Winter Haven, FL Homes

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  /60

  $164,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft

  200 El Camino Dr Unit 101, Winter Haven, FL 33884

  Under contract-accepting backup offers. Welcome to the "SEVILLE" located in beautiful Orchid Springs. This is a large (1,617 sq ft) triple-split bedroom plan condo. This is a three bedroom, two and one half bath corner-unit residence located on the ground floor. The home offers loads of upgrades--remodeled kitchen and baths, new roof, all new plumbing, newer appliances including washer and dryer.

  

  Brenda J. Quinn

  QUINN & COMPANY REALTORS, LLC

  (863) 282-7384

  200 El Camino Dr Unit 101, Winter Haven, FL 33884
• 

  

  

  /35

  $2,475 per month

  • 4 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • House for Rent

  300 Royal Palm Way, Winter Haven, FL 33881

  ***If you see this listing on CRAIGSLIST or FACEBOOK MARKETPLACE, it is fraud. Apply only on the My New Rental website***Be one of the first to move into these recently built, energy-efficient homes, LOADED with the best finishes. If you have pets, not only do we allow them, but we have homes available that include a fenced in yard! Landscape is included! All appliances are included! The

  300 Royal Palm Way, Winter Haven, FL 33881
• 

  

  /2

  $265,000 Sold Oct 24, 2025

  1568 S Lake Shipp Dr, Winter Haven, FL 33880

  • 5 Beds
  • 3 Baths
  • 1,824 Sq Ft
  • Built 1955

  Last Sold Summary

  • 24% Below List Price
  • $145/SF
  • 174 Days On Market

  Last Listing Agent Jordan Prais 54 REALTY LLC

  1568 S Lake Shipp Dr, Winter Haven, FL 33880
• 

  

  

  /17

  Est $404,690 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 2,592 Sq Ft

  5764 E County Road 542, Winter Haven, FL 33880

  5764 E County Road 542, Winter Haven, FL 33880
• 

  

  

  /16

  $79,900

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  213 Lakeside Ranch Cir, Winter Haven, FL 33881

  Experience relaxed Florida living in this furnished 2-bedroom, 1-bath manufactured home located in the gated 55+ community of Lakeside Ranch. The home features laminate flooring with carpeted bedrooms, central A/C, and a roof that is only 2 years old, offering added peace of mind for the next owner. Residents enjoy an impressive array of amenities, including a heated pool, library, shuffleboard,

  

  Carlos DeJesus

  EXIT REALTY 4CORNERS

  (863) 285-3315

  213 Lakeside Ranch Cir, Winter Haven, FL 33881
• 

  

  /10

  $1,400 per month

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

  3125 Avenue S NW Unit A, Winter Haven, FL 33881

  This property offers a comfortable and conveniently located living space in Winter Haven. This unit provides a practical layout designed for easy day-to-day living, making it a great option for tenants seeking affordability and convenience. Located in a quiet residential area, the property offers quick access to shopping, dining, schools, and major roadways, helping simplify daily commutes and

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  3125 Avenue S NW Unit A, Winter Haven, FL 33881
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  /2

  $266,490 Sold Jul 28, 2025

  4904 Kaia Ave, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $177/SF
  • 23 Days On Market

  Current Estimated Value $267,438

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  4904 Kaia Ave, Winter Haven, FL 33884
• 

  /2

  Est $294,096 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,956 Sq Ft

  548 Lucerne Blvd, Winter Haven, FL 33881

  548 Lucerne Blvd, Winter Haven, FL 33881
• 

  /2

  $110,000 Pending

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  201 Richburg Rd, Winter Haven, FL 33880

  Being sold as is. Fixer upper needs a new owner willing to give it some TLC. Cash or renovation loan only.

  

  Tonya Lockamy

  SWAN CITY REALTY LLC

  (863) 260-8127

  201 Richburg Rd, Winter Haven, FL 33880
• 

  

  /35

  $2,425 per month

  • 4 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • House for Rent

  208 Newcastle Ct, Winter Haven, FL 33881

  **If you see this listing on CRAIGSLIST or FACEBOOK MARKETPLACE, it is fraud. Apply only on the My New Rental website***FENCED PROPERTY - Be one of the first to move into these recently built, energy-efficient homes, LOADED with the best finishes. If you have pets, not only do we allow them, but we have homes available that include a fenced in yard! Landscape is included! All appliances

  208 Newcastle Ct, Winter Haven, FL 33881
• 

  /2

  $11,000 Sold Apr 18, 2025

  865 3rd St, Winter Haven, FL 33881

  • Land
  • 0.11 Acre
  • $100,000 per Acre

  Last Sold Summary

  • 56% Below List Price
  • 47 Days On Market

  Last Listing Agent Mary Myers CENTURY 21 MYERS REALTY

  865 3rd St, Winter Haven, FL 33881
• 

  /2

  Est $339,066 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,616 Sq Ft

  3021 Royal Tern Dr, Winter Haven, FL 33881

  3021 Royal Tern Dr, Winter Haven, FL 33881
• 

  

  /42

  $714,900

  • 3 Beds
  • 2 Baths
  • 2,491 Sq Ft

  10 Apple Tree Ln, Winter Haven, FL 33884

  Discover the perfect blend of country living and modern convenience with this well-maintained property set on over 5 acres. This spacious home offers 3 bedrooms plus a dedicated office, 2 full baths, a welcoming living room, formal dining room, and a bright kitchen with a breakfast nook. Step outside to your own private retreat featuring a screened pool, ideal for relaxing or entertaining.

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 473-8196

  10 Apple Tree Ln, Winter Haven, FL 33884
• 

  

  /7

  $1,300 per month

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

  3125 Avenue S NW Unit C, Winter Haven, FL 33881

  Apartment C at 3125 Ave S NW, Winter Haven offers a comfortable and practical living space in a convenient central location located on the second floor. This unit features a functional layout with ample natural light, making it ideal for a tenant seeking an affordable and low-maintenance rental. Located just minutes from major roads, shopping, dining, and everyday conveniences, the property

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  3125 Avenue S NW Unit C, Winter Haven, FL 33881
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  /2

  $275,000 Sold Jul 11, 2025

  555 Heather Glen Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,514 Sq Ft
  • Built 2001

  Last Sold Summary

  • $182/SF
  • 14 Days On Market

  Current Estimated Value $274,121

  Last Listing Agent Lindsey Thibodeau COMPASS FLORIDA LLC

  555 Heather Glen Dr, Winter Haven, FL 33884
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  /41

  Est $293,639 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft

  2185 Rose Blvd, Winter Haven, FL 33881

  2185 Rose Blvd, Winter Haven, FL 33881
• 

  

  /5

  $980,000

  • Land
  • 9.8 Acres
  • $100,000 per Acre

  0 Brigham Rd NW, Winter Haven, FL 33881

  9.8 ACRES (8.5 acres of R-3 + 1.3 acres of Conservation zoning) in the City of Winter Haven. Prime location and already zoned for multifamily development (R-3). Additional unit count with potential zoning change of 1.3 acre portion to R-3. WATER, SEWER & POWER readily available! Property fronts onto Brigham Road and backs up to a Conservation Area. All measurements including acreage count are

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 270-8616

  0 Brigham Rd NW, Winter Haven, FL 33881
• 

  

  /31

  $1,800 per month

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • House for Rent

  3960 Avenue U NW, Winter Haven, FL 33881

  Don't miss out on this 4 bedroom home, at an amazing price. This home has been freshly painted and has ceramic tile throughout. The French doors lead to a paver patio that provides access to a huge backyard. The uncovered gazebo/patio area is perfect for those fire pit evenings. Your front covered patio gives you a Waterview of Lake Blue.

  3960 Avenue U NW, Winter Haven, FL 33881
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  /2

  $279,000 Sold Jun 10, 2025

  1721 Teagan Ln, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • Built 2025

  Last Sold Summary

  • $153/SF
  • 55 Days On Market

  Current Estimated Value $275,161

  Last Listing Agent Sammi Li TOPSKY REALTY INC

  1721 Teagan Ln, Winter Haven, FL 33884
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  /40

  Est $277,704 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,531 Sq Ft

  1436 Wallace Manor Pass, Winter Haven, FL 33880

  1436 Wallace Manor Pass, Winter Haven, FL 33880
• 

  

  /50

  $149,000 Pending

  • 3 Beds
  • 2 Baths
  • 868 Sq Ft

  206 Lake Thomas Dr, Winter Haven, FL 33880

  NO HOA AND PRICED TO SELL.........This is a three bedroom/two bath home that needs some TLC. Lake Thomas Estates is located on Lake Thomas in Winter Haven, Florida and is a well-established neighborhood. For the person with vision, this home could be a darling starter or retirement home. There is tile and vinyl flooring (installed in 2022) throughout for ease of cleaning. Roof was put on in 2022

  

  Brenda J. Quinn

  QUINN & COMPANY REALTORS, LLC

  (863) 624-5899

  206 Lake Thomas Dr, Winter Haven, FL 33880
• 

  

  /13

  $2,420 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  3936 Cypress Landing N Unit 1, Winter Haven, FL 33884

  **Welcome to 3936 Cypress Landing N, Winter Haven, FL 33884** — a beautifully maintained rental that blends comfort, style, and Florida ease. Tucked into a quiet, well-kept community, this inviting home offers bright, open living spaces designed for everyday living and effortless entertaining. Enjoy a spacious layout with generous natural light, a functional kitchen ideal for home-cooked meals,

  Glen Gilzean Beachfront Realty Inc

  3936 Cypress Landing N Unit 1, Winter Haven, FL 33884
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  /2

  $560,000 Sold Feb 28, 2025

  1516 17th St NW, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,557 Sq Ft
  • Built 1939

  Last Sold Summary

  • 3% Below List Price
  • $360/SF
  • 4 Days On Market

  Current Estimated Value $535,280

  Last Listing Agent Michael Ellingson NEARBY REALTY

  1516 17th St NW, Winter Haven, FL 33881
• 

  

  /38

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  304 Temple Ct, Winter Haven, FL 33880

  304 Temple Ct, Winter Haven, FL 33880
• 

  

  /23

  $269,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  112 Saint Kitts Cir, Winter Haven, FL 33884

  Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering an inviting open floor plan, vaulted ceilings, and a comfortable, airy ambiance throughout. Luxury vinyl plank flooring enhances the main living area, adding both style and durability to your new home. With a split-bedroom layout, the spacious primary en-suite is perfectly positioned for privacy, creating a peaceful

  

  Amy Mendez

  CENTURY 21 SUNBELT REALTY

  (863) 862-5307

  112 Saint Kitts Cir, Winter Haven, FL 33884
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  /18

  $899 - $1,385 per month

  The Landings Apartment Homes

  1 - 2 Beds

  102 Landings Way, Winter Haven, FL 33880

  Welcome to The Landings, a tranquil pet friendly retreat nestled among towering trees and lush greenery in the heart of Winter Haven, Florida. As one of our three Winter Haven locations, The Landings offers upgraded 1 and 2 bedroom apartments designed with spacious layouts that maximize comfort and livability. Each home features modern white cabinets that brighten the space, durable vinyl

  102 Landings Way, Winter Haven, FL 33880
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  /14

  $317,000 Sold Sep 23, 2025

  • 2,168 Sq Ft
  • $146/SF

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  3845 Giorgio Dr, Winter Haven, FL 33884

  First-floor primary suite ensures everyone has their own private space. Upstairs loft that can be used fit your needs.

  Meritage Homes

  3845 Giorgio Dr, Winter Haven, FL 33884
• 

  

  /7

  Est $276,125 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,842 Sq Ft

  3711 Julius Estates Blvd, Winter Haven, FL 33881

  3711 Julius Estates Blvd, Winter Haven, FL 33881
• 

  

  /74

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,866 Sq Ft

  3565 Raleigh Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Welcome to this stunning Bonita-II home located in the highly desirable Traditions at Lake Ruby, a gated and maintenance-free 55+ community! From the moment you arrive, you’ll be greeted by a charming front entryway that leads into a spacious living room with soaring ceilings with crown molding. This 3-bedroom, 2-bathroom home sits on a premium lot

  

  Kathy Alexander

  CENTURY 21 WATSON & MYERS REALTY

  (863) 334-2115

  3565 Raleigh Dr, Winter Haven, FL 33884
• 

  

  /32

  $1,285 per month

  • 2 Beds
  • 1.5 Baths
  • 888 Sq Ft
  • Condo for Rent

  845 Orchid Springs Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Discover this charming rental opportunity in the heart of Winter Haven! This well-maintained 2-bedroom, 1.5-bath apartment is ideal for long-term rental, offering comfort, convenience, and an excellent location. The unit includes all appliances, including in-unit washer and dryer, providing added ease for everyday living. Ideally located just 5

  Yuliescar Mendoza EXP REALTY LLC

  845 Orchid Springs Dr, Winter Haven, FL 33884
• 

  /2

  $554,900 Sold Apr 15, 2025

  2400 Crump Rd, Winter Haven, FL 33881

  • 3 Beds
  • 2.5 Baths
  • 2,175 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Below List Price
  • $255/SF
  • 36 Days On Market

  Current Estimated Value $549,857

  Last Listing Agent Steven Smith, PA LOCKHART & ASSOCIATES INC

  2400 Crump Rd, Winter Haven, FL 33881
• 

  

  /23

  Est $319,206 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  213 Majestic Gardens Ln, Winter Haven, FL 33880

  213 Majestic Gardens Ln, Winter Haven, FL 33880
• 

  

  /48

  $335,000

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

  108 Black Skimmer Ln, Winter Haven, FL 33880

  Welcome to your dream home with low HOA fees and no CDD! This 4-bedroom, 2-bathroom home is nestled in the sought-after gated community of Lake Deer. With 1,946 square feet of heated and cooled living space, it's ideal for a growing family! The thoughtful split floor plan ensures privacy and comfort for everyone. The kitchen opens up to a spacious great room with sliding glass doors leading to a

  

  Geraldine Anarumo

  FLORIDA REALTY MARKETPLACE

  (863) 313-1502

  108 Black Skimmer Ln, Winter Haven, FL 33880
• 

  

  /20

  $1,147 - $1,316 per month

  Lakeview Tower-62+ Community

  Studio - 1 Bed

  745 Avenue A SW, Winter Haven, FL 33880

  Lakeview Tower, a Senior 62+ community, offers newly remodeled studio and one-bedroom apartments and ALL UTILITIES ARE INCLUDED! Lakeview Tower Apartments, beyond your expectations but well within your means! Offering beautiful studio and one-bedroom apartments for people with disabilities or those 62 and better. Our community is located in Winter Haven, Florida on Lake Howard, a

  745 Avenue A SW, Winter Haven, FL 33880
• 

  /2

  $265,000 Sold Mar 04, 2025

  2928 Dayton Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft
  • Built 2006

  Last Sold Summary

  • 12% Below List Price
  • $137/SF
  • 143 Days On Market

  Current Estimated Value $282,104

  Last Listing Agent Calvin & Rondra Bolden LPT REALTY, LLC

  2928 Dayton Dr, Winter Haven, FL 33884
• 

  

  /19

  Est $266,271 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,333 Sq Ft

  1277 Haines Dr, Winter Haven, FL 33881

  1277 Haines Dr, Winter Haven, FL 33881
• 

  

  /49

  $302,250

  • 4 Beds
  • 2 Baths
  • 2,223 Sq Ft

  31 Lake Link Cir SE, Winter Haven, FL 33884

  Short Sale. Welcome Home to Comfort, Charm, and Endless Possibilities! Don’t miss the opportunity to own this spacious 4-bedroom, 2-bathroom home with over 2,200 square feet of living space—PLUS a converted garage that adds even more flexibility to your floor plan! Thoughtfully maintained and tastefully updated, this home offers a unique blend of modern upgrades and classic charm, all set on a

  

  Katie Sweet

  WATSON REALTY CORP.

  (863) 265-5379

  31 Lake Link Cir SE, Winter Haven, FL 33884
• 

  

  /16

  $1,910 per month

  • 3 Beds
  • 3 Baths
  • 1,516 Sq Ft
  • House for Rent

  834 Cinnamon Dr, Winter Haven, FL 33880

  This pet-friendly home features modern finishes and a functional layout with ample kitchen storage, spacious living areas, and abundant natural light throughout. The private yard offers space suitable for gardening or outdoor relaxation. Conveniently located near schools, parks, dining, and local amenities. Technology-enabled maintenance services provide added convenience, and self-touring is

  Daniel Reyes MAIN STREET RENEWAL LLC

  834 Cinnamon Dr, Winter Haven, FL 33880
• 

  

  /25

  $299,990 Sold Aug 04, 2025

  • 1,426 Sq Ft
  • $210/SF

  • 3 Beds
  • 2 Baths
  • Built 2025

  3335 Twilight Rd, Winter Haven, FL 33881

  From the front porch, you enter into the foyer and are immediately welcomed into the open family room, dining area, and kitchen. Just off the kitchen is the primary bedroom, which includes a primary bath, walk-in closet, and convenient access to the laundry room. The family room opens to a back patio, perfect for outdoor relaxation. On the opposite side of the kitchen, you’ll find two additional

  Starlight Homes

  3335 Twilight Rd, Winter Haven, FL 33881
• 

  /2

  Not Listed For Sale

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

  3008 Thornhill Rd, Winter Haven, FL 33880

  3008 Thornhill Rd, Winter Haven, FL 33880

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