Winter Haven, FL Homes

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  /47

  $485,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,221 Sq Ft

  404 Talamone Dr, Winter Haven, FL 33884

  BACK ON MARKET DUE TO BUYERS FAILED FINANCING!! MAGNIFICENT 4BR/3BA POOL HOME!! Located in the gated Winter Haven subdivision of Tuscanny, this exquisitely maintained one story home, with approx. 3,242 sqft including an air conditioned sunroom, has so much to offer; it showcases a full GUEST SUITE and a new roof as of April 2021! Fantastic Features include: crown molding, ceramic tile, laminate

  Marissa Taranto EXP REALTY LLC

  404 Talamone Dr, Winter Haven, FL 33884
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  /21

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Condo for Rent

  361 Winter Ridge Blvd Unit 361, Winter Haven, FL 33881

  AVAILABLE UNFURNISHED CONDO FOR RENT AT THE CHAIN OF LAKES Community of Winter Ridge Condominiums between Lake Smart and Lake Conine! This corner unit property offers stunning views across Lake Smart and the canal to Lake Conine. The master ensuite offers access to the porch with view to enjoy the panorama of the canal and Lake Smart. This spacious bedroom provides a large walk-in closet with

  Alvaro Molina TWIN HOMES REALTY

  361 Winter Ridge Blvd Unit 361, Winter Haven, FL 33881
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  /2

  $312,000 Sold Mar 06, 2026

  499 Highfin Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,983 Sq Ft
  • Built 2021

  Last Sold Summary

  • 4% Below List Price
  • $157/SF
  • 37 Days On Market

  Current Estimated Value $307,998

  Last Listing Agent Melissa Witter KELLER WILLIAMS REALTY SMART 1

  499 Highfin Dr, Winter Haven, FL 33881
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  /52

  Est $317,091 Not Listed For Sale

  208 Fall Glo Rd, Winter Haven, FL 33880

  • 4 Beds
  • 3 Baths
  • 2,526 Sq Ft
  • Built 2018

  208 Fall Glo Rd, Winter Haven, FL 33880

  Last Sold Summary

  • 1% Above List Price
  • $125/SF
  • 68 Days On Market

  Last Sold Price $314,500

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
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  /33

  $299,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,938 Sq Ft

  244 Meredith Blvd, Winter Haven, FL 33881

  The Mulberry floor plan epitomizes the charm of single-story living with its spacious and versatile layout, perfectly crafted for the modern single-family lifestyle. Spread across 1,938 square feet, this home offers ample room for comfort and functionality. Featuring four bedrooms and two and a half bathrooms, including a luxurious master suite, residents enjoy privacy and relaxation in every

  Dream Finders Homes Builder

  244 Meredith Blvd, Winter Haven, FL 33881
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  /17

  $1,299 per month

  • 2 Beds
  • 1 Bath
  • 762 Sq Ft
  • Condo for Rent

  3060 St Paul Dr, Jan Phyl Village, FL 33880

  This cozy 2-bedroom, 1-bathroom apartment offers 761.5 square feet of comfortable living space. Enjoy modern conveniences in a practical layout.- Electric range, dishwasher, microwave, and refrigerator included- Garbage disposal for convenience- Efficient forced air heating and central cooling system- Durable tile flooring- Washer and dryer hookups for easy laundry

  3060 St Paul Dr, Jan Phyl Village, FL 33880
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  /2

  $275,000 Sold Oct 15, 2025

  701 Reflections Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 2001

  Last Sold Summary

  • $185/SF
  • 13 Days On Market

  Current Estimated Value $272,592

  Last Listing Agent Hailey Cornell REAL BROKER, LLC

  701 Reflections Dr, Winter Haven, FL 33884
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  /18

  Est $335,580 Not Listed For Sale

  4253 Roberta Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft
  • Built 2018

  4253 Roberta Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 2% Above List Price
  • $132/SF
  • 36 Days On Market

  Last Sold Price $330,000

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
• 

  

  /27

  $307,490 New Construction

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  CALI Plan at VillaMar, Winter Haven, FL 33884

  Introducing the Cali floorplan at Villamar, in Winter Haven, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,828 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and tile floors throughout. As you step inside,

  D.R. Horton Builder

  3744 Giorgio Dr Unit 36202851, Winter Haven, FL 33884
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  /8

  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • House for Rent

  855 Turner Ln, Winter Haven, FL 33884

  Amazing location! In this beautiful house you will find a 3 bedroom 2 full bath and a bonus room (use it as an extra bedroom, office, etc.) This modern house sits on a corner lot, spacious living area, very sunny and inviting, ceramic tiles, stainless steal appliances, quartz counter tops, walking closet and a 2 car garage. Call to schedule a showing and move in to this lovely community.

  Britzeida Pichardo LA ROSA REALTY CENTRAL FLORIDA LLC

  855 Turner Ln, Winter Haven, FL 33884
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  /2

  $251,962 Sold Mar 30, 2026

  1201 5th St NE, Winter Haven, FL 33881

  • 4 Beds
  • 3 Baths
  • 2,040 Sq Ft
  • Built 1945

  Last Sold Summary

  • 8% Below List Price
  • $124/SF
  • 10 Days On Market

  Last Listing Agent George Waller, JR BTW PROPERTIES OF LAKELAND

  1201 5th St NE, Winter Haven, FL 33881
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  /2

  Est $276,657 Not Listed For Sale

  5732 Lakeside Landings Blvd, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,748 Sq Ft
  • Built 2018

  5732 Lakeside Landings Blvd, Winter Haven, FL 33881

  Last Sold Summary

  • 1% Below List Price
  • $160/SF
  • 55 Days On Market

  Last Sold Price $280,000

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
• 

  

  /20

  $394,999 Pending

  • 5 Beds
  • 3 Baths
  • 2,892 Sq Ft

  5429 San Pietro Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept

  Dale Human CASA FRESCA REALTY

  5429 San Pietro Dr, Winter Haven, FL 33884
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  /19

  $2,015 per month

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • House for Rent

  344 Sand Pine Trail, Winter Haven, FL 33880

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

  344 Sand Pine Trail, Winter Haven, FL 33880
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  /21

  $319,990 Sold Dec 24, 2025

  6420 Domizio Dr, Winter Haven, FL 33884

  • 5 Beds
  • 2 Baths
  • 2,326 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $138/SF
  • 23 Days On Market

  Current Estimated Value $327,667

  Lennar VillaMar

  6420 Domizio Dr, Winter Haven, FL 33884
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  /34

  Est $290,058 Not Listed For Sale

  3034 Royal Tern Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • Built 2018

  3034 Royal Tern Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 7% Below List Price
  • $168/SF
  • 6 Days On Market

  Last Sold Price $311,000

  Last Listing Agent Idaris Morales Sierra, PA AXEN REALTY, LLC
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  /34

  $209,000

  • 3 Beds
  • 1 Bath
  • 1,190 Sq Ft

  104 Avenue K NE, Winter Haven, FL 33881

  SELLER MOTIVATED. MAKE OFFER! Looking for an affordable, move-in ready home under $250k with a fenced yard and no HOA in central Winter Haven? This updated 3-bedroom, 1-bath concrete block home offers 1,191+ square feet of easy living—plus a bright Florida bonus room and a private backyard that's fully fenced, perfect for pets, gardening, or relaxing outdoors. Inside, you'll find a modern kitchen

  April Spaulding LPT REALTY, LLC

  104 Avenue K NE, Winter Haven, FL 33881
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  /8

  $1,200 per month

  • 1 Bed
  • 1 Bath
  • 507 Sq Ft
  • Townhouse for Rent

  103 4th St SE Unit B, Winter Haven, FL 33880

  Cozy and updated 1 bedroom, 1 bathroom apartment located in the heart of Winter Haven, FL, just minutes from downtown shopping, dining, and the Chain of Lakes. This charming unit offers a bright living space, comfortable bedroom, and convenient access to local parks, restaurants, and major roadways. Perfect for anyone looking for comfortable living in a great location.

  Pedro Cartagena 1513 REALTY LLC

  103 4th St SE Unit B, Winter Haven, FL 33880
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  /11

  $259,490 Sold Aug 20, 2025

  2199 Chris Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $182/SF
  • 19 Days On Market

  Current Estimated Value $285,813

  Lennar Peace Creek Reserve - Manor Key Collection

  2199 Chris Dr, Winter Haven, FL 33884
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  /17

  Est $217,900 Not Listed For Sale

  3004 Caneel St, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,521 Sq Ft
  • Built 2018

  3004 Caneel St, Winter Haven, FL 33884

  Last Sold Summary

  • 5% Below List Price
  • $151/SF
  • 47 Days On Market

  Last Sold Price $230,000

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
• 

  

  /25

  $354,999 Pending

  • 5 Beds
  • 3 Baths
  • 2,470 Sq Ft

  5389 San Pietro Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Check out the Indigo, a spacious two-story, 5-bedroom, 3-bathroom, 2-car garage home perfect for growing families or hosting guests. Enter the impressive foyer with soaring ceilings that creates an immediate sense of openness. From the foyer, the home effortlessly

  Dale Human CASA FRESCA REALTY

  5389 San Pietro Dr, Winter Haven, FL 33884
• 

  

  /15

  $2,100 per month

  • 4 Beds
  • 2 Baths
  • 1,938 Sq Ft
  • House for Rent

  159 Southern Breeze Lp, Winter Haven, FL 33880

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  159 Southern Breeze Lp, Winter Haven, FL 33880
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  /7

  $234,990 Sold Jan 30, 2026

  223 Turtle Bay Ave, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $147/SF
  • 7 Days On Market

  Current Estimated Value $260,139

  Highland Homes Harbor at Lake Henry - Townhomes

  223 Turtle Bay Ave, Winter Haven, FL 33881
• 

  

  /17

  Est $460,635 Not Listed For Sale

  5764 E County Road 542, Winter Haven, FL 33880

  • 6 Beds
  • 3 Baths
  • 2,592 Sq Ft
  • Built 1980

  5764 E County Road 542, Winter Haven, FL 33880

  Last Sold Summary

  • 8% Above List Price
  • $165/SF
  • 41 Days On Market

  Last Sold Price $427,000

  Last Listing Agent Marcy Smiley Theobald IRON VALLEY REAL ESTATE OSCEOLA
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  /77

  $585,000

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

  6261 Pinehurst Loop, Winter Haven, FL 33884

  Live the lifestyle you’ve been dreaming about in Lake Ashton, Winter Haven’s premier 55+ gated community. This beautifully cared-for Ashton floor plan offers 3 bedrooms, 2 baths, a den, and 2,512 sq ft of thoughtfully designed space — but it’s the feeling of this home that truly stands out. From the manicured landscaping to the elegant leaded-glass French front doors, every detail reflects pride

  Anita Lowe LOCKHART & ASSOCIATES INC

  6261 Pinehurst Loop, Winter Haven, FL 33884
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  /14

  $2,150 per month

  • 4 Beds
  • 2 Baths
  • 1,462 Sq Ft
  • House for Rent

  258 Meadowbrook Blvd, Winter Haven, FL 33881

  Beautiful 4-bedroom, 2-bathroom home located in the heart of Winter Haven. This home features ceramic tile flooring throughout the main living areas and a spacious great room with a modern built-in TV wall and electric fireplace. Enjoy peaceful views of the reserve from this premium lot. The master suite offers a spacious walk-in closet and an upgraded shower with a glass door. All bedrooms

  Ruth Romero LA ROSA REALTY INTERNACIONAL L

  258 Meadowbrook Blvd, Winter Haven, FL 33881
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  /2

  $370,000 Sold Jan 05, 2026

  2004 Leisure Dr, Winter Haven, FL 33881

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft
  • Built 1978

  Last Sold Summary

  • $160/SF
  • 5 Days On Market

  Current Estimated Value $366,596

  Last Listing Agent Jill Aubin RE/MAX REALTY UNLIMITED

  2004 Leisure Dr, Winter Haven, FL 33881
• 

  /2

  Est $332,968 Not Listed For Sale

  543 Squires Grove Dr, Winter Haven, FL 33880

  • 4 Beds
  • 3 Baths
  • 2,526 Sq Ft
  • Built 2018

  543 Squires Grove Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 5% Above List Price
  • $126/SF
  • 135 Days On Market

  Last Sold Price $318,000

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1
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  /70

  $369,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,334 Sq Ft

  Ponte Vedra Plan at Willowbrook North, Winter Haven, FL 33881

  PONTE VEDRA: Beautiful 2 Level, 2 Car Garage Home with Open Concept Living , Loft and up to 5 Bedrooms! The Ponte Vedra plan is available in Coastal, Farmhouse or Traditional exterior designs. The gracious foyer leads to the cafe area and the well-appointed island kitchen that overlooks the spacious family room. The 2nd level primary suite boasts an en suite bathroom with dual sink vanity,

  DRB Homes Builder

  0 Fl-544 St Unit 36849126, Winter Haven, FL 33881
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  /20

  $2,010 per month

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft
  • House for Rent

  104 Lake Daisy Terrace, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  104 Lake Daisy Terrace, Winter Haven, FL 33884
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  /2

  $380,000 Sold Feb 27, 2026

  168 Morning Glory Cir, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,894 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $201/SF
  • 64 Days On Market

  Current Estimated Value $377,351

  Last Listing Agent Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  168 Morning Glory Cir, Winter Haven, FL 33884
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  /2

  Est $294,040 Not Listed For Sale

  548 Lucerne Blvd, Winter Haven, FL 33881

  • 4 Beds
  • 2.5 Baths
  • 1,956 Sq Ft
  • Built 2018

  548 Lucerne Blvd, Winter Haven, FL 33881

  Last Sold Summary

  • 2% Below List Price
  • $153/SF
  • 154 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Michael Cruz Irizarry LPT REALTY, LLC
• 

  

  /21

  $281,999 Open Sat 10AM - 6PM

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft

  6056 Navona Way, Winter Haven, FL 33884

  BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new

  Dale Human CASA FRESCA REALTY

  6056 Navona Way, Winter Haven, FL 33884
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  /41

  $1,695 per month

  • 2 Beds
  • 2.5 Baths
  • 1,184 Sq Ft
  • Townhouse for Rent

  2500 21st St NW Unit 31, Winter Haven, FL 33881

  Modern 2-Bed, 2.5-Bath Townhome in Desirable Casa del Sol... Step into comfort and convenience in this beautifully designed two-story end unit townhome, perfect for professionals seeking a stylish, low-maintenance lifestyle. Downstairs Living: Formal living room ideal for relaxing or entertaining, Convenient guest half bath, Bright kitchen featuring refrigerator, range, microwave, dishwasher, and

  Dorothea Bogert FL REALTY

  2500 21st St NW Unit 31, Winter Haven, FL 33881
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  /2

  $425,000 Sold Oct 29, 2025

  232 Terranova Blvd, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 2,327 Sq Ft
  • Built 2004

  Last Sold Summary

  • $183/SF
  • 2 Days On Market

  Current Estimated Value $418,140

  Last Listing Agent Deanna Stone THE STONES REAL ESTATE FIRM

  232 Terranova Blvd, Winter Haven, FL 33884
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  /2

  Est $340,587 Not Listed For Sale

  3021 Royal Tern Dr, Winter Haven, FL 33881

  • 5 Beds
  • 3 Baths
  • 2,616 Sq Ft
  • Built 2018

  3021 Royal Tern Dr, Winter Haven, FL 33881

  Last Sold Summary

  • $131/SF
  • 192 Days On Market

  Last Sold Price $342,000

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP
• 

  

  /3

  $344,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,226 Sq Ft

  Azure Plan at VillaMar, Winter Haven, FL 33884

  Welcome to The Azure, where modern design meets practical living in a home that has it all. With 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home is crafted for comfort and style. The extraordinary elevation and professionally designed landscaping create a captivating first impression. Step through the front door to discover luxurious vinyl plank flooring that extends throughout the

  Casa Fresca Homes Builder

  5512 Taverna Loop Unit 40026132, Winter Haven, FL 33884
• 

  

  /17

  $1,745 per month

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • House for Rent

  1405 N Lake Shipp Dr SW, Winter Haven, FL 33880

  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, relaxing, or gardening!Take advantage of the incredible location,

  1405 N Lake Shipp Dr SW, Winter Haven, FL 33880
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  /2

  $98,000 Sold Jul 30, 2025

  4201 Cedarwood Dr, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1979

  Last Sold Summary

  • 25% Below List Price
  • $85/SF
  • 243 Days On Market

  Last Listing Agent Kathy Devor COLDWELL BANKER REALTY

  4201 Cedarwood Dr, Winter Haven, FL 33880
• 

  

  /41

  Est $288,249 Not Listed For Sale

  2185 Rose Blvd, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • Built 2018

  2185 Rose Blvd, Winter Haven, FL 33881

  Last Sold Summary

  • 1% Above List Price
  • $154/SF
  • 49 Days On Market

  Last Sold Price $285,000

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

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