 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1920

  653 Avenue A SW, Winter Haven, FL 33880

  Seller willing to contribute up to $6,500 towards a 2-1 Temporary Interest Rate Buydown with preferred lender! NEW ROOF JUST INSTALLED. Located blocks from Lake Howard, and restaurants, bars, and shopping, this newly renovated home is near everything Winter Haven has to offer! The interior has been fully updated with a spacious brand-new kitchen with stainless steel appliances, granite

  Angie Reynolds PORCHLIGHT HOMES LLC

  653 Avenue A SW, Winter Haven, FL 33880
• 

  

  /24

  Est $302,889 Not Listed For Sale

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

  260 Krenson Bay Loop, Winter Haven, FL 33881

  260 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /16

  $219,900

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  769 Avenue Q SE, Winter Haven, FL 33880

  Beautifully Renovated 2-Bedroom Condo in 55+ Community. Welcome home to this beautifully renovated 2-bedroom, 1.5-bath condo in a peaceful 55+ community. With 960 sq. ft. of living space, this move-in-ready home features new luxury vinyl plank (LVP) flooring throughout, a remodeled kitchen and bathrooms, freshly painted interior and exterior, new appliances, and new double-pane windows with a

  Jorge Zea BLUE LIGHTHOUSE REALTY INC

  769 Avenue Q SE, Winter Haven, FL 33880
• 

  /2

  $331,545 Sold Mar 28, 2025

  • 2,202 Sq Ft
  • $151/SF
  • 908 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2023

  212 Krenson Bay Loop, Winter Haven, FL 33881

  MOVE-IN READY! NO CDD & LOW HOA in a GATED COMMUNITY! This charming home, located in a secure GATED COMMUNITY, offers 4 spacious bedrooms, 2.5 baths, a dining room, and a covered lanai. The first floor is beautifully tiled, and features door-blind inserts, 30-year mildew-resistant dimensional shingles, and upgraded 5 1/4" baseboards throughout. Wood window sills add a touch of elegance. The home

  Cassandre Martin ADAMS HOMES REALTY

  212 Krenson Bay Loop, Winter Haven, FL 33881
• 

  /2

  Est $316,188 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,846 Sq Ft

  240 Krenson Bay Loop, Winter Haven, FL 33881

  240 Krenson Bay Loop, Winter Haven, FL 33881
• 

  

  /10

  $130,000

  • 2 Beds
  • 1.5 Baths
  • 1,050 Sq Ft

  689 Lake Howard Dr NW Unit 1E, Winter Haven, FL 33880

  Beautiful property located in a remarkable location! Do not miss out on the opportunity of making this property yours. Discover the perfect blend of comfort and convenience in this beautiful Winter Haven property. Nestled in a peaceful neighborhood, this property offers spacious living areas and a welcoming atmosphere. Enjoy bright living, a well-appointed kitchen, and generously sized bedrooms.

  Maria Rivera RIVERA & ASSOCIATES REALTY

  689 Lake Howard Dr NW Unit 1E, Winter Haven, FL 33880
• 

  /2

  $315,000 Sold Mar 26, 2025

  • 1,001 Sq Ft
  • $315/SF
  • 1 Day On Market

  • 3 Beds
  • 1 Bath
  • Built 1950

  1530 S Lake Howard Dr, Winter Haven, FL 33880

  CHARMING PROPERTY ON LAKE HOWARD! Don’t miss this incredible opportunity to enjoy lakefront living. This three bedroom home showcases a newly renovated interior including an impressive kitchen and delightful bathroom, while great new windows afford spectacular views of Lake Howard. Contemporary ceiling fans and fixtures bring a present-day flair to the home, along with several barn door closures

  Erin Floyd COLDWELL BANKER REALTY

  1530 S Lake Howard Dr, Winter Haven, FL 33880
• 

  

  /26

  Est $124,583 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  900 Avenue Z SE Unit 204, Winter Haven, FL 33880

  900 Avenue Z SE Unit 204, Winter Haven, FL 33880
• 

  

  /32

  $119,000

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

  333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880

  Welcome to 333 Lake Howard Drive, where comfort, convenience, and a vibrant 55+ lifestyle come together in the heart of Winter Haven’s charming lakefront community. Nestled within the desirable Imperial Harbours 55+ community, this spacious and sunlit 3-bedroom, 2-bathroom corner-unit condo that oversees the pool offers the ideal space for those seeking a relaxed, maintenance-free lifestyle. From

  Jason Prieto LPT REALTY, LLC

  333 Lake Howard Dr NW Unit 204D, Winter Haven, FL 33880
• 

  /2

  $195,000 Sold Mar 26, 2025

  • 1,128 Sq Ft
  • $173/SF
  • 207 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  2179 Castle Point, Winter Haven, FL 33880

  A MUST SEE!! Welcome home to this STUNNING 2 bedroom, 2 bath CORNER villa in Stonebridge! LOW Monthly HOA Fee offers a community pool (just steps away), lawn maintenance, and exterior pest control. ROOF REPLACED IN 2019! AC was replaced in 2017. As you step into the home, you are greeted by the GORGEOUS kitchen that overlooks the dining room and living room with a HIGH CEILING providing that

  Chrissi Jasso ASSOCIATE REALTY

  2179 Castle Point, Winter Haven, FL 33880
• 

  

  /86

  Est $409,872 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,968 Sq Ft

  102 Covington Cove SE, Winter Haven, FL 33880

  102 Covington Cove SE, Winter Haven, FL 33880

Showing Results 281 - 320, Page 8 of 18