Winter Haven, FL Homes

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  $424,990 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,182 Sq Ft

  Gabriela Plan at VillaMar, Winter Haven, FL 33884

  Prepare to be impressed by the Gabriela, a stunning two-story 5-bedroom, 3.5-bathroom home with a 3-car tandem garage. The inviting exterior and professionally designed landscaping exudes curb appeal. Once you're inside, you'll find a den space and half bathroom off the foyer, offering a private office or flex space. A secluded guest suite with a walk-in closet is also conveniently located on the

  Casa Fresca Homes Builder

  6614 Crescent Loop Unit 37807417, Winter Haven, FL 33884
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  $1,295 per month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  320 Spirit Landings Cir, Winter Haven, FL 33880

  Fully furnished 1-bedroom apartment available for immediate occupancy. Rent includes all utilities electric, water, internet, and trash providing a truly hassle-free living experience. Well-maintained unit featuring comfortable furnishings, a functional layout, and abundant natural light. Ideal for professionals, traveling nurses, or anyone seeking a turnkey rental. Conveniently located near

  Laura Medina Ruiz RE/MAX HERITAGE PROFESSIONALS

  320 Spirit Landings Cir, Winter Haven, FL 33880
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  $324,990 Sold Nov 27, 2025

  3251 Nightfall Rd, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,761 Sq Ft
  • Built 2025

  Last Sold Summary

  • $185/SF
  • 20 Days On Market

  Current Estimated Value $337,355

  Last Listing Agent Reed Williams ASHTON WOODS FLORIDA REALTY LLC

  3251 Nightfall Rd, Winter Haven, FL 33881
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  Not Listed For Sale

  208 Maple St, Winter Haven, FL 33880

  208 Maple St, Winter Haven, FL 33880

  Last Sold Summary

  • 0 Days On Market

  Last Sold Price $23,000

  Last Listing Agent Mabel Vega Negron LA ROSA REALTY CW PROPERTIES L
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  $355,999 Pending

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

  6002 Navona Way, 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

  6002 Navona Way, Winter Haven, FL 33884
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  /15

  $1,945 per month

  • 4 Beds
  • 2 Baths
  • 1,874 Sq Ft
  • House for Rent

  930 Deming Dr, 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,

  930 Deming Dr, Winter Haven, FL 33880
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  $82,500 Sold May 22, 2025

  517 Cipres Cir, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,101 Sq Ft
  • Built 1998

  Last Sold Summary

  • 10% Above List Price
  • $75/SF
  • 111 Days On Market

  Current Estimated Value $215,954

  Last Listing Agent David Small KELLER WILLIAMS REALTY SMART 1

  517 Cipres Cir, Winter Haven, FL 33880
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  Not Listed For Sale

  30 Flamingo Blvd, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1976

  30 Flamingo Blvd, Winter Haven, FL 33880

  Last Sold Summary

  • $81/SF
  • 28 Days On Market

  Last Sold Price $78,000

  Last Listing Agent Ashley Parkinson KELLER WILLIAMS REALTY SMART 1
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  /15

  $311,950 New Construction

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft

  Ruby Plan at Annabelle Estates, Lake Wales, FL 33859

  The single-story Ruby plan was designed for entertaining, offering a generous great room, an open dining area and a relaxing covered patio. You'll also appreciate an impressive kitchen with a center island and a walk-in pantry, as well as a lavish primary suite with a private bath and an immense walk-in closet. This home will be built with either two secondary bedrooms and a study or three

  Richmond American Homes Builder

  4130 Old Bartow Lake Wales Rd Unit 36431535, Lake Wales, FL 33859
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  $2,250 per month

  • 4 Beds
  • 2 Baths
  • 1,811 Sq Ft
  • House for Rent

  5465 San Pietro Dr, Winter Haven, FL 33884

  Be the first to live in this brand new 4 bedroom, 2 bath home located in the highly desirable Villa Mar community in Winter Haven. Featuring 1,811 sq ft of thoughtfully designed living space with an open-concept floor plan, this home is perfect for modern family living or entertaining guests. The spacious kitchen showcases contemporary finishes, ample cabinetry, and an island that flows into the

  Veronica Martinez MY REALTY GROUP, LLC.

  5465 San Pietro Dr, Winter Haven, FL 33884
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  $334,970 Sold Jul 10, 2025

  3158 Laurel Oak Ln, Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 2,005 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $167/SF
  • 1 Day On Market

  Current Estimated Value $339,551

  Last Listing Agent George Lindsey, III CAMBRIDGE REALTY OF CENTRAL FL

  3158 Laurel Oak Ln, Winter Haven, FL 33884
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  Not Listed For Sale

  235 6th St NW Unit 207, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 857 Sq Ft
  • Built 1982

  235 6th St NW Unit 207, Winter Haven, FL 33881

  Last Sold Summary

  • $176/SF
  • 97 Days On Market

  Last Sold Price $151,000

  Last Listing Agent April Spaulding LPT REALTY, LLC
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  $1,015,000

  • Land
  • 4.83 Acres
  • $210,145 per Acre

  0 Recker Hwy Unit 25572387, Winter Haven, FL 33880

  Presenting a rare opportunity to acquire up to 4.83 acres of strategically positioned, BPC-2 zoned land along Recker Highway in the heart of Winter Havens rapidly growing industrial and logistics corridor. Offered as a full assemblage or as individual parcels, each lot provides flexible development potential for business park, flex-industrial, or light manufacturing uses under Polk Countys

  Saunders Estate Saunders Land

  0 Recker Hwy Unit 25572387, Winter Haven, FL 33880
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  /20

  $2,775 per month

  • 6 Beds
  • 4.5 Baths
  • 3,920 Sq Ft
  • House for Rent

  356 Fish Hawk Dr, Winter Haven, FL 33884

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2919.90. That covers your base rent, $2775.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  356 Fish Hawk Dr, Winter Haven, FL 33884
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  $620,000 Sold Apr 14, 2026

  4310 Shadow Wood Trail, Winter Haven, FL 33880

  • 3 Beds
  • 4 Baths
  • 3,051 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $203/SF
  • 48 Days On Market

  Current Estimated Value $630,229

  Last Listing Agent MaryAnn Bartlett NEX REALTY

  4310 Shadow Wood Trail, Winter Haven, FL 33880
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  Est $329,680 Not Listed For Sale

  6087 Grey Heron Dr, Winter Haven, FL 33881

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft
  • Built 2017

  6087 Grey Heron Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 2% Below List Price
  • $130/SF
  • 289 Days On Market

  Last Sold Price $338,000

  Last Listing Agent Oscar Medina Garcia LA ROSA REALTY KISSIMMEE
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  $925,000

  • Land
  • 4.16 Acres
  • $222,356 per Acre

  5637 Recker Hwy, Winter Haven, FL 33880

  Presenting a rare opportunity to acquire up to 4.16 acres of strategically positioned, BPC-2 zoned land along Recker Highway in the heart of Winter Havens rapidly growing industrial and logistics corridor. Offered as a full assemblage or as individual parcels, each lot provides flexible development potential for business park, flex-industrial, or light manufacturing uses under Polk Countys

  Saunders Estate Saunders Land

  5637 Recker Hwy, Winter Haven, FL 33880
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  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Apartment for Rent

  118 Oak Crest Dr NW, Winter Haven, FL 33881

  HALF OFF FIRST MONTHS RENT! Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday

  David Small KELLER WILLIAMS REALTY SMART 1

  118 Oak Crest Dr NW, Winter Haven, FL 33881
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  $290,000 Sold Feb 18, 2026

  4525 Ashford Dr, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 2,434 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Below List Price
  • $119/SF
  • 24 Days On Market

  Current Estimated Value $302,437

  Last Listing Agent Clarisa Moody MARZUCCO REAL ESTATE

  4525 Ashford Dr, Winter Haven, FL 33880
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  Not Listed For Sale

  3000 Thornhill Rd, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1999

  3000 Thornhill Rd, Winter Haven, FL 33880

  Last Sold Summary

  • $159/SF
  • 50 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Melissa Minck LPT REALTY, LLC
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  $760,000

  • Land
  • 3.62 Acres
  • $209,945 per Acre

  0 Recker Hwy Unit 25572359, Winter Haven, FL 33880

  Presenting a rare opportunity to acquire up to 3.62 acres of strategically positioned, BPC-2 zoned land along Recker Highway in the heart of Winter Havens rapidly growing industrial and logistics corridor. Offered as a full assemblage or as individual parcels, each lot provides flexible development potential for business park, flex-industrial, or light manufacturing uses under Polk Countys

  Saunders Estate Saunders Land

  0 Recker Hwy Unit 25572359, Winter Haven, FL 33880
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  $1,780 per month

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • House for Rent

  3320 Timberline Rd W, Winter Haven, FL 33880

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  3320 Timberline Rd W, Winter Haven, FL 33880
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  $307,500 Sold Jun 25, 2025

  4924 Saint James St, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft
  • Built 2018

  Last Sold Summary

  • 7% Below List Price
  • $154/SF
  • 88 Days On Market

  Current Estimated Value $314,739

  Last Listing Agent Mathias Jenniges IAD FLORIDA LLC

  4924 Saint James St, Winter Haven, FL 33881
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  Not Listed For Sale

  503 Village Cir SW, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft
  • Built 1988

  503 Village Cir SW, Winter Haven, FL 33880

  Last Sold Summary

  • $129/SF
  • 40 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Carolyn Christian DALTON WADE INC
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  $359,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,227 Sq Ft

  Naples Plan at Willowbrook North, Winter Haven, FL 33881

  NAPLES: Beautiful 2 Level, 2 Car Garage Home with Open Concept Living, Loft and up to 5 Bedrooms! The Naples plan is available in Coastal, Farmhouse or Traditional exterior designs. The inviting front porch opens to a gracious foyer with adjacent powder room. The well-appointed, island kitchen is open to the adjoining cafe and spacious family room. . The primary suite boasts an en suite bathroom

  DRB Homes Builder

  0 Fl-544 St Unit 36849116, Winter Haven, FL 33881
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  /22

  $2,030 per month

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • House for Rent

  2122 Chris Dr, Winter Haven, FL 33884

  Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2122 Chris Dr, Winter Haven, FL 33884
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  $275,490 Sold Jan 28, 2026

  4157 Giorgio Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $183/SF
  • 35 Days On Market

  Current Estimated Value $246,667

  D.R. Horton VillaMar

  4157 Giorgio Dr, Winter Haven, FL 33884
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  Not Listed For Sale

  6459 Hollyberry Ln NE, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1987

  6459 Hollyberry Ln NE, Winter Haven, FL 33881

  Last Sold Summary

  • $133/SF
  • 120 Days On Market

  Last Sold Price $134,800

  Last Listing Agent Larry Hilton RE/MAX
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  $434,900

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  240 Santa Rosa Dr, Winter Haven, FL 33884

  *** Motivated seller! Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! *** Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the

  Brian Surrency LIVE FLORIDA REALTY

  240 Santa Rosa Dr, Winter Haven, FL 33884
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  $2,340 per month

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  2973 Whispering Trails Dr, Winter Haven, FL 33884

  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

  2973 Whispering Trails Dr, Winter Haven, FL 33884
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  $232,000 Sold Oct 21, 2025

  3118 Walnut St, Winter Haven, FL 33881

  • 3 Beds
  • 1 Bath
  • 1,013 Sq Ft
  • Built 1955

  Last Sold Summary

  • 1% Below List Price
  • $229/SF
  • 99 Days On Market

  Current Estimated Value $221,978

  Last Listing Agent Kathi Zerilli REDFIN CORPORATION

  3118 Walnut St, Winter Haven, FL 33881
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  Est $317,991 Not Listed For Sale

  868 Buccaneer Blvd, Winter Haven, FL 33880

  • 3 Beds
  • 3 Baths
  • 2,190 Sq Ft
  • Built 2013

  868 Buccaneer Blvd, Winter Haven, FL 33880

  Last Sold Summary

  • 3% Above List Price
  • $142/SF
  • 257 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Brandy Duncan COLDWELL BANKER REALTY
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  $317,000

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  129 Morning Glory Cir, Winter Haven, FL 33884

  Welcome to this well-maintained 3-bedroom, 2-bath home with a 2-car garage, offering just under 1,900 square feet of comfortable living space. Built in 2002 and topped with a long-lasting, low-maintenance tile roof designed for lasting durability, this home is ideally positioned with no direct neighbors—backing up to peaceful green space for added privacy. This property has been thoughtfully

  Laurie Nock LPT REALTY, LLC

  129 Morning Glory Cir, Winter Haven, FL 33884
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  $2,220 per month

  • 5 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • House for Rent

  2134 Chris Dr, Winter Haven, FL 33884

  Brand New Two-Story Home for Rent in Winter Haven Welcome to this stunning brand new two-story home located in the heart of Winter Haven, offering the perfect combination of space, style, and convenience. Designed with modern living in mind, this beautiful property is ideal for families or anyone looking for comfort and quality in a prime location. The home features 5 spacious bedrooms, including

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2134 Chris Dr, Winter Haven, FL 33884
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  $229,000 Sold Jul 15, 2025

  4174 Pirates Landing, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 1985

  Last Sold Summary

  • 5% Below List Price
  • $172/SF
  • 91 Days On Market

  Current Estimated Value $230,180

  Last Listing Agent Jill Lingenfelter CENTURY 21 MYERS REALTY

  4174 Pirates Landing, Winter Haven, FL 33884
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  Not Listed For Sale

  Unlisted Address

  • 2 Beds
  • 2 Baths
  • 1,075 Sq Ft
  • Built 1987

  Unlisted Address

  Last Sold Summary

  • $102/SF
  • 76 Days On Market

  Last Sold Price $110,000

  Last Listing Agent Bob Hayes FLORIDA FIRST REALTY INC
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  $479,000

  • 4 Beds
  • 3 Baths
  • 2,569 Sq Ft

  305 Hernando Rd, Winter Haven, FL 33884

  Listing price reduced!!! Enjoy the quaint living in this deed restricted community! Step into this stunning home through a spacious, light-filled foyer and prepare to be impressed by the thoughtfully, well maintained designed layout and exceptional features throughout. This home offers oversized bedrooms and a versatile bonus room—perfect for a game room, home office, or even a private in-law

  Sherry Sapp COLDWELL BANKER REALTY

  305 Hernando Rd, Winter Haven, FL 33884
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  $2,295 per month

  • 4 Beds
  • 2 Baths
  • 1,730 Sq Ft
  • House for Rent

  331 Columbo St, Winter Haven, FL 33880

  We are currently making final preparations for this home to be available. 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

  331 Columbo St, Winter Haven, FL 33880
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  $150,000 Sold Apr 29, 2025

  1810 Woodpointe Dr, Winter Haven, FL 33884

  • Land
  • 0.44 Acre
  • $340,909 per Acre

  Last Sold Summary

  • 1,011 Days On Market

  Current Estimated Value $167,233

  Last Listing Agent John Wood, JR JOHN WOOD REALTY, INC.

  1810 Woodpointe Dr, Winter Haven, FL 33884
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  Not Listed For Sale

  6328 Grove Pointe Dr SE, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 2002

  6328 Grove Pointe Dr SE, Winter Haven, FL 33884

  Last Sold Summary

  • $128/SF
  • 64 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Nicole Ash BHHS FLORIDA PROPERTIES GROUP

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