Winter Haven, FL Homes

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  $434,900

  • Land
  • 1.57 Acres
  • $277,006 per Acre

  1530 11th St NE, Winter Haven, FL 33881

  Entitled land! 14 Unit townhome development approved and ready for construction immediately! 1.57 acres consisting of 103 feet of lake frontage on Lake Buckeye in Winter Haven. Documents will be provided upon requests.

  Chandler Williams

  EXIT REALTY PREMIER LEGACY

  (863) 563-2453

  1530 11th St NE, Winter Haven, FL 33881
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  /21

  $1,450 per month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Condo for Rent

  1707 Eagle Pond Dr, Winter Haven, FL 33884

  MOVE-IN READY upstairs Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium includes interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite bathroom while both bedrooms offer walk-in closets. Additional linen storage exists in the main

  Kayly Malinas JOHN WOOD REALTY, INC.

  1707 Eagle Pond Dr, Winter Haven, FL 33884
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  /23

  $329,990 Sold May 12, 2025

  1799 Teagan Ln, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,451 Sq Ft
  • Built 2025

  Last Sold Summary

  • 14% Below List Price
  • $135/SF
  • 77 Days On Market

  Current Estimated Value $337,173

  Last Listing Agent Ben Goldstein LENNAR REALTY

  1799 Teagan Ln, Winter Haven, FL 33884
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  Est $219,960 Not Listed For Sale

  128 Stevenson Rd, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft
  • Built 1962

  128 Stevenson Rd, Winter Haven, FL 33884

  Last Sold Summary

  • $162/SF
  • 68 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Keith St. Onge LA ROSA REALTY PRESTIGE
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  /21

  $59,900

  • 2 Beds
  • 1 Bath
  • 248 Sq Ft

  7041 Fairview Village Cir, Winter Haven, FL 33881

  Welcome to Fairview Village, an active 55+ gated waterfront community in Winter Haven. This charming 2-bedroom home offers peaceful canal and lake views, with private access to the water between Lake Hamilton and Lake Henry—perfect for boating and fishing. The community features a 99-year land lease and a low HOA fee of just $90 per month, which includes water and sewer. Residents enjoy a heated

  

  Sandra Perry

  WATSON REALTY CORP.

  (863) 622-8934

  7041 Fairview Village Cir, Winter Haven, FL 33881
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  $1,850 per month

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • House for Rent

  206 Kingshill Ct SE, 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.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

  206 Kingshill Ct SE, Winter Haven, FL 33884
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  $284,000 Sold Dec 30, 2025

  232 Spirit Landing Cir, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,546 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $184/SF
  • 21 Days On Market

  Current Estimated Value $284,644

  Last Listing Agent Samuel Eckerson KELLER WILLIAMS ADVANTAGE REALTY

  232 Spirit Landing Cir, Winter Haven, FL 33880
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  Est $238,729 Not Listed For Sale

  1625 Avenue D NE, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,228 Sq Ft
  • Built 1958

  1625 Avenue D NE, Winter Haven, FL 33881

  Last Sold Summary

  • 8% Below List Price
  • $212/SF
  • 22 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Tommy Miller Jr. SUNCOAST REALTY SOLUTIONS, LLC
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  /23

  $224,000

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft

  713 Crestwood Dr, Winter Haven, FL 33881

  Solar-powered 3-bedroom home with NO HOA offers flexibility, efficiency, and a layout designed to fit today’s lifestyle. The front living room welcomes you with abundant natural light, creating a bright and inviting space for everyday living or entertaining. The home features both a living room and a separate family room, along with an eat-in kitchen that provides a comfortable space for casual

  

  Tony Baroni

  KELLER WILLIAMS SUBURBAN TAMPA

  (863) 356-0119

  713 Crestwood Dr, Winter Haven, FL 33881
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  /29

  $2,200 per month

  • 4 Beds
  • 3 Baths
  • 1,988 Sq Ft
  • House for Rent

  2772 San Marco Way, Winter Haven, FL 33884

  Welcome to the desirable Villamar community in Winter Haven, where comfort, convenience, and modern living come together in one of the area’s fastest-growing neighborhoods. This FULLY FENCED like-new 4-bedroom, 3-bathroom home offers a thoughtfully designed layout that perfectly balances functionality and style, making it ideal for families, entertaining, or simply enjoying everyday life.

  Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

  2772 San Marco Way, Winter Haven, FL 33884
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  $130,000 Sold Aug 27, 2025

  3651 Rifle Range Rd, Winter Haven, FL 33880

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $143/SF
  • 44 Days On Market

  Current Estimated Value $133,141

  Last Listing Agent David Fleming BHHS FLORIDA PROPERTIES GROUP

  3651 Rifle Range Rd, Winter Haven, FL 33880
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  Est $132,153 Not Listed For Sale

  232 26th St SW, Winter Haven, FL 33880

  • 3 Beds
  • 1 Bath
  • 888 Sq Ft
  • Built 1964

  232 26th St SW, Winter Haven, FL 33880

  Last Sold Summary

  • 10% Above List Price
  • $135/SF
  • 3 Days On Market

  Last Sold Price $120,000

  Last Listing Agent Brian Cox KELLER WILLIAMS REALTY SMART 1
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  /22

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,118 Sq Ft

  543 Terranova Cir, Winter Haven, FL 33884

  POOL Home on Pond in TERRANOVA! Located in desirable southeast Winter Haven, this home has it all! Large areas overlooking screened pool and pond frontage and views! Enjoy the security of a gated community close to schools, shopping, churches and LEGOLAND! Call for your private showing today!

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 356-0796

  543 Terranova Cir, Winter Haven, FL 33884
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  /11

  $1,700 per month

  • 3 Beds
  • 1 Bath
  • Condo for Rent

  2504 Ave O NW Unit A Upstairs, Winter Haven, FL 33881

  Property Id: 2366247Spacious 3 Bedroom 1 Bath with large open living / kitchen area. This unit is freshly painted and ready for its next family. This unit’s rent includes electricity and water! Fill out the free pre-screen to start the process. This one won’t last long.

  2504 Ave O NW Unit A Upstairs, Winter Haven, FL 33881
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  $305,046 Sold Mar 20, 2026

  2319 Brassie Ct, Winter Haven, FL 33884

  • 4 Beds
  • 2.5 Baths
  • 2,202 Sq Ft
  • Built 2025

  Last Sold Summary

  • 10% Below List Price
  • $139/SF
  • 124 Days On Market

  Current Estimated Value $325,706

  Last Listing Agent Claudia Gutierrez ADAMS HOMES REALTY

  2319 Brassie Ct, Winter Haven, FL 33884
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  Est $177,037 Not Listed For Sale

  129 El Dorado, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,011 Sq Ft
  • Built 1976

  129 El Dorado, Winter Haven, FL 33884

  Last Sold Summary

  • 1% Above List Price
  • $173/SF
  • 77 Days On Market

  Last Sold Price $175,000

  Last Listing Agent Travis Redder HARPER REALTY FL, LLC
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  $364,999 New Construction

  • 5 Beds
  • 3 Baths
  • 2,471 Sq Ft

  5457 San Pietro Dr, Winter Haven, FL 33884

  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 flows into the main living areas and kitchen. With quartz countertops throughout, stainless-steel appliances and a smart thermostat

  

  Casa Fresca Homes

  Builder

  5457 San Pietro Dr, Winter Haven, FL 33884
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  /22

  $1,817 per month

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • House for Rent

  3304 White Indigo Rd, Winter Haven, FL 33884

  WINTER HAVEN NEW BUILD 3 BED/2 BATH HOME FOR RENT! MOVE-IN SPECIAL!Priced Low, Call Now! Very Clean Property, Move-in Ready, 2 Car Garage, Brand New Build—First Tenancy! Huge Master Suite, Eat-In Kitchen, Corian Countertops, Upgraded Kitchen, Brand New Kitchen, Carpeted Bedrooms, Laminate Wood-Look Flooring, COMMUNITY Pool, COMMUNITY Playground, COMMUNITY Multiple Lakes, COMMUNITY Walking &

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  3304 White Indigo Rd, Winter Haven, FL 33884
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  $495,000 Sold Jan 09, 2026

  413 Horseshoe Ln NE, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 2,336 Sq Ft
  • Built 1991

  Last Sold Summary

  • 24% Below List Price
  • $212/SF
  • 132 Days On Market

  Current Estimated Value $479,767

  Last Listing Agent John Kelson KELLER WILLIAMS ADVANTAGE 2 REALTY

  413 Horseshoe Ln NE, Winter Haven, FL 33881
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  Est $243,527 Not Listed For Sale

  307 La Serena, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,389 Sq Ft
  • Built 1978

  307 La Serena, Winter Haven, FL 33884

  Last Sold Summary

  • 3% Below List Price
  • $180/SF
  • 125 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Nikki Casha ACROPOLIS REALTY GROUP LLC
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  /39

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,595 Sq Ft

  122 22nd St NW, Winter Haven, FL 33880

  Welcome to your dream oasis—a stunning craftsman-style 3-bedroom, 2-bath saltwater pool home nestled on just over a quarter acre. This charming property features a large front porch, perfect for relaxing with your morning coffee or enjoying beautiful sunsets. Step inside to find a warm and inviting interior with classic crown molding throughout. The formal dining room offers an elegant space for

  

  Michelle Howard

  KELLER WILLIAMS REALTY SMART 1

  (863) 270-4468

  122 22nd St NW, Winter Haven, FL 33880
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  /18

  $1,770 per month

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • House for Rent

  148 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

  148 Southern Breeze Lp, Winter Haven, FL 33880
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  $272,000 Sold Dec 15, 2025

  676 Augusta Rd, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $160/SF
  • 108 Days On Market

  Current Estimated Value $272,427

  Last Listing Agent Dee Norris NEXTHOME NORRIS & COMPANY REAL

  676 Augusta Rd, Winter Haven, FL 33884
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  Est $234,743 Not Listed For Sale

  753 Avenue O SE, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1961

  753 Avenue O SE, Winter Haven, FL 33880

  Last Sold Summary

  • 4% Below List Price
  • $169/SF
  • 20 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Eddie Collazo RE/MAX
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  /100

  $1,895,000

  • 4 Beds
  • 4 Baths
  • 4,708 Sq Ft

  13 Bogey Dr, Winter Haven, FL 33881

  Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist.The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends

  

  Brock Jennings

  THE MARKET REALTY COMPANY

  (863) 774-3952

  13 Bogey Dr, Winter Haven, FL 33881
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  /26

  $4,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,944 Sq Ft
  • House for Rent

  1787 Lake Hill Dr, Winter Haven, FL 33884

  Beautiful 4-bedroom/3.5-bathroom home with additional bonus room ideal for an office, den, gym, or play room in the prestigious Woodpointe community of SE Winter Haven! Elegant custom and designer finishes throughout, screened lanai, walk-in closets, open-concept and split-bedroom floor plan, and so much more. Applications evaluated on creditworthiness and income equal to at least 3x monthly rent

  Kayly Malinas JOHN WOOD REALTY, INC.

  1787 Lake Hill Dr, Winter Haven, FL 33884
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  /68

  $52,500 Sold May 08, 2025

  280 Putter Cir, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  Last Sold Summary

  • 34% Below List Price
  • $42/SF
  • 243 Days On Market

  Last Listing Agent Cynthia Cole Sunset Home Sales

  280 Putter Cir, Winter Haven, FL 33881
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  Est $296,976 Not Listed For Sale

  5341 Nicklaus Dr, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 2006

  5341 Nicklaus Dr, Winter Haven, FL 33884

  Last Sold Summary

  • 1% Below List Price
  • $196/SF
  • 41 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Lori Raath LAKE ASHTON REALTY INC.
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  /44

  $138,900

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  409 Village Cir SW, Winter Haven, FL 33880

  Charming and well maintained! 2-Bedroom 2- Bath Home in Desirable 55+ Community – You Own the Land with low HOA fees!This inviting home features fresh interior and exterior paint and a newly screened-in front porch, perfect for enjoying your morning coffee, afternoon tea or just relaxing in the Florida breeze. The property also offers a fenced-in backyard, ideal for pets to play or

  

  Michelle Armbruster

  LOCKHART & ASSOCIATES INC

  (863) 340-7516

  409 Village Cir SW, Winter Haven, FL 33880
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  /15

  $3,170 per month

  • 5 Beds
  • 3 Baths
  • 2,566 Sq Ft
  • House for Rent

  957 Gotthard Pass Dr, Winter Haven, FL 33881

  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

  957 Gotthard Pass Dr, Winter Haven, FL 33881
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  $669,000 Sold May 28, 2025

  6810 Crystal Beach Rd, Winter Haven, FL 33880

  • 4 Beds
  • 2.5 Baths
  • 3,414 Sq Ft
  • Built 1998

  Last Sold Summary

  • 19% Below List Price
  • $196/SF
  • 68 Days On Market

  Current Estimated Value $671,696

  Last Listing Agent Carri McLure LPT REALTY, LLC

  6810 Crystal Beach Rd, Winter Haven, FL 33880
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  Est $552,407 Not Listed For Sale

  2400 Crump Rd, Winter Haven, FL 33881

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

  2400 Crump Rd, Winter Haven, FL 33881

  Last Sold Summary

  • $255/SF
  • 36 Days On Market

  Last Sold Price $554,900

  Last Listing Agent Steven Smith, PA LOCKHART & ASSOCIATES INC
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  $459,000

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft

  148 Lake Otis Rd, Winter Haven, FL 33884

  Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level home offers a perfect blend of modern luxury and comfort. With a spacious layout, a private pool, and an abundance of natural light, this home is designed for both relaxation and entertaining. As you enter, you’ll immediately notice the bright and airy

  

  Michelle Armbruster

  LOCKHART & ASSOCIATES INC

  (863) 599-6261

  148 Lake Otis Rd, Winter Haven, FL 33884
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  $1,900 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • House for Rent

  227 Volusia Dr, Winter Haven, FL 33884

  Located in an established neighborhood this home offers 2 bedrooms and 2 bathrooms. Galley kitchen overlooking large fenced backyard. Inside laundry room and 2 car garage. Available and ready for immediate occupancy.

  Sue Ann Williamon THE HOME COMPANY

  227 Volusia Dr, Winter Haven, FL 33884
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  $7,500 Sold Jul 03, 2025

  729 Jenny Wren Rd, Winter Haven, FL 33881

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft
  • Built 1967

  Last Sold Summary

  • 46% Below List Price
  • $10/SF
  • 63 Days On Market

  Last Listing Agent Lillian Lunsford TEAM SHERROD MOBILE HOME SALES, LLC.

  729 Jenny Wren Rd, Winter Haven, FL 33881
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  Est $308,785 Not Listed For Sale

  1905 Manor Cir SE, Winter Haven, FL 33880

  • 4 Beds
  • 2 Baths
  • 2,067 Sq Ft
  • Built 1966

  1905 Manor Cir SE, Winter Haven, FL 33880

  Last Sold Summary

  • 4% Above List Price
  • $144/SF
  • 217 Days On Market

  Last Sold Price $298,000

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  $139,000

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft

  454 Village Cir SW, Winter Haven, FL 33880

  Welcome to your slice of Florida living in Winter Haven! This well-maintained 2-bedroom, 2-bath home offers 1,620 sq ft of comfortable living space and is packed with valuable upgrades, including the ROOF 2023 and 4 ton A/C 2023, water softener, reverse osmosis system, and rain gutters with leaf guards for added peace of mind. Step inside to find a spacious floor plan. Relax and unwind in the

  

  Carolyn Christian

  Dalton Wade Inc

  (863) 329-2319

  454 Village Cir SW, Winter Haven, FL 33880
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  /16

  $1,870 per month

  • 3 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • House for Rent

  108 Brad Cir, 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,

  108 Brad Cir, Winter Haven, FL 33880
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  $325,990 Sold Aug 13, 2025

  4944 Kaia Ave, Winter Haven, FL 33884

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $133/SF
  • 8 Days On Market

  Current Estimated Value $328,316

  D.R. Horton VillaMar

  4944 Kaia Ave, Winter Haven, FL 33884
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  /2

  Est $250,531 Not Listed For Sale

  129 Homewood Dr, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,462 Sq Ft
  • Built 1993

  129 Homewood Dr, Winter Haven, FL 33880

  Last Sold Summary

  • 7% Above List Price
  • $161/SF
  • 114 Days On Market

  Last Sold Price $235,000

  Last Listing Agent John-Michael Elliott S & D REAL ESTATE SERVICE LLC

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